Mixture of succinic esters as plasticizer

Patent metadata

Field	Value
Publication number	US-9353244-B2
Application number	US-201214008425-A
Country	US
Kind code	B2
Filing date	Feb 27, 2012
Priority date	Mar 31, 2011
Publication date	May 31, 2016
Grant date	May 31, 2016

Abstract

Mixture of succinic esters, which is characterized in that the alkyl radical has a proportion of alkyl components having less than 9 carbon atoms of not more than 15% by mass, the alkyl radical has a proportion of alkyl components having more than 9 carbon atoms of not more than 25% by mass and the proportion of 3,5,5-trimethylhexyl radicals is not more than 5 mol % and the proportion of linear n-nonyl radicals is not more than 15 mol %.

First claim

The invention claimed is:

1. A mixture of succinate esters, comprising at least 60 wt % of C9 diesters, based on 100 weight % of the mixture,
wherein
an alkyl residue has a proportion of alkyl components with less than 9 carbon atoms of a maximum of 15 wt %,
an alkyl residue has a proportion of alkyl components with more than 9 carbon atoms of a maximum of 25 wt %,
a proportion of 3,5,5-trimethylhexyl residues is a maximum of 5 mol %, and
a proportion of linear n-nonyl residues is a maximum of 15 mol %.

2. The mixture as claimed in claim 1 , wherein a proportion of succinic acid relative to all parts of succinic acid that are present in the mixture as ester, which is based on renewable raw materials, is at least 10 mol %.

3. The mixture of claim 1 , wherein a proportion of succinate esters that comprise 3,5,5-trimethylhexyl residue is a maximum of 5 mol %.

4. The mixture of claim 1 , wherein the mixture comprises a proportion of alkyl residues with 9 carbon atoms, which have a methyl branching on a second carbon atom after an oxygen of a carboxyl group, of a maximum of 49.5 mol %.

5. The mixture of claim 1 , wherein the boiling point is above 180° C.

6. The mixture of claim 1 , wherein an intrinsic viscosity determined by shear rheometry with a shear rate of Vs at a temperature of 20° C. is a maximum of 40 mPa·s.

7. A mixture of succinate esters, comprising at least 60 wt % of C9 diesters, based on 100 weight % of the mixture,
wherein
an alcohol mixture for preparation has a proportion of alcohol components with less than 9 carbon atoms of a maximum of 15 wt %, and a proportion of alcohol components with more than 9 carbon atoms of a maximum of 25 wt %,
a content of 3,5,5-trimethylhexanol in the alcohol mixture is a maximum of 5 mol %, and
a content of linear n-nonanol in the alcohol mixture is a maximum of 15 mol %.

8. The mixture of claim 7 , wherein a proportion of succinic acid or succinic acid derivative for production of the esters, which is based on renewable raw materials, is at least 10 mol %.

9. The mixture of claim 7 , wherein a proportion of succinate esters comprising a 3,5,5-trimethylhexyl residue is a maximum of 5 mol %.

10. The mixture of claim 7 , wherein the alcohol mixture comprises a proportion of isomeric alcohols with 9 carbon atoms that have a methyl branching on the β-carbon atom of the alcohol of a maximum of 49.5 mol %.

11. The mixture of claim 7 , wherein the alcohol mixture comprises a proportion of isomeric alcohols with 9 carbon atoms that have two methyl branchings of a maximum of 49.5 mol %.

12. A method of producing the mixture of claim 1 , comprising contacting a succinic acid or succinic acid derivative with an isomeric alcohol mixture, with liberation of water or methanol;
wherein up to 50% stoichiometric excess of the alcohol mixture is used; and

the reaction takes place in the presence of a catalyst selected from the group consisting of butyl titanate, and nonyl titanate.

13. The method of claim 12 , wherein a proportion of succinic acid or succinic acid derivative for production of the esters, which is based on renewable raw materials, is at least 10 mol %.

14. A composition comprising the mixture of claim 1 and a further polymer.

15. The composition of claim 14 , wherein the composition additionally comprises at least one plasticizer selected from the group consisting of alkyl benzoate, dialkyladipate, glycerol ester, trialkyl citrate, acylated trialkyl citrate, trialkyl trimellitate, glycol dibenzoate, dialkyl terephthalate, dialkyl phthalate, dialkanoyl ester of isosorbide, and dialkylester of 1,2-, 1,3- or 1,4-cyclohexane dicarboxylic acids.

16. The mixture of claim 1 , wherein the mixture is suitable as plasticizer.

17. A molded article comprising the mixture of claim 1 .

18. A floor covering comprising the mixture of claim 1 .

19. A wall covering comprising the mixture of claim 1 .

20. A resist, sealant or adhesive comprising the mixture of claim 1 .

21. A film or awning comprising the mixture of claim 1 .

Assignees

• Becker Hinnerk Gordon
• GRAβ MICHAEL
• Evonik Degussa Gmbh

Inventors

• Becker Hinnerk Gordon
• GRAβ MICHAEL

Classifications

• C10M129/72

  of polycarboxylic acids · CPC title

• C07C69/40

  Succinic acid esters · CPC title

• C08K5/10

  Esters; Ether-esters · CPC title

• C10M105/36

  of polycarboxylic acids · CPC title

• C08K5/11 Primary

  of acyclic polycarboxylic acids · CPC title