EP2688951A1 - Utilisation d'arylalkylphénols époxydés comme diluant de résine réactif - Google Patents

Utilisation d'arylalkylphénols époxydés comme diluant de résine réactif

Info

Publication number
EP2688951A1
EP2688951A1 EP12708815.1A EP12708815A EP2688951A1 EP 2688951 A1 EP2688951 A1 EP 2688951A1 EP 12708815 A EP12708815 A EP 12708815A EP 2688951 A1 EP2688951 A1 EP 2688951A1
Authority
EP
European Patent Office
Prior art keywords
compounds
formula
mixture
compound
use according
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Withdrawn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
EP12708815.1A
Other languages
German (de)
English (en)
Inventor
Bodo Friedrich
Knut Hillner
Rolf Herzog
Peter MÜHLENBROCK
Manuela Grewing
Dirk Sichelschmidt
Martina Terhardt
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 GmbH
Rain Carbon Germany GmbH
Original Assignee
Ruetgers Germany GmbH
Momentive Specialty Chemicals 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 Ruetgers Germany GmbH, Momentive Specialty Chemicals GmbH filed Critical Ruetgers Germany GmbH
Publication of EP2688951A1 publication Critical patent/EP2688951A1/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Withdrawn legal-status Critical Current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
    • C08G59/62—Alcohols or phenols
    • C08G59/621—Phenols
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
    • C07D303/02—Compounds containing oxirane rings
    • C07D303/04—Compounds containing oxirane rings containing only hydrogen and carbon atoms in addition to the ring oxygen atoms
    • 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
    • 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
    • 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
    • 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

