EP2456804A1 - Catalyse de formulations de résine époxyde présentant des catalyseurs difficilement solubles - Google Patents

Catalyse de formulations de résine époxyde présentant des catalyseurs difficilement solubles

Info

Publication number
EP2456804A1
EP2456804A1 EP10718949A EP10718949A EP2456804A1 EP 2456804 A1 EP2456804 A1 EP 2456804A1 EP 10718949 A EP10718949 A EP 10718949A EP 10718949 A EP10718949 A EP 10718949A EP 2456804 A1 EP2456804 A1 EP 2456804A1
Authority
EP
European Patent Office
Prior art keywords
composition according
reactive composition
diisocyanate
reactive
bis
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.)
Withdrawn
Application number
EP10718949A
Other languages
German (de)
English (en)
Inventor
Emmanouil Spyrou
Rainer LOMÖLDER
Susanne Kreischer
Andrea VÖCKER
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.)
Evonik Operations GmbH
Original Assignee
Evonik Degussa GmbH
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 Evonik Degussa GmbH filed Critical Evonik Degussa GmbH
Publication of EP2456804A1 publication Critical patent/EP2456804A1/fr
Withdrawn legal-status Critical Current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
    • C08G59/40—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 curing agents used
    • 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
    • C08G59/40—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 curing agents used
    • C08G59/4007—Curing agents not provided for by the groups C08G59/42 - C08G59/66
    • C08G59/4014—Nitrogen containing compounds
    • C08G59/4021—Ureas; Thioureas; Guanidines; Dicyandiamides
    • 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
    • C08G18/30—Low-molecular-weight compounds
    • C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
    • C08G18/3225—Polyamines
    • C08G18/3228—Polyamines acyclic
    • 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
    • C08G18/30—Low-molecular-weight compounds
    • C08G18/38—Low-molecular-weight compounds having heteroatoms other than oxygen
    • 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
    • C08G18/67—Unsaturated compounds having active hydrogen
    • C08G18/671—Unsaturated compounds having only one group containing active hydrogen
    • C08G18/6735—Unsaturated compounds containing the unsaturation at least partially in a non-aromatic carbocyclic ring
    • 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
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
    • C08G18/78—Nitrogen
    • C08G18/79—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates
    • C08G18/791—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing isocyanurate groups
    • C08G18/792—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing isocyanurate groups formed by oligomerisation of aliphatic and/or cycloaliphatic isocyanates or isothiocyanates
    • 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
    • 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
    • C08G59/686—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 containing nitrogen
    • 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 epoxy resin formulations with a special sparingly soluble catalyst mixture to increase reactivity.
  • latent hardeners eg. B. dicyandiamide
  • Epoxy resins are known (eg US 2,637,715 or US 3,391,113).
  • the advantages of dicyandiamide are above all in the toxicological harmlessness and in the chemically inert behavior, which leads to a good storage stability.
  • Catalysts that increase the reactivity, but does not significantly affect the storage stability.
  • the invention relates to reactive compositions containing substantially
  • Epoxy resins A) usually consist of glycidyl ethers based on
  • epoxy resin component A preference is given to using polyepoxides based on bisphenol A diglycidyl ether, bisphenol F diglycidyl ether or cycloaliphatic types.
  • Epoxy resins A) used selected from the group comprising epoxy resins A) based on bisphenol A diglycidyl ether, epoxy resins based on bisphenol F diglycidyl ether and cycloaliphatic types such.
  • epoxy resins A) based on bisphenol A diglycidyl ether epoxy resins based on bisphenol F diglycidyl ether and cycloaliphatic types such.
  • 3,4-epoxycyclohexyl-epoxyethane or 3,4-epoxycyclohexylmethyl-3,4-epoxy-cyclohexanecarboxylate with bisphenol A based epoxy resins and bisphenol F based epoxy resins are particularly preferred.
  • mixtures of epoxy resins can also be used as component A).
  • Latent hardeners B are either very slightly reactive, especially at low temperatures, or poorly soluble, often even both. According to the invention, latent hardeners which are suitable for the
