8122019 Tian et al 2013

httpslidepdfcomreaderfulltian-et-al-2013 112

Controlling lipid oxidation of food by active packagingtechnologies

Fang Tian Eric A Decker and Julie M Goddard

Active packaging is an innovative strategy in preventing lipid oxidation Different active substances with

different mechanisms of action have been investigated for imparting antioxidant activity to active

packaging systems including free radical scavengers metal chelators ultraviolet (UV) absorbers oxygen

scavengers and singlet oxygen quenchers Antioxidant agents have been incorporated into active

packaging systems in different forms mainly including independent sachet packages adhesive-bonded

labels physical adsorptioncoating on packaging material surface being incorporated into packaging

polymer matrix multilayer 1047297lms and covalent immobilization onto the food contact packaging surface

In this paper we review recent advances in antioxidant active packaging with the highlight of thedevelopment and application of non-migratory active packaging systems The potential use of emerging

technologies in antioxidant active packaging is also emphasized We further describe challenges and

opportunities towards the commercial application of such antioxidant active packaging systems with a

focus on maintaining safety quality and nutrition of packaged foods

Introduction

Lipid oxidation in the food industry

Lipids play a critical role in food quality in terms of nutrition

(eg essential fatty acids and fat soluble vitamins) mouth

feel (eg cocoa butter in confections) satiety and health

promotion (eg omega-3 fatty acids conjugated linoleic acid)Unfortunately lipids are one of the main targets of oxidative

reactions which are a major problem in both natural and pro-

cessed food products Lipid oxidative reactions can cause food

quality deterioration including off -odors off -avors texture

and color changes and nutrition losses and therefore lead to a

signicant reduction in product shelf life and ultimately

product loss12

Unsaturated fatty acids and oxygen are the two main

components involved in lipid oxidative reactions3 The oxida-

tion of unsaturated fatty acids generates lipid hydroperoxides asthe primary products in the early stage which are colorless

odorless and tasteless4 However they are unstable and

susceptible to decomposition yielding secondary oxidation

products which are a complex mixture of lower molecular

weight volatile and non-volatile compounds The schematic

process of lipid oxidation is shown in Fig 1 A more detailed

discussion of the formation of oxidation products can be found

Fang Tian received her Masters

degree in Food Science from

China Agricultural University in 2009 Then she continued

pursuing PhD degree in Food

Science at University of Massa-

chusetts Amherst She is

currently a nal year PhD

student investigating the

control of lipid oxidation of food

by non-migratory active pack-

aging lms

Eric Decker is Professor and Department Head of UMass Food

Science Dr Decker actively conducts research to characterize

mechanisms by which lipids and antioxidants oxidize in foods and associated health implications He has over 300 publications and

was named one of the Most Highly Cited Scientists in Agriculture

Dr Decker has served on numerous committees including work with

the FDA and the Institute of Medicine His research has been

recognized by awards from the Institute of Food Technologists the

American Oil Chemist Society the Agriculture and Food Chemistry

Division of the American Chemical Society and the International

Life Science Institute

Department of Food Science University of Massachusetts Chenoweth Lab 102

Holdsworth Way Amherst Massachusetts 01003 USA E-mail goddardfoodsci

umassedu Fax +1 413-545-1262 Tel +1 413-545-2275

Cite this Food Funct 2013 4 669

Received 4th December 2012

Accepted 28th March 2013

DOI 101039c3fo30360h

wwwrscorgfoodfunction

This journal is ordf The Royal Society of Chemistry 2013 Food Funct 2013 4 669ndash680 | 669

Food amp Function

REVIEWView Article OnlineView Journal | View Issue

8122019 Tian et al 2013

httpslidepdfcomreaderfulltian-et-al-2013 212

in Chaiyasit et al5 It is the secondary oxidation products (ie the

low molecular weight volatile compounds) that result in the

unacceptable rancid odors and avors of food products In

addition research has shown that oxidized lipids from the diet could directly contribute to major illnesses (eg cancers heart

diseases etc) in human body67 Therefore lipid oxidative

deterioration has been a large economic and health concern in

food industry

Antioxidants in food products

Because of the signicantly harmful eff ect of lipid oxidation a

variety of synthetic and natural antioxidants have been added

directly into food products to inhibit oxidative reactions and

preserve food quality and nutrition Lipid oxidation can be

controlled by preventing the formation of lipid hydroperoxides

and free radicals or by scavenging the free radicals generated infood systems On the basis of the mechanism of action anti-

oxidants can be classied as either primary or secondary anti-

oxidants with some active agents possessing both mechanisms

of action (Table 1)5

Synthetic antioxidants such as butylated hydroxyanisole

(BHA) butylated hydroxytoluene (BHT) and ethylenediamine

tetraacetic acid (EDTA) are commonly used and are very eff ec-

tive in controlling oxidative deterioration in food systems

However in recent years synthetic antioxidants are increasingly

being perceived negatively by consumers who want all

natural foods Use of natural antioxidants may therefore be

advantageous in terms of consumer acceptability Nevertheless

larger amounts of natural antioxidants are typically neededcompared to their synthetic counterparts in order to impart the

same antioxidant activity in the food system and their safety

limits are mostly unknown8 Some of the natural antioxidants

(eg vitamin C tocopherols etc) have shown prooxidant activity

at high concentrations910 Incorporating antioxidants (synthetic

or natural) into product formulations may also adversely aff ect

food quality attributes such as taste color and viscosity11 There

is therefore an interest in identifying technologies to prevent

lipid oxidation beyond food additives The development of

antioxidant active packaging materials represents such an

alternative strategy In this review we highlight recent advances

and emerging technologies in antioxidant active packaging Wefurther describe opportunities and challenges towards

commercial application of such antioxidant active packaging

systems with a focus on maintaining quality and nutrition of

packaged foods

Antioxidant packaging systems

Packaging has long been used to extend the shelf life of foods by

providing an inert barrier to external conditions12 Active

packaging goes beyond the traditional role of packaging by

imparting specic intentional functionality to the packaging

system Active packaging can be designed to extend shelf life

impart post-package processing or improve food safety andquality11314 Antioxidant packaging includes antioxidant

substances in food packaging systems to impart antioxidant

activity A lot of research has been done regarding applications

of antioxidant packaging in various food systems including

meat sh poultry cereal lipid and lipid products11113ndash15

Antioxidant agents in antioxidant food packaging systems

Primary antioxidants Both primary (free radical scavenging)

and secondary (chelators UV absorbers oxygen scavengers and

singlet oxygen quenchers) antioxidants may be incorporated

Fig 1 Schematic process of lipid oxidation The mechanism is adapted from

Chaiyasit et al5 In_ LH L_ LOO_ LOOH and LO_ are initiator radical lipid molecule

alkyl radical peroxylradical lipid hydroperoxides and alkoxyl radical respectively

