ES2643842T3 - Poliéster alipático de polióstil a partir de corrientes de subproducto de oxidación de ciclohexanos como precursores para los polimeros de poliuretano y polisisocianurato - Google Patents
Poliéster alipático de polióstil a partir de corrientes de subproducto de oxidación de ciclohexanos como precursores para los polimeros de poliuretano y polisisocianurato Download PDFInfo
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- ES2643842T3 ES2643842T3 ES12728918.9T ES12728918T ES2643842T3 ES 2643842 T3 ES2643842 T3 ES 2643842T3 ES 12728918 T ES12728918 T ES 12728918T ES 2643842 T3 ES2643842 T3 ES 2643842T3
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Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
- C08G18/4205—Polycondensates having carboxylic or carbonic ester groups in the main chain containing cyclic groups
- C08G18/4208—Polycondensates having carboxylic or carbonic ester groups in the main chain containing cyclic groups containing aromatic groups
- C08G18/4222—Polycondensates having carboxylic or carbonic ester groups in the main chain containing cyclic groups containing aromatic groups derived from aromatic polyhydroxy compounds and polycarboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C05—FERTILISERS; MANUFACTURE THEREOF
- C05C—NITROGENOUS FERTILISERS
- C05C9/00—Fertilisers containing urea or urea compounds
- C05C9/005—Post-treatment
-
- C—CHEMISTRY; METALLURGY
- C05—FERTILISERS; MANUFACTURE THEREOF
- C05G—MIXTURES OF FERTILISERS COVERED INDIVIDUALLY BY DIFFERENT SUBCLASSES OF CLASS C05; MIXTURES OF ONE OR MORE FERTILISERS WITH MATERIALS NOT HAVING A SPECIFIC FERTILISING ACTIVITY, e.g. PESTICIDES, SOIL-CONDITIONERS, WETTING AGENTS; FERTILISERS CHARACTERISED BY THEIR FORM
- C05G5/00—Fertilisers characterised by their form
- C05G5/30—Layered or coated, e.g. dust-preventing coatings
- C05G5/37—Layered or coated, e.g. dust-preventing coatings layered or coated with a polymer
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
- C08G18/4266—Polycondensates having carboxylic or carbonic ester groups in the main chain prepared from hydroxycarboxylic acids and/or lactones
- C08G18/4286—Polycondensates having carboxylic or carbonic ester groups in the main chain prepared from hydroxycarboxylic acids and/or lactones prepared from a combination of hydroxycarboxylic acids and/or lactones with polycarboxylic acids or ester forming derivatives thereof and polyhydroxy compounds
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
- C09D175/04—Polyurethanes
- C09D175/06—Polyurethanes from polyesters
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C31/00—Saturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C31/18—Polyhydroxylic acyclic alcohols
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2101/00—Manufacture of cellular products
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2115/00—Oligomerisation
- C08G2115/02—Oligomerisation to isocyanurate groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Polymers & Plastics (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- Materials Engineering (AREA)
- Pest Control & Pesticides (AREA)
- Polyurethanes Or Polyureas (AREA)
- Reinforced Plastic Materials (AREA)
- Fertilizers (AREA)
- Polyesters Or Polycarbonates (AREA)
- Biological Depolymerization Polymers (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
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| US201161496268P | 2011-06-13 | 2011-06-13 | |
| US201161496268P | 2011-06-13 | ||
| US201161496868P | 2011-06-14 | 2011-06-14 | |
