JP6239600B2 - ポリマーの製造方法、該ポリマーを含有するポリマー組成物及び物品 - Google Patents
ポリマーの製造方法、該ポリマーを含有するポリマー組成物及び物品 Download PDFInfo
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- JP6239600B2 JP6239600B2 JP2015516168A JP2015516168A JP6239600B2 JP 6239600 B2 JP6239600 B2 JP 6239600B2 JP 2015516168 A JP2015516168 A JP 2015516168A JP 2015516168 A JP2015516168 A JP 2015516168A JP 6239600 B2 JP6239600 B2 JP 6239600B2
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- 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
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- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
- 235000013539 calcium stearate Nutrition 0.000 description 1
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- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- LEKSIJZGSFETSJ-UHFFFAOYSA-N cyclohexane;lithium Chemical compound [Li]C1CCCCC1 LEKSIJZGSFETSJ-UHFFFAOYSA-N 0.000 description 1
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- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
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- CCZVEWRRAVASGL-UHFFFAOYSA-N lithium;2-methanidylpropane Chemical compound [Li+].CC(C)[CH2-] CCZVEWRRAVASGL-UHFFFAOYSA-N 0.000 description 1
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- 238000005259 measurement Methods 0.000 description 1
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- 125000003136 n-heptyl 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])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
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- IJJSYKQZFFGIEE-UHFFFAOYSA-N naphthalene;potassium Chemical compound [K].C1=CC=CC2=CC=CC=C21 IJJSYKQZFFGIEE-UHFFFAOYSA-N 0.000 description 1
- URXNVXOMQQCBHS-UHFFFAOYSA-N naphthalene;sodium Chemical compound [Na].C1=CC=CC2=CC=CC=C21 URXNVXOMQQCBHS-UHFFFAOYSA-N 0.000 description 1
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
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- NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 description 1
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- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- CNPZVMLYLJDMOV-UHFFFAOYSA-N potassium 2,2-dimethylheptan-3-olate Chemical compound C(C)(C)(C)C(CCCC)O[K] CNPZVMLYLJDMOV-UHFFFAOYSA-N 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 229920005604 random copolymer Polymers 0.000 description 1
- 239000000376 reactant 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
- 239000003707 silyl modified polymer Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium 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
- 229920000468 styrene butadiene styrene block copolymer Polymers 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- UEUXEKPTXMALOB-UHFFFAOYSA-J tetrasodium;2-[2-[bis(carboxylatomethyl)amino]ethyl-(carboxylatomethyl)amino]acetate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]C(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CC([O-])=O UEUXEKPTXMALOB-UHFFFAOYSA-J 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
-
- 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
- C08C—TREATMENT OR CHEMICAL MODIFICATION OF RUBBERS
- C08C2/00—Treatment of rubber solutions
- C08C2/06—Wining of rubber from solutions
-
- 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
- C08F236/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds
- C08F236/02—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds
- C08F236/04—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds conjugated
- C08F236/10—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds conjugated with vinyl-aromatic monomers
-
- 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
- C08F36/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds
- C08F36/02—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds
- C08F36/04—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds conjugated
- C08F36/06—Butadiene
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J3/00—Processes of treating or compounding macromolecular substances
- C08J3/12—Powdering or granulating
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J3/00—Processes of treating or compounding macromolecular substances
- C08J3/20—Compounding polymers with additives, e.g. colouring
- C08J3/205—Compounding polymers with additives, e.g. colouring in the presence of a continuous liquid phase
- C08J3/21—Compounding polymers with additives, e.g. colouring in the presence of a continuous liquid phase the polymer being premixed with a liquid phase
-
- 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
