WO1991005814A1 - Ethers de vinyle synthetises a partir d'ethers de vinyle hydroxyles et de polyepoxydes - Google Patents

Ethers de vinyle synthetises a partir d'ethers de vinyle hydroxyles et de polyepoxydes Download PDF

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Publication number
WO1991005814A1
WO1991005814A1 PCT/US1990/005774 US9005774W WO9105814A1 WO 1991005814 A1 WO1991005814 A1 WO 1991005814A1 US 9005774 W US9005774 W US 9005774W WO 9105814 A1 WO9105814 A1 WO 9105814A1
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WO
WIPO (PCT)
Prior art keywords
value
compound
vinyl ether
formula
ether
Prior art date
Application number
PCT/US1990/005774
Other languages
English (en)
Inventor
Kou-Chang Liu
Fulvio J. Vara
James A. Dougherty
Paul D. Taylor
Original Assignee
Gaf Chemicals Corporation
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
Priority claimed from US07/424,472 external-priority patent/US5012011A/en
Priority claimed from US07/481,037 external-priority patent/US4980430A/en
Priority claimed from US07/481,084 external-priority patent/US4980428A/en
Application filed by Gaf Chemicals Corporation filed Critical Gaf Chemicals Corporation
Publication of WO1991005814A1 publication Critical patent/WO1991005814A1/fr

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Classifications

    • 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
    • C08G59/68—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 catalysts used
    • 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
    • C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
    • C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
    • C08F290/06—Polymers provided for in subclass C08G
    • 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
    • C08G59/14—Polycondensates modified by chemical after-treatment
    • C08G59/1433—Polycondensates modified by chemical after-treatment with organic low-molecular-weight compounds
    • C08G59/1438—Polycondensates modified by chemical after-treatment with organic low-molecular-weight compounds containing oxygen
    • C08G59/1444—Monoalcohols