| US201161496868P | 2011-06-14 | ||
| PCT/US2012/041951 WO2012173938A1 (en) | 2011-06-13 | 2012-06-11 | Aliphatic polyester polyols from cyclohexane oxidation byproduct streams as precursors for polyurethane and polyisocyanurate polymers |
Publications (1)
| Publication Number | Publication Date |
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| ES2643842T3 true ES2643842T3 (es) | 2017-11-24 |
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| CN (1) | CN103732644B (enExample) |
| ES (1) | ES2643842T3 (enExample) |
| PL (1) | PL2718340T3 (enExample) |
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Families Citing this family (32)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2012173938A1 (en) | 2011-06-13 | 2012-12-20 | Invista Technologies S.A.R.L. | Aliphatic polyester polyols from cyclohexane oxidation byproduct streams as precursors for polyurethane and polyisocyanurate polymers |
| WO2013173739A2 (en) * | 2012-05-18 | 2013-11-21 | Basf Se | An encapsulated particle |
| US20150274922A1 (en) * | 2012-09-21 | 2015-10-01 | Invista North America S.A.R.L. | Materials comprising nvr polyols |
| RU2640885C2 (ru) | 2012-11-16 | 2018-01-12 | Басф Се | Инкапсулированная частица удобрения, содержащая пестицид |
| CN103160236B (zh) * | 2013-04-17 | 2014-04-16 | 衡水前进油脂有限责任公司 | 一种利用植物油脂肪酸制备双组份彩钢板胶 |
| CN105555739A (zh) * | 2013-05-07 | 2016-05-04 | 科氏农艺服务有限责任公司 | 具有含有机碳酸酯的聚合物涂层的肥料颗粒 |
| BR112015030200B1 (pt) * | 2013-06-07 | 2021-12-21 | Swimc Llc | Composição de revestimento de uretano à base de solvente |
| PL229712B1 (pl) | 2014-04-01 | 2018-08-31 | Korzeniowski Waclaw Chemenergia | Sposób wytwarzania żywic poliestrowych |
| MX393696B (es) | 2014-04-28 | 2025-03-19 | Basf Se | Metodo de formacion de un fertilizante encapsulado. |
| US10507621B2 (en) * | 2014-06-11 | 2019-12-17 | Basf Se | Polyurethane compound for producing an integrated insulation component |
| CN104141231B (zh) * | 2014-08-02 | 2016-08-24 | 甄曰菊 | 一种织物涂层浆料及其制备方法 |
| JP6597039B2 (ja) * | 2015-08-11 | 2019-10-30 | 三菱ケミカル株式会社 | 接着剤、接着剤混合物及び木質ボード |
| WO2017127224A1 (en) | 2016-01-21 | 2017-07-27 | Invista North America S.A R.L. | Improved aromatic polyester polyol compositions |
| US12466105B2 (en) * | 2017-08-23 | 2025-11-11 | Basf Se | Method for producing lignocellulose materials in the presence of caprolactam and oligomers of caprolactam |
| CN107814909A (zh) * | 2017-11-13 | 2018-03-20 | 蒋艳玲 | 树脂板复合材料的制备方法 |
| WO2019117650A1 (ko) * | 2017-12-14 | 2019-06-20 | 주식회사 엘지화학 | 용출 제어형 비료 |
| KR102510340B1 (ko) | 2017-12-14 | 2023-03-15 | 주식회사 엘지화학 | 용출 제어형 비료 |
| CN108484313A (zh) * | 2018-02-06 | 2018-09-04 | 金华市众鑫农业科技有限公司 | 茶花专用缓释肥的制备方法 |
| CN114206808A (zh) * | 2019-06-05 | 2022-03-18 | Oms投资公司 | 控释肥料合成物 |
| CN111138659B (zh) * | 2020-01-14 | 2021-04-23 | 四川大学 | 一种非异氰酸酯路线制备三嵌段非离子型含氟短链表面活性剂的方法 |
| EP3851471A1 (en) | 2020-01-16 | 2021-07-21 | Purinowa spolka z o.o. | Method for obtaining high flame retardancy polyester polyols |
| CN111303373B (zh) * | 2020-02-25 | 2022-07-12 | 万华化学集团股份有限公司 | 一种低色度脲基甲酸酯组合物及其制备方法和应用 |
| US10919816B1 (en) | 2020-06-09 | 2021-02-16 | Surface Chemists Of Florida, Inc. | Epoxide moisture barrier coatings containing thermoplastic resins |
| US11193041B1 (en) * | 2020-06-09 | 2021-12-07 | Surface Chemists Of Florida, Inc. | Polyurethane moisture barrier coatings containing thermoplastic resins |
| US11180618B1 (en) * | 2020-08-05 | 2021-11-23 | Timeplast, Llc | Process of transforming a plastic extrusion system into a dynamic depolymerization reactor |
| CN111793380A (zh) * | 2020-08-25 | 2020-10-20 | 江苏冠军科技集团股份有限公司 | 一种含不参与光化学反应溶剂的涂料稀释剂及其制备方法和应用 |
