WO1996028490A1 - Composition refractaire a base de resine epoxy - Google Patents

Composition refractaire a base de resine epoxy Download PDF

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Publication number
WO1996028490A1
WO1996028490A1 PCT/JP1996/000621 JP9600621W WO9628490A1 WO 1996028490 A1 WO1996028490 A1 WO 1996028490A1 JP 9600621 W JP9600621 W JP 9600621W WO 9628490 A1 WO9628490 A1 WO 9628490A1
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WO
WIPO (PCT)
Prior art keywords
epoxy
group
formula
triazine
epoxy compound
Prior art date
Application number
PCT/JP1996/000621
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English (en)
Japanese (ja)
Inventor
Satoru Miyake
Kenichi Osawa
Toshinari Koda
Motohiko Hidaka
Norio Tanaka
Kiyohisa Takahashi
Original Assignee
Nissan Chemical Industries, Ltd.
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 Nissan Chemical Industries, Ltd. filed Critical Nissan Chemical Industries, Ltd.
Priority to AU49534/96A priority Critical patent/AU4953496A/en
Publication of WO1996028490A1 publication Critical patent/WO1996028490A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/40—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
    • C08G59/5046—Amines heterocyclic
    • C08G59/5053—Amines heterocyclic containing only nitrogen as a heteroatom
    • C08G59/508—Amines heterocyclic containing only nitrogen as a heteroatom having three nitrogen atoms in the ring
    • C08G59/5086—Triazines; Melamines; Guanamines
    • 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

Definitions

  • thermosetting epoxy composition of the present invention is useful for improving the ifi properties of epoxy adhesives, paints, casting materials, laminate materials, and the like.
  • N-substituted melamine as a near-amine curing agent to an epoxy compound to improve workability such as pot life after the compounding.
  • an epoxy resin compound containing a substituted melamine described in Japanese Patent Application Laid-Open No. 56-72019 is disclosed in Japanese Patent Application Laid-Open No. 60-20211.
  • Epoxy resin containing the substituted melamine and the novolak-type phenol resin described in the above Fatty fflfig products are disclosed.
  • Recent development trends include improvement of ilii i properties, improvement of flexibility, and improvement of workability such as pot life after compounding, and various combinations of epoxy compounds and curing agents can be used according to the purpose. is there.
  • the combination of aliphatic amines, which originally have poor f f properties, with epoxy compounds designed to increase WH3 ⁇ 4 properties has practicality on the S surface and extremely high properties. The power to do the purpose, the power to be very difficult. And it is extremely difficult to select an appropriate curing agent that is easy to handle.
  • the epoxy compounds such as tetraglycidylxylylenediamine, tetraglycidyldiaminodiphenylmethane, and tetrakis (4-hydroxyphenyl) ethanetetraglycidyl ether mentioned above can be used in an acid anhydride curing system or a diaminediphenylsulfone curing system such as diaminodiphenylsulfone.
  • each combination with such hardeners has the following specific problems:
  • the acid anhydride itself is vulnerable to moisture absorption and is hydrolyzed to a dicarboxylic acid, so that curing failure occurs in an atmosphere having ⁇ S during curing. For this reason special consideration is given to the preservation method after blending with the eboxy compound, and the field of use is also limited;
  • diaminodifluorosulfone In the diaminodifluorosulfone hard-dyeing system, diaminodifluorosulfone itself has a high viscosity and its solubility in epoxy compounds is not so high, so it is dissolved by adding organic ⁇ HJ and distilled off. This is an ingenuity to cure while curing, and there is a problem in workability when it is not desired to mix an organic solvent.
  • N-substituted melamine having a near-triazine skeleton is used as a curing agent for epoxy resins to improve storage stability and workability.
  • the epoxy resin composition containing the N-substituted melamine and the novolac phenolic resin described in No. 0-202117 ⁇ IS has the purpose of improving the workability such as improving the bot life after the compounding, but the proper epoxy resin The ugliness of the cured product is not sufficient, because no spleen is used and the spleen is incorrect.
  • An object of the present invention is to provide an i®-epoxy compound which can be easily handled and become an extremely heat-resistant epoxy resin by thermosetting, and an iti-epoxy resin obtained by thermosetting the epoxy resin. They try to do things.