Definitions

  • Certain radiation curable coatings and films such as those formed from the acrylates, particularly propane trimethanol triacrylate, trimethacrylate, pentaerythritol triacrylate, and hexanediol diacylate or methacrylate, are in great demand because of their rapid curing properties.
  • epoxy vinyl ethers having the formula
  • R is a polyvalent linear, branched or cyclic hydrocarbon radical having from 2 to 20 carbon atoms, optionally substituted with alkyleneoxy;
  • A is branched or linear C 1 to C 4 alkylene;
  • B is halogen or lower alkyl;
  • m has a value of from 0 to 4;
  • n has a value of from 0 to
  • p has a value of from 1 to 5 and Y is when p is 1 and is or a mixture of
  • epoxy vinyl ethers those wherein R is C 2 to C 6 alkylene, A is -CH 2 - or
  • R, A, B, m, n and p are as defined.
  • the mole ratio of reactants is critical and is the ratio where the number of epoxy groups in the reaction mixture exceeds the number of hydroxy groups in the
  • reaction mixture by at least one.
  • the overall mole ratio of reactant to coreactant is from 1:1 to 1:5.
  • the reaction can be carried out in the presence of air or in the absence of oxygen under a blanket of inert gas.
  • the present condensation reaction is carried out at a temperature of between about 100° and about 175°C. under atmospheric pressure for a period of from 0.5 to 200 hours.
  • Preferred reaction parameters include a temperature of from about 120° to about 160°C. for a period of from about 2 to about 100 hours.
  • the reaction is also conducted in the presence of a base catalyst such as particulate sodium, potassium, or lithium metal, sodium or potassium hydroxide or hydride.
  • a base catalyst such as particulate sodium, potassium, or lithium metal, sodium or potassium hydroxide or hydride.
  • the catalyst is present in an amount of from about 0.01 to about 2 wt. %, preferably from about 0.1 to about 1 wt. % of the total mixture.
  • Suitable hydroxylated vinyl ether reactants include the mono vinyl ether of cyclohexanetrimethanol, the monovinyl ether of cyclohexanedimethanol, the monovinyl ether of tris-(hydroxymethyl) ethane, the divinyl ether of 2-ethyl-2(hydroxymethyl)1,3-propanediol, the divinyl ether of tris(hydroxymethyl) ethane, tetra(hydroxyethyl) vinyloxy hexane, (2-hydroxyethyl) vinyl ether, (3-hydroxypropyl) vinyl ether, the monovinyl ether of 3-ethyl-1,6-hexanediol, (4-hydroxybutyl) vinyl ether, the monovinyl ether of
  • Suitable aromatic polyepoxy reactants include the terminally substituted diepoxy compounds of bisphenol A and bisphenol F, resins and compounds wherein one or more of the phenyl groups is substituted with halo or C 1 to C 4 alkyl radicals.
  • a commercially available group of diepoxy reactants suitable for use in the present reaction are the Epon epoxy resins supplied by Shell Chemical Company.
  • epoxy reactants are readily prepared by well known procedures, such as the procedure outlined on pages 10 through 21 of Chapter 2 of HANDBOOK OF EPOXY RESINS, by Henry Lee and Kris Neville, published by McGraw Hill Book Company, 1967.
  • the present compounds can be mixed with alkenyl ether, alkenyl ester, epoxide or
  • Cross-linking copolymerizations can be carried out in the presence of air to produce highly desirable films and coatings which retain the desirable properties of both monomers or their polymerized
  • Curable compositions containing between about 0 and about 80% of a vinyl ether, an epoxide, an acrylate or a methacrylate comonomer or a polymer thereof and between about 20% and about 100% of the present epoxy vinyl ether in the presence of from about 0.05 to about 5 wt. % of a cationic photoinitiator are suitable radiation curable coatings which are polymerized by exposure to UV light, electron beam, laser emission or other source of
  • triphenyl sulfonium salt of phosphorous hexafluoride including the triphenyl sulfonium salt of phosphorous hexafluoride, diphenyl iodium salt, tetrazolium chloride, phenyl onium salts or aryl alkyl onium salts, cationic initiators and/or free radical initiators such as
  • 2,2-dichloro-1-(4-phenoxyphenyl) ethanone and other free radical and cationic initiators which are suitably employed in this invention can be admixed with an acrylic compound normally not conducive to rapid cationic radiation curing, such as an acrylate or methacrylate comonomer, to effect curing within a few seconds exposure to a source of radiation.
