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WO2013075805A2 - Compositions époxy - Google Patents

Compositions époxy Download PDF

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Publication number
WO2013075805A2
WO2013075805A2 PCT/EP2012/004767 EP2012004767W WO2013075805A2 WO 2013075805 A2 WO2013075805 A2 WO 2013075805A2 EP 2012004767 W EP2012004767 W EP 2012004767W WO 2013075805 A2 WO2013075805 A2 WO 2013075805A2
Authority
WO
WIPO (PCT)
Prior art keywords
methyl
glycidyl ester
weight
mixture
composition
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/EP2012/004767
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English (en)
Other versions
WO2013075805A3 (fr
Inventor
Denis Heymans
Christophe Steinbrecher
Cédric Le Fevere de Ten Hove
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.)
Hexion Research Belgium SA
Hexion Inc
Original Assignee
Momentive Specialty Chemicals Research SA
Momentive Specialty Chemicals Inc
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 Momentive Specialty Chemicals Research SA, Momentive Specialty Chemicals Inc filed Critical Momentive Specialty Chemicals Research SA
Publication of WO2013075805A2 publication Critical patent/WO2013075805A2/fr
Publication of WO2013075805A3 publication Critical patent/WO2013075805A3/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

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
    • C08G59/20—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
    • C08G59/223—Di-epoxy compounds together with monoepoxy 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
    • C08G59/36—Epoxy compounds containing three or more epoxy groups together with mono-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
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/04—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers only
    • C08G65/22—Cyclic ethers having at least one atom other than carbon and hydrogen outside the ring
    • 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
    • C08K5/00—Use of organic ingredients
    • C08K5/04—Oxygen-containing compounds
    • C08K5/15—Heterocyclic compounds having oxygen in the ring
    • C08K5/151—Heterocyclic compounds having oxygen in the ring having one oxygen atom in the ring
    • C08K5/1515—Three-membered rings
    • 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