Table 1 Classi1047297cation of representative antioxidants for the use or potential use

in antioxidant food packaging systems

Antioxidants Classes Representative active agents

Primary Free-radicalscavengers

Synthetic BHA BHT propylene glycol(PG) tert -butylhydroquinone (TBHQ)Natural plant extracts (eg from green teabarley husks) tocopherols essential oils(eg from rosemary oregano cinnamon)

Secondary Chelators Synthetic EDTA poly(acrylic acid) etcNatural citric acid lactoferrin etc

UV absorbers

Synthetic benzophenones benzotriazolespigments (eg phtalocyanine TiO2) etc

Oxygenscavengers

Inorganic metal-based powderNatural ascorbic acid catechins enzymesoxygen consuming spores and yeasts etc

Singlet oxygen (1O2)quenchers

Natural carotenoids tocopherolspolyphenols etc

Julie Goddard is an Assistant Professor in the Department of Food

Science at UMass Amherst Dr Goddards research group focuses on

manipulating the chemistry of materials used to handle process

and package food in order to improve the quality safety and

environmental sustainability of our food supply Prior to

completing a PhD in Food Science Dr Goddard worked as a

Chemical Engineer at Kra Foods She also has research experience

as a postdoctoral researcher on nanobiotechnology Dr Goddard

has published 25 peer reviewed journal articles since she began

publishing in 2007

670 | Food Funct 2013 4 669ndash680 This journal is ordf The Royal Society of Chemistry 2013

Food amp Function Review

View Article Online

8122019 Tian et al 2013

httpslidepdfcomreaderfulltian-et-al-2013 312

into antioxidant active packaging materials to preserve food

quality (Table 1) Primary antioxidants are free radical scaven-

gers which can donate hydrogen to reactive free radicals (eg L_

LO_ LOO_ etc) and form free radicals themselves that are stable

enough not to cause further initiation or propagation reactions

in the lipid oxidation process A description of some common

primary antioxidants for potential application to antioxidant

active packaging systems follows Synthetic free radical scav-

engers BHA and BHT especially BHT have been widely coatedor incorporated into a variety of polymers like low-density

polyethylene (LDPE) and poly(lactic acid) (PLA) to develop

antioxidant packaging lms16ndash20 Even though these economical

active lms presented high eff ectiveness and stability they are

still considered as ldquolabel unfriendly rdquo The application of free

radical scavengers from natural sources has therefore been a

trend in recent years Tocopherols essential oils from herbs

(eg rosemary oregano and cinnamon) and plant extracts (eg

antioxidant extracts from barley husk green tea citrus mint

and pomegranate peel) are all being investigated in the devel-

opment of antioxidant active packaging systems by diff erent

application forms (Table 2)Secondary antioxidants Secondary antioxidants prevent

oxidative reaction by chelating metals screening UV light

scavenging oxygen and quenching singlet oxygen (1O2) Below

is a review of current and potential applications of secondary

antioxidants in antioxidant active packaging

Chelators Transition metals have been reported to play an

important role in promoting lipid oxidation reactions21 Iron

and copper are the main transition metals commonly found in

foods and iron o en exists at higher concentration than

copper5 These metals can accelerate the decomposition of lipid

hydroperoxides and the generation of reactive oxygen species

(LO_ HO_ and LOO_)522 Metals in their reduced states (eg Fe2+)

are able to signicantly accelerate the hydroperoxide degrada-tion resulting in their conversion to the oxidized state (eg Fe3+)

The oxidized state metals can be slowly reduced back to their

reduced states by the reaction with hydroperoxides or can be

rapidly reduced by agents such as ascorbic acid23 As the reac-

tions are cyclical metals can considerably promote the lipid

oxidative reactions even with a very low concentration in food

products (down to part per billion)

Chelators are chemical compounds capable of forming a

heterocyclic ring with metal ions as the closing members

(Fig 2) A er being chelatedbound by chelators metals can

completely or partially lose the ability to accelerate lipid

oxidative reactions However so far not much research hasbeen done employing metal chelators to develop antioxidant

active packaging EDTA is the most commonly used synthetic

metal chelator in food and beverage industry Unalan et al

incorporated Na2EDTA into edible zein lms to inhibit the lipid

oxidation on ground beef patties24 Metal chelating polymer

poly(acrylic acid) (PAA) has also been covalently immobilized

onto LDPE and polypropylene (PP) lm surfaces to control lipid

oxidation in oil-in-water emulsion systems2526 The covalent

nature of the bond means that the active agent is unlikely to

migrate to the food a potential regulatory advantage27 No

natural metal chelators have been applied in antioxidant active

packaging Citric acid and iron-binding proteins (eg lacto-

ferrin) are naturally occurring metal chelators and have great

potential for the application in natural antioxidant packaging

systems28

UV absorbers Light especially in the UV range (wavelength

below 400 nm) is one of the major external energy sources

initiating the photo-oxidation of lipids The light transmission

capacity of packaging materials can signicantly aff ect the

quality of packaged food products Diff erent plastic materials vary in light barrier property and most of the commonly used

packaging materials would to some extent allow the trans-

mission of UV light Light throughout the UV range can pene-

trate LDPE high-density polyethylene (HDPE) and PP while

polyethylene terephthalate (PET) can partially block UV light

(below 300 nm)29 Light stabilizers are therefore added into a

variety of plastics to protect them from degradation and to

prevent the photo-oxidation in the packaged products UV

absorbers are a class of light stabilizers that can absorb the

energy of UV irradiation Benzophenones benzotriazoles and

some pigments (eg phtalocyanine TiO2) are commonly used

UV absorbers

30

and some of them have already been incorpo-rated into polymeric packaging materials (PP PET HDPE etc)

to control oxidative reactions in edible oils293132

Oxygen scavengers The presence of oxygen promotes the lipid

oxidative reactions in packaged food products Traditional

techniques like modied atmosphere packaging (MAP) or

vacuum packaging can be applied to remove oxygen from the

food packaging system However the 100 removal of oxygen

by these techniques is very difficult and uneconomical as the

expulsion of the last 5ndash10 of oxygen requires longer time and

larger volume of higher purity inert gas33 A er packaging

oxygen could also come from the food itself the packaging

materials the permeation of air through the package or a poor

sealing and microperforations in the packaging system34 Toeliminate the undesirable oxygen residue various oxygen scav-

engers (also known as oxygen absorbers) have been investigated

over last 30 years In recent years a lot of oxygen-scavenging

systems have been successfully commercialized1131434ndash36

Three major types of active substances have been used to

develop oxygen-scavenging systems including metals enzymes

and small naturalbiological molecules The majority of

commercially available oxygen scavengers are based on metallic

oxidation especially iron and iron-based powder oxida-

tion137ndash40 Enzymatic oxidation is another oxygen-scavenging

strategy in which an enzyme reacts with a substrate to scavenge

oxygen The most popular enzymatic oxygen scavenging systemis the combination of glucose oxidase and catalase (Fig 3)4142

