Silane compound and composition thereof
The invention provides a silane compound for obtaining a cross-linked product which hardly generates poor dispersion or adhesion between an organic polymer material and an inorganic material and exhibits excellent viscoelastic properties or adhesive properties, or a composition comprising the silane compound. In particular, the invention provides a silane compound represented by formula (1): wherein R 1 , R 2 , and R 3 each independently represents a hydrocarbon group optionally containing an oxygen atom or a nitrogen atom, or a hydrogen atom; L represents a hydrocarbon group optionally containing at least one heteroatom selected from the group consisting of nitrogen, oxygen, and sulfur; and the other variables are as defined herein.
1. A silane compound represented by formula (1):
wherein
R 1 , R 2 , and R 3 each independently represents a hydrocarbon group optionally containing an oxygen atom or a nitrogen atom, or a hydrogen atom;
L represents a hydrocarbon group optionally containing at least one heteroatom selected from the group consisting of nitrogen, oxygen, and sulfur;
a is an integer of 0 or 1;
b is an integer of 0 or 1;
c is each independently an integer of 0 or 1;
d is each independently an integer of 0 or 1;
e is an integer from 0 to 5;
R 4 , R 5 , R 6 , and R 7 represent a hydrogen atom, a methyl group, or an alkyl group having 2 to 10 carbons, or one of R 4 or R 5 and R 6 or R 7 may form a cross-linked structure represented by —(CH 2 ) f —, and f is an integer from 1 to 5;
R 8 , R 9 , R 10 and R 11 represent a hydrogen atom, a methyl group or an alkyl group having 2 to 10 carbons, or one of R 8 or R 9 and R 10 or R 11 may form a cross-linked structure represented by —(CH 2 ) g —, g is an integer from 1 to 5, R 16 is a hydrogen atom, a methyl group or an alkyl group having 2 to 8 carbons and R 17 is a hydrogen atom, a methyl group or an alkyl group having 2 to 10 carbons, where R 12 and R 13 bond to each other to form a double bond and R 14 , R 15 , and R 18 are a hydrogen atom, a methyl group or an alkyl group having 2 to 10 carbons, or R 14 and R 15 bond to each other to form a double bond and R 12 , R 13 , and R 18 are a hydrogen atom, a methyl group or an alkyl group having 2 to 10 carbons; or
R 16 and R 17 may bond to each other to form a 4 to 9 membered alicyclic hydrocarbon, where R 14 and R 15 bond to each other to form a double bond and R 12 , R 13 , and R 18 are a hydrogen atom, a methyl group or an alkyl group having 2 to 10 carbons.
2. The silane compound according to claim 1 , represented by formula (2):
wherein
R 1 , R 2 , and R 3 each independently represents a hydrocarbon group optionally containing an oxygen atom or a nitrogen atom, or a hydrogen atom;
h is an integer from 1 to 10;
a is an integer of 0 or 1;
b is an integer of 0 or 1;
c is each independently an integer of 0 or 1;
d is each independently an integer of 0 or 1;
e is an integer from 0 to 5;
R 4 , R 5 , R 6 , and R 7 represent a hydrogen atom, a methyl group, or an alkyl group having 2 to 10 carbons, or one of R 4 or R 5 and R 6 or R 7 may form a cross-linked structure represented by —(CH 2 ) f —, and f is an integer from 1 to 5;
R 8 , R 9 , R 10 and R 11 represent a hydrogen atom, a methyl group or an alkyl group having 2 to 10 carbons, or one of R 8 or R 9 and R 10 or R 11 may form a cross-linked structure represented by —(CH 2 ) g —, g is an integer from 1 to 5, R 16 is a hydrogen atom, a methyl group or an alkyl group having 2 to 8 carbons, R 17 is a hydrogen atom, a methyl group or an alkyl group having 2 to 10 carbons; where R 12 and R 13 bond to each other to form a double bond and R 14 , R 15 , and R 18 are a hydrogen atom, a methyl group or an alkyl group having 2 to 10 carbons, or R 14 and R 15 bond to each other to form a double bond and R 12 , R 13 , and R 18 are a hydrogen atom, a methyl group or an alkyl group having 2 to 10 carbons; or
R 16 and R 17 may bond to each other to form a 4 to 9 membered alicyclic hydrocarbon, where R 14 and R 15 bond to each other to form a double bond and R 12 , R 13 , and R 18 are a hydrogen atom, a methyl group or an alkyl group having 2 to 10 carbons.