  • an acrylic compound normally not conducive to rapid cationic radiation curing such as an acrylate or methacrylate comonomer
  • the compounds of this invention because of their sensitivity to polymerization by radiation, find application as photoresist materials.
  • Curing of the present compounds or their admixtures with comonomers can be effected in less than 1 second by exposure to between about 100 and about 800 millijoules/cm 2 of UV light, between about 0.5 and about 5 megarads of electron beam exposure or equivalent
  • epoxy vinyl ethers having the formula
  • polyphenyl vinyl ethers those wherein R is C 2 to C 6 alkylene, n has a value of from 1 to 12 and Y and Y' are are preferred. Most preferred of this group are those compounds where n and p have a value of from 1 to 4.
  • R, p and n are as defined.
  • the amounts of reactant and coreactant employed in the synthesis process to produce the epoxy polyphenyl product are critical. Specifically, the total number of
  • epoxy groups with respect to the total amount of -OH groups in the system, must be in excess of at least one.
  • n 20 and p is 1, there can be 21 epoxy GROUPS/OH.
  • p 1, only one epoxy group, of the original 22 epoxy groups, reacts.
  • the ratio of reactant to coreactant is 1:1, whereby the product has one unreacted epoxy group; however when 2 moles of the coreactant to 1 mole of the reactant is employed, the product contains 5 unreacted epoxy groups.
  • coreactant can vary from 1:0.5, where the product contains 1 remaining epoxy group, up to 1:1 where the product contains 5 remaining epoxy groups. Hence by controlling the amount of reactant to coreactant, or vice versa, all of the hydroxy groups of the hydroxylated vinyl ether will be reacted and the product will always contain at least one epoxy group. It is essential to retain an epoxy group in the product where derivatives of the present products are desired.
  • t has a value of from 1 to 22;
  • R' is C 2 to C 20 alkylene, alkoxyalkylene, arylene or aryloxyalkylene which radicals are optionally fluorinated;
  • R" is a divalent
  • radical having from 1 to 100 carbon atoms and is selected from the group of alkylene, arylene, alkarylene, aralkylene which groups are optionally substituted with lower alkyl or the radical
  • R is a polyvalent linear, branched or cyclic
  • hydrocarbon radical having from 2 to 20 carbon atoms
  • A is a divalent radical selected from the group of
  • B is lower alkyl; m has a value of from 0 to 4 and n has a value of from 0 to 20.
  • R', R" and t are as defined.
  • coreactant II is an oligomer, as described above for R", e.g.
  • the synthesis is carried out under mild conditions such as a temperature of between about 50° and 160°C. under
  • the reactants may be contacted in the absence or in the
  • the solvent can be employed in an amount up to 70% of the reaction
  • Suitable solvents include, toluene, xylene, the dimethyl ether of tri- or tetra- ethylene glycol and the like.
  • the reaction is carried out in the presence of between about 0.01 and about 3 wt. %, preferably between about 0.05 and about 1 wt. % of a base catalyst such as particulate sodium, potassium or lithium metal, a sodium, lithium or potassium hydroxide or hydride, and similar base catalysts. While the present reaction is not oxygen inhibited, it is preferred to conduct the reaction under a blanket of inert gas such as nitrogen.
  • vinyl ether epoxide reactant examples include [(vinyloxy) methyl] oxirane, [(vinyloxy) benzyl] oxirane, [(vinyloxy) phenyl] oxirane, [(vinyloxy) butyl] oxirane, [(vinyloxy) ethyl] oxirane, [(vinyloxy) octyl] oxirane, [(vinyloxy) dodecyl] oxirane, [(vinyloxy) tolyl] oxirane, [(vinyloxy)-2,3-dimethyl hexyl] oxirane,
  • Suitable fluoro alkanol reactants include pentafluoropropanol, pentafluorohexanol,
  • Preferred species of the oxirane reactant are [(vinyloxy) methyl] oxirane and the oligomers of equation B wherein n has a value of 0 or 1; m is zero; A is -C(CH 3 ) 2 - and R is butylene.
  • the above compounds have been found to be excellent release coating materials. Accordingly, they can be coated on a suitable substrate such as glass, ceramic, wood, metal, woven fabrics, paper and the like in
  • thicknesses ranging from 0.05 up to 5 mils to provide products having stain and soil resistance or labels which are easily removed from paper surfaces or backing materials for adhesive tapes and the like and many other applications which are apparent from their properties.
