Elastomeric composites containing modified fillers and functionalized elastomers

Patent metadata

Field	Value
Publication number	US-10640630-B2
Application number	US-201214381612-A
Country	US
Kind code	B2
Filing date	Mar 2, 2012
Priority date	Mar 2, 2012
Publication date	May 5, 2020
Grant date	May 5, 2020

Abstract

Elastomeric compositions are described which have at least one functionalized elastomer and at least one modified filler which has adsorbed and/or attached chemical groups, such as a triazole and/or pyrazole thereon, or other modified fillers which are also described. Methods are further described to improve hysteresis and/or abrasion resistance in elastomeric compositions containing a functionalized elastomer using the modified fillers of the present invention.

First claim

What is claimed is:

1. An elastomeric composition comprising at least one functionalized elastomer and at least one modified filler, wherein the modified filler comprises a filler having adsorbed thereon prior to contacting the modified filler with the functionalized elastomer:
a) at least one triazole;
b) at least one pyrazole; or
any combination thereof, wherein said modified filler improves abrasion resistance when present in the elastomeric composition compared to said filler that is not modified, wherein said filler is carbon black and said carbon black is present in the elastomeric composition in an amount of at least 40 phr.

2. The elastomeric composition of claim 1 , wherein a) or b) include a sulfur-containing substituent.

3. An elastomeric composition comprising at least one functionalized elastomer and at least one modified filler, wherein the modified filler comprises a filler having adsorbed thereon a triazole comprising formula (I) or formula (II):

or tautomers thereof;
wherein Z b is an alkylene group, where b is 0 or 1;
X, which is the same or different, is H, NH 2 , SH, NHNH 2 , CHO, COOR, COOH, CONR 2 , CN, CH 3 , OH, NDD′, or CF 3 ;
Y is H, or NH 2 ;
A is a functional group that is S k R, SSO 3 H, SO 2 NRR′, SO 2 SR, SNRR′, SNQ, SO 2 NQ, CO 2 NQ, S-(1,4-piperazinediyl)-SR, 2-(1,3-dithianyl), or 2-(1,3-dithiolanyl); or a linear, branched, aromatic, or cyclic hydrocarbon radical substituted with one or more of said functional group;
where R and R′, which are the same or different, are hydrogen; branched or unbranched C 1 -C 12 unsubstituted or substituted alkyl, alkenyl, alkynyl; unsubstituted or substituted aryl; unsubstituted or substituted heteroaryl; unsubstituted or substituted alkylaryl; unsubstituted or substituted arylalkyl, arylene, heteroarylene, or alkylarylene;
k is an integer from 1 to 8 when R is H and otherwise k is 2 to 8;
Q is (CH 2 ) w , (CH2) x O(CH 2 ) z , (CH 2 ) x NR(CH 2 ) z , or (CH 2 ) x S(CH 2 ) z , where x is 1 to 6, z is 1 to 6, and w is 2 to 6;
E is a polysulfur-containing group; and
said triazole comprising formula (II) is optionally N-substituted with an NDD′ substituent, where
D and D′, which are the same or different, are H or C 1 -C 4 alkyl.

4. The elastomeric composition of claim 3 , wherein the functionalized elastomer comprises a diene elastomer that is a copolymer of a diene and a vinyl aromatic compound, a copolymer of a diene and at least one alpha-olefin, polyisoprene, polybutadiene, chloroprene, polyisoprene, a copolymer of butadiene and isoprene, a copolymer of isobutylene and isoprene, a terpolymer of butadiene, a vinyl aromatic compound, and isoprene, or any combination thereof.

5. The elastomeric composition of claim 3 , wherein the functionalized elastomer is amine-functionalized, silane-functionalized, aminosilane-functionalized, mercaptosilane-functionalized, hydroxyl-functionalized, carboxylic-functionalized, epoxy-functionalized, tin-coupled, or any combination thereof.

6. The elastomeric composition of claim 3 , wherein the functionalized elastomer is an amine-functionalized styrene-butadiene rubber, silane-functionalized styrene-butadiene rubber, aminosilane-functionalized styrene-butadiene rubber, mercaptosilane-functionalized styrene-butadiene rubber, hydroxyl-functionalized styrene-butadiene rubber, carboxylic-functionalized styrene-butadiene rubber, epoxy-functionalized styrene-butadiene rubber, tin-coupled styrene-butadiene rubber, or any combination thereof.