In this system glucose oxidase reacts with glucose in the pres-

ence of oxygen and water to generate hydrogen peroxide which

catalase decomposes back into water and half the original

amount of oxygen (Fig 3)42 This enzyme system has been

embedded into acrylate polymer matrixes for the deoxygenation

of apple juice43 The third class of oxygen scavenger is based on

other natural or biological components including small anti-

oxidant molecules (ascorbic acid catechol etc) oxygen-

consuming spores yeast rice extract etc44ndash47 Small antioxidant

molecules like ascorbic acid are readily auto-oxidized and the

This journal is ordf The Royal Society of Chemistry 2013 Food Funct 2013 4 669ndash680 | 671

Review Food amp Function

View Article Online

8122019 Tian et al 2013

httpslidepdfcomreaderfulltian-et-al-2013 412

reaction between them with oxygen produces reactive oxygen

species (hydrogen peroxide etc) They could be applied in

oxygen scavenging packaging systems by the forms of sachets

(Fig 4A) incorporation (Fig 5B)47 and multilayer lms (Fig 5C)

By these application forms antioxidants could remove the

oxygen inside of the packaging system while the generated

reactive oxygen species being trapped in packaging materials

Ascorbic acid can also be used in combination with a transition

metal (eg copper) to absorb oxygen in food systems and the

metalndashascorbate complex is able to quickly reduce the gener-

ated hydrogen peroxide to water without forming any free

radicals37

Natural oxygen scavengers are receiving moreinterest due to their potentially advantageous consumer

perception and sustainability

Singlet oxygen ( 1O 2 ) quenchers Singlet oxygen is the excited

state of the normal triplet state oxygen usually generated in the

presence of light and photosensitizers (chlorophyll riboavin

myoglobin etc) This high-energy molecule is much more

unstable than the triplet state oxygen and is prone to accelerate

the generation of lipid hydroperoxides Singlet oxygen

quenchers can deplete the excess energy of singlet oxygen to

control lipid oxidation22 The natural primary antioxidants

including polyphenols (eg catechins and avonoids)

carotenoids (eg b-carotene lycopene and lutein) and

tocopherols can also act as singlet oxygen quenchers to prevent

the photooxidation of unsaturated fatty acids5 Some applica-

tions of these natural antioxidants in active packaging are

shown in Table 2

Technologies for preparation of antioxidant packaging

Antioxidant agents can be applied into the packaging systems in

diff erent forms mainly including independent sachet pack-

ages adhesive-bonded labels physical adsorptioncoating on

packaging material surface being incorporated into packaging polymer matrix multilayer lms and covalent immobilization

onto the food contact packaging surface The mechanism of

activity of a given antioxidant along with the intended product

application must be considered when designing the antioxi-

dant active packaging system

Sachets and labels Sachets are commonly used for oxygen-

scavenging packaging systems Oxygen scavengers mainly iron

or iron-based powder are kept in a small sachet that is made of

highly oxygen permeable material (Fig 4A) These oxygen-

absorbing systems have the ability to reduce the oxygen level to

less than 001 in many foods including meat products bakery

Table 2 Applications of representative antioxidants in active packaging systems

Antioxidants Packaging materials Application formsb Ref

BHA PLA LDPE EVOH HDPE Multilayer incorporated 16ndash18 and 48BHT PLA LDPE EVOH HDPE Multilayer coating incorporated 16ndash20 and 48EDTA Zein lm Incorporated 24PAA LDPE PP Immobilized 25 and 26UV absorbers (benzotriazolesphtalocyanine and TiO2)

PP PET HDPE Incorporated 29 31 and 32

Metal-based O2 scavenger Highly oxygen permeable materials Sachet 1 38 40 and 49Metal-based O2 scavenger PET PP EVOH laminate sh

gelatin lmIncorporated multilayer 39 and 50ndash53

a-Tocopherol PLA LDPE EVOH HDPE shgelatin lm EVA PP papera

Multilayer coating incorporated 4 17ndash19 48 51 and 54ndash57

Natural antioxidants from barley husks mint yerba mate citrus andpomegranate peel (phenoliccompounds)

LDPE PET chitosanndashPVA cassavastarch lm

Coating incorporated 15 and 58ndash63

Green tea extract EVOH chitosan lm Incorporated 64ndash66Rosemary extract LDPE PP chitosan lm Coating incorporated 48 and 67ndash71Natural essential oil extracts (fromginger oregano cinnamon)

PP Self-adhesive label incorporatedcoating

69 and 72ndash74

Natural antioxidants (ascorbic acidferulic acid caff eic acid quercetincatechin epicatechin carvacroltyrosine)

EVOH HDPE LDPE EVA PP PLAcellulose acetate lm caseinatelms

Incorporated multilayerimmobilized

4 11 55 65 and 75ndash80

Mango and acerola pulps(polyphenols and carotenoids)

Starch lm Incorporated 10

Protein (whey protein isolate soy protein isolate)

PP Coating 81

Enzyme (laccases) Styrene-butadien latexclay matrix Incorporated 82Enzyme (glucose oxidase andcatalase)

Acrylate polymers Incorporated immobilized 43 and 83

a Using vinyl acetatendashethylene copolymer as the binder medium b The schematic structure of the application form coating incorporatedmultilayer and immobilized is corresponding to Fig 5A B C and D respectively

672 | Food Funct 2013 4 669ndash680 This journal is ordf The Royal Society of Chemistry 2013

Food amp Function Review

View Article Online

8122019 Tian et al 2013

httpslidepdfcomreaderfulltian-et-al-2013 512

8122019 Tian et al 2013

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materials69717485 Usually to apply antioxidants in the form of

coating a support material is required as a vehicle to carry

active agents onto packaging surfaces However there are some

exceptions Rosemary citrus and barley husk extracts were

dissolved in organic solvent and then distributed on packaging

surfaces to form a coating layer a er the evaporation of

solvents1560626368 Lee et al modied PP lm surface by corona

treatment to increase its wettability on the purpose of

improving the adhesion of protein coatings on lm surface81

Incorporated In addition to coating an antioxidant onto the

food contact surface of a package the antioxidant may be

incorporated throughout the package (Fig 5B) By dispersing

the antioxidant in the polymeric matrix antioxidant activity can

be exerted not only on the package headspace and the food

product but also by preventing the oxidation accelerating

factors (mainly oxygen) from permeating through the package

from the external environment Various antioxidant substances

have been incorporated into diff erent packaging materials to

make active lms (Table 2) This approach is almost applicable

for all kinds of antioxidant to prepare active lms by either

casting

2451585965ndash677580

or extrusion

16193950647879

manufacturing processes Although these lms are eff ective they may impart

undesirable avor to foods especially when iron-based oxygen

scavengers are used The possible migration of iron into foods

may accelerate lipid oxidative reactions In addition large

amounts of antioxidants are needed to disperse them

throughout the whole package and major mass and activity

losses may also occur during the manufacturing process

Multilayer active lms Multilayer packaging in which the

antioxidant-containing layer is sandwiched between inert layers

(Fig 5C) may overcome some incorporated active lm related

concerns but with higher costs Ferrous iron based commercial

oxygen scavenger layer was introduced into multiple inert layers

to prepare PPEVOHOSPP (EVOH ethyl vinyl alcohol OSoxygen scavenger) multilayer antioxidant packaging lms53

