Glycol adipate

Raw Materials. PVC is inherently a hard and brittle material and very sensitive to heat it thus must be modified with a variety of plasticizers, stabilizers, and other processing aids to form heat-stable flexible or semiflexible products or with lesser amounts of these processing aids for the manufacture of rigid products (see Vinyl polymers, vinyl chloride polymers). Plasticizer levels used to produce the desired softness and flexibihty in a finished product vary between 25 parts per hundred (pph) parts of PVC for flooring products to about 80—100 pph for apparel products (245). Numerous plasticizers (qv) are commercially available for PVC, although dioctyl phthalate (DOP) is by far the most widely used in industrial appHcations due to its excellent properties and low cost. For example, phosphates provide improved flame resistance, adipate esters enhance low temperature flexibihty, polymeric plasticizers such as glycol adipates and azelates improve the migration resistance, and phthalate esters provide compatibiUty and flexibihty (245). 

In the 1940s ICI introduced a material marketed as Vulcaprene made by condensing ethylene glycol, adipic acid and ethanolamine to a molecular weight of about 5000 and then chain extending this with a diisocyanate. This rubbery material found some use as a leathercloth and is dealt with further in Chapter 25. 

Butoxyethanol Poly(diethylene glycol adipate), [Acid end group] = 2.52 meq g ... 

For gas chromatographic analysis of the products, the submitter used a 3 ft. x 0.125 in. stainless steel column of 5% LAC-446 (cross-linked diethylene glycol-adipic ester) on Diatoport S (60-80 mesh), which was heated at 140° and swept with prepurified nitrogen at 30 ml. per minute. The four isomers were observed as three peaks at retention times of 3.08, 3.69, and 4.07 minutes. The checkers used aim. x 4 mm. glass column of 10% DECS on Gas Chrome Q (60-80 mesh), which was heated at 200° and swept with prepurified nitrogen at 75 ml. per minute. 

A second series of non-LC diols was amorphous glycol adipates 3a-3g. These were also prepared by Shotten-Baumann oligomerization ... 

Methanol Formaldehyde Ethylene Propylene oxide Phenol 1,4-Butanediol Tetrahydrofuran Ethylene glycol Adipic acid Isocyanates Styrene Methyl methacrylate Methyl formate Two-step, via CH4 steam reforming Three-step, via methanol Cracking of naphtha Co-product with t-butyl alcohol or styrene Co-product with acetone Reppe acetylene chemistry Multi-step Hydration of ethylene oxide Multi-step Phosgene chemistry Co-product with propylene oxide Two-step, via methacrolein Three-step, via methanol... 

Fig. 2. Reactivity of aromatic diisocyanates 0.02 M with 2-ethyihexanol 0.4 M and diethylene glycol adipate polyester in benzene at 28°C. (A) l-Chloro-2,4-phenylene diisocyanate. (B) m-Phenylene diisocyanate. (C) p-Phenylene diisocyanate. (D) 4,4 -Methylene bis(phenyl isocyanate). (E) 2,4-Tolylene diisocyanate. (F) Tolylene diisocyanate (60%, 2,4-isomer, 40% 2,6-isomer). (G) 2,6-Tolylene diisocyanate. (H) 3,3 -Dimethyl-4,4 -biphenylene diisocyanate (0.002 M) in 0.04 M 2-ethylhexanol. (I) 4,4 -Methylene bis(2-methylphenyl isocyanate). (J) 3,3 -Dimethoxy-4,4 -biphenylene diisocyanate. (K) 2,2,5,5 -Tetramethyl-4,4 -biphenylene diisocyanate. (L) 80% 2,4- and 20% 2,6-isomer of tolylene diisocyanate with diethylene glycol adipate polyester (hydroxyl No. 57, acid No. 1.6, and average molecular weight 1900). Reprinted from M. E. Bailey, V. Kirss, and R. G. Spaunburgh, Ind. Eng. Chem. 48, 794 (1956). (Copyright 1956 by the American Chemical Society. Reprinted by permission of the copyright owner.)...

Diethylene glycol adipate Methyl esters of fatty acids up to C24... 

Adamantane 2 (0.03 mol) and SF4 (0.2 mol) were reacted in a stainless steel autoclave in a conventional manner. The obtained solid mixture of fluoroadamanlanes was purified by sublimation then separated by preparative GC (10 mm x 5 m column, 25% polyethylene glycol adipate on Spherochroine. 0.2 0.5 mm). 

Ethyl phthalyl ethyl glycolate Butyl phthalyl butyl glycolate Adipates Dioctyl... 

Poly(dlethylene glycol adipate) OH 400-2000 0-1.8 silica gel methylethyl ketone (i) LC ... 

Poly(butylene glycol adipate) OH 1000-4000 0-2 silica gel benzene — ethanol, 75/25 (i) TLC 41)... 

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