JPH0768416B2 - ゴム加硫剤の製造法 - Google Patents
ゴム加硫剤の製造法Info
- Publication number
- JPH0768416B2 JPH0768416B2 JP62194271A JP19427187A JPH0768416B2 JP H0768416 B2 JPH0768416 B2 JP H0768416B2 JP 62194271 A JP62194271 A JP 62194271A JP 19427187 A JP19427187 A JP 19427187A JP H0768416 B2 JPH0768416 B2 JP H0768416B2
- Authority
- JP
- Japan
- Prior art keywords
- sulfur
- rubber
- olefin
- water
- vulcanizing agent
- 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 - Lifetime
Links
- 239000003795 chemical substances by application Substances 0.000 title claims description 20
- 238000004519 manufacturing process Methods 0.000 title claims description 9
- 229920001971 elastomer Polymers 0.000 title description 56
- 239000005060 rubber Substances 0.000 title description 51
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 91
- 229910052717 sulfur Inorganic materials 0.000 claims description 88
- 239000011593 sulfur Substances 0.000 claims description 88
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 28
- 239000000203 mixture Substances 0.000 claims description 28
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 26
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 claims description 25
- 150000001336 alkenes Chemical class 0.000 claims description 22
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 19
- 238000003756 stirring Methods 0.000 claims description 17
- 238000001816 cooling Methods 0.000 claims description 16
- 239000002270 dispersing agent Substances 0.000 claims description 12
- 238000010438 heat treatment Methods 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 9
- 229920001194 natural rubber Polymers 0.000 claims description 9
- 229920003051 synthetic elastomer Polymers 0.000 claims description 9
- 238000002156 mixing Methods 0.000 claims description 8
- 229920003052 natural elastomer Polymers 0.000 claims description 6
- 239000011541 reaction mixture Substances 0.000 claims description 6
- 239000005061 synthetic rubber Substances 0.000 claims description 5
- 244000043261 Hevea brasiliensis Species 0.000 claims description 3
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 20
- 239000000047 product Substances 0.000 description 17
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
- 239000011324 bead Substances 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 11
- 150000001993 dienes Chemical class 0.000 description 11
- 229910000019 calcium carbonate Inorganic materials 0.000 description 10
- 229910052757 nitrogen Inorganic materials 0.000 description 10
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 9
- 239000001768 carboxy methyl cellulose Substances 0.000 description 9
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 9
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 9
- 239000003054 catalyst Substances 0.000 description 9
- 239000000463 material Substances 0.000 description 9
- 229920001577 copolymer Polymers 0.000 description 8
- -1 poly (ethyleneoxy) -ethanol compounds Chemical class 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 7
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 6
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 6
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 6
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 6
- 239000004848 polyfunctional curative Substances 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 239000004615 ingredient Substances 0.000 description 5
- 230000000704 physical effect Effects 0.000 description 5
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- 150000002430 hydrocarbons Chemical class 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 3
- FXNDIJDIPNCZQJ-UHFFFAOYSA-N 2,4,4-trimethylpent-1-ene Chemical group CC(=C)CC(C)(C)C FXNDIJDIPNCZQJ-UHFFFAOYSA-N 0.000 description 3
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 3
