IP Library Granted Patent US 10,662,329
Granted Patent B1
US 10,662,329 · App. 16/019,015 · Granted May 26, 2020

Bis-Schiff-base thermosetting elastomers

Inventors: Richard D. Hreha (Centerville, OH); Joel P. Brubaker (Dayton, OH); Frank M. Zalar (Beavercreek Township, OH); Michael D. Rauscher (Beavercreek, OH)
Assignee: Jalapeno Holdings, LLC
C08L83/04C08G77/388C08G77/445C08J5/005C08J5/047C08L77/10C08J2383/10C08J2477/10C08L2312/00
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Quick Facts
Patent No.
US 10,662,329
App. No.
16/019,015
Granted
May 26, 2020
Kind
B1
Abstract

Chemical compositions are provided having a structure in accordance with with the R group having a structure in accordance with R 1 includes an alkyl group, R 2 includes an alkylene group, and R 3 includes an alkylene group in accordance with (CH 2 ), with x≥2, and R 4 includes the structure of Formula (II) or Formula (III). R 5 includes a meta-substituted or para-substituted phenyl moiety. Additionally, elastomers produced by cross-linking the chemical composition of Formula (I) are provided.

Claims (37)

1. A chemical composition comprising the structure of Formula (I):

wherein:

R comprises the structure of Formula (II) or Formula (IV):

wherein, R 1 comprises an alkyl group and R 2 comprises an alkylene group and n represents any integer greater than or equal to zero;

wherein, R 3 comprises an alkylene group in accordance with (CH 2 ) x with x≥2 and n represents any integer greater than or equal to 1; and

wherein, n′ represents any integer greater than or equal to 1, R 4 comprises the structure of Formula (II) or Formula (III), and R 5 comprises the structure of Formula (V) or Formula (VI):

2. An elastomer produced by cross-linking a chemical composition comprising the structure of Formula (I):

wherein:

R comprises the structure of Formula (II) or Formula (IV):

wherein, R 1 comprises an alkyl group and R 2 comprises an alkylene group and n represents any integer greater than or equal to zero;

wherein, R 3 comprises an alkylene group in accordance with (CH 2 ) x with x≥2 and n represents any integer greater than or equal to 1; and

wherein, n′ represents any integer greater than or equal to 1, R 4 comprises the structure of Formula (II) or Formula (III), and R 5 comprises the structure of Formula (V) or Formula (VI):

3. The elastomer of claim 2 , wherein R comprises the structure of Formula (II).

4. The elastomer of claim 3 , wherein n is equal to 200 to 500, R 1 represents methyl groups, and R 2 represents a n-alkylene group.

5. The elastomer of claim 2 , wherein R comprises the structure of Formula (IV).

6. The elastomer of claim 5 , wherein n′ is equal to 1 to 10, R 4 represents an aminobenzoate terminated linear alkyl polyether moiety in accordance with Formula (III) where n is equal to 5 to 20, R 3 represents a n-alkylene group, and R 5 represents a meta-substituted phenyl moiety in accordance with Formula (V).

7. The elastomer of claim 2 , wherein the cross-linking is achieved by heating the chemical composition at 120 to 180° C. for 4 to 16 hours at approximately 760 mmHg.

8. The elastomer of claim 2 , wherein the char yield at pyrolysis at 800° C. for the elastomer is greater than 10 wt. %.

9. The elastomer of claim 2 , wherein the elastomer is used in at least one of an architecture, coating, construction, oil and gas, mining, defense, space, aerospace, automotive, marine, manufacturing, or electronic industries.

10. A polymer composite, the polymer composite comprising:

the elastomer of claim 2 , and

one or more reinforcement fillers integrated with the chemical composition prior to cross-linking.

11. The polymer composite of claim 10 , wherein the reinforcement filler comprises one or more of a nanoclay, a nanofiber, and chopped para-aramid synthetic fiber.

12. The polymer composite of claim 11 , wherein the para-aramid-synthetic fiber comprises poly-paraphenylene terephthalamide fibers.

13. The polymer composite of claim 10 , wherein the reinforcement filler has a final loading in the range of 1 wt. % to 30 wt. %.

14. The polymer composite of claim 10 , wherein the char yield at pyrolysis at 800° C. for the polymer composite is greater than 12 wt. %.

15. The polymer composite of claim 10 , wherein:

the R group of the elastomer comprises the structure of Formula (III) with wherein n equal to 5 to 20 and R 3 representing a n-alkylene group; and

the one or more reinforcement fillers comprise aramid fiber and fumed silica.

16. A high temperature insulation comprising an elastomer produced by cross-linking a chemical composition comprising the structure of Formula (I):

wherein:

R comprises the structure of Formula (II) or Formula (IV):

wherein, R 1 comprises an alkyl group and R 2 comprises an alkylene group and n represents any integer greater than or equal to zero;

wherein, R 3 comprises an alkylene group in accordance with (CH 2 ) x with x≥2 and n represents any integer greater than or equal to 1; and

wherein, n′ represents any integer greater than or equal to 1, R 4 comprises the structure of Formula (II) or Formula (III), and R 5 comprises the structure of Formula (V) or Formula (VI):

17. The high temperature insulation of claim 16 , wherein the high temperature insulation further comprises one or more reinforcement fillers integrated with the chemical composition prior to cross-linking to form a polymer composite, the reinforcement filler selected from nanoclays, nanofibers, and chopped para-aramid synthetic fibers.

18. The high temperature insulation of claim 16 , wherein the high temperature insulation material is configured for use as solid rocket motor insulation.

Assignments (8)
SECURITY INTEREST Recorded Apr 8, 2025
From: SYSTIMA TECHNOLOGIES, INC.
To: CITIBANK, N.A., AS AGENT
Reel/Frame 070775/0023 →
RELEASE OF SECURITY INTEREST Recorded Apr 8, 2025
From: TCW ASSET MANAGEMENT COMPANY, LLC
To: SYSTIMA TECHNOLOGIES, INC.
Reel/Frame 070767/0592 →
SECURITY INTEREST Recorded Sep 30, 2022
From: SYSTIMA TECHNOLOGIES, INC.
To: TCW ASSET MANAGEMENT COMPANY, LLC, AS ADMINISTRATIVE AGENT
Reel/Frame 061276/0116 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 2, 2022
From: CORNERSTONE RESEARCH GROUP, INCORPORATED
To: SYSTIMA TECHNOLOGIES, INC.
Reel/Frame 060694/0679 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 27, 2022
From: CORNERSTONE RESEARCH GROUP, INCORPORATED
To: SYSTIMA TECHNOLOGIES, INC.
Reel/Frame 060318/0876 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 14, 2022
From: JALAPENO HOLDINGS, LLC
To: CORNERSTONE RESEARCH GROUP, INC.
Reel/Frame 059595/0149 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 1, 2019
From: CORNERSTONE RESEARCH GROUP, INC.
To: JALAPENO HOLDINGS, LLC
Reel/Frame 048482/0275 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 27, 2018
From: HREHA, RICHARD D.; BRUBAKER, JOEL P.; ZALAR, FRANK M.; RAUSCHER, MICHAEL D.
To: CORNERSTONE RESEARCH GROUP, INC.
Reel/Frame 046643/0286 →
Cited By (1)
US 12,297,334