JPH0469162B2 - - Google Patents
Info
- Publication number
- JPH0469162B2 JPH0469162B2 JP9838983A JP9838983A JPH0469162B2 JP H0469162 B2 JPH0469162 B2 JP H0469162B2 JP 9838983 A JP9838983 A JP 9838983A JP 9838983 A JP9838983 A JP 9838983A JP H0469162 B2 JPH0469162 B2 JP H0469162B2
- Authority
- JP
- Japan
- Prior art keywords
- rubber
- formula
- samples
- methyl alcohol
- oxomalonate
- 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
- 229920001971 elastomer Polymers 0.000 claims description 64
- 239000005060 rubber Substances 0.000 claims description 64
- 125000004185 ester group Chemical group 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 8
- 239000002841 Lewis acid Substances 0.000 claims description 6
- 150000007517 lewis acids Chemical class 0.000 claims description 6
- 150000002894 organic compounds Chemical class 0.000 claims description 5
- 150000002430 hydrocarbons Chemical group 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
- 229920001577 copolymer Polymers 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 8
- 229920001195 polyisoprene Polymers 0.000 description 7
- 239000000203 mixture Substances 0.000 description 6
- 238000010521 absorption reaction Methods 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 150000001993 dienes Chemical class 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 4
- 230000003712 anti-aging effect Effects 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 238000001879 gelation Methods 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 239000012299 nitrogen atmosphere Substances 0.000 description 4
- 230000000704 physical effect Effects 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 229910052717 sulfur Inorganic materials 0.000 description 4
- 239000011593 sulfur Substances 0.000 description 4
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000007259 addition reaction Methods 0.000 description 3
- XMPZTFVPEKAKFH-UHFFFAOYSA-P ceric ammonium nitrate Chemical compound [NH4+].[NH4+].[Ce+4].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O XMPZTFVPEKAKFH-UHFFFAOYSA-P 0.000 description 3
- DBKKFIIYQGGHJO-UHFFFAOYSA-N diethyl 2-oxopropanedioate Chemical compound CCOC(=O)C(=O)C(=O)OCC DBKKFIIYQGGHJO-UHFFFAOYSA-N 0.000 description 3
- 150000003613 toluenes Chemical class 0.000 description 3
- 238000004073 vulcanization Methods 0.000 description 3
- SDJHPPZKZZWAKF-UHFFFAOYSA-N 2,3-dimethylbuta-1,3-diene Chemical compound CC(=C)C(C)=C SDJHPPZKZZWAKF-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 125000002723 alicyclic group Chemical group 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 238000013329 compounding Methods 0.000 description 2
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 2
- LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 description 2
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000002715 modification method Methods 0.000 description 2
- XEEVLJKYYUVTRC-UHFFFAOYSA-L oxomalonate(2-) Chemical class [O-]C(=O)C(=O)C([O-])=O XEEVLJKYYUVTRC-UHFFFAOYSA-L 0.000 description 2
- 229920002857 polybutadiene Polymers 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 238000009864 tensile test Methods 0.000 description 2
- OJOWICOBYCXEKR-KRXBUXKQSA-N (5e)-5-ethylidenebicyclo[2.2.1]hept-2-ene Chemical compound C1C2C(=C/C)/CC1C=C2 OJOWICOBYCXEKR-KRXBUXKQSA-N 0.000 description 1
- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical group C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 description 1
- LOVYCUYJRWLTSU-UHFFFAOYSA-N 2-(3,4-dichlorophenoxy)-n,n-diethylethanamine Chemical compound CCN(CC)CCOC1=CC=C(Cl)C(Cl)=C1 LOVYCUYJRWLTSU-UHFFFAOYSA-N 0.000 description 1
- FEXBEKLLSUWSIM-UHFFFAOYSA-N 2-Butyl-4-methylphenol Chemical group CCCCC1=CC(C)=CC=C1O FEXBEKLLSUWSIM-UHFFFAOYSA-N 0.000 description 1
- MHKLKWCYGIBEQF-UHFFFAOYSA-N 4-(1,3-benzothiazol-2-ylsulfanyl)morpholine Chemical compound C1COCCN1SC1=NC2=CC=CC=C2S1 MHKLKWCYGIBEQF-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 244000043261 Hevea brasiliensis Species 0.000 description 1
- OUBMGJOQLXMSNT-UHFFFAOYSA-N N-isopropyl-N'-phenyl-p-phenylenediamine Chemical compound C1=CC(NC(C)C)=CC=C1NC1=CC=CC=C1 OUBMGJOQLXMSNT-UHFFFAOYSA-N 0.000 description 1
- 229920000459 Nitrile rubber Polymers 0.000 description 1
- 241001495453 Parthenium argentatum Species 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 229920005603 alternating copolymer Polymers 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000010692 aromatic oil Substances 0.000 description 1