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 3
- 239000005062 Polybutadiene Substances 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 239000000806 elastomer Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 229920002451 polyvinyl alcohol Polymers 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- 150000003673 urethanes Chemical class 0.000 description 3
- 238000004073 vulcanization Methods 0.000 description 3
- RRKODOZNUZCUBN-CCAGOZQPSA-N (1z,3z)-cycloocta-1,3-diene Chemical compound C1CC\C=C/C=C\C1 RRKODOZNUZCUBN-CCAGOZQPSA-N 0.000 description 2
- XWJBRBSPAODJER-UHFFFAOYSA-N 1,7-octadiene Chemical compound C=CCCCCC=C XWJBRBSPAODJER-UHFFFAOYSA-N 0.000 description 2
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 2
- DRHABPMHZRIRAH-UHFFFAOYSA-N 2,4,4,6,6-pentamethylhept-2-ene Chemical group CC(C)=CC(C)(C)CC(C)(C)C DRHABPMHZRIRAH-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- 239000004372 Polyvinyl alcohol Substances 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 125000005250 alkyl acrylate group Chemical group 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- UAHWPYUMFXYFJY-UHFFFAOYSA-N beta-myrcene Chemical compound CC(C)=CCCC(=C)C=C UAHWPYUMFXYFJY-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- YACLQRRMGMJLJV-UHFFFAOYSA-N chloroprene Chemical compound ClC(=C)C=C YACLQRRMGMJLJV-UHFFFAOYSA-N 0.000 description 2
- 238000013329 compounding Methods 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 238000007334 copolymerization reaction Methods 0.000 description 2
- MGNZXYYWBUKAII-UHFFFAOYSA-N cyclohexa-1,3-diene Chemical compound C1CC=CC=C1 MGNZXYYWBUKAII-UHFFFAOYSA-N 0.000 description 2
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 2
- LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 238000000227 grinding Methods 0.000 description 2
- 235000021388 linseed oil Nutrition 0.000 description 2
- 239000000944 linseed oil Substances 0.000 description 2
- 238000003801 milling Methods 0.000 description 2
- 150000002978 peroxides Chemical class 0.000 description 2
- 229920001084 poly(chloroprene) Polymers 0.000 description 2
- 229920002857 polybutadiene Polymers 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- 229920001897 terpolymer Polymers 0.000 description 2
- PPTXVXKCQZKFBN-UHFFFAOYSA-N (S)-(-)-1,1'-Bi-2-naphthol Chemical compound C1=CC=C2C(C3=C4C=CC=CC4=CC=C3O)=C(O)C=CC2=C1 PPTXVXKCQZKFBN-UHFFFAOYSA-N 0.000 description 1
- KEIFWROAQVVDBN-UHFFFAOYSA-N 1,2-dihydronaphthalene Chemical compound C1=CC=C2C=CCCC2=C1 KEIFWROAQVVDBN-UHFFFAOYSA-N 0.000 description 1
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical group C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 description 1
- HXKKHQJGJAFBHI-UHFFFAOYSA-N 1-aminopropan-2-ol Chemical compound CC(O)CN HXKKHQJGJAFBHI-UHFFFAOYSA-N 0.000 description 1
- SDRZFSPCVYEJTP-UHFFFAOYSA-N 1-ethenylcyclohexene Chemical compound C=CC1=CCCCC1 SDRZFSPCVYEJTP-UHFFFAOYSA-N 0.000 description 1
- HVTQDSGGHBWVTR-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-3-phenylmethoxypyrazol-1-yl]-1-morpholin-4-ylethanone Chemical compound C(C1=CC=CC=C1)OC1=NN(C=C1C=1C=NC(=NC=1)NC1CC2=CC=CC=C2C1)CC(=O)N1CCOCC1 HVTQDSGGHBWVTR-UHFFFAOYSA-N 0.000 description 1
- YHQXBTXEYZIYOV-UHFFFAOYSA-N 3-methylbut-1-ene Chemical compound CC(C)C=C YHQXBTXEYZIYOV-UHFFFAOYSA-N 0.000 description 1
- WTFUTSCZYYCBAY-SXBRIOAWSA-N 6-[(E)-C-[[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]methyl]-N-hydroxycarbonimidoyl]-3H-1,3-benzoxazol-2-one Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)C/C(=N/O)/C1=CC2=C(NC(O2)=O)C=C1 WTFUTSCZYYCBAY-SXBRIOAWSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- IMROMDMJAWUWLK-UHFFFAOYSA-N Ethenol Chemical compound OC=C IMROMDMJAWUWLK-UHFFFAOYSA-N 0.000 description 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- AYCPARAPKDAOEN-LJQANCHMSA-N N-[(1S)-2-(dimethylamino)-1-phenylethyl]-6,6-dimethyl-3-[(2-methyl-4-thieno[3,2-d]pyrimidinyl)amino]-1,4-dihydropyrrolo[3,4-c]pyrazole-5-carboxamide Chemical compound C1([C@H](NC(=O)N2C(C=3NN=C(NC=4C=5SC=CC=5N=C(C)N=4)C=3C2)(C)C)CN(C)C)=CC=CC=C1 AYCPARAPKDAOEN-LJQANCHMSA-N 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- 239000005864 Sulphur Substances 0.000 description 1
