Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
  • C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
  • C07C323/24—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
  • C07C323/25—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
• • 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
  • C08G59/50—Amines
  • C08G59/56—Amines together with other curing agents
• • 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
  • C08G59/66—Mercaptans

Definitions

• the present invention relates to polymer captolyamines, a process for their preparation, epoxy resin compositions containing such polymer captolyamines and the use of these compositions.
• the object of the present invention was to provide curing agents for epoxy resins which provide cured products with improved chemical resistance.
• the present invention relates to compounds of the formula Ia or Ib,
• E is an (m + 1) -valent aliphatic, cycloaliphatic, araliphatic or represents aromatic radical and m is an integer from 0 to 3
• X represents -O-, -COO-, or -CHR 4 -, where R 4 and R 3 together form an ethylene group
• Ri and R 2 independently of one another denote hydrogen or methyl
• R 3 represents hydrogen or R 3 and R 4 together form an ethylene group
• R 5 represents a monovalent aliphatic, cycloaliphatic, araliphatic or aromatic radical.
• A can in principle stand for any mono- to hexavalent radical of an epoxide. Preferred are di-, tri- and tetravalent radicals
• ahphatic residues are ethylene, propylene, tetramethylene, hexamethylene, poly (oxyethylene), poly (oxypropylene), poly (oxytetramethylene), 2-methyl-1, 5-pentanedioyl, 2,2,4-tr ⁇ methyl-1, 6- hexanedyl, 2,4,4-trimethyl-1, 6-hexanedyl and the residues of aliphatic alcohols after removal of the OH groups, such as, for example, the residues of trimethylolpropane, pentaerythritol and dipentarerythnite
• Cycloaliphatic radicals are, for example, cyclopentyl, cyclohexyl, 1, 3-cyclopentylene, 4-methyl-1, 3-cyclopentylene, 1, 2-cyclohexylene, 1, 3-cyclohexylene, 1, 4-cyclohexylene, 4-methyl-1, 3 -cyclohexylene, 2,5-norbornanedyl, 2,6-norbomanedyl, 7,7-dimethyl-2,5-norbomanedyl, 7,7-dimethyl-2,6-norbornanedyl, cyclohexane-1,3-methylene, cyclohexane-1 , 4-dimethylene, 3-methylene-3,5,5-tmethylcyclohexylene (isophorone), norbornane-2,5-dimethylene, norboman-2,6-dimethylene, 7,7-dimethylnorbornane-2,5-dimethyl and 7, 7-dimethylnorb
• Suitable arahmic residues are, for example, benzyl, the residues of 1, 2-, 1, 3- and 1, 4-B ⁇ s- (hydroxymethyl) benzene, the residues of 1, 2,3-, 1, 2,4-, 1, 2,5- and 1,3,5-T ⁇ s- (hydroxymethyl) benzene and the residues of B ⁇ s- (hydroxymethyl) naphthal ⁇ n.
• aromatic residues are phenyl, naphthyl, the residues of bisphenols such as bisphenol A, bisphenol F and dihydroxybiphenyl, and the residues of phenol and cresol novolaks
• X is -O- and A is a divalent radical of a bisphenol or a cycloaliphatic diol and the radical is one Phenol or cresol novolak, for the di- to tetravalent radical of an isocyanate-polyol adduct or for the tri- to hexavalent radical of a tri- to hexafunctional aliphatic polyol.
• R 5 in the formulas Ia and Ib is preferably unsubstituted or substituted by one or more amino groups, hydroxyl groups, C 1 -C 8 -alkoxy groups or halogen atoms, CrC 20 alkyl, C 5 -C 12 cycloalkyl, C 6 -C 10 aryl or C 7 -C 12 aralkyl.
• Suitable alkyl groups as R 5 are, for example, methyl, ethyl, isopropyl, n-propyl, n-butyl, isobutyl, sec-butyl, tert-butyl and the various isomeric pentyl, hexyl, heptyl, octyl and nonyl -, Decyl, Undecyl, Dodecyl, Tridecyl, Tetradecyl, Pentadecyl, Hexadecyl, Heptadecyl and Octadecyl groups.
• Cycloalkyl is preferably C 5 -C 8 cycloalkyl, in particular C 5 or C 6 cycloalkyl. Some examples are cyclopentyl, methylcyclopentyl, cyclohexyl, cycloheptyl and cyclooctyl.
• Aralkyl preferably contains 7 to 12 carbon atoms and particularly preferably 7 to 10 carbon atoms.
• it can be benzyl, phenethyl, 3-phenylpropyl, ⁇ -methylbenzyl, 4-phenylbutyl and ⁇ , ⁇ -dimethylbenzyl.