Definitions

  • the invention relates to the use of glycidylated mono (alkylaryl) -henols as reactive diluents for epoxy resin compositions, polymerizable compositions containing them and their use in epoxy resins.
  • Glycidylated (epoxidized) compounds are used in various compositions for a wide variety of applications. Depending on their compositions, they are used for example for composite materials, electrical laminates, adhesives, paints, electro casting resins or in the construction sector.
  • a composition intended for the abovementioned uses usually contains one or more epoxy resin components (thus based on bisphenol A and F, cycloaliphatic resins, brominated resins, phenol novolak resins), hardeners (such as base amines, Adduct hardener, Mannich base hardener, polyaminoamide and polyaminoimidazole hardeners), accelerators (such as benzyldimethylamine and 2, 4, 6-tri (N, -dimethylaminomethyl) phenol) and fillers.
  • epoxy resin components such as base amines, Adduct hardener, Mannich base hardener, polyaminoamide and polyaminoimidazole hardeners
  • accelerators such as benzyldimethylamine and 2, 4, 6-tri (N, -dimethylaminomethyl) phenol
  • Antr 1 - ⁇ reactive fillers lead to difficulties in vera: trapped in the preparation of the composition on site until application, for example, as a coating.
  • benzyl alcohol or high-boiling solvents such as styrenated phenol (mono (alkylaryl) phenol) to reduce the mixing viscosity of the composition.
  • Styrenated phenol can be used to improve the flow, to accelerate the curing reaction and to obtain better surface properties, for example in coating systems.
  • a reactive diluent serves to adjust the viscosity of the mixture and is chemically bound in the cured composition during the curing process so that, as a rule, the emission of solvents can be reduced.
  • epoxy compounds based on phenolic compounds as reactive diluents. Such include phenol, resol, bisphenol-A or p-tert. Butylphenol. These show a significantly higher reactivity than epoxy compounds based on aliphatic alcohols. They also impart high chemical resistance to the cured product but are undesirable because of their toxicological properties.
  • CH 324 686 describes the reaction of phenol with styrene and the reaction of the resulting product with a glycidyl ether in an alkaline medium to form an infusible product.
  • the object of the invention is to provide reactive diluents with high reactivity for epoxy resin compositions which do not have the disadvantages indicated above.
  • R 1 and R 2 independently of one another, denote -H, C 1-3 -alkyl, C 1-3 -alkyl and glycidyl, but R 1 and R 2 are not simultaneously glycidyl,
  • R 3 is an optionally substituted styryl of the formula
  • R 4 is a hydrogen radical or methyl
  • R 5 and R 6 is a hydrogen radical, C 1 -.3-Alk.yl, Ci- 2 -Oxalkyl as reactive diluents in epoxy resin compositions.
  • Ci-3-alkyl include methyl, ethyl, propyl and isopropyl.
  • C 1 -3 - oxalkyl include methoxy, ethoxy, propoxy and isopropoxy.
  • the invention further provides the use of a mixture of epoxidized mono (alkylaryl) phenols, i. styrenated phenols having a glycidyl radical as a reactive diluent for epoxy resin compositions.
  • This mixture contains several compounds of the following chemical formulas Ia, Ib and Ic:
  • R 4 , R s and R 6 have the meanings given above.
  • the invention further provides a composition comprising one of the aforementioned compounds or a mixture of these compounds containing at least one crosslinkable polymer.
  • composition of one or more inventive epoxy compounds as Reakti diluent despite a high steric hindrance compared to conventional aromatic diluents such as phenol, cresol or p-tert.
  • aromatic diluents such as phenol, cresol or p-tert.
  • Butyl phenol a comparable reactivity.
  • the reactivity of the reactive diluents according to the invention is higher than the aliphatic reactive diluents based on mono- or difunctional alcohols.
  • the mixture according to the invention which is used as reactive diluent preferably contains essentially the following compounds:
  • R2 0-CH 2 - CH 2 CH- and c) Ri: O- CH 2 - CH 2 CH-
  • These compounds may be present in at least 60% by weight, preferably at least 80% by weight, more preferably at least 90% by weight or at least 95% by weight in the mixture to be used according to the invention.
  • a mixture based on the sum of the masses of the compounds of the formula Ia, Ib and Ic, 30 to 60 wt .-% of Ia, 10 to 25 wt .-% of Ib and 20 to 40 wt .-% of Ic ,
  • the mixture used according to the invention can be obtained by epoxidation of styrenated phenol.
  • the preparation of styrenated phenol by reacting a phenolic component with an olefin is known and described for example in EP 0 656 384 A2. These are essentially alkylation reactions in which the vinyl group of the styrenes is added ortho or para to the hydroxyl group of the phenol. In this reaction, Friedel-Crafts Catalysts, for example acids and Lewis acids used.
  • the addition of the vinyl compound to phenols can be carried out at a molar ratio of the phenolic hydroxyl group in the phenol to the aromatic compound of 1: 1 to 1: 2.
  • Suitable aromatic vinyl compounds are, in particular, alpha-methylstyrene, styrene, o-methylstyrene, m-methylstyrene, p-methylstyrene, commercial vinyltoluene (mixture of isomers), 3,4-dimethylstyrene, 2-dimethylstyrene, 2,5-dimethylstyrene, 2,6-dimethylstyrene , o-ethylstyrene, m-ethylstyrene, p-ethylstyrene, 3,4-diethylstyrene, 2,4-diethylstyrene, 2,5-diethylstyrene, 2,6-diethylstyrene.
  • the cationically induced conversion to styrenated phenol results in a statistical distribution of 2-, 4- and 2,4-substituted phenol.
  • the monostyrrated compounds can first be separated from the distyrenated phenol by vacuum distillation. The mixture of monostyrenated compounds can then be separated by crystallization into the 2-styrenated and 4-styrenated phenol.
  • the styrenated phenol or a mixture of styrenated phenols is reacted with an oxirane compound to obtain the epoxidized compounds of this invention.
  • the phenolic OH group reacts with the oxirane compound.
  • the oxirane compound used is preferably epichlorohydrin.
  • the reaction is generally carried out in the presence of alkali metal hydroxide, for example sodium hydroxide, at elevated temperature according to the theoretical equation with elimination of common salt and water to give the glycidyl compound according to the invention in accordance with the reaction scheme shown below:
  • the mixture used according to the invention can be used as a reactive compound, even if a hydrophobicizing effect is to be achieved. This can be done, for example, in coating compositions by using the mixture according to the invention as a resin constituent or as a reactive diluent with at least one further resin constituent.
  • the mixture can be used as a modifier in the polyester synthesis, for example for reducing acid groups or alcohol groups, while at the same time increasing the hydrophobicity.
