IP Library Granted Patent US 8,632,654
Granted Patent B2
US 8,632,654 · App. 13/756,844 · Granted Jan 21, 2014

Hardener for epoxy resins

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Quick Facts
Patent No.
US 8,632,654
App. No.
13/756,844
Granted
Jan 21, 2014
Kind
B2
Abstract

The present application is directed to use of a thioether compound, obtainable from a first educt that comprises at least two thiol groups and from a second educt that comprises at least one α,β-unsaturated amide group as well as at least one tertiary amine group, for the hardening of reactive resins.

Claims (38)

1. A hardener composition for hardening a reactive resin of a two component curable composition, comprising a thioether compound, wherein the thioether compound is a first educt comprising at least two thiol groups; a second educt comprising at least one α,β-unsaturated amide group as well as at least one tertiary amine group; or a mixture of the first educt and the second educt.

2. The hardener composition according to claim 1 , wherein the thioether compound is a molecule comprising:

a. at least one thioether group,

b. optionally, one or more thiol groups,

c. at least one amide group, and

d. at least one tertiary amine group,

providing that the thioether compound comprises at least two sulfur-containing functional groups selected from thioether groups and/or thiol groups.

3. The hardener composition according to claim 1 , wherein the thioether compound carries at least one group of formula (I)

where

R1 and R2, mutually independently, are a C 1 to C 20 alkyl group,

R3 is a hydrogen atom or a C l to C 4 alkyl group,

n is a whole number from 1 to 20,

providing that the group of formula (I) is bound via a carbon atom to the remainder of the molecule.

4. The hardener composition according to claim 1 , wherein the thioether compound is a compound of formula (II)

where

R1 and R2, mutually independently, are a C 1 to C 20 alkyl group,

R3 is a hydrogen atom or a C 1 to C 4 alkyl group,

n is a whole number from 1 to 20,

p is a rational number from 1.0 to 5.0, and

X is a p-valent residue that is respectively bound via a carbon atom to the functional group of formula (I), and optionally comprises at least one thiol group and/or at least one thioether group,

providing that X obligatorily comprises at least one thiol group and/or at least one thioether group when p=1.

5. The hardener composition according to claim 4 , wherein

R1 and R2 denote a methyl group, and/or

R3 denotes a methyl group, and/or

n denotes the whole number 3, and/or

X denotes an oligomeric or polymeric residue.

6. The hardener composition according to claim 4 , wherein the residue X comprises alkylene diol units.

7. The hardener composition according to claim 1 further including an accelerator that comprises at least one nitrogen atom.

8. A two-component curable composition comprising a reactive resin composition and separately the thioether compound according to claim 1 .

9. The two-component curable composition of claim 8 , wherein the reactive resin is an epoxy resin.

10. A cured reaction product of the two-component composition according to claim 8 .

11. A method for adhesively bonding materials, comprising:

providing a reactive resin composition;

providing the thioether compound of claim 1 ;

mixing the reactive resin composition and the thioether compound to form a curable composition;

applying the curable composition onto a first material surface to be adhesively bonded;

disposing a second material surface to be adhesively bonded onto the applied adhesive; and

curing the applied curable composition at temperatures between −10° C. and 80° C.

Assignments (5)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 9, 2022
From: HENKEL IP & HOLDING GMBH
To: HENKEL AG & CO. KGAA
Reel/Frame 059357/0267 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 26, 2015
From: HENKEL US IP LLC
To: HENKEL IP & HOLDING GMBH
Reel/Frame 035100/0151 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 7, 2014
From: HENKEL CORPORATION
To: HENKEL US IP LLC
Reel/Frame 034183/0611 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 16, 2013
From: WALTER, PABLO; BENOMAR, MUSTAPHA; KREILING, STEFAN; SCHOENFELD, RAINER
To: HENKEL AG & CO. KGAA
Reel/Frame 031789/0891 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 16, 2013
From: WALSH, TIMOTHY P.
To: HENKEL CORPORATION
Reel/Frame 031790/0186 →