Plasticizer composition containing furan derivatives and 1,2-cyclohexanedicarboxylic ester

Patent metadata

Field	Value
Publication number	US-10072133-B2
Application number	US-201515109861-A
Country	US
Kind code	B2
Filing date	Jan 8, 2015
Priority date	Jan 9, 2014
Publication date	Sep 11, 2018
Grant date	Sep 11, 2018

Abstract

The present invention relates to a plasticizer composition which comprises at least one furan derivative and at least one 1,2-cyclohexanedicarboxylate ester, molding compounds which comprise a thermoplastic polymer or an elastomer and such a plasticizer composition and the use of these plasticizer compositions and molding compounds.

First claim

The invention claimed is:

1. A plasticizer composition comprising
a) at least one compound of the general formula (I),

wherein
X is *—(C═O)—O—, *—(CH 2 ) n —O— or *—(CH 2 ) n —O—(C═O)—, wherein * represents the linkage point with the furan ring and n has the value 0, 1 or 2;
and
R 1 and R 2 are mutually independently selected from C 4 alkyl and C 5 -C 6 cycloalkyl, wherein the cycloalkyl residues are unsubstituted or can be substituted with at least one C 1 -C 10 alkyl residue,
b) at least one compound of the general formula (II),

wherein
R 3 and R 4 are mutually independently selected from branched and unbranched C 7 -C 12 alkyl residues and
wherein the content of the compounds of the general formula (I) in the plasticizer composition is 1 to 50 wt. % and
the content of the compounds of the general formula (II) in the plasticizer composition is 10 to 99 wt. %.

2. The plasticizer composition as claimed in claim 1 , wherein R 1 and R 2 mutually independently are an unbranched or branched C 4 alkyl residue.

3. The plasticizer composition as claimed in claim 1 , wherein R 1 and R 2 both are n-butyl or both are isobutyl.

4. The plasticizer composition as claimed in claim 1 , wherein X is *—(C═O)—O—.

5. The plasticizer composition as claimed in claim 1 , wherein R 3 and R 4 both are 2-ethylhexyl, both are isononyl or both are 2-propylheptyl.

6. The plasticizer composition as claimed in claim 1 , wherein the plasticizer composition further comprises a plasticizer different from the compounds (I) and (II), which is selected from the group consisting of dialkyl phthalate esters, alkyl aralkyl phthalate esters, 1,2-cyclohexanedicarboxylate esters different from compounds (II), dialkyl terephthalate esters, trialkyl trimellitate esters, alkyl benzoate esters, dibenzoate esters of glycols, hydroxybenzoate esters, esters of saturated mono- and dicarboxylic acids, esters of unsaturated dicarboxylic acids, amides and esters of aromatic sulfonic acids, alkylsulfonate esters, glycerin esters, isosorbide esters, phosphate esters, citric acid triesters, alkylpyrrolidone derivatives, 2,5-furandicarboxylate esters different from compounds (I), 2,5-tetrahydrofurandicarboxylate esters, epoxidized plant oils and epoxidized fatty acid monoalkyl esters, and polyesters of aliphatic and/or aromatic polycarboxylic acids with at least dihydric alcohols.

7. The plasticizer composition as claimed in claim 1 , wherein the weight ratio between compounds of the general formula (I) and compounds of the general formula (II) is in the range from 1:100 to 1:1.

8. A molding compound comprising at least one polymer and one plasticizer composition as defined in claim 1 .

9. The molding compound as claimed in claim 8 , wherein the polymer is a thermoplastic polymer which is selected from
homo- or copolymers which comprise at least monomer incorporated by polymerization, which is selected from C 2 -C 10 monoolefins, 1,3-butadiene, 2-chloro-1,3-butadiene, vinyl alcohol and C 2 -C 10 alkyl esters thereof, vinyl chloride, vinylidene chloride, vinylidene fluoride, tetrafluoroethylene, glycidyl acrylate, glycidyl methacrylate, acrylates and methacrylates of C 1 -C 10 alcohols, vinylaromatics (meth)acrylonitrile, maleic anhydride and α,β-ethylenically unsaturated mono- and dicarboxylic acids,
homo- and copolymers of vinyl acetals,
polyvinyl esters,
polycarbonates,
polyesters,
polyethers,
polyether ketones,
thermoplastic polyurethanes,
polysulfides,
polysulfones,
polyether sulfones,
cellulose alkyl esters,
and mixtures thereof.

10. The molding compound as claimed in claim 9 , wherein the thermoplastic polymer is selected from polyvinyl chloride (PVC), polyvinyl butyral (PVB), homo- and copolymers of vinyl acetate, homo- and copolymers of styrene, polyacrylates, thermoplastic polyurethanes (TPU) or polysulfides.

11. The molding compound as claimed in claim 9 , where the thermoplastic polymer is polyvinyl chloride (PVC).

12. The molding compound as claimed in claim 11 , where the content of the plasticizer composition in the molding compound is 1.0 to 300 phr.

13. The molding compound as claimed in claim 9 , comprising at least one thermoplastic polymer different from polyvinyl chloride, where the content of the plasticizer composition in the molding compound is 0.5 to 300 phr.

14. The molding compound as claimed in claim 8 , where the polymer is an elastomer.

15. The molding compound as claimed in claim 8 , where the polymer is natural rubber, synthetic rubber or a mixture thereof.

16. The molding compound as claimed in claim 14 , wherein the content of the plasticizer composition in the molding compound is 1.0 to 60 phr.

17. A process for the production of molded articles and films which comprises utilizing the plasticizer composition as claimed in claim 1 .

18. The molded articles or film produced by the process of claim 17 , which come directly into contact with people or foods are medicinal products, hygiene products, food packaging, products for interiors, toys and childcare articles, sport and leisure products, clothing or fibers for fabrics.

Assignees

• Basf Se

Inventors

• Wagner Jochen
• Breitscheidel Boris
• Bohn Martin A
• Blank Benoit
• Kindler Alois

Classifications

• C08K5/12

  of cyclic polycarboxylic acids · CPC title

• C08J3/18 Primary

  Plasticising macromolecular compounds (plasticisers C08K) · CPC title

• C08K5/1535 Primary

  Five-membered rings · CPC title

• C08K5/0016 Primary

  Plasticisers · CPC title

• C08L21/00

  Compositions of unspecified rubbers · CPC title