  • uncatalyzed reaction (curing) with the component A) have the maximum of the exothermic reaction peak at temperatures above 150 0 C, and wherein those having the maximum of the exothermic reaction peak at temperatures above 170 0 C are particularly suitable (measured by DSC, onset at ambient temperature (usually at 25 0 C) heating rate 10 K / min, end point 250 0 C).
  • Suitable hardeners are those described in US Pat. No. 4,859,761 or EP 306 451. Preference is given to using substituted guanidines and aromatic amines. The most common representative of the substituted guanidines is dicyandiamide. Other substituted guanidines can be used, for. B.
  • aromatic amines 4,4'-diaminodiphenylsulfone.
  • Other aromatic diamines are also suitable, for. 3,3'-diaminodiphenylsulfone, 4,4'-methylenediamine, 1, 2 or 1, 3 or 1, 4-benzenediamines, bis (4-aminophenyl) -1,4-diisopropylbenzene (e.g.
  • Shell EPON 1061 bis (4-amino-3,5-dimethylphenyl) -1,4-diisopropylbenzene (e.g., Shell EPON 1062), diaminodiphenyl ether, diaminobenzophenone, 2,6-diaminopyridine, 2,4- Toluenediamine, diaminodiphenylpropanes, 1,5-diaminonaphthalene, xylenediamines, 1,1-bis-4-aminophenylcyclohexane, methylenebis (2,6-diethylaniline) (e.g., LONZACURE M-DEA ex Lonza), methylene bis- (2-isopropyl, 6-methylaniline) (e.g., LONZACURE M-MIPA ex Lonza), methylene bis (2,6-diisopropylaniline) (e.g., LONZACURE M-DIPA ex Lonza), 4-a
  • Suitable latent hardeners are also N-acylimidazoles, such as. B. 1- (2 ', 4', 6'-Thmethylbenzoyl) -2-phenylimidazole or i-benzoyl-2-isopropylimidazole.
  • N-acylimidazoles such as. B. 1- (2 ', 4', 6'-Thmethylbenzoyl) -2-phenylimidazole or i-benzoyl-2-isopropylimidazole.
  • Such compounds are described, for example, in US 4,436,892 and US 4,587,311.
  • hardeners are metal salt complexes of imidazoles, such as. As described in US 3,678,007 or US 3,677,978, Carbonkladazide such. Adipic dihydrazide, isophthalic dihydrazide or anthranilic acid hydrazide, thazine derivatives, e.g. 2-phenyl-4,6-diamino-s-triazine (benzoguanamine) or 2-lauryl-4,6-diamino-s-triazine (lauroguanamine) as well as melamine and its derivatives. The latter compounds are for. For example, described in US 3,030,247.
  • Suitable latent hardeners are also Cyanacetyltellen, such as.
  • Cyanacetyltellen such as.
  • Neopentylglykolbiscyanessigester cyanoacetic acid-N-isobutylamide, 1, 6-hexamethylene bis-cyanoacetate or
  • Suitable latent hardeners are also N-cyanacylamide compounds such.
  • Such compounds are described, for example, in US Pat. Nos. 4,529,821, 4,550,203 and 4,618,712.
  • aliphatic or cycloaliphatic di- and polyamines may be used if they are only reactive enough.
  • polyetheramines may be mentioned here, such as. It is also conceivable to use aliphatic or cycloaliphatic di- or polyamines whose reactivity is due to sticky and / or electronic influencing factors
  • mixtures of latent hardeners may also be used.
  • Dicyandiamide and 4,4'-diaminodiphenylsulfone are preferably used.
  • the amount ratio between the epoxy resin and the latent curing agent can be varied over a wide range. However, it has proved to be advantageous to use the latent curing agent about 1 -15 wt .-% based on the epoxy resin, preferably 4 - 10 wt .-%.
  • the NCO-containing component C1) used according to the invention can consist of any desired aromatic, aliphatic, cycloaliphatic and / or (cyclo) aliphatic di- and / or polyisocyanates.
  • aromatic di- or polyisocyanates are suitable as aromatic di- or polyisocyanates. Particularly suitable are 1, 3 and 1, 4-phenylene diisocyanate,
  • MDI Diphenylmethane diisocyanates
  • polymer-MDI oligomeric diphenylmethane diisocyanates
  • xylylene diisocyanate tetramethylxylylene diisocyanate
  • Suitable aliphatic di- or polyisocyanates advantageously have 3 to 16 carbon atoms, preferably 4 to 12 carbon atoms, in the linear or branched alkylene radical and suitable cycloaliphatic or (cyclo) aliphatic diisocyanates advantageously 4 to 18 carbon atoms, preferably 6 to 15 carbon atoms, in the cycloalkylene radical.
  • (cyclo) aliphatic diisocyanates the skilled worker understands at the same time cyclic and aliphatic bound NCO groups, as z.
  • B. isophorone diisocyanate is the case.
  • Examples are cyclohexane diisocyanate, methylcyclohexane diisocyanate,
  • TIN 4-isocyanatomethyl-1, 8-octane diisocyanate
  • decane and triisocyanate undecanediol and triisocyanate
  • dodecanedi and triisocyanates dodecanedi and triisocyanates.
  • IPDI isophorone diisocyanate
  • HDI hexamethylene diisocyanate
  • Hi 2 MDI diisocyanatodicyclohexylmethane
  • MPDI 2-methylpentane diisocyanate
