US 2002/0055646 A1 · Blocked mercaptosilane coupling agents for filled rubbers

Abstract

Disclosed herein is a process for the manufacture of a blocked mercaptosilane wherein the process is selected from the group consisting of: (1) reacting a mercaptosilane and a monoacid anhydride corresponding to a thioester group present in the desired product; (2) reacting an alkali salt of a mercaptosilane with the appropriate acid anhydride or acid halide; (3) transesterifying a mercaptosilane and an ester in the presence of an alkali metal of an acid corresponding to the ester; (4) transesterifying a thioester silane and another ester; (5) transesterifying a 1-sila-2-thiacyclopentane or a 1-sila-2-thiacyclohexane and an ester; and (6) reacting an alkali metal salt of a thioacid with a haloalkylsilane.

Claims66

Dependent claims

A process for the manufacture of a blocked mercaptosilane wherein the process is selected from the group consisting of:

(1) reacting a mercaptosilane and a monoacid anhydride corresponding to a thioester group present in the desired product;
(2) reacting an alkali metal salt of a mercaptosilane with an appropriate acid anhydride or acid halide;
(3) transesterifying a mercaptosilane and an ester in the presence of an alkali metal salt of an acid corresponding to the ester;
(4) transesterifying a thioester silane and another ester;
(5) transesterifying a 1-sila-2-thiacyclopentane or a 1-sila-2-thiacyclohexane and an ester;
and (6) reacting an alkali metal salt of a thioacid with a haloalkylsilane.

3 more elements

A process for the manufacture of a blocked mercaptosilane wherein the process is selected from the group consisting of:

(1) reacting a mercaptosilane and an inorganic monoacid anhydride corresponding to a thioester group present in the desired product;
(2) reacting an alkali metal salt of a mercaptosilane with an appropriate inorganic acid anhydride or inorganic acid halide;
(3) transesterifying a mercaptosilane and an ester in the presence of an alkali metal of an acid corresponding to the ester;
(4) transesterifying a thioester silane and another ester;
(5) transesterifying a 1-sila-2-thiacyclopentane or a 1-sila-2-thiacyclohexane and an ester;
and (6) reacting an alkali metal salt of a thioacid with a haloalkylsilane, wherein the blocked mercaptosilane produced is selected from the group consisting of 2-triethoxysilyl-1-ethyl thioacetate;
2-trimethoxysilyl-1-ethyl thioacetate;
2-(methyldimethoxysilyl)-1-ethyl thioacetate;
3-trimethoxysilyl-1-propyl thioacetate;
triethoxysilylmethyl thioacetate;
trimethoxysilylmethyl thioacetate, triisopropoxysilylmethyl thioacetate;
methyldiethoxysilylmethyl thioacetate;
methyldimethoxysilylmethyl thioacetate;
methyldiisopropoxysilylmethyl thioacetate;
dimethylethoxysilylmethyl thioacetate;
dimethylmethoxysilylmethyl thioacetate;
dimethylisopropoxysilylmethyl thioacetate;
2-triisopropoxysilyl-1-ethyl thioacetate;
2-(methyldiethoxysilyl)-1-ethyl thioacetate;
2-(methyldiisopropoxysilyl)-1-ethyl thioacetate;
2-(dimethylethoxysilyl)-1-ethyl thioacetate;