  • the present invention relates to a epoxy resin curable compositions comprising a mixture of ⁇ , ⁇ -branched alkane carboxylic glycidyl esters derived from butene oligomers characterized in that the sum of the concentration of the blocked and of the highly branched isomers is maximum 55%, preferably below 40%, and most preferably below 30% weight on total composition, which lead for example to improved softening of the matrix derived thereof.
  • the invention relates to epoxy resin curable compositions comprising aliphatic tertiary saturated carboxylic acids or , ⁇ -branched alkane carboxylic acids, which contain 9 or 13 carbon atoms and which provide glycidyl esters with a branching level of the alkyl groups depending on the olefin feedstock used and/or the oligomerisation process therof, and which is defined as below .
  • the glycidyl esters can be obtained according PCT/EP2010/003334 or the US6433217.
  • well chosen blend of isomers of the glycidyl ester of mixture compositions of neo-acid (C9 or C13 acids) glycidyl ester is providing for example a good softening of the composition thereof, is a mixture where the sum of the concentration of blocked and highly branched isomers is maximum 55%, preferably below 40%, and most preferably below 30% weight on total composition.
  • Highly branched isomers are defined as isomers of neo-acids having at least 5 methyl groups.
  • Neo-acids for example neononanoic acids (V9) with secondary or a tertiary carbon atoms in the ⁇ position defined as blocking isomers.
  • Mixture compositions of neononanoic (C9) acids glycidyl esters of the present invention providing for example a good flexibility of the cured matrix is a mixture where the sum of the concentration of the blocked and of the highly branched isomers derivatives is maximum 55%, preferably below 40%, and most preferably below 30% weight on total composition.
  • compositions of neononanoic acids glycidyl esters mixture is comprising 2,2-dimethyl heptanoic acid glycidyl ester or 2-methyl 2-ethyl hexanoic acid glycidyl ester or 2-methyl 2-ethyl 3-methyl pentanoic acid glycidyl esters.
  • compositions of neononanoic acids glycidyl esters mixture is comprising 2-methyl 2-ethyl 3- methyl pentanoic acid glycidyl esters (sum of stereoisomers) below 40%, preferably below 30% and most preferably below or equal 25% weight on total composition.
  • compositions of neononanoic acids glycidyl esters mixture is comprising 2-methyl 2-ethyl hexanoic acid glycidyl ester above 10% , preferably above 30% and most preferably above 45% weight on total composition .
  • the above compositions of the glycidyl ester mixture is comprising 2,2-dimethyl heptanoic acid glycidyl ester and 2-methyl 2-ethyl hexanoic acid glycidyl ester and 2- methyl 2-ethyl 3-methyl pentanoic acid glycidyl esters (sum of stereoisomers) is above 40%, preferably 55% and most preferably 65% weight on total composition.
  • a preferred composition is comprising a mixture of 2,2- dimethyl heptanoic acid glycidyl ester in 1 to 15 weight% and 2-methyl 2-ethyl hexanoic acid glycidyl ester in 40 to 70 weight% and 2-methyl 2-ethyl 3-methyl pentanoic acid glycidyl esters (sum of stereoisomers) in 8 to 32 weight% on total composition.
  • a further preferred composition is comprising a mixture of 2,2-dimethyl heptanoic acid glycidyl ester in 2 to 10 weight% and 2-methyl 2-ethyl hexanoic acid glycidyl ester in 47 to 61 weight% and 2-methyl 2-ethyl 3-methyl pentanoic acid glycidyl esters (sum of stereoisomers) in 10 to 25 weight% on total composition.
  • the above glycidyl esters compositions can be used for example, as reactive diluent in formulations comprising epoxy resins such as EPIKOTE 828.
  • the curing agents can be amines, anhydrides or acids, like diethylenetriamine, nadic methyl anhydride or cyclohexanedicarboxylic acid respectively.
  • the glycidyl esters compositions can be used as reactive diluent for epoxy based formulations such as examplified in the technical brochure of Momentive (Product Bulletin: Cardura E10P The Unique Reactive Diluent SC-521) or in the Shell Chemical Bulletin (Bulletin / starting formulation (EPIKOTE epoxy resins) : EPIKOTE 816MV / EPI-CURE F205 based trowellable floor and patching compound; EK 5.2.1.6 Issued
  • neo-acid can be determined using gas chromatography, using a flame ionization detector (FID). 0.5 ml sample is diluted in analytical grade dichloromethane and n-octanol may be used as internal standard. The conditions presented below result in the approximate retention times given in table 1. In that case n-octanol has a retention time of approximately 8.21 minute .
