Mechano-responsive composition

Patent metadata

Field	Value
Publication number	US-9868812-B2
Application number	US-201615011934-A
Country	US
Kind code	B2
Filing date	Feb 1, 2016
Priority date	Aug 12, 2013
Publication date	Jan 16, 2018
Grant date	Jan 16, 2018

Abstract

The present invention provides a two-part mechano-responsive composition, comprising: Part I: a tetra-glycidyl amine multifunctional epoxy resin represented by the general formula (I);

and Part II: a polythiol and an amine. The cured composition has a mechano-responsive property without adding any dyes or luminescence agents, and by subjected to mechanical stimuli, the cured composition changes its color, and the color is in the visible spectrum range, which can be easily checked with naked eyes; and the color change is reversible.

First claim

What is claimed is:

1. A two-part mechano-responsive composition, comprising:
Part I: a tetra-glycidyl amine multifunctional epoxy resin represented by the general formula (I);

wherein R1 represents a linear or branched, unsubstituted or substituted alkylene group having 1 to 10 carbon atoms; and
R2, R3, R4 and R5, independently each other, represent a direct bond, a linear or branched, unsubstituted or substituted alkylene group having 1 to 10 carbon atoms, an unsubstituted or substituted arylene group having 6 to 20 carbon atoms, or a combination of the alkylene and the arylene; and
Part II: consisting of a polythiol and a tertiary amine catalyst;

wherein more than 50% of the polythiol carries at least 3 thiol groups per molecule and when cured and subjected to mechanical stimuli, the cured composition changes color.

2. The composition according to claim 1 , wherein the alkylene group of R1 is a linear or branched, unsubstituted alkylene group having 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10 carbon atoms.

3. The composition according to claim 1 , wherein the arylene group is an unsubstituted phenylene, biphenylene or phenylene-biphenylene.

4. The composition according to claim 1 , wherein R1 contains at least one arylene group in the backbone.

5. The composition according to claim 4 , wherein the alkylene group and the arylene group present alternately in the backbone of the R1 group.

6. The composition according to claim 5 , wherein R1 represents

wherein
L represents a linear or branched alkylene group having 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10 carbon atoms, preferably, a linear or branched alkylene group having 1, 2, 3, 4 or 5 carbon atoms, such as, methylene, ethylene, propylene, butylene or amylene;
R represents an alkyl group having 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10 carbon atoms, preferably, an alkyl group having 1, 2 or 3 carbon atoms, such as, methyl, ethyl or propyl; and
n is an integer of 0 to 4, preferably, 0 or 1, more preferably, 0.

7. The composition according to claim 1 , wherein R2, R3, R4 and R5, independently from each other, represent a direct bond, or a linear or branched alkylene group having 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10 carbon atoms.

8. The composition according to claim 1 , wherein more than 70% of the polythiol carries at least three thiol groups per molecule.

9. The composition according to claim 8 , wherein 100% of the polythiol carries at least three thiol groups per molecule.

10. The composition according to claim 1 , wherein the polythiol is selected from trimethylolpropane tris(thioglycolate), pentaerythritol tetrakis(thioglycolate), trimethylolpropane tris(3-mercaptopropionate), pentaerythritol tetrakis(3-mercaptopropionate), and pentaerythritol tetrakis(3-mercaptobutylate).

11. The composition according to claim 1 , wherein the amine is a tertiary amine.

12. A process for producing a mechano-responsive material using the composition according to claim 1 , comprising: blending the tetra-glycidyl amine multifunctional epoxy resin, the polythiol, the amine and optional additives together, and curing the mixture to obtain the mechano-responsive material.

Assignees

• Henkel Ag & Co Kgaa

Inventors

• Wu Haiping
• Zhang Jingfen
• Schoenfeld Rainer
• Bachon Thomas

Classifications

• C08G59/3227

  Compounds containing acyclic nitrogen atoms · CPC title

• C08G59/28 Primary

  containing acyclic nitrogen atoms · CPC title

• C08K5/00

  Use of organic ingredients · CPC title

• C08G59/686

  containing nitrogen · CPC title

• C08G59/66 Primary

  Mercaptans · CPC title