Synthetic antioxidants BHA and BHT have been incorporated

with LDPE and then coextruded with HDPE and EVOH to

develop functional lms1718 BHT also has been incorporated

into waxed paper liners to inhibit the rancidity in breakfast

cereal and snack food products Natural compounds a-tocoph-

erol and quercetin were sandwiched between two layers of

EVOH ethylene vinyl acetate (EVA) LDPE and PP respectively

to impart antioxidant activity to these commonly used normal

packaging polymers55 Park et al77 also sandwiched natural

antioxidants thymol carvacrol and eugenol into two layers of

LDPE to prepare multi-layered active

lms So far the applica-tion of multilayer active lms is not as widespread as that of

sachets coating and incorporated approaches due to its high

cost and more complicated manufacturing process

Covalent immobilization Traditional approaches to active

packaging development including antioxidant active pack-

aging is either to coat the active agent onto or blend it

throughout the package material Such approaches depend on

the migration or transfer of active agents to food products to be

eff ective Eventually not only would the packages lose activity

but the antioxidants would inevitably enter the food product as

additives which remains consumer dissatises and regulatory

hurdle Moreover entrapment of active agents within a polymer

matrix would likely aff ect the mechanical and optical properties

of the packaging material86 Recently there is increasing

interest in covalent immobilization of functional compounds

onto the food contact surface of packaging lms

(Fig 5D)112526838687 Covalent bonds can provide the most stable

linkage between substrate lm surface and active agents a

potential regulatory benet The active agents may not need to

be labeled as food additives as they are not likely to migratefrom the package to the food27

Surface functionalization Commonly used polymers for food

packaging include LDPE HDPE PP PET polyvinyl alcohol

(PVA) polystyrene (PS) etc Such commercially available poly-

mers have an inert nature and must be pretreated to introduce

reactive sites on the polymer surface for the attachment of

functional compounds Several surface modication techniques

have been developed to do the surface functionalization mainly

including wet chemical ionized gas treatments and UV irradi-

ation (Fig 6)88 In wet chemical method materials are treated

with concentrated corrosive liquid reagents to produce a range

of oxygen-containing reactive groups on the surface While thismethod is eff ective to introduce reactive functional groups it is

non-specic and would generate hazardous chemical waste The

most commonly used ionized gas treatment is plasma which

can modify the top nanometer of the polymer surface without

producing any hazardous chemical waste Specic reactive

functional groups like carboxyl groups and amine groups can be

imparted to inert polymer surfaces by using diff erent plasma

gases (O2 CO2 N2 etc) UV irradiation is another physical

technique to do the surface modication on the top nanometer

of a polymer surface UV light can be used to create functional

groups or free radicals to further initiate gra polymerization of

functional monomers Short-wave UV light (UVC 185 nm) can

react with atmospheric oxygen to generate atomic oxygen andozone and ozone dissociates into molecular oxygen and atomic

oxygen by absorbing the 254 nm UV radiation (UVC) Both of

atomic oxygen and ozone are strong oxidizers producing peroxy

radicals which are capable of initiating gra polymerization At

the same time peroxy radicals are unstable species and very

susceptible to be decomposed to form reactive moieties

including carboxyl carbonyl and hydroxyl groups89 Barish and

Goddard90 investigated the molecular and topographical eff ects

of these common chemical and physical surface modication

techniques (wet chemical oxidation oxygen plasma and short-

wave UV irradiation) on LDPE lm by comparing the resulting

changes in surface chemistry wettability and topography UV irradiation was reported as the best surface functionalization

method90 Long-wave UV light (UVA 400ndash315 nm) combined

with photoinitiatorssensitizers (benzophenone etc) can be

used to convert light energy into useful chemical energy by

abstracting hydrogen from the polymer substrate to generate

free radicals on the surface91 The free radicals are able to initiate

the gra polymerization of functional monomers from polymer

surfaces (Fig 7C)

The quantity and type of reactive functional moieties are

limited on polymer surfaces introduced by the initial surface

functionalization process To solve this issue cross-linking

674 | Food Funct 2013 4 669ndash680 This journal is ordf The Royal Society of Chemistry 2013

Food amp Function Review

View Article Online

8122019 Tian et al 2013

httpslidepdfcomreaderfulltian-et-al-2013 612

materials69717485 Usually to apply antioxidants in the form of

coating a support material is required as a vehicle to carry

active agents onto packaging surfaces However there are some

exceptions Rosemary citrus and barley husk extracts were

dissolved in organic solvent and then distributed on packaging

surfaces to form a coating layer a er the evaporation of

solvents1560626368 Lee et al modied PP lm surface by corona

treatment to increase its wettability on the purpose of

improving the adhesion of protein coatings on lm surface81

Incorporated In addition to coating an antioxidant onto the

food contact surface of a package the antioxidant may be

incorporated throughout the package (Fig 5B) By dispersing

the antioxidant in the polymeric matrix antioxidant activity can

be exerted not only on the package headspace and the food

product but also by preventing the oxidation accelerating

factors (mainly oxygen) from permeating through the package

from the external environment Various antioxidant substances

have been incorporated into diff erent packaging materials to

make active lms (Table 2) This approach is almost applicable

for all kinds of antioxidant to prepare active lms by either

casting

2451585965ndash677580

or extrusion

16193950647879

manufacturing processes Although these lms are eff ective they may impart

undesirable avor to foods especially when iron-based oxygen

scavengers are used The possible migration of iron into foods

may accelerate lipid oxidative reactions In addition large

amounts of antioxidants are needed to disperse them

throughout the whole package and major mass and activity

losses may also occur during the manufacturing process

Multilayer active lms Multilayer packaging in which the

antioxidant-containing layer is sandwiched between inert layers

(Fig 5C) may overcome some incorporated active lm related

concerns but with higher costs Ferrous iron based commercial

oxygen scavenger layer was introduced into multiple inert layers

to prepare PPEVOHOSPP (EVOH ethyl vinyl alcohol OSoxygen scavenger) multilayer antioxidant packaging lms53