  • FID flame ionization detector
  • the GC method has the following settings:
  • Carrier gas Helium
  • Injection volume 1 ⁇ CP Wax 58 CB is a Gas chromatography column available from Agilent Technologies.
  • the isomers of neononanoic acid as illustrative example have the structure (R 1 R 2 R 3 ) -C-COOH where the three R groups are linear or branched alkyl groups having together a total of 7 carbon atoms.
  • the isomers content is calculated from the relative peak area of the chromatogram obtained assuming that the response factors of all isomers are the same.
  • Rl R2 R3 groups Blocking [Minutes]
  • the isomer distribution of glycidyl esters of neo-acid can be determined by gas chromatography, using a flame ionization detector (FID) . 0.5 ml sample is diluted in analytical grade dichloromethane .
  • FID flame ionization detector
  • the GC method has the following settings:
  • Carrier gas Helium
  • S/SL injector 250°C CP Wax 58 CB is a Gas chromatography column available from Agilent Technologies.
  • R 1 R 2 R 3 -C-COO-CH 2 - CH(0)CH 2 where the three R groups are linear or branched alkyl groups having together a total of 7 carbon atoms.
  • the isomers content is calculated from the relative peak area of the chromatogram obtained assuming that the response factors of all isomers are the same.
  • GC-MS method can be used to identify the various isomers providing that the analysis is done by a skilled analytical expert .
  • Gelation time the time in minutes required for a mixture of resin and curing agent, maintained at a fixed temperature, to reach the stage in the process of hardening at which the resistance to the movement of a slowly reciprocating plunger immersed in the mixture reaches a specific value.
  • Apparatus Gel timer, according to BS 2782: Part 8, Method 835C, with disposable glass disk plungers. (Tecam Gel Timer, model GT3) .
  • Aluminum container ID 40 to 47 mm, depth not less than 75 mm and wall thickness 0.35 to 0.51 mm.
  • VISCOSITY Dynamic Viscosity of the mixture (resin + curing agent) in mPa.s, is measured according to ASTM D 2393. The temperature is 25°C. The apparatus used is a Brookfield DVII, with a spindle LV II (for low viscosities) . FIBRE WETTING
  • Wetting time the time in minutes, needed for 2 grams of the mixture to penetrate a glass fiber mat, until the surface goes from a glossy to a matt appearance (the mixture is absorbed by the glass mat) .
  • Spot size diameter of the spot in mm, after curing at 25°C of the 2 grams of the mixture.
  • Glass mat a chopped strand mat of size-coated chopped strands, with a thickness of 450 g/m 2 .
  • Test specimens of the dimensions (80X10X4) mm were cut from the casting sheets by a diamond saw. Moulds used for the castings consisted of 2 steel plates with a 4 mm frame in between. The castings were cured in the mould.
  • the carbon atom in alpha position of the carboxylic acid is always a tertiary carbon atom
  • the carbon atom(s) in pposition can either be primary, secondary or tertiary.
  • Neononanoic acids (V9) with a secondary or a tertiary carbon atoms in the ⁇ position are defined as blocking (blocked) isomers (Schemes 2 and 3) .
  • glycidyl esters compositions discussed here above, can be as reactive diluent for epoxy curable compositions .
  • the epoxy curable compositions of the invention are based on a composition comprising a mixture of ⁇ , ⁇ -branched alkane
  • a prefer composition is that the glycidyl ester mixture is based on neononanoic (C9) acid mixture where the sum of the concentration of the blocked and of the highly branched isomers is maximum 55%, preferably below 40%, and most preferably below 30% weight on total composition.
  • neononanoic (C9) glycidyl ester mixture is comprising 2 , 2-dimethyl heptanoic acid glycidyl ester or 2- methyl 2-ethyl hexanoic acid glycidyl ester or 2-methyl 2- ethyl 3-methyl pentanoic acid glycidyl ester.
  • composition of the glycidyl ester mixture is comprising 2-methyl 2-ethyl 3-methyl pentanoic acid glycidyl esters (sum of stereoisomers) below 40%, preferably below 30% and most preferably below or equal 25% weight on total composition.
  • composition of the glycidyl ester mixture is comprising 2-methyl 2-ethyl hexanoic acid glycidyl ester above 10% , preferably above 30% and most preferably above 45% weight on total composition.
  • composition of the glycidyl ester mixture is comprising 2, 2-dimethyl heptanoic acid glycidyl ester and 2-methyl 2-ethyl hexanoic acid glycidyl ester and 2-methyl 2-ethyl 3-methyl pentanoic acid glycidyl esters (sum of stereoisomers) is above 40%, preferably 55% and most preferably 65% weight on total composition.