  • TMDI 2,2,4-thmethylhexamethylene diisocyanate / 2,4,4-thmethylhexamethylene diisocyanate
  • NBDI norbornane diisocyanate
  • isocyanurates based on IPDI and HDI are commercially available e.g. as DESMODUR N3300 (isocyanurate from HDI, Bayer AG) and VESTANAT T1890 (isocyanurate from IPDI, Evonik-Degussa GmbH).
  • oligoisocyanates or polyisocyanates which are prepared from the abovementioned diisocyanates or polyisocyanates or mixtures thereof by linking by means of urethane, allophanate, urea, biuret, uretdione, amide, isocyanurate, carbodiimide, uretonimine , Oxadiazinetrione or iminooxadiazinedione structures.
  • Particularly suitable are isocyanurates, especially from IPDI and HDI.
  • Suitable heterocycles C2) are all nitrogen, sulfur or phosphorus-containing ring systems preferably having 5 to 7 ring atoms with at least one isocyanate-reactive hydrogen, for.
  • aziridine pyrrole, imidazole, pyrazole, triazole, azepine and indole. Preference is given to using imidazole, pyrazole and triazole.
  • alkyl-substituted heterocycles such as preferably 3,5-dimethylpyrazole.
  • Suitable polyamines or polyols C3) are all monomers, oligomers or polymers having at least two isocyanate-reactive hydrogen atoms from the group of the amino groups (NH or NH 2) and / or alcohol groups.
  • suitable examples according to the invention are ethylenediamine,
  • Trimethylolpropane propanediol, butanediol, hexanediol, polyetherdialcohols,
  • Polyetherthalkohole Polyetherdiamine and / or Polyetherthamine.
  • the reaction between C1), C2) and C3) can be carried out in conventional units, for. B. in stirred tanks, intensive mixers, intensive kneaders, static mixers or in extruders are performed, with or without the presence of solvents.
  • C1) is usually charged, brought to a suitable temperature between RT and 180 0 C and successively or simultaneously with C2) and C3), until the reaction is complete. Thereafter, if solvent is present, this either removed by distillation or filtered off. If working without solvent, the mixture is allowed to cool, if necessary, before it is ground and sieved in both cases.
  • the incorporation of the accelerator C) in the overall formulation or in a part of the overall formulation can be carried out by simple stirring, but also by dispersing in suitable dispersing equipment, optionally with the use of dispersing aids, for. B. TEGO Dispers (Evonik Degussa GmbH) additives.
  • Conventional additives D may include solvents, pigments, flow control agents,
  • Matting agent and other common accelerators z. B. urons or imidazoles.
  • the amount of these additives may vary widely depending on the application.
  • the present invention is also the use of the claimed reactive compositions z.
  • adhesives, in electrical laminates and in powder coatings are used, as well as articles containing a reactive composition of the invention.
  • Homogenized components in suitable devices eg in stirred tanks, intensive mixers, intensive kneaders, static mixers or in extruders, usually at elevated temperatures (70 - 130 0 C).
  • the cooled mixture is broken, ground and sieved.
  • composition according to the invention due to the present invention contained component C), so the accelerator, at least so reactive that after 30 minutes 140 0 C complete crosslinking has taken place (demonstrated by a flexible and chemical-resistant paint film).
  • the reactive composition can be applied in a suitable manner, for. As geräkelt, painted, strewn, sprayed, sprayed, poured, flooded or soaked.
  • the sieved powder is electrostatically charged and then sprayed onto the substrate to be coated.
  • the cure may be at elevated temperature in one or more stages, with or without pressure.
  • the curing temperature is between 70 and 220 0 C, usually between 120 and 180 0 C.
  • the curing time is between 1 minute and several hours, usually between 5 minutes and 30 minutes, depending on the reactivity and temperature.
  • compositions 1 and 2 are stable on storage (viscosity increase after 8 h at 60 ° C. not greater than 50%) b) reactivity
  • compositions 1 and 2 * were coated onto steel panels and cured at 30 min 140 0 C in a convection oven. This resulted in the following paint data:
  • MEK test Methyl ethyl ketone resistance test by rubbing with a cotton pad soaked in MEK with 1 kg of stock until the layer is dissolved (double strokes are counted)
  • compositions 1 are cured: the flexibility (Erichsentiefung> 5 mm, you. Ball shot> 10 inch * lbs) is sufficient and the chemical resistance
  • composition 2 is not cured. Due to the stickiness, it could not be tested.
  • composition 1 according to the invention is both storage-stable and sufficiently reactive.