Synthetic antioxidants BHA and BHT have been incorporated

with LDPE and then coextruded with HDPE and EVOH to

develop functional lms1718 BHT also has been incorporated

into waxed paper liners to inhibit the rancidity in breakfast

cereal and snack food products Natural compounds a-tocoph-

erol and quercetin were sandwiched between two layers of

EVOH ethylene vinyl acetate (EVA) LDPE and PP respectively

to impart antioxidant activity to these commonly used normal

packaging polymers55 Park et al77 also sandwiched natural

antioxidants thymol carvacrol and eugenol into two layers of

LDPE to prepare multi-layered active

lms So far the applica-tion of multilayer active lms is not as widespread as that of

sachets coating and incorporated approaches due to its high

cost and more complicated manufacturing process

Covalent immobilization Traditional approaches to active

packaging development including antioxidant active pack-

aging is either to coat the active agent onto or blend it

throughout the package material Such approaches depend on

the migration or transfer of active agents to food products to be

eff ective Eventually not only would the packages lose activity

but the antioxidants would inevitably enter the food product as

additives which remains consumer dissatises and regulatory

hurdle Moreover entrapment of active agents within a polymer

matrix would likely aff ect the mechanical and optical properties

of the packaging material86 Recently there is increasing

interest in covalent immobilization of functional compounds

onto the food contact surface of packaging lms

(Fig 5D)112526838687 Covalent bonds can provide the most stable

linkage between substrate lm surface and active agents a

potential regulatory benet The active agents may not need to

be labeled as food additives as they are not likely to migratefrom the package to the food27

Surface functionalization Commonly used polymers for food

packaging include LDPE HDPE PP PET polyvinyl alcohol

(PVA) polystyrene (PS) etc Such commercially available poly-

mers have an inert nature and must be pretreated to introduce

reactive sites on the polymer surface for the attachment of

functional compounds Several surface modication techniques

have been developed to do the surface functionalization mainly

including wet chemical ionized gas treatments and UV irradi-

ation (Fig 6)88 In wet chemical method materials are treated

with concentrated corrosive liquid reagents to produce a range

of oxygen-containing reactive groups on the surface While thismethod is eff ective to introduce reactive functional groups it is

non-specic and would generate hazardous chemical waste The

most commonly used ionized gas treatment is plasma which

can modify the top nanometer of the polymer surface without

producing any hazardous chemical waste Specic reactive

functional groups like carboxyl groups and amine groups can be

imparted to inert polymer surfaces by using diff erent plasma

gases (O2 CO2 N2 etc) UV irradiation is another physical

technique to do the surface modication on the top nanometer

of a polymer surface UV light can be used to create functional

groups or free radicals to further initiate gra polymerization of

functional monomers Short-wave UV light (UVC 185 nm) can

react with atmospheric oxygen to generate atomic oxygen andozone and ozone dissociates into molecular oxygen and atomic

oxygen by absorbing the 254 nm UV radiation (UVC) Both of

atomic oxygen and ozone are strong oxidizers producing peroxy

radicals which are capable of initiating gra polymerization At

the same time peroxy radicals are unstable species and very

susceptible to be decomposed to form reactive moieties

including carboxyl carbonyl and hydroxyl groups89 Barish and

Goddard90 investigated the molecular and topographical eff ects

of these common chemical and physical surface modication

techniques (wet chemical oxidation oxygen plasma and short-

wave UV irradiation) on LDPE lm by comparing the resulting

changes in surface chemistry wettability and topography UV irradiation was reported as the best surface functionalization

method90 Long-wave UV light (UVA 400ndash315 nm) combined

with photoinitiatorssensitizers (benzophenone etc) can be

used to convert light energy into useful chemical energy by

abstracting hydrogen from the polymer substrate to generate

free radicals on the surface91 The free radicals are able to initiate

the gra polymerization of functional monomers from polymer

surfaces (Fig 7C)

The quantity and type of reactive functional moieties are

limited on polymer surfaces introduced by the initial surface

functionalization process To solve this issue cross-linking

674 | Food Funct 2013 4 669ndash680 This journal is ordf The Royal Society of Chemistry 2013

Food amp Function Review

View Article Online

8122019 Tian et al 2013

httpslidepdfcomreaderfulltian-et-al-2013 712

agents with morediff erent functional groups are necessary to

maximize the amount or to introduce other types of groups also

to reduce the steric hindrance from the substrate polymer

surface Fig 7A depicts a typical reaction procedure to introduce

more available functional carboxylic acids to the pretreated

packaging lm surface using amine compound (ethylene

diamine) as the cross-linking agent Goddard and Hotchkiss92

pretreated clean LDPE lm surface by wet chemical technique

at rst to introduce carboxylic acid groups Functional cross-linking agents (polyethylenimine ethylenediamine ethanol-

amine glutaraldehyde and Trauts reagent) were then applied

to introduce a range of other reactive moieties including amine

(ndashNH2) aldehyde (ndashCOH) thiol (ndashSH) and hydroxyl (ndashOH) for

the further covalent attachment of bioactive compounds Barish

and Goddard93 developed a versatile platform for the non-

migratory attachment of amine functional compounds by

gra ing a biocompatible polymer (polyethylene glycol PEG)

from the UVO3 treated LDPE lm surface

Immobilization of functional compounds While its commercial

potential has not yet been realized considerable research has

been reported in recent years towards the application of cova-lent immobilization technologies in active food packaging

Naringinase was immobilized onto cellulose acetate lms to

reduce the bitterness of processed grapefruit juice94 Lactase

was covalently attached to pre-functionalized LDPE lm surface

for the reduction of lactose in dairy products86 Antimicrobial

active packaging was also developed by the bound of lysozyme

onto the cross-linked PVA matrix using glutaralydehyde as the

binding agent87 Diff erent kinds of antioxidants had also been

applied to develop antioxidant-packaging materials The oxygen

scavenging enzyme glucose oxidase was covalently immobilized

onto carboxylated styrene acrylate latex particles and lms

formed by particles using bioconjugation reaction (Fig 7B)

