CA2430251A1 - Mineral-filled elastomer compositions - Google Patents

Mineral-filled elastomer compositions Download PDF

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Publication number
CA2430251A1
CA2430251A1 CA002430251A CA2430251A CA2430251A1 CA 2430251 A1 CA2430251 A1 CA 2430251A1 CA 002430251 A CA002430251 A CA 002430251A CA 2430251 A CA2430251 A CA 2430251A CA 2430251 A1 CA2430251 A1 CA 2430251A1
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Prior art keywords
thioacetate
triethoxysilyl
propyl
ethyl
group
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CA002430251A
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French (fr)
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CA2430251C (en
Inventor
Richard W. Cruse
Martin J. Hannon
Prashant G. Joshi
Frederick D. Osterholtz
Robert J. Pickwell
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General Electric Co
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Classifications

    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B60—VEHICLES IN GENERAL
    • B60C—VEHICLE TYRES; TYRE INFLATION; TYRE CHANGING; CONNECTING VALVES TO INFLATABLE ELASTIC BODIES IN GENERAL; DEVICES OR ARRANGEMENTS RELATED TO TYRES
    • B60C1/00—Tyres characterised by the chemical composition or the physical arrangement or mixture of the composition
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B60—VEHICLES IN GENERAL
    • B60C—VEHICLE TYRES; TYRE INFLATION; TYRE CHANGING; CONNECTING VALVES TO INFLATABLE ELASTIC BODIES IN GENERAL; DEVICES OR ARRANGEMENTS RELATED TO TYRES
    • B60C1/00—Tyres characterised by the chemical composition or the physical arrangement or mixture of the composition
    • B60C1/0016—Compositions of the tread
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/01—Use of inorganic substances as compounding ingredients characterized by their specific function
    • C08K3/013—Fillers, pigments or reinforcing additives
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
    • C08K5/37—Thiols
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/54—Silicon-containing compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/54—Silicon-containing compounds
    • C08K5/548—Silicon-containing compounds containing sulfur
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L21/00—Compositions of unspecified rubbers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L23/00—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
    • C08L23/02—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers not modified by chemical after-treatment
    • C08L23/16—Elastomeric ethene-propene or ethene-propene-diene copolymers, e.g. EPR and EPDM rubbers

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Mechanical Engineering (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Pigments, Carbon Blacks, Or Wood Stains (AREA)
  • Tires In General (AREA)

Abstract

A composition of matter is disclosed wherein the composition comprises: at least one latent mercaptosilane coupling agent; and at least one additional mercaptan. Preferable, the composition comprises: at least one sulfur vulcanizable rubber; at least one latent mercaptosilane coupling agent; at least one latent mercaptosilane activator; at least one filler; and, optionally, at least one additional mercaptosilane. A two pass process for preparing cured articles, such as tires and/or tire treads, which employs the composition is also disclosed.

Claims (20)

