JPS5817132A - ゴム組成物 - Google Patents
ゴム組成物Info
- Publication number
- JPS5817132A JPS5817132A JP57116309A JP11630982A JPS5817132A JP S5817132 A JPS5817132 A JP S5817132A JP 57116309 A JP57116309 A JP 57116309A JP 11630982 A JP11630982 A JP 11630982A JP S5817132 A JPS5817132 A JP S5817132A
- Authority
- JP
- Japan
- Prior art keywords
- group
- formula
- composition according
- compound
- ion
- 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.)
- Granted
Links
- GWIKYPMLNBTJHR-UHFFFAOYSA-M thiosulfonate group Chemical group S(=S)(=O)[O-] GWIKYPMLNBTJHR-UHFFFAOYSA-M 0.000 title description 11
- 150000004764 thiosulfuric acid derivatives Chemical class 0.000 title description 8
- 150000001875 compounds Chemical class 0.000 claims description 100
- 239000000203 mixture Substances 0.000 claims description 91
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 90
- -1 4-phenylaminophenyl group Chemical group 0.000 claims description 67
- 239000003381 stabilizer Substances 0.000 claims description 56
- 125000000217 alkyl group Chemical group 0.000 claims description 54
- 229910001868 water Inorganic materials 0.000 claims description 49
- 150000002500 ions Chemical class 0.000 claims description 39
- 239000000126 substance Substances 0.000 claims description 36
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 31
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 28
- 239000002585 base Substances 0.000 claims description 27
- 229920001971 elastomer Polymers 0.000 claims description 26
- 238000000034 method Methods 0.000 claims description 26
- 229910052717 sulfur Inorganic materials 0.000 claims description 26
- 238000004073 vulcanization Methods 0.000 claims description 26
- 239000005060 rubber Substances 0.000 claims description 25
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 23
- 239000011593 sulfur Substances 0.000 claims description 23
- 229920000642 polymer Polymers 0.000 claims description 20
- 159000000000 sodium salts Chemical class 0.000 claims description 19
- 229910052708 sodium Inorganic materials 0.000 claims description 17
- 125000002947 alkylene group Chemical group 0.000 claims description 16
- 239000011734 sodium Substances 0.000 claims description 16
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group 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 claims description 15
- 229910052783 alkali metal Inorganic materials 0.000 claims description 15
- 229910052751 metal Inorganic materials 0.000 claims description 15
- 239000002184 metal Substances 0.000 claims description 15
- 229910052759 nickel Inorganic materials 0.000 claims description 13
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 11
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims description 10
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 9
- 238000002425 crystallisation Methods 0.000 claims description 9
- 230000008025 crystallization Effects 0.000 claims description 9
- 239000000463 material Substances 0.000 claims description 9
- 229910052725 zinc Inorganic materials 0.000 claims description 9
- 239000011701 zinc Substances 0.000 claims description 9
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 8
- 230000000704 physical effect Effects 0.000 claims description 8
- 239000013078 crystal Substances 0.000 claims description 7
- URMSIZAJUFVFFU-UHFFFAOYSA-N hydroxy-(6-hydroxysulfonothioyloxyhexoxy)-oxo-sulfanylidene-lambda6-sulfane Chemical compound OS(=O)(=S)OCCCCCCOS(O)(=O)=S URMSIZAJUFVFFU-UHFFFAOYSA-N 0.000 claims description 7