- C08K5/54—Silicon-containing compounds
- C08K5/541—Silicon-containing compounds containing oxygen
- C08K5/5415—Silicon-containing compounds containing oxygen containing at least one Si—O bond
- C08K5/5419—Silicon-containing compounds containing oxygen containing at least one Si—O bond containing at least one Si—C bond
-
- 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
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2500/00—Characteristics or properties of obtained polyolefins; Use thereof
- C08F2500/21—Rubbery or elastomeric properties
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2309/00—Characterised by the use of homopolymers or copolymers of conjugated diene hydrocarbons
- C08J2309/06—Copolymers with styrene
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2203/00—Applications
Description
本願は、「Method of Making Stabilized Polymers, Polymer Compositions, and Articles Containing Such Polymers」を名称とする米国特許出願番号第(P40761)号、「Method of Making Iminosilane Stabilized Polymers, Polymer Compositions, and Articles Containing Such Polymers」を名称とする同第(P40762)号、及び「Method of Making Polymers, Polymer Compositions, and Articles Containing Such Polymers」を名称とする同第(P41148)号の1件又は複数件に開示される主題に関係し得る。上記出願の各々は、本願に記載の日付の同日付で出願され、本願と共通の法人に譲渡され、本願と共通の発明者を共有する。更に、上記出願の各々及びいずれもが、その全てにおいて、全ての目的に対して、参照により本明細書に組み入れられる。
(式中、Xは存在しても存在しなくてもよく、酸素又はイオウなどの結合原子、化学結合、又は結合基を表し、R1はC1〜C18アルキル基、窒素又は酸素などのヘテロ原子を含有するC1〜C18アルキル基、C4〜C8環状アルキル、又はC6〜C18芳香族基であり、R2及びR3は同一又は異なることができ、−OR1、C1〜C18アルキル基、C4〜C8環状アルキル基、又はC6〜C18芳香族基からなる群より選択される。)で表されるシラン末端ポリマーである。好ましい官能化剤は、上記式中、C2であってエトキシ基を形成するR1、OR1と同一の基であるR2、3−(1,3−ジメチルブチリデン)アミノプロピル基であるR3によって表される、3−(1,3−ジメチルブチリデン)アミノプロピルトリエトキシシラン(DMBAPTES)であろう。該官能化剤は、上記の式による表記に加え、更なるポリマー鎖がR2及び/又はOR1の位置を通じて結合することも、同様に可能である。
表1に示す試料は、70°F(21℃)において105ポンド(47.6キログラム)のヘキサン容量を有する20ガロン(75.7リットル)の撹拌反応器2基を用いた連続式重合運転由来のものである。ヘキサン中20重量%の総モノマー濃度、モノマーの37重量%がスチレンからなり、モノマーの63重量%が1,3−ブタジエンからなり、総流速が315ポンド/hr(142.9kg/hr)、その結果の滞留時間が20分において、原料流を連続的に加えた。開始剤(500グラムの3重量%n−ブチルリチウム)を、1,2−ブタジエン/ブチルリチウムのモル比0.33、2,2’−ジ(テトラヒドロフリル)プロパンのブチルリチウムに対するモル比0.37で、反応器底部に加えた。第1の反応器の2/3温度(反応器側面上、底部から概略2/3の容積となる位置における温度測定)を221°F(105℃)に制御した。第1の20ガロン(75.7リットル)反応器の後に、ブチルリチウムに対するモル比が0.5のDMBAPTSを加え、第2の20(75.7リットル)ガロン反応器において連続的に撹拌した。ポリマー試料を配合槽中に2時間収取し、次にBHT(ポリマー重量を基準として1%)及びクエンチのためのイソプロパノールを配合槽に加えた。2ドラムのポリマーを後処理に供するために抜き出した。1ドラムを、各18ポンド(8.16キログラム)のポリマーセメントを有する5ガロン(18.9リットル)の試料6つに分割した。次に、添加した安定剤の総量を示す表1に示される通りに試料を処理した。数値は、重合に用いたブチルリチウムに対する安定剤のモル比である。
Claims (15)
- 炭化水素溶媒中、開始剤の存在下で共役ジオレフィンを反応させてポリマーを生成させることと、
前記ポリマーに、アルコキシシラン末端官能化基を結合させることと、
トリアルキルシラノール、トリアリールシラノール、又はジアリールシランジオールである安定剤を前記ポリマーに添加することと、
前記ポリマーを脱溶媒化することと、
を含み、安定したムーニー粘度を有するポリマーをもたらすポリマーの製造方法。 - 前記安定剤がトリアリールシラノールである、請求項1に記載の方法。
- 前記安定剤がトリフェニルシラノールである、請求項2に記載の方法。
- 前記脱溶媒化がドラム乾燥、直接乾燥、又は水蒸気脱溶媒化によって行われる、請求項1に記載の方法。
- 前記安定剤が、炭化水素油の存在下で前記ポリマーに添加される、請求項1に記載の方法。
- 前記開始剤がブチルリチウムである、請求項1に記載の方法。
- 前記炭化水素溶媒がヘキサン類の1種又は複数種である、請求項1に記載の方法。
- 前記共役ジオレフィンが1,3−ブタジエンである、請求項1に記載の方法。
- 前記重合ステップが芳香族ビニル化合物の存在を含む、請求項1に記載の方法。
- 前記芳香族ビニル化合物がスチレンである、請求項9に記載の方法。
- 前記炭化水素油が黒油である、請求項5に記載の方法。
- 水蒸気脱溶媒化の後に前記ポリマーを乾燥することを含む、請求項1に記載の方法。
- 請求項1に記載の方法により製造されるポリマー。
- 充填剤及び請求項13に記載のポリマーを含有するゴム組成物。
- 請求項14に記載のゴム組成物を含有するサイドウォール及び/又はトレッドを備えるタイヤ。
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PCT/US2013/044288 WO2013184783A2 (en) | 2012-06-06 | 2013-06-05 | Method of making polymers, polymer compositions and articles containing such polymers |
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SG11201606487PA (en) * | 2014-02-28 | 2016-09-29 | Exxonmobil Chem Patents Inc | Nanocomposite mooney viscosity stability |
EP3301120B1 (en) * | 2015-12-18 | 2020-02-05 | LG Chem, Ltd. | Method for preparing modified conjugated diene-based polymer |
JP6679398B2 (ja) * | 2016-04-25 | 2020-04-15 | 株式会社ブリヂストン | 変性ポリマーの製造方法、変性ポリマー、ゴム組成物及びタイヤ |
JP6752053B2 (ja) * | 2016-05-24 | 2020-09-09 | 旭化成株式会社 | 共役ジエン重合体の製造方法及びゴムベールの製造方法 |
KR102468899B1 (ko) | 2017-12-22 | 2022-11-22 | 꽁빠니 제네날 드 에따블리세망 미쉘린 | 적어도 2개의 트리알콕시실릴 그룹을 포함하는 화합물, 디엔 엘라스토머 작용화제로서의 이의 용도, 개질된 디엔 엘라스토머 및 개질된 디엔 엘라스토머를 함유하는 조성물 |
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RU2649008C2 (ru) | 2018-03-29 |
JP2015520272A (ja) | 2015-07-16 |
BR112014030696A2 (pt) | 2017-06-27 |
WO2013184783A3 (en) | 2014-03-20 |
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RU2014153539A (ru) | 2016-08-10 |
KR20150021550A (ko) | 2015-03-02 |
EP2859020A2 (en) | 2015-04-15 |
US10400089B2 (en) | 2019-09-03 |
EP2859020A4 (en) | 2016-02-24 |
SG11201408036QA (en) | 2015-01-29 |
CN104428321A (zh) | 2015-03-18 |
EP2859020B1 (en) | 2020-02-12 |
WO2013184783A2 (en) | 2013-12-12 |
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