  • composition of the glycidyl ester mixture is comprising 2, 2-dimethyl heptanoic acid glycidyl ester in 1 to 15 weight% and 2-methyl 2-ethyl hexanoic acid glycidyl ester in 40 to 70 weight% and 2-methyl 2-ethyl 3-methyl pentanoic acid glycidyl esters (sum of stereoisomers) in 8 to 32 weight% on total composition.
  • composition of the glycidyl ester mixture is comprising 2, 2-dimethyl heptanoic acid glycidyl ester in 2 to 10 weight% and 2-methyl 2-ethyl hexanoic acid glycidyl ester in 47 to 61 weight% and 2-methyl 2-ethyl 3-methyl pentanoic acid glycidyl esters (sum of stereoisomers) in 10 to 25 weight% on total composition.
  • the invention is also about the process to prepare the epoxy resin curable compositions, which are obtained by the incorporation of the mixture of ⁇ , ⁇ -branched alkane carboxylic glycidyl esters, as characterized above, into a mixture comprising epoxy resins and curing agents.
  • resins can be for instance aromatic or aliphatic halogenated or not halogenated glycidyl ether resins.
  • Commercially available halogenated resins are for example EPON 1163, EPIKOTE 5123, EPIKOTE 5119 and EPIKOTE 5112 (EPON/EPIKOTE are Resolution Performance Products Trademarks) or any other glycidyl ether of tetra-bromo-Bis-Phenol derivatives which contains more than 10 weight% of brome on resinous material.
  • non halogenated epoxy resins are the diglycidyl ether of Bisphenol A, and/or Bisphenol F and/or polyglycidyl ethers of phenol/cresol-formaldehyde novolacs, and the like.
  • Commercial examples of such resins are: EPIKOTE 828, EPIKOTE 834, EPIKOTE 1001, EPIKOTE 1002, EPIKOTE 154, EPIKOTE 164.
  • Amines, anhydrides and acids can be used as curing agent (hardener) .
  • amines can be for instance an aliphatic amine such as diethylenetriamine (DETA) , triethylenetetramine (TETA) , teraethylenepentamine (TEPA) , isophorone diamine (IPD), para- aminocyclohexane methylene (PACM), diamino cyclohexane (DCH) , meta-Xylene diamine (mXDA) , 4 , ' -Diamino 3 , 3 ' -dimethyl diCyclohexyl methane (DDCM) and adducts of aliphatic amines such as based on DETA, TETA, TEPA, IPD, PACM, DCH, mXDA, DDCM and the like; or aromatic amine such as MDA.
  • DETA diethylenetriamine
  • TETA triethylenetetramine
  • TEPA teraethylenepentamine
  • IPD isophorone diamine
  • PAM para- aminocyclohexan
  • Curable compositions disclosed herein may include one or more cycloaliphatic
  • Cycloaliphatic anhydride hardeners may include, for example, nadic methyl anhydride, hexahydrophthalic anhydride, trimellitic anhydride, dodecenyl succinic anhydride, phthalic anhydride, methyl hexahydrophthalic anhydride,
  • Anhydride curing agents may also include copolymers of styrene and maleic acid anhydrides and other anhydrides as described in US 6,613,839.
  • Hardener that can be used for curable compositions disclosed herein also include acids for instance derived from any above mentioned anhydride .
  • the invention is also related to a epoxy resin curable compositions useful for the impregnation of fibers applicable to the manufacturing of composite structures, laminates, coatings, flooring and putties applications comprising at least a mixture of ⁇ , -branched alkane carboxylic glycidyl esters described above.
  • said above composition is that it could be used in making composite material with glass, carbon or natural fiber by the technology known in the art.
  • Neononanoic glycidyl ester of composition C (see Table 2)
  • Table 2 Composition of the neononanoic glycidyl ester (according to the described gas chromatography method for glycidyl esters of neo-acid) GE5: glycidyl ester of pivalic acid obtained by reaction of the acid with epichlorhydrin .
  • Methacrylic acid available from Sigma - Aldrich
  • Methyl methacrylate available from Sigma - Aldrich
  • Butyl acrylate available from Sigma - Aldrich
  • Di-t-Amyl Peroxide is Luperox DTA from Arkema
  • A is a mixture of Xylene 50wt%, Toluene 30wt%, ShellsolA 10wt%, 2-Ethoxyethylacetate 10wt%.
  • Thinner B is butyl acetate
  • a resin for vacuum infusion of large structures such as yacht and wind turbines was prepared by mixing 27.7 part by weight of curing agent blend and 100 part of epoxy resins blend described here :
  • Epoxy resins blend 850 part by weight Epikote 828 and 150 part of glycidyl neononanoate , GE9S.
  • Curing Agent blend 650 part by weight of Jeffamine D230 and Jeffamine D230 is a polyoxyalkyleneamines available from Huntsman Corporation.
  • Epikote 828 is an epoxy resin available from Momentive Specialty Chemicals