7. The elastomeric composition of claim 3 , wherein said triazole comprises:

or tautomers thereof, and
E is S w , where w is 2 to 8, SSO, SSO 2 , SOSO 2 , SO 2 SO 2 .

8. The elastomeric composition of claim 3 , wherein said triazole comprises:

or tautomers thereof.

9. The elastomeric composition of claim 3 , wherein said triazole is:

or tautomers thereof, and
wherein Y is NH 2 .

10. The elastomeric composition of claim 3 , wherein said filler has adsorbed thereon: 3-amino-1,2,4-triazole-5-thiol, 3-amino-1,2,4-triazol-5-yl disulfide, 1,2,4-triazole-3-thiol, or 1,2,4-triazol-3-yl disulfide, or any combination thereof.

11. The elastomeric composition of claim 3 , further comprising at least one chemical group attached to said filler.

12. The elastomeric composition of claim 11 , wherein said chemical group comprises:
a) at least one triazole;
b) at least one pyrazole;
c) at least one imidazole; or
any combinations thereof.

13. The elastomeric composition of claim 12 , wherein said chemical group attached to said filler comprises the at least one triazole, the at least one triazole comprising:

or tautomers thereof;
wherein Z b is an alkylene group, where b is 0 or 1;
X comprises a bond to the filler;
Y is H, alkyl, aryl, or NH 2 ;
A is a functional group that is S k R, SSO 3 H, SO 2 NRR′, SO 2 SR, SNRR′, SNQ, SO 2 NQ, CO 2 NQ, S-(1,4-piperazinediyl)-SR, 2-(1,3-dithianyl), or 2-(1,3-dithiolanyl); or a linear, branched, aromatic, or cyclic hydrocarbon radical substituted with one or more of said functional group;
where R and R′, which are the same or different, are hydrogen; branched or unbranched C 1 -C 12 unsubstituted or substituted alkyl, alkenyl, alkynyl; unsubstituted or substituted aryl; unsubstituted or substituted heteroaryl; unsubstituted or substituted alkylaryl; unsubstituted or substituted arylalkyl, arylene, heteroarylene, or alkylarylene;
k is an integer from 1 to 8; and
Q is (CH 2 ) w , (CH2) x O(CH 2 ) z , (CH 2 ) x NR(CH 2 ) z , or (CH 2 ) x S(CH 2 ) z , where x is 1 to 6, z is 1 to 6, and w is 2 to 6.

14. The elastomeric composition of claim 13 , wherein said filler is at least one metal oxide and said X comprising a bond to the filler is through at least one silane linker group.

15. The elastomeric composition of claim 13 , wherein said filler is at least one metal oxide and said X comprising a bond to the filler is through at least one Si-containing group, Ti-containing group, Cr-containing group, or a Zr-containing group.

16. The elastomeric composition of claim 12 , wherein said chemical group attached to said filler comprises the at least one triazole, the at least one triazole comprising:

or tautomers thereof;
wherein Z b is an alkylene group, where b is 0 or 1;
at least one X comprises a bond to the filler, and any remaining X comprises a bond to the filler or a functional group;
A is a functional group that is S k R, SSO 3 H, SO 2 NRR′, SO 2 SR, SNRR′, SNQ, SO 2 NQ, CO 2 NQ, S-(1,4-piperazinediyl)-SR, 2-(1,3-dithianyl), or 2-(1,3-dithiolanyl); or a linear, branched, aromatic, or cyclic hydrocarbon radical substituted with one or more of said functional group;
where R and R′, which are the same or different, are hydrogen; branched or unbranched C 1 -C 12 unsubstituted

Assignees

• Belmont James A
• Tirumala Vijay R
• Zhang Ping
• Cabot Corp

Inventors

• Belmont James A
• Tirumala Vijay R
• Zhang Ping

Classifications

• C08K9/04 Primary

  Ingredients treated with organic substances {(treated with macromolecular compounds C08K9/08)} · CPC title

• C07D249/12

  Oxygen or sulfur atoms · CPC title

• B60C1/0016 Primary

  Compositions of the tread · CPC title

• C08K5/34

  Heterocyclic compounds having nitrogen in the ring · CPC title

• B60C1/0025

  Compositions of the sidewalls · CPC title