They also reported that the activity of enzymes immobilized tolm surface was 10 times higher than that of enzymes entrap-

ped within the polymer matrix83 Phenolic compound caff eic

acid was immobilized onto a PP lm surface through the

covalent attaching of caff eoyl chloride on a functionalized

polymeric surface of PP lm photo-gra ed with poly-

(hydroxyethyl methacrylate)11 Metal-chelating polymer poly-

(acrylic acid) (PAA) was gra ed to a LDPE lm surface via the

combination of UV irradiation (short-wave) and bioconjugation

chemistry techniques while it was also gra ed from a PP lm

surface via the photoinitiated (long-wave UV light) gra poly-

merization of acrylic acid monomers2526 The gra ing-to tech-

nique used in the former research directly gra ed functional

polymers to the pre-functionalized lm surface (Fig 7B) Thegra ing-from technique used in the latter one introduced the

functionality by the free radical chain reaction of monomers to

polymerize into polymers from the lm surface (Fig 7C)

Gra ing-from technique can yield much higher density of

functional groups than the gra ing-to technique which largely

relies on the amount of active groups on the lm surface

generated by the pre-functionalization treatment2526 In this

work Tian et al demonstrated the ability to chelate 7107

1295 nmol cm2 ferrous ions resulting in a signicant exten-

sion in the lag phase of oxidation of an oil-in-water emulsion

system This work shows the potential of an antioxidant active

packaging technology which could enable removal of asynthetic additive (EDTA) from product formulations while

maintaining product quality

Along with the regulatory advantages covalent immobiliza-

tion technologies can potentially enable active packaging to

possess longer-term activity However immobilized antioxi-

dants need to contact with food products directly to impart the

functionality which connes the application of this technology

to liquid and semi-liquid food products95

Emerging technologies for potential use inantioxidant active packaging

Only a limited number of antioxidants are food grade additives

and very few new antioxidant compounds have been approved

Fig 6 Representative reaction scheme of the three surface functionalization

techniques commonly used on inert packaging 1047297lms wet chemical plasma

treatment and short-wave UV irradiation

Fig 7 Reaction schemes of techniques used for the further functionalization of

packaging 1047297lm surfaces and the immobilization of active substances (A) bio-

conjugation chemistry method (B) grafting-to method and (C) grafting-from

method

This journal is ordf The Royal Society of Chemistry 2013 Food Funct 2013 4 669ndash680 | 675

Review Food amp Function

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8122019 Tian et al 2013

httpslidepdfcomreaderfulltian-et-al-2013 812

8122019 Tian et al 2013

httpslidepdfcomreaderfulltian-et-al-2013 912

gas permeability the thermal properties and the optical prop-

erty Bastarrachea et al reviewed the eff ect of active agents on

the engineering properties of antimicrobial packaging lms105

Lopez-de-Dicastillo et al examined the change of water and

oxygen permeabilities the T g crystallinity and thermal resis-

tance and the optical property of EVOH lms before and a er

the incorporation of catechin and quercetin106 Goda et al

determined the oxygen permeability and tensile property

change of polydimethylsiloxane (PDMS) lm a er the gra ing of anti-biofouling compounds onto the lm surface107 Wessling

et al reported undesired changes in engineering properties

(mechanical permeability optical and thermal) of LDPE lms

a er the incorporation of high levels of a-tocopherol57 Jam-

shidian et al revealed that the ascorbyl palmitate coating is not

suitable for PLA active packaging due to its negative eff ect on

the lm optical property54 Thus careful evaluation of engi-

neering properties must be performed to ensure desired prop-

erties of developed active packaging materials as well as to

better understand the feasibility of commercializing them on

industrial scale

Migration of active substances

Due to the deliberate interaction between the food and the food

contact package the stringent examination of the safety of

active packaging would be necessary and more challenged

compared to the traditional packaging New dedicated migra-

tion tests and mass transfer modelling tools need to be devel-

oped as existing ones for traditional packaging might not be

properly adapted to active systems108 The extent and kinetics of

antioxidant release can be measured by exposing the active

packaging specimen to diff erent types of food simulants using a

certain time and temperature106 In the eld of control-released

antioxidant active packaging migration tests must be per-formed to control the maximum releasing amount of antioxi-

dants in compliance with the food legislation at the same time

to ensure the active packaging being sufficiently eff ective during

a certain storage period Many publications have been recently

devoted to research on the migration of diff erent active

substances from developed active packaging materials Granda-

Restrepo et al determined the migration of a-tocopherol from a

multilayer active packaging to the whole milk powder18 Peltzer

et al studied the migration of carvacrol from HDPE to the food

simulants olive oil and distilled water79 The release of natural

essential oils from PP-based active packaging lms was also

evaluated using three aqueous food simulants (water 3 aceticacid and 10 ethanol)73 Aznar et al analysed the migration of

non-volatile functional compounds (caff eine carvacrol citral

etc) from the active packaging lms based on PP EVOH and

PET using 10 ethanol and 95 ethanol as the aqueous and fat

simulants respectively109 With respect to non-migratory active

packaging dedicated evaluation of migration is also important

to conrm the non-migratory nature of the active packaging

material as this may impact regulatory and labelling consider-

ations Specic migration testing needs to be designed taking

into account the possible formation of decomposition by-

products

Regulations of active packaging

The increasing development of active packaging technologies

challenges the current regulatory framework to address new

technical considerations to ensure the safety quality and

stability of food products that employ such packaging While

the legislation applied to traditional packaging also can be

adapted to active packaging110 specic rules and guidelines

might need to be introduced to clarify myriad related needs for

the application of novel technologies in packaging industry In

the United States current FDA regulatory programs include

food additive petition (FAP) program generally recognized as

safe (GRAS) notication program and food contact substance

(FCS) notication program which provide authorization

process for direct food additives GRAS substances and indirect

additives respectively111 Migratory active packaging should

follow the FAP program or GRAS notication as this technology

releases antioxidants into food for an intended technical eff ect

Non-migratory antioxidant packaging needs to follow the FCS

notication program since the active agent is unlikely to

migrate to the food in the case of non-migratory active pack-

aging111 Japan is also leading the way in the development anduse of active packaging for food and active packaging concepts

have penetrated markets of Australia108 The development of

active packaging in the European Union (EU) market is limited

and most of the concepts on the market of USA Japan and

Australia cannot be introduced in Europe yet mainly due to the

inadequate and more stringent EU legislation102108 The regu-

lation of active packaging in EU is still evolving and certain

inherent constraints in the law such as the overall migration

limit result in a set of hurdles for the regulation to keep up with

the rapidly developed technological innovations112 The new

active and intelligent packaging directive introduced in 2009

across Europe (EC Regulation 4502009) is expected to bring

much-needed clarity to this sector and pave the way for the

launch of new products onto the European market

Conclusions

The application of active packaging is a novel strategy in

controlling lipid oxidation So far research on antioxidant active

packaging has focused predominantly on migratory packaging

systems by incorporating active substances (mainly from natural

sources) into a variety of packaging materials Non-migratory

active packaging has been receiving increasing interests recent

years to reduce the usage of food additives More research isneeded to design and develop more innovative economical and

commercializable active packaging materials to limit lipid oxida-

tion while minimizing incorporation and consumption of food

additives At the same time the public awareness of active pack-

aging also needs to be improved to increase the consumer

acceptance of such innovations which would enable scaled-up

production and therefore dramatically reductions the cost of such

packaging materials13 Antioxidant active packaging is a devel-

oping technology and the research into it is still in its early stages

Further improvements are always needed to provide consumers

with food products of the highest quality and safety

This journal is ordf The Royal Society of Chemistry 2013 Food Funct 2013 4 669ndash680 | 677