  • the present invention relates to one or more trifunctional epoxy compounds having a molecular structure in which the positions of the three epoxy groups are symmetrical, and the formula (I)
  • R 1 to R e are each independently H, alkyl groups of d-, hydroxycarboxylic alkyl C 4 -8 cycloalkyl group, cycloalkyl methylate the C 6 -0 C represents a methylcycloalkyl group of the following formula, provided that 3 to 5 of R 1 to R 6 are H, or R 6 and R e together form one (CH 2 ) 4-7 ⁇ Or one CH 2 CH 2 -0-CH 2 CH 2 may be formed. )
  • thermosetting epoxy resin containing one or more of N-substituted melamines represented by the following: active hydrogen of 1-amino group and Z or secondary amino group in N-substituted melamine;
  • the amount is 0.1 to 0.7 equivalent per equivalent of epoxy group of the trifunctional epoxy compound, and the heat resistance obtained by converting the curable epoxy compound and the thermosetting epoxy compound. It relates to the epoxy resin material.
  • Examples of the trifunctional epoxy compound used in the present invention which has a molecular structure in which the positions of the three epoxy groups are symmetric, include 1,3,5-tri (glycidyloxy) benzene and 1,3,5-trimesic acid triglyceride.
  • Substituted triglycidyl isocyanurate shown in Fig. 3 is a trifunctional epoxidation with three woven groups having a weaving structure ⁇ ! Any of these may be used, and these may be used alone or as a mixture. Among them, the formula [ ⁇ ]
  • the primary amino group and the ⁇ or secondary amino group represented by the formula [I] have an active hydrogen number of 3 to 5, and have the following various functional groups.
  • the number of alkyl groups is 1 to 18 and may be linear or branched. More preferably, the number of alkyl groups is 1 to 12.
  • the number of cycloalkyl groups is preferably from 4 to 8, more preferably a cyclopentyl group or a cyclohexyl group.
  • N-substituted melamines may be used alone or as a mixture.
  • the N-substituted melamine used in the present invention can be easily obtained by a method similar to a conventionally known synthesis method. For example:
  • 1,3,5-Triazine derivative and periodic table No. VII described in Japanese Patent Application No. 6-280370 are reacted with alcohol in the presence of catalyst VI11 and hydrogen-containing gas; and ,
  • It may be manufactured by any of the above or other known methods.However, when used in the electronic field, there is little hydrolyzable chlorine remaining in N-substituted melamine.
  • N-substituted melamine examples include 2,4-bis (amino) — 6— (2-hydroxyshethyl) amino-1,3,5-triazine, 2,4-bis (amino) -1,6-butylamino — 1, 3, 5—triazine, 2,4-bis (amino) -1-6-cyclohexylamino-1,3,5-triazine, 2,4-bis (amino) — 6—dodecylamino-1,3 , 5—triazine, 2,4-bis (amino) — 6-stearylamino-1,3,5-triazine, 2,4-bis (amino) -16_methylamino1,3,5-triazine, 2, 4-bis (amino) -1-6-dibutylamino-1,3,5-triazine, 2,4-bis (amino) -1-6-dinonylamino-1,3,5-triazine, 2,4-bis (
  • the number of substituents of the cycloalkylmethyl group or the methylcycloalkyl group is preferably from 5 to 9, and more preferably from 6 to 7.
  • the number of cycloalkyl groups is preferably from 4 to 8, more preferably from 5 to 6.
  • the number of alkylene groups is preferably 4 to 7, and more preferably 4 to 5.
  • an ethyleneoxyethylene group may be used.
  • the ratio of the above specific epoxy compound and N-substituted melamine is 1 equivalent of epoxy group
  • Such SJS ⁇ may be carried out without a solvent as in a casting material, or an appropriate organic solvent such as a coating varnish or a varnish for a laminated layer M may be used.
  • organic solvents such as methyl isobutyl ketone, ester solvents such as butyl acetate, ether solvents such as dioxane, alcohol solvents such as butanol, and cellosolves such as butyl sorb Solvents, carbitol solvents such as butyl carbitol, aromatic carbon solvents such as toluene and xylene, K-based solvents, amide solvents such as dimethylformamide and dimethylacetamide, and sulfoxides such as dimethylsulfoxide
  • the solvent include pyrrolidone solvents such as N-methylpyrrolidone and the like, and any organic solvent may be used as long as it does not significantly inhibit the hardness.
