JPS624065B2 - - Google Patents
Info
- Publication number
- JPS624065B2 JPS624065B2 JP54049155A JP4915579A JPS624065B2 JP S624065 B2 JPS624065 B2 JP S624065B2 JP 54049155 A JP54049155 A JP 54049155A JP 4915579 A JP4915579 A JP 4915579A JP S624065 B2 JPS624065 B2 JP S624065B2
- Authority
- JP
- Japan
- Prior art keywords
- chloroprene
- polymer
- weight
- alkyl
- sulfur
- 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
- 229920000642 polymer Polymers 0.000 claims description 50
- YACLQRRMGMJLJV-UHFFFAOYSA-N chloroprene Chemical compound ClC(=C)C=C YACLQRRMGMJLJV-UHFFFAOYSA-N 0.000 claims description 36
- 239000000203 mixture Substances 0.000 claims description 21
- -1 vinyl dicarbonyl compound Chemical class 0.000 claims description 14
- 229920002554 vinyl polymer Polymers 0.000 claims description 11
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 7
- 229920001577 copolymer Polymers 0.000 claims description 7
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
- 229920001971 elastomer Polymers 0.000 claims description 6
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 5
- 239000000178 monomer Substances 0.000 claims description 5
- 239000004215 Carbon black (E152) Substances 0.000 claims description 4
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 4
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 229930195733 hydrocarbon Natural products 0.000 claims description 4
- 150000002430 hydrocarbons Chemical class 0.000 claims description 4
- 238000006116 polymerization reaction Methods 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 229920003244 diene elastomer Polymers 0.000 claims description 3
- 239000000806 elastomer Substances 0.000 claims description 3
- 229920001519 homopolymer Polymers 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229920001194 natural rubber Polymers 0.000 claims description 3
- 229920001084 poly(chloroprene) Polymers 0.000 claims description 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 3
- 101100294115 Caenorhabditis elegans nhr-4 gene Proteins 0.000 claims description 2
- 244000043261 Hevea brasiliensis Species 0.000 claims description 2
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 claims description 2
- 239000005062 Polybutadiene Substances 0.000 claims description 2
- 150000005690 diesters Chemical class 0.000 claims description 2
- 239000001530 fumaric acid Substances 0.000 claims description 2
- 229920003052 natural elastomer Polymers 0.000 claims description 2
- 229920002857 polybutadiene Polymers 0.000 claims description 2
- 229920002959 polymer blend Polymers 0.000 claims description 2
- 229920003048 styrene butadiene rubber Polymers 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N vinyl-ethylene Natural products C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- 238000009472 formulation Methods 0.000 description 8
- 238000000034 method Methods 0.000 description 7
- 239000003381 stabilizer Substances 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 5
- 238000004132 cross linking Methods 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000032683 aging Effects 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 235000011087 fumaric acid Nutrition 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 239000005060 rubber Substances 0.000 description 3
- 239000000523 sample Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- UWNADWZGEHDQAB-UHFFFAOYSA-N 2,5-dimethylhexane Chemical group CC(C)CCC(C)C UWNADWZGEHDQAB-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000013329 compounding Methods 0.000 description 2
- 238000006880 cross-coupling reaction Methods 0.000 description 2
- 150000002238 fumaric acids Chemical class 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 238000004898 kneading Methods 0.000 description 2
- 239000004816 latex Substances 0.000 description 2