Review Food amp Function

View Article Online

8122019 Tian et al 2013

httpslidepdfcomreaderfulltian-et-al-2013 912

gas permeability the thermal properties and the optical prop-

erty Bastarrachea et al reviewed the eff ect of active agents on

the engineering properties of antimicrobial packaging lms105

Lopez-de-Dicastillo et al examined the change of water and

oxygen permeabilities the T g crystallinity and thermal resis-

tance and the optical property of EVOH lms before and a er

the incorporation of catechin and quercetin106 Goda et al

determined the oxygen permeability and tensile property

change of polydimethylsiloxane (PDMS) lm a er the gra ing of anti-biofouling compounds onto the lm surface107 Wessling

et al reported undesired changes in engineering properties

(mechanical permeability optical and thermal) of LDPE lms

a er the incorporation of high levels of a-tocopherol57 Jam-

shidian et al revealed that the ascorbyl palmitate coating is not

suitable for PLA active packaging due to its negative eff ect on

the lm optical property54 Thus careful evaluation of engi-

neering properties must be performed to ensure desired prop-

erties of developed active packaging materials as well as to

better understand the feasibility of commercializing them on

industrial scale

Migration of active substances

Due to the deliberate interaction between the food and the food

contact package the stringent examination of the safety of

active packaging would be necessary and more challenged

compared to the traditional packaging New dedicated migra-

tion tests and mass transfer modelling tools need to be devel-

oped as existing ones for traditional packaging might not be

properly adapted to active systems108 The extent and kinetics of

antioxidant release can be measured by exposing the active

packaging specimen to diff erent types of food simulants using a

certain time and temperature106 In the eld of control-released

antioxidant active packaging migration tests must be per-formed to control the maximum releasing amount of antioxi-

dants in compliance with the food legislation at the same time

to ensure the active packaging being sufficiently eff ective during

a certain storage period Many publications have been recently

devoted to research on the migration of diff erent active

substances from developed active packaging materials Granda-

Restrepo et al determined the migration of a-tocopherol from a

multilayer active packaging to the whole milk powder18 Peltzer

et al studied the migration of carvacrol from HDPE to the food

simulants olive oil and distilled water79 The release of natural

essential oils from PP-based active packaging lms was also

evaluated using three aqueous food simulants (water 3 aceticacid and 10 ethanol)73 Aznar et al analysed the migration of

non-volatile functional compounds (caff eine carvacrol citral

etc) from the active packaging lms based on PP EVOH and

PET using 10 ethanol and 95 ethanol as the aqueous and fat

simulants respectively109 With respect to non-migratory active

packaging dedicated evaluation of migration is also important

to conrm the non-migratory nature of the active packaging

material as this may impact regulatory and labelling consider-

ations Specic migration testing needs to be designed taking

into account the possible formation of decomposition by-

products

Regulations of active packaging

The increasing development of active packaging technologies

challenges the current regulatory framework to address new

technical considerations to ensure the safety quality and

stability of food products that employ such packaging While

the legislation applied to traditional packaging also can be

adapted to active packaging110 specic rules and guidelines

might need to be introduced to clarify myriad related needs for

the application of novel technologies in packaging industry In

the United States current FDA regulatory programs include

food additive petition (FAP) program generally recognized as

safe (GRAS) notication program and food contact substance

(FCS) notication program which provide authorization

process for direct food additives GRAS substances and indirect

additives respectively111 Migratory active packaging should

follow the FAP program or GRAS notication as this technology

releases antioxidants into food for an intended technical eff ect

Non-migratory antioxidant packaging needs to follow the FCS

notication program since the active agent is unlikely to

migrate to the food in the case of non-migratory active pack-

aging111 Japan is also leading the way in the development anduse of active packaging for food and active packaging concepts

have penetrated markets of Australia108 The development of

active packaging in the European Union (EU) market is limited

and most of the concepts on the market of USA Japan and

Australia cannot be introduced in Europe yet mainly due to the

inadequate and more stringent EU legislation102108 The regu-

lation of active packaging in EU is still evolving and certain

inherent constraints in the law such as the overall migration

limit result in a set of hurdles for the regulation to keep up with

the rapidly developed technological innovations112 The new

active and intelligent packaging directive introduced in 2009

across Europe (EC Regulation 4502009) is expected to bring

much-needed clarity to this sector and pave the way for the

launch of new products onto the European market

Conclusions

The application of active packaging is a novel strategy in

controlling lipid oxidation So far research on antioxidant active

packaging has focused predominantly on migratory packaging

systems by incorporating active substances (mainly from natural

sources) into a variety of packaging materials Non-migratory

active packaging has been receiving increasing interests recent

years to reduce the usage of food additives More research isneeded to design and develop more innovative economical and

commercializable active packaging materials to limit lipid oxida-

tion while minimizing incorporation and consumption of food

additives At the same time the public awareness of active pack-

aging also needs to be improved to increase the consumer

acceptance of such innovations which would enable scaled-up

production and therefore dramatically reductions the cost of such

packaging materials13 Antioxidant active packaging is a devel-

oping technology and the research into it is still in its early stages

Further improvements are always needed to provide consumers

with food products of the highest quality and safety

This journal is ordf The Royal Society of Chemistry 2013 Food Funct 2013 4 669ndash680 | 677

Review Food amp Function

View Article Online

8122019 Tian et al 2013

httpslidepdfcomreaderfulltian-et-al-2013 1012

Abbreviations

BHA Butylated hydroxyanisole

BHT Butylated hydroxytoluene

DFO Desferrioxamine

DFX Deferasirox

EDTA Ethylenediamine tetraacetic acid

EU European unionEVA Ethylene vinyl acetate

EVOH Ethylene vinyl alcohol

Fe2+ Ferrous ion

Fe3+ Ferric ion

FAP Food additive petition

FCS Food contact substance

FDA Food and drug administration

GRAS Generally recognized as safe

HDPE High-density polyethylene

H2O Water

H2O2 Hydrogen peroxide

In_ Initiator radical

L_

Alkyl radicalL1 Deferiprone

LDPE Low-density polyethylene

LO_ Alkoxyl radical

LOO_ Peroxyl radical

LOOH Lipid hydroperoxides

MAP Modied atmosphere packaging

O2 Oxygen1O2 Singlet oxygen

_OH Hydroxyl radical

OS Oxygen scavenger

PAA Poly(acrylic acid)