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 7
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 6
- 150000001340 alkali metals Chemical class 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 239000011575 calcium Substances 0.000 claims description 6
- 229910052791 calcium Inorganic materials 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 229910017052 cobalt Inorganic materials 0.000 claims description 6
- 239000010941 cobalt Substances 0.000 claims description 6
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 6
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 6
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 5
- 125000004429 atom Chemical group 0.000 claims description 5
- 238000004132 cross linking Methods 0.000 claims description 5
- 238000010438 heat treatment Methods 0.000 claims description 5
- 229910052749 magnesium Inorganic materials 0.000 claims description 5
- 239000011777 magnesium Substances 0.000 claims description 5
- 125000000962 organic group Chemical group 0.000 claims description 5
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 4
- 229910052788 barium Inorganic materials 0.000 claims description 4
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 claims description 4
- 229920000620 organic polymer Polymers 0.000 claims description 4
- 229920001195 polyisoprene Polymers 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical group [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 3
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical group [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 3
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims description 3
- 150000002357 guanidines Chemical class 0.000 claims description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims description 3
- 229910052744 lithium Inorganic materials 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 229920002451 polyvinyl alcohol Polymers 0.000 claims description 3
- 235000019422 polyvinyl alcohol Nutrition 0.000 claims description 3
- 229910052700 potassium Chemical group 0.000 claims description 3
- 239000011591 potassium Chemical group 0.000 claims description 3
- 125000004434 sulfur atom Chemical group 0.000 claims description 3
- 125000000732 arylene group Chemical group 0.000 claims description 2
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 2
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052737 gold Inorganic materials 0.000 claims description 2
- 239000010931 gold Substances 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims 3
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 claims 2
- 101100356682 Caenorhabditis elegans rho-1 gene Proteins 0.000 claims 1
- AHJKRLASYNVKDZ-UHFFFAOYSA-N DDD Chemical group C=1C=C(Cl)C=CC=1C(C(Cl)Cl)C1=CC=C(Cl)C=C1 AHJKRLASYNVKDZ-UHFFFAOYSA-N 0.000 claims 1
- 241001214257 Mene Species 0.000 claims 1
- 241000277331 Salmonidae Species 0.000 claims 1
- 229910000831 Steel Inorganic materials 0.000 claims 1
- FQNGWRSKYZLJDK-UHFFFAOYSA-N [Ca].[Ba] Chemical compound [Ca].[Ba] FQNGWRSKYZLJDK-UHFFFAOYSA-N 0.000 claims 1
- 239000003513 alkali Substances 0.000 claims 1
- 125000004965 chloroalkyl group Chemical group 0.000 claims 1
- 125000004185 ester group Chemical group 0.000 claims 1
- ISNICOKBNZOJQG-UHFFFAOYSA-O guanidinium ion Chemical compound C[NH+]=C(N(C)C)N(C)C ISNICOKBNZOJQG-UHFFFAOYSA-O 0.000 claims 1