  • the mixture according to the invention can be used as a paper treatment agent without showing the known disadvantages of migration as in non-reactive phenolic components.
  • this blend can be used to make reinforced or unreinforced plastics (e.g., thermosets, thermoplastics) and elastomers.
  • reinforced or unreinforced plastics e.g., thermosets, thermoplastics
  • elastomers e.g., thermosets, thermoplastics
  • compositions which, as further component, comprise at least one crosslinkable plastic (thermopolast, Elastomer), in particular duroplastic plastic (such as polyester resin, epoxy resin, phenolic resin or melamine resin) have.
  • crosslinkable plastic thermopolast, Elastomer
  • duroplastic plastic such as polyester resin, epoxy resin, phenolic resin or melamine resin
  • the mixture according to the invention with at least one crosslinkable plastic in a ratio of 5:95 to 50:50 is present.
  • the preparation of the composition takes place in üb Licher way.
  • the mixture to be used according to the invention as a further component at least d) an epoxy resin selected from glycidyl ether based on bisphenol A, bisphenol F or novolaks, mono-, di- or polyfunctional alcohols, mono- or polyfunctional phenol len such as phenol, cresol, resorcinols, naphthols, p-tert-butylphenols, nonylphenols, cashew nut oil compounds, C 12 C14 alcohols, butanediols and / or hexanediols e) a hardener selected from aminic or acidic compounds and such Hardeners which can initiate a homopolymerization of epoxy compounds and f) optionally further additives, such as processing aids ⁇ and inorganic fillers, preferably 5 to 20 parts by weight, based on all components of the composition.
  • an epoxy resin selected from glycidyl ether based on bisphenol A, bisphenol F or novolaks, mono
  • glycidyl ethers based on bisphenol A, bisphenol F or novolaks, mono-, di- or polyfunctional alcohols, mono- or polyfunctional phenols, such as phenol, cresol resorcinols, naphthols, p-tert.
  • Butylphenols, nonylphenols, cashew nut oil compounds, C 2 -C 4 -alcohols, butanediol and / or Hexanediol as further component has the advantage that the composition is crystallization resistant and storable.
  • the viscosity of this composition according to the invention can be adjusted in an appropriate range for the application.
  • Usual hardeners for Bpoxide can be used.
  • Typical representatives of the amine hardeners are compounds with one, two or more free amine hydrogens. These may have cyclic, aliphatic or aromatic linkages or polyether groups.
  • Typical representatives of this hardener class are amines such as isophoronediamine, xylylenediamine, trimethylene-hexamethylenediamine, polyetheramines.
  • suitable hardeners according to the invention are so-called acidic hardeners based on organic acids such as phthalic anhydride, hexahydrophthalic anhydride, methylhydrophthalic anhydride and other compounds of this class.
  • latent systems which are applied via radiation curing and associated ionic hardening or by thermal curing ("latent 1-component system"). Preferred in the sense of the invention are amine hardeners for the range of curing
  • adduct hardeners based on bisphenol A diglycidyl ether and isophoronediamine, which are further modified by the use of benzyl alcohol, accelerators and other additives to improve the processing properties or end uses.
  • the mixing ratio with the epoxide-reactive components results from the stoichiometric conversion.
  • the exact mixing ratio depends on the application and may include both a substoichiometric and a superstoichiometric implementation.
  • the epoxy resin composition of the present invention is prepared by mixing the individual components according to known methods. By mixing the components at a higher temperature, for example at 60 ° to 80 ° C, the mixing and filling process can be accelerated.
  • higher or lower proportions can also be used.
  • the mixture according to the invention can be used for the production of thermosetting products.
  • coatings or even shaped bodies are conceivable.
  • the mixture according to the invention is used for coatings, in particular for self-leveling coatings.
  • coatings for industrial floors, paints, adhesives or electrical laminates would be conceivable.
  • the use according to the invention thus takes place preferably for the treatment of paper, for the production of cured polymer products, for the production of coatings, for the production of reinforced and unreinforced plastics, elastomers and moldings.
  • the stirrer is switched off and after a Absitzezeit of 30 minutes, the lower aqueous phase is drained.
  • the remaining organic phase in the reaction vessel is diluted with a further 200 g of epichlorohydrin and washed with 300 g of water, with a phase inversion takes place.
  • the organic phase is then distilled off under reduced pressure up to a temperature of 120 ° C and freed from traces of volatiles by steam distillation in vacuo.
  • the distillate contains epichlorohydrin, isopropanol, water and higher boiling impurities at a concentration of less than 1% and can be used for subsequent production.
  • the distillation residue is taken up in 248 g of toluene, heated to 75 ° C and treated with 50% sodium hydroxide solution (MV 1: 2.5 - hydrolyzable chlorine: sodium hydroxide solution) within 30 minutes. Beforehand, the same amount of water is added. The reaction time with stirring is then 1 hour. 330 g of toluene are added for dilution. The stirrer is switched off and after a settling time of 10 minutes, the aqueous phase is separated off. The organic solution is washed several times with water until neutral.
  • the toluene and remaining traces of volatiles are distilled off in vacuo to 125 ° C.
  • the epoxide compound obtained as the distillation residue is purified by a pressure filter of organic and inorganic solid impurities.
  • the yield, based on the precursor, is 95%.
  • the glycidated "styrenated phenol" (B) produced in Example 1 is used for the preparation of epoxy resin mixtures.
  • the bisphenol A diglycidyl ether is introduced into the mixing unit and the styrenated product (A) or the product (B) according to the invention is added with stirring.
  • the temperature during the stirring is kept between 65 ° C and 70 ° C.
  • This composition is optionally added after storage of the hardener in the indicated concentration (Table 1).
  • a floor coating primary or self-leveling floor coating
  • the properties of compositions containing the product (A) (styrenated phenol) are compared with compositions containing the product (B) of the invention.
  • the coating composition is applied with a doctor blade to a glass plate in a layer thickness of 200 ⁇ m. After one hour, the glass plate is weighed. The glass plate is then stored for 96 hours at room temperature and then for two hours at 100 ° C in a drying oven. Then the weight is determined and the difference the two weight measurements determined the relative weight loss.
  • Ci2-ci4 glycidyl ether 10
  • Adduct hardener based on bisphenol 54 53 A diglycidyl ether and isophoronediamine