| EP4015548A1 (en) * | 2020-12-18 | 2022-06-22 | Allnex Belgium, S.A. | Aqueous bio-based energy curable polyurethane composition |
| CN113512172B (zh) * | 2021-06-02 | 2022-02-22 | 茂施农业科技有限公司 | 一种聚氨酯控释肥包膜用的癸二酸副产脂肪酸聚酯多元醇 |
| CN114921162B (zh) * | 2021-07-20 | 2023-08-01 | 上海澳昌实业有限公司 | 一种水性透明耐磨阻燃罩面漆及其制备方法 |
| CN113817086B (zh) * | 2021-09-29 | 2022-11-11 | 韦尔通(厦门)科技股份有限公司 | 一种生物基光固化树脂组合物及其制备方法和应用 |
| CN118184933A (zh) | 2024-03-28 | 2024-06-14 | 茂施农业科技有限公司 | 一种含基于可再生原料的呋喃二甲酸的聚氨酯控释肥包膜材料及其应用和产品 |
| CN118374258B (zh) * | 2024-06-26 | 2024-10-29 | 上海京球新材料科技有限公司 | 一种胶粘剂及其制备方法 |
Family Cites Families (44)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3365490A (en) | 1966-08-05 | 1968-01-23 | Du Pont | Process for the production of dicarboxylic acids |
| PL93248B1 (enExample) * | 1975-05-02 | 1977-05-30 | ||
| US4166056A (en) * | 1978-04-13 | 1979-08-28 | Witco Chemical Corporation | Polyester plasticizer for vinyl resins derived from adipic acid process waste |
| US4233408A (en) * | 1979-05-07 | 1980-11-11 | Witco Chemical Corporation | Polyurethane foams from polyester precursor derived from adipic acid process waste |
| US4752637A (en) | 1984-08-15 | 1988-06-21 | Jim Walter Research Corp. | Binder composition for manufacture of fiberboard |
| US4609513A (en) | 1984-08-15 | 1986-09-02 | Jim Walter Research Corp. | Binder composition for manufacture of fiberboard |
| US5435821A (en) | 1985-12-12 | 1995-07-25 | Exxon Research & Engineering Co. | Controlled release vegetation enhancement agents coated with sulfonated polymers, method of production and prcesses of use |
| US4804403A (en) * | 1986-08-18 | 1989-02-14 | Melamine Chemicals, Inc. | Attrition-resistant, controlled release fertilizers |
| US4833182A (en) | 1986-09-29 | 1989-05-23 | Jim Walter Research Corp. | Isocyanate-polyester polyol binder for manufacture of cellulosic composites |
| US4898776A (en) | 1986-09-29 | 1990-02-06 | Jim Walter Reasearch Corp. | Isocyanate/surfactant-modified polyol binder for manufacture of lignocellulosic composites |
| PL151999B1 (pl) * | 1987-04-17 | 1990-10-31 | Sposób wytwarzania poliestroli | |
| PL162632B1 (pl) * | 1990-02-20 | 1993-12-31 | Politechnika Lodzka | Sposób wytwarzania oligoestroli PL |
| JP3082231B2 (ja) * | 1990-09-26 | 2000-08-28 | 大日本インキ化学工業株式会社 | 可塑剤及びそれを含むハロゲン含有樹脂組成物 |
| US5538531A (en) | 1991-06-24 | 1996-07-23 | Hudson; Alice P. | Controlled release fertilizers and methods of production |
| EP0606553A2 (en) * | 1993-01-11 | 1994-07-20 | Conoco Inc. | An ester base oil for lubricant compounds and process of making an ester base oil from an organic reaction by-product |
| US5374292A (en) | 1993-02-08 | 1994-12-20 | Pursell Industries | Machine system and process for producing attrition resistant slow release fertilizers |
| JPH0762180A (ja) * | 1993-08-20 | 1995-03-07 | Dainippon Ink & Chem Inc | 可塑剤及びそれを含むハロゲン含有樹脂組成物 |
| US5599374A (en) | 1994-09-23 | 1997-02-04 | Rlc Technologies, L.L.C. | Process for producing improved sulfur-coated urea slow release fertilizers |
| US5803946A (en) | 1996-06-20 | 1998-09-08 | Planet Polymer Technologies, Inc. | Controlled release plant nutrients |
| US5851261A (en) * | 1996-12-30 | 1998-12-22 | Bayer Corporation | Process for the production of polyurea encapsulated fertilizer particles and the encapsulated fertilizer particles produced by this process |
| US6338746B1 (en) | 1999-07-23 | 2002-01-15 | Rlc Technologies, L.L.C. | Polymer-sulfur-polymer coated fertilizers |