• Aryl groups are, for example, phenyl, tolyl, mesityl, isityl, naphthyl and anthryl.
• R 5 is C 2 -C 0 -alkyl, C 2 -C 10 - aminoalkyl, phenyl, benzyl, cyclohexyl or a radical of the formula H 2 NZ-CH 2 -NH- , wherein Z represents a divalent cycloaliphatic, araliphatic or aromatic radical or a radical of the formula - (CH 2 CH 2 NH) k -CH 2 -, wherein k represents 2 or 3.
• Suitable Z radicals are, for example, the divalent radicals given above for A.
• R ⁇ is n-butyl, n-octyl, cyclohexyl, benzyl, 2-aminoethyl, 4- (aminomethyl) pentyl, 5-amino-2-methylpentyl, 3-dimethylaminopropyl, 3 -Methylaminopropyl, 4-aminocyclohexyl or for a residue of
• the compounds of the formula Ia can be prepared by known methods from the epoxy compounds of the formula Ila, in which A, X, Rj, R 3 and n have the meaning given above:
• the epoxide compound of the formula IIIa is converted into the purple episulfide of the formula by reaction with thiourea or an alkali metal or ammonium thiocyanate, preferably potassium thiocyanate
• Thiourea or thiocyanate is expediently used in an amount such that 0.8 to 1.2 equivalents of sulfur are accounted for by one epoxide equivalent.
• reaction can be carried out in aprotic or protic organic solvents or
• Alcohols such as methanol or are preferred
• Cosolvents such as ethers or carboxylic acids can accelerate the reaction.
• the reaction can be carried out either at room temperature or at elevated temperature; the preferred reaction temperature is between 60 and 100 ° C.
• the episulfide of the formula purple can be isolated by removing the by-products by means of filtration, extraction, phase separation and then evaporating the
• the episulfide of the formula purple is then dissolved in an aprotic or protic organic solvent and reacted with the amine R 5 -NH-R 2 under inert gas (argon or nitrogen).
• the amount of the amine is preferably chosen so that 1 -10 NH groups are accounted for by one episulfide group.
• Preferred solvents are alcohols (for example methanol, ethanol, t-butanol) and aromatic hydrocarbons, such as toluene or xylene.
• the amine R, -NH 2 is also preferably used as a solution in one of the organic solvents mentioned above.
• the reaction is expediently carried out at an elevated temperature, preferably at 40 ° C.-120 ° C.
• the compounds of the formula Ia according to the invention can be isolated by distilling off the solvent under reduced pressure.
• the excess amine R 5 -NH-R 2 can then also be removed by distillation at elevated temperature.
• the amine R 5 -NH-R 2 is used as a co-hardener; in this case a separation of the product of the formula Ia and the amine R 5 -NH-R 2 is not necessary, but the reaction product can be used as a hardener for epoxy resins without further work-up. This procedure is particularly recommended when using di- or polyamines.
• the present invention thus also relates to a process for the preparation of compounds of the formula Ia by reaction of a compound of the formula IIa wherein A, X, R ( R 3 and n have the meaning given above, with thiourea or a thiocyanate and subsequent reaction of the episulfide thus obtained with an amine of the formula R 5 -NH-R 2 , wherein R 5 and R 2 have the above have given meaning.
• the compounds of the formula Ib can be prepared analogously from the corresponding epoxy compounds of the formula IIb.
• Another object of the invention is therefore a process for the preparation of compounds of the formula Ib by reaction of a compound of the formula IIb
• episulfides can also be synthesized from the corresponding epoxides by reaction with triphenylphosphine sulfide.
• episulfides can be prepared directly from the corresponding alkenes by known methods, for example by reaction with m-chloroperbenzoic acid and subsequent reaction with thiourea in the presence of H 2 SO 4 , by reaction with propylene sulfide in the presence of rhodium catalysts and by reaction with (diethoxyphosphoryl ) sulfenyl chloride, (diethoxythiophosphoryl) sulfenyl bromide, thiobenzophenone S-oxide or bis (trimethylsilyl) sulfide.
• the polymer captolyamines according to the invention are particularly suitable as hardeners for epoxy resins.
• Another object of the invention is a composition containing
• Component A for the preparation of the compositions according to the invention are the epoxy resins customary in epoxy resin technology.
• Examples of epoxy resins are:
• polyglycidyl and poly ( ⁇ -methylglycidyl) esters obtainable by reacting a compound having at least two carboxyl groups in the molecule and epichlorohydrin or ⁇ -methylepichlorohydrin. The reaction is conveniently carried out in the presence of bases.
