Bonding or vulcanisation compositions

Patent metadata

Field	Value
Publication number	US-2016160093-A1
Application number	US-201615045555-A
Country	US
Kind code	A1
Filing date	Feb 17, 2016
Priority date	Aug 20, 2013
Publication date	Jun 9, 2016
Grant date	—

Abstract

A particulate material which is a particulate carrier material optionally comprising one or more hydroxyl groups to which a nitroso or nitroso precursor compound is bonded. A desirable particulate carrier material is a silicaceous material, for example, silica. Such materials are useful in bonding of elastomeric materials such as rubber and in vulcanisation.

First claim

What is claimed:

1 . A particulate material comprising:
(i) a solid carrier material, and (ii) a nitroso compound and/or an aromatic oxime as a nitroso precursor compound
wherein said nitroso compound and/or said nitroso precursor compound is covalently bonded to the solid carrier material.

2 . The particulate material according to claim 1 wherein the solid carrier material comprises one or more hydroxyl groups through which the nitroso compound and/or nitroso precursor compound is bonded to the carrier material.

3 . The particulate material according to claim 1 wherein the solid carrier material is a silicaceous material.

4 . The particulate material according to claim 1 wherein the particulate carrier material is particulate silica.

5 . The particulate material according to claim 1 wherein the volume average particle size of the particulate carrier material is from about 10 nm to about 500 μm, for example, from about 50 nm to about 200 μm, such as from about 50 nm to about 1,000 nm, including from about 200 nm to about 1,000 nm, and from about 50 nm to about 200 nm.

6 . The particulate material according to claim 1 wherein the nitroso compound and/or nitroso precursor compound is bonded to the solid carrier material through the oxygen atom of one or more groups containing an Si—O moiety.

7 . The particulate material according to claim 1 wherein the nitroso compound and/or nitroso precursor compound is bonded to the solid carrier material through one or more of the oxygen atoms of one or more groups containing an —Si(OR) 2 O— moiety, wherein each R is independently selected from the group of C 1 -C 24 alkyl, C 3 -C 24 acyl, C 3 -C 24 cycloalkyl, C 5 -C 12 aryl, C 4 -C 12 heteroaryl; and is optionally substituted with at least one of —OH, amine, nitro, nitroso, —CN, halogen, C 1 -C 10 alkyl, C 3 -C 10 acyl, C 1 -C 10 alkoxy, or C 5 -C 10 aryl.

8 . The particulate material according to claim 1 wherein the nitroso compound and/or nitroso precursor compound is attached to the solid carrier material by reacting at least one C 1 -C 10 alkoxy silane group, preferably a C 1 -C 3 alkoxy silane group of the nitroso compound and/or nitroso precursor compound with one or more hydroxyl groups of the solid carrier material.

9 . The particulate material according to claim 1 wherein the nitroso compound is a nitroso silane molecule.

10 . The particulate material according to claim 1 , which is formed by reacting the solid carrier material with a nitroso compound and/or nitroso precursor compound of general formula (I)

wherein n is from 1 to 20;
X is O or S;
Y is O, S, NH, or N(R 3 );
a is 0 or 1;
each R 3 is independently selected from the group consisting of C 1 -C 10 alkyl, C 3 -C 10 cycloalkyl, C 5 -C 12 aryl, C 4 -C 12 heteroaryl;
Z is selected from the group consisting of: —CH 2 —, O, S, NH, NR 3 ; and
R 4 is selected from the group consisting of: nitrosobenzene, quinone oxime and quinone dioxime;
wherein each of R 3 and R 4 are optionally substituted with at least one of —OH, amine, nitro, nitroso, —CN, halogen, C 1 -C 10 alkyl, C 1 -C 10 alkoxy, C 3 -C 10 acyl or C 5 -C 10 aryl; and
wherein,
X 1 , X 2 and X 3 are the same or different and are selected from the group consisting of:
hydrogen, hydroxyl, —NH 2 , —NHR 3 , C 1 -C 24 alkyl, C 3 -C 24 acyl, C 1 -C 24 alkoxy, C 3 -C 24 cycloalkyl, C 5 -C 12 aryl, C 5 -C 10 aryloxy;
each group optionally substituted with at least one of —OH, amine, C 1 -C 5 alkyl, C 1 -C 5 alkoxy;
provided that
at least one of X 1 , X 2 and X 3 allows for covalent attachment of the nitroso compound and/or nitroso precursor compound of the general formula (I) to the solid carrier material.

