JP2017503910A - アミン基を含む陰イオン末端を有する陰イオン重合開始剤、これを用いた変性共役ジエン系共重合体の製造方法、およびこれにより製造した変性共役ジエン系共重合体を含むゴム組成物 - Google Patents
アミン基を含む陰イオン末端を有する陰イオン重合開始剤、これを用いた変性共役ジエン系共重合体の製造方法、およびこれにより製造した変性共役ジエン系共重合体を含むゴム組成物 Download PDFInfo
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- JP2017503910A JP2017503910A JP2016566594A JP2016566594A JP2017503910A JP 2017503910 A JP2017503910 A JP 2017503910A JP 2016566594 A JP2016566594 A JP 2016566594A JP 2016566594 A JP2016566594 A JP 2016566594A JP 2017503910 A JP2017503910 A JP 2017503910A
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- Prior art keywords
- conjugated diene
- carbon atoms
- diene polymer
- modified conjugated
- chemical formula
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- -1 cyclic amine Chemical class 0.000 description 7
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- GTEXIOINCJRBIO-UHFFFAOYSA-N 2-[2-(dimethylamino)ethoxy]-n,n-dimethylethanamine Chemical compound CN(C)CCOCCN(C)C GTEXIOINCJRBIO-UHFFFAOYSA-N 0.000 description 1
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- ZFFBIQMNKOJDJE-UHFFFAOYSA-N 2-bromo-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(Br)C(=O)C1=CC=CC=C1 ZFFBIQMNKOJDJE-UHFFFAOYSA-N 0.000 description 1
- CSBDTEMAXHVRBB-UHFFFAOYSA-N 2-ethoxy-n,n-dimethylethanamine Chemical compound CCOCCN(C)C CSBDTEMAXHVRBB-UHFFFAOYSA-N 0.000 description 1
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- BMGCAVDKTZGWHD-UHFFFAOYSA-N CN(CC(CN(C)C)C[Si](OC)(OC)OC)C Chemical compound CN(CC(CN(C)C)C[Si](OC)(OC)OC)C BMGCAVDKTZGWHD-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
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- 244000043261 Hevea brasiliensis Species 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound 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 description 1
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 1
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- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 239000004902 Softening Agent Substances 0.000 description 1
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- 125000000129 anionic group Chemical group 0.000 description 1
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- 150000001768 cations Chemical class 0.000 description 1
- 238000004581 coalescence Methods 0.000 description 1
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- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- 229920003244 diene elastomer Polymers 0.000 description 1
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 1
- POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- BLHLJVCOVBYQQS-UHFFFAOYSA-N ethyllithium Chemical compound [Li]CC BLHLJVCOVBYQQS-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
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- 238000010438 heat treatment Methods 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 239000010954 inorganic particle Substances 0.000 description 1
- AFRJJFRNGGLMDW-UHFFFAOYSA-N lithium amide Chemical compound [Li+].[NH2-] AFRJJFRNGGLMDW-UHFFFAOYSA-N 0.000 description 1
- UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 1
- SZAVVKVUMPLRRS-UHFFFAOYSA-N lithium;propane Chemical compound [Li+].C[CH-]C SZAVVKVUMPLRRS-UHFFFAOYSA-N 0.000 description 1
- 238000010551 living anionic polymerization reaction Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 229920003052 natural elastomer Polymers 0.000 description 1
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- 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
- NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 description 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- PMJHHCWVYXUKFD-UHFFFAOYSA-N piperylene Natural products CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 229920005604 random copolymer 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
