ZA200900084B - Method to improve cold flow resistance of polymers - Google Patents
Method to improve cold flow resistance of polymers Download PDFInfo
- Publication number
- ZA200900084B ZA200900084B ZA200900084A ZA200900084A ZA200900084B ZA 200900084 B ZA200900084 B ZA 200900084B ZA 200900084 A ZA200900084 A ZA 200900084A ZA 200900084 A ZA200900084 A ZA 200900084A ZA 200900084 B ZA200900084 B ZA 200900084B
- Authority
- ZA
- South Africa
- Prior art keywords
- polymer
- alditol
- acetal
- sorbitol
- polymers
- Prior art date
Links
- 229920000642 polymer Polymers 0.000 title claims description 121
- 238000000034 method Methods 0.000 title claims description 41
- 229920001971 elastomer Polymers 0.000 claims description 69
- 229920001223 polyethylene glycol Polymers 0.000 claims description 58
- 150000005846 sugar alcohols Chemical class 0.000 claims description 58
- 239000000806 elastomer Substances 0.000 claims description 50
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 claims description 48
- 239000000203 mixture Substances 0.000 claims description 43
- FMZUHGYZWYNSOA-VVBFYGJXSA-N (1r)-1-[(4r,4ar,8as)-2,6-diphenyl-4,4a,8,8a-tetrahydro-[1,3]dioxino[5,4-d][1,3]dioxin-4-yl]ethane-1,2-diol Chemical compound C([C@@H]1OC(O[C@@H]([C@@H]1O1)[C@H](O)CO)C=2C=CC=CC=2)OC1C1=CC=CC=C1 FMZUHGYZWYNSOA-VVBFYGJXSA-N 0.000 claims description 28
- 229940087101 dibenzylidene sorbitol Drugs 0.000 claims description 28
- 239000011414 polymer cement Substances 0.000 claims description 28
- 125000000962 organic group Chemical group 0.000 claims description 24
- 239000002904 solvent Substances 0.000 claims description 17
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 16
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 16
- -1 3,4-dimethylbenzylidene Chemical group 0.000 claims description 13
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- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 claims description 5
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 claims description 4
- 239000005062 Polybutadiene Substances 0.000 claims description 4
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Classifications
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- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
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- 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
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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
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- C08K5/05—Alcohols; Metal alcoholates
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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
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- C08K5/05—Alcohols; Metal alcoholates
- C08K5/053—Polyhydroxylic alcohols
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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
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- C08K5/1575—Six-membered rings
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L47/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds; Compositions of derivatives of such polymers
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- 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
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- 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
- C08J2321/00—Characterised by the use of unspecified rubbers
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Processes Of Treating Macromolecular Substances (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US1791307P | 2007-12-31 | 2007-12-31 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200900084B true ZA200900084B (en) | 2010-03-31 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200900084A ZA200900084B (en) | 2007-12-31 | 2009-01-05 | Method to improve cold flow resistance of polymers |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US8138248B2 (ko) |
