IP Library Granted Patent US 10,919,839
Granted Patent B2
US 10,919,839 · App. 16/005,550 · Granted Feb 16, 2021

Silicon-containing compositions and their methods of use

Inventors: Szymon Kosinski (Hayward, CA); Stefan J. Pastine (San Francisco, CA)
Assignee: Aditya Birla Chemicals (USA) LLC
C07C217/08C07C213/08C08G59/066C08G59/4085C08G59/504C08J11/16C08J11/26C08J2363/00C08J2379/02
View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 10,919,839
App. No.
16/005,550
Granted
Feb 16, 2021
Kind
B2
Abstract

Provided herein are silicon-containing recyclable polyamino compounds; epoxy resin compositions containing these silicon-containing reworkable or recyclable polyamino compounds; and methods of their use.

Claims (59)

1. A compound of Formula (I-A-iv)

or a salt thereof, wherein:

z is an integer from 1 to 6;

t is an integer from 0 to 1;

q1 is an integer from 1 to 4;

q2 is an integer from 1 to 3;

each of R 4A , R 4B , R 4C , and R 4D is independently for each occurrence hydrogen or alkyl; and each occurrence of R 5A is independently alkyl, cycloalkyl, aryl, or —OR C , wherein R C is alkyl, cycloalkyl, heterocyclyl, alkenyl, alkynyl, cycloalkenyl, aryl or heteroaryl, provided that the sum of t, q1, and q2 is 4.

2. The compound of claim 1 , wherein the compound of Formula (I-A) is a compound of Formula (I-A-ii-1)

3. The compound of claim 1 , wherein the compound is:

4. The compound of claim 3 , wherein the compound is:

5. A composition comprising the reaction product of:

an epoxy resin; and

a compound of Formula (I-A-iv):

wherein:

z is an integer from 1 to 6;

t is an integer from 0 to 1;

q1 is an integer from 1 to 4;

q2 is an integer from 0 to 3;

each of R 4A , R 4B , R 4C , and R 4D is independently for each occurrence hydrogen or alkyl;

and each occurrence of R 5A is independently alkyl, cycloalkyl, aryl, or —OR C , wherein R C is alkyl, cycloalkyl, heterocyclyl, alkenyl, alkynyl, cycloalkenyl, aryl or heteroaryl, provided that the sum of t, q1, and q2 is 4.

6. The composition of claim 5 , wherein the compound of Formula (I-A) is a compound of Formula (I-A-ii-1):

7. The composition of claim 5 , wherein the compound of Formula (I-A) is:

8. The composition of claim 7 , wherein the compound of Formula (I-A) is:

9. The composition of claim 5 , wherein the epoxy resin comprises a diepoxide resin.

10. A composition comprising the reaction product of:

an epoxy resin;

a compound of Formula (I-A);

(R 5 ) t —Si O—W—NH 2 ) q    Formula (I-A)

wherein:

q is 4, 3, 2, or 1;

t is 0, 1, 2, or 3;

the sum of q and t is 4;

each occurrence of W is independently alkylene, cycloalkylene, heterocyclylene, alkenylene, alkynylene, cycloalkenylene, arylene, or heteroarylene; and

each occurrence of R 5 is independently hydrogen, alkyl, cycloalkyl, heterocyclyl, alkenyl, alkynyl, cycloalkenyl, aryl, heteroaryl or —OR C , wherein R C is alkyl, cycloalkyl, heterocyclyl, alkenyl, alkynyl, cycloalkenyl, aryl or heteroaryl; and

a compound having the Formula (II-A-1):

wherein: each of R 6A and R 6B is independently hydrogen or alkyl;

each of R 7A , R 7B , R 8A , R 8B , R 8C and R 8D is independently for each occurrence hydrogen or alkyl; and

each of n1 and n2 is independently 1 or 2.

11. A method for recycling the composition of claim 10 , comprising contacting the composition with an acid.

12. The composition of claim 1 , wherein the compound of Formula (I-A) is a compound of Formula (I-A-iv)

wherein:

z is an integer from 1 to 6; t is an integer from 0 to 1;

q1 is an integer from 0 to 4; q2 is an integer from 0 to 4;

each of R 4A , R 4B , R 4C , and R 4D is independently for each occurrence hydrogen or alkyl; and

each occurrence of R 5A is independently alkyl, cycloalkyl, aryl, or —OR C , wherein R C is alkyl, cycloalkyl, heterocyclyl, alkenyl, alkynyl, cycloalkenyl, aryl or heteroaryl,

provided that the sum of t, q1, and q2 is 4, and the sum of q1 and q2 is not 0.

13. The composition of claim 10 , wherein the compound of Formula (I-A) is a compound of Formula (I-A-i-1) or (I-A-ii-1):

wherein:

z is an integer from 1 to 6; each of R 4A , R 4B , R 4C , and R 4D is independently for each occurrence hydrogen or alkyl; and

each occurrence of R 5A is independently alkyl, cycloalkyl, aryl, or —OR C , wherein R C is alkyl, cycloalkyl, heterocyclyl, alkenyl, alkynyl, cycloalkenyl, aryl or heteroaryl.

14. The composition of claim 10 , wherein the compound of Formula (I-A) is a compound of Formula (I-A-iii):

wherein:

each of X 1 , X 2 , X 3 , and X 4 is independently alkylene, cycloalkylene, heterocyclylene, alkenylene, alkynylene, cycloalkenylene, arylene, or heteroarylene.

15. The composition of claim 10 , wherein the compound of Formula (I-A) is:

16. The composition of claim 10 , wherein the compound of Formula (I-A) is:

17. The composition of claim 16 , wherein the compound of Formula (I-A) is:

18. The composition of claim 10 , wherein the compound of Formula (II-A-1) is:

19. The composition of claim 10 , wherein the composition comprises a chain extender.

20. The composition of claim 10 , wherein the epoxy resin comprises a diepoxide resin.

Assignments (3)
CHANGE OF NAME Recorded Oct 6, 2022
From: ADITYA BIRLA CHEMICALS (USA), LLC
To: ADITYA BIRLA CHEMICALS (USA), INC.
Reel/Frame 061622/0923 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 1, 2020
From: CONNORA TECHNOLOGIES, INC.
To: ADITYA BIRLA CHEMICALS (USA) LLC
Reel/Frame 052801/0479 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 19, 2018
From: KOSINSKI, SZYMON; PASTINE, STEFAN J.
To: CONNORA TECHNOLOGIES, INC.
Reel/Frame 046399/0696 →
Continuity (2)
Provisional Application 62530933 · Jul 11, 2017
Related Publication 20190016870A1 · Jan 17, 2019