3. The silane compound according to claim 1 , represented by formula (3):
wherein
R 1 , R 2 , and R 3 each independently represents a hydrocarbon group optionally containing an oxygen atom or a nitrogen atom, or a hydrogen atom;
h is an integer from 1 to 10;
a is an integer of 0 or 1;
b is an integer of 0 or 1;
c is each independently an integer of 0 or 1;
d is each independently an integer of 0 or 1;
e is an integer from 0 to 5;
R 4 , R 5 , R 6 , and R 7 represent a hydrogen atom, a methyl group, or an alkyl group having 2 to 10 carbons, or one of R 4 or R 5 and R 6 or R 7 may form a cross-linked structure represented by —(CH 2 ) f —, and f is an integer from 1 to 5;
R 8 , R 9 , R 10 and R 11 represent a hydrogen atom, a methyl group or an alkyl group having 2 to 10 carbons, or one of R 8 or R 9 and R 10 or R 11 may form a cross-linked structure represented by —(CH 2 ) g —, g is an integer from 1 to 5, and is a hydrogen atom, a methyl group or an alkyl group having 2 to 8 carbons.
4. The silane compound according to claim 1 , represented by formula (4):
wherein
R 1 , R 2 , and R 3 each independently represents a hydrocarbon group optionally containing an oxygen atom or a nitrogen atom, or a hydrogen atom;
h is an integer from 1 to 10;
a is an integer of 0 or 1;
b is an integer of 0 or 1;
c is each independently an integer of 0 or 1;
d is each independently an integer of 0 or 1;
e is an integer from 0 to 5;
R 4 , R 5 , R 6 , and R 7 represent a hydrogen atom, a methyl group, or an alkyl group having 2 to 10 carbons, or one of R 4 or R 5 and R 6 or R 7 may form a cross-linked structure represented by —(CH 2 ) f —, and f is an integer from 1 to 5;
R 8 , R 9 , R 10 and R 11 represent a hydrogen atom, a methyl group or an alkyl group having 2 to 10 carbons, or one of R 8 or R 9 and R 10 or R 11 may form a cross-linked structure represented by —(CH 2 ) g —, g is an integer from 1 to 5, and R 32 is a hydrogen atom, a methyl group or an alkyl group having 2 to 9 carbons.
5. The silane compound according to claim 1 , represented by formula (5):
wherein
R 1 , R 2 , and R 3 each independently represents a hydrocarbon group optionally containing an oxygen atom or a nitrogen atom, or a hydrogen atom;
h is an integer from 1 to 10;
a is an integer of 0 or 1;
b is an integer of 0 or 1;
c is each independently an integer of 0 or 1;
d is each independently an integer of 0 or 1;
e is an integer from 0 to 5;
R 4 , R 5 , R 6 , and R 7 represent a hydrogen atom, a methyl group, or an alkyl group having 2 to 10 carbons, or one of R 4 or R 5 and R 6 or R 7 may form a cross-linked structure represented by —(CH 2 ) f —, and f is an integer from 1 to 5;
R 8 , R 9 , R 10 and R 11 represent a hydrogen atom, a methyl group or an alkyl group having 2 to 10 carbons, or one of R 8 or R 9 and R 10 or R 11 may form a cross-linked structure represented by —(CH 2 ) g —, g is an integer from 1 to 5, and x is an integer from 0 to 5.
