CA1094742A - Methode de production de caoutchouc acrylique propre a la vulcanisation - Google Patents

Methode de production de caoutchouc acrylique propre a la vulcanisation

Info

Publication number: CA1094742A
Authority: CA; Canada
Prior art keywords: malonic acid; acid derivative; process according; parts; acrylic rubber
Prior art date: 1976-05-01
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

CA277,275A

Other languages

English (en)

Inventor

Michinori Kuraya

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.)

Toyo Seal Industries Co Ltd

Original Assignee

Toyo Seal Industries Co Ltd

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.)

1976-05-01

Filing date

1977-04-26

Publication date

1981-01-27

1976-05-01 Priority claimed from JP5021276A external-priority patent/JPS52133395A/ja

1976-12-28 Priority claimed from JP16001076A external-priority patent/JPS5382891A/ja

1977-04-26 Application filed by Toyo Seal Industries Co Ltd filed Critical Toyo Seal Industries Co Ltd

1981-01-27 Application granted granted Critical

1981-01-27 Publication of CA1094742A publication Critical patent/CA1094742A/fr

Status Expired legal-status Critical Current

Links

229920000800 acrylic rubber Polymers 0.000 title claims abstract description 45
229920000058 polyacrylate Polymers 0.000 title claims abstract description 45
238000000034 method Methods 0.000 title claims abstract description 17
-1 acrylic ester Chemical class 0.000 claims abstract description 19
150000002690 malonic acid derivatives Chemical class 0.000 claims abstract description 16
239000003795 chemical substances by application Substances 0.000 claims abstract description 9
KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical class CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 claims abstract description 8
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims abstract description 7
238000007334 copolymerization reaction Methods 0.000 claims abstract description 6
AUZONCFQVSMFAP-UHFFFAOYSA-N disulfiram Chemical compound CCN(CC)C(=S)SSC(=S)N(CC)CC AUZONCFQVSMFAP-UHFFFAOYSA-N 0.000 claims description 12
JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 claims description 8
PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 claims description 8
WXKCRCGKCOKJEF-UHFFFAOYSA-N prop-2-enyl 2-cyanoacetate Chemical group C=CCOC(=O)CC#N WXKCRCGKCOKJEF-UHFFFAOYSA-N 0.000 claims description 6
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 4
BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims description 4
229960002447 thiram Drugs 0.000 claims description 4
CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 claims description 3
125000004093 cyano group Chemical group *C#N 0.000 claims description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
125000005394 methallyl group Chemical group 0.000 claims description 3
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 3
229920002554 vinyl polymer Polymers 0.000 claims description 3
239000003054 catalyst Substances 0.000 claims description 2
229920001577 copolymer Polymers 0.000 claims description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
239000012736 aqueous medium Substances 0.000 claims 1
ANTNQGGUTAZUIC-UHFFFAOYSA-N ethenyl 2-cyanoacetate Chemical group C=COC(=O)CC#N ANTNQGGUTAZUIC-UHFFFAOYSA-N 0.000 claims 1
230000000704 physical effect Effects 0.000 abstract description 6
150000002148 esters Chemical class 0.000 abstract description 5
239000000203 mixture Substances 0.000 description 10
238000006243 chemical reaction Methods 0.000 description 8
XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
235000021355 Stearic acid Nutrition 0.000 description 5
MLIREBYILWEBDM-UHFFFAOYSA-N cyanoacetic acid Chemical compound OC(=O)CC#N MLIREBYILWEBDM-UHFFFAOYSA-N 0.000 description 5
AFZSMODLJJCVPP-UHFFFAOYSA-N dibenzothiazol-2-yl disulfide Chemical compound C1=CC=C2SC(SSC=3SC4=CC=CC=C4N=3)=NC2=C1 AFZSMODLJJCVPP-UHFFFAOYSA-N 0.000 description 5
238000002156 mixing Methods 0.000 description 5
239000000178 monomer Substances 0.000 description 5
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 5
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 5
239000008117 stearic acid Substances 0.000 description 5
238000004073 vulcanization Methods 0.000 description 5
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
229910052799 carbon Inorganic materials 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 3