- 239000011133 lead Substances 0.000 claims 1
- 150000002736 metal compounds Chemical class 0.000 claims 1
- 150000002739 metals Chemical class 0.000 claims 1
- SDCIHPIYZXQRPM-UHFFFAOYSA-L nickel(2+);oxido-(6-oxidosulfonothioyloxyhexoxy)-oxo-sulfanylidene-$l^{6}-sulfane Chemical compound [Ni+2].[O-]S(=O)(=S)OCCCCCCOS([O-])(=O)=S SDCIHPIYZXQRPM-UHFFFAOYSA-L 0.000 claims 1
- 235000012149 noodles Nutrition 0.000 claims 1
- 229920001290 polyvinyl ester Polymers 0.000 claims 1
- 239000010959 steel Substances 0.000 claims 1
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims 1
- 125000004354 sulfur functional group Chemical group 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 75
- 239000000243 solution Substances 0.000 description 56
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 42
- DHCDFWKWKRSZHF-UHFFFAOYSA-L thiosulfate(2-) Chemical group [O-]S([S-])(=O)=O DHCDFWKWKRSZHF-UHFFFAOYSA-L 0.000 description 37
- 239000000047 product Substances 0.000 description 32
- 238000006243 chemical reaction Methods 0.000 description 26
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 24
- 150000003839 salts Chemical group 0.000 description 20
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical group CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 238000004519 manufacturing process Methods 0.000 description 14
- 239000007787 solid Substances 0.000 description 14
- 150000001412 amines Chemical class 0.000 description 13
- 238000002360 preparation method Methods 0.000 description 13
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 12
- 239000004594 Masterbatch (MB) Substances 0.000 description 11
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 11
- 239000011541 reaction mixture Substances 0.000 description 11
- 235000019345 sodium thiosulphate Nutrition 0.000 description 11
- 150000001768 cations Chemical class 0.000 description 10
- 239000007788 liquid Substances 0.000 description 10
- 238000002844 melting Methods 0.000 description 10
- MHKLKWCYGIBEQF-UHFFFAOYSA-N 4-(1,3-benzothiazol-2-ylsulfanyl)morpholine Chemical compound C1COCCN1SC1=NC2=CC=CC=C2S1 MHKLKWCYGIBEQF-UHFFFAOYSA-N 0.000 description 9
- 238000000921 elemental analysis Methods 0.000 description 9
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 9
- 230000008018 melting Effects 0.000 description 9
- 244000043261 Hevea brasiliensis Species 0.000 description 8
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
- 238000010521 absorption reaction Methods 0.000 description 8
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 8
- 229920003052 natural elastomer Polymers 0.000 description 8
- 229920001194 natural rubber Polymers 0.000 description 8
- 239000002244 precipitate Substances 0.000 description 8
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 230000014759 maintenance of location Effects 0.000 description 7
- 239000012429 reaction media Substances 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- 239000000460 chlorine Substances 0.000 description 6
- 229910052801 chlorine Inorganic materials 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- ZPXFNYXNJOHABQ-UHFFFAOYSA-M sodium 1-dimethylsilylpropane-1-sulfonate Chemical compound [Na+].C[SiH](C)C(CC)S(=O)(=O)[O-] ZPXFNYXNJOHABQ-UHFFFAOYSA-M 0.000 description 6
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 5
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 5
- 159000000009 barium salts Chemical class 0.000 description 5
