CA2419986A1 - Hydrocarbon core polysulfide silane coupling agents for filled elastomer compositions - Google Patents
Hydrocarbon core polysulfide silane coupling agents for filled elastomer compositions Download PDFInfo
- Publication number
- CA2419986A1 CA2419986A1 CA002419986A CA2419986A CA2419986A1 CA 2419986 A1 CA2419986 A1 CA 2419986A1 CA 002419986 A CA002419986 A CA 002419986A CA 2419986 A CA2419986 A CA 2419986A CA 2419986 A1 CA2419986 A1 CA 2419986A1
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- CA
- Canada
- Prior art keywords
- hydrocarbon
- polysulfide silane
- fragment obtained
- composition
- mercaptan
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic System
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
-
- 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
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic System
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
Abstract
The present invention discloses novel hydrocarbon core polysulfide silanes a nd methods of preparing the hydrocarbon core polysulfide silanes. Preferably, t he silanes of the present invention contain assemblies of a single unit of a hydrolyzable silane group, tethered to one end of a chain of sulfur atoms, a nd several of these assemblies are bound to a common central hydrophobic core v ia the outer end of the sulfur atoms chain. The hydrocarbon core polysulfide silanes may be incorporated into filled elastomeric compositions providing improved dispersibility of the filler materials. Mineral fillers may be pre- treated with the hydrocarbon core polysulfide silanes prior to use in elastomeric compositions.
Claims (41)
1. A polysulfide silane composition having the formula:
(X1X2X3Si-J-S x-)p-G
wherein p is 3 to 12, x is 2 to 20, X1 is a hydrolyzable functionality selected from the group consisting of -Cl, -Br, -OH, -O-N=C(R)2, -OR, and RC(=O)O-, in which R is a hydrocarbon fragment obtained by removing one hydrogen atom from a hydrocarbon having 1 to 20 carbon atoms, X2 and X3 are X1, R or H, J is a hydrocarbon fragment obtained by removal of one hydrogen atom of R, and G is a hydrocarbon fragment obtained by removal of a p quantity of hydrogen atoms of a hydrocarbon having from 1 to 30 carbon atoms.
(X1X2X3Si-J-S x-)p-G
wherein p is 3 to 12, x is 2 to 20, X1 is a hydrolyzable functionality selected from the group consisting of -Cl, -Br, -OH, -O-N=C(R)2, -OR, and RC(=O)O-, in which R is a hydrocarbon fragment obtained by removing one hydrogen atom from a hydrocarbon having 1 to 20 carbon atoms, X2 and X3 are X1, R or H, J is a hydrocarbon fragment obtained by removal of one hydrogen atom of R, and G is a hydrocarbon fragment obtained by removal of a p quantity of hydrogen atoms of a hydrocarbon having from 1 to 30 carbon atoms.
2. The polysulfide silane composition of claim 1 wherein X1, X2 and X3 are the same hydrolyzable functionalities.
3. The polysulfide silane composition of claim 1 wherein X1, X2 and X3 are ethoxy.
4. The polysulfide silane composition of claim 1 wherein X1, X2 and X3 are each different hydrolyzable functionalities.
5. The polysulfide silane composition of claim 1 wherein p is 3 to 6.
6. The polysulfide silane composition of claim 1 wherein x is 2 to 8.
7. The polysulfide silane composition of claim 1 wherein R is a hydrocarbon moiety selected from the group consisting of straight chain alkyl, alkenyl, aryl and aralkyl groups.
8. The polysulfide silane composition of claim 1 wherein J is selected from the group consisting of methylene, ethylene, propylene, isobutylene, and diradicals obtained by loss of hydrogen atoms at a 2,4 or 2,5 position of norbornane, an alpha position of 2-norbornylethane, a beta position of 2-norbornylethane, a 4 position of 2-norbornylethane, or a 5 position of 2-norbornylethane.
