IP Library Granted Patent US 7,625,977
Granted Patent B2
US 7,625,977 · App. 12/142,261 · Granted Dec 1, 2009

Adhesive of epoxy resin, toughener and blocked isocyanate polytetrahydrofuran toughener

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 7,625,977
App. No.
12/142,261
Granted
Dec 1, 2009
Kind
B2
Abstract

Epoxy adhesive compositions contain an epoxy resin, rubber modification, a toughener and a curing agent. The tougher has capped epoxide-reactive groups, and at least one polytetrahydrofuran block having a mass of 2200-4500 daltons. The selection of toughener in a rubber-modified epoxy-based structural adhesive provides for very good low temperature performance.

Claims (21)

1. A one-component structural adhesive, comprising:

A) one or more epoxy resins;

B) at least one toughening rubber;

C) a polytetrahydrofuran-based toughener that has isocyanate groups that are blocked or capped with a phenolic compound, an aminophenolic compound, a primary or secondary aliphatic or cycloaliphatic amine, an alkyl alcohol, an aromatic amine, an alkyl benzyl amine or an alkyl thiol; and

D) one or more epoxy curing agents;

wherein the polytetrahydrofuran-based toughener includes a liquid or low-melting elastomeric material having capped or blocked reactive groups and at least one polytetrahydrofuran block having a molecular weight of from 2200 to 4500 daltons.

2. The structural adhesive of claim 1 , wherein the polytetrahydrofuran-based toughener is formed by reacting a polytetrahydrofuran polyol and an aliphatic polyisocyanate, and optionally a small quantity of a branching or crosslinking agent having 3 or more isocyanate-reactive group per molecule, to form a prepolymer having free isocyanate groups, and then blocking the isocyanate groups.

3. The structural adhesive of claim 2 , wherein the prepolymer having free isocyanate groups has an isocyanate content of from 0.5 to 4% by weight.

4. The structural adhesive of claim 3 , wherein the epoxy resin includes at least one diglycidyl ether of a bisphenol.

5. The structural adhesive of claim 4 , wherein the toughening rubber includes at least one core-shell rubber.

6. The structural adhesive of claim 5 , wherein the core-shell rubber has a rubbery core that has a T g of less than −50° C. and at least one shell portion having a T g of at least 50° C.

7. The structural adhesive of claim 1 , wherein the toughening rubber is an epoxy-terminated adduct of an epoxy resin and at least one liquid rubber that has epoxide-reactive groups, such as amino or preferably carboxyl groups.

8. The structural adhesive of claim 7 , wherein the liquid rubber is a carboxyl-terminated butadiene-acrylonitrile copolymer that contains up to 30 weight percent polymerized unsaturated nitrile monomer.

9. The structural adhesive of claim 1 , which has total rubber content of from 3 to 15 weight percent.

10. The structural adhesive of claim 1 , which contains from 5 to 30 weight percent of the polytetrahydrofuran-based toughener.

11. The structural adhesive of claim 10 , wherein the polytetrahydrofuran-based toughener has a weight average molecular weight of from 8,000 to 80,000.

12. The structural adhesive of claim 1 , further containing at least one filler.

13. The structural adhesive of claim 12 , which contains from 10 to 25% by weight filler.

14. The structural adhesive of claim 1 , wherein the polytetrahydrofuran block has a molecular weight of from 2500 to 3500 daltons.

15. A method comprising applying the structural adhesive of claim 1 to the surfaces of two metals, and curing the structural adhesive to form an adhesive bond between the two metals.

16. The method of claim 15 , wherein at least one of the metals is galvaneal.

Assignments (7)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 10, 2024
From: DOW GLOBAL TECHNOLOGIES LLC
To: THE DOW CHEMICAL COMPANY
Reel/Frame 069923/0030 →
CHANGE OF LEGAL ENTITY Recorded Sep 10, 2024
From: DDP SPECIALTY ELECTRONIC MATERIALS US, INC
To: DDP SPECIALTY ELECTRONIC MATERIALS US, LLC
Reel/Frame 068907/0881 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 10, 2024
From: THE DOW CHEMICAL COMPANY
To: DDP SPECIALTY ELECTRONIC MATERIALS US, INC
Reel/Frame 068922/0001 →
CHANGE OF NAME Recorded Oct 11, 2017
From: DOW GLOBAL TECHNOLOGIES INC.
To: DOW GLOBAL TECHNOLOGIES LLC
Reel/Frame 044184/0683 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 21, 2009
From: LUTZ, ANDREAS; SCHNEIDER, DANIEL
To: DOW EUROPE GMBH
Reel/Frame 023402/0382 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 21, 2009
From: DOW EUROPE GMBH
To: THE DOW CHEMICAL COMPANY
Reel/Frame 023402/0399 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 21, 2009
From: THE DOW CHEMICAL COMPANY
To: DOW GLOBAL TECHNOLOGIES INC.
Reel/Frame 023402/0429 →