  • the reaction temperature Te 8 0-2 5 As the value, 80 to 250 ° is ⁇ , but 100 to 220 ° C is more preferable.
  • the reaction temperature Te 8 0-2 5 better good Or from 100 to 220.
  • the heating may be performed at a constant rate until the end of the curing reaction, but may be performed while changing the temperature from a low temperature to a high temperature at once, for example, 10 CTCX for 1 hour ⁇ 15 O 'C x 3 hours ⁇ 20 O' C 5 hours ⁇ ' ⁇ ', B-stage or oligomerization at relatively low temperature, then post-curing at high temperature, etc.
  • Curing may be carried out without a catalyst.
  • the reaction catalyst include tertiary amines such as N, N-dimethylpentylamine, quaternary ammonium such as tetraethylammonium bromide, and triphenylphosphine. 3rd class phosphine, Trifune Ordinary epoxy hard kSJ cores such as quaternary phosphonium such as rumonobendylphosphonium bromide, imidazole type such as 2-ethyl-4-methylimidazole, and Lewis acid type such as boron trifluoride-monoethylamine complex Any catalyst may be used as long as it is used, but a Lewis acid catalyst is particularly preferred.
  • the amount used is preferably 1 part by weight or less with respect to 100 parts by weight of the epoxy compound.
  • an arbitrary component can be further contained.
  • silicone oil-based, amide-based, ester-based antifoaming agents, hindered phenol-based, hindered amine-based, etc. By adding a small amount of various additives such as stabilizers, ⁇ stones such as stearic acid ⁇ , silicone resin-based and fluorine resin-based release agents according to the purpose, more preferable fi-epoxy resin M ⁇ can get.
  • Epoxy resin materials composed of an epoxy compound and N-substituted melamine have been conventionally known.However, a specific epoxy compound is used, and furthermore, excellent flHft properties can be obtained depending on the mixing ratio with the N-substituted melamine. Was found.
  • Examples of the trifunctional epoxy compound having a molecular structure in which the positions of the three epoxy groups are symmetrical include 1,3,5—tri (glycidyloxy) benzene, 1,3,5—trimesic acid used in the present invention.
  • the three epoxy groups are rotationally symmetrical with respect to the axis of the carbon-7j element bond of the central methine group, such as ether.Thick acid triglycidyl ester, trig Lysidyl isocyanurate and its alkyl group-substituted tris-((dimethyl) glycidyl isocyanurate, tris- (j3-methyl) glycidyl isocyanurate and the like triazin
  • Glycidyl isocyanurate and tris- (S-methyl) glycidyl isocyanurate are particularly preferred.
  • the reason why the heat resistance is higher than that of other polyfunctional epoxy compounds is not necessarily clear, but tris (hydroxyphenyl) methane triglycidyl.
  • the structure is very similar to that of the ether, and the phenol novolac polyglycidyl ether having a slightly larger number of epoxy groups is less likely to exhibit ff ⁇ property. It is easy to progress without stress defects, and it is easy to take a relatively regular and dense structure during curing.
  • the primary amino group and the Z or secondary amino group represented by the formula (I) have an active primary number of 3 to 5, and R 1 to R 6
  • the number of the alkyl group and the pendant oxyalkyl group is preferably from 1 to 18, and more preferably from 1 to 12.
  • the number of cycloalkyl groups is preferably from 4 to 8, more preferably from 5 to 6.
  • the number of substituents of the cycloalkylmethyl group or the methylcycloalkyl group is preferably from 5 to 9, and more preferably from 6 to 7.
  • R 5 and are together a connexion, - (CH 2) 4 - 7 -, or one CH 2 CH 2 one 0- CH 2 CH 2 may be one formed . More preferably, they are one (CH 2 ) 4 —pyrrolidino group and one (CH 2 ) 5 —piperidino group.
  • R 1 to R e are all hydrogen in the formula [I], namely, the melamine emissions themselves active fe element is six prone to curing failure due to poor compatibility. Conversely, even when the number of alkyl groups or hydroquinalkyl groups is 19 or more, the activity as a curing agent is poor, and there is a problem that poor curing is likely to occur.
  • the above-mentioned curing reaction between the symmetric epoxy compound and the N-substituted melamine is based on a mechanism in which a primary or secondary amino group of the N-substituted melamine is added to the epoxy group of the epoxy compound, and a catalyst of the N-substituted melamine.