9. The polysulfide silane composition of claim 1 wherein p is 3 and G is glyceryl.
10. The polysulfide silane composition of claim 1 wherein p is 3 and G is a hydrocarbon fragment obtained by removal of 3 hydrogen atoms from 2-norbornylethane.
11. The polysulfide silane composition of claim 1 wherein p is 3 and G is a hydrocarbon fragment obtained by removal of 3 hydroxyl groups from a trimethylolalkane.
12. The polysulfide silane composition of claim 1 wherein p is 4 and G is pentaerythrityl.
13. The polysulfide silane composition of claim 1 wherein p is 4 and G is a hydrocarbon fragment obtained by removal of 4 hydrogen atoms from 2-norbornylethane.
14. The polysulfide silane composition of claim 1 wherein p is greater than 4 and G is a hydrocarbon fragment obtained by removal of more then 4 hydrogen atoms from cyclododecane, triethylcyclohexane, 2,6-dimethyloctane, and squalane.
15. The polysulfide silane composition of claim 1 wherein G contains a tertiary amine functionality.
16. The polysulfide silane composition of claim 1 wherein G contains a cyano functionality .
17. A polysulfide silane composition comprising one or more isomers of tetrakis-1,3,4,5-(3-triethoxysilyl-1-propyltetrathio)neopentane.
18. A polysulfide silane composition comprising one or more isomers of tris-1,2,3-(3-triethoxysilyl-1-propyltetrathio)propane.
19. A process of making a hydrocarbon core polysulfide silane having the formula (X1X2X3Si-J-S x-)p-G
wherein p is 3 to 12, x is 2 to 20, X1 is a hydrolyzable functionality selected from the group consisting of -Cl, -Br, -OH, -O-N=C(R)2, -OR, or RC(=O)O-, in which R is a hydrocarbon fragment obtained by removing one hydrogen atom from a hydrocarbon having 1 to 20 carbon atoms, X2 and X3 are X1, R or H, J is a a hydrocarbon fragment obtained by removal of one hydrogen atom of R, and G is a hydrocarbon fragment obtained by removal of a p quantity of hydrogen atoms of a hydrocarbon having from 1 to 30 carbon atoms, comprising the steps of:
providing a mercaptan;
deprotonating the mercaptan;
providing a source of elemental sulfur;
forming a reactive sulfur anion by reacting the deprotonated mercaptan with the elemental sulfur; and coupling the reactive sulfur anion with a carbon containing substrate.
wherein p is 3 to 12, x is 2 to 20, X1 is a hydrolyzable functionality selected from the group consisting of -Cl, -Br, -OH, -O-N=C(R)2, -OR, or RC(=O)O-, in which R is a hydrocarbon fragment obtained by removing one hydrogen atom from a hydrocarbon having 1 to 20 carbon atoms, X2 and X3 are X1, R or H, J is a a hydrocarbon fragment obtained by removal of one hydrogen atom of R, and G is a hydrocarbon fragment obtained by removal of a p quantity of hydrogen atoms of a hydrocarbon having from 1 to 30 carbon atoms, comprising the steps of:
providing a mercaptan;
deprotonating the mercaptan;
providing a source of elemental sulfur;
forming a reactive sulfur anion by reacting the deprotonated mercaptan with the elemental sulfur; and coupling the reactive sulfur anion with a carbon containing substrate.
20. The process of claim 19 wherein the step of providing the mercaptan comprises providing a mercaptan having a formula X1X2X3Si-J-SH.
21. The process of claim 20 wherein the step of providing the mercaptan comprises providing a mercaptan selected from the group consisting of 3-mercapto-1-propyltriethoxysilane and 3-mercapto-1-propylmethyldiethoxysilane.
22. The process of claim 19 wherein the step of providing the mercaptan comprises providing a mercaptan having a formula (HS x-)p G.