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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)
  • Epoxy Resins (AREA)

Abstract

L'invention concerne des compositions époxy comprenant un mélange d'esters glycidyles d'acides carboxyliques d'alcane à ramifications α,α, dérivés d'oligomères de butène, caractérisées en ce que la somme de la concentration des isomères bloqués et des isomères hautement ramifiés représente au maximum 55%, de préférence moins de 40% et plus particulièrement moins de 30% en poids de la composition totale.
PCT/EP2012/004767 2011-11-25 2012-11-15 Compositions époxy Ceased WO2013075805A2 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
EP11075263 2011-11-25
EP11075263.1 2011-11-25
EP12002485.6 2012-04-05
EP12002485 2012-04-05

Publications (2)

Publication Number Publication Date
WO2013075805A2 true WO2013075805A2 (fr) 2013-05-30
WO2013075805A3 WO2013075805A3 (fr) 2013-11-14

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Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2831877A (en) 1952-03-24 1958-04-22 Studiengesellschaft Kohel Mit Production of carboxylic acids from olefins
US2876241A (en) 1954-05-15 1959-03-03 Studiengesellschaft Kohle Mit Process for the production of carboxylic acids
US2967873A (en) 1957-04-24 1961-01-10 Studiengesellschaft Kohle Mbh Process for the production of aliphatic and cycloaliphatic monocarboxylic acid alkyl esters
US3053869A (en) 1959-12-31 1962-09-11 Standard Oil Co Carboxylic acids
US3061621A (en) 1959-01-26 1962-10-30 Studiengesellschaft Kohle Mbh Process for producing carboxylic acids from olefins, carbon monoxide and water
EP1033360A1 (fr) 1999-02-26 2000-09-06 Oxeno Olefinchemie GmbH Procédé de préparation d'esters vinyliques à partir d'oligomers de butène
US6433217B1 (en) 1998-09-23 2002-08-13 Gerrit Gerardus Rosenbrand Process for the preparation of glycidylesters of branched carboxylic acids
US6613839B1 (en) 1997-01-21 2003-09-02 The Dow Chemical Company Polyepoxide, catalyst/cure inhibitor complex and anhydride

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2001056966A1 (fr) * 2000-02-02 2001-08-09 Resolution Research Nederland B.V. PROCEDE DE FABRICATION POUR LA PREPARATION D"ACIDES CARBOXYLIQUES A RAMIFICATION $G(a), A TENEUR REDUITE EN ISOMERES A RAMIFICATION BETA
EP1281700A1 (fr) * 2001-07-31 2003-02-05 Resolution Research Nederland B.V. Procédé de préparation d'acides carboxyliques alpha-alpha-branchés permettant la préparation d'esters plus doux
JP5449150B2 (ja) * 2007-06-28 2014-03-19 ビーエーエスエフ ソシエタス・ヨーロピア Ｃ１０アルカン酸グリシドエステル及びその使用
EP2261220A1 (fr) * 2009-06-11 2010-12-15 Hexion Specialty Chemicals Research Belgium S.A. Procédé de préparation d'esters glycidyliques d'acides monocarboxyliques ramifiés
EP2447241A1 (fr) * 2010-10-19 2012-05-02 Momentive Specialty Chemicals Research Belgium Esters glycidyliques d'acides néo-pélargoniques à ramification alpha, synthèse et utilisations
WO2012052126A1 (fr) * 2010-10-19 2012-04-26 Momentive Specialty Chemicals Research Belgium S.A. Esters de glycidyle d'acides alpha,alpha-néononanoïques ramifiés, leur synthèse et leurs utilisations
EP2474537A1 (fr) * 2010-12-22 2012-07-11 Momentive Specialty Chemicals Research Belgium S.A. Esters glycidyliques de compositions d'acides ramifiés alpha
EP2768882B1 (fr) * 2011-10-19 2015-08-26 Hexion Research Belgium SA Compositions de résines polyols acryliques
US20140287252A1 (en) * 2011-10-19 2014-09-25 Momentive Specialty Chemicals Inc. Polyester polyol resins compositions

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2831877A (en) 1952-03-24 1958-04-22 Studiengesellschaft Kohel Mit Production of carboxylic acids from olefins
US2876241A (en) 1954-05-15 1959-03-03 Studiengesellschaft Kohle Mit Process for the production of carboxylic acids
US2967873A (en) 1957-04-24 1961-01-10 Studiengesellschaft Kohle Mbh Process for the production of aliphatic and cycloaliphatic monocarboxylic acid alkyl esters
US3061621A (en) 1959-01-26 1962-10-30 Studiengesellschaft Kohle Mbh Process for producing carboxylic acids from olefins, carbon monoxide and water
US3053869A (en) 1959-12-31 1962-09-11 Standard Oil Co Carboxylic acids
US6613839B1 (en) 1997-01-21 2003-09-02 The Dow Chemical Company Polyepoxide, catalyst/cure inhibitor complex and anhydride
US6433217B1 (en) 1998-09-23 2002-08-13 Gerrit Gerardus Rosenbrand Process for the preparation of glycidylesters of branched carboxylic acids
EP1033360A1 (fr) 1999-02-26 2000-09-06 Oxeno Olefinchemie GmbH Procédé de préparation d'esters vinyliques à partir d'oligomers de butène

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* Cited by examiner, † Cited by third party
Title
PRODUCT BULLETIN: CARDURA E10P THE UNIQUE REACTIVE DILUENT MSC-521

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