Back to results
US 7,629,430 B2Granted
Hybrid silicon-containing coupling agents for filled elastomer compositions
AssigneeMomentive Performance Materials Inc.
InventorRichard W. Cruse
Life of this patent
Estimating the term…
Abstract
This invention describes novel chemical compounds whose structures are hybrids between sulfur-containing and non-sulfur-containing silanes wherein the two types of silanes are linked by siloxane bonds. The invention includes methods of preparation for the hybrid silanes as well as their use in filled rubbers as coupling agents. The hybrid silanes described are unique in that a certain amount of water in their preparation leads to superior performance in their intended application, and that they can thus be produced more efficiently and safely than coupling agents currently used in the art, from readily available hydrated raw materials.
Claims21
A hybrid silane composition comprising a mixture of compounds corresponding to the general formula:
- F1rF2s Formula (I)
- wherein
- r is 0 to 10,000;
- s is 0 to 10,000;
- with the proviso that r has a value of 1 to 2 and s has a value of 1 to 3 for at least one compound of Formula (I) in the mixture of compounds;
- F1 is a sulfur silane structure selected from the group consisting of:
- {(R1O)3-m-n[(—O—)0.5]mR2nSi-G1-Sx—(C=E)y-Ez}p-G2 Formula (II)
- and
- {(R1O)3-m-n[(—O—)0.5]mR2nSi-G1-Sx—}2(C=E)y Formula (III)
- wherein
- each occurrence of R1 and R2 is independently hydrogen, or any group which can be obtained by removal of one hydrogen atom from a hydrocarbon group having from 1 to 20 carbon atoms, including branched or straight chain alkyl, alkenyl, aryl or aralkyl groups;
- each occurrence of G1 is any group which can be obtained by removal of a quantity of two hydrogen atoms from any hydrocarbon having from 1 to 20 carbon atoms;
- each occurrence of G2 is independently a hydrogen atom or any group which can be obtained by removal of a quantity of p hydrogen atoms from any hydrocarbon having from 1 to 20 carbon atoms;
- S is sulfur;
- O is oxygen;
- Si is silicon;
- each occurrence of E is independently oxygen or Sx;
- each occurrence of m can be 1 or 2 and n can be 0, 1 or 2;
- each occurrence of p is independently 1 to 4;
- each occurrence of y is 1 and z is independently 0 or 1;
- and
- each occurrence of x is independently 1 to 8;
- F2 is a nonsulfur silane structure represented by the general formula:
- (R1O)4-m′-n′[(—O—)0.5]m′R3n′Si Formula (IV)
- wherein
- each occurrence of R1 is as defined above;
- each occurrence of R3 is independently hydrogen, or a hydrocarbon group of 1 to 20 carbon atoms including aryl as well as branched or straight chain alkyl, alkenyl, arenyl, or aralkyl groups;
- and each occurrence of m′ can be 1, 2 or 3 and n′ can be 0, 1, 2 or 3.
25 more elements
A process of making a hybrid silane composition comprising the steps of hydrolyzing a sulfur silane and a nonsulfur silane in the presence of water to effect partial hydrolysis of silane alkoxy groups on each of the sulfur silane and nonsulfur silane, and bonding the partially hydrolyzed sulfur silane and nonsulfur silane to each other via Si—O—Si linkages, said hybrid silane composition comprising a mixture of compounds corresponding to the general formula:
- F1rF2s Formula (I)
- wherein
- r is 0 to 10,000;
- s is 0 to 10,000;
- with the proviso that r has a value of 1 to 2 and s has a value of 1 to 3 for at least one compound of Formula (I) in the mixture of compounds;
- F1 is a sulfur silane structure selected from the group consisting of:
- {(R1O)3-m-n[(—O—)0.5]mR2nSi-G1-Sx—(C=E)y-Ez}p-G2 Formula (II)
- and
- {(R1O)3-m-n[(—O—)0.5]mR2nSi-G1-Sx—}2(C=E)y Formula (III)
- wherein
- each occurrence of R1 and R2 is independently hydrogen, or any group which can be obtained by removal of one hydrogen atom from a hydrocarbon group having from 1 to 20 carbon atoms, including branched or straight chain alkyl, alkenyl, aryl or aralkyl groups;
- each occurrence of G1 is any group which can be obtained by removal of a quantity of two hydrogen atoms from any hydrocarbon having from 1 to 20 carbon atoms;
- each occurrence of G2 is independently a hydrogen atom or any group which can be obtained by removal of a quantity of p hydrogen atoms from any hydrocarbon having from 1 to 20 carbon atoms;
- S is sulfur;
- O is oxygen;
- Si is silicon;
- each occurrence of E is independently oxygen or Sx;
- each occurrence of m is 1 or 2 and n is 0, 1 or 2;
- each occurrence of p is independently 1 to 4;
- each occurrence of y is 1 and z is independently 0 or 1;
- and
- each occurrence of x is independently 1 to 8;
- F2 is a nonsulfur silane structure represented by the general formula:
- (R1O)4-m′-n′[(—O—)0.5]m′R3n′Si Formula (IV)
- wherein
- each occurrence of R1 is as defined above;
- each occurrence of R3 is independently hydrogen, or a hydrocarbon group of 1 to 20 carbon atoms including aryl as well as branched or straight chain alkyl, alkenyl, arenyl, or aralkyl groups;
- and
- each occurrence of m′ can be 1, 2 or 3 and n′ can be 0, 1, 2 or 3.