23. The process of claim 22 wherein the step of providing the mercaptan comprises providing a mercaptan selected from the group consisting of 2,2-bis(mercaptomethyl)-1,3-dimercaptopropane and 1,2,3-trimercaptopropane.
24. The process of claim 19 wherein the step of deprotonating the mercaptan comprises deprotonating the mercaptan with a Brönsted base using p equivalents of the base for each mole of mercaptan.
25. The process of claim 19 wherein the step of deprotonating the mercaptan comprises deprotonating the mercaptan with an amine type base.
26. The process of claim 19 wherein the step of forming the reactive sulfur anion is sufficiently complete prior to introduction of the carbon containing substrate.
27. An elastomeric composition comprising at least one hydrocarbon core polysulfide silane having the formula (X1X2X3Si-J-S x-)p-G
wherein p is 3 to 12, x is 2 to 20, X1 is a hydrolyzable functionality selected from the group consisting of -Cl, -Br, -OH, -O-N=C(R)2, -OR, or RC(=O)O-, in which R is a hydrocarbon fragment obtained by removing one hydrogen atom from a hydrocarbon having 1 to 20 carbon atoms, X2 and X3 are X1, R or hydrogen, J is a hydrocarbon fragment obtained by removal of one hydrogen atom of R, and G is a hydrocarbon fragment obtained by removal of a p quantity of hydrogen atoms of a hydrocarbon having from 1 to 30 carbon atoms;
an unsaturated organic polymer; and a filler.
wherein p is 3 to 12, x is 2 to 20, X1 is a hydrolyzable functionality selected from the group consisting of -Cl, -Br, -OH, -O-N=C(R)2, -OR, or RC(=O)O-, in which R is a hydrocarbon fragment obtained by removing one hydrogen atom from a hydrocarbon having 1 to 20 carbon atoms, X2 and X3 are X1, R or hydrogen, J is a hydrocarbon fragment obtained by removal of one hydrogen atom of R, and G is a hydrocarbon fragment obtained by removal of a p quantity of hydrogen atoms of a hydrocarbon having from 1 to 30 carbon atoms;
an unsaturated organic polymer; and a filler.
28. The elastomeric composition of claim 27 wherein the at least one hydrocarbon core polysulfide silane is one or more isomers of tetrakis-1,3,4,5-(3-triethoxysilyl-1-propyltetrathio)neopentane.
29. The elastomeric composition of claim 27 wherein the at least one hydrocarbon core polysulfide silane is one or more isomers of -1,2,3-(3-triethoxysilyl-1-propyltetrathio)propane.
30. The elastomeric composition of claim 27 wherein the at least one hydrocarbon core polysulfide silane is present in an amount of about 0.05 to about 25 phr.
31. The elastomeric composition of claim 27 wherein the filler is present in an amount of about 1 to about 85 wt.% carbon black based on a total weight of the filler and the at least one hydrocarbon core polysulfide silane is present in an amount of about 0.1 to about 20 wt.% of the hydrocarbon core polysulfide silane based on a total weight of the filler.
32. A process of making a rubber composition comprising the steps of providing at least one isomer of a hydrocarbon core polysulfide silane having the formula (X1X2X3Si-J-S x-)p-G
wherein p is 3 to 12, x is 2 to 20, X1 is a hydrolyzable functionality selected from the group consisting of -Cl, -Br, -OH, -O-N=C(R)2, -OR, and RC(=O)O-, in which R is a hydrocarbon fragment obtained by removing one hydrogen atom from a hydrocarbon having 1 to 20 carbon atoms, X2 and X3 are X1, R or H, J is a hydrocarbon fragment obtained by removal of one hydrogen atom of R, and G is a hydrocarbon fragment obtained by removal of a p quantity of hydrogen atoms of a hydrocarbon having from 1 to 30 carbon atoms;
providing an organic polymer;
providing a filler;
thermomechanically mixing the organic polymer, filler and hydrocarbon core polysulfide silane to form a rubber mixture;
curing the rubber mixture to form a rubber composition having enhanced dispersion of the filler.
