Mixed-terminated polyester plasticizers

• US 4,122,057 A
• Filed: 04/05/1976
• Issued: 10/24/1978
• Est. Priority Date: 09/03/1974
• Status: Expired due to Term

• Current Assignee: Henkel Corporation (Henkel AG & Co KGaA)
• Original Assignee: Emery Industries, Inc.
• Inventors: Beimesch, Bruce J., Lamont, James, Aylesworth, Robert D.
• Primary Examiner(s): Lieberman, Allan
• Application Number:
  US05/673,570
• Time in Patent Office: 932 Days
• Field of Search: 260/31.6, 260/485 G, 260/475 P, 560/199, 560/90
• US Class Current: 524/311
• CPC Class Codes: C08G 63/20 Polyesters having been prepared in the presence of compounds having one reactive group or more than two reactive groups
• CPC Class Codes: C08L 2666/14 Macromolecular compounds according to C08L59/00 - C08L87/00; Derivatives thereof
• CPC Class Codes: C08L 27/06 Homopolymers or copolymers of vinyl chloride
• CPC Class Codes: C08L 67/02 Polyesters derived from dicarboxylic acids and dihydroxy compounds C08L67/06 takes precedence

Abstract

Polyester plasticizers having improved low temperature properties are obtained by terminating the polyester with mixed chain-terminating agents. Mixtures of monobasic acids and monofunctional alcohols are employed for this purpose. The polyesters of this invention find particular utility as plasticizers for PVC homopolymers and copolymers.

Claims

1. A mixed-terminated polyester plasticizer characterized by having improved low temperature properties and having an average molecular weight between 500 and 5000, an acid value less than 10, hydroxyl value less than 20 and corresponding to the formula ##STR3## wherein R is a bivalent hydrocarbon radical containing from 2 to 6 carbon atoms, R₁ is a bivalent hydrocarbon radical containing from 2 to 10 carbon atoms, T'"'"' is an acyl radical containing 4 to 18 carbon atoms, T" is an alkyl radical containing from 4 to 18 carbon atoms, n is a positive integer from 1 to 9 and consisting essentially of the reaction product of 2 to 10 moles of (a) an aliphatic glycol containing 2 to 6 carbon atoms, with an equimolar amount of (b) an aliphatic dibasic acid containing 4 to 12 carbon atoms or a mixture of C₄ -C₁₂ aliphatic dibasic acid and aromatic dibasic acid or anhydride thereof, and terminated with (c) a mixture of an aliphatic monobasic acid containing 4 to 18 carbon atoms and an aliphatic monofunctional alcohol containing 4 to 18 carbon atoms, the molar ratio of said monobasic and monofunctional alcohol in the mixture ranging between 0.5:

1.5 and 1.5;

0.5.

2. The mixed-terminated polyester plasticizer of claim 1 wherein the average molecular weight is between 600 and 2500 and (c) is a mixture of a C_8-18 monobasic acid and C_6-12 monofunctional alcohol.

3. The mixed-terminated polyester plasticizer of claim 2 wherein (a) is 1,2-propylene glycol, 1,3-butylene glycol or 1,4-butanediol and (b) is adipic acid or azelaic acid.

4. The mixed-terminated polyester plasticizer of claim 3 wherein the molar ratio of monobasic acid to monofunctional alcohol is about 1:

1.

5. The mixed-terminated polyester plasticizer of claim 3 wherein (c) is a mixture of pelargonic acid and 2-ethylhexanol.

6. The mixed-terminated polyester plasticizer of claim 3 wherein (c) is a mixture of lauric acid and 2-ethylhexanol.

7. The mixed-terminated polyester plasticizer of claim 1 having an average molecular weight from about 600 to 2500.

8. The mixed-terminated polyester plasticizer of claim 7 wherein R₁ contains from 4 to 8 carbon atoms, T'"'"' contains from 8 to 18 carbon atoms and T" contains from 6 to 12 carbon atoms.

9. A plasticized vinyl resin composition comprising a polyvinyl chloride homopolymer or copolymer and 10 to 110 parts, per 100 parts resin, of a mixed-terminal polyester plasticizer corresponding essentially to the formula ##STR4## wherein R is a bivalent hydrocarbon radical containing from 2 to 6 carbon atoms, R₁ is a bivalent hydrocarbon radical containing from 2 to 10 carbon atoms, T'"'"' is an acyl radical containing 4 to 18 carbon atoms, T" is an alkyl radical having from 4 to 18 carbon atoms, n is a positive integer from 1 to 9 and consisting essentially of the reaction product of 2 to 10 moles of (a) an aliphatic glycol containing 2 to 6 carbon atoms, with an equimolar amount of (b) an aliphatic dibasic acid containing 4 to 12 carbon atoms or a mixture of C₄ -C₁₂ aliphatic dibasic acid and aromatic dibasic acid or anhydride thereof, and terminated with (c) a mixture of an aliphatic monobasic acid containing 4 to 18 carbon atoms and an aliphatic monofunctional alcohol containing 4 to 18 carbon atoms, the molar ratio of said monobasic acid and monofunctional alcohol in the mixture ranging between 0.5:

1.5 and 1.5;

0.5.