26 more elements
A composition comprising:
- polymer;
- filler;
- and a hybrid silane composition which comprises a mixture of compounds corresponding to the general formula:
- F1rF2s Formula (I)
- wherein
- r is 0 to 10,000;
- s is 0 to 10,000;
- with the proviso that r has a value of 1 to 2 and s has a value of 1 to 3 for at least one compound of Formula (I) in the mixture of compounds;
- F1 is a sulfur silane structure selected from the group consisting of:
- {(R1O)3-m-n[(—O—)0.5]mR2nSi-G1-Sx—(C=E)y-Ez}p-G2 Formula (II)
- and
- {(R1O)3-m-n[(—O—)0.5]mR2nSi-G1-Sx—}2(C=E)y Formula (III)
- wherein
- each occurrence of R1 and R2 is independently hydrogen, or any group which can be obtained by removal of one hydrogen atom from a hydrocarbon group having from 1 to 20 carbon atoms, including branched or straight chain alkyl, alkenyl, aryl or aralkyl groups;
- each occurrence of G1 is any group which can be obtained by removal of a quantity of two hydrogen atoms from any hydrocarbon having from 1 to 20 carbon atoms;
- each occurrence of G2 is independently a hydrogen atom or any group which can be obtained by removal of a quantity of p hydrogen atoms from any hydrocarbon having from 1 to 20 carbon atoms;
- S is sulfur;
- O is oxygen;
- Si is silicon;
- each occurrence of E is independently oxygen or Sx;
- each occurrence of m is 1 or 2 and n is 0, 1 or 2;
- each occurrence of p is independently 1 to 4;
- each occurrence of y is 1 and z is independently 0 or 1;
- and
- each occurrence of x is independently 1 to 8;
- F2 is a nonsulfur silane structure represented by the general formula:
- (R1O)4-m′-n′[(—O—)0.5]m′R3n′Si Formula (IV)
- wherein
- each occurrence of R1 is as defined above;
- each occurrence of R3 is independently hydrogen, or a hydrocarbon group of 1 to 20 carbon atoms including aryl as well as branched or straight chain alkyl, alkenyl, arenyl, or aralkyl groups;
- and
- each occurrence of m′ can be 1, 2 or 3 and n′ can be 0, 1, 2 or 3.
29 more elements
A process of making a sulfur vulcanized rubber product which comprises:
- mixing sulfur vulcanizable rubber, filler and a hybrid silane composition to form a mixture, said hybrid silane composition comprising a mixture of compounds corresponding to the general formula:
- F1rF2s Formula (I)
- wherein
- r is 0 to 10,000;
- s is 0 to 10,000;
- with the proviso that r has a value of 1 to 2 and s has a value of 1 to 3 for at least one compound of Formula (I) in the mixture of compounds;
- F1 is a sulfur silane structure selected from the group consisting of:
- {(R1O)3-m-n[(—O—)0.5]mR2nSi-G1-Sx—(C=E)y-Ez}p-G2 Formula (II)
- and
- {(R1O)3-m-n[(—O—)0.5]mR2nSi-G1-Sx—}2(C=E)y Formula (III)
- wherein
- each occurrence of R1 and R2 is independently hydrogen, or any group which can be obtained by removal of one hydrogen atom from a hydrocarbon group having from 1 to 20 carbon atoms, including branched or straight chain alkyl, alkenyl, aryl or aralkyl groups;
- each occurrence of G1 is any group which can be obtained by removal of a quantity of two hydrogen atoms from any hydrocarbon having from 1 to 20 carbon atoms;
- each occurrence of G2 is independently a hydrogen atom or any group which can be obtained by removal of a quantity of p hydrogen atoms from any hydrocarbon having from 1 to 20 carbon atoms;
- S is sulfur;
- O is oxygen;
- Si is silicon;
- each occurrence of E is independently oxygen or Sx;
- each occurrence of m is 1 or 2 and n is 0, 1 or 2;
- each occurrence of p is independently 1 to 4;
- each occurrence of y is 1 and z is independently 0 or 1;
- and
- each occurrence of x is independently 1 to 8;
- F2 is a nonsulfur silane structure represented by the general formula:
- (R1O)4-m′-n′[(—O—)0.5]m′R3n′Si Formula (IV)
- wherein
- each occurrence of R1 is as defined above;
- each occurrence of R3 is independently hydrogen, or a hydrocarbon group of 1 to 20 carbon atoms including aryl as well as branched or straight chain alkyl, alkenyl, arenyl, or aralkyl groups;
- and
- each occurrence of m′ can be 1, 2 or 3 and n′ can be 0, 1, 2 or 3;
- and
- curing the mixture in the presence of a sulfur source to provide the sulfur vulcanized rubber product.
29 more elements
Dependencies are inferred from the claim text.