  • curing the products of the present invention is easily effected at room temperature under ambient pressure conditions by exposure to a source of radiation such as UV light, an electron beam, lazer emission and the like in the presence of from about 0.05 to about 5 wt. % of a source of radiation such as UV light, an electron beam, lazer emission and the like in the presence of from about 0.05 to about 5 wt. % of a source of radiation such as UV light, an electron beam, lazer emission and the like in the presence of from about 0.05 to about 5 wt. % of a source of radiation such as UV light, an electron beam, lazer emission and the like in the presence of from about 0.05 to about 5 wt. % of a source of radiation such as UV light, an electron beam, lazer emission and the like in the presence of from
  • Suitable photoinitiators are the onium salts such as the triphenyl sulfonium salt of phosphorous hexafluoride, diphenyl iodium salt, tetrazolium chloride, phenyl onium salts or aryl alkyl onium salts and the like.
  • the amount of initiator employed is preferably between about 0.1 and about 2 wt. % with respect to reactants.
  • the present products can be cured in a period of less than 1 second, e.g. by exposure to between about 100 and about 800 millijoules/cm 2 UV light or between about 0.5 and about 5 megarads of electron beam emission.
  • the sensitivity of the present compounds to radiation curing makes them excellent candidates for use as photoresists.
  • the products of this invention can also be cured by conventional thermal processes employing a temperature of from about 50°C. to about 160°C.
  • Epon 828 epoxy resin (1131 g, 3 moles), 4-hydroxybutyl vinyl ether (348.5 g, 3 moles) and potassium hydroxide (0.5 g, 85% pellets) were charged into a 2-liter flask equipped with a mechanical stirrer, nitrogen inlet, thermometer and a condenser with a drying tube. The solution was heated at 120°C. for 12 hours and 150°C. for 48 hours under a blanket of nitrogen. Greater than 95% conversion was obtained. The gel-like product containing is recovered.
  • Epon 828 epoxy resin (2 mole), monovinyl ether of cyclohexane trimethanol (1 mole) and potassium hydroxide (0.4 g, 85% pellets) are charged into a 1-liter flask equipped as in Example 1. The solution is heated at 145°C. for 40 hours. Greater than 95% conversion is obtained.
  • the gel-like product containing is recovered.
  • Epon 826 epoxy resin (364 g, 1 mole), monovinyl ether of cyclohexane dimethanol (170 g, l mole) and
  • Example 1 The product of Example 1 is mixed with 1% of triphenyl sulfonium salt of phosphorous hexafluoride coated on an aluminum panel in a thickness of 0.15 mil and the coated substrate is exposed for less than 1 second at room temperature to 400 millijoules/cm 2 radiation from a medium pressure mercury vapor lamp, after which the coated substrate is removed. A completely homopolymerized protective coating having resistance to chemical attack is achieved.
  • Example 6 The procedure described in Example 4 is repeated except that 50% of the product of Example 2 was premixed with 50% of the divinyl ether of triethylene glycol. The coated substrate is completely cured in less than 1 second to a strong protective coating having high resistance to chemical attack.
  • Example 2 The general procedure in Example 2 is repeated, except that 2 moles of monovinyl ether of triethylene glycol are used.
  • the product is
  • Example 9 The procedure described in Example 9 is repeated except that the corresponding glycidyl ether of bisphenol F is substituted for the bisphenol A resin (Epon 828 epoxy resin) of Example 9. Also, decafluorohexanol is
  • Example 9 was repeated except that heptadecyl fluorodecanol was substituted for heptafluoropentanol of Example 9. About 100% conversion was achieved. The corresponding product is recovered.
  • Example 9 is repeated with substitution of each of the following alcohol reactants:
  • Example 9 is repeated except that [(vinyloxy) methyl] oxirane is substituted for Epon 828 in Example 9. About 100% conversion is achieved and a product having the structure
  • the above products are clear liquids or gel-like materials which, when coated on a dubstrate in a thickness of from about 0.15 to about 0.5 mil and exposed for less than one second at room temperature to 400
  • millijoules/cm 2 radiation from a medium pressure vapor lamp provide a cured soil and stain resistant barrier.