| US6663686B1 (en) | 2000-06-27 | 2003-12-16 | Agrium, Inc. | Controlled release fertilizer and method for production thereof |
| EP1172387A1 (en) | 2000-07-14 | 2002-01-16 | Huntsman International Llc | Process for preparing an elastomer |
| US6682751B1 (en) | 2001-09-12 | 2004-01-27 | Rlc Technologies, L.L.C. | Controlled-release pesticidal composition and method of making |
| US20040016276A1 (en) | 2002-07-26 | 2004-01-29 | Wynnyk Nick P. | Controlled release fertilizer having improved mechanical handling durability and method for production thereof |
| US20040020254A1 (en) | 2002-08-02 | 2004-02-05 | Agrium | Controlled release fertilizer and method for production thereof |
| US6703529B1 (en) | 2002-09-12 | 2004-03-09 | E. I. Du Pont De Nemours And Company | Process for oxidation of cyclohexane |
| US6995206B2 (en) | 2003-07-28 | 2006-02-07 | Hewlett-Packard Development Company, L.P. | Methods of preparing latex particulates with reactive functional groups |
| NZ549073A (en) | 2004-02-17 | 2010-10-29 | Agrium Inc | Thiol ester compositions and processes for making and using same |
| US7682656B2 (en) | 2004-06-14 | 2010-03-23 | Agruim Inc. | Process and apparatus for producing a coated product |
| WO2006058422A1 (en) | 2004-11-30 | 2006-06-08 | Agrium Inc. | Process and apparatus for coating a controlled release product in a rotating drum |
| US7267707B2 (en) | 2005-03-30 | 2007-09-11 | Florikan E.S.A. Corp. | Polyurethane encapsulated fertilizer |
| CN101282919B (zh) | 2005-08-09 | 2013-07-24 | 阿格里姆公司 | 使用环氧化脂肪酸甘油三酯油作为涂层添加剂的控释肥 |
| US7818906B2 (en) | 2006-03-24 | 2010-10-26 | CCS digital—fabric GmbH | Lightbox |
| US20070231369A1 (en) | 2006-03-31 | 2007-10-04 | Rlc Technologies, L.L.C. | Ruminant feed composition and method of making |
| WO2008124265A2 (en) * | 2007-04-09 | 2008-10-16 | Dow Global Technologies, Inc. | Capped polyester polyol lubricant composition |
| BRPI0721902B1 (pt) * | 2007-08-13 | 2022-04-12 | Sumitomo Chemical Company, Limited | Grânulo revestido com resina uretânica |
| US7771505B2 (en) * | 2008-07-16 | 2010-08-10 | Agrium Inc. | Controlled release fertilizer composition |
| KR20110100224A (ko) | 2008-12-18 | 2011-09-09 | 인비스타 테크놀러지스 에스.에이.알.엘. | 시클로헥산 산화 공정 부산물 스트림 유도체 및 그의 사용 방법 |
| WO2010088227A1 (en) * | 2009-01-30 | 2010-08-05 | Invista Technologies S.A. R.L. | Aromatic polyesterpolyols, isocyanuratemodified polyurethane foams, and methods of making them |
| EP2417087B1 (de) | 2009-04-08 | 2013-03-13 | Basf Se | Verfahren zur herstellung von 1,6-hexandiol durch hydrierung von oligo- und polyestern |
| EP2432818A4 (en) * | 2009-05-19 | 2016-02-10 | INVISTA Technologies S à r l | POLYOL COMPOSITIONS, RESIN MIXTURES, SPRAY COMPOSITIONS, AND METHODS OF USE, AND METHODS OF MAKING THE SAME |
| US8303680B2 (en) * | 2009-06-24 | 2012-11-06 | Basf Se | Encapsulated particle |
| WO2012173938A1 (en) | 2011-06-13 | 2012-12-20 | Invista Technologies S.A.R.L. | Aliphatic polyester polyols from cyclohexane oxidation byproduct streams as precursors for polyurethane and polyisocyanurate polymers |
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Also Published As
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| PL2718340T3 (pl) | 2017-12-29 |
| WO2012173938A1 (en) | 2012-12-20 |
| EP2718340A1 (en) | 2014-04-16 |
| CN103732644B (zh) | 2016-03-23 |
| US9056940B2 (en) | 2015-06-16 |
| EP2718340B1 (en) | 2017-08-09 |
| KR20140039288A (ko) | 2014-04-01 |
| CN103732644A (zh) | 2014-04-16 |
| JP2014522446A (ja) | 2014-09-04 |
| US20130042659A1 (en) | 2013-02-21 |
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