Use of functionalized alpha-angelica lactones

Patent metadata

Field	Value
Publication number	US-11697643-B2
Application number	US-202117451165-A
Country	US
Kind code	B2
Filing date	Oct 18, 2021
Priority date	Apr 16, 2019
Publication date	Jul 11, 2023
Grant date	Jul 11, 2023

Abstract

The present invention is directed to the use as a reactive component in the curing of compositions based on epoxy resins of a functionalized α-angelica lactone (XOMAL) having the general formula:wherein: Ra is a C1-C30 alkyl, C3-C30 cycloalkyl, C6-C18 aryl or C2-C12 alkenyl group.

First claim

What is claimed is:

1. A reactive composition comprising:
a) a functionalized α-angelica lactone (XOMAL) having the general formula

wherein R a is a C 1 -C 30 alkyl, C 3 -C 30 cycloalkyl, C 6 -C 18 aryl or C 2 -C 12 alkenyl group; and
b) a curative component comprising at least one of i) and ii):
i) at least one polyamine having at least two amine hydrogens reactive toward epoxide groups; and
ii) at least one mercapto compound having at least two mercapto groups reactive toward epoxide groups.

2. The composition according to claim 1 , wherein said functionalized α-angelica lactone (XOMAL) a) has the general formula:

wherein: R a is a C 1 -C 18 alkyl, C 3 -C 18 cycloalkyl, C 6 -C 18 aryl or C 2 -C 10 alkenyl group.

3. The composition according to claim 1 , wherein substituent R a of said functionalized α-angelica lactone (XOMAL) a) is a C 1 -C 12 alkyl or C 2 -C 8 alkenyl group.

4. The composition according to claim 1 , wherein substituent R a of said functionalized α-angelica lactone (XOMAL) a) is a C 1 -C 4 alkyl or C 2 -C 4 alkenyl group.

5. The composition according to claim 1 , wherein said at least one polyamine b) i) contains primary and/or secondary amine groups and has an equivalent weight per said amine groups of not more than 150.

6. The composition according to claim 1 , wherein said at least one polyamine b) i) comprises an aliphatic amine selected from the group consisting of: isophorone diamine (IPDA); hexamethylene diamine (HMDA); 1,3-bis(amino-methyl)cyclohexane; 1,4-bis(aminomethyl)cyclohexane; bis(4-amino-cyclohexyl)methane; bis(4-amino-3-methylcyclohexyl)methane; 2,5(2,6)-bis(aminomethyl)-bicyclo[2.2.1]heptane (NBDA); and ether group-containing polyamines with an average molecular weight of up to 2000 g/mol.

7. The composition according to claim 1 , wherein said at least one mercapto compound b) ii) is selected from polyesters of thiocarboxylic acids and mixtures of said polyesters.

8. The composition according to claim 7 , wherein said at least one mercapto compound b) ii) is selected from the group consisting of pentaerythritol tetramercapto-acetate (PETMP), trimethylolpropane trimercaptoacetate (TMPMP), glycol dimercaptoacetate and mixtures thereof.

9. A curable composition comprising the reactive composition as defined in claim 1 and c) at least one epoxide compound.

10. The curable composition according to claim 9 , wherein said at least one epoxide compound c) is a polyepoxide selected from the group consisting of: glycidyl ethers of polyhydric alcohols, glycidyl ethers of polyhydric phenols, glycidyl esters of polycarboxylic acids, epoxidized polyethylenically unsaturated hydrocarbons, epoxidized esters, epoxidized ethers, and epoxidized amides.

11. The curable composition according to claim 9 , characterized by a molar ratio of epoxy-reactive groups to epoxy groups from 0.95:1 to 1.5:1.

12. The curable composition according to claim 9 , comprising, based on the weight of the composition: from 10 to 40 wt. % of a); from 20 to 50 wt. % of b); and from 10 to 50 wt. % of c).

13. The curable composition according to claim 12 , wherein:
R a of said functionalized α-angelica lactone (XOMAL) a) is a C 1 -C 4 alkyl or C 2 -C 4 alkenyl group;
said at least one polyamine b) i)
contains primary and/or secondary amine groups and has an equivalent weight per said amine groups of not more than 150;

said at least one mercapto compound b) ii) is
selected from the group consisting of pentaerythritol tetramercapto-acetate (PETMP), trimethylolpropane trimercaptoacetate (TMPMP), glycol dimercaptoacetate and mixtures thereof; and

said at least one epoxide compound c) is
selected from the group consisting of: glycidyl ethers of polyhydric alcohols, glycidyl ethers of polyhydric phenols, and glycidyl esters of polycarboxylic acids.

14. A cured product obtained by curing the composition as defined in claim 9 .

Assignees

• Henkel Ag & Co Kgaa

Inventors

• Ito Kenji
• Taden Andreas

Classifications

• C08G59/66

  Mercaptans · CPC title

• C07D307/58 Primary

  One oxygen atom, e.g. butenolide · CPC title

• C08G59/063

  with epihalohydrins · CPC title

• C08G59/56

  together with other curing agents · CPC title

• C08G59/626 Primary

  Lactones · CPC title