| EP (1) | EP2075282B1 (ko) |
| JP (2) | JP2009173926A (ko) |
| KR (1) | KR101532788B1 (ko) |
| CN (1) | CN101475694B (ko) |
| BR (1) | BRPI0815685A8 (ko) |
| ES (1) | ES2567177T3 (ko) |
| RU (1) | RU2485146C2 (ko) |
| ZA (1) | ZA200900084B (ko) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8673998B2 (en) * | 2010-09-22 | 2014-03-18 | Bridgestone Corporation | Polymer compositions with improved cold flow |
| WO2013086480A2 (en) * | 2011-12-09 | 2013-06-13 | Bridgestone Corporation | Method for producing polydienes and polydiene copolymers with reduced cold flow |
| WO2013101648A1 (en) | 2011-12-31 | 2013-07-04 | Bridgestone Corporation | Functionalized polymer |
| RU2680501C1 (ru) * | 2017-12-12 | 2019-02-21 | Публичное акционерное общество "СИБУР Холдинг" | Способ получения функционализированных сополимеров на основе сопряженных диенов, сополимеры, полученные этим способом, резиновые смеси на основе данных сополимеров |
Family Cites Families (69)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4899244A (ko) * | 1972-03-30 | 1973-12-15 | ||
| JPS6043373B2 (ja) * | 1977-01-24 | 1985-09-27 | 株式会社トクヤマ | 押出成形性の改良されたポリオレフイン系樹脂組成物 |
| JPS5580781A (en) | 1978-12-02 | 1980-06-18 | Kondo Teruhisa | Antioxidant against carbonaceous substance and its manufacture and antioxidant treatment against same |
| JPS56115701A (en) * | 1980-02-19 | 1981-09-11 | Nippon Oil Co Ltd | Improved composition for capturing small animal |
| US4384064A (en) * | 1980-06-02 | 1983-05-17 | National Starch And Chemical Corporation | Vinyl copolymer adhesives |
| JPS578232A (en) * | 1980-06-17 | 1982-01-16 | Sumitomo Rubber Ind Ltd | Rubber composition for solid golf ball |
| JPS5755950A (en) * | 1980-07-04 | 1982-04-03 | Adeka Argus Chem Co Ltd | Polybutadiene resin composition |
| US4429140A (en) | 1981-12-29 | 1984-01-31 | New Japan Chemical Co., Ltd. | Process for preparing dibenzylidene sorbitols and dibenzylidene xylitols |
| JPS58147473A (ja) * | 1982-02-27 | 1983-09-02 | Sekisui Chem Co Ltd | ホツトメルト接着剤組成物 |
| DE3321713A1 (de) | 1983-06-16 | 1984-12-20 | Basf Ag, 6700 Ludwigshafen | Thermoplastische formmassen |
| US4906706A (en) | 1986-09-05 | 1990-03-06 | Japan Synthetic Rubber Co., Ltd. | Modified conjugated diene polymer and process for production thereof |
| US5064910A (en) | 1986-09-05 | 1991-11-12 | Japan Synthetic Rubber Co., Ltd. | Preparation of conjugated diene polymers modified with an organo-tin or germanium halide |
| JPS63256635A (ja) | 1987-04-14 | 1988-10-24 | Bridgestone Corp | 改良されたゴム組成物 |
| JPH089679B2 (ja) * | 1988-09-16 | 1996-01-31 | 新日本理化株式会社 | 樹脂改質用ジアセタール組成物及び結晶性樹脂組成物 |
| IT1230756B (it) | 1989-02-17 | 1991-10-29 | Enichem Elastomers | Metodo per la preparazione di polibutadiene a lavorabilita' migliorata. |
| US5106999A (en) | 1990-06-26 | 1992-04-21 | The Procter & Gamble Company | Process for preparing dibenzylidene-d-sorbitol compounds |
| US5268439A (en) | 1991-01-02 | 1993-12-07 | Bridgestone/Firestone, Inc. | Tin containing elastomers and products having reduced hysteresis properties |
| FR2673187B1 (fr) | 1991-02-25 | 1994-07-01 | Michelin & Cie | Composition de caoutchouc et enveloppes de pneumatiques a base de ladite composition. |
| JP3211274B2 (ja) | 1991-08-27 | 2001-09-25 | 旭化成株式会社 | 共役ジエン系重合体の製造方法 |
| JP3230532B2 (ja) | 1991-08-28 | 2001-11-19 | 旭化成株式会社 | 共役ジエン系重合体の製造法 |
| JPH0535835U (ja) * | 1991-10-03 | 1993-05-14 | 東燃化学株式会社 | すべり止め用足ゴム |
| US5198484A (en) * | 1992-05-01 | 1993-03-30 | Milliken Research Corporation | Polyolefin composition containing ultrafine sorbitol and xylitol acetals |