• Aliphatic polycarboxylic acids can be used as a compound having at least two carboxyl groups in the molecule.
• examples of such polycarboxylic acids are oxalic acid, succinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid or dimerized or trimerized linoleic acid.
• cycloaliphatic polycarboxylic acids can also be used, such as, for example, tetrahydrophthalic acid, 4-methyltetrahydrophthalic acid, hexahydrophthalic acid or 4-methylhexahydrophthalic acid.
• Aromatic polycarboxylic acids such as phthalic acid, isophthalic acid or terephthalic acid can also be used.
• Polyglycidyl or poly ( ⁇ -methylglycidyl) ether obtainable by reacting a compound with at least two free alcoholic hydroxyl groups and / or phenolic hydroxyl groups with epichlorohydrin or ⁇ -methylepichlorohydrin under alkaline conditions or in the presence of an acidic catalyst with subsequent alkali treatment.
• the glycidyl ethers of this type are derived, for example, from acyclic alcohols, e.g. of ethylene glycol, diethylene glycol or higher poly (oxyethylene) glycols, propane-1, 2-diol or poly- (oxypropylene) -glycols, propane-1, 3-diol, butane-1, 4-diol, poly- (oxytetramethylene) - glycols, pentane-1, 5-diol, hexane-1, 6-diol, hexane-2,4,6-triol, glycerin, 1, 1, 1 -trimethylolpropane, pentaerythritol, sorbitol, and of polyepichlorohydrins.
• acyclic alcohols e.g. of ethylene glycol, diethylene glycol or higher poly (oxyethylene) glycols, propane-1, 2-diol or poly- (oxypropylene) -gly
• glycidyl ethers of this type are derived from cycloaliphatic alcohols, such as 1,4-cyclohexanedimethanol, bis (4-hydroxycyclohexyl) methane or 2,2-bis (4-hydroxycyclohexyl) propane, or from alcohols which are aromatic Contain groups and / or further functional groups, such as N, N-bis (2-hydroxyethyl) aniline or p, p'-bis (2-hydroxyethylamino) diphenylmethane.
• cycloaliphatic alcohols such as 1,4-cyclohexanedimethanol, bis (4-hydroxycyclohexyl) methane or 2,2-bis (4-hydroxycyclohexyl) propane, or from alcohols which are aromatic Contain groups and / or further functional groups, such as N, N-bis (2-hydroxyethyl) aniline or p, p'-bis (2-hydroxyethylamino) diphenylmethane.
• the glycidyl ethers can also be used on mononuclear phenols, such as, for example, resorcinol or hydroquinone, or on multinuclear phenols, such as, for example, bis- (4-hydroxyphenyl) methane, 4,4'-dihydroxybiphenyl, bis- (4-hydroxyphenyl) sulfone, 1, 1, 2,2-tetrakis (4-hydroxyphenyl) ethane, 2,2-bis (4-hydroxyphenyl) propane or 2,2-bis (3,5-dibromo-4-hydroxyphenyl) propane, based.
• mononuclear phenols such as, for example, resorcinol or hydroquinone
• multinuclear phenols such as, for example, bis- (4-hydroxyphenyl) methane, 4,4'-dihydroxybiphenyl, bis- (4-hydroxyphenyl) sulfone, 1, 1, 2,2-tetrakis (4-hydroxyphen
• Suitable hydroxy compounds for the production of glycidyl ethers are novolaks, obtainable by condensation of aldehydes, such as formaldehyde, acetaldehyde, chloral or furfuraldehyde, with phenols or bisphenols which are unsubstituted or substituted with chlorine atoms or d-Cg-alkyl groups, such as phenol, 4- Chlorophenol, 2-methylphenol or 4-tert-butylphenol.
• Poly (N-glycidyl) compounds obtainable by dehydrochlorination of the reaction products of epichlorohydins with amines which contain at least two hydrogen amine atoms. These amines are, for example, aniline, n-butylamine, B ⁇ s- (4-aminophenyl) methane, m-xylylenediamine or bis (4-methylaminophenyl) methane
• poly (N-glycidyl) compounds also include glycidyhsocyanurate, N, N'-D'-glycidyl derivative of cycloalkylene ureas, such as ethylene urea or 1,3-propylene urea, and diglycidyl derivative of hydantoins, such as 5,5-dimethyl
• Poly (S-glycidyl) compounds for example di-S-glycidyl derivatives, which are derived from dithiols, such as, for example, ethane-1,2-eththol or bis (4-mercaptomethylphenyl) ether.
