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
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- 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
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Polymers & Plastics (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Pest Control & Pesticides (AREA)
- Polyurethanes Or Polyureas (AREA)
- Biological Depolymerization Polymers (AREA)
- Reinforced Plastic Materials (AREA)
- Fertilizers (AREA)
- Polyesters Or Polycarbonates (AREA)
Applications Claiming Priority (5)
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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)
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| ES2643842T3 true ES2643842T3 (es) | 2017-11-24 |
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Families Citing this family (31)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103732644B (zh) | 2011-06-13 | 2016-03-23 | 因温斯特技术公司 | 作为用于聚氨酯和聚异氰脲酸酯聚合物的前体的来自环己烷氧化副产物流的脂族聚酯多元醇 |
| KR20150013300A (ko) * | 2012-05-18 | 2015-02-04 | 바스프 에스이 | 분진 억제 응집체 |
| US20150274922A1 (en) * | 2012-09-21 | 2015-10-01 | Invista North America S.A.R.L. | Materials comprising nvr polyols |
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| US9156745B2 (en) * | 2013-05-07 | 2015-10-13 | Koch Agronomic Services, Llc | Fertilizer granules having polymeric coating with organic carbonate |
| PL3004267T3 (pl) * | 2013-06-07 | 2020-02-28 | Swimc Llc | Uretanowa kompozycja powlekająca do podłoża metalowego |
| PL229712B1 (pl) * | 2014-04-01 | 2018-08-31 | Korzeniowski Waclaw Chemenergia | Sposób wytwarzania żywic poliestrowych |
| CN106660891A (zh) | 2014-04-28 | 2017-05-10 | 巴斯夫欧洲公司 | 形成包封肥料的方法 |
| WO2015189045A1 (en) * | 2014-06-11 | 2015-12-17 | 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 |
| US10563005B2 (en) | 2016-01-21 | 2020-02-18 | Invista North America S.A.R.L. | Aromatic polyester polyol compositions |
| CN111065501A (zh) * | 2017-08-23 | 2020-04-24 | 巴斯夫欧洲公司 | 在己内酰胺和己内酰胺低聚物存在下生产木质纤维素材料的方法 |
| 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 |
| JP7696837B2 (ja) * | 2019-06-05 | 2025-06-23 | オーエムエス インベストメンツ,インコーポレイテッド | 放出制御型肥料組成物 |
| 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 |
| 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 |
| ATE487696T1 (de) | 2004-02-17 | 2010-11-15 | Chevron Phillips Chemical Co | Schwefelhaltige zusammensetzungen und verfahren zu deren herstellung |
| US7682656B2 (en) | 2004-06-14 | 2010-03-23 | Agruim Inc. | Process and apparatus for producing a coated product |
| US20060115586A1 (en) | 2004-11-30 | 2006-06-01 | Baozhong Xing | 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 |
| JP2009504546A (ja) | 2005-08-09 | 2009-02-05 | アグリウム・インコーポレイテッド | コーティング添加剤としてエポキシ化脂肪酸トリグリセリドを用いる肥効調節型肥料 |
| 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 |
| EP2134822A2 (en) * | 2007-04-09 | 2009-12-23 | Dow Global Technologies Inc. | Capped polyester polyol lubricant composition |
| PL2178811T3 (pl) * | 2007-08-13 | 2011-07-29 | Sumitomo Chemical Co | Granulka powlekana żywicą uretanową |
| US7771505B2 (en) | 2008-07-16 | 2010-08-10 | Agrium Inc. | Controlled release fertilizer composition |
| US20120101009A1 (en) | 2008-12-18 | 2012-04-26 | Invista North America S.A.R.L. | Cyclohexane oxidation process byproduct stream derivatives and methods for using the same |
| EP2384344B1 (en) * | 2009-01-30 | 2019-10-16 | INVISTA Textiles (U.K.) Limited | Aromatic polyesterpolyols, isocyanuratemodified polyurethane foams, and methods of making them |
| CN102388008B (zh) | 2009-04-08 | 2014-09-24 | 巴斯夫欧洲公司 | 通过氢化低聚酯和聚酯而生产1,6-己二醇的方法 |
| JP2012527519A (ja) * | 2009-05-19 | 2012-11-08 | インビスタ テクノロジーズ エス エイ アール エル | ポリオール組成物、樹脂混合組成物、噴霧組成物および各々の使用方法および各々の製造方法 |
| US8303680B2 (en) * | 2009-06-24 | 2012-11-06 | Basf Se | Encapsulated particle |
| CN103732644B (zh) | 2011-06-13 | 2016-03-23 | 因温斯特技术公司 | 作为用于聚氨酯和聚异氰脲酸酯聚合物的前体的来自环己烷氧化副产物流的脂族聚酯多元醇 |
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| EP2718340B1 (en) | 2017-08-09 |
| JP2014522446A (ja) | 2014-09-04 |
| PL2718340T3 (pl) | 2017-12-29 |
| EP2718340A1 (en) | 2014-04-16 |
| US9056940B2 (en) | 2015-06-16 |
| CN103732644A (zh) | 2014-04-16 |
| WO2012173938A1 (en) | 2012-12-20 |
| US20130042659A1 (en) | 2013-02-21 |
| CN103732644B (zh) | 2016-03-23 |
| KR20140039288A (ko) | 2014-04-01 |
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