JP6500029B2 - 分散剤を含む共役ジエン系重合体ゴム組成物 - Google Patents
分散剤を含む共役ジエン系重合体ゴム組成物 Download PDFInfo
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- JP6500029B2 JP6500029B2 JP2016553530A JP2016553530A JP6500029B2 JP 6500029 B2 JP6500029 B2 JP 6500029B2 JP 2016553530 A JP2016553530 A JP 2016553530A JP 2016553530 A JP2016553530 A JP 2016553530A JP 6500029 B2 JP6500029 B2 JP 6500029B2
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- 150000001993 dienes Chemical class 0.000 title claims description 74
- 229920000642 polymer Polymers 0.000 title claims description 66
- 239000000203 mixture Substances 0.000 title claims description 36
- 229920001971 elastomer Polymers 0.000 title claims description 34
- 239000005060 rubber Substances 0.000 title claims description 34
- 239000002270 dispersing agent Substances 0.000 title description 3
- 239000000126 substance Substances 0.000 claims description 46
- 125000004432 carbon atom Chemical group C* 0.000 claims description 26
- 150000001875 compounds Chemical class 0.000 claims description 21
- 125000001931 aliphatic group Chemical group 0.000 claims description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- -1 R 23 Chemical compound 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- 239000000178 monomer Substances 0.000 description 37
- 229920002554 vinyl polymer Polymers 0.000 description 18
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 12
- 238000005096 rolling process Methods 0.000 description 9
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 6
- 238000006116 polymerization reaction Methods 0.000 description 6
- SDJHPPZKZZWAKF-UHFFFAOYSA-N 2,3-dimethylbuta-1,3-diene Chemical compound CC(=C)C(C)=C SDJHPPZKZZWAKF-UHFFFAOYSA-N 0.000 description 4
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 4
- CUFBDUDYFHCIOH-UHFFFAOYSA-N 3-(11-methyldodecoxy)propan-1-amine Chemical compound CC(C)CCCCCCCCCCOCCCN CUFBDUDYFHCIOH-UHFFFAOYSA-N 0.000 description 4
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 4
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000000446 fuel Substances 0.000 description 4
- 239000011256 inorganic filler Substances 0.000 description 4
- 229910003475 inorganic filler Inorganic materials 0.000 description 4
- 238000004898 kneading Methods 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 230000000704 physical effect Effects 0.000 description 4
- 229920003048 styrene butadiene rubber Polymers 0.000 description 4
- 239000004636 vulcanized rubber Substances 0.000 description 4
- BITAPBDLHJQAID-MDZDMXLPSA-N 2-[2-hydroxyethyl-[(e)-octadec-9-enyl]amino]ethanol Chemical compound CCCCCCCC\C=C\CCCCCCCCN(CCO)CCO BITAPBDLHJQAID-MDZDMXLPSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 239000005062 Polybutadiene Substances 0.000 description 3
- 238000005299 abrasion Methods 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 239000003963 antioxidant agent Substances 0.000 description 3
- 230000003078 antioxidant effect Effects 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 239000000945 filler Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 229920002857 polybutadiene Polymers 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical group C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 description 2
