JP4993378B2 - 加硫促進剤、ゴム組成物およびそれを用いたタイヤ - Google Patents
加硫促進剤、ゴム組成物およびそれを用いたタイヤ Download PDFInfo
- Publication number
- JP4993378B2 JP4993378B2 JP2008086728A JP2008086728A JP4993378B2 JP 4993378 B2 JP4993378 B2 JP 4993378B2 JP 2008086728 A JP2008086728 A JP 2008086728A JP 2008086728 A JP2008086728 A JP 2008086728A JP 4993378 B2 JP4993378 B2 JP 4993378B2
- Authority
- JP
- Japan
- Prior art keywords
- rubber
- vulcanization accelerator
- rubber composition
- vulcanization
- tire
- 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 - Fee Related
Links
- 238000004073 vulcanization Methods 0.000 title claims description 55
- 229920001971 elastomer Polymers 0.000 title claims description 49
- 239000005060 rubber Substances 0.000 title claims description 49
- 239000000203 mixture Substances 0.000 title claims description 27
- 239000003795 chemical substances by application Substances 0.000 claims description 15
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims description 13
- YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 claims description 9
- 125000001424 substituent group Chemical group 0.000 claims description 9
- 239000011593 sulfur Substances 0.000 claims description 7
- 229910052717 sulfur Inorganic materials 0.000 claims description 7
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 244000043261 Hevea brasiliensis Species 0.000 claims description 4
- 229920003052 natural elastomer Polymers 0.000 claims description 4
- 229920001194 natural rubber Polymers 0.000 claims description 4
- 229920003244 diene elastomer Polymers 0.000 claims description 3
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 2
- -1 isooctyl Chemical group 0.000 description 18
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical group C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- 150000001412 amines Chemical class 0.000 description 10
- 150000002430 hydrocarbons Chemical group 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- 238000004898 kneading Methods 0.000 description 7
- 125000000217 alkyl group Chemical group 0.000 description 6
- 230000000694 effects Effects 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 238000001125 extrusion Methods 0.000 description 4
- 239000011737 fluorine Substances 0.000 description 4
- 229910052731 fluorine Inorganic materials 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 125000002347 octyl 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])[H] 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Substances CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- GPNLWUFFWOYKLP-UHFFFAOYSA-N s-(1,3-benzothiazol-2-yl)thiohydroxylamine Chemical class C1=CC=C2SC(SN)=NC2=C1 GPNLWUFFWOYKLP-UHFFFAOYSA-N 0.000 description 3
- 125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 description 3
- MACMAADVRVVHBD-VMPITWQZSA-N (e)-1-(2,4-dihydroxyphenyl)-3-(2-hydroxyphenyl)prop-2-en-1-one Chemical compound OC1=CC(O)=CC=C1C(=O)\C=C\C1=CC=CC=C1O MACMAADVRVVHBD-VMPITWQZSA-N 0.000 description 2
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 229920000459 Nitrile rubber Polymers 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 230000001133 acceleration Effects 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 2
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 2
- 229920003193 cis-1,4-polybutadiene polymer Polymers 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000006038 hexenyl group Chemical group 0.000 description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- DEQZTKGFXNUBJL-UHFFFAOYSA-N n-(1,3-benzothiazol-2-ylsulfanyl)cyclohexanamine Chemical compound C1CCCCC1NSC1=NC2=CC=CC=C2S1 DEQZTKGFXNUBJL-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 229920003048 styrene butadiene rubber Polymers 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 0 *C=CCNC1=Nc2ccccc2*1 Chemical compound *C=CCNC1=Nc2ccccc2*1 0.000 description 1