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- 239000003729 cation exchange resin Substances 0.000 description 5
- 150000001868 cobalt Chemical class 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- RCGBHLSDSJSVGM-UHFFFAOYSA-L disodium;oxido-(6-oxidosulfonothioyloxyhexoxy)-oxo-sulfanylidene-$l^{6}-sulfane;dihydrate Chemical compound O.O.[Na+].[Na+].[O-]S(=O)(=S)OCCCCCCOS([O-])(=O)=S RCGBHLSDSJSVGM-UHFFFAOYSA-L 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 229910052736 halogen Inorganic materials 0.000 description 5
- 150000002367 halogens Chemical class 0.000 description 5
- 238000005259 measurement Methods 0.000 description 5
- 150000002815 nickel Chemical class 0.000 description 5
- 238000006467 substitution reaction Methods 0.000 description 5
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 229920003244 diene elastomer Polymers 0.000 description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 150000002334 glycols Chemical class 0.000 description 4
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 239000010734 process oil Substances 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- 239000002002 slurry Substances 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- VUBDYLKZHRQEBS-UHFFFAOYSA-N 1,4-bis(chloromethyl)cyclohexane Chemical compound ClCC1CCC(CCl)CC1 VUBDYLKZHRQEBS-UHFFFAOYSA-N 0.000 description 3
- CDIIZULDSLKBKV-UHFFFAOYSA-N 4-chlorobutanoyl chloride Chemical compound ClCCCC(Cl)=O CDIIZULDSLKBKV-UHFFFAOYSA-N 0.000 description 3
- FCMCSZXRVWDVAW-UHFFFAOYSA-N 6-bromo-1-hexanol Chemical compound OCCCCCCBr FCMCSZXRVWDVAW-UHFFFAOYSA-N 0.000 description 3
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 3
- 235000021355 Stearic acid Nutrition 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 230000003679 aging effect Effects 0.000 description 3
- 230000001476 alcoholic effect Effects 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 239000003963 antioxidant agent Substances 0.000 description 3
- 230000009286 beneficial effect Effects 0.000 description 3
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 3
- 239000004305 biphenyl Substances 0.000 description 3
- 235000010290 biphenyl Nutrition 0.000 description 3
- 150000001721 carbon Chemical group 0.000 description 3
- 238000005341 cation exchange Methods 0.000 description 3
- FGRVOLIFQGXPCT-UHFFFAOYSA-L dipotassium;dioxido-oxo-sulfanylidene-$l^{6}-sulfane Chemical compound [K+].[K+].[O-]S([O-])(=O)=S FGRVOLIFQGXPCT-UHFFFAOYSA-L 0.000 description 3
- SRBDFEUJIIOBRK-UHFFFAOYSA-L disodium oxido-(2-oxidosulfonothioyloxyethoxy)-oxo-sulfanylidene-lambda6-sulfane hydrate Chemical compound O.[Na+].[Na+].S(=S)(=O)(OCCOS(=S)(=O)[O-])[O-] SRBDFEUJIIOBRK-UHFFFAOYSA-L 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- ZRALSGWEFCBTJO-UHFFFAOYSA-O guanidinium Chemical compound NC(N)=[NH2+] ZRALSGWEFCBTJO-UHFFFAOYSA-O 0.000 description 3
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 3
- 239000010410 layer Substances 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 3
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- 239000008117 stearic acid Substances 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 3
- 150000003751 zinc Chemical class 0.000 description 3
- OWRCNXZUPFZXOS-UHFFFAOYSA-N 1,3-diphenylguanidine Chemical compound C=1C=CC=CC=1NC(=N)NC1=CC=CC=C1 OWRCNXZUPFZXOS-UHFFFAOYSA-N 0.000 description 2
- ZRMMVODKVLXCBB-UHFFFAOYSA-N 1-n-cyclohexyl-4-n-phenylbenzene-1,4-diamine Chemical compound C1CCCCC1NC(C=C1)=CC=C1NC1=CC=CC=C1 ZRMMVODKVLXCBB-UHFFFAOYSA-N 0.000 description 2
