WO2009142900A1 - Epoxy resin reactive diluent compositions - Google Patents

Epoxy resin reactive diluent compositions Download PDF

Info

Publication number
WO2009142900A1
WO2009142900A1 PCT/US2009/042645 US2009042645W WO2009142900A1 WO 2009142900 A1 WO2009142900 A1 WO 2009142900A1 US 2009042645 W US2009042645 W US 2009042645W WO 2009142900 A1 WO2009142900 A1 WO 2009142900A1
Authority
WO
WIPO (PCT)
Prior art keywords
epoxy resin
cyclohexanedimethanol
cis
trans
diluent
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/US2009/042645
Other languages
English (en)
French (fr)
Inventor
Robert E. Hefner, Jr.
Hull, Jr.
James W. Ringer
John N. Argyropoulos
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Dow Global Technologies LLC
Original Assignee
Dow Global Technologies LLC
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Dow Global Technologies LLC filed Critical Dow Global Technologies LLC
Priority to EP09751129.9A priority Critical patent/EP2283093B1/en
Priority to CN2009801185303A priority patent/CN102037086B/zh
Priority to US12/988,874 priority patent/US8318834B2/en
Priority to JP2011510552A priority patent/JP5390600B2/ja
Publication of WO2009142900A1 publication Critical patent/WO2009142900A1/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • 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
    • C09D163/00—Coating compositions based on epoxy resins; Coating compositions based on derivatives of epoxy resins
    • 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
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
    • C08G59/22—Di-epoxy compounds
    • C08G59/226—Mixtures of di-epoxy compounds
    • 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
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
    • C08G59/32—Epoxy compounds containing three or more epoxy groups
    • C08G59/38—Epoxy compounds containing three or more epoxy groups together with di-epoxy compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins

Definitions

  • Another aspect of the present invention is directed to a curable epoxy resin composition comprising the above epoxy resin reactive diluent composition.
  • a further aspect of the present invention is directed to a cured epoxy resin prepared by a process of curing the above curable epoxy resin composition.
  • the epoxy resin diluent (A) of the present invention is prepared by a process (for example, an epoxidation reaction process) comprising reacting (a) a mixture of a cis-l,3-cyclohexanedimethanol, a trans- 1,3-cyclohexanedimethanol, a cis-l,4-cyclohexanedimethanol, and a trans- 1,4-cyclohexanedimethanol (also referred as the cis-l,3-and 1,4-cyclohexanedimethanol) with (b) an epihalohydrin, and (c) a basic acting substance.
  • a process for example, an epoxidation reaction process
  • the epoxy resin diluent (A) may be added to the epoxy resin reactive diluent composition in a functionally equivalent amount.
  • the epoxy resin diluent may be added in quantities which will provide the epoxy resin reactive diluent composition with a range of a desired viscosity according to the specific end use intended for the epoxy resin reactive diluent composition.
  • the desired viscosity is generally controlled by the temperature used for curing the epoxy resin reactive diluent composition, the particular curing catalyst and/or curing agent ultimately to be employed to cure the epoxy resin reactive diluent composition, and the desired ultimate mechanical properties for the cured epoxy resin reactive diluent composition.
  • Suitable curing catalysts include boron trifluoride, boron trifluoride etherate, aluminum chloride, ferric chloride, zinc chloride, silicon tetrachloride, stannic chloride, titanium tetrachloride, antimony trichloride, boron trifluoride monoethanolamine complex, boron trifluoride triethanolamine complex, boron trifluoride piperidine complex, pyridine-borane complex, diethanolamine borate, zinc fluoroborate, metallic acylates such as stannous octoate or zinc octoate, and any mixtures thereof.
  • the cure accelerator which can be employed herein includes, for example, mono, di, tri and tetraphenols; chlorinated phenols; aliphatic or cycloaliphatic mono or dicarboxylic acids; aromatic carboxylic acids; hydroxybenzoic acids; halogenated salicylic acids; boric acid; aromatic sulfonic acids; imidazoles; tertiary amines; aminoalcohols; aminopyridines; aminophenols; mercaptophenols; and any mixture thereof.
  • Viscosity was determined on an I.C.I. Cone and Plate Viscometer (model VR-4540) at 25°C.
  • a sample was applied to the viscometer and held for 2 minutes, then the viscosity was checked and the reading was taken after 15 seconds.
  • One or more duplicate viscosity tests were completed using a fresh aliquot of the particular product being tested. The individual measurements were averaged.
  • Example 4 Preparation and Characterization of 10 / 90, 25 / 75 and 50 / 50 wt. % Blends of Qligomer-free CHDM MGE and CHDM DGE Mixture with DGE BPA and the Polyalkylenepolyamine Cured Product Thereof
  • the cured product was a rigid, yellow colored, transparent solid.
  • Example 7 Part C A portion (25.00 g, 0.1413 epoxide eq) of the master batch blend from Comparative Experiment G Part A above was combined with a phenalkamine curing agent (17.66 g, 0.1413 amine hydrogen eq) described in Example 7 Part C.
  • the casting was prepared, cured, postcured, with test pieces prepared and tested for flexural properties using the method of Example 7 Part A.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Epoxy Resins (AREA)
PCT/US2009/042645 2008-05-22 2009-05-04 Epoxy resin reactive diluent compositions Ceased WO2009142900A1 (en)