- SLINHMUFWFWBMU-UHFFFAOYSA-N Triisopropanolamine Chemical compound CC(O)CN(CC(C)O)CC(C)O SLINHMUFWFWBMU-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- VYBREYKSZAROCT-UHFFFAOYSA-N alpha-myrcene Natural products CC(=C)CCCC(=C)C=C VYBREYKSZAROCT-UHFFFAOYSA-N 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 239000012431 aqueous reaction media Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000013068 control sample Substances 0.000 description 1
- 150000001925 cycloalkenes Chemical class 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 229920003244 diene elastomer Polymers 0.000 description 1
- 238000000113 differential scanning calorimetry Methods 0.000 description 1
- LVTYICIALWPMFW-UHFFFAOYSA-N diisopropanolamine Chemical compound CC(O)CNCC(C)O LVTYICIALWPMFW-UHFFFAOYSA-N 0.000 description 1
- 229940043276 diisopropanolamine Drugs 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000010907 mechanical stirring Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920006149 polyester-amide block copolymer Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920001195 polyisoprene Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 238000010057 rubber processing Methods 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 150000003463 sulfur Chemical class 0.000 description 1
- 239000002344 surface layer Substances 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
- 239000012745 toughening agent Substances 0.000 description 1
- IAQRGUVFOMOMEM-ONEGZZNKSA-N trans-but-2-ene Chemical compound C\C=C\C IAQRGUVFOMOMEM-ONEGZZNKSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000004636 vulcanized rubber Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L21/00—Compositions of unspecified rubbers
-
- 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
- C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07G—COMPOUNDS OF UNKNOWN CONSTITUTION
- C07G99/00—Subject matter not provided for in other groups of this subclass
- C07G99/002—Compounds of unknown constitution containing sulfur
- C07G99/0022—Compounds of unknown constitution containing sulfur derived from hydrocarbons
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Processes Of Treating Macromolecular Substances (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/896,688 US4739036A (en) | 1986-08-15 | 1986-08-15 | Rubber vulcanization agents and methods for their preparation |
| US896688 | 1986-08-15 |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP7015337A Division JP2530116B2 (ja) | 1986-08-15 | 1995-02-01 | ゴム加硫物の製造法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6348343A JPS6348343A (ja) | 1988-03-01 |
| JPH0768416B2 true JPH0768416B2 (ja) | 1995-07-26 |
Family
ID=25406641
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP62194271A Expired - Lifetime JPH0768416B2 (ja) | 1986-08-15 | 1987-08-03 | ゴム加硫剤の製造法 |
| JP7015337A Expired - Lifetime JP2530116B2 (ja) | 1986-08-15 | 1995-02-01 | ゴム加硫物の製造法 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP7015337A Expired - Lifetime JP2530116B2 (ja) | 1986-08-15 | 1995-02-01 | ゴム加硫物の製造法 |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US4739036A (en]) |
| EP (1) | EP0258168B1 (en]) |
| JP (2) | JPH0768416B2 (en]) |
| KR (1) | KR960001618B1 (en]) |
| AR (1) | AR244731A1 (en]) |
| AU (1) | AU591417B2 (en]) |
| BR (1) | BR8704105A (en]) |
| CA (1) | CA1324450C (en]) |
| DE (1) | DE3751649T2 (en]) |
| ES (1) | ES2083356T4 (en]) |
| IL (1) | IL83518A (en]) |