- 229920000126 latex Polymers 0.000 description 2
- 150000002689 maleic acids Chemical class 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000004073 vulcanization Methods 0.000 description 2
- WYCXGQSQHAXLPK-VAWYXSNFSA-N (e)-1,4-diphenylbut-2-ene-1,4-dione Chemical group C=1C=CC=CC=1C(=O)\C=C\C(=O)C1=CC=CC=C1 WYCXGQSQHAXLPK-VAWYXSNFSA-N 0.000 description 1
- DFQUBYCHLQAFOW-NSCUHMNNSA-N (e)-4-(methylamino)-4-oxobut-2-enoic acid Chemical compound CNC(=O)\C=C\C(O)=O DFQUBYCHLQAFOW-NSCUHMNNSA-N 0.000 description 1
- PNNFEYPWPCDLOC-UPHRSURJSA-N (z)-2,3-dichlorobut-2-enedioic acid Chemical class OC(=O)C(\Cl)=C(\Cl)C(O)=O PNNFEYPWPCDLOC-UPHRSURJSA-N 0.000 description 1
- ICGVVJBVUNTWMA-UHFFFAOYSA-N 1,4-dinaphthalen-1-ylbut-2-ene-1,4-dione Chemical group C1=CC=C2C(C(C=CC(=O)C=3C4=CC=CC=C4C=CC=3)=O)=CC=CC2=C1 ICGVVJBVUNTWMA-UHFFFAOYSA-N 0.000 description 1
- BAWHYOHVWHQWFQ-UHFFFAOYSA-N 1-naphthalen-1-ylpyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1=CC=CC2=CC=CC=C12 BAWHYOHVWHQWFQ-UHFFFAOYSA-N 0.000 description 1
- HIDBROSJWZYGSZ-UHFFFAOYSA-N 1-phenylpyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1=CC=CC=C1 HIDBROSJWZYGSZ-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 102000035195 Peptidases Human genes 0.000 description 1
- 108091005804 Peptidases Proteins 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- ROPXFXOUUANXRR-BUHFOSPRSA-N bis(2-ethylhexyl) (e)-but-2-enedioate Chemical group CCCCC(CC)COC(=O)\C=C\C(=O)OCC(CC)CCCC ROPXFXOUUANXRR-BUHFOSPRSA-N 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 239000013068 control sample Substances 0.000 description 1
- CPZVJYPXOWWFSW-VAWYXSNFSA-N dibenzyl (e)-but-2-enedioate Chemical compound C=1C=CC=CC=1COC(=O)/C=C/C(=O)OCC1=CC=CC=C1 CPZVJYPXOWWFSW-VAWYXSNFSA-N 0.000 description 1
- JBSLOWBPDRZSMB-BQYQJAHWSA-N dibutyl (e)-but-2-enedioate Chemical compound CCCCOC(=O)\C=C\C(=O)OCCCC JBSLOWBPDRZSMB-BQYQJAHWSA-N 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- TVWTZAGVNBPXHU-FOCLMDBBSA-N dioctyl (e)-but-2-enedioate Chemical group CCCCCCCCOC(=O)\C=C\C(=O)OCCCCCCCC TVWTZAGVNBPXHU-FOCLMDBBSA-N 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- HQLVLAGOVHPVAC-WAYWQWQTSA-N ethyl (z)-4-(ethylamino)-4-oxobut-2-enoate Chemical compound CCNC(=O)\C=C/C(=O)OCC HQLVLAGOVHPVAC-WAYWQWQTSA-N 0.000 description 1
- RTCZYYVZCYMEHD-PLNGDYQASA-N ethyl (z)-4-(methylamino)-4-oxobut-2-enoate Chemical compound CCOC(=O)\C=C/C(=O)NC RTCZYYVZCYMEHD-PLNGDYQASA-N 0.000 description 1
- IMTDFNMATLDXLQ-WAYWQWQTSA-N ethyl (z)-4-oxo-4-(propylamino)but-2-enoate Chemical compound CCCNC(=O)\C=C/C(=O)OCC IMTDFNMATLDXLQ-WAYWQWQTSA-N 0.000 description 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- HFMPYWLGKKVUFE-WAYWQWQTSA-N methyl (z)-4-(butylamino)-4-oxobut-2-enoate Chemical compound CCCCNC(=O)\C=C/C(=O)OC HFMPYWLGKKVUFE-WAYWQWQTSA-N 0.000 description 1
- GYKIRBDPNRCHNO-PLNGDYQASA-N methyl (z)-4-(ethylamino)-4-oxobut-2-enoate Chemical compound CCNC(=O)\C=C/C(=O)OC GYKIRBDPNRCHNO-PLNGDYQASA-N 0.000 description 1
- AUUCQDFERUTDCX-HJWRWDBZSA-N methyl (z)-4-(heptylamino)-4-oxobut-2-enoate Chemical compound CCCCCCCNC(=O)\C=C/C(=O)OC AUUCQDFERUTDCX-HJWRWDBZSA-N 0.000 description 1
- WTRASWFVDDDXGT-FPLPWBNLSA-N methyl (z)-4-(hexylamino)-4-oxobut-2-enoate Chemical compound CCCCCCNC(=O)\C=C/C(=O)OC WTRASWFVDDDXGT-FPLPWBNLSA-N 0.000 description 1
- WNDNGQNMDQAVNG-ARJAWSKDSA-N methyl (z)-4-(methylamino)-4-oxobut-2-enoate Chemical compound CNC(=O)\C=C/C(=O)OC WNDNGQNMDQAVNG-ARJAWSKDSA-N 0.000 description 1
- YFYLRPBKNXFGQQ-KTKRTIGZSA-N methyl (z)-4-(octylamino)-4-oxobut-2-enoate Chemical compound CCCCCCCCNC(=O)\C=C/C(=O)OC YFYLRPBKNXFGQQ-KTKRTIGZSA-N 0.000 description 1
- UEMUVNUCRFEZHQ-SREVYHEPSA-N methyl (z)-4-oxo-4-(pentylamino)but-2-enoate Chemical compound CCCCCNC(=O)\C=C/C(=O)OC UEMUVNUCRFEZHQ-SREVYHEPSA-N 0.000 description 1