- AHVQWUYSFDDRTM-UHFFFAOYSA-N 2,2-bis(sulfanylidene)-1,3,2-dioxathiecane Chemical compound S1(=S)(=S)OCCCCCCCO1 AHVQWUYSFDDRTM-UHFFFAOYSA-N 0.000 description 2
- VNFNYMOHQCMCFC-UHFFFAOYSA-N 2,2-bis(sulfanylidene)-1,3-dioxa-2lambda6-thiacyclotridecane Chemical compound S1(=S)(=S)OCCCCCCCCCCO1 VNFNYMOHQCMCFC-UHFFFAOYSA-N 0.000 description 2
- NVRVNSHHLPQGCU-UHFFFAOYSA-N 6-bromohexanoic acid Chemical compound OC(=O)CCCCCBr NVRVNSHHLPQGCU-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- 244000241257 Cucumis melo Species 0.000 description 2
- 235000015510 Cucumis melo subsp melo Nutrition 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 2
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- 239000012466 permeate Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- RMVRSNDYEFQCLF-UHFFFAOYSA-N phenyl mercaptan Natural products SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 1
- 238000013031 physical testing Methods 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000006235 reinforcing carbon black Substances 0.000 description 1
- 102220076631 rs376146751 Human genes 0.000 description 1
- GPNLWUFFWOYKLP-UHFFFAOYSA-N s-(1,3-benzothiazol-2-yl)thiohydroxylamine Chemical group C1=CC=C2SC(SN)=NC2=C1 GPNLWUFFWOYKLP-UHFFFAOYSA-N 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- BWAUQTFFVCLSOS-UHFFFAOYSA-N sodiosodium hydrate Chemical compound O.[Na].[Na] BWAUQTFFVCLSOS-UHFFFAOYSA-N 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- UOULCEYHQNCFFH-UHFFFAOYSA-M sodium;hydroxymethanesulfonate Chemical compound [Na+].OCS([O-])(=O)=O UOULCEYHQNCFFH-UHFFFAOYSA-M 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000005987 sulfurization reaction Methods 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 238000003878 thermal aging Methods 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 239000004636 vulcanized rubber Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Landscapes
- Compositions Of Macromolecular Compounds (AREA)
- Anti-Oxidant Or Stabilizer Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8121098 | 1981-07-08 | ||
| GB8121098 | 1981-07-08 | ||
| GB8124716 | 1981-08-13 |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2233442A Division JPH03115259A (ja) | 1981-07-08 | 1990-09-05 | 有機チオスルフエート類 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5817132A true JPS5817132A (ja) | 1983-02-01 |
| JPH0332576B2 JPH0332576B2 (enExample) | 1991-05-13 |
Family
ID=10523100
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP57116309A Granted JPS5817132A (ja) | 1981-07-08 | 1982-07-06 | ゴム組成物 |
Country Status (3)
| Country | Link |
|---|---|
| JP (1) | JPS5817132A (enExample) |
| HU (1) | HU191815B (enExample) |
| ZA (1) | ZA824806B (enExample) |
Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5991140A (ja) * | 1982-10-21 | 1984-05-25 | モンサント・ヨ−ロツプ・ソシエテ・アノニム | ゴム／金属複合物 |
| JP2005298512A (ja) * | 2004-04-15 | 2005-10-27 | Lanxess Deutschland Gmbh | チオ硫酸誘導体の製造法 |
| JP2006306779A (ja) * | 2005-04-28 | 2006-11-09 | Ube Ind Ltd | ジチオスルフェート化合物の製造方法 |
| JP2008530389A (ja) * | 2005-02-18 | 2008-08-07 | テイジン・アラミド・ビー．ブイ． | ブンテ塩で処理された繊維を用いることによってゴム特性を強化するための方法 |
| WO2010140704A1 (ja) * | 2009-06-04 | 2010-12-09 | 住友化学株式会社 | Ｓ－（３－アミノプロピル）チオ硫酸またはその金属塩の使用 |
| WO2011001990A1 (ja) * | 2009-06-30 | 2011-01-06 | 住友化学株式会社 | 加硫ゴム及びその製造方法 |
| WO2012002517A1 (ja) * | 2010-06-30 | 2012-01-05 | 住友化学株式会社 | Ｓ－（３－アミノプロピル）チオ硫酸および／またはその金属塩の使用方法 |