- VLLYOYVKQDKAHN-UHFFFAOYSA-N buta-1,3-diene;2-methylbuta-1,3-diene Chemical compound C=CC=C.CC(=C)C=C VLLYOYVKQDKAHN-UHFFFAOYSA-N 0.000 description 1
- NTXGQCSETZTARF-UHFFFAOYSA-N buta-1,3-diene;prop-2-enenitrile Chemical compound C=CC=C.C=CC#N NTXGQCSETZTARF-UHFFFAOYSA-N 0.000 description 1
- QSWIMZICGKOGRT-UHFFFAOYSA-N butyl 2,3-dioxo-3-phenylpropanoate Chemical compound CCCCOC(=O)C(=O)C(=O)C1=CC=CC=C1 QSWIMZICGKOGRT-UHFFFAOYSA-N 0.000 description 1
- NULBTNYHRCDGHV-UHFFFAOYSA-N butyl 3,4-dioxobutanoate Chemical compound CCCCOC(=O)CC(=O)C=O NULBTNYHRCDGHV-UHFFFAOYSA-N 0.000 description 1
- 229920005549 butyl rubber Polymers 0.000 description 1
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- YACLQRRMGMJLJV-UHFFFAOYSA-N chloroprene Chemical compound ClC(=C)C=C YACLQRRMGMJLJV-UHFFFAOYSA-N 0.000 description 1
- 150000001925 cycloalkenes Chemical class 0.000 description 1
- MSNLXDBBWMSJSW-UHFFFAOYSA-N dibenzyl 2-oxopropanedioate Chemical compound C=1C=CC=CC=1COC(=O)C(=O)C(=O)OCC1=CC=CC=C1 MSNLXDBBWMSJSW-UHFFFAOYSA-N 0.000 description 1
- VVOCYQDSDXLBEA-UHFFFAOYSA-N dimethyl 2-oxopropanedioate Chemical compound COC(=O)C(=O)C(=O)OC VVOCYQDSDXLBEA-UHFFFAOYSA-N 0.000 description 1
- ISAKWFYKUTYAQE-UHFFFAOYSA-N dipropan-2-yl 2-oxopropanedioate Chemical compound CC(C)OC(=O)C(=O)C(=O)OC(C)C ISAKWFYKUTYAQE-UHFFFAOYSA-N 0.000 description 1
- BVEXQQTWYCTFSF-UHFFFAOYSA-N ditert-butyl 2-oxopropanedioate Chemical compound CC(C)(C)OC(=O)C(=O)C(=O)OC(C)(C)C BVEXQQTWYCTFSF-UHFFFAOYSA-N 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- GZFBWHHKTGCZCL-UHFFFAOYSA-N ethyl 2-cyano-2-oxoacetate Chemical compound CCOC(=O)C(=O)C#N GZFBWHHKTGCZCL-UHFFFAOYSA-N 0.000 description 1
- 229940015043 glyoxal Drugs 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- LLGMJHPMHFWMBF-UHFFFAOYSA-N methyl 2,3-dioxo-3-phenylpropanoate Chemical compound COC(=O)C(=O)C(=O)C1=CC=CC=C1 LLGMJHPMHFWMBF-UHFFFAOYSA-N 0.000 description 1
- JRLUDXADXLFJSR-UHFFFAOYSA-N methyl 2-cyano-2-oxoacetate Chemical compound COC(=O)C(=O)C#N JRLUDXADXLFJSR-UHFFFAOYSA-N 0.000 description 1
- YZIGEPHHZVOXNV-UHFFFAOYSA-N methyl 3,4-dioxobutanoate Chemical compound COC(=O)CC(=O)C=O YZIGEPHHZVOXNV-UHFFFAOYSA-N 0.000 description 1
- UHRQQTFNJGZLPK-UHFFFAOYSA-N methyl 3-(diethylamino)-2,3-dioxopropanoate Chemical compound CCN(CC)C(=O)C(=O)C(=O)OC UHRQQTFNJGZLPK-UHFFFAOYSA-N 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
- 229920003052 natural elastomer Polymers 0.000 description 1
- 229920001194 natural rubber Polymers 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- -1 oxomalonate ester Chemical class 0.000 description 1
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
- PMJHHCWVYXUKFD-UHFFFAOYSA-N piperylene Natural products CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 description 1
- 229920001084 poly(chloroprene) Polymers 0.000 description 1
- 229920006124 polyolefin elastomer Polymers 0.000 description 1
- 229920003246 polypentenamer Polymers 0.000 description 1
- 229920000346 polystyrene-polyisoprene block-polystyrene Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 150000003151 propanoic acid esters Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 229920000468 styrene butadiene styrene block copolymer Polymers 0.000 description 1
- 238000005987 sulfurization reaction Methods 0.000 description 1
- CNHWVFIZABCGJX-UHFFFAOYSA-N tert-butyl 2-cyano-2-oxoacetate Chemical compound CC(C)(C)OC(=O)C(=O)C#N CNHWVFIZABCGJX-UHFFFAOYSA-N 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 239000013585 weight reducing agent Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Landscapes
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9838983A JPS59223701A (ja) | 1983-06-02 | 1983-06-02 | ゴムの変性方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9838983A JPS59223701A (ja) | 1983-06-02 | 1983-06-02 | ゴムの変性方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS59223701A JPS59223701A (ja) | 1984-12-15 |
| JPH0469162B2 true JPH0469162B2 (fr) | 1992-11-05 |
Family
ID=14218489
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP9838983A Granted JPS59223701A (ja) | 1983-06-02 | 1983-06-02 | ゴムの変性方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS59223701A (fr) |
-
1983
- 1983-06-02 JP JP9838983A patent/JPS59223701A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS59223701A (ja) | 1984-12-15 |
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