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Chemical group CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- 229920000181 Ethylene propylene rubber Polymers 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 239000006087 Silane Coupling Agent Substances 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 229920006311 Urethane elastomer Polymers 0.000 description 1
- 229920000800 acrylic rubber Polymers 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 230000003712 anti-aging effect Effects 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229920005549 butyl rubber Polymers 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 229920003211 cis-1,4-polyisoprene Polymers 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 239000007822 coupling agent Substances 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 125000002704 decyl group Chemical group [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])* 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- 125000003438 dodecyl group Chemical group [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])* 0.000 description 1
- 238000007720 emulsion polymerization reaction Methods 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 239000004088 foaming agent Substances 0.000 description 1
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229920005555 halobutyl Polymers 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 229920002681 hypalon Polymers 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000011256 inorganic filler Substances 0.000 description 1
- 229910003475 inorganic filler Inorganic materials 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000002960 margaryl 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])[H] 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 125000001421 myristyl 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])[H] 0.000 description 1
- CMAUJSNXENPPOF-UHFFFAOYSA-N n-(1,3-benzothiazol-2-ylsulfanyl)-n-cyclohexylcyclohexanamine Chemical compound C1CCCCC1N(C1CCCCC1)SC1=NC2=CC=CC=C2S1 CMAUJSNXENPPOF-UHFFFAOYSA-N 0.000 description 1
- 125000001400 nonyl 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])[H] 0.000 description 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 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
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 125000000913 palmityl 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])[H] 0.000 description 1
- 125000002958 pentadecyl 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])[H] 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920001084 poly(chloroprene) Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000005077 polysulfide Substances 0.000 description 1
- 229920001021 polysulfide Polymers 0.000 description 1
- 150000008117 polysulfides Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000013040 rubber vulcanization Methods 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
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000008117 stearic acid Substances 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
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229920003051 synthetic elastomer Polymers 0.000 description 1
- 239000005061 synthetic rubber Substances 0.000 description 1
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1
- 229960002447 thiram Drugs 0.000 description 1
- 125000002889 tridecyl 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])[H] 0.000 description 1
- 125000002948 undecyl 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])[H] 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
-
- Y02T10/862—
Landscapes
- Tires In General (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Description
(一般式(1)中、R1およびR2は、各々独立に、水素原子、または置換基を有してもよい炭素数1〜8の炭化水素基を表し、R3は水素原子、置換基を有してもよい炭素数1〜18の炭化水素基または置換基を有してもよい炭素数6〜18の芳香族基を表す)で表される2―メルカプトベンゾチアゾールを含有することを特徴とするものである。
本発明の加硫促進剤は、下記一般式(1)、
(一般式(1)中、R1およびR2は、各々独立に、水素原子、または置換基を有してもよい炭素数1〜8の炭化水素基を表し、R3は水素原子、置換基を有してもよい炭素数1〜18の炭化水素基または置換基を有してもよい炭素数6〜18の芳香族基を表す)で表される2―メルカプトベンゾチアゾールを含有するものである。かかる加硫促進剤は、ベンゾチアゾールスルフェンアミドのアミン部位がCH2CHCHR3になっていることによりアミンの発生がなくなり、職場環境を改善することができる。また、この加硫促進剤は優れた加硫性能を有する。
