Plasticiser compositions comprising gelification accelerators based on ester(s) of 1,4 : 3,6-dianhydrohexitol having low molar weight

Patent metadata

Field	Value
Publication number	US-10005894-B2
Application number	US-201314397968-A
Country	US
Kind code	B2
Filing date	May 2, 2013
Priority date	May 3, 2012
Publication date	Jun 26, 2018
Grant date	Jun 26, 2018

Abstract

Disclosed is a composition that can rapidly plasticize polymers, including, in relation to the total mass of (A) and (B): between 0.1 and 99 mass-% of at least one ester of 1,4:3,6-dianhydrohexitol (A), having a molar mass varying between 255 and 345 g·mol −1 and selected from among monoesters and diesters of isosorbide, isomannide and isoidide; and between 1 and 99.9 mass-% of at least one compound (B) having a molar mass greater than 345 g·mol −1 and selected from among the esters of 1,4:3,6-dianhydrohexitol, the esters of cyclohexane polycarboxylic acid, the esters of phthalic acid, and glycerol esters. Also disclosed is a method for the production of a plasticized object using constituents (A) and (B), as well as to the use of the ester compound (A) as a polymer gelification accelerator.

First claim

The invention claimed is:

1. A composition comprising A and B, wherein A ranges from 0.5% to 50% of a total weight of A and B, and A is of at least one 1,4:3,6-dianhydrohexitol ester with a molecular weight of 255 to 345 g/mol, selected from a group consisting of isosorbide, isomannide and isoidide monoesters and diesters; and
B is from 50% to 95.5% by weight with a molecular weight greater than 345 g/mol, selected from a group consisting of esters of cyclohexanepolycarboxylic acid, esters of phthalic acid, esters of 1,4:3,6-dianhydrohexitol and glycerol esters.

2. The composition as claimed in claim 1 , in which the 1,4:3,6-dianhydrohexitol ester is an ester of an acid of from 2 to 8 carbon atoms, with the proviso that when the at least one ester is a diester of the same acid, the acid contains from 2 to 5 carbon atoms.

3. The composition as claimed in claim 1 , in which the 1,4:3,6-dianhydrohexitol ester A is an alkyl ester.

4. The composition as claimed in claim 1 , in which A is selected from a group consisting of 1,4:3,6-dianhydrohexitol dipropionates, 1,4:3,6-dianhydrohexitol dibutyrates, 1,4:3,6-dianhydrohexitol diisobutyrates, 1,4:3,6-dianhydrohexitol divalerates, 1,4:3,6-dianhydrohexitol diisovalerates, 1,4:3,6-dianhydrohexitol dihexanoates, 1,4:3,6-dianhydrohexitol propionates butyrates, 1,4:3,6-dianhydrohexitol propionates isobutyrates, 1,4:3,6-dianhydrohexitol propionates valerates, 1,4:3,6-dianhydrohexitol propionates isovalerates, 1,4:3,6-dianhydrohexitol propionates hexanoates, 1,4:3,6-dianhydrohexitol butyrates isobutyrates, 1,4:3,6-dianhydrohexitol butyrates valerates, 1,4:3,6-dianhydrohexitol butyrates isovalerates, 1,4:3,6-dianhydrohexitol butyrates hexanoates, 1,4:3,6-dianhydrohexitol isobutyrates valerates, 1,4:3,6-dianhydrohexitol isobutyrates isovalerates, 1,4:3,6-dianhydrohexitol isobutyrates hexanoates, 1,4:3,6-dianhydrohexitol valerates hexanoates and 1,4:3,6-dianhydrohexitol isovalerates hexanoates.

5. The composition as claimed in claim 1 , in which A is a 1,4:3,6-dianhydrohexitol divalerate or a 1,4:3,6-dianhydrohexitol dihexanoate.

6. The composition as claimed in claim 1 , in which A is an isosorbide ester.

7. The composition as claimed in claim 1 , in which B is an ester of cyclohexanepolycarboxylic acid.

8. The composition as claimed in claim 1 , in which B is an isosorbide diester with a at least one C 6 -C 12 alkyl group.