PDMS Polydimethylsiloxane

PEG Polyethylene glycolPEI Polyethylenimine

PET Polyethylene terephthalate

PG Propylene glycol

PLA Poly(lactic acid)

PP Polypropylene

PS Polystyrene

PVA Polyvinyl alcohol

TBHQ tert -Butylhydroquinone

TiO2 Titanium dioxide

UV Ultraviolet

Acknowledgements

This work was supported by the United States Department of

Agriculture National Institute of Food and Agriculture

References

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biotechnology ed C C Akoh and D B Min Marcel

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4 J Koontz Controlled Release of Natural Antioxidants from

Polymer Food Packaging by Molecular Encapsulation with

Cyclodextrins Virginia Polytechnic Institute and State

University 2008

5 W Chaiyasit R J Elias D J McClements and E A Decker

Crit Rev Food Sci Nutr 2007 47 299ndash3176 R Wilson C E Fernie C M Scrimgeour K Lyall L Smyth

and R A Riemersma Eur J Clin Invest 2002 32 79ndash83

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Sci Technol 2002 104 439ndash447

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toxicological and health perspectives ed D L Madhavi S

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and J Druzian J Agric Food Chem 2011 59 2248ndash

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Rojas and B Vallejo Cordoba Food Res Int 2009 42 1396ndash

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Springer-Verlag New York 2004

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Technol 2011 46 1289ndash1295

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2012 60 2046ndash2052

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2012 60 7710ndash7718

27 Anonymous Code of federal regulations Washington DC

2005 Title 21 pp 170ndash199

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Food amp Function Review

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Packag Technol Sci 2003 16 15ndash20

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Sci 2003 68 408ndash420

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Structure and function of food engineering ed A A Eissa

InTech 2012 pp 26ndash27

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2013 136 245ndash250

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42 X Shi J Lim and T Ha Anal Chem 2010 82 6132ndash6138

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2007 107 1647ndash1654

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Packag 1997 30 10ndash17

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2011 76 E561ndashE568

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Food Addit Contam 2006 23 1236ndash1241

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27 250ndash255

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54 M Jamshidian E Tehrany M Imran M Akhtar and

F Cleymand J Food Eng 2012 110 380ndash389

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2012 60 3492ndash3497

56 C Lee D An S Lee H Park and D Lee J Food Eng 2004

62 323ndash329

57 C Wessling T Nielsen and A Leufven Packag Technol

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Hydrocolloids 2012 29 290ndash297

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Cienc Rural 2012 42 2085ndash2091

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and D P Dowling Food Sci Technol 2012 47 471ndash477

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J M Cruz Packag Technol Sci 2011 24 353ndash360

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J M Cruz Food Res Int 2010 43 1277ndash1282

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R Gavara P Hernandez-Munoz and P Hernandez

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and P Hernandez Munoz Food Chem 2011 131 1376ndash

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Chem 2007 389 1989ndash1996

71 C Nerin L Tovar and J Salafranca J Food Eng 2008 84

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Postharvest Biol Technol 2011 60 211ndash219

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1216 3731ndash373974 J Camo A Lores D Djenane J Antonio Beltran and

P Roncales Meat Sci 2011 88 174ndash178

75 M Arrieta M Peltzer and A Jimenez J Food Eng 2013

114 486ndash494

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and R Catala Packag Technol Sci 2012 25 457ndash466

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E273ndashE279

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J Agric Food Chem 2012 60 6515ndash6523

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Part A 2009 26 938ndash

94680 S Gemili A Yemenicioglu and S Altinkaya J Food Eng

2010 96 325ndash332

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J Debevere Trends Food Sci Technol 1999 10 77ndash86

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EP1477519 2004

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Review Food amp Function

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8122019 Tian et al 2013

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86 J M Goddard J N Talbert and J H Hotchkiss J Food Sci

2007 72 E36ndashE41

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Nobile J Food Eng 2007 78 741ndash745

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32 698ndash725

89 M D Romero Sanchez M M Pastor Blas J M Martin

Martinez and M J Walzak Int J Adhes Adhes 2005 25

358ndash37090 J Barish and J Goddard J Appl Polym Sci 2011 120

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91 G G Odian Principles of polymerization Wiley-Interscience

publication New York 3rd edn 1991

92 J M Goddard and J H Hotchkiss J Appl Polym Sci 2008

108 2940ndash2949

93 J Barish and J Goddard J Food Sci 2011 76 E586ndashE591

94 N Soares and J Hotchkiss J Food Sci 1998 63 61ndash65

95 A Lopez Rubio E Almenar P Hernandez Munoz

J Lagaron and R Catala Food Rev Int 2004 20 357ndash387

96 B Pan W Zhang L Lv and Q Zhang Chem Eng J 2009

151 19ndash

2997 A Bukowska and W Bukowski J Appl Polym Sci 2012

124 904ndash914

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2012 187 16ndash28

99 S Polomoscanik C Cannon T Neenan S Holmes Farley

and W Mandeville Biomacromolecules 2005 6 2946ndash2953

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A Kolnagou Curr Med Chem 2004 11 2161ndash2183

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C Berkland J Appl Polym Sci 2011 121 1384ndash1392

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R Rijk Food Addit Contam 2005 22 975ndash979

103 S Huang E Frankel K Schwarz and J German J Agric

Food Chem 1996 44 2496ndash2502

104 E A Decker in Food Lipids Chemistry Nutrition and

Biotechnology ed C C Akoh and D B Min Marcel

Dekker New York 2002105 L Bastarrachea S Dhawan and S Sablani Food Eng Rev

2011 3 79ndash93

106 C Lopez de Dicastillo J Alonso R Catala R Gavara and

P Hernandez Munoz J Agric Food Chem 2010 58

10958ndash10964

107 T Goda T Konno M Takai T Moro and K Ishihara

Biomaterials 2006 27 5151ndash5160

108 D Dainellia N Gontardb D Spyropoulos E Zondervan-

van den Beukend and P Tobback Trends Food Sci

Technol 2008 19 S103ndashS112

109 M Aznar A Rodriguez Lafuente P Alfaro and C Nerin

Anal Bioanal Chem 2012 404 1945ndash

1957110 E Hurme T Sipilainen-Malm and R Ahvenainen in

Minimal Processing Technologies in the Food Industry ed

T Ohlsson and N Bengtsson CRC Press Boca Raton Fl

2002

111 J Koontz Inform 2012 23 598ndash600

112 D J Ettinger Active and intelligent packaging A US and

EU perspective 2002 httpwwwpackaginglawcom

2558_shtml

Food amp Function Review

View Article Online