239000002253 acid Substances 0.000 description 3
NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
238000004132 cross linking Methods 0.000 description 3
230000000694 effects Effects 0.000 description 3
229920001971 elastomer Polymers 0.000 description 3
ZIUSEGSNTOUIPT-UHFFFAOYSA-N ethyl 2-cyanoacetate Chemical compound CCOC(=O)CC#N ZIUSEGSNTOUIPT-UHFFFAOYSA-N 0.000 description 3
238000004898 kneading Methods 0.000 description 3
239000005060 rubber Substances 0.000 description 3
NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
ACIAHEMYLLBZOI-ZZXKWVIFSA-N Unsaturated alcohol Chemical compound CC\C(CO)=C/C ACIAHEMYLLBZOI-ZZXKWVIFSA-N 0.000 description 2
150000001412 amines Chemical class 0.000 description 2
238000007664 blowing Methods 0.000 description 2
231100000078 corrosiveness Toxicity 0.000 description 2
238000007720 emulsion polymerization reaction Methods 0.000 description 2
229920000259 polyoxyethylene lauryl ether Polymers 0.000 description 2
USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 2
239000012744 reinforcing agent Substances 0.000 description 2
235000019333 sodium laurylsulphate Nutrition 0.000 description 2
238000003756 stirring Methods 0.000 description 2
238000003860 storage Methods 0.000 description 2
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 description 1
STMDPCBYJCIZOD-UHFFFAOYSA-N 2-(2,4-dinitroanilino)-4-methylpentanoic acid Chemical compound CC(C)CC(C(O)=O)NC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O STMDPCBYJCIZOD-UHFFFAOYSA-N 0.000 description 1
MLIREBYILWEBDM-UHFFFAOYSA-M 2-cyanoacetate Chemical compound [O-]C(=O)CC#N MLIREBYILWEBDM-UHFFFAOYSA-M 0.000 description 1
OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 1
BUZICZZQJDLXJN-UHFFFAOYSA-N 3-azaniumyl-4-hydroxybutanoate Chemical compound OCC(N)CC(O)=O BUZICZZQJDLXJN-UHFFFAOYSA-N 0.000 description 1
ICBZSKCTKKUQSY-YUWZRIFDSA-N 4-[(1r,2s)-1-hydroxy-2-(methylamino)propyl]phenol;hydrochloride Chemical compound Cl.CN[C@@H](C)[C@H](O)C1=CC=C(O)C=C1 ICBZSKCTKKUQSY-YUWZRIFDSA-N 0.000 description 1
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
239000006229 carbon black Substances 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
238000005336 cracking Methods 0.000 description 1
229910001873 dinitrogen Inorganic materials 0.000 description 1
238000004821 distillation Methods 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
125000003700 epoxy group Chemical group 0.000 description 1
230000032050 esterification Effects 0.000 description 1
238000005886 esterification reaction Methods 0.000 description 1
235000019441 ethanol Nutrition 0.000 description 1
XJELOQYISYPGDX-UHFFFAOYSA-N ethenyl 2-chloroacetate Chemical compound ClCC(=O)OC=C XJELOQYISYPGDX-UHFFFAOYSA-N 0.000 description 1
UKFXDFUAPNAMPJ-UHFFFAOYSA-N ethylmalonic acid Chemical compound CCC(C(O)=O)C(O)=O UKFXDFUAPNAMPJ-UHFFFAOYSA-N 0.000 description 1
238000001125 extrusion Methods 0.000 description 1
239000007789 gas Substances 0.000 description 1
VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
239000007788 liquid Substances 0.000 description 1
150000002691 malonic acids Chemical class 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 1
RPQRDASANLAFCM-UHFFFAOYSA-N oxiran-2-ylmethyl prop-2-enoate Chemical compound C=CC(=O)OCC1CO1 RPQRDASANLAFCM-UHFFFAOYSA-N 0.000 description 1
229920000768 polyamine Polymers 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
239000003505 polymerization initiator Substances 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000010992 reflux Methods 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
239000000344 soap Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
239000002904 solvent Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/12—Esters of monohydric alcohols or phenols

Landscapes

Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Organic Chemistry (AREA)
Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Compositions Of Macromolecular Compounds (AREA)
Sealing Material Composition (AREA)

CA277,275A 1976-05-01 1977-04-26 Methode de production de caoutchouc acrylique propre a la vulcanisation Expired CA1094742A (fr)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
JPSHO51-50212		1976-05-01
JP5021276A JPS52133395A (en)	1976-05-01	1976-05-01	Process for producing vulcanizable acrylic rubber
JPSHO51-160010		1976-12-28
JP16001076A JPS5382891A (en)	1976-12-28	1976-12-28	Process for producing vulcanizable acryl rubber