1. A composition of matter comprising:
A) at least one sulfur vulcanizable rubber;
B) at least one latent mercaptosilane coupling agent;
C) at least one latent mercaptosilane activator; and D) at least one filler.
2. The composition of claim 1 further comprising at least one additional mercaptan.
3. The composition of claim 1 wherein the sulfur vulcanizable rubber is selected from the group consisting of:
A) conjugated diene homopolymers and copolymers;
B) copolymers of at least one conjugated diene and at least one aromatic vinyl compound;
C) natural rubber; and D) ethylene-propylene copolymers and terpolymers.
4. The composition of claim 1 wherein the latent mercaptosilane coupling agent is selected from the group consisting of:
{{(ROC(=O)-)p(G-)j}k Y-S-}r G(-SiX3)s (1) and {(X3Si-)q G}a{Y{-S-G-SiX3}b}c (2) wherein :
R is a moiety comprising from 1 to 18 carbon atoms, which, in each occurrence is independently selected from the group consisting of hydrogen; straight, cyclic, or branched alkyl that may or may not contain unsaturation; alkenyl groups; aryl groups;
arenyl groups; and aralkyl groups;
each occurrence of G is independently a fragment, obtained by substitution of a quantity of hydrogen atoms given by p, of any hydrocarbon or oxa-, aza-, and/or cyano-substituted hydrocarbon, G 1, having from 1 to 18 carbon atoms.
with the proviso that if G is univalent, G can be a hydrogen atom;
each occurrence of X is a moiety independently selected from the group consisting of RO-, RC(=O)O-, R2C=NO-, R2NO- R2N-, -R, and -(OSiR2)t(OSiR3);
wherein each R and G is as described above and at least one X is not -R;
Y is a polyvalent species (Q)z A(=E);
each occurrence of Q is independently selected from the group consisting of oxygen, sulfur, and (-NR-);
each occurrence of A is independently selected from the group consisting of carbon, sulfur, phosphorus, and sulfonyl;
each occurrence of E is independently selected from the group consisting of oxygen, sulfur, and NR; and the following variables are integers, each occurrence of which is independent:
a is 0 to 7;
b is 1 to 3;
c is 1 to 6;
j is 0 to 1, but is 0 only if p is 1;

k is 1 to 2;
p is 0 to 5;
q is 0 to 6;
r is 1 to 3;
s is 1 to 3;
t is 0 to 5; and z is 0 to 2;
provided that:
(1) if j is 0, then p is 1;
(2) if A is carbon, sulfur, or sulfonyl, then:
(i) at least one of a and c is equal to 1;
(ii) a + b = 2; and (iii) k = 1;
(3) if A is phosphorus, then (i) the value of a does not exceed 2c; and (ii) k = 2.
5. The composition of claim 4 wherein Y is -C(=O)-.
6. The composition of claim 4 wherein each X is RO-, the silane is of formula (1), r=1, and s=1.
7. The composition of claim 4 wherein G is -(CH2)n wherein n is 1 to 12.
8. The composition of claim 1 wherein the latent mercaptosilane coupling agent 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; triethoxysilyhnethyl 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;
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 thiooctoate;
3-triethoxysilyl-1-propyl thiopalmitate; 3-triethoxysilyl-1-propyl thiooctoate;
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-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)tetrathiophosphate;
bis-(3-triethoxysilyl-1-propyl)methyltrithiophosphonate;
bis-(3-triethoxysilyl-1-propyl)ethyltrithiophosphonate;
3-triethoxysilyl-1-propyldimethyldithiophosphinate;
3-triethoxysilyl-1-propyldiethyldithiophosphinate;
tris-(3-methyldimethoxysilyl-1-propyl)trithiopho sphate;
bis-(3-methyldimethoxysilyl-1-propyl)methyldithiophosphonate;
bis-(3-methyldimethoxysilyl-1-propyl)ethyldithiophosphonate;
3-methyldimethoxysilyl-1-propyldimethylthiophosphinate;
3 -methyldimethoxysilyl-1-propyldiethylthiophosphinate;
3-triethoxysilyl-1-propyhnethylthiosulphate;
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.
9. The composition of claim 1 wherein the latent-mercaptosilane activator is selected from the group consisting of:
{U(=Z)q-Z-}c (5) R-Z-{U(=Z)q-Z-}m R (6) and {R-Z-{U(-Z)q-Z d-}g}c L (7) wherein:
each Z is independently selected from the group consisting of an oxygen atom, NH, and NR;
each M is independently selected from the group consisting of a hydrogen atom and R;
each R is chosen independently from hydrogen, straight, cyclic, or branched alkyl that may or may not contain unsaturation, allcenyl groups, aryl groups, and aralkyl groups, with each R containing from 1 to 18 carbon atoms;

each U is independently a fragment, obtained by substitution of a quantity of hydrogen atoms given by 2q+2, of ably hydrocarbon or oxa-, aza-, and/or cyano-substituted hydrocarbon, U1, having from 1 to 30 carbon atoms;

