CA2404295A1 - Process for hydrogenating carboxylated nitrile rubber, the hydrogenated rubber and its uses - Google Patents
Process for hydrogenating carboxylated nitrile rubber, the hydrogenated rubber and its uses Download PDFInfo
- Publication number
- CA2404295A1 CA2404295A1 CA002404295A CA2404295A CA2404295A1 CA 2404295 A1 CA2404295 A1 CA 2404295A1 CA 002404295 A CA002404295 A CA 002404295A CA 2404295 A CA2404295 A CA 2404295A CA 2404295 A1 CA2404295 A1 CA 2404295A1
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- CA
- Canada
- Prior art keywords
- polymer
- process according
- weight
- rhodium
- hydrogenated
- 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
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08C—TREATMENT OR CHEMICAL MODIFICATION OF RUBBERS
- C08C19/00—Chemical modification of rubber
- C08C19/02—Hydrogenation
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L13/00—Compositions of rubbers containing carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L15/00—Compositions of rubber derivatives
- C08L15/005—Hydrogenated nitrile rubber
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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)
- General Chemical & Material Sciences (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
Polymers of a conjugated diene, an unsaturated nitrile and an .alpha., .beta .- unsaturated carboxylic acid are selectively hydrogenated to reduce carbon- carbon double bonds, without also reducing carboxyl groups and nitrile group s, using a rhodium-containing compound as catalyst. The hydrogenated polymers a re novel and display excellent adhesive properties at both room temperature and high temperature, excellent hot tear strength, and excellent abrasion resistance.
Claims (35)
1. A process for selectively hydrogenating a polymer of a conjugated diene, an unsaturated nitrite and an unsaturated carboxylic acid, which comprises subjecting the polymer to hydrogenation in the presence of a rhodium-containing compound as catalyst anal a co-catalyst ligand, wherein the weight ratio of the rhodium-containing compound to the co-catalyst ligand is from 1:3 to 1:55.
2. A process according to claim 1, wherein the rhodium-containing compound is a compound of the formula:
(R m B)1RhX n wherein each R is a C1-C6-alkyl group, a C4-C8 cycloalkyl group a C6-C15-aryl group or a C7-C15 aralkyl group, B is an atom of phosphorus, arsenic or sulphur, or is a sulphonyl group S=O, X
is hydrogen or an anion, 1 is 2, 3 or 4, m is 2 or 3 and n is 1, 2 or 3.
(R m B)1RhX n wherein each R is a C1-C6-alkyl group, a C4-C8 cycloalkyl group a C6-C15-aryl group or a C7-C15 aralkyl group, B is an atom of phosphorus, arsenic or sulphur, or is a sulphonyl group S=O, X
is hydrogen or an anion, 1 is 2, 3 or 4, m is 2 or 3 and n is 1, 2 or 3.
3. A process according to claim 2, wherein the co-catalyst ligand is of formula:
R m B
where R, m and B are as defined in claim 2.
R m B
where R, m and B are as defined in claim 2.
4. A process according to claim 2 or 3 wherein B is phosphorus.
5. A process according to any one of claims 1 to 4, wherein the rhodium-containing compound is tris-(triphenylphosphine)-rhodium(I)-chloride, tris-(triphenylphosphine)-rhodium(III)-chloride, tris-(dimethylsulphoxide)-rhodium(III)-chloride, or tetrakis-(triphenylphosphine)-rhodium hydride.
6. A process according to any one of claims 1 to 5, wherein the amount of the rhodium-containing compound is in the range 0.03 to 0.5%, based on the weight of the polymer to be hydrogenated.
7. A process according to claim 4, 5 or 6, wherein the co-catalyst ligand is triphenylphosphine.
8. A process according to claim 4, 5, 6 or 7, wherein the weight ratio of rhodium-containing compound to co-catalyst ligand is in the range 1:3 to 1:45.
9. A process according to any one of claims 4 to 7, wherein the amount of co-catalyst is in the range 0.1 to 33 parts by weight per hundred parts by weight of polymer.
10. A process according to claim 9 wherein the amount of co-catalyst is in the range 0.5 to 20 parts by weight per hundred parts by weight of polymer.
11. A process according to claim 9 wherein the amount of co-catalyst is in the range 1 to less than 5 parts by weight per hundred parts by weight of polymer.
12. A process according to claim 9, 10 or 11 wherein the amount of co-catalyst is greater than 2 parts by weight per hundred parts by weight of polymer.
13. A process according to any one of claims 1 to 12 wherein the polymer that is subjected to selective hydrogenation has a molecular weight greater than about 60,000.
14. A process according to any one of claims 1 to 12 wherein the polymer that is subjected to selective hydrogenation has a molecular weight greater than about 100,000.
15. A process according to any one of claims 1 to 14, which is carried out at a temperature in the range of 60°to 160°C and a pressure in the range 10 to 250 atmospheres.
16. A process according to any one of claims 1 to 15, wherein the selective hydrogenation is carried out until at least 80% of the carbon-carbon double bonds have been hydrogenated.
17. A process according to claim 16, wherein the selective hydrogenation is carried out until at least 90% of the carbon-carbon double bonds have been hydrogenated.
18. A process according to claims 16, wherein the selective hydrogenation is carried out until at least 95% of the carbon-carbon double bonds have been hydrogenated.