Priority Applications (4)

Application Number Priority Date Filing Date Title
EP09751129.9A EP2283093B1 (en) 2008-05-22 2009-05-04 Epoxy resin reactive diluent compositions
CN2009801185303A CN102037086B (zh) 2008-05-22 2009-05-04 环氧树脂反应性稀释剂组合物
US12/988,874 US8318834B2 (en) 2008-05-22 2009-05-04 Epoxy resin reactive diluent compositions
JP2011510552A JP5390600B2 (ja) 2008-05-22 2009-05-04 エポキシ樹脂反応性希釈剤組成物

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US5523908P 2008-05-22 2008-05-22
US61/055,239 2008-05-22

Publications (1)

Publication Number Publication Date
WO2009142900A1 true WO2009142900A1 (en) 2009-11-26

Family

ID=40793144

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2009/042645 Ceased WO2009142900A1 (en) 2008-05-22 2009-05-04 Epoxy resin reactive diluent compositions

Country Status (6)

Country Link
US (1) US8318834B2 (https=)
EP (1) EP2283093B1 (https=)
JP (1) JP5390600B2 (https=)
CN (1) CN102037086B (https=)
TW (1) TW201002780A (https=)
WO (1) WO2009142900A1 (https=)

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2012047420A2 (en) 2010-09-30 2012-04-12 Dow Global Technologies Llc Thermosettable compositions and thermosets therefrom
WO2014093115A3 (en) * 2012-12-14 2014-11-27 Dow Global Technologies Llc High solids epoxy coatings
US8962792B2 (en) 2010-09-30 2015-02-24 Dow Global Technologies Llc Process for preparing epoxy resins
US9080059B2 (en) 2010-09-30 2015-07-14 Blue Cube Ip Llc Coating compositions
US9284434B2 (en) 2010-09-30 2016-03-15 Blue Cube Ip Llc Epoxy resin compositions
US9371414B2 (en) 2010-09-30 2016-06-21 Blue Cube Ip Llc Epoxy resin adducts and thermosets thereof
WO2019234038A1 (de) * 2018-06-07 2019-12-12 All.Bones Gmbh Polymermischung sowie deren verwendung im 3d-druck
CN110819202A (zh) * 2018-08-07 2020-02-21 广东万爱建筑科技有限公司 一种应用于建筑铝模板免脱模剂的石墨烯涂料