each L is independently a fragment, obtained by substitution of a quantity of hydrogen atoms given by c, of any hydrocarbon or oxa-, aza-, and/or cyano-substituted hydrocarbon, L1, having from 1 to 30 carbon atoms;

m is an integer of from 0 to 500;

c is 1 to 6; and q is O to 6.
10. The composition of claim 2 wherein the additional mercaptan is selected from the group consisting of compounds of the structure (HS-)r G(-SiX3)t.
11. The composition of claim 10 wherein the additional mercaptan is selected from the group consisting of 3-mercapto-1-propyltriethoxysilane, 2-mercapto-1-ethyltriethoxysilane, mercaptomethyltriethoxysilane, 8-mercapto-1-octyltriethoxysilane, 10-mercapto-1-decyltriethoxysilane, 1-mercapto-1-ethyltriethoxysilane, 3-mercapto-1-propylmethyldiethoxysilane, 3-mercapto-1-propyldimethylethoxysilane, 3-mercapto-1-propyltrimethoxysilane, 2-mercapto-1-ethyltrimethoxysilane, mercaptomethyltrimethoxysilane, 8-mercapto-1-octyltrimethoxysilane, 10-mercapto-1-decyltrimethoxysilane, 1-mercapto-1-ethyltrimethoxysilane, 3-mercapto-1-propylmethyldimethoxysilane, 3-mercapto-1-propyldimethylmethoxysilane, 3-mercapto-1-propyltripropoxysilane, 3-mercapto-1-propyltriisopropoxysilane, 3-mercapto-1-propyltributoxysilane, and mixtures of the foregoing.
12. A process for the preparation of a rubber composition consisting essentially of the steps of:

A) thermomechanically mixing in a first pass:

1) at least one sulfur vulcanizable rubber;
2) at least one latent mercaptosilane coupling agent; and 3) at least one filler; and, optionally, 4) at least one additional mercaptan;

B) bringing the temperature of the first pass mix from about 140° C to about 200° C over a period of 1 to 20 minutes;
thereby forming a nonproductive first mixture;

C) thermomechanically mixing the nonproductive first mixture in a second pass, optionally in the presence of at least one curing agent, at a temperature of from about 25 to about 100° C for a period of from about 1 to about 30 minutes; thereby forming a productive second mixture;

D) adding at least one latent-mercaptosilane activator in step A), step C), or both step A) and step C);

E) shaping the second mixture; and then F) curing the second mixture at a temperature between about 130° C to about 200° C for a period of from about 5 to about 60 minutes.
13. The process of claim 12 wherein the filler in step A) is pre-treated with at least a portion of the latent-mercaptosilane coupling agent.
14. The process of claim 12 wherein the sulfur vulcanizable rubber is selected from the group consisting of:

A) conjugated dime homopolymers and copolymers;
B) copolymers of at least one conjugated dime and at least one aromatic vinyl compound;
C) natural rubber; and D) ethylene-propylene copolymers and terpolymers
15. The process of claim 12 wherein the latent mercaptosilane coupling agent is selected from the group consisting of:

{{(ROC(=O)-)p(G-)j}k Y-S-}r G(-SiX3)s (1) and {(X3Si-)q G}a{Y{-S-G-SiX3}b}c (2) wherein:

R is a moiety comprising from 1 to 18 carbon atoms, which, in each occurrence is independently selected from the group consisting of hydrogen; straight, cyclic, or branched alkyl that may or may not contain unsaturation; alkenyl groups; aryl groups;
arenyl groups; and aralkyl groups;

each occurrence of G is independently a fragment, obtained by substitution of a quantity of hydrogen atoms given by p, of any hydrocarbon or oxa-, aza-, and/or cyano-substituted hydrocarbon, G1, having from 1 to 18 carbon atoms.

with the proviso that if G is univalent, G can be a hydrogen atom;

each occurrence of X is a moiety independently selected from the group consisting of RO-, RC(=O)O-, R2C=NO-, R2NO- R2N-, -R, and -(OSiR2)t(OSiR3);

wherein each R and G is as described above and at least one X is not -R;

