IP Library Granted Patent US 8,840,751
Granted Patent B2
US 8,840,751 · App. 13/412,745 · Granted Sep 23, 2014

Bonding compositions

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Quick Facts
Patent No.
US 8,840,751
App. No.
13/412,745
Granted
Sep 23, 2014
Kind
B2
Abstract

Methods for bonding polymeric substrates to hydroxylated surfaces such as glass are disclosed. The polymeric substrates may be elastomeric substrates such as a natural or synthetic rubber. The method may comprise applying a compound comprising at least one alkoxy silane moiety and at least one moiety selected from a nitrosoaromatic or a nitrosoaromatic precursor to one of the substrates. The nitrosoaromatic moiety may be a nitrosobenzene. The nitrosoaromatic precursor may be a nitrosobenzene precursor, such as at least one of a quinone dioxime or a quinone oxime. Novel primers and compounds suitable for use in the bonding process are also disclosed.

Claims (28)

1. A process for bonding two substrates together comprising the steps of:

(i) applying a primer comprising a silicate, an aluminate, a germinate or combinations thereof to at least one substrate;

(ii) applying a compound comprising;

a) at least one alkoxy silane moiety; and

b) at least one moiety selected from an aromatic nitroso or an aromatic nitroso precursor and combinations thereof;

to at least one substrate, and

(iii) mating the first and second substrates so as to form a bond with the composition.

2. A process according to claim 1 , further comprising the step of heating at least one of the first or second substrates subsequent to bringing the substrates together.

3. A process according to claim 1 wherein the least one moiety selected from an aromatic nitroso or an aromatic nitroso precursor is a nitrosobenzene or a nitrosobenzene precursor.

4. A process according to claim 1 wherein said alkoxy silane moiety is of the structure:

wherein ‘a’ can be 1-3 and ‘b’ can be 0-2, wherein a+b=3 and at least one alkoxy group is present;

R 1 can be selected from the group consisting of H, C 1 -C 24 alkyl, C 3 -C 24 acyl, wherein when a ≧1 at least one R 1 is not hydrogen; and

R 2 can be selected from C 1 -C 24 alkyl and C 3 -C 24 acyl.

5. A process according to claim 1 wherein the compound is of the general structure:

wherein n can be 1-10;

‘a’ can be 1-3 and ‘b’ can be 0-2; wherein a+b=3 and at least one alkoxy group is present;

R 1 can be selected from the group consisting of H, C 1 -C 24 alkyl, C 3 -C 24 acyl, and wherein when a ≧1 at least one R 1 is not hydrogen;

R 2 can be selected from C 1 -C 24 alkyl and C 3 -C 24 acyl;

X can be O or S;

Y can be —O, —S, or —N(R 3 ); and

R 3 can be a moiety comprising nitrosoaromatic, or a nitrosoaromatic precursor.

6. A process according to claim 5 wherein R 3 is a moiety comprising nitrosobenzene, quinone dioxime or quinone oxime.

7. A process according to claim 5 wherein R 3 is selected from the group comprising (showing linkage through Y):

wherein R 4 can be C 1 to C 10 ; and

Z indicates that the rings of the above structures can optionally be mono-, di-, tri- or tetrasubstituted with the group consisting of C 1 -C 20 alkyl, C 3 -C 20 cycloalkyl, C 1 -C 20 alkoxy, C 7 -C 20 aralkyl, C 7 -C 20 alkaryl, C 5 -C 20 arylamine, C 5 -C 20 arylnitroso, amino, hydroxy, halogen and combinations thereof, and further wherein the substituents can either be the same or different on each carbon atom of the ring.

8. An assembly comprising at least two substrates bound together by a process according to claim 1 .

9. An article of manufacture prepared utilising the process according to claim 1 .

10. An article according to claim 9 , wherein the article is selected from the group comprising automotive timing belts, glass fibre reinforced plastics and composite materials, reinforced rubbers, tires, conveyor belts and woven articles.

Assignments (8)
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 24, 2014
From: HENKEL AG & CO. KGAA
To: HENKEL IP & HOLDING GMBH
Reel/Frame 032329/0172 →
MERGER Recorded Feb 24, 2014
From: HENKEL IRELAND LIMITED
To: HENKEL AG & CO. KGAA
Reel/Frame 032329/0132 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 24, 2013
From: HENKEL IRELAND LIMITED
To: LOCTITE (R&D) LIMITED
Reel/Frame 031473/0345 →
MERGER Recorded Oct 24, 2013
From: LOCTITE (R&D) LIMITED
To: HENKEL IRELAND HOLDING B.V.
Reel/Frame 031473/0391 →
MERGER Recorded Oct 24, 2013
From: HENKEL IRELAND HOLDING B.V.
To: HENKEL IRELAND LIMITED
Reel/Frame 031473/0453 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 24, 2013
From: WEFRINGHAUS, RAINER K.
To: HENKEL AG & CO. KGAA
Reel/Frame 031473/0122 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 24, 2013
From: FAY, NIGEL; NOLAN, DARREN; FLEMING, EIMEAR N; KNEAFSEY, BRENDAN J.
To: HENKEL IRELAND LIMITED
Reel/Frame 031473/0314 →