CA1242846A - Process for the production of a cross-linked nitrile rubber - Google Patents
Process for the production of a cross-linked nitrile rubberInfo
- Publication number
- CA1242846A CA1242846A CA000468288A CA468288A CA1242846A CA 1242846 A CA1242846 A CA 1242846A CA 000468288 A CA000468288 A CA 000468288A CA 468288 A CA468288 A CA 468288A CA 1242846 A CA1242846 A CA 1242846A
- Authority
- CA
- Canada
- Prior art keywords
- weight
- cross
- rubber
- production
- butylperoxi
- 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.)
- Expired
Links
Classifications
-
- 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
- C08K5/04—Oxygen-containing compounds
- C08K5/14—Peroxides
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
ABSTRACT
Process for the production of a cross-linked nitrile rubber"
Nitrile rubbers, from 85 to 96% of the double bonds of which are hydrogenated, may be cross-linked with peroxides to produce products which have outstanding ozone-resistance, if peroxides are used, the half-life of which is longer than 2 minutes in benzene at 170°C.
Process for the production of a cross-linked nitrile rubber"
Nitrile rubbers, from 85 to 96% of the double bonds of which are hydrogenated, may be cross-linked with peroxides to produce products which have outstanding ozone-resistance, if peroxides are used, the half-life of which is longer than 2 minutes in benzene at 170°C.
Description
, "Process for the production of a cross-linked nifrile rubber"
This invention relates to a process for the production of a cross-linked nitrile rubber, from 85 to S 96% of the double bonds of which are hydrogenated.
It is known from DE-OS 29 13 992 to vulcanise part;ally hydrogenated nitrile rubbers using a sulphur vulcanising system. Cross-linking with certain peroxides (Exarnple 4, No. 16) produces only unsatisfactory results.
Appropriate choice of peroxide has been found not only to avoid these poor results, but even to produce better results, partlcularly with regard to ozone-resistance, than when sulphur vulcanisation is used.
Thus, an object of the present invention is to provide a process for the production of cross-linked nitrile rubbers, from 85 to 98%, preferably from 90 to 95%, of the double bonds of which are hydrogenated, using from I to 10%, by weight, preferably from 4 to 7%, by weight, of peroxides, based on the quantity of polymer in the mixture, characterised in that peroxides are used, the half-life of which is longer thun 2 minutes in benzene at 170C and is longer than 8 mintues in LDPE (low-density polyethylene)at the same temperature.
Suitable nitrile rubbers consist of from 10 to 50%, by weight, of acrylonitrile units and from 90 to 50%, by weight, of conjugated diene units, such as butadiene, isoprene or l,3-pentadiene. The partial hydrogenation of nitrile rubbers is known.
The following are examples of suitable peroxides:
bis-t_butylperoxiisopropyl)-benzene; 2,5-dim~thyl-2,5-di (t-butylperoxi)-hexane-a~d ~,~-dîmelhyl-2,5-di(t-butylperoxi)-hexene-(3).
The term "half-life" means that, at a given temper-ature and after one half-life 50% of the quantity of peroxide which was present at the beginning of the half-8~
life has decomposed.
The rubber mixture nay contain other constituentswhich are conventionally used in the peroxlde cross-linking of polymers, such as fillers, plasticisers, anti-agents, processing auxiliaries, pigments, co-activators, such as triallyl isocyanurate, and acid acceptors.
The products which may be obtained according to the present invention have rnany uses: they may be used, for example, for sealings of all types, tubes, in particular hydraulic pipes, toothed belts, cable coverings, profiles, linings, rollers, membranes and rubber/metal parts.
Example Rubber compositions having the compositions given in the following Table are vulcanised at 1~C for 18 minutes.
A nitrile rubber consisting of 39%, by weight, of acrylonitrile and 61%, by weight, of butadiene and having a degree of hydrogenation of 90% is used.
The ozone-resistance of the vulcanisates is determined at various elongations according to DIN 53 509 (23C, 60% rel. air humidity, 250 pphm of ozone in air.) Peroxide cross-linking is found to result in better products with regard to the ozone-resistance thereof, than sulphur cross-linking.
- 3 8~i Table Parts, by weight Rubber 100 100 5tea~ic acid Wax (Lunacera C44) 2 ZnO active 3 5 MgO 7 7 Styrenised diphenylamine 1,1 2 Zinc salt of 2-nercaptobenzimidazole 0,4 3 Carbon black (Corax N 550) 50 50 Processing auxiliary - 2 Sulphur -0,125 Tetramethyl thiuram disulphide - 2 Sulphur donors TrialIylisocyanurate 1,75 Bis-(t-butylperoxiisopropyl-benzene) 7,5 Results (in hours) of 020ne ageing until the first sign of a crack Elongation 10% ~168 168 20% ~168 6 30% ~168 4 60% 24 4
This invention relates to a process for the production of a cross-linked nitrile rubber, from 85 to S 96% of the double bonds of which are hydrogenated.