19. A process according to claim 16, wherein the selective hydrogenation is carried out until at least 99% of the carbon-carbon double bonds have been hydrogenated.
20. A process according to any one of claims 1 to 19, wherein the polymer comprises from 85 to 50% by weight of conjugated diene, from 0.1 to 10% by weight of .alpha., .beta.-unsaturated carboxylic acid and from 15 to 50% by weight of acrylonitrile or methacrylonitrile.
21. A statistical polymer of a conjugated diene, an unsaturated nitrile and an unsaturated carboxylic acid, wherein at least 80% of carbon-carbon double bonds in the polymer backbone have been selectively hydrogenated without concomitant hydrogenation of nitrile groups or carboxyl groups.
22. A polymer according to claim 21, wherein at least 95%
of carbon-carbon double bonds have been selectively hydrogenated.
of carbon-carbon double bonds have been selectively hydrogenated.
23. A polymer according to claim 21, wherein at least 99%
of carbon-carbon double bonds have been selectively hydrogenated.
of carbon-carbon double bonds have been selectively hydrogenated.
24. A polymer according to claim 21, 22 or 23 which has a molecular weight greater than 60,000.
25. A polymer according to claim 21, 22 or 223 which has a molecular weight greater than 100,000.
26. An artefact comprising a substrate and, adhering to the substrate, a polymer according to any one of claims 21 to 25.
27. An artefact according to claim 26 wherein the substrate is composed of a polyamide.
28. An artefact according to claim 27 wherein the polyamide is in the form of fiber and the polyamide fiber and adhering hydrogenated carboxylated nitrile rubber are in the form of a belt.
29. A polymer according to any one of claims 21 to 25, in the form of a seal.
30. A polymer according to any one of claims 21 to 25, in the form of a roll cover.
31. A polymer according to any one of claims 21 to 25 in the form of a pad for attachment to a track for a tracked vehicle.
32. A polymer according to any one of claims 21 to 25 in the form of an aqueous latex.
33. Use of a polymer according to any one of claims 21 to
34 25 in a polymer vulcanizate, a seal, a roll cover, a belt, a stator or a bearing pad for attachment to a track of a tracked vehicle.
35
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA2404295A CA2404295C (en) | 2000-04-10 | 2001-04-09 | Process for hydrogenating carboxylated nitrile rubber, the hydrogenated rubber and its uses |
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA002304501A CA2304501A1 (en) | 2000-04-10 | 2000-04-10 | Process for hydrogenating carboxylated nitrile rubber, the hydrogenated rubber and its uses |
| CA2,304,501 | 2000-04-10 | ||
| PCT/CA2001/000485 WO2001077185A1 (en) | 2000-04-10 | 2001-04-09 | Process for hydrogenating carboxylated nitrile rubber, the hydrogenated rubber and its uses |
| CA2404295A CA2404295C (en) | 2000-04-10 | 2001-04-09 | Process for hydrogenating carboxylated nitrile rubber, the hydrogenated rubber and its uses |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2404295A1 true CA2404295A1 (en) | 2001-10-18 |
| CA2404295C CA2404295C (en) | 2010-06-29 |
Family
ID=25681708
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2404295A Expired - Fee Related CA2404295C (en) | 2000-04-10 | 2001-04-09 | Process for hydrogenating carboxylated nitrile rubber, the hydrogenated rubber and its uses |
Country Status (1)
| Country | Link |
|---|---|
| CA (1) | CA2404295C (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2918612A1 (en) | 2014-03-10 | 2015-09-16 | LANXESS Deutschland GmbH | Hydrogenated nitrile rubber containing aminomethyl groups, method for producing the same, vulcanizable compositions containing hydrogenated nitrile rubber containing aminomethyl groups, method for their vulcanization and vulcanizates obtainable by this method |
| EP2918609A1 (en) | 2014-03-10 | 2015-09-16 | LANXESS Deutschland GmbH | Hydrogenated nitrile rubber containing amino methyl groups containing vulcanisable compositions , process for their vulcanization and vulcanisates obtainable by this process |
| EP2918608A1 (en) | 2014-03-10 | 2015-09-16 | LANXESS Deutschland GmbH | Hydrogenated nitrile rubber containing amino methyl group and method for producing the same |
-
2001
- 2001-04-09 CA CA2404295A patent/CA2404295C/en not_active Expired - Fee Related
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2918612A1 (en) | 2014-03-10 | 2015-09-16 | LANXESS Deutschland GmbH | Hydrogenated nitrile rubber containing aminomethyl groups, method for producing the same, vulcanizable compositions containing hydrogenated nitrile rubber containing aminomethyl groups, method for their vulcanization and vulcanizates obtainable by this method |
| EP2918609A1 (en) | 2014-03-10 | 2015-09-16 | LANXESS Deutschland GmbH | Hydrogenated nitrile rubber containing amino methyl groups containing vulcanisable compositions , process for their vulcanization and vulcanisates obtainable by this process |
| EP2918608A1 (en) | 2014-03-10 | 2015-09-16 | LANXESS Deutschland GmbH | Hydrogenated nitrile rubber containing amino methyl group and method for producing the same |
Also Published As
| Publication number | Publication date |
|---|---|
| CA2404295C (en) | 2010-06-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |
Effective date: 20160411 |