Families Citing this family (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20110054056A1 (en) * 2008-05-22 2011-03-03 Hefner Jr Robert E Thermoset polyurethanes
WO2014078219A1 (en) * 2012-11-13 2014-05-22 Dow Global Technologies Llc Epoxy resin system containing polyethylene tetraamines for resin transfer molding processes
WO2014078218A1 (en) * 2012-11-13 2014-05-22 Dow Global Technologies Llc Epoxy resin system containing polyethylene tetramines and triethylene diamine catalyst for resin transfer molding processes
CN103665325A (zh) * 2013-11-25 2014-03-26 苏州宏泉高压电容器有限公司 环氧树脂及其制备方法
US9382472B2 (en) 2013-12-18 2016-07-05 Rohm And Haas Electronic Materials Llc Transformative wavelength conversion medium
US9464224B2 (en) 2013-12-18 2016-10-11 Rohm And Haas Electronic Materials Llc Transformative wavelength conversion medium
JP2015209516A (ja) * 2014-04-28 2015-11-24 株式会社クラレ 硬化性組成物、及び硬化物
JP6306419B2 (ja) * 2014-04-28 2018-04-04 株式会社クラレ モノグリシジルエーテル化合物、及びモノアリルエーテル化合物
WO2016209864A1 (en) * 2015-06-25 2016-12-29 Dow Global Technologies Llc Novel epoxy resin system for making carbon fiber composites
US10933389B2 (en) * 2017-07-28 2021-03-02 Swimc Llc Tinting water-borne and solvent-borne paints and stains with powdered colorants
US10934151B2 (en) * 2017-07-28 2021-03-02 Swimc Llc Tinting water-borne and solvent-borne paints and stains with water-only colorants
US11441027B2 (en) * 2017-10-24 2022-09-13 Toray Industries, Inc. Epoxy resin composition, prepreg, and fiber-reinforced composite material
ES2944118T3 (es) * 2017-12-21 2023-06-19 Huntsman Advanced Mat Americas Llc Sistema epoxi curable
US10822517B2 (en) * 2018-11-28 2020-11-03 Industrial Technology Research Institute Resin composition and cured resin composition
WO2021092074A1 (en) * 2019-11-05 2021-05-14 Cambium Biomaterials, Inc. Composition and method for manufacturing resins
US12473439B2 (en) 2020-07-08 2025-11-18 Swimc Llc Paint tinting adjuvant with siccative for liquid colorant system

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4497764A (en) * 1982-09-30 1985-02-05 Exxon Research & Engineering Co. Epoxy resin compositions of enhanced creep resistance
US5736620A (en) 1989-01-17 1998-04-07 The Dow Chemical Company Glycidyl ether compounds containing mesogenic moieties
EP1118628A1 (de) * 2000-01-21 2001-07-25 HILTI Aktiengesellschaft Härtbare Zwei-Komponenten-Mörtelmasse und deren Verwendung
WO2004069892A1 (en) * 2003-02-03 2004-08-19 Ppg Industries Ohio Inc. Solvent borne 2k coating compositions
WO2006029140A1 (en) * 2004-09-03 2006-03-16 Dow Global Technologies Inc. Emulsifiable polyisocyanate
WO2007092071A1 (en) * 2006-02-03 2007-08-16 Dow Global Technologies Inc. 1,3/1,4-cyclohexane dimethanol based monomers and polymers