| IN (1) | IN168535B (en]) |
| MX (1) | MX7575A (en]) |
| NO (1) | NO169657C (en]) |
| TR (1) | TR22884A (en]) |
| ZA (1) | ZA875694B (en]) |
Families Citing this family (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4902775A (en) * | 1986-08-15 | 1990-02-20 | The Goodyear Tire & Rubber Company | Rubber vulcanization agents of sulfur olefin adduct |
| DE3640938A1 (de) * | 1986-11-29 | 1988-06-01 | Boehringer Mannheim Gmbh | Neue diphosphonsaeurederivate, verfahren zu deren herstellung und diese verbindung enthaltende arzneimittel |
| US5710218A (en) * | 1989-10-05 | 1998-01-20 | Mitsui Petrochemical Industries | Ethylene-propylene-diene rubber, elastomer composition and vulcanized rubber thereof |
| US5703165A (en) * | 1992-12-18 | 1997-12-30 | Saynad Corporation | Method of achieving superior dispersions of insoluble sulfur and products thereof |
| US5475059A (en) * | 1992-12-18 | 1995-12-12 | Saynad Corporation | Method of achieving superior dispersions of polymeric sulfur and products thereof |
| FR2712824B1 (fr) * | 1993-11-26 | 1996-02-02 | Inst Francais Du Petrole | Procédé de régénération de catalyseur. |
| FR2727425A1 (fr) * | 1994-11-28 | 1996-05-31 | Inst Francais Du Petrole | Hydrocarbures ethyleniques sulfures par le soufre elementaire en presence d'eau et d'hydroxyde alcalin ou alcalino-terreux, leur preparation et leur utilisation |
| FR2727427B1 (fr) * | 1994-11-28 | 1997-04-25 | Inst Francais Du Petrole | Hydrocarbures ethyleniques sulfures par le soufre elementaire en presence d'alkyleneglycols ou de derives d'alkyleneglycols et d'hydroxydes de metaux alcalins ou alcalino-terreux, leur preparation et leur utilisation |
| EP0714970A1 (fr) * | 1994-11-28 | 1996-06-05 | Institut Français du Pétrole | Hydrocarbures éthyléniques sulfurés par le soufre élémentaire en présence d'hydroxydes de métaux alcalins ou alcalino-terreux et en présence de glycols, polyglycols ou de leurs éthers alkyliques et/ou en présence d'eau |
| FR2729154A1 (fr) * | 1995-01-10 | 1996-07-12 | Inst Francais Du Petrole | Hydrocarbures ethyleniques sulfures par le soufre elementaire en presence de carbonate ou d'hydrogenocarbonate alcalin, leur preparation et leurs utilisations |
| FR2746409B1 (fr) * | 1996-03-19 | 1998-04-17 | Inst Francais Du Petrole | Procede de sulfuration de corps gras insatures par le soufre elementaire en presence de composes amines |
| US6357499B1 (en) | 1998-10-02 | 2002-03-19 | The Goodyear Tire & Rubber Company | Polymeric resinous material derived from limonene, dicyclopentadiene, indene and tertiary-butyl styrene |
| US6245873B1 (en) | 1999-02-09 | 2001-06-12 | The Goodyear Tire & Rubber Company | Polymeric dicyclopentadiene/limonene resin |
| US6221990B1 (en) | 1999-02-16 | 2001-04-24 | The Goodyear Tire & Rubber Company | Polymeric resinous material derived from limonene, dicyclopentadiene and tertiary-butyl styrene |
| US6242550B1 (en) | 1999-05-07 | 2001-06-05 | The Goodyear Tire & Rubber Company | Polymeric dimethyl- dicyclopentadiene/limonene resin |
| US6228944B1 (en) | 1999-06-24 | 2001-05-08 | The Goodyear Tire & Rubber Company | Polymeric resinous material derived from limonene, dimethyl-dicyclopentadiene, indene and vinyl toluene |
| US6265478B1 (en) | 1999-08-18 | 2001-07-24 | The Goodyear Tire & Rubber Company | Polymeric resinous material derived from limonene dicyclopentadiene indene and alpha-methyl styrene |
| US6201059B1 (en) | 1999-08-19 | 2001-03-13 | The Goodyear Tire & Rubber Company | Pneumatic tire having a tread containing dicyclopentadiene/beta-pinene resin |
| DE10002878C1 (de) * | 2000-01-24 | 2001-09-06 | Bayer Ag | Neue Vulkanisationsmittel für ungesättigte Kautschukmischungen |
| JP2003525318A (ja) * | 2000-02-15 | 2003-08-26 | ビーエーエスエフ アクチェンゲゼルシャフト | ポリアルキレンポリスルフィド |
| JP2002371156A (ja) * | 2001-04-10 | 2002-12-26 | Yokohama Rubber Co Ltd:The | ゴム組成物 |