wherein p is 3 to 12, x is 2 to 20, X1 is a hydrolyzable functionality selected from the group consisting of -Cl, -Br, -OH, -O-N=C(R)2, -OR, and RC(=O)O-, in which R is a hydrocarbon fragment obtained by removing one hydrogen atom from a hydrocarbon having 1 to 20 carbon atoms, X2 and X3 are X1, R or H, J is a hydrocarbon fragment obtained by removal of one hydrogen atom of R, and G is a hydrocarbon fragment obtained by removal of a p quantity of hydrogen atoms of a hydrocarbon having from 1 to 30 carbon atoms;
providing an organic polymer;
providing a filler;
thermomechanically mixing the organic polymer, filler and hydrocarbon core polysulfide silane to form a rubber mixture;
curing the rubber mixture to form a rubber composition having enhanced dispersion of the filler.
33. The process of claim 32 wherein during the step of providing the filler, the filler has been pretreated with the hydrocarbon core polysulfide silane.
34. The process of claim 32 further including the step of adding curing agents to the rubber mixture in another thermomechanical mixing stage.
35. The process of claim 32 wherein the hydrocarbon core polysulfide silane is one or more isomers of tetrakis-1,3,4,5-(3-triethoxysilyl-1-propyltetrathio)neopentane.
36. The process of claim 32 wherein the hydrocarbon core polysulfide silane is one or more isomers of tris-1,2,3-(3-triethoxysilyl-1-propyltetrathio)propane.
37. A filler for dispersion in elastomeric compositions comprising:
mineral particulates; and at least one hydrocarbon core polysulfide silane having the formula:
(X1X2X3Si-J-S x-)p-G
wherein p is 3 to 12, x is 2 to 20, X1 is a hydrolyzable functionality selected from the group consisting of -Cl, -Br, -OH, -O-N=C(R)2, -OR, or RC(=O)O-, in which R is a hydrocarbon fragment obtained by removing one hydrogen atom from a hydrocarbon having 1 to 20 carbon atoms, X2 and X3 are X1, R or H, J is a hydrocarbon fragment obtained by removal of one hydrogen atom of R, and G is a hydrocarbon fragment obtained by removal of a p quantity of hydrogen atoms of a hydrocarbon having from 1 to 30 carbon atoms.
mineral particulates; and at least one hydrocarbon core polysulfide silane having the formula:
(X1X2X3Si-J-S x-)p-G
wherein p is 3 to 12, x is 2 to 20, X1 is a hydrolyzable functionality selected from the group consisting of -Cl, -Br, -OH, -O-N=C(R)2, -OR, or RC(=O)O-, in which R is a hydrocarbon fragment obtained by removing one hydrogen atom from a hydrocarbon having 1 to 20 carbon atoms, X2 and X3 are X1, R or H, J is a hydrocarbon fragment obtained by removal of one hydrogen atom of R, and G is a hydrocarbon fragment obtained by removal of a p quantity of hydrogen atoms of a hydrocarbon having from 1 to 30 carbon atoms.
38. The filler of claim 37 wherein the mineral particulates are siliceous particulates.
39. The filler of claim 37 further comprising carbon black.
40. The filler of claim 37 wherein the at least one hydrocarbon core polysulfide silane is one or more isomers of tetrakis-1,3,4,5-(3-triethoxysilyl-1-propyltetrathio)neopentane.