Family Cites Families (23)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4548961A (en) * 1982-09-30 1985-10-22 Exxon Research & Engineering Co. Epoxy resin compositions of enhanced creep resistance
US4578453A (en) 1984-11-23 1986-03-25 Eastman Kodak Company High molecular weight polyesters
US4623701A (en) 1985-07-10 1986-11-18 The Dow Chemical Company Multifunctional epoxy resins
US5073595A (en) * 1987-12-23 1991-12-17 Minnesota Mining And Manufacturing Company Epoxide resin compositions and method
US5239406A (en) * 1988-02-12 1993-08-24 Donnelly Corporation Near-infrared reflecting, ultraviolet protected, safety protected, electrochromic vehicular glazing
US5355245A (en) * 1988-02-12 1994-10-11 Donnelly Corporation Ultraviolet protected electrochemichromic rearview mirror
US4885319A (en) * 1988-02-29 1989-12-05 Gaf Corporation Solvent resistant irradiation curable coatings
JPH0459878A (ja) * 1990-06-28 1992-02-26 Nippon Paint Co Ltd 粉体塗料組成物
US5354797A (en) * 1992-08-31 1994-10-11 E. I. Du Pont De Nemours And Company Coating composition of hydroxy functional acrylic polymer, polyol and polyisocyanate crosslinking agent
ATE206725T1 (de) * 1994-04-06 2001-10-15 Ppg Ind Ohio Inc 1,4-cyclohexan-dimethanol enthaltende beschichtungszusammensetzungen
US5681907A (en) * 1996-01-04 1997-10-28 Air Products And Chemicals, Inc. Fast cure amines for ambient and subambient cure of epoxy resins comprising methylamine adducts
KR20050121761A (ko) * 2000-01-19 2005-12-27 히다치 가세고교 가부시끼가이샤 반도체용 접착필름, 반도체용 접착필름 부착 리드프레임 및이것을 사용한 반도체장치
JP3681978B2 (ja) * 2000-12-19 2005-08-10 株式会社巴川製紙所 光反射板および反射型液晶表示装置
US6548175B2 (en) * 2001-01-11 2003-04-15 International Business Machines Corporation Epoxy-siloxanes based electrically conductive adhesives for semiconductor assembly and process for use thereof
CA2469820C (en) * 2001-12-28 2010-02-23 Jim Surjan Adhesive of epoxy compound, aliphatic amine and tertiary amine
TWI223736B (en) * 2002-12-19 2004-11-11 Ind Tech Res Inst Hybrid photoresist with multi reaction models and process for forming pattern using the same
DE10317646A1 (de) * 2003-04-17 2004-11-04 Cognis Deutschland Gmbh & Co. Kg Strahlungshärtbare Massen
US6818293B1 (en) * 2003-04-24 2004-11-16 Eastman Chemical Company Stabilized polyester fibers and films
US20070110957A1 (en) * 2004-03-16 2007-05-17 Kensaku Higashi Anisotropic diffusing medium and production method therefor
JP4135940B2 (ja) * 2004-10-20 2008-08-20 株式会社巴川製紙所 異方性拡散媒体
US7560821B2 (en) * 2005-03-24 2009-07-14 Sumitomo Bakelite Company, Ltd Area mount type semiconductor device, and die bonding resin composition and encapsulating resin composition used for the same
US7425594B2 (en) * 2005-11-23 2008-09-16 Ppg Industries Ohio, Inc. Copolymer of glycidyl ester and/or ether with polyol
US20110039982A1 (en) 2008-05-22 2011-02-17 Hefner Jr Robert E Epoxy resins and processes for preparing the same

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4497764A (en) * 1982-09-30 1985-02-05 Exxon Research & Engineering Co. Epoxy resin compositions of enhanced creep resistance
US5736620A (en) 1989-01-17 1998-04-07 The Dow Chemical Company Glycidyl ether compounds containing mesogenic moieties
EP1118628A1 (de) * 2000-01-21 2001-07-25 HILTI Aktiengesellschaft Härtbare Zwei-Komponenten-Mörtelmasse und deren Verwendung
WO2004069892A1 (en) * 2003-02-03 2004-08-19 Ppg Industries Ohio Inc. Solvent borne 2k coating compositions
WO2006029140A1 (en) * 2004-09-03 2006-03-16 Dow Global Technologies Inc. Emulsifiable polyisocyanate
WO2007092071A1 (en) * 2006-02-03 2007-08-16 Dow Global Technologies Inc. 1,3/1,4-cyclohexane dimethanol based monomers and polymers