2-(dimethylmethoxysilyl)-1-ethyl thioacetate;
2-(dimethylisopropoxysilyl)-1-ethyl thioacetate;
3-triethoxysilyl-1-propyl thioacetate;
3-triisopropoxysilyl-1-propyl thioacetate;
3-methyldiethoxysilyl-1-propyl thioacetate;
3-methyldimethoxysilyl-1-propyl thioacetate;
3-methyldiisopropoxysilyl-1-propyl thioacetate;
1-(2-triethoxysilyl-1-ethyl)-4-thioacetylcyclohexane;
1-(2-triethoxysilyl-1-ethyl)-3-thioacetylcyclohexane;
2-triethoxysilyl-5-thioacetylnorbornene;
2-triethoxysilyl-4-thioacetylnorbornene;
2-(2-triethoxysilyl-1-ethyl)-5-thioacetylnorbornene;
2-(2-triethoxysilyl-1-ethyl)-4-thioacetylnorbornene;
1-(1-oxo-2-thia-5-triethoxysilylpenyl)benzoic acid;
6-triethoxysilyl-1-hexyl thioacetate;
1-triethoxysilyl-5-hexyl thioacetate;
8-triethoxysilyl-1-octyl thioacetate;
1-triethoxysilyl-7-octyl thioacetate;
6-triethoxysilyl-1-hexyl thioacetate;
1-triethoxysilyl-5-octyl thioacetate;
8-trimethoxysilyl-1-octyl thioacetate;
1-trimethoxysilyl-7-octyl thioacetate;
10-triethoxysilyl-1-decyl thioacetate;
11-triethoxysilyl-9-decyl thioacetate;
1-triethoxysilyl-2-butyl thioacetate;
1-triethoxysilyl-3-butyl thioacetate;
1-triethoxysilyl-3-methyl-2-butyl thioacetate;
1-triethoxysilyl-3-methyl-3-butyl thioacetate;
3-trimethoxysilyl-1-propyl thiooctanoate;
3-triethoxysilyl-1-propyl thiopalmitate;
3-triethoxysilyl-1-propyl thiooctanoate;
3-triethoxysilyl-1-propyl thiobenzoate;
3-triethoxysilyl-1-propyl thio-2-ethylhexanoate;
3-methyldiacetoxysilyl-1-propyl thioacetate;
3-triacetoxysilyl-1-propyl thioacetate;
2-methyldiacetoxysilyl-1-ethyl thioacetate;
2-triacetoxysilyl-1-ethyl thioacetate;
1-methyldiacetoxysilyl-l-ethyl thioacetate;
1-triacetoxysilyl-1-ethyl thioacetate;
tris-(3-triethoxysilyl-1-propyl)trithiophosphate;
bis-(3-triethoxysilyl-1-propyl)methyldithiophosphonate;
bis-(3-triethoxysilyl-1-propyl)ethyldithiophosphonate;
3-triethoxysilyl-1-propyldimethylthiophosphinate;
3-triethoxysilyl-1-propyldiethylthiophosphinate;
tris-(3-triethoxysilyl-1-propyl)tetrathiophosphate;
bis-(3-triethoxysilyl-1-propyl)methyltrithiophosphonate;
bis-(3-triethoxysilyl-1-propyl)ethyltrithiophosphonate;
3-triethoxysilyl-1-propyldimethyldithiophosphinate;
tris-(3-methyldimethoxysilyl-1-propyl)trithiophosphate;
bis-(3-methyldimethoxysilyl-1-propyl)methyldithiophosphonate;
bis-(3-methyldimethoxysilyl-1-propyl)ethyldithiophosphonate;
3-methyldimethoxysilyl-1-propyldimethylthiophosphinate;
3-methyldimethoxysilyl-1-propyldiethylthiophosphinate;
3-triethoxysilyl-1-propylmethylthiophosphate;
3-methoxysilyl-1-propylmethanethiosulphonate;
3-triethoxysilyl-1-propylethanethiosulphonate;
3-triethoxysilyl-1-propylbenzenethiosulphonate;
3-triethoxysilyl-1-propyltoluenethiosulphonate;
3-triethoxysilyl-1-propylnaphthalenethiosulphonate;
3-triethoxysilyl-1-propylxylenethiosulphonate;
triethoxysilylmethylmethylthiosulphate;
triethoxysilylmethylmethanethiosulphonate;
triethoxysilylmethylethanethiosulphonate;
triethoxysilylmethylbenzenethiosulphonate;
trietboxysilylmethyltoluenethiosulphonate;
triethoxysilylmethylnaphthalenethiosulphonate;
and triethoxysilylmethylxylenethiosulphonate.