It is known from DE-OS 29 13 992 to vulcanise part;ally hydrogenated nitrile rubbers using a sulphur vulcanising system. Cross-linking with certain peroxides (Exarnple 4, No. 16) produces only unsatisfactory results.
Appropriate choice of peroxide has been found not only to avoid these poor results, but even to produce better results, partlcularly with regard to ozone-resistance, than when sulphur vulcanisation is used.
Thus, an object of the present invention is to provide a process for the production of cross-linked nitrile rubbers, from 85 to 98%, preferably from 90 to 95%, of the double bonds of which are hydrogenated, using from I to 10%, by weight, preferably from 4 to 7%, by weight, of peroxides, based on the quantity of polymer in the mixture, characterised in that peroxides are used, the half-life of which is longer thun 2 minutes in benzene at 170C and is longer than 8 mintues in LDPE (low-density polyethylene)at the same temperature.
Suitable nitrile rubbers consist of from 10 to 50%, by weight, of acrylonitrile units and from 90 to 50%, by weight, of conjugated diene units, such as butadiene, isoprene or l,3-pentadiene. The partial hydrogenation of nitrile rubbers is known.
The following are examples of suitable peroxides:
bis-t_butylperoxiisopropyl)-benzene; 2,5-dim~thyl-2,5-di (t-butylperoxi)-hexane-a~d ~,~-dîmelhyl-2,5-di(t-butylperoxi)-hexene-(3).
The term "half-life" means that, at a given temper-ature and after one half-life 50% of the quantity of peroxide which was present at the beginning of the half-8~
life has decomposed.
The rubber mixture nay contain other constituentswhich are conventionally used in the peroxlde cross-linking of polymers, such as fillers, plasticisers, anti-agents, processing auxiliaries, pigments, co-activators, such as triallyl isocyanurate, and acid acceptors.
The products which may be obtained according to the present invention have rnany uses: they may be used, for example, for sealings of all types, tubes, in particular hydraulic pipes, toothed belts, cable coverings, profiles, linings, rollers, membranes and rubber/metal parts.
Example Rubber compositions having the compositions given in the following Table are vulcanised at 1~C for 18 minutes.
A nitrile rubber consisting of 39%, by weight, of acrylonitrile and 61%, by weight, of butadiene and having a degree of hydrogenation of 90% is used.
The ozone-resistance of the vulcanisates is determined at various elongations according to DIN 53 509 (23C, 60% rel. air humidity, 250 pphm of ozone in air.) Peroxide cross-linking is found to result in better products with regard to the ozone-resistance thereof, than sulphur cross-linking.
- 3 8~i Table Parts, by weight Rubber 100 100 5tea~ic acid Wax (Lunacera C44) 2 ZnO active 3 5 MgO 7 7 Styrenised diphenylamine 1,1 2 Zinc salt of 2-nercaptobenzimidazole 0,4 3 Carbon black (Corax N 550) 50 50 Processing auxiliary - 2 Sulphur -0,125 Tetramethyl thiuram disulphide - 2 Sulphur donors TrialIylisocyanurate 1,75 Bis-(t-butylperoxiisopropyl-benzene) 7,5 Results (in hours) of 020ne ageing until the first sign of a crack Elongation 10% ~168 168 20% ~168 6 30% ~168 4 60% 24 4
Claims (6)
PROPERTY OR PRIVILEGE IS CLAIMED ARE DEFINED AS FOLLOWS:
1. A process for the production of a cross-linked nitrile rubber, from 85 to 96% of the double bonds of which are hydrogenated, which comprises using as the cross-linking agent from 1 to 10%, by weight, based on the rubber, of a peroxide having a half-life at 170°C of more than 2 minutes in benzene and more than 8 minutes in low density polyethylene at the same temperature.
2. A process as claimed in claim 1 wherein the nitrile rub-ber is from 90 to 95% hydrogenated.
3. A process as claimed in claim 1 wherein from 4 to 7%, by weight, of peroxide is used.
4. A process as claimed in claim 1, 2 or 3 wherein the rubber comprises from 10 to 50%, by weight, of acrylonitrile units and from 90% to 50%, by weight, of conjugated diene units.
5. A process as claimed in claim 1, 2 or 3 wherein the pe-roxide is selected from the following: bis-t-butylperoxiisopropyl)-benzene; 2,5-dimethyl-2,5-di(t-butylperoxi)-hexane and 2,5-dimethyl-2,5-di(t-butylperoxi)-hexene-(3).