41. The filler of claim 37 wherein the at least one hydrocarbon core polysulfide silane is one or more isomers of tris-1,2,3-(3-triethoxysilyl-1-propyltetrathio)propane.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/657,934 | 2000-09-08 | ||
| US09/657,934 US6359046B1 (en) | 2000-09-08 | 2000-09-08 | Hydrocarbon core polysulfide silane coupling agents for filled elastomer compositions |
| PCT/US2001/028079 WO2002020534A1 (en) | 2000-09-08 | 2001-09-04 | Hydrocarbon core polysulfide silane coupling agents for filled elastomer compositions |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2419986A1 true CA2419986A1 (en) | 2002-03-14 |
| CA2419986C CA2419986C (en) | 2011-08-02 |
Family
ID=24639240
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2419986A Expired - Fee Related CA2419986C (en) | 2000-09-08 | 2001-09-04 | Hydrocarbon core polysulfide silane coupling agents for filled elastomer compositions |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US6359046B1 (en) |
| EP (1) | EP1315734B1 (en) |
| JP (1) | JP4200002B2 (en) |
| KR (1) | KR100850110B1 (en) |
| CN (1) | CN1222530C (en) |
| AT (1) | ATE270299T1 (en) |
| BR (1) | BR0113741A (en) |
| CA (1) | CA2419986C (en) |
| CZ (1) | CZ2003641A3 (en) |
| DE (1) | DE60104131T2 (en) |
| ES (1) | ES2223003T3 (en) |
| PL (1) | PL360997A1 (en) |
| PT (1) | PT1315734E (en) |
| TR (1) | TR200401890T4 (en) |
| WO (1) | WO2002020534A1 (en) |
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-
2000
- 2000-09-08 US US09/657,934 patent/US6359046B1/en not_active Expired - Lifetime
-
2001
- 2001-09-04 AT AT01966637T patent/ATE270299T1/en not_active IP Right Cessation
- 2001-09-04 CN CNB018153135A patent/CN1222530C/en not_active Expired - Fee Related
- 2001-09-04 CA CA2419986A patent/CA2419986C/en not_active Expired - Fee Related
- 2001-09-04 ES ES01966637T patent/ES2223003T3/en not_active Expired - Lifetime
- 2001-09-04 PT PT01966637T patent/PT1315734E/en unknown
- 2001-09-04 TR TR2004/01890T patent/TR200401890T4/en unknown
- 2001-09-04 BR BR0113741-7A patent/BR0113741A/en not_active IP Right Cessation
- 2001-09-04 CZ CZ2003641A patent/CZ2003641A3/en unknown
- 2001-09-04 PL PL36099701A patent/PL360997A1/en unknown
- 2001-09-04 JP JP2002525155A patent/JP4200002B2/en not_active Expired - Fee Related
- 2001-09-04 DE DE60104131T patent/DE60104131T2/en not_active Expired - Lifetime
- 2001-09-04 KR KR1020037003411A patent/KR100850110B1/en active IP Right Grant
- 2001-09-04 WO PCT/US2001/028079 patent/WO2002020534A1/en active IP Right Grant
- 2001-09-04 EP EP01966637A patent/EP1315734B1/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| CZ2003641A3 (en) | 2003-06-18 |
| EP1315734A1 (en) | 2003-06-04 |
| US6359046B1 (en) | 2002-03-19 |
| EP1315734B1 (en) | 2004-06-30 |
| PT1315734E (en) | 2004-09-30 |
| BR0113741A (en) | 2004-01-13 |
| TR200401890T4 (en) | 2004-09-21 |
| KR100850110B1 (en) | 2008-08-04 |
| CA2419986C (en) | 2011-08-02 |
| PL360997A1 (en) | 2004-09-20 |
| JP4200002B2 (en) | 2008-12-24 |
| CN1452625A (en) | 2003-10-29 |
| DE60104131T2 (en) | 2005-08-25 |
| WO2002020534A1 (en) | 2002-03-14 |
| ATE270299T1 (en) | 2004-07-15 |
| DE60104131D1 (en) | 2004-08-05 |
| KR20030029946A (en) | 2003-04-16 |
| CN1222530C (en) | 2005-10-12 |
| JP2004514657A (en) | 2004-05-20 |
| ES2223003T3 (en) | 2005-02-16 |
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| EEER | Examination request | ||
| MKLA | Lapsed |
Effective date: 20150904 |