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
ARGYROPOULOS J ET AL: "Unoxol Diol: A New Liquid Cycloaliphatic Diol for Coatings Applications", PAINT AND COATINGS INDUSTRY, WESTERN TRADE PUBL., CANOGA PARK, CA, US, 1 June 2006 (2006-06-01), pages 1 - 5, XP002432852, ISSN: 0884-3848 *
HENRY LEE; KRIS NEVILLE: "Handbook of Epoxy Resins"

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2012047420A2 (en) 2010-09-30 2012-04-12 Dow Global Technologies Llc Thermosettable compositions and thermosets therefrom
US8962792B2 (en) 2010-09-30 2015-02-24 Dow Global Technologies Llc Process for preparing epoxy resins
US9068039B2 (en) 2010-09-30 2015-06-30 Dow Global Technologies Llc Thermosettable compositions and thermosets therefrom
US9080059B2 (en) 2010-09-30 2015-07-14 Blue Cube Ip Llc Coating compositions
US9284434B2 (en) 2010-09-30 2016-03-15 Blue Cube Ip Llc Epoxy resin compositions
US9371414B2 (en) 2010-09-30 2016-06-21 Blue Cube Ip Llc Epoxy resin adducts and thermosets thereof
WO2014093115A3 (en) * 2012-12-14 2014-11-27 Dow Global Technologies Llc High solids epoxy coatings
US10584261B2 (en) 2012-12-14 2020-03-10 Blue Cube Ip Llc High solids epoxy coatings
WO2019234038A1 (de) * 2018-06-07 2019-12-12 All.Bones Gmbh Polymermischung sowie deren verwendung im 3d-druck
CN110819202A (zh) * 2018-08-07 2020-02-21 广东万爱建筑科技有限公司 一种应用于建筑铝模板免脱模剂的石墨烯涂料

Also Published As

Publication number Publication date
EP2283093A1 (en) 2011-02-16
JP5390600B2 (ja) 2014-01-15
TW201002780A (en) 2010-01-16
CN102037086B (zh) 2013-08-28
JP2011521075A (ja) 2011-07-21
CN102037086A (zh) 2011-04-27
US20110046266A1 (en) 2011-02-24
US8318834B2 (en) 2012-11-27
EP2283093B1 (en) 2014-04-09

Similar Documents

Publication Publication Date Title
EP2283093B1 (en) Epoxy resin reactive diluent compositions
US9074041B2 (en) Curable epoxy resin compositions and composites made therefrom
CN102037049B (zh) 环氧树脂的加合物及其制备方法
EP2621992B1 (en) Epoxy resin adducts and thermosets thereof
EP2621990B1 (en) Thermosettable compositions and thermosets therefrom
EP2826801B1 (en) Amines and polymeric phenols and usage thereof as curing agents in one component epoxy resin compositions
EP2746312A2 (en) Epoxy resin compositions, methods of making same, and articles thereof
US20220106479A1 (en) Composition comprising a polymer based on epoxide compounds
EP2384345A1 (en) Divinylarene dioxide formulations for vacuum resin infusion molding
US20110060076A1 (en) Epoxy resins derived from seed oil based alkanolamides and a process for preparing the same
TWI515217B (zh) 二氧化二乙烯基芳烴樹脂組成物
EP2900725B1 (en) Adduct compositions
US20110039981A1 (en) Epoxy resins derived from non-seed oil based alkanolamides and a process for preparing the same
WO2018047799A1 (ja) エポキシ化合物、エポキシ化合物の製造方法、エポキシ化合物含有組成物、塗料及び硬化物

Legal Events

Date Code Title Description
WWE Wipo information: entry into national phase

Ref document number: 200980118530.3

Country of ref document: CN

121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 09751129

Country of ref document: EP

Kind code of ref document: A1

DPE1 Request for preliminary examination filed after expiration of 19th month from priority date (pct application filed from 20040101)
WWE Wipo information: entry into national phase

Ref document number: 12988874

Country of ref document: US

Ref document number: 2009751129

Country of ref document: EP

WWE Wipo information: entry into national phase

Ref document number: 2011510552

Country of ref document: JP

NENP Non-entry into the national phase

Ref country code: DE