85 more elements

A blocked mercaptosilane manufactured by a process selected from the group consisting of (1) reacting a mercaptosilane and an inorganic monoacid anhydride corresponding to a thioester group present in the desired product;

(2) reacting an alkali metal salt of a mercaptosilane with an appropriate inorganic acid anhydride or inorganic acid halide;
(3) transesterifying a mercaptosilane and an ester in the presence of an alkali metal of an acid corresponding to the ester;
(4) transesterifying a thioester silane and another ester;
(5) transesterifying a 1-sila-2-thiacyclopentane or a 1-sila-2-thiacyclohexane and an ester;
and (6) reacting an alkali metal salt of a thioacid with a haloalkylsilane, wherein the blocked mercaptosilane so produced is selected from the group consisting of 2-triethoxysilyl-1-ethyl thioacetate;
2-trimethoxysilyl-1-ethyl thioacetate;
2-(methyldimethoxysilyl)-1-ethyl thioacetate;
3-trimethoxysilyl-1-propyl thioacetate;
triethoxysilylmethyl thioacetate;
trimethoxysilylmethyl thioacetate, triisopropoxysilylmethyl thioacetate;
methyldiethoxysilylmethyl thioacetate;
methyldimethoxysilylmethyl thioacetate;
methyldiisopropoxysilylmethyl thioacetate;
dimethylethoxysil ylmethyl thioacetate;
dimethylmethoxysilylmethyl thio acetate;
dimethylisopropoxysilylmethyl thioacetate;
2-triisopropoxysilyl-1-ethyl thioacetate;
2-(methyldiethoxysilyl)-1-ethyl thioacetate;
2-(methyldiisopropoxysilyl)-1-ethyl thioacetate;
2-(dimethylethoxysilyl) 1-ethyl thioacetate;
2-(dimethylmethoxysilyl)-1-ethyl thioacetate;
2-(dimethylisopropoxysilyl )-methyl thioacetate;
3-triethoxysilyl-1-propyl thioacetate;
3-triisopropoxysilyl-1-propyl thioacetate;
3-methyldiethoxysilyl-1-propyl thioacetate;
3-methyldimethoxysilyl-1-propyl thioacetate;
3-methyldiisopropoxysilyl-1-propyl thioacetate;
1-(2-triethoxysilyl-1-ethyl)-4-thioacetylcyclohexane;
1-(2-triethoxysilyl-1-ethyl)-3-thioacetylcyclohexane;
2-triethoxysilyl-5-thioacetylnorbornene;
2-triethoxysilyl-4-thioacetylnorbornene;
2-(2-triethoxysilyl-1-ethyl)-5-thioacetylnorbornene;
2-(2-triethoxysilyl-1-ethyl)-4-thioacetylnorbornene;
1-(1-oxo-2-thia-5-triethoxysilylpenyl)benzoic acid;
6-triethoxysilyl-1-hexyl thioacetate;
1-triethoxysilyl-5-hexyl thioacetate;
8-triethoxysilyl-1-octyl thioacetate;
1-triethoxysilyl-7-octyl thioacetate;
6-triethoxysilyl-1-hexyl thioacetate;
1-triethoxysilyl-5-octyl thioacetate;
8-trimethoxysilyl-1-octyl thioacetate;
1-trimethoxysilyl-7-octyl thioacetate;
10-triethoxysilyl-1-decyl thioacetate;
1-triethoxysilyl-9-decyl thioacetate;
1-triethoxysilyl-2-butyl thioacetate;
1-triethoxysilyl-3-butyl thioacetate;
1-triethoxysilyl-3-methyl-2-butyl thioacetate;
1-triethoxysilyl-3-methyl-3-butyl thioacetate;
3-trimethoxysilyl-1-propyl thiooctanoate;
3-triethoxysilyl-1-propyl thiopalmitate;
3-triethoxysilyl-1-propyl thiooctanoate;
3-triethoxysilyl-1-propyl thiobenzoate;
3-triethoxysilyl-1-propyl thio-2-ethylhexanoate;
3-methyldiacetoxysilyl-1-propyl thioacetate;
3-triacetoxysilyl-1-propyl thioaceteate;
2-methyldiacetoxysily-1-ethyl thioacetate;
2-triacetoxysilyl-1-ethyl thioacetate;
1-methyldiacetoxysilyl-1-ethyl thioacetate;
1-triacetoxysilyl-1-ethyl thioacetate;
tris-(3-triethoxysilyl-1-propyl)trithiophosphate;
bis-(3-triethoxysilyl-1-propyl)methyldithiophosphonate;
bis-(3-triethoxysilyl-1-propyl)ethyldithiophosphonate;
3-triethoxysilyl-1-propyldimethylthiophosphinate;
3-triethoxysilyl-1-propyldiethylthiophosphinate;
tris-(3-triethoxysilyl-1-propyl)tetra thiophosphate;
bis-(3-triethoxysilyl-1-propyl)methyltrithiophosphonate;
bis-(3-triethoxysilyl-1-propyl)ethyltrithiophosphonate;
3-triethoxysilyl-1-propyldimethyldithiophosphinate;
tris-(3-methyldimethoxysilyl-1-propyl)trithiophosphate;
bis-(3-methyldimethoxysilyl-1-propyl)methyldithiophosphonate;
bis-(3-methyldimethoxysilyl-1-propyl)ethyldithiophosphonate;
3-methyldimethoxysilyl-1-propyldimethylthiophosphinate;
3-methyldimethoxysilyl-1-propyldiethylthiophosphinate;
3-triethoxysilyl-1-propylmethylthiosulphate;
3-triethoxysilyl-1-propylmethanethiosulphonate;
3-triethoxysilyl-1-propylethanethiosulphonate;
3-triethoxysilyl-1-propylbenzenethiosulphonate;
3-triethoxysilyl-1-propyltoluenethiosulphonate;
3-triethoxysilyl-1-propylnaphthalenethiosulphonate;
3-triethoxysilyl-1-propylxylenethiosulphonate;
triethoxysilylmethylmethylthiosulphate;
triethoxysilylmethylmethanethiosulphonate;
triethoxysilylmethylethanethiosulphonate;
triethoxysilylmethylbenzenethiosulphonate;
triethoxysilylmethyltoluenethiosulphonate;
triethoxysilylmethylnaphthalenethiosulphonate;
and triethoxysilylmethylxylenethiosulphonate.

84 more elements

Dependencies are inferred from the claim text.

Blocked mercaptosilane coupling agents for filled rubbers

Life of this patent

Blocked mercaptosilane coupling agents for filled rubbers

Life of this patent

Abstract

Claims66