| WO2012002521A1 (ja) * | 2010-06-30 | 2012-01-05 | 住友化学株式会社 | 加硫ゴム組成物の製造方法 |
| WO2012057365A1 (ja) * | 2010-10-29 | 2012-05-03 | 住友化学株式会社 | 加硫ゴム組成物の製造方法 |
| WO2013018815A1 (ja) * | 2011-08-01 | 2013-02-07 | 住友化学株式会社 | 加硫ゴムの動倍率低下方法 |
| WO2015147179A1 (ja) * | 2014-03-27 | 2015-10-01 | 横浜ゴム株式会社 | ゴム組成物及びこれを用いる空気入りタイヤ |
| CN106068342A (zh) * | 2014-03-10 | 2016-11-02 | 日东纺绩株式会社 | 玻璃纤维短切原丝毡、玻璃纤维短切原丝毡卷、玻璃纤维短切原丝毡的制造方法及汽车成形顶棚材料 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS56159235A (en) * | 1980-04-17 | 1981-12-08 | Bayer Ag | Vulcanization system, rubber mixture and vulcanization |
-
1982
- 1982-07-06 JP JP57116309A patent/JPS5817132A/ja active Granted
- 1982-07-06 ZA ZA824806A patent/ZA824806B/xx unknown
- 1982-07-07 HU HU822216A patent/HU191815B/hu not_active IP Right Cessation
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS56159235A (en) * | 1980-04-17 | 1981-12-08 | Bayer Ag | Vulcanization system, rubber mixture and vulcanization |
Cited By (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5991140A (ja) * | 1982-10-21 | 1984-05-25 | モンサント・ヨ−ロツプ・ソシエテ・アノニム | ゴム／金属複合物 |
| JP2005298512A (ja) * | 2004-04-15 | 2005-10-27 | Lanxess Deutschland Gmbh | チオ硫酸誘導体の製造法 |
| JP2008530389A (ja) * | 2005-02-18 | 2008-08-07 | テイジン・アラミド・ビー．ブイ． | ブンテ塩で処理された繊維を用いることによってゴム特性を強化するための方法 |
| JP2006306779A (ja) * | 2005-04-28 | 2006-11-09 | Ube Ind Ltd | ジチオスルフェート化合物の製造方法 |
| US8664432B2 (en) | 2009-06-04 | 2014-03-04 | Sumitomo Chemical Company, Limited | Use of S-(3-aminopropyl)thiosulfuric acid or metal salt thereof |
| WO2010140704A1 (ja) * | 2009-06-04 | 2010-12-09 | 住友化学株式会社 | Ｓ－（３－アミノプロピル）チオ硫酸またはその金属塩の使用 |
| JP2011202137A (ja) * | 2009-06-04 | 2011-10-13 | Sumitomo Chemical Co Ltd | 加硫ゴムが有する粘弾性特性を改善させるためのｓ−（３−アミノプロピル）チオ硫酸および／またはその金属塩の使用 |
| JP2012126923A (ja) * | 2009-06-04 | 2012-07-05 | Sumitomo Chemical Co Ltd | 加硫ゴムが有する粘弾性特性を改善させるためのｓ−（３−アミノプロピル）チオ硫酸および／またはその金属塩の使用 |
| WO2011001990A1 (ja) * | 2009-06-30 | 2011-01-06 | 住友化学株式会社 | 加硫ゴム及びその製造方法 |
| JP2011202138A (ja) * | 2009-06-30 | 2011-10-13 | Sumitomo Chemical Co Ltd | 加硫ゴム及びその製造方法 |
| WO2012002517A1 (ja) * | 2010-06-30 | 2012-01-05 | 住友化学株式会社 | Ｓ－（３－アミノプロピル）チオ硫酸および／またはその金属塩の使用方法 |
| WO2012002521A1 (ja) * | 2010-06-30 | 2012-01-05 | 住友化学株式会社 | 加硫ゴム組成物の製造方法 |
| WO2012057365A1 (ja) * | 2010-10-29 | 2012-05-03 | 住友化学株式会社 | 加硫ゴム組成物の製造方法 |
| WO2013018815A1 (ja) * | 2011-08-01 | 2013-02-07 | 住友化学株式会社 | 加硫ゴムの動倍率低下方法 |
| CN106068342A (zh) * | 2014-03-10 | 2016-11-02 | 日东纺绩株式会社 | 玻璃纤维短切原丝毡、玻璃纤维短切原丝毡卷、玻璃纤维短切原丝毡的制造方法及汽车成形顶棚材料 |
| CN106068342B (zh) * | 2014-03-10 | 2017-06-16 | 日东纺绩株式会社 | 玻璃纤维短切原丝毡、玻璃纤维短切原丝毡卷、玻璃纤维短切原丝毡的制造方法及汽车成形顶棚材料 |
| US10160403B2 (en) | 2014-03-10 | 2018-12-25 | Nitto Boseki Co., Ltd. | Glass chopped strand mat, glass chopped strand mat roll, method for manufacturing glass chopped strand mat and automotive molded ceiling material |
| US10196011B2 (en) | 2014-03-10 | 2019-02-05 | Nitto Boseki Co., Ltd. | Glass chopped strand mat, glass chopped strand mat roll, method for manufacturing glass chopped strand mat and automotive molded ceiling material |
| WO2015147179A1 (ja) * | 2014-03-27 | 2015-10-01 | 横浜ゴム株式会社 | ゴム組成物及びこれを用いる空気入りタイヤ |
| JP2015189833A (ja) * | 2014-03-27 | 2015-11-02 | 横浜ゴム株式会社 | ゴム組成物及びこれを用いる空気入りタイヤ |
Also Published As
| Publication number | Publication date |
|---|---|
| ZA824806B (en) | 1983-04-27 |
| HU191815B (en) | 1987-04-28 |
| JPH0332576B2 (enExample) | 1991-05-13 |
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