6. The silane compound according to claim 1 , represented by formula (6):
wherein R 1 , R 2 , and R 3 each independently represents a hydrocarbon group optionally containing an oxygen atom or a nitrogen atom, or a hydrogen atom; or
by formula (7):
wherein R 1 , R 2 , and R 3 each independently represents a hydrocarbon group optionally containing an oxygen atom or a nitrogen atom, or a hydrogen atom; or
by formula (8):
wherein R 1 , R 2 , and R 3 each independently represents a hydrocarbon group optionally containing an oxygen atom or a nitrogen atom, or a hydrogen atom; or
by formula (9):
wherein R 1 , R 2 , and R 3 each independently represents a hydrocarbon group optionally containing an oxygen atom or a nitrogen atom, or a hydrogen atom.
7. The silane compound according to claim 1 , wherein
R 1 R 2 R 3 Si group in the silane compound has a chemical structure of formula (10):
wherein
R 19 each independently represents an alkoxy group or an amino group substituted with one or more alkyl groups;
R 20 each independently represents a hydrogen atom or an alkyl group;
L 1 each independently represents a hydrocarbon group optionally including at least one hetero atom selected from the group consisting of nitrogen, oxygen, and sulfur;
j is independently an integer of 0 or 1;
k is an integer of 1 to 3; and
an asterisk (*) indicates a region bonded to a moiety other than a silyl group of the silane compound.
8. The silane compound according to claim 1 , wherein R 1 R 2 R 3 Si group in the silane compound is a triethoxysilyl group.
9. A composition comprising the silane compound according to claim 1 and a polymer that is capable of reacting with the silane compound.
10. The composition according to claim 9 , wherein the polymer is an elastomer having a glass transition point of 25° C. or lower and further comprises an inorganic material.
11. The composition according to claim 10 , wherein the elastomer having a glass transition point of 25° C. or lower comprises at least one substance selected from the group consisting of natural rubber, butadiene rubber, nitrile rubber, silicone rubber, isoprene rubber, styrene-butadiene rubber, isoprene-butadiene rubber, styrene-isoprene-butadiene rubber, ethylene-propylene-diene rubber, halogenated butyl rubber, halogenated isoprene rubber, halogenated isobutyrene copolymer, chloroprene rubber, butyl rubber, and halogenated isobutyrene-p-methyl styrene rubber.
12. The composition according to claim 10 , wherein the elastomer having a glass transition point of 25° C. or lower has a double bond in the main chain.
13. The composition according to claim 10 , wherein the elastomer having a glass transition point of 25° C. or lower comprises at least one monomer unit selected from the group consisting of styrene, butadiene, isoprene, and isobutylene.
14. The composition according to claim 10 , wherein the elastomer having a glass transition point of 25° C. or lower is selected from the group consisting of styrene butadiene rubber, butadiene rubber, isoprene rubber, butyl rubber, nitrile butadiene rubber, and natural rubber.
15. The composition according to claim 10 , wherein the total content of the silane compound in the composition is 0.1 to 30 parts by mass with respect to 100 parts by mass of the elastomer.
16. The composition according to claim 10 , further comprising a silane compound other than the compound represented by said formula (1).
17. The composition according to claim 16 , wherein
the silane compound other than the compound represented by said formula (1) is a silane compound represented by formula (11):
wherein
t and v are each independently an integer from 0 to 10;
u is an integer from 2 to 10;
q and r are each independently an integer from 1 to 3;
w and z are each independently an integer of 0 or 1;
L 2 and L 3 are each independently a hydrocarbon group optionally containing at least one heteroatom selected from the group consisting of nitrogen, oxygen, and sulfur;
R 21 and R 23 are each independently an alkoxy group or an amino group substituted with one or more alkyl groups; and
R 22 and R 24 are each independently a hydrogen atom or an alkyl group.
18. The composition according to claim 16 , wherein the proportion of the content of the silane compound other than the compound represented by said formula (1) in the composition with respect to the total content of the silane compound in the composition is 0.1 to 0.9 on a mass basis.
19. A cross-linked product of the composition according to claim 10 .
20. A tire comprising the cross-linked product according to claim 19 .