Y is a polyvalent species (Q)z A(=E);

each occurrence of Q is independently selected from the group consisting of oxygen, sulfur, and (-NR-);

each occurrence of A is independently selected from the group consisting of carbon, sulfur, phosphorus, and sulfonyl;

each occurrence of E is independently selected from the group consisting of oxygen, sulfur, and NR; and the following variables are integers, each occurrence of which is independent:

a is 0 to 7;
b is 1 to 3;
c is 1 to 6;
j is 0 to 1, but is 0 only if p is 1;
k is 1 to 2;
p is 0 to 5;
q is 0 to 6;
r is 1 to 3;
s is 1 to 3;
t is 0 to 5; and z is 0 to 2;

provided that:

(1) if j is 0, then p is 1;

(2) if A is carbon, sulfur, or sulfonyl, then:

(iv) at least one of a and c is equal to 1;
(v) a + b = 2; and (vi) k = 1;

(3) if A is phosphorus, then (iii) the value of a does not exceed 2c; and (iv) k = 2.
16. The process of claim 12 wherein Y is -C(=O)-.
17. The process of claim 12 wherein the latent mercaptosilane coupling agent 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;

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 thiooctoate;

3-triethoxysilyl-1-propyl thiopalmitate; 3-triethoxysilyl-1-propyl thiooctoate;

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-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)tetrathiophosphate;

bis-(3-triethoxysilyl-1-propyl)methyltrithiophosphonate;

bis-(3-triethoxysilyl-1-propyl)ethyltrithiophosphonate;

3-triethoxysilyl-1-propyldimethyldithiophosphinate;

3-triethoxysilyl-1-propyldiethyldithiophosphinate;

tris-(3-methyldimethoxysilyl-1-propyl)tritluophosphate;

bis-(3-methyldimethoxysilyl-1-propyl)methyldithiophosphonate;

bis-(3-methyldimethoxysilyl-1-propyl)ethyldithiophosphonate;

3-methyldimethoxysilyl-1-propyldimethylthiophosphinate;

3-methyldimethoxysilyl-1-propyldiethylthiophosphinate;

3-triethoxysilyl-1-propymethylthiosulphate;

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.
18. The process of claim 12 wherein the latent-mercaptosilane activator is selected from the group consisting of:

{U(=Z)q-Z-)c (5) R-Z-{U(=Z)q-Z-}m R (6) and {R-Z-{U(=Z)q-Z d-}g}c}L (7) wherein:

each Z is independently selected from the group consisting of an oxygen atom, NH, and NR;

each M is independently selected from the group consisting of a hydrogen atom and R;

each R is chosen independently from hydrogen, straight, cyclic, or branched alkyl that may or may not contain unsaturation, alkenyl groups, aryl groups, and aralkyl groups, with each R containing from 1 to 18 carbon atoms;

each U is independently a fragment, obtained by substitution of a quantity of hydrogen atoms given by 2q+2, of any hydrocarbon or oxa-, aza-, and/or cyano-substituted hydrocarbon, U1, having from 1 to 30 carbon atoms;

each L is independently a fragment, obtained by substitution of a quantity of hydrogen atoms given by c, of any hydrocarbon or oxa-, aza-, and/or cyano-substituted hydrocarbon, L1, having from 1 to 30 carbon atoms;

m is an integer of from 0 to 500;

c is 1 to 6; and q is 0 to 6.
19. The process of claim 12 wherein the additional mercaptosilane is selected from the group consisting of compounds of the structure (HS-)r G(-SiX3)t
20. A tire comprising a cured composition of matter comprising:
A) at least one sulfur vulcanizable rubber;
B) at least one latent mercaptosilane coupling agent;
C) at least one latent-mercaptosilane activator; and D) at least one filler.
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US20020115767A1 (en) 2002-08-22
US6635700B2 (en) 2003-10-21
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CA2430251C (en) 2011-05-31
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ES2278816T3 (en) 2007-08-16
PT1341843E (en) 2007-02-28

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