IP Library Granted Patent US 12,049,531
Granted Patent B2
US 12,049,531 · App. 17/370,294 · Granted Jul 30, 2024

Curable compositions for production of reaction induced phase separated compositions with improved properties

Inventors: Bahram Issari (Glastonbury, CT); Michael Paul Levandoski (Terryville, CT); Christina Despotopoulou (Minneapolis, MN); Tianzhi Zhang (Skillman, NJ); Darel Gustafson (Shelton, CT); Robert P. Cross (Rocky Hill, CT)
Assignee: Henkel AG & Co. KGaA
C08F290/068C08F120/32C08G77/16C08G77/20C08G77/38
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Quick Facts
Patent No.
US 12,049,531
App. No.
17/370,294
Granted
Jul 30, 2024
Kind
B2
Abstract

Curable compositions that undergo reaction induced phase separation of domains in cured matrix and provide beneficial physical and chemical properties and methods of use of such compositions. Curable compositions that undergo reaction induced phase separation of domains in cured matrix in response to a first set of curing conditions and the domains undergo a second reaction in response to a second set of curing conditions to improve the physical properties of the domains and the cured composition, such as improvements in glass transition temperature and thermal degradation.

Claims (32)

1. A curable composition comprising a mixture of:

a) a continuous matrix forming component comprising at least two acrylate moieties and having a molecular weight of about 500 daltons or greater,

b) a domain forming component having the formula:

MA-R-Z

wherein MA is a (meth)acrylate, R is a C 1-8 alkylene, and Z is an oxirane group or an oxetane group, and

c) a domain forming co-component;

wherein the curable composition can undergo reaction induced phase separation to produce domains of a polymer of the domain forming component within a continuous matrix of a polymer of the continuous matrix forming component upon exposure to a first set of curing conditions that promotes curing of the acrylate moieties.

2. The curable composition of claim 1 , wherein the continuous matrix forming component is selected from the group consisting of silicones, polyacrylates, polyisobutylenes, polyethers, hydrogenated polybutadienes, polyesters, and combinations thereof.

3. The curable composition of claim 1 , wherein the continuous matrix forming component is a diemethoxy endcapped polydimethyl siloxane.

4. The curable composition of claim 1 , wherein the continuous matrix forming component is present in the curable composition in an amount of about 40% to about 95% by weight based on the total weight of the curable composition; and/or the domain forming component is present in the curable composition in an amount of about 5% to about 60% by weight based on the total weight of the curable composition.

5. The curable composition of claim 1 , wherein the continuous matrix forming monomer is present in the curable composition in an amount of about 55% to about 75% by weight based on the total weight of the curable composition; and/or the domain forming component is present in the curable composition in an amount of about 25% to about 45% by weight based on the total weight of the curable composition.

6. The curable composition of claim 1 , wherein the domain forming component is glycidyl methacrylate.

7. The curable composition of claim 1 , wherein the domain forming co-component is selected from the group consisting of organic acids, an organic primary amines, organic secondary amines, amides, imidazoles, mercaptans, sulfides, and combinations thereof.

8. The curable composition of claim 1 , wherein the domain forming co-component is a carboxylic acid.

9. The curable composition of claim 1 , wherein the domain forming co-component is acrylic acid.

10. The curable composition of claim 1 , wherein the ratio of the domain forming co-component and the domain forming component is a ratio between about 1:99 and about 1:1.

11. The curable composition of claim 1 , further comprising a first cure catalyst.

12. The curable composition of claim 11 , wherein the first cure catalyst is a photoinitiator.

13. The curable composition of claim 11 , wherein the first cure catalyst is present in the curable composition in an amount of about 0.05% to about 8% by weight based on the total weight of the curable composition.

14. The curable composition of claim 1 , wherein the first set of curing conditions comprises exposure to light.

15. The curable composition of claim 1 , wherein the combination of the domain forming component and the domain forming co-component is curable via an epoxy cure reaction and a second set of curing conditions promotes the epoxy cure reaction.

16. The curable composition of claim 15 , wherein the second set of curing conditions comprises heat.

17. A method of producing a dual-phase, cured composition comprising:

a) providing a curable composition comprising a mixture of:

i) a continuous matrix forming component comprising at least two acrylate moieties and having a molecular weight of about 500 daltons or greater,

ii) a domain forming component having the formula:

MA-R-Z

wherein MA is a (meth)acrylate, R is a C 1-8 alkylene, and Z is an oxirane group or an oxetane group, and

iii) a domain forming co-component;

b) exposing the curable composition to a first set of curing conditions to induce reaction induced phase separation to produce an intermediate cured composition having domains of a polymer of the domain forming component within a continuous matrix of a polymer of the continuous matrix forming component,

c) exposing the intermediate cured composition to a second set of curing conditions to induce additional curing of the domains of the polymer of the domain forming component to obtain a dual-phase, cured composition.

18. A dual-phase, cured composition produced by the method of claim 17 .

Assignments (7)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 27, 2022
From: LEVANDOSKI, MICHAEL PAUL
To: HENKEL IP & HOLDING GMBH
Reel/Frame 061223/0522 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 27, 2022
From: DESPOTOPOULOU, CHRISTINA
To: HENKEL AG & CO. KGAA
Reel/Frame 061223/0607 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 27, 2022
From: ISSARI, BAHRAM
To: HENKEL IP & HOLDING GMBH
Reel/Frame 061223/0694 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 27, 2022
From: ZHANG, TIANZHI
To: HENKEL IP & HOLDING GMBH
Reel/Frame 061223/0808 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 27, 2022
From: GUSTAFSON, DAREL
To: HENKEL IP & HOLDING GMBH
Reel/Frame 061223/0892 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 27, 2022
From: CROSS, ROBERT P.
To: HENKEL IP & HOLDING GMBH
Reel/Frame 061224/0001 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 22, 2022
From: HENKEL IP & HOLDING GMBH
To: HENKEL AG & CO. KGAA
Reel/Frame 059207/0627 →