| US5332810A (en) | 1992-10-02 | 1994-07-26 | Bridgestone Corporation | Solubilized anionic polymerization initiator and preparation thereof |
| US5329005A (en) * | 1992-10-02 | 1994-07-12 | Bridgestone Corporation | Soluble anionic polymerization initiators and preparation thereof |
| US6025450A (en) | 1992-10-02 | 2000-02-15 | Bridgestone Corporation | Amine containing polymers and products therefrom |
| US5844050A (en) | 1993-07-30 | 1998-12-01 | Nippon Zeon Co., Ltd. | Modified conjugated diene polymer, process for producing same and composition comprising same |
| DE4436059A1 (de) | 1994-10-10 | 1996-04-11 | Bayer Ag | Verfahren zur Herstellung von mittels Nd-Katalysatoren polymerisierten Dienkautschuken mit niedrigem cold-flow und geringem Eigengeruch |
| US6080835A (en) | 1995-02-01 | 2000-06-27 | Bridgestone Corporation | Aminoalkyllithium compounds containing cyclic amines and polymers therefrom |
| JP3555809B2 (ja) | 1995-06-19 | 2004-08-18 | 株式会社ブリヂストン | ラジアルタイヤ |
| AT405285B (de) * | 1995-09-07 | 1999-06-25 | Semperit Ag | Kautschukmischung |
| US5719207A (en) | 1996-03-18 | 1998-02-17 | The Goodyear Tire & Rubber Company | Silica reinforced rubber composition and tire with tread |
| JP3606411B2 (ja) | 1996-07-10 | 2005-01-05 | 株式会社ブリヂストン | タイヤ加硫成型用金型およびその製造方法 |
| JP3117645B2 (ja) | 1996-09-03 | 2000-12-18 | 株式会社ブリヂストン | 空気入りラジアルタイヤ |
| US5786441A (en) | 1996-12-31 | 1998-07-28 | Bridgestone Corporation | Polymers, elastomeric compounds and products thereof, derived from novel amine compounds containing side-chain organolithium moieties |
| EP0863165B1 (en) | 1997-03-05 | 2003-06-04 | JSR Corporation | Method of producing conjugated diene polymers |
| JP3724125B2 (ja) | 1997-07-15 | 2005-12-07 | Ｊｓｒ株式会社 | 共役ジエン系重合体の製造方法 |
| JP4489194B2 (ja) | 1997-03-05 | 2010-06-23 | Ｊｓｒ株式会社 | 共役ジエン系重合体の製造方法 |
| US6221943B1 (en) | 1997-07-11 | 2001-04-24 | Bridgestone Corporation | Processability of silica-filled rubber stocks |
| US5935893A (en) | 1997-08-01 | 1999-08-10 | Bridgestone Corporation | Aliphatic solutions of aminoalkyllithium compounds |
| US5971046A (en) | 1997-09-17 | 1999-10-26 | Bridgestone/Firestone, Inc. | Method and apparatus for bonding an active tag to a patch and a tire |
| ES2205559T3 (es) | 1997-11-06 | 2004-05-01 | New Japan Chemical Co.,Ltd. | Procedimiento para el moldeo de gel orientado de una composicion de resina de poliolefina y objeto moldeado obtenido mediante dicho procedimiento. |
| US6136914A (en) * | 1998-03-13 | 2000-10-24 | Bridgestone Corporation | Anionic polymerization initiators for preparing macro-branched diene rubbers |
| EP1865005B1 (en) | 1998-06-25 | 2009-06-24 | Idemitsu Kosan Co., Ltd. | Propylene polymer and composition containing the same, molded object and laminate comprising these, and processes for producing propylene polymer and composition containing the same |
| GB9908202D0 (en) | 1999-04-12 | 1999-06-02 | Unilever Plc | Cosmetic compositions |
| JP4898045B2 (ja) | 1999-11-12 | 2012-03-14 | 株式会社ブリヂストン | ランタニドを基にした触媒を用いて製造した変性重合体 |
| EP1237935B1 (en) | 1999-11-12 | 2007-01-24 | Bridgestone Corporation | Modified polymers prepared with lanthanide-based catalysts |
| US6977281B1 (en) | 1999-11-12 | 2005-12-20 | Bridgestone Corporation | Modified polymers prepared with lanthanide-based catalysts |
| DE10005556A1 (de) | 2000-02-09 | 2001-08-23 | Cognis Deutschland Gmbh | Hochviskose Mikroemulsionen |
| EP1297974B1 (en) | 2000-07-03 | 2017-03-15 | Bridgestone Corporation | Pneumatic tire |
| JP4965055B2 (ja) | 2000-11-10 | 2012-07-04 | 株式会社ブリヂストン | 新規な官能化剤を用いて製造した官能化高シス−１，４−ポリブタジエン |
| US6807994B2 (en) * | 2001-03-13 | 2004-10-26 | The Goodyear Tire & Rubber Company | Pneumatic tire having a rubber component containing a rubber gel and syndiotatic 1,2-polybutadiene |