- VDNSZPNSUQRUMS-UHFFFAOYSA-N 1-cyclohexyl-4-ethenylbenzene Chemical compound C1=CC(C=C)=CC=C1C1CCCCC1 VDNSZPNSUQRUMS-UHFFFAOYSA-N 0.000 description 2
- JZHGRUMIRATHIU-UHFFFAOYSA-N 1-ethenyl-3-methylbenzene Chemical compound CC1=CC=CC(C=C)=C1 JZHGRUMIRATHIU-UHFFFAOYSA-N 0.000 description 2
- VVTGQMLRTKFKAM-UHFFFAOYSA-N 1-ethenyl-4-propylbenzene Chemical compound CCCC1=CC=C(C=C)C=C1 VVTGQMLRTKFKAM-UHFFFAOYSA-N 0.000 description 2
- OIEANVCCDIRIDJ-UHFFFAOYSA-N 1-ethenyl-5-hexylnaphthalene Chemical compound C1=CC=C2C(CCCCCC)=CC=CC2=C1C=C OIEANVCCDIRIDJ-UHFFFAOYSA-N 0.000 description 2
- IGGDKDTUCAWDAN-UHFFFAOYSA-N 1-vinylnaphthalene Chemical compound C1=CC=C2C(C=C)=CC=CC2=C1 IGGDKDTUCAWDAN-UHFFFAOYSA-N 0.000 description 2
- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 description 2
- UGWOAPBVIGCNOV-UHFFFAOYSA-N 5-ethenyldec-5-ene Chemical compound CCCCC=C(C=C)CCCC UGWOAPBVIGCNOV-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- 239000002174 Styrene-butadiene Substances 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 235000006708 antioxidants Nutrition 0.000 description 2
- 229920001519 homopolymer Polymers 0.000 description 2
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- PMJHHCWVYXUKFD-UHFFFAOYSA-N piperylene Natural products CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 238000004073 vulcanization Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- PEBXLTUWFWEWGV-UHFFFAOYSA-N 1-methyl-2-(2-phenylethenyl)benzene Chemical compound CC1=CC=CC=C1C=CC1=CC=CC=C1 PEBXLTUWFWEWGV-UHFFFAOYSA-N 0.000 description 1
- FZLHAQMQWDDWFI-UHFFFAOYSA-N 2-[2-(oxolan-2-yl)propan-2-yl]oxolane Chemical compound C1CCOC1C(C)(C)C1CCCO1 FZLHAQMQWDDWFI-UHFFFAOYSA-N 0.000 description 1
- 0 CN(*)*N(*)C(*)N* Chemical compound CN(*)*N(*)C(*)N* 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 244000043261 Hevea brasiliensis Species 0.000 description 1
- 239000006087 Silane Coupling Agent Substances 0.000 description 1
- 239000004902 Softening Agent Substances 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001339 alkali metal compounds Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 238000010923 batch production Methods 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- 238000004925 denaturation Methods 0.000 description 1
- 230000036425 denaturation Effects 0.000 description 1
- 229920003244 diene elastomer Polymers 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
- 229920003052 natural elastomer Polymers 0.000 description 1
- 229920001194 natural rubber Polymers 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
- 235000019198 oils Nutrition 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000012925 reference material Substances 0.000 description 1
- 239000012744 reinforcing agent Substances 0.000 description 1
- 229930000044 secondary metabolite Natural products 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 239000010421 standard material Substances 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 238000005987 sulfurization reaction Methods 0.000 description 1