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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)
  • Emergency Medicine (AREA)
  • General Chemical & Material Sciences (AREA)
  • Epoxy Compounds (AREA)
  • Epoxy Resins (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Des éthers de vinyle époxydes sont synthétisés par la réaction d'un éther de vinyle hydroxylé et d'un éther aryle hydroxyalkyle diépoxyde réagissant ensemble tel qu'un composé diépoxyde de bisphénoles ou une résine novolac époxyde dans un rapport entre le nombre total de groupes époxydes et les groupes hydroxyles supérieur à au moins 1. Un éther de vinyle fluoré est synthétisé par la réaction d'une époxyde d'éther de vinyle et un fluoroalkanol. Les éthers de vinyle sont polymérisés par rayonnement induits cationiquement, et donnent des produits qui ne sont pas inhibés en oxygène et qui sont polymérisables après leur retrait du rayonnement, au contraire de systèmes à radicaux libres. Ils sont utilisés comme agents de libération et comme revêtements anti-souillure.
PCT/US1990/005774 1989-10-20 1990-10-11 Ethers de vinyle synthetises a partir d'ethers de vinyle hydroxyles et de polyepoxydes WO1991005814A1 (fr)

Applications Claiming Priority (8)

Application Number Priority Date Filing Date Title
US42445389A 1989-10-20 1989-10-20
US424,472 1989-10-20
US07/424,472 US5012011A (en) 1989-10-20 1989-10-20 Fluorinated vinyl ether
US424,453 1989-10-20
US07/481,037 US4980430A (en) 1989-10-20 1990-02-16 Epoxy vinyl ethers and synthesis of an epoxy vinyl ether from a hydroxylated vinyl ether and a diepoxide
US07/481,084 US4980428A (en) 1989-10-20 1990-02-16 Epoxy vinyl ethers and synthesis of an epoxy vinyl ether from a hydroxylated vinyl ether and a polyepoxide
US481,037 1990-02-16
US481,084 1990-02-16

Publications (1)

Publication Number Publication Date
WO1991005814A1 true WO1991005814A1 (fr) 1991-05-02

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Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US1990/005774 WO1991005814A1 (fr) 1989-10-20 1990-10-11 Ethers de vinyle synthetises a partir d'ethers de vinyle hydroxyles et de polyepoxydes

Country Status (4)

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EP (1) EP0496828A4 (fr)
AU (2) AU646824B2 (fr)
CA (1) CA2027918A1 (fr)
WO (1) WO1991005814A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0646580A3 (fr) * 1993-09-16 1995-10-11 Ciba Geigy Ag Composés de vinyléther avec des groupes fonctionnels additionnels différents de vinyléther et leur utilisation dans la formulation de compositions durcissables.

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4347343A (en) * 1981-01-21 1982-08-31 The Dow Chemical Company Thickened vinyl ester resin compositions

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2522649B1 (fr) * 1982-03-03 1987-07-10 Commissariat Energie Atomique
US4933420A (en) * 1988-09-23 1990-06-12 The Dow Chemical Company Epoxy resins containing phosphonium catalysts
ES2065361T3 (es) * 1988-10-14 1995-02-16 Dow Chemical Co Procedimiento para preparar resinas epoxidicas que contienen cloruros alifaticos no hidrolizables.
EP0399350A3 (fr) * 1989-05-22 1992-03-18 The Dow Chemical Company Compositions durcissables
US5098791A (en) * 1989-10-20 1992-03-24 Isp Investments Inc. Substrate coated with epoxy vinyl ether
JPH05506849A (ja) * 1990-02-06 1993-10-07 アイエスピー　インヴェストメンツ　インコーポレイテッド ビニルエーテル化合物
US5096783A (en) * 1990-02-16 1992-03-17 Isp Investments Inc. Substrate coated with epoxy vinyl ether

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4347343A (en) * 1981-01-21 1982-08-31 The Dow Chemical Company Thickened vinyl ester resin compositions

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See also references of EP0496828A4 *

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0646580A3 (fr) * 1993-09-16 1995-10-11 Ciba Geigy Ag Composés de vinyléther avec des groupes fonctionnels additionnels différents de vinyléther et leur utilisation dans la formulation de compositions durcissables.
US5605941A (en) * 1993-09-16 1997-02-25 Steinmann; Bettina Vinyl ether compounds having additional functional groups other than vinyl ether groups and the use thereof in the formulation of curable compositions
US5705316A (en) * 1993-09-16 1998-01-06 Ciba Specialty Chemicals Corporation Vinyl ether compounds having additional functional groups other than vinyl ether groups and the use thereof in the formulation of curable compositions
AU685824B2 (en) * 1993-09-16 1998-01-29 Vantico Ag Vinyl ether compounds having additional functional groups other than vinyl ether groups and the use thereof in the formulation of curable compositions
US5783615A (en) * 1993-09-16 1998-07-21 Ciba Specialty Chemicals Corporation Vinyl ether compounds having additional functional groups other than vinyl ether groups and the use thereof in the formulation of curable compositions
US5783712A (en) * 1993-09-16 1998-07-21 Ciba Specialty Chemicals Corporation Vinyl ether compounds having additional functional groups other than vinyl ether groups and the use thereof in the formulation of curable compositions

Also Published As

Publication number Publication date
EP0496828A1 (fr) 1992-08-05
AU646824B2 (en) 1994-03-10
AU5389394A (en) 1994-04-28
AU662670B2 (en) 1995-09-07
CA2027918A1 (fr) 1991-04-21
AU6729890A (en) 1991-05-16
EP0496828A4 (en) 1993-03-31

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