- OLVIWOSSWCLGRW-PLNGDYQASA-N methyl (z)-4-oxo-4-(propylamino)but-2-enoate Chemical compound CCCNC(=O)\C=C/C(=O)OC OLVIWOSSWCLGRW-PLNGDYQASA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920001195 polyisoprene Polymers 0.000 description 1
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 1
- 238000012802 pre-warming Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 235000019833 protease Nutrition 0.000 description 1
- 238000000518 rheometry Methods 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 238000010008 shearing Methods 0.000 description 1
- GGCZERPQGJTIQP-UHFFFAOYSA-M sodium 2-anthraquinonesulfonate Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)[O-])=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-M 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
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
- C08K5/16—Nitrogen-containing compounds
- C08K5/20—Carboxylic acid amides
-
- 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
-
- 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
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3412—Heterocyclic compounds having nitrogen in the ring having one nitrogen atom in the ring
- C08K5/3415—Five-membered rings
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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/899,296 US4154707A (en) | 1978-04-24 | 1978-04-24 | Process for elastomer viscosity stabilization |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS54141834A JPS54141834A (en) | 1979-11-05 |
| JPS624065B2 true JPS624065B2 (US08118993-20120221-C00002.png) | 1987-01-28 |
Family
ID=25410748
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP4915579A Granted JPS54141834A (en) | 1978-04-24 | 1979-04-23 | Stabilization of elastomer viscosity |
Country Status (6)
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0295156U (US08118993-20120221-C00002.png) * | 1989-01-13 | 1990-07-30 |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS59124950A (ja) * | 1982-12-29 | 1984-07-19 | Mitsubishi Petrochem Co Ltd | ポリフエニレンエ−テル樹脂組成物 |
| US4696754A (en) * | 1986-08-11 | 1987-09-29 | Morton Thiokol, Inc. | Lubricant-stabilizer compositions for halogen-containing organic polymers and polymer compositions thereof |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2313757A (en) * | 1940-09-19 | 1943-03-16 | Dow Chemical Co | Vinylidene chloride composition stable to light |
| US2392756A (en) * | 1942-05-20 | 1946-01-08 | Du Pont | Haloprene copolymer |
| US2885319A (en) * | 1953-12-17 | 1959-05-05 | Pittsburgh Coke And Chemical C | N-phenylmaleamic acid esters as fungicides |
| BE590586A (US08118993-20120221-C00002.png) * | 1959-05-07 | |||
| IT642042A (US08118993-20120221-C00002.png) * | 1960-12-21 | |||
| US3506624A (en) * | 1968-03-11 | 1970-04-14 | Rudolf Adolf Behrens | Elastomer compositions vulcanized with sulfur,a salt of an organic acid,and a maleimide compound |
-
1978
- 1978-04-24 US US05/899,296 patent/US4154707A/en not_active Expired - Lifetime
-
1979
- 1979-04-20 CA CA000326023A patent/CA1116779A/en not_active Expired
- 1979-04-21 DE DE2916267A patent/DE2916267C2/de not_active Expired
- 1979-04-23 FR FR7910182A patent/FR2424297A1/fr active Granted
- 1979-04-23 GB GB7914032A patent/GB2019414B/en not_active Expired
- 1979-04-23 JP JP4915579A patent/JPS54141834A/ja active Granted
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0295156U (US08118993-20120221-C00002.png) * | 1989-01-13 | 1990-07-30 |
Also Published As
| Publication number | Publication date |
|---|---|
| GB2019414A (en) | 1979-10-31 |
| FR2424297A1 (fr) | 1979-11-23 |
| FR2424297B1 (US08118993-20120221-C00002.png) | 1984-06-22 |
| GB2019414B (en) | 1982-09-29 |
| US4154707A (en) | 1979-05-15 |
| DE2916267C2 (de) | 1986-11-06 |
| DE2916267A1 (de) | 1979-10-31 |
| JPS54141834A (en) | 1979-11-05 |
| CA1116779A (en) | 1982-01-19 |
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