- 238000009864 tensile test Methods 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 235000014692 zinc oxide Nutrition 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/17—Amines; Quaternary ammonium compounds
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B60—VEHICLES IN GENERAL
- B60C—VEHICLE TYRES; TYRE INFLATION; TYRE CHANGING; CONNECTING VALVES TO INFLATABLE ELASTIC BODIES IN GENERAL; DEVICES OR ARRANGEMENTS RELATED TO TYRES
- B60C1/00—Tyres characterised by the chemical composition or the physical arrangement or mixture of the composition
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B60—VEHICLES IN GENERAL
- B60C—VEHICLE TYRES; TYRE INFLATION; TYRE CHANGING; CONNECTING VALVES TO INFLATABLE ELASTIC BODIES IN GENERAL; DEVICES OR ARRANGEMENTS RELATED TO TYRES
- B60C1/00—Tyres characterised by the chemical composition or the physical arrangement or mixture of the composition
- B60C1/0016—Compositions of the tread
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08C—TREATMENT OR CHEMICAL MODIFICATION OF RUBBERS
- C08C19/00—Chemical modification of rubber
- C08C19/22—Incorporating nitrogen atoms into the molecule
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08C—TREATMENT OR CHEMICAL MODIFICATION OF RUBBERS
- C08C19/00—Chemical modification of rubber
- C08C19/25—Incorporating silicon atoms into the molecule
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08C—TREATMENT OR CHEMICAL MODIFICATION OF RUBBERS
- C08C19/00—Chemical modification of rubber
- C08C19/30—Addition of a reagent which reacts with a hetero atom or a group containing hetero atoms of the macromolecule
- C08C19/42—Addition of a reagent which reacts with a hetero atom or a group containing hetero atoms of the macromolecule reacting with metals or metal-containing groups
- C08C19/44—Addition of a reagent which reacts with a hetero atom or a group containing hetero atoms of the macromolecule reacting with metals or metal-containing groups of polymers containing metal atoms exclusively at one or both ends of the skeleton
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L15/00—Compositions of rubber derivatives
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L9/00—Compositions of homopolymers or copolymers of conjugated diene hydrocarbons
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2205/00—Polymer mixtures characterised by other features
- C08L2205/02—Polymer mixtures characterised by other features containing two or more polymers of the same C08L -group
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2205/00—Polymer mixtures characterised by other features
- C08L2205/03—Polymer mixtures characterised by other features containing three or more polymers in a blend
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Mechanical Engineering (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Tires In General (AREA)
Description
3つの反応器を用意するが、3つの反応器のうち、1基目および2基目の反応器を重合反応器とし、3基目の反応器を変性反応器とした。
ビス−(2−ヒドロキシエチル)イソトリデシルオキシプロピルアミン1.5phrを追加したことを除いては、実施例1と同様の方法で共役ジエン系重合体を製造した。
オレイルビス(2−ヒドロキシエチル)アミン1phrを追加したことを除いては、実施例1と同様の方法で共役ジエン系重合体を製造した。
オレイルビス(2−ヒドロキシエチル)アミン1.5phrを追加したことを除いては、実施例1と同様の方法で共役ジエン系重合体を製造した。
分散剤を使用しないことを除いては、実施例1と同様の方法で共役ジエン系重合体を製造した。
c:オレイルビス(2−ヒドロキシエチル)アミン