9. A polymer paste comprising a blend of a polymer powder and the composition as claimed in claim 1 .

10. A method for plasticizing a polymer comprising blending the composition as claimed in claim 1 with the polymer.

11. The paste as claimed in claim 9 , in which the polymer is selected from a group consisting of polyvinyl chloride, polyurethanes, polyesters, cellulose polymers, starches, acrylic polymers, polyacetates, polyamides, and mixtures thereof.

12. The method as claimed in claim 10 , in which the polymer is selected from a group consisting of polyvinyl chloride, polyurethanes, polyesters, cellulose polymers, starches, acrylic polymers, polyacetates, polyamides, and mixtures thereof.

13. A process for manufacturing an object comprising a polymer C and the composition comprising A and B as claimed in claim 1 , said process comprising:
selecting A, B and the polymer C;
introducing A, B and the polymer C into a mixer system, wherein A accelerates gelling and is added at a wt. % of between 1% to 25% of a total weight of A and B;
mixing A, B and the polymer C to provide a blend;
heating the blend;
shaping the blend into a form of an object; and
recovering the object,
wherein A, B and the polymer C are introduced into a mixer system separately or via a mixture thereof, and simultaneously or sequentially; and
the mixing and heating are carried out simultaneously or sequentially.

14. The process as claimed in claim 13 , in which the mixing is thermomechanical mixing, and the mixer system is a mixer for thermoplastics, selected from a group consisting of a kneader, a Buss mixer, an open mill, and an extruder.

15. The process as claimed in claim 13 , in which the shaping is a calendering stage.

16. The process as claimed in claim 13 , wherein
the mixing A, B and the polymer C to provide a blend is to provide a polymer paste;
the heating provides curing of the blend;
the shaping the blend into a form of an object comprises coating, dipping, slushing or rotationally molding this polymer paste to form a preformed object.

17. The process as claimed in claim 16 , wherein the shaping is coating on a support.

18. The process as claimed in claim 17 , wherein the polymer is selected from a group consisting of polyvinyl chloride, polyurethanes, polyesters, cellulose polymers, starches, acrylic polymers, polyacetates, polyamides, and mixtures thereof.

19. The process as claimed in claim 13 , wherein the sum of A and B ranges from 1 to 900 parts per 100 parts of polymer C by weight.

20. A method for accelerating the gelling of a blend comprising a polymer and a plasticizer, comprising adding to the blend ranges from 1% to 25% by weight of a 1,4:3,6-dianhydrohexitol ester relative to a total weight of said plasticizer and said ester, the molar mass of said ester which ranges from 255 to 345 g·mol −1 , selected from a group consisting of isosorbide, isomannide and isoidide monoesters and diesters.

21. The composition as claimed in claim 1 , in which A ranges from 1% to 25% of the total weight of A and B.

22. The composition as claimed in claim 21 , in which A ranges from 4% to 19% of the total weight of A and B.

23. The composition as claimed in claim 1 , in which A ranges from 2% to 20% of the total weight of A and B.

24. The paste as claimed in claim 9 , in which the polymer is polyvinyl chloride.

25. The method as claimed in claim 10 , in which the polymer is polyvinyl chloride.

26. The process as claimed in claim 17 , wherein the polymer is polyvinyl chloride.

27. The process as claimed in claim 13 , wherein the sum of A and B ranges from 10 to 120 parts per 100 parts of polymer C by weight.

Assignees

• Feron Thierry
• Sobocinski Monique
• Wyart Herve
• Breitscheidel Boris
• Wagner Jochen
• Roquette Freres

Inventors

• Feron Thierry
• Sobocinski Monique
• Wyart Herve
• Breitscheidel Boris
• Wagner Jochen

Classifications

• C08K5/12

  of cyclic polycarboxylic acids · CPC title

• C08L27/06

  Homopolymers or copolymers of vinyl chloride · CPC title

• C09D127/06

  Homopolymers or copolymers of vinyl chloride · CPC title

• C08K5/11

  of acyclic polycarboxylic acids · CPC title

• C08K5/0016

  Plasticisers · CPC title