IP Library Granted Patent US 11,274,236
Granted Patent B2
US 11,274,236 · App. 16/482,925 · Granted Mar 15, 2022

One-component toughened epoxy adhesives containing a mixture of latent curing agents

Inventors: Tyler Auvil (Auburn Hills, MI); Bindu Krishnan (Freeport, TX); Andreas Lutz (Galgenen, CH); Felix Koch (Freienbach, CH); Cody Clinton (Freeport, TX)
Assignee: DDP SPECIALTY ELECTRONIC MATERIALS US, LLC
C09J163/00B32B7/12C08G59/4021C08G59/4035C08G64/04C09J109/00B32B2250/02B32B2255/02B32B2255/06B32B2255/10C09J2203/00
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Quick Facts
Patent No.
US 11,274,236
App. No.
16/482,925
Granted
Mar 15, 2022
Kind
B2
Abstract

A one-component toughened epoxy-modified polyurethane and/or urea adhesive includes a mixture of dicyandiamide and a dihdyrazide as curing agents. The mixture of curing agents permits the adhesive to be cured at lower temperatures while developing good adhesive and mechanical properties in the cured adhesive.

Claims (9)

1. A method for bonding two substrates, comprising forming a layer of an adhesive comprising in admixture A) at least one non-rubber-modified epoxy resin, B) at least one toughening agent, C) at least one epoxy curing catalyst and D) a curing agent mixture that includes dicyandiamide and one or more dihydrazide compounds, the dicyandiamide and one or more dihydrazide compounds being present at a weight ratio of 0.63 to 99:1, at a bondline between the two substrates to form an assembly and then curing the adhesive layer at the bondline by heating to a temperature of 130 to 165° C. to form a cured adhesive bonded to the two substrates at the bondline, wherein one of the substrates is a metal and the other substrate is a thermoplastic organic polymer, a thermoset organic polymer or a fiber composite.

2. The method of claim 1 , wherein the two substrates have coefficients of linear thermal expansion that are different from each other by at least 5×10 −6 m/m-K.

3. A method for forming a bonded and coated assembly, comprising 1) forming a layer of the adhesive comprising in admixture A) at least one non-rubber-modified epoxy resin, B) at least one toughening agent, C) at least one epoxy curing catalyst and D) a curing agent mixture that includes dicyandiamide and one or more dihydrazide compounds, the dicyandiamide and one or more dihydrazide compounds being present at a weight ratio of 1:99 to 99:1 at a bondline between a first and a second substrate to form an assembly that includes the first and second substrates each in contact with the adhesive composition at the bondline; then

2) immersing the assembly into a coating bath to form a layer of an uncured coating on at least a portion of an exposed surface of the assembly; and

3) heating the assembly to a temperature of at least 130° C. to cure the adhesive to form a cured adhesive bonded to the substrates at the bondline and simultaneously cure the coating layer.

4. The method of claim 3 wherein the temperature is 130 to 175° C.

5. The method of claim 3 wherein the temperature is 133 to 165° C.

6. The method of claim 3 , wherein the first and second substrates have coefficients of linear thermal expansion that are different from each other by at least 5×10 −6 m/m-K.

7. The method of claim 3 , wherein one of the substrates is a metal and the other substrate is a thermoplastic organic polymer, a thermoset organic polymer or a fiber composite.

Assignments (9)
CHANGE OF NAME Recorded Mar 25, 2021
From: DDP SPECIALTY ELECTRONIC MATERIALS US, INC.
To: DDP SPECIALTY ELECTRONIC MATERIALS US, LLC
Reel/Frame 055734/0482 →
CHANGE OF NAME Recorded Mar 18, 2021
From: DDP SPECIALTY ELECTRONIC MATERIALS US, INC.
To: DDP SPECIALTY ELECTRONIC MATERIALS US, LLC
Reel/Frame 056621/0529 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 24, 2021
From: CLINTON, CODY
To: THE DOW CHEMICAL COMPANY
Reel/Frame 055388/0433 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 24, 2021
From: LUTZ, ANDREAS; KOCH, FELIX
To: DOW EUROPE GMBH
Reel/Frame 055388/0899 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 24, 2021
From: THE DOW CHEMICAL COMPANY
To: DOW GLOBAL TECHNOLOGIES LLC
Reel/Frame 055389/0441 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 24, 2021
From: DOW EUROPE GMBH
To: DOW GLOBAL TECHNOLOGIES LLC
Reel/Frame 055389/0508 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 24, 2021
From: THE DOW CHEMICAL COMPANY
To: DDP SPECIALTY ELECTRONIC MATERIALS US, INC.
Reel/Frame 055390/0068 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 24, 2021
From: DOW GLOBAL TECHNOLOGIES LLC
To: THE DOW CHEMICAL COMPANY
Reel/Frame 055436/0589 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 24, 2021
From: AUVIL, TYLER; KRISHNAN, BINDU
To: DOW GLOBAL TECHNOLOGIES LLC
Reel/Frame 055388/0292 →
Continuity (2)
Provisional Application 62463704 · Feb 26, 2017
Related Publication 20190352549A1 · Nov 21, 2019