製造例1〜4、および比較製造例1:ゴム組成物の製造
前記表1に示した試料のうち、A、B、C、DおよびEを原料ゴムとし、下記表2に示した配合条件で配合して、製造例1〜4、および比較製造例1の共役ジエン系重合体ゴム組成物を製造した。
ASTM412の引張試験法によって、加硫ゴム試験片の切断時の引張強度および300%伸張時の引張応力(300%モジュラス)を測定した。
TA社の動的機械分析機を用いた。ねじれモードで、周波数10Hz、各測定温度(0〜60℃)で変形を変化させて、Tanδを測定した。ペイン効果は、変形0.2%〜40%での最小値と最大値との差で示した。ペイン効果が小さいほど、シリカなど充填剤の分散性が良い。低温0℃のTanδが高いほど、ウェット路面抵抗性に優れ、高温60℃のTanδが低いほど、ヒステリシス損失が少なく、タイヤの低転がり抵抗性、すなわち低燃費性に優れている。表3に加硫ゴムの物性を示した。
ゴムの転がり抵抗性(RR)と制動性(wet grip)は、DMTS(Dynamic mechanical thermal spectrometry;GABO、EPLEXOR500N)を用いて測定した。測定時の試験条件は、Frequency:10Hz、Strain(Static strain:3%、Dynamic strain:0.25%)、Temperature:−60〜70℃とした。この時、転がり抵抗性は、60℃で測定されたTanδ値の逆数を用い、制動性は、0℃で測定されたTanδ値を用いて、比較例1の値を100基準としてindex比較した。
Claims (6)
- ゴム成分としての変性共役ジエン系重合体;および化学式1または化学式2で表される化合物を含み、
前記変性共役ジエン系重合体は、下記化学式3で表される化合物であるゴム組成物。
前記化学式1において、R1は炭素数8〜24の脂肪族炭化水素基であり、R2は水素、または炭素数1〜3の脂肪族炭化水素基であり、nは1〜10の整数であり;
前記化学式2において、R1は炭素数8〜24の脂肪族炭化水素基であり、R2は水素、または炭素数1〜3の脂肪族炭化水素基であり、nは1〜10の整数である。
前記化学式3において、R1、R2およびR5はそれぞれ独立に炭素数1〜10のアルキレン基であり、R3、R4、R6およびR7はそれぞれ独立に炭素数1〜10のアルキル基であり、R8は水素、またはそれぞれ独立に炭素数1〜10のアルキル基であり、Pは共役ジエン系重合体鎖であり、aおよびcはそれぞれ独立に0、1または2であり、bおよびdはそれぞれ独立に1、2または3であり、a+bおよびc+dはそれぞれ独立に1、2または3であり、Aは
または
であり、R9、R10、R11およびR12はそれぞれ独立に水素、または炭素数1〜10のアルキル基であり、波線は窒素原子への結合を意味する。 - 前記変性共役ジエン系重合体は、数平均分子量が1,000〜2,000,000g/molであることを特徴とする請求項1に記載のゴム組成物。
- 請求項1〜5のいずれか一項に記載のゴム組成物を含むタイヤまたはタイヤトレッド。
Applications Claiming Priority (7)
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KR10-2014-0166286 | 2014-11-26 | ||
KR10-2014-0166675 | 2014-11-26 | ||
KR20140166675 | 2014-11-26 | ||
KR20140166286 | 2014-11-26 | ||
KR10-2015-0116530 | 2015-08-19 | ||
KR1020150116530A KR101687914B1 (ko) | 2014-11-26 | 2015-08-19 | 분산제를 포함하는 공역디엔계 중합체 고무 조성물 |
PCT/KR2015/011804 WO2016085143A1 (ko) | 2014-11-26 | 2015-11-04 | 분산제를 포함하는 공역디엔계 중합체 고무 조성물 |
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JP2017508841A JP2017508841A (ja) | 2017-03-30 |
JP6500029B2 true JP6500029B2 (ja) | 2019-04-10 |
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Country Status (5)
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US (1) | US10053552B2 (ja) |
EP (1) | EP3098260B1 (ja) |
JP (1) | JP6500029B2 (ja) |
KR (1) | KR101687914B1 (ja) |
CN (1) | CN106068301B (ja) |
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JP7387247B2 (ja) | 2016-12-07 | 2023-11-28 | 旭化成株式会社 | 変性共役ジエン系重合体、変性共役ジエン系重合体組成物、及びタイヤ |
JP7458373B2 (ja) | 2019-03-27 | 2024-03-29 | 株式会社Eneosマテリアル | 重合体組成物、架橋重合体、及びタイヤ |
CN116348313A (zh) | 2020-10-16 | 2023-06-27 | 株式会社引能仕材料 | 橡胶块及其制造方法、聚合物组合物、交联体及轮胎 |
KR20230140390A (ko) | 2022-03-29 | 2023-10-06 | 가부시키가이샤 에네오스 마테리아루 | 중합체 조성물 및 그의 제조 방법, 배합물, 가교체 그리고 타이어 |
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- 2015-11-04 CN CN201580011717.9A patent/CN106068301B/zh active Active
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KR101687914B1 (ko) | 2016-12-19 |
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EP3098260A4 (en) | 2017-05-31 |
KR20160063227A (ko) | 2016-06-03 |
EP3098260B1 (en) | 2018-02-28 |
CN106068301A (zh) | 2016-11-02 |
US10053552B2 (en) | 2018-08-21 |
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US20170009057A1 (en) | 2017-01-12 |
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