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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)
  • Adhesives Or Adhesive Processes (AREA)
  • Paints Or Removers (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Epoxy Resins (AREA)
  • Polyurethanes Or Polyureas (AREA)

Abstract

L'invention a pour objet des formulations de résine époxyde présentant un mélange particulier de catalyseurs difficilement solubles, destiné à augmenter la réactivité.
EP10718949A 2009-07-20 2010-04-29 Catalyse de formulations de résine époxyde présentant des catalyseurs difficilement solubles Withdrawn EP2456804A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102009027825A DE102009027825A1 (de) 2009-07-20 2009-07-20 Katalyse von Epoxidharzformulierungen mit schwerlöslichen Katalysatoren
PCT/EP2010/055793 WO2011009648A1 (fr) 2009-07-20 2010-04-29 Catalyse de formulations de résine époxyde présentant des catalyseurs difficilement solubles

Publications (1)

Publication Number Publication Date
EP2456804A1 true EP2456804A1 (fr) 2012-05-30

Family

ID=42635511

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Application Number Title Priority Date Filing Date
EP10718949A Withdrawn EP2456804A1 (fr) 2009-07-20 2010-04-29 Catalyse de formulations de résine époxyde présentant des catalyseurs difficilement solubles

Country Status (13)

Country Link
US (1) US20120115988A1 (fr)
EP (1) EP2456804A1 (fr)
JP (1) JP2012533663A (fr)
KR (1) KR20120050969A (fr)
CN (1) CN102482399A (fr)
AU (1) AU2010275710B2 (fr)
BR (1) BR112012001346A2 (fr)
CA (1) CA2767927A1 (fr)
DE (1) DE102009027825A1 (fr)
MX (1) MX2012000845A (fr)
RU (1) RU2012105566A (fr)
WO (1) WO2011009648A1 (fr)
ZA (1) ZA201200388B (fr)

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JP2012193321A (ja) * 2011-03-18 2012-10-11 Furukawa Electric Co Ltd:The 放射線硬化型粘着剤組成物、それを用いたウェハ加工用粘着テープ、放射線硬化型粘着剤組成物の判定方法
ITTO20110283A1 (it) * 2011-03-29 2012-09-30 Avio Spa Formulazioni polimeriche a reologia chimicamente regolabile per la fabbricazione di preimpregnati e articoli in materiale composito
CN103666190B (zh) * 2012-09-03 2016-10-26 徐寿柏 一种水性江海船底漆及其制备方法
EP2706076B1 (fr) 2012-09-07 2014-12-17 Evonik Industries AG Compositions durcissables à base de résines époxy sans alcool benzylique
DE102012223387A1 (de) 2012-12-17 2014-06-18 Evonik Industries Ag Verwendung von substituierten Benzylalkoholen in reaktiven Epoxy-Systemen
CN104927742B (zh) * 2015-06-23 2017-05-17 上海东和胶粘剂有限公司 聚氨酯木结构胶及其制备方法
CN106543648B (zh) * 2016-12-07 2019-06-18 江苏科技大学 一种母线槽用改性环氧树脂基超耐候复合材料
US11453744B2 (en) 2019-10-15 2022-09-27 Evonik Operations Gmbh Compositions consisting of BrØnsted acids and monoamines

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AU2010275710A1 (en) 2012-03-08
KR20120050969A (ko) 2012-05-21
CA2767927A1 (fr) 2011-01-27
RU2012105566A (ru) 2013-08-27
JP2012533663A (ja) 2012-12-27
BR112012001346A2 (pt) 2016-03-15
DE102009027825A1 (de) 2011-01-27
US20120115988A1 (en) 2012-05-10
CN102482399A (zh) 2012-05-30
ZA201200388B (en) 2012-09-26
MX2012000845A (es) 2012-02-28
WO2011009648A1 (fr) 2011-01-27
AU2010275710B2 (en) 2014-05-22

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