IP Library Granted Patent US 8,754,153
Granted Patent B2
US 8,754,153 · App. 13/627,335 · Granted Jun 17, 2014

Adhesive compositions for bonding composites

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 8,754,153
App. No.
13/627,335
Granted
Jun 17, 2014
Kind
B2
Abstract

The present invention relates to a non-thermosetting composition made by reacting epichlorohydrin and a primary amine, to the use of that composition for making thermosetting (curable) adhesives suitable for bonding composites, to a method of preparing composites using the thermosetting (curable) adhesives, and to the related composites bonded with the thermosetting (curable) adhesives.

Claims (26)

1. A non-thermosetting composition, comprising:

wood particles; and

a reaction product of: (a) epichlorohydrin and (b) an amine selected from the group consisting of ammonia, a primary amine, and mixtures thereof,

wherein the reaction product is produced by reacting the epichlorohydrin and the amine in a ratio of 0.25 to 0.60 moles of epichlorohydrin per atom equivalent of amine hydrogen, and wherein the reaction product is produced by reacting in a serial fashion separate portions of the epichlorohydrin and separate portions of the amine at a temperature of not greater than 60° C.

2. The non-thermosetting composition of claim 1 , wherein the reaction product is produced by reacting the epichlorohydrin and the amine in a ratio of 0.25 to 0.40 moles of epichlorohydrin per atom equivalent of amine hydrogen.

3. The non-thermosetting composition of claim 1 , wherein the reaction product is produced by reacting the epichlorohydrin and the amine in a ratio of 0.40 to 0.60 moles of epichlorohydrin per atom equivalent of amine hydrogen.

4. The non-thermosetting composition of claim 1 , wherein the ammonia is present.

5. The non-thermosetting composition of claim 1 , wherein the primary amine is present and has the formula R1-NH 2 , wherein R1is a linear alkyl of 1-4 carbon atoms, a linear hydroxy alkyl of 1-4 carbon atoms, or a linear amino alkyl of 1-4 carbon atoms.

6. The non-thermosetting composition of claim 1 , wherein the primary amine is present and comprises methyl amine, ethyl amine, n-propyl amine, ethanolamine, ethylene diamine, or a mixture thereof.

7. The non-thermosetting composition of claim 1 , wherein the non-thermosetting composition is in the form of an aqueous mixture containing the reaction product in an amount of about 20 wt % to about 80 wt %, based on the combined weight of the reaction product and water.

8. The non-thermosetting composition of claim 1 , wherein the non-thermosetting composition is in the form of a powdered solid.

9. A non-thermosetting composition, comprising:

wood particles; and

a reaction product of epichlorohydrin and an amine,

wherein the amine is selected from the group consisting of: ammonia, one or more primary amines, and any mixture thereof, and

wherein the reaction product is produced by reacting the epichlorohydrin and the amine in a ratio of 0.25 to 0.60 moles of epichlorohydrin per atom equivalent of amine hydrogen.

10. The non-thermosetting composition of claim 9 , wherein the reaction product is produced by reacting the epichlorohydrin and the amine in a ratio of 0.25 to 0.40 moles of epichlorohydrin per atom equivalent of amine hydrogen.

11. The non-thermosetting composition of claim 9 , wherein the reaction product is produced by reacting the epichlorohydrin and the amine in a ratio of 0.40 to 0.60 moles of epichlorohydrin per atom equivalent of amine hydrogen.

12. The non-thermosetting composition of claim 9 , wherein the ammonia is present.

13. The non-thermosetting composition of claim 9 , wherein the primary amine is present and has the formula R1-NH 2 , wherein R1is a linear alkyl of 1-4 carbon atoms, a linear hydroxy alkyl of 1-4 carbon atoms, or a linear amino alkyl of 1-4 carbon atoms.

14. The non-thermosetting composition of claim 9 , wherein the non-thermosetting composition is in the form of an aqueous mixture containing the reaction product in an amount of about 20 wt % to about 80 wt %, based on the combined weight of the reaction product and water.

15. The non-thermosetting composition of claim 9 , wherein the non-thermosetting composition is in the form of a powdered solid.

16. A non-thermosetting composition, comprising:

wood particles; and

a reaction product of epichlorohydrin and an amine reacted at an epichlorohydrin to amine ratio of 0.25 to 0.60 moles of epichlorohydrin per atom equivalent of amine hydrogen, wherein the amine is selected from the group consisting of ammonia, one or more primary amines, and any mixture thereof, and wherein the non-thermosetting composition is in the form of an aqueous mixture containing the reaction product in an amount of about 20 wt % to about 80 wt %, based on the combined weight of the reaction product and water.

17. The non-thermosetting composition of claim 16 , wherein the epichlorohydrin and amine are reacted at an epichlorohydrin to amine ratio of 0.25 to 0.40 moles of epichlorohydrin per atom equivalent of amine hydrogen.

Assignments (3)
ASSIGNMENT OF PATENT AND TRADEMARK SECURITY INTEREST Recorded May 12, 2025
From: MACQUARIE CAPITAL FUNDING LLC
To: JPMORGAN CHASE BANK, N.A.
Reel/Frame 071276/0379 →
SECURITY INTEREST Recorded Jun 9, 2022
From: GEORGIA-PACIFIC CHEMICALS LLC; GEORGIA-PACIFIC CONSUMER PRODUCTS LP; ENERG2 TECHNOLOGIES, INC.; KOCH AGRONOMIC SERVICES LLC; BAKELITE UK HOLDING LTD.; SURFACE TECH LLC
To: GOLDMAN SACHS BANK USA, AS ADMINISTRATIVE AGENT
Reel/Frame 060328/0250 →
SECURITY INTEREST Recorded Jun 9, 2022
From: GEORGIA-PACIFIC CHEMICALS LLC; GEORGIA-PACIFIC CONSUMER PRODUCTS LP; ENERG2 TECHNOLOGIES, INC.; KOCH AGRONOMIC SERVICES LLC; BAKELITE UK HOLDING LTD.
To: MACQUARIE CAPITAL FUNDING LLC, AS ADMINISTRATIVE AGENT
Reel/Frame 060328/0327 →