IP Library Granted Patent US 9,879,159
Granted Patent B2
US 9,879,159 · App. 14/958,177 · Granted Jan 30, 2018

High-speed moisture-cure hybrid siloxane/silsesquioxane-urethane and siloxane/silsesquioxane-epoxy systems with adhesive properties

Inventors: Barry C. Arkles (Pipersville, PA); Youlin Pan (Langhorne, PA)
Assignee: Gelest Technologies, Inc.
C09J11/06C07F7/1804C07F7/1832C07F7/1836C08G18/289C08G18/718C08G18/73C08G77/04C08L63/00
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Quick Facts
Patent No.
US 9,879,159
App. No.
14/958,177
Granted
Jan 30, 2018
Kind
B2
Abstract

Materials containing the reaction products of a cyclic azasilane with water and a compound or polymer containing an isocyanate or epoxy functional group and methods for their synthesis are provided. Stable mixtures containing a cyclic azasilane and a compound or polymer containing an isocyanate or epoxy functional group according to invention are stored under anhydrous conditions. The invention also provides a novel class of materials, mono and bis(cycloaza)disiloxanes comprising one or two cyclic structures bridged by an Si—O—Si bond.

Claims (15)

1. A method for forming a hybrid siloxane/silsesquioxane-urethane or hybrid siloxane/silsesquioxane-epoxy material with adhesive properties comprises mixing an azasilacyclopentane with a compound or polymer containing an isocyanate or epoxy functional group under lower than normal moisture conditions having less than 50% relative humidity to form a reaction mixture, and subsequently exposing the reaction mixture to moisture to form the hybrid material, wherein the hybrid material forms by high-speed curing.

2. The method according to claim 1 , wherein the moisture comprises 50 to 85% relative humidity.

3. The method according to claim 1 , wherein the reaction mixture is stored under anhydrous conditions for six months.

4. The method according to claim 1 , wherein the reaction mixture further comprises a catalyst or accelerator.

5. The method according to claim 4 , wherein the catalyst or accelerator is selected from the group consisting of dibutyldilauryltin, dimethyltindineodecanote, and titanium diisopropoxide bis(pentanedionate).

6. A method for forming a hybrid siloxane/silsesquioxane-urethane or hybrid siloxane/silsesquioxane-epoxy material with adhesive properties comprises mixing an azasilacyclopentane with a compound or polymer containing an isocyanate or epoxy functional group under lower than normal moisture conditions having less than 50% relative humidity to form a reaction mixture, and subsequently exposing the reaction mixture to moisture to form the hybrid material, wherein the hybrid material forms in less than about two hours.

7. The method according to claim 6 , wherein the moisture comprises 50 to 85% relative humidity.

8. The method according to claim 6 , wherein the reaction mixture is stored under anhydrous conditions for six months.

9. The method according to claim 6 , wherein the reaction mixture further comprises a catalyst or accelerator.

10. The method according to claim 9 , wherein the catalyst or accelerator is selected from the group consisting of dibutyldilauryltin, dimethyltindineodecanote, and titanium diisopropoxide bis(pentanedionate).

11. A method for forming a hybrid siloxane/silsesquioxane-urethane or hybrid siloxane/silsesquioxane-epoxy material with adhesive properties comprises mixing an N-alkylazasilacyclopentane with a compound or polymer containing an isocyanate or epoxy functional group under lower than normal moisture conditions having less than 50% relative humidity to form a reaction mixture, and subsequently exposing the reaction mixture to moisture to form the hybrid material.

12. The method according to claim 11 , wherein the moisture comprises 50 to 85% relative humidity.

13. The method according to claim 11 , wherein the reaction mixture is stored under anhydrous conditions for six months.

14. The method according to claim 11 , wherein the reaction mixture further comprises a catalyst or accelerator.

15. The method according to claim 14 , wherein the catalyst or accelerator is selected from the group consisting of dibutyldilauryltin, dimethyltindineodecanote, and titanium diisopropoxide bis(pentanedionate).

Assignments (9)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 22, 2024
From: GELEST TECHNOLOGIES, INC.
To: GELEST, INC.
Reel/Frame 068467/0243 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 10, 2022
From: GELEST TECHNOLOGIES, INC.
To: GELEST, INC.
Reel/Frame 058668/0350 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 28, 2021
From: GELEST TECHNOLOGIES, INC.
To: GELEST, INC.
Reel/Frame 058595/0701 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 7, 2021
From: GELEST TECHNOLOGIES, INC.
To: GELEST, INC.
Reel/Frame 056272/0183 →
RELEASE OF SECURITY INTEREST Recorded Oct 1, 2020
From: ANTARES CAPITAL LP
To: GELEST BIOSYSTEMS, LLC; GELEST, INC.; GELEST TECHNOLOGIES, INC.
Reel/Frame 053946/0556 →
RELEASE OF SECURITY INTEREST Recorded Jun 24, 2019
From: WELLS FARGO BANK, NATIONAL ASSOCIATION
To: GELEST TECHNOLOGIES, INC.; GELEST, INC.; GELEST BIOSYSTEMS, LLC
Reel/Frame 049567/0194 →
PATENT SECURITY AGREEMENT Recorded Jun 21, 2019
From: GELEST, INC.; GELEST TECHNOLOGIES, INC.; GELEST BIOSYSTEMS, LLC
To: ANTARES CAPITAL LP
Reel/Frame 049557/0526 →
SECURITY INTEREST Recorded Aug 14, 2017
From: GELEST, INC.; GELEST TECHNOLOGIES, INC.; GELEST BIOSYSTEMS, LLC
To: WELLS FARGO BANK, NATIONAL ASSOCIATION
Reel/Frame 043540/0963 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 3, 2015
From: ARKLES, BARRY C; PAN, YOULIN
To: GELEST TECHNOLOGIES, INC.
Reel/Frame 037203/0123 →
Continuity (2)
Provisional Application 62089993 · Dec 10, 2014
Related Publication 20160168429A1 · Jun 16, 2016