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 239000010421 standard material Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 238000009864 tensile test Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- 238000004073 vulcanization Methods 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 235000014692 zinc oxide Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/42—Introducing metal atoms or metal-containing groups
-
- 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
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/06—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with radicals, containing only hydrogen and carbon atoms, attached to ring carbon atoms
-
- 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
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- C—CHEMISTRY; METALLURGY
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Abstract
Description
フラスコに、ヘキサン20gに3−(2−ピロリジノ−1−メチルエチル)−アルファ−メチルスチレンを8.5g、1.6Mブチルリチウム18gを反応器に入れた後、1時間撹拌して、変性開始剤として3−(2−ピロリジノ−1−メチルエチル)−アルファ−メチルスチレンリチウムを用意した。
変性剤としてビス(3−トリエトキシメチルシリルプロピル)−N−メチルアミンの代わりにN1,N1,N3,N3−テトラメチル−2−((トリメトキシシリル)メチル)プロパン−1,3−ジアミンを用いたことを除いては、実施例1と同様にして変性共役ジエン系重合体を製造した。
変性剤としてビス(3−トリエトキシメチルシリルプロピル)−N−メチルアミンの代わりにN,N−ビス(トリエトキシシリルプロピル)アミノプロピル−1−イミダゾール1gを用いたことを除いては、実施例1と同様にして変性共役ジエン系重合体を製造した。
開始剤としてブチルリチウムを用いたことを除いては、実施例1と同様にして変性共役ジエン系重合体を製造した。
b:ビス(3−トリエトキシメチルシリルプロピル)−N−メチルアミン
c:N1,N1,N3,N3−テトラメチル−2−(トリメトキシシリル)メチル)プロパン−1,3−ジアミン
d:N,N−ビス(トリエトキシシリルプロピル)アミノプロピル−1−イミダゾール
前記表1に示した試料のうち、A、BおよびCを原料ゴムとして、下記表2に示した配合条件で配合して、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、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。このために、Instron社のUniversal Test Machine4204引張試験機を用いており、室温で50cm/minの引張速度で測定して、引張強度、Modulus、伸び率などの測定値を得た。
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(−60〜60℃)で変形を変化させて、Tanδを測定した。ペイン効果は、変形0.28%〜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、シリカ等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。
Claims (13)
- 下記化学式1〜化学式3のうちのいずれか1つで表される変性共役ジエン系重合体:
- a)下記化学式4で表される化合物の存在下、炭化水素溶媒中で共役ジエン系単量体、または共役ジエン系単量体と芳香族ビニル系単量体とを重合させて、アルカリ金属末端を有する活性重合体を形成するステップと、
b)前記アルカリ金属末端を有する活性重合体に、下記化学式5、化学式6、または化学式7で表される化合物を投入して変性させるステップとを含む変性共役ジエン系重合体の製造方法:
- 前記化学式4で表される化合物は、前記単量体計100gを基準として、0.01〜10mmol使用されることを特徴とする請求項2に記載の変性共役ジエン系重合体の製造方法。
- 前記化学式4で表される化合物と、前記化学式5、化学式6、または化学式7で表される化合物とのモル比は、1:0.1〜1:10であることを特徴とする請求項2に記載の変性共役ジエン系重合体の製造方法。
- 前記a)ステップにおいて、極性添加剤がさらに投入されることを特徴とする請求項2に記載の変性共役ジエン系重合体の製造方法。
- 前記極性添加剤は、前記化学式4で表される化合物計1mmolを基準として、0.001〜10g投入されることを特徴とする請求項5に記載の変性共役ジエン系重合体の製造方法。
- 前記変性共役ジエン系重合体は、1,000〜2,000,000g/molの数平均分子量(Mn)を有することを特徴とする請求項2に記載の変性共役ジエン系重合体の製造方法。
- 前記変性共役ジエン系重合体は、共役ジエン系単量体と芳香族ビニル系単量体とを合わせた計100重量%を基準として、芳香族ビニル系単量体が0.0001〜50重量%含まれていることを特徴とする請求項2に記載の変性共役ジエン系重合体の製造方法。
- 請求項1に記載の変性共役ジエン系重合体10〜100重量部、前記変性共役ジエン系重合体100重量部に対して、無機充填剤0.1〜200重量部を含む変性共役ジエン系重合体ゴム組成物。
- 前記無機充填剤は、シリカ系充填剤、カーボンブラック、およびこれらの混合物からなる群より選択された1種以上であることを特徴とする請求項11に記載の変性共役ジエン系重合体ゴム組成物。
- 請求項11に記載の変性共役ジエン系重合体ゴム組成物を含むタイヤまたはタイヤトレッド。
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JP2020530060A (ja) * | 2017-12-05 | 2020-10-15 | エルジー・ケム・リミテッド | 変性共役ジエン系重合体およびそれを含むゴム組成物 |
JP2021505712A (ja) * | 2017-12-05 | 2021-02-18 | エルジー・ケム・リミテッド | 変性共役ジエン系重合体及びこれを含むゴム組成物 |
US11299559B2 (en) | 2017-12-05 | 2022-04-12 | Lg Chem, Ltd. | Modified conjugated diene-based polymer and rubber composition including the same |
JP7462557B2 (ja) | 2017-12-05 | 2024-04-05 | エルジー・ケム・リミテッド | 変性共役ジエン系重合体及びこれを含むゴム組成物 |
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CN106029708A (zh) | 2016-10-12 |
KR20160065733A (ko) | 2016-06-09 |
EP3091040B1 (en) | 2018-04-18 |
EP3091040A1 (en) | 2016-11-09 |
KR101776391B1 (ko) | 2017-09-07 |
EP3091040A4 (en) | 2016-11-30 |
US9718899B2 (en) | 2017-08-01 |
JP6273044B2 (ja) | 2018-01-31 |
CN106029708B (zh) | 2019-05-03 |
US20160347877A1 (en) | 2016-12-01 |
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