• Cycloahphatic epoxy resins such as, for example, B ⁇ s- (2,3-epoxycyclopentyl) ether, 2,3-Epoxycyclopentylglyc ⁇ dylether, 1, 2-B ⁇ s- (2,3-epoxycyclopentyloxy) ethane or 3,4-Epoxycyclohexylmethyl-3 ', 4'-epoxycyclohexane.
• epoxy resins can also be used in which the 1,2-epoxy groups are bonded to different heteroatoms or functional groups; these compounds include, for example, the N, N, 0-trlyglycidyl dervate of 4-aminophenol, the glycidyl ether-glycidyl ester of salicylic acid, N-glycidyl-N '- (2-glycidyloxypropyl) - 5,5-dimethylhydantoin or 2-glycidyloxy-1 3-b ⁇ s- (5,5-dimethyl-1-glycidylhydanto ⁇ n-3-yl) propane
• a liquid or solid polyglycidyl ether or ester in particular a liquid or solid bisphenol diglycidyl ether or a solid or liquid diglycidyl ester of a cycloaliphatic or aromatic dicarboxylic acid, or a cyclophatic epoxy resin is preferably used to prepare the epoxy resin compositions according to the invention. Mixtures of epoxy resins can also be used
• Suitable solid polyglycidyl ethers and esters are compounds with melting points above room temperature up to about 250 ° C.
• the melting points of the solid are preferably Connections in the range from 50 to 150 ° C.
• Such solid compounds are known and some are commercially available.
• the advancement products obtained by pre-extending liquid polyglycidyl ether and esters can also be used as solid polyglycidyl ethers and esters.
• the epoxy resin compositions according to the invention contain a liquid polyglycidyl ether or ester.
• component A is bisphenol A diglycidyl ether, bisphenol F diglycidyl ether, mixtures of bisphenol A diglycidyl ether and bisphenol F diglycidyl ether, epoxy urethanes, aliphatic epoxy resins such as trimethylol propane triglycidyl ether and cycloaliphatic epoxy resins such as hexahyde ether.
• polymer captolyamines according to the invention can advantageously be used in combination with other epoxy hardeners, in particular with the customary amine hardeners.
• Another object of the invention therefore forms a composition containing
• Suitable polyamines C are aliphatic, cycloaliphatic, aromatic and heterocyclic amines, such as bis (4-aminophenyl) methane, aniline-formaldehyde resins,
• Diaminocyclohexane bis (4-aminocyclohexyl) methane, bis (4-amino-3-methylcyclohexyl) methane, 2,2-bis (4-aminocyclohexyl) propane and 3-aminomethyl
• Polyaminoamides such as those made from aliphatic polyamines and dimerized or trimerized fatty acids.
• Suitable amines (C) are also those known as Jeffamines
• polyamines (C) are 1, 14-dimin-4.1, 1-dimoxetretradecane, dipropylentiamine, 2-methyl-1, 5-pentanediamine, N, N'-cyclochexyl-1, 6-hexanediamine, N, N'- Dimethyl-1, 3-diminopropane, N, N'-dimethyl-1, 3-diminopropane, N, N-dimethyl-1, 3-diminopropane, secondary polyoxypropylenediamines and -t ⁇ amines, 2,5-diamino-2,5- dimethylhexane, B ⁇ s- (am ⁇ no-methyl) t ⁇ cyclopentad ⁇ en, m-aminobenzylamine, 1, 8-D ⁇ am ⁇ no-p-menthan, bis- (4-am ⁇ no-3,5-dimethylcyclohexyl) methane, 1, 3-B ⁇ s (am ⁇ nomethyl) cyclohexane
• Preferred component A of the mixtures of substances according to the invention are cycloaliphatic and aliphatic nurses, in particular the nurses of the formulas R 5 -NH-R 2 and E- (NHR 2 ) m + 1 used to prepare the polymer captolyamines according to the invention
• the quantitative ratio of components A and B and optionally C can vary within wide ranges in the compositions according to the invention.
• the optimal ratio depends, among other things, on the amine type and can easily be determined by a specialist.
• Components B and optionally C are preferably used in amounts such that the sum of the amine and mercaptan equivalents 0.5 to 2.0, particularly preferably 0.8 to 1.5 and particularly preferably 0.9 to 1.2 equivalents, based on an epoxy equivalent
• compositions of the invention may optionally contain accelerators such as tertiary ames or imidazoles
• the hardenable mixtures can also contain toughness agents, such as, for example, core / shell polymers or the graft polymers containing elastomers or elastomers known to the person skilled in the art as suitable rubber toughness agents.
