Polymeric Food Antioxidants

Orange, yellow, [14,21,24,27, burgundy, red, 31-34] black, amaranth burgundy 

Other polymeric antioxidants have been prepared by condensation of divinylbenzene with various phenols andhydroquinones such as hydroxyanisole, t-butylphenol. 

Schone 5.5 Preparation of monomeric and polymeric mtileimide antioxidants [43] 

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Polymeric Food Antioxidants Table 5.1 Polymeric food colorants... 

Scheme 5.4 Polymeric food antioxidant of phenol derivative [37-41]...

High-molecular-weight A-substituted maleimides have been prepared and used as polymeric food antioxidants which can achieve the desired gastrointestinal nonabsorption. A-(3,5-Di-t-Bu -hydroxyphenyl)maleimide was prepared in two steps (a) formation of 2,6-di-t-Bu-4-aminophenol either from 2,6-di-(-Bu-phenol by nitration followed by reduction, or from 4-aminophenol by alkylation, (b) amida-tion of maleic anhydride with the 2,6-di-t-Bu-4-aminophenol followed by dehydration. The nonabsorbable poly(A-(3,5-di-t-Bu-4-hydroxyphenyl)maleimide)s were prepared from the monomeric maleimides by free radical homo- and copolymerization with comonomers of alkyl vinyl ethers (Scheme 5.5) [43]. 

Use Polymerization catalyst, antioxidant, and heat stabilizer for PVC (not approved by FDA for food containers), electrically conducting tin oxide coatings, alkaline-earth-metal phosphates in fluorescent light bulbs, intermediate for silicones. 

CAS 6683-19-8 EINECS/ELINCS 229-722-6 Uses Antioxidant for PE, PS, PP, polyacetal, AS resin, methacrylic resin, PC, polyester, polymethylpentene, butadiene resin, polybutene-1, EPM, EPD, PVC stabilizer for org. and polymeric materials antioxidant/stabi-lizer for petrol, prods., syn. rubbers, latex, varnish, adhesives, wire and cable insulation, syn. diester fluids, oils, fats, waxes food-pkg. adhesives, coatings, paper, polymers, rubber, wood preservatives Features Nonstaining, nondiscoloring good extract resist. 

Chem. Descrip. Didodecyl thiodipropionate CAS 123-28-4 EINECS/ELINCS 204-615-1 Uses Antioxidant for polymers, esp. PP, HOPE, LDPE, LLDPE, PS,ABS, PMMA, PA, PET, PBT, PC, POM, PU, in resinous/polymeric food-con-tact coatings preservative in foods antioxidant migrating from food pkg. Regulatory FDA 21CFR 175.300,181.24,182.3280 Properties Wh. powd. m.w. 514.9 m.p. 39-42 C < 0.1% ash Seenox DS [Shipro Kasei Kaisha]... 

Toxicology LD50 (oral, rat) 33 g/kg mildly toxic by ingestion TSCA listed Hazardous Decomp. Prods. Heated to decomp., emits acrid smoke and irritating fumes Uses Antioxidant for plastics, ABS, emulsion polymerization processes antioxidant in food-contact rubber articles for repeated use in food-pkg. adhesives... 

Uses Epoxy accelerator epoxy curing agent, activator for coatings, adhesives, castings, potting, encapsulation PU foam catalyst antioxidant in resinous/polymeric food-contact coatings... 

Chapter 5 describes the use of polymeric food additives such as colorants, antioxidants, nonnutritive sweeteners, nonnutritive hydrocolloids, animal feed additives, as well as indicators and biosensors in foods. Polymeric food additives are to enhance food quality, to preserve and enhance food flavor, taste, and appearance without affecting food nutritional value. They are substances other than basic foodstuffs, which exhibit their functions prior to consumption of the food products, either acting as aids in the manufacture, preservation, coloration, and stabilization of food products, or serving to improve the biological value of certain foods. 

Uses Polymerization inhibitor antioxidant, preservative, stabilizer for foods, pharmaceuticals, industry, polyesters antioxidant in cosmetics inhibitor in food-con-tact crosslinked polyesters... 

On-line SFE-pSFC-FTIR was used to identify extractable components (additives and monomers) from a variety of nylons [392]. SFE-SFC-FID with 100% C02 and methanol-modified scC02 were used to quantitate the amount of residual caprolactam in a PA6/PA6.6 copolymer. Similarly, the more permeable PS showed various additives (Irganox 1076, phosphite AO, stearic acid - ex Zn-stearate - and mineral oil as a melt flow controller) and low-MW linear and cyclic oligomers in relatively mild SCF extraction conditions [392]. Also, antioxidants in PE have been analysed by means of coupling of SFE-SFC with IR detection [121]. Yang [393] has described SFE-SFC-FTIR for the analysis of polar compounds deposited on polymeric matrices, whereas Ikushima et al. [394] monitored the extraction of higher fatty acid esters. Despite the expectations, SFE-SFC-FTIR hyphenation in on-line additive analysis of polymers has not found widespread industrial use. While applications of SFC-FTIR and SFC-MS to the analysis of additives in polymeric matrices are not abundant, these techniques find wide application in the analysis of food and natural product components [395]. 

Uses. A high-production-volume chemical used in manufacture of epoxy-phenolic resins (protective linings for food and beverage cans) monomer for polycarbonate resins (used in food contact materials such as returnable beverage bottles, infant feeding bottles, plates, and mugs) antioxidant in PVC plastics inhibitor of end polymerization in PVC plastics... 

A special type of polymeric antioxidant is anoxomer, which consists of 1,4-benzenediol, 2-(l,l-dimethylethyl)-polymer with diethylbenzene, 4-(l,l-dimethyl-ethyl)phenol, 4-methoxy-phenol, 4,4 -(l-methylethylidene)bis(phenol), and 4-methylphenol prepared by condensation polymerization of divinylbenzene (m- and p-) with tert-butylhydroquinone, tert-butylphenol, hy-droxyanisole, p-cresol, and 4,4 -isopropylidenediphenol. Total monomers, dimers, and trimers below 500 are not more than 1%. Anoxomer is permitted in the United States as an antioxidant in food at a level of not more than 5 ppm of fat and oil content of the food. 

Brownmiller, C. Howard, L.R. Prior, R.L. 2008. Processing and storage effects on monomeric anthocyanins, percent polymeric color, and antioxidant capacity of processed blueberry products. J. Food Sci. 73 H72-H79. 

Proanthocyanidins (PAs) are oligomeric and polymeric flavan-3-ols, better known as condensed tannins. They are ubiquitous and one of the most abundant groups of natural phenols (Porter, 1988). PAs affect the texture, color, and taste of many common foods including cereals, fruits, vegetables, and wines. PAs in foods are also of interest in nutrition and medicine because of their potent antioxidant capacities and beneficial effects on human health in reducing the risk of chronic diseases, such as cardiovascular diseases and cancers (Santos-Buelga and Scalbert, 2000 Prior and Gu, 2005). 

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