6. A process as claimed in claim 1, 2 or 3 wherein the rubber comprises from 10 to 50%, by weight, of acrylonitrile units and from 90% to 50%, by weight, of conjugated diene units and the peroxide is selected from the following: bis-t-butylperoxiisopropyl)-benzene;
2,5-dimethyl-2,5-di(t-butylperoxi)-hexane and 2,5-dimethyl-2,5-di (t-butylperoxi)-hexene-(3).
2,5-dimethyl-2,5-di(t-butylperoxi)-hexane and 2,5-dimethyl-2,5-di (t-butylperoxi)-hexene-(3).
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEP3342309.1 | 1983-11-23 | ||
DE19833342309 DE3342309A1 (en) | 1983-11-23 | 1983-11-23 | METHOD FOR PRODUCING A NETWORKED NITRILE RUBBER |
Publications (1)
Publication Number | Publication Date |
---|---|
CA1242846A true CA1242846A (en) | 1988-10-04 |
Family
ID=6215035
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CA000468288A Expired CA1242846A (en) | 1983-11-23 | 1984-11-21 | Process for the production of a cross-linked nitrile rubber |
Country Status (4)
Country | Link |
---|---|
EP (1) | EP0144805B1 (en) |
JP (1) | JPS60124638A (en) |
CA (1) | CA1242846A (en) |
DE (2) | DE3342309A1 (en) |
Families Citing this family (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS6086135A (en) * | 1983-10-19 | 1985-05-15 | Nippon Zeon Co Ltd | Rubber composition having improved steam resistance |
US4983685A (en) * | 1986-06-10 | 1991-01-08 | Sumitomo Chemical Company, Limited | Methods for production of crosslinked rubber products |
JPH07103266B2 (en) * | 1987-01-14 | 1995-11-08 | 日本ゼオン株式会社 | Rubber composition |
JPS6487937A (en) * | 1987-09-30 | 1989-04-03 | Bando Chemical Ind | Belt with heat resistant teeth |
JPH0710928B2 (en) * | 1988-11-14 | 1995-02-08 | 横浜ゴム株式会社 | Rubber composition and fiber composite and hose |
JP2602029Y2 (en) * | 1991-11-11 | 1999-12-20 | 王 水木 | Bra with adjustable size |
GB0011479D0 (en) * | 2000-05-13 | 2000-06-28 | Wharton Graham J | A hydraulic brake seal |
EP2918608A1 (en) | 2014-03-10 | 2015-09-16 | LANXESS Deutschland GmbH | Hydrogenated nitrile rubber containing amino methyl group and method for producing the same |
EP2918612B1 (en) | 2014-03-10 | 2016-09-07 | ARLANXEO 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 |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
NL272390A (en) * | 1960-12-22 | |||
AU472354B2 (en) * | 1973-06-26 | 1976-05-20 | Phillips Petroleum Company | Rotational molding and composition therefor |
JPS5133141A (en) * | 1974-09-14 | 1976-03-22 | Bridgestone Tire Co Ltd | KODANSEIRITSU GOMUSOSEIBUTSU |
JPS55130746A (en) * | 1979-04-02 | 1980-10-09 | Mitsubishi Petrochem Co Ltd | Preparation of hardener-containing granulated olefin copolymer rubber |
JPS58167604A (en) * | 1982-03-27 | 1983-10-03 | Nippon Zeon Co Ltd | Rubber member having resistance to oil deterioration |
DE3226081C1 (en) * | 1982-07-13 | 1983-12-15 | Bayer Ag, 5090 Leverkusen | Use of hydrogenated butadiene-acrylonitrile copolymers for the production of molded articles |
-
1983
- 1983-11-23 DE DE19833342309 patent/DE3342309A1/en not_active Withdrawn
-
1984
- 1984-11-12 EP EP84113613A patent/EP0144805B1/en not_active Expired
- 1984-11-12 DE DE8484113613T patent/DE3462402D1/en not_active Expired
- 1984-11-19 JP JP59242547A patent/JPS60124638A/en active Pending
- 1984-11-21 CA CA000468288A patent/CA1242846A/en not_active Expired
Also Published As
Publication number | Publication date |
---|---|
EP0144805A3 (en) | 1985-07-31 |
DE3342309A1 (en) | 1985-05-30 |
EP0144805A2 (en) | 1985-06-19 |
EP0144805B1 (en) | 1987-02-25 |
JPS60124638A (en) | 1985-07-03 |
DE3462402D1 (en) | 1987-04-02 |
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Legal Events
Date | Code | Title | Description |
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MKEX | Expiry |