| DE10120091A1 (de) * | 2001-04-25 | 2002-11-07 | Continental Ag | Kautschukmischung für Laufstreifen von Reifen |
| US6559211B2 (en) | 2001-05-23 | 2003-05-06 | Milliken & Company | Highly versatile thermoplastic nucleators |
| JP3933966B2 (ja) * | 2002-03-15 | 2007-06-20 | 日本ゼオン株式会社 | ジエン系ゴム、その製造方法、ならびにゴム組成物、その製造方法および架橋物 |
| JP2004149614A (ja) * | 2002-10-29 | 2004-05-27 | Yokohama Rubber Co Ltd:The | 熱可塑性エラストマー組成物 |
| JP4522947B2 (ja) | 2002-10-30 | 2010-08-11 | 株式会社ブリヂストン | モノマーのアニオン重合に硫黄含有開始剤を使用する方法 |
| US7888454B2 (en) | 2004-04-26 | 2011-02-15 | Milliken & Company | Substituted alditol compounds, compositions, and methods |
| US20060014903A1 (en) * | 2004-07-14 | 2006-01-19 | Thierry Vromman | Thermoplastic vulcanizates with enhanced cooling and articles made therefrom |
| JP2006307138A (ja) | 2004-10-26 | 2006-11-09 | Sumitomo Chemical Co Ltd | エチレン−α−オレフィン共重合体 |
| WO2006066395A1 (en) * | 2004-12-20 | 2006-06-29 | Lanxess Inc. | A process for reducing the cold flow of a rubber compound blend |
| US7335712B2 (en) | 2005-04-21 | 2008-02-26 | Bridgestone Corporation | Process of producing a siloxy-functionalized polymer |
| US20060264590A1 (en) | 2005-05-20 | 2006-11-23 | Bridgestone Corporation | Anionic polymerization initiators and polymers therefrom |
| US7868110B2 (en) | 2005-05-20 | 2011-01-11 | Bridgestone Corporation | Anionic polymerization initiators and polymers therefrom |
| US7879952B2 (en) | 2005-12-28 | 2011-02-01 | Bridgestone Corporation | Functionalized polymers |
| US7662978B2 (en) | 2006-04-24 | 2010-02-16 | Milliken & Company | Dibenzylidene sorbitol (DBS)-based compounds, compositions and methods for using such compounds |
| US7671138B2 (en) | 2006-05-26 | 2010-03-02 | Bridgestone Corporation | Polymers functionized with hydrobenzamides |
| US7732534B2 (en) | 2006-08-28 | 2010-06-08 | Bridgestone Corporation | Polymers functionalized with nitro compounds |
| US8207270B2 (en) * | 2006-09-29 | 2012-06-26 | Exxonmobil Chemical Patents Inc. | Thermoplastic elastomer compositions, methods of making and articles made from the same |
| US8088868B2 (en) | 2006-12-19 | 2012-01-03 | Bridgestone Corporation | Polymers functionalized with protected oxime compounds |
-
2008
- 2008-12-26 RU RU2008151959/04A patent/RU2485146C2/ru active
- 2008-12-26 JP JP2008334918A patent/JP2009173926A/ja active Pending
- 2008-12-29 BR BRPI0815685A patent/BRPI0815685A8/pt active Search and Examination
- 2008-12-30 ES ES08254181.4T patent/ES2567177T3/es active Active
- 2008-12-30 EP EP08254181.4A patent/EP2075282B1/en not_active Expired - Fee Related
- 2008-12-31 CN CN2008101929950A patent/CN101475694B/zh not_active Expired - Fee Related
- 2008-12-31 KR KR1020080137825A patent/KR101532788B1/ko active IP Right Grant
- 2008-12-31 US US12/347,397 patent/US8138248B2/en active Active
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2009
- 2009-01-05 ZA ZA200900084A patent/ZA200900084B/en unknown
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2014
- 2014-07-15 JP JP2014145016A patent/JP5833713B2/ja active Active
Also Published As
| Publication number | Publication date |
|---|---|
| CN101475694B (zh) | 2013-05-29 |
| KR101532788B1 (ko) | 2015-06-30 |
| JP2014237830A (ja) | 2014-12-18 |
| BRPI0815685A8 (pt) | 2019-01-15 |
| CN101475694A (zh) | 2009-07-08 |
| RU2485146C2 (ru) | 2013-06-20 |
| ES2567177T3 (es) | 2016-04-20 |
| KR20090073993A (ko) | 2009-07-03 |
| US8138248B2 (en) | 2012-03-20 |
| RU2008151959A (ru) | 2010-07-10 |
| EP2075282A1 (en) | 2009-07-01 |
| JP2009173926A (ja) | 2009-08-06 |
| EP2075282B1 (en) | 2016-01-06 |
| JP5833713B2 (ja) | 2015-12-16 |
| US20100004361A1 (en) | 2010-01-07 |
| BRPI0815685A2 (pt) | 2010-09-14 |
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