CA1242846A - Process for the production of a cross-linked nitrile rubber - Google Patents

Process for the production of a cross-linked nitrile rubber

Info

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
Application number
CA000468288A
Other languages
French (fr)
Inventor
Joachim Thormer
Zsolt Szentivanyi
Hartmuth Buding
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bayer AG
Original Assignee
Bayer AG
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Bayer AG filed Critical Bayer AG
Application granted granted Critical
Publication of CA1242846A publication Critical patent/CA1242846A/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08KUse of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00Use of organic ingredients
    • C08K5/04Oxygen-containing compounds
    • C08K5/14Peroxides

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.

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

Claims (6)

THE EMBODIMENTS OF THE INVENTION IN WHICH AN EXCLUSIVE
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).
CA000468288A 1983-11-23 1984-11-21 Process for the production of a cross-linked nitrile rubber Expired CA1242846A (en)

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)

* Cited by examiner, † Cited by third party
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)

* Cited by examiner, † Cited by third party
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

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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