Abstract

L'invention concerne des mono (alkylaryl) phénols (phénols styrolisés) glycidylés ou leurs mélanges qui conviennent pour être utilisés comme diluant réactif ou participant à la réaction lors de la production de résines époxydes et présentent la structure montrée ci-après de la formule générale (I) dans laquelle R1 et R2 signifient indépendamment l'un de l'autre - H, de l'alkyle en C1-3, de l'oxalkyle en C1-3 et du glycidyle, mais R1 et R2 en sont pas simultanément du glycidyle, R3 est un styryle éventuellement substitué de la formule, R4 est un reste hydrogène ou méthyle et R5 et R6 sont respectivement un reste hydrogène, de l'alkyle en C1-3, de l'oxalkyle en C1-2.
EP12708815.1A 2011-03-25 2012-03-07 Utilisation d'arylalkylphénols époxydés comme diluant de résine réactif Withdrawn EP2688951A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102011015193A DE102011015193A1 (de) 2011-03-25 2011-03-25 Epoxidierte Arylalkylphenole
PCT/EP2012/053890 WO2012130570A1 (fr) 2011-03-25 2012-03-07 Utilisation d'arylalkylphénols époxydés comme diluant de résine réactif

Publications (1)

Publication Number Publication Date
EP2688951A1 true EP2688951A1 (fr) 2014-01-29

Family

ID=45833396

Family Applications (1)

Application Number Title Priority Date Filing Date
EP12708815.1A Withdrawn EP2688951A1 (fr) 2011-03-25 2012-03-07 Utilisation d'arylalkylphénols époxydés comme diluant de résine réactif

Country Status (7)

Country Link
US (1) US20140179890A1 (fr)
EP (1) EP2688951A1 (fr)
JP (1) JP2014515045A (fr)
KR (1) KR20140041470A (fr)
CN (1) CN103459482A (fr)
DE (1) DE102011015193A1 (fr)
WO (1) WO2012130570A1 (fr)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2014067095A1 (fr) * 2012-10-31 2014-05-08 Dow Global Technologies Llc Compositions pouvant durcir
ES2615901T3 (es) 2012-12-11 2017-06-08 Fischerwerke Gmbh & Co. Kg Masa a base de epoxi para finalidades de fijación, su uso y el uso de determinados componentes
CA2942354A1 (fr) * 2015-10-15 2017-04-15 Dow Global Technologies Llc Ether de monoglycidyle tristyryphenol
WO2023171572A1 (fr) * 2022-03-09 2023-09-14 株式会社Adeka Composition de résine époxy de type monobloc

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NL95570C (fr) * 1953-05-01
US4102862A (en) * 1976-03-31 1978-07-25 Kenrich Petrochemicals, Inc. Application of cumylphenol and derivatives thereof in plastic compositions
CA1153770A (fr) * 1978-07-20 1983-09-13 Salvatore J. Monte Derives du cumylphenol
US4365103A (en) * 1981-12-04 1982-12-21 The Dow Chemical Company Process for the preparation of bis(1-phenylethenyl) compounds
JPS6028422A (ja) * 1983-07-26 1985-02-13 Mitsubishi Electric Corp 低粘度エポキシ含浸樹脂の製造方法
TW289024B (fr) 1993-11-02 1996-10-21 Hoechst Ag

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO2012130570A1 *

Also Published As

Publication number Publication date
WO2012130570A1 (fr) 2012-10-04
DE102011015193A1 (de) 2012-09-27
CN103459482A (zh) 2013-12-18
JP2014515045A (ja) 2014-06-26
US20140179890A1 (en) 2014-06-26
KR20140041470A (ko) 2014-04-04

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