Polyol Ester Plasticizers and Process of Making the Same

a polyol ester and plasticizer technology, applied in the field of triglyceride esters, can solve the problems of cyclohexanoic acid processability, “slow fusion” plasticizers, and special effects, and achieve the effects of reducing toxicity concerns, reducing toxicity, and reducing aging

a polyol ester and plasticizer technology, applied in the field of triglyceride esters, can solve the problems of cyclohexanoic acid processability, “slow fusion” plasticizers, and special effects, and achieve the effects of reducing toxicity concerns, reducing toxicity, and reducing aging

US20110021680A1Inactive Publication Date: 2011-01-27EXXONMOBIL CHEM PAT INC

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  • Polyol Ester Plasticizers and Process of Making the Same
  • Polyol Ester Plasticizers and Process of Making the Same
  • Polyol Ester Plasticizers and Process of Making the Same

Examples

Experimental program
Comparison scheme
Effect test

example 4

[0140]A mixture comprising 100 grams of glycerol tris-isoheptanoate, 0.5 grams stearic acid, 4 grams of epoxidized soybean oil, and 5 grams of the Calcium / Zinc PVC stabilizer Mark 1221 (from Chemtura) was slowly heated to 50° C. on a hot plate, with stirring, until the stearic acid dissolved. The solution was cooled to room temperature, then slowly poured over 200 grams of PVC resin (Oxy 240) and mixed in a Hobart mixer for 5 minutes. The powder mixture was then heated on a room mill, at 165° C. for 5 minutes. The sheets from the roll mill were then compression molded at 171° C., first at 1000 psig, then at 3500 psig. After cooling the sheets were removed for testing.

[0141]The PVC specimens were conditioned for 7 days at 22° C. and 50% relative humidity before testing. The following properties were recorded for the isoC7 triglyceride ester in this PVC formulation: Shore A Hardness (15 sec) 76; tensile strength 3144 psi, elongation 394%, weight loss after 7 days at 100° C. 10.9%, car...

example 5

[0142]A mixture comprising 80 grams of glycerol tris-isoheptanoate, 0.5 grams stearic acid, 4 grams of epoxidized soybean oil, and 5 grams of the Calcium / Zinc PVC stabilizer Mark 1221 (from Chemtura) was slowly heated to 50° C. on a hot plate, with stirring, until the stearic acid dissolved. The solution was cooled to room temperature, then slowly poured over 200 grams of PVC resin (Oxy 240) and mixed in a Hobart mixer for 5 minutes. The powder mixture was then heated on a room mill, at 165° C. for 5 minutes. The sheets from the roll mill were then compression molded at 171 C, first at 1000 psig, then at 3500 psig. After cooling the sheets were removed for testing.

[0143]The PVC specimens were conditioned for 7 days at 22° C. and 50% relative humidity before testing. The following properties were recorded for the isoC7 triglyceride ester in this PVC formulation: Shore A Hardness (15 sec) 86; tensile strength 1968 psi, elongation 353%, Clashberg Tf of −22° C., and Bell Brittleness tem...

example 6

[0144]A mixture comprising 100 grams of glycerol tris-(isoheptanoate / benzoate), 0.5 grams stearic acid, 4 grams of epoxidized soybean oil, and 5 grams of the Calcium / Zinc PVC stabilizer Mark 1221 (from Chemtura) was slowly heated to 50° C. on a hot plate, with stirring, until the stearic acid dissolved. The solution was cooled to room temperature, then slowly poured over 200 grams of PVC resin (Oxy 240) and mixed in a Hobart mixer for 5 minutes. The powder mixture was then heated on a room mill, at 165° C. for 5 minutes. The sheets from the roll mill were then compression molded at 171° C., first at 1000 psig, then at 3500 psig. After cooling the sheets were removed for testing.

[0145]The PVC specimens were conditioned for 7 days at 22° C. and 50% relative humidity before testing. No exudation was observed. The following properties were recorded for the iso C7 triglyceride / benzoate tri ester in this PVC formulation:[0146]Shore A Hardness (15 sec) 74; tensile strength 2982 psi, elonga...

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Abstract

Triglyceride and other polyol ester PVC plasticizers can be produced by recovery of branched C6 to C9 aldehydes from a hydroformylation product, optional hydrogenation to the alcohol, oxidation to the acid with oxygen and / or air, recovery of the resulting acid, and esterification with glycerol, ethylene glycol, propylene glycol or mixtures thereof. The branched alkyl chains comprise at least 10% methyl branching. Special triglycerides are derived from branched aliphatic acids having alkyl chains with average carbon numbers from 6 to 9 and at least 10% methyl branching. These triglycerides are fast fusing plasticisers if before esterification with glycerol, an aryl acid is introduced together with the aliphatic acids.

Description

FIELD OF THE INVENTION[0001]The invention relates to triglyceride esters based on branched alkyl groups, useful as plasticizers and viscosity depressants for a wide range of resins. The invention further relates to a process for producing polyol ester plasticisers from carboxylic acids having branched alkyl chains, obtained by hydroformylation. The polyol esters may also comprise an aromatic acid group.BACKGROUND OF THE INVENTION[0002]Plasticizers are incorporated into a resin (usually a plastic or elastomer) to increase the flexibility, workability, or distensibility of the resin. The largest use of plasticizers is in the production of “plasticized” or flexible polyvinyl chloride (PVC) products. Typical uses of plasticized PVC include films, sheets, tubing, coated fabrics, wire and cable insulation and jacketing, toys, flooring materials such as vinyl sheet flooring or vinyl floor tiles, adhesives, sealants, inks, and medical products such as blood bags and tubing, and the like.[00...

Claims

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Application Information

Patent Timeline
27 Jan 2011
Publication
US20110021680A1
IPC
C08L91/00; C07C69/66; C07C69/76; C07C69/34
CPC
C07B41/12; C07C45/50; C07C51/235; C07C67/08; C07C69/30; C08K5/11; C08K5/103; C08K5/0016
Inventors
COLLE, KARLA S.; BUESS, PHILLIPPE LOUIS