11 . The particulate material according to claim 10 with the general formula (II)

12 . The particulate material according to claim 10 wherein X 3 is hydroxyl or C 1 -C 24 alkoxy.

13 . The particulate material according to claim 10 wherein X 2 and X 3 are the same or different and are selected form the group of hydroxyl or C 1 -C 24 alkoxy.

14 . The particulate material according to claim 10 wherein X 1 , X 2 and X 3 are the same or different and are selected from the group of hydroxyl or C 1 -C 24 alkoxy.

15 . The particulate material according to claim 1 wherein the nitroso compound has the general formula (IV):

wherein n is from 1 to 20;
c is from 1 to 2, b is from 0 to 1, with the proviso that b+c=2;
each R 1 is independently selected from the group consisting of H, C 1 -C 24 alkyl, and C 3 -C 24 acyl, preferably from C 1 -C 4 alkyl and wherein when c>1 at least one R 1 is not hydrogen; each R 2 is independently selected from the group consisting of C 1 -C 24 alkyl and C 3 -C 24 acyl, preferably from C 1 -C 4 alkyl;
X is O or S;
Y is O, S, NH, or N(R 3 );
a is 0 or 1;
each R 3 is independently selected from the group consisting of C 1 -C 10 alkyl, C 3 -C 10 cycloalkyl, C 5 -C 12 aryl, C 4 -C 12 heteroaryl;
Z is selected from the group consisting of: —CH 2 —, O, S, NH, NR 3 ; and
R 4 is selected from the group consisting of: nitrosobenzene, quinone oxime and quinone dioxime;
wherein each of R 3 and R 4 are optionally substituted with at least one of —OH, —NH 2 , nitro, nitroso, —CN, halogen, C 1 -C 10 alkyl, C 1 -C 10 alkoxy, C 3 -C 10 acyl or C 5 -C 10 aryl.

16 . A particulate material according to claim 1 wherein the nitroso precursor compound is an aromatic oxime, for example at least one of a quinone dioxime or a quinone oxime or combinations thereof.

17 . A process for the preparation of the particulate material according to claim 1 comprising the steps of:
(i) providing a solid carrier material;
(ii) providing a nitroso compound and/or nitroso precursor compound;
(iii) covalently attaching the solid carrier material of step (i) and the nitroso compound and/or nitroso precursor compound of step (ii) to each other to form a particulate carrier material optionally with a volume average particle diameter of from about 50 nm to about 500 μm.

18 . The process of claim 17 wherein the nitroso compound and/or nitroso precursor compound and the carrier material are covalently attached to each other by a condensation reaction.

19 . The process of claim 17 wherein the carrier material is formed in-situ.

20 . The process of claim 17 wherein the carrier material comprises silica nanoparticles that are formed in-situ.

21 . The process of claim 20 wherein the silica nanoparticles are formed in-situ from a tetra-alkylorthosilicate, such as tetra-ethylorthosilicate (TEOS).

22 . A composition comprising:
(a) a particulate material according to claim 1 ; and (b) one or more reactive components that cure upon exposure to suitable conditions.

23 . A composition for bonding an elastomeric material such as a rubber material to a substrate the composition comprising:
(a) a particulate material according to

Assignees

• Henkel IP & Holding GmbH

Inventors

• Fleming Eimear
• Nolan Darren
• Kneafsey Brendan
• Ledwith Deirdre

Classifications

• C09C1/3081

  Treatment with organo-silicon compounds · CPC title

• C07F7/0838

  Compounds with one or more Si-O-Si sequences (compounds with a ring containing only alternating Si and O atoms, i.e. cyclosilanes C07F7/21) · CPC title

• C08K3/36

  Silica · CPC title

• C01P2004/62

  Submicrometer sized, i.e. from 0.1-1 micrometer · CPC title

• C09J11/06 Primary

  organic · CPC title