• suitable toughness agents are described, for example, in EP-A-449 776
• the hardenable mixtures can contain fillers, such as, for example, metal powder, wood powder, glass powder, glass balls, semimetal and metal oxides, such as, for example, SiO 2 (aerosils, quartz, quartz powder, quartz powder), corundum and titanium oxide, Semimetal and metal nitrides, such as silicon nitride, boron nitride and aluminum nitride, semimetal and metal carbides (SiC), metal carbonates (dolomite, chalk, CaCO 3 ), metal sulfates (barite, gypsum), stone powder and natural or synthetic minerals mainly from the silicate range, such as zeolites (especially molecular sieves) talc, mica, kaolin, woolastonite, bentonite and others.
• SiO 2 as, for example, SiO 2 (aerosils, quartz, quartz powder, quartz powder), corundum and titanium oxide
• Semimetal and metal nitrides such as silicon nitrid
• the curable mixtures may contain other conventional additives, such as e.g. Antioxidants, light stabilizers, plasticizers, dyes, pigments, thixotropic agents, toughness improvers, defoamers, antistatic agents, lubricants and mold release agents.
• additives such as e.g. Antioxidants, light stabilizers, plasticizers, dyes, pigments, thixotropic agents, toughness improvers, defoamers, antistatic agents, lubricants and mold release agents.
• the epoxy resin compositions according to the invention are cured to give moldings, coatings or the like in the manner customary for epoxy resin technology, as described, for example, in the "Handbook of Epoxy Resins", 1967 by H. Lee and K. Neville.
• the curable mixtures have only a slight tendency to carbonate (cloudiness).
• the hardened products are characterized by a surprisingly high chemical resistance and weather resistance.
• crosslinked products obtainable by curing a composition according to the invention represent a further subject of the invention.
• compositions according to the invention are outstandingly suitable as coating compositions, adhesives, binders for composite materials or cast resin for the production of moldings.
• the polyepoxide of formula II is dissolved in 0.5 to 5 times the amount of solvent and under nitrogen with thiourea or alkali metal or ammonium thiocyanate (0.8-1.2 equivalents of sulfur per epoxy equivalent) as long as at 60-100 ° C. stirred until the epoxy content has dropped to almost zero.
• the polyepisulfide is dissolved in 0.5 to 5 times the amount of solvent and combined under nitrogen with vigorous stirring with the amine, which is also dissolved in 0.5 to 5 times the amount of solvent.
• the amount of amine is chosen so that 1 -10 NH 2 groups are accounted for by one episulfide group.
• the solvent is distilled off under reduced pressure.
• the excess amine reagent is removed by vacuum distillation at elevated temperature. In one embodiment of the invention, the removal of the excess amine is dispensed with, and the mixture of the amine RN ⁇ and the polymer captolyamine of the formula I is used as a hardener for epoxy resins.
• Epoxides of formula II polymer captolyamines according to the invention prepared (Examples 1.1 -
• IPD isophoronediamine
• MXDA meta-xylylenediamine
• DYTEK-A 1,5-diamino-2-methylpentane
• NBDA isomer mixture of 2,5- and 2,6-bis (aminomethyl) norbornane
• EDA ethylenediamine epoxide 1: liquid bisphenol A-diglycidyl ether with an epoxide content of 5.25- 5.4 val / kg
• epoxide 2 liquid mixture of bisphenol A diglycidyl ether and bisphenol F diglycidyl ether with an epoxide content of 5.5-5.8 val / kg
• Epoxy 3 1, 4-bis (hydroxymethyl) cyclohexane diglycidyl ether epoxy 4 epoxyphenol novolak with an epoxy content of 5.6-5.8 val / kg epoxy 5 diglycidyl ether of hydrogenated bisphenol A epoxy 6 tetraglycidyl ether of the formula
• Epoxy 7 bisphenol A di ( ⁇ -methylglycidyl) ether
• Epoxy 8 trimethylolpropane triglycidyl ether
• Epoxide 9 hexahydrophthalic acid diglycidyl ester (epoxy number: 5.6-6.2 val / kg)
• Epoxy 10 phenylglycidyl ether
• the mixture is spread on a glass or steel plate using a doctor blade (layer thickness:
• the cured coatings show the properties given in Table 2.
• Example 11 Polymercaptolyamine from Example I.5 mixed. The mixture is processed and cured as indicated in Example 11.1.
• the polymer captolyamine prepared according to Example I.26 is mixed with the epoxy resins and other additives shown in Table 4 and cured.
• the specified value is the product of the weight of the stamp in kg and the test height in cm, at which no damage to the coating can be determined. In the case of reverse impact, the stamp is dropped onto the side facing away from the coating.

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• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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