で表されるように、上記一般式(1)中のR1およびR2が水素原子であり、かつR3が水素原子であることが所望の効果を得る上で好ましい。この加硫促進剤は、ベンゾチアゾールスルフェンアミドのアミン部位がアリル基になっていることによりアミンの発生がなくなり、職場環境をより改善することができる。また、この加硫促進剤は優れた加硫性能を有する。
(加硫促進剤Aの合成)
窒素置換した200ml容量の四径フラスコに、2―メルカプトベンゾチアゾールナトリウム塩18.9g(0.1mol)とトルエン100mlを加えた。攪拌しながら5〜7℃で臭化アリル12.1g(0.1mol)を20分かけて滴下し、さらに同温で1時間攪拌を続けた。反応後、反応液を水洗し芒硝で脱水し、溶媒を留去してピンク色の液体を得た。
4.02 {d, 2H, ―S―CH2―CH=CHH}
5.23 {d, 1H, ―S―CH2―CH=CH2}
5.41 {d, 1H, ―S―CH2―CH=CH2}
6.05 {d, 1H, ―S―CH2―CH=CH2}
7.31 {t, 1H, ベンゼン環}
7.44 {t, 1H, ベンゼン環}
7.76 {d, 1H, ベンゼン環}
7.90 {d, 1H, ベンゼン環}
下記表1に示す配合内容の各ゴム組成物を、ラボプラストミルを使用して混練り配合し、未加硫のゴム組成物を得た。
各未加硫のゴム組成物について、キュラスト試験をオリエンティック製キュラストメーターで行い145℃で測定した。T10は加硫反応によるトルクの上昇が全体の10%に達した時間(分)、T90は加硫反応によるトルクの上昇が全体の90%に達した時間(分)、MHはトルクの最大値(N・m)を表す。結果を表1に併記する。
Claims (7)
- 前記一般式(1)中のR1およびR2が水素原子であり、かつR3が水素原子である請求項1記載の加硫促進剤。
- ゴム成分に対して、請求項1または2記載の加硫促進剤と加硫剤とを配合してなることを特徴とするゴム組成物。
- 前記加硫剤が、硫黄である請求項3記載のゴム組成物。
- 前記ゴム成分が、ジエン系ゴム成分または天然ゴムである請求項3または4記載のゴム組成物。
- 前記ゴム成分100質量部に対して、前記加硫促進剤を0.1〜10質量部配合してなる請求項3〜5のうちいずれか一項に記載のゴム組成物。
- 請求項3〜6のうちいずれか一項に記載のゴム組成物を用いたことを特徴とするタイヤ。
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2008086728A JP4993378B2 (ja) | 2008-03-28 | 2008-03-28 | 加硫促進剤、ゴム組成物およびそれを用いたタイヤ |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2008086728A JP4993378B2 (ja) | 2008-03-28 | 2008-03-28 | 加硫促進剤、ゴム組成物およびそれを用いたタイヤ |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2009235343A JP2009235343A (ja) | 2009-10-15 |
JP4993378B2 true JP4993378B2 (ja) | 2012-08-08 |
Family
ID=41249699
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2008086728A Expired - Fee Related JP4993378B2 (ja) | 2008-03-28 | 2008-03-28 | 加硫促進剤、ゴム組成物およびそれを用いたタイヤ |
Country Status (1)
Country | Link |
---|---|
JP (1) | JP4993378B2 (ja) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2016084569A1 (ja) * | 2014-11-28 | 2016-06-02 | 住友ゴム工業株式会社 | タイヤ外層用ゴム組成物及び空気入りタイヤ |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH11349557A (ja) * | 1998-04-10 | 1999-12-21 | Ube Ind Ltd | ジフルオロアルケン誘導体、その製法及び農園芸用の有害生物防除剤 |
JP4295385B2 (ja) * | 1999-04-08 | 2009-07-15 | 株式会社ブリヂストン | 空気入りタイヤ |
-
2008
- 2008-03-28 JP JP2008086728A patent/JP4993378B2/ja not_active Expired - Fee Related
Also Published As
Publication number | Publication date |
---|---|
JP2009235343A (ja) | 2009-10-15 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
EP2530076B1 (en) | Fused heterocyclic compound and composition | |
JP5269504B2 (ja) | ゴム組成物の製造方法 | |
JP5269503B2 (ja) | ゴム組成物の製造方法 | |
JP4598148B2 (ja) | スルフェンアミド、このスルフェンアミドを含むゴム用加硫促進剤およびその製造方法 | |
JP5347353B2 (ja) | シリカ配合ジエン系ゴム組成物の製造法 | |
JP2011089031A (ja) | ゴム組成物 | |
JP2011052089A (ja) | タイヤ用ゴム組成物およびそれを用いた空気入りタイヤ | |
KR20170019354A (ko) | 알킬리덴아미노구아니딘 및 그 염, 변성용 조성물, 타이어용 변성 고무, 타이어용 고무 조성물 그리고 타이어 | |
JP2014210870A (ja) | タイヤトレッド用ゴム組成物およびそれを用いた空気入りタイヤ | |
JP2009269977A (ja) | 加硫促進剤、ゴム組成物およびそれを用いたタイヤ | |
JP4993378B2 (ja) | 加硫促進剤、ゴム組成物およびそれを用いたタイヤ | |
JP2009235348A (ja) | 加硫促進剤、ゴム組成物およびそれを用いたタイヤ | |
JP2011052098A (ja) | ゴム組成物およびそれを用いた空気入りタイヤ | |
JP2009235349A (ja) | 加硫促進剤、ゴム組成物およびそれを用いたタイヤ | |
JP2009235344A (ja) | 加硫促進剤、ゴム組成物およびそれを用いたタイヤ | |
JP6331544B2 (ja) | ゴム組成物、その製造方法およびそれを用いた空気入りタイヤ | |
JP4994282B2 (ja) | 加硫促進剤、ゴム組成物およびそれを用いたタイヤ | |
JP2010059290A (ja) | 加硫促進剤、ゴム組成物およびそれを用いたタイヤ | |
JP2014080535A (ja) | ゴム・カーボンブラック用カップリング剤及びタイヤ用ゴム組成物 | |
JP2009235347A (ja) | 加硫促進剤、ゴム組成物およびそれを用いたタイヤ | |
JP2009235345A (ja) | 加硫促進剤、ゴム組成物およびそれを用いたタイヤ | |
JP6125323B2 (ja) | ゴム組成物及び空気入りタイヤ | |
JP5485841B2 (ja) | タイヤ用ゴム組成物及び空気入りタイヤ | |
JP5594352B2 (ja) | 分子中に二重結合を有するゴム組成物 | |
JP5730686B2 (ja) | 変性ジエン系ゴムの製造方法 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20110316 |
|
A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20120419 |
|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20120427 |
|
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20120427 |
|
FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20150518 Year of fee payment: 3 |
|
R150 | Certificate of patent or registration of utility model |
Free format text: JAPANESE INTERMEDIATE CODE: R150 Ref document number: 4993378 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
LAPS | Cancellation because of no payment of annual fees |