Publications (1)

Publication Number	Publication Date
CA1094742A true CA1094742A (fr)	1981-01-27

Family

ID=26390663

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA277,275A Expired CA1094742A (fr)	1976-05-01	1977-04-26	Methode de production de caoutchouc acrylique propre a la vulcanisation

Country Status (5)

Country	Link
CA (1)	CA1094742A (fr)
DE (1)	DE2719560C3 (fr)
FR (1)	FR2349606A1 (fr)
GB (1)	GB1579629A (fr)
IT (1)	IT1086798B (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US9540535B2 (en)	2010-09-29	2017-01-10	Jsr Corporation	Composition for forming liquid immersion upper layer film, and polymer

1977
- 1977-04-26 GB GB1741777A patent/GB1579629A/en not_active Expired
- 1977-04-26 CA CA277,275A patent/CA1094742A/fr not_active Expired
- 1977-04-28 IT IT4917977A patent/IT1086798B/it active
- 1977-04-29 FR FR7712947A patent/FR2349606A1/fr active Granted
- 1977-05-02 DE DE19772719560 patent/DE2719560C3/de not_active Expired

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US9540535B2 (en)	2010-09-29	2017-01-10	Jsr Corporation	Composition for forming liquid immersion upper layer film, and polymer
US9926462B2 (en)	2010-09-29	2018-03-27	Jsr Corporation	Composition for forming liquid immersion upper layer film, and polymer

Also Published As

Publication number	Publication date
FR2349606B1 (fr)	1979-03-30
DE2719560A1 (de)	1977-11-10
DE2719560B2 (de)	1979-12-06
FR2349606A1 (fr)	1977-11-25
IT1086798B (it)	1985-05-31
GB1579629A (en)	1980-11-19
DE2719560C3 (de)	1980-08-14

Legal Events

Date	Code	Title	Description
1998-01-27	MKEX	Expiry

Publication	Publication Date	Title
US4154914A (en)	1979-05-15	Process for producing acrylic rubber by copolymerizing acrylic ester and malonic acid derivative having active methylene group
US3326868A (en)	1967-06-20	Self-curing, oil-resistant copolymers containing alkoxyalkyl acrylates and n-alkoxyalkyl acrylamides
JPH01135811A (ja)	1989-05-29	アクリル系共重合体エラストマーの製造方法
CA1094742A (fr)	1981-01-27	Methode de production de caoutchouc acrylique propre a la vulcanisation
US4228265A (en)	1980-10-14	Process for producing sulfur-curable acrylic rubbers
JPH09143229A (ja)	1997-06-03	アクリル系共重合体エラストマーの製造法
US3450681A (en)	1969-06-17	Curable acrylate interpolymers containing alkoxyethyl or alkylthioethyl acrylates
US5219967A (en)	1993-06-15	Acrylic copolymer rubber
US4975508A (en)	1990-12-04	Acrylic copolymer elastomers
US5334683A (en)	1994-08-02	Acrylate polymer elastomer and vulcanizable composition containing the same
USRE31322E (en)	1983-07-26	Process for producing sulfur-curable acrylic rubbers
JP3496237B2 (ja)	2004-02-09	アクリル系共重合体およびその製造法
US4028316A (en)	1977-06-07	Vulcanized acrylate-ethylidene norbornene polymers
JPH06145257A (ja)	1994-05-24	アクリル系共重合ゴムの製造法およびその組成物
JP3156438B2 (ja)	2001-04-16	アクリル系共重合体
JPS59136303A (ja)	1984-08-04	加硫可能なアクリルゴムの製造法
JPS59113010A (ja)	1984-06-29	アクリルゴム及びその製造方法
JP2658184B2 (ja)	1997-09-30	アクリル系共重合体エラストマーの製造方法
JPH01132611A (ja)	1989-05-25	アクリル系共重合体エラストマーの製造方法
JP3528397B2 (ja)	2004-05-17	アクリル系共重合体エラストマーおよびその製造法
JP3601105B2 (ja)	2004-12-15	アクリルエラストマーおよびその製造法
JPH0714986B2 (ja)	1995-02-22	アクリルエラストマ−の製造法
JPH0237945B2 (fr)	1990-08-28
JP3387547B2 (ja)	2003-03-17	アクリレート系重合体エラストマーおよびその加硫性組成物
JPH01118412A (ja)	1989-05-10	エチレン−アクリレートエラストマーの加硫方法