| DE10134686A1 (de) * | 2001-07-20 | 2003-02-06 | Bayer Ag | Verfahren zur Herstellung von polymeren Schwefelverbindungen |
| WO2006134130A1 (en) * | 2005-06-17 | 2006-12-21 | Shell Internationale Research Maatschappij B.V. | Modified sulphur and product comprising modified sulphur as binder |
| US11795248B2 (en) | 2011-08-11 | 2023-10-24 | Arizona Board Of Regents On Behalf Of The University Of Arizona | Copolymerization of elemental sulfur and epoxy functional styrenics |
| US11015023B2 (en) * | 2011-08-11 | 2021-05-25 | Arizona Board Of Regents On Behalf Of The University Of Arizona | Fire retardant compositions utilizing elemental sulfur |
| US10752764B2 (en) * | 2014-12-09 | 2020-08-25 | Arkema Inc. | Compositions and methods for crosslinking polymers in the presence of atmospheric oxygen |
| WO2020054238A1 (ja) * | 2018-09-11 | 2020-03-19 | 株式会社ブリヂストン | ゴム組成物及びタイヤ |
| JP6661156B1 (ja) | 2019-09-13 | 2020-03-11 | 株式会社Ｔｂｍ | 生分解性ゴム組成物、生分解性ゴム組成物の製造方法及び生分解性ゴム成形品 |
| WO2024261552A1 (en) * | 2023-06-19 | 2024-12-26 | Nocil Ltd. | Novel cross-linking agent for rubber and process for its preparation |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2410595A (en) * | 1943-05-18 | 1946-11-05 | Texas Gulf Sulphur Co | Rubberlike products |
| NL246116A (en]) * | 1958-12-15 | |||
| US3523926A (en) * | 1967-11-08 | 1970-08-11 | Stauffer Chemical Co | Rubber vulcanization agents and methods for their preparation |
| US4190460A (en) * | 1978-04-03 | 1980-02-26 | Suntech, Inc. | Sulfur plasticization with olefins |
| US4475953A (en) * | 1983-02-24 | 1984-10-09 | Southwest Research Institute | Emulsion and method of making same |
-
1986
- 1986-08-15 US US06/896,688 patent/US4739036A/en not_active Expired - Lifetime
-
1987
- 1987-06-11 IN IN504/DEL/87A patent/IN168535B/en unknown
- 1987-07-28 DE DE3751649T patent/DE3751649T2/de not_active Expired - Fee Related
- 1987-07-28 ES ES87630129T patent/ES2083356T4/es not_active Expired - Lifetime
- 1987-07-28 EP EP87630129A patent/EP0258168B1/en not_active Expired - Lifetime
- 1987-07-31 AR AR87308320A patent/AR244731A1/es active
- 1987-07-31 ZA ZA875694A patent/ZA875694B/xx unknown
- 1987-08-03 JP JP62194271A patent/JPH0768416B2/ja not_active Expired - Lifetime
- 1987-08-03 MX MX757587A patent/MX7575A/es unknown
- 1987-08-10 BR BR8704105A patent/BR8704105A/pt not_active IP Right Cessation
- 1987-08-10 TR TR554/87A patent/TR22884A/xx unknown
- 1987-08-12 IL IL83518A patent/IL83518A/xx not_active IP Right Cessation
- 1987-08-14 CA CA000544549A patent/CA1324450C/en not_active Expired - Fee Related
- 1987-08-14 NO NO873425A patent/NO169657C/no unknown
- 1987-08-14 KR KR1019870008917A patent/KR960001618B1/ko not_active Expired - Fee Related
- 1987-08-14 AU AU76891/87A patent/AU591417B2/en not_active Ceased
-
1995
- 1995-02-01 JP JP7015337A patent/JP2530116B2/ja not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| AR244731A1 (es) | 1993-11-30 |
| EP0258168B1 (en) | 1995-12-27 |
| IL83518A0 (en) | 1988-01-31 |
| IL83518A (en) | 1990-12-23 |
| KR880002918A (ko) | 1988-05-12 |
| NO873425L (no) | 1988-02-16 |
| JP2530116B2 (ja) | 1996-09-04 |
| AU7689187A (en) | 1988-02-18 |
| ZA875694B (en) | 1988-02-11 |
| TR22884A (tr) | 1988-10-03 |
| US4739036A (en) | 1988-04-19 |
| EP0258168A1 (en) | 1988-03-02 |
| ES2083356T3 (es) | 1996-04-16 |
| ES2083356T4 (es) | 1996-06-01 |
| BR8704105A (pt) | 1988-04-12 |
| MX7575A (es) | 1994-02-28 |
| KR960001618B1 (ko) | 1996-02-03 |
| JPH07309977A (ja) | 1995-11-28 |
| NO169657C (no) | 1992-07-22 |
| JPS6348343A (ja) | 1988-03-01 |
| AU591417B2 (en) | 1989-11-30 |
| NO169657B (no) | 1992-04-13 |
| CA1324450C (en) | 1993-11-16 |
| DE3751649D1 (de) | 1996-02-08 |
| NO873425D0 (no) | 1987-08-14 |
| IN168535B (en]) | 1991-04-20 |
| DE3751649T2 (de) | 1996-07-18 |
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