  • 1 equivalent of the active 14 ⁇ element of the N-substituted melamine represented by the formula [I] is too large, and the active is cured at a ratio of 0.1 to 0.7 equivalent. It is preferable to cure at a ratio of 0.2 to 0.6 equivalent.
  • the activity and element content are less than 0.1, the curing speed becomes extremely slow.
  • the activity exceeds 0.7 equivalent, the unreacted ⁇ ⁇ ⁇ -substituted melamine, which is not incorporated into the polymer by chemical bonding, remains moist.
  • the resin produced has problems such as foaming at high temperatures and abnormal plasticization.
  • Such a catalyst may be a non-catalyst, but a catalyst such as a tertiary amine, a quaternary ammonium, or a Lewis acid may be used as the catalyst.
  • catalysts such as 4-monum and Lewis acid may become a source of chlorine and fluorine ions in the electronic materials field, and may be less than 1% by weight of the resin M ⁇ . It is preferred to use.
  • Solvents that can easily inhibit curing include bonbonic acid-based solvents, 1S3 ⁇ 4X is a secondary amine-based solvent, and a solvent having a phenol-tfoK acid group. It is preferable that the amount is 1 part by weight or less based on 100 parts by weight of the compound.
  • Epoxy compound (A1) to (A4), N-substituted melamines (B1) to (B6), and melamine (Ml ), Boron trifluoride monoethylamine (C1) was prepared.
  • Epoxy compound (A1) to (A4), N-substituted melamines (B1) to (B6), and melamine (Ml ), Boron trifluoride monoethylamine (C1) was prepared.
  • Tris (hydroxyphenyl) methane triglycidyl ether (Tactyx 742, trade name, manufactured by Dada Chemical Co., Ltd., epoxy content 6.3 equivalent k) was used as it was.
  • Triglycidyl isocyanurate (trade name: TEPIC-S, manufactured by Nissan Chemical Industries, Ltd., a high-quality product of triglycidyl isocyanurate, epoxy group content: 10.0 kg / kg) was used as it was.
  • 2,4-Bisamino-6-chloro-1,3,5-triazine was obtained in the same manner as in N-substituted melamine (B1).
  • B1 N-substituted melamine
  • 14.5 g (0.1 mol) of the obtained 2,4-bisamino-6-chloro-1,3,5-triazine was added.
  • 60 g of the mixture, 60 mL of 1,4-dioxane, and 26.9 g (0.1 mol) of n-stearylamine were added, and the mixture was allowed to reflux with stirring, followed by stirring at 3:00.
  • a silicone rubber spacer made by cutting two glass plates 14 mm in length, 240 mm in width and 240 mm in width x 3 mm in thickness with a mold release agent cut into a U-shape with a thickness of 1 mm and a width of 1 mm A fixation clip was used to secure a casting polymerization cell with an inner volume of 13 Ommx width 22 Ommx thickness lmm.
  • Table 1 shows the epoxy compounds (A1) to (A4), N-substituted melamines (B1) to (B7), melamine (Ml), and boron trifluoride / monoethylamine (C1).
  • Table 3 shows the results of the viscoelastic spectrum of the cured product, its tensile properties at high temperatures, and its elongation at high temperatures.
  • EZH shown in Table 1 represents an equivalent ratio of an epoxy group to an amino group activity of N-substituted melamine.
  • Example 4 100 e C 2hr 130 e Cx2hr 150 ° C x2hr 200 e C 4hr
  • Example 5 150 e Cx3hr 180 e Cx4hr one embodiment 6 150 e C 3 r 180 e Cx4 r - an embodiment 7 150 ° Cx3hr 180 e Cx4hr - one Comparative Example 1 150 ° Cx3hr 180 e C 4 r 200 e Cx3hr — Comparative Example 2 150 e Cx3hr 180 ° Cx4hr 200 e Cx3hr — Comparative Example 3 150 e Cx3hr 180 e Cx4hr 200 e C 3 r
  • the obtained cured epoxy resin material is cut into length 5 0111111> ⁇ width 5111111 and thickness 1111111 by a motorized diamond and power meter to obtain a viscoelastic spectrum! Did ⁇ . Similarly, it was cut to dimensions of 15 Omm long x 10 mm wide x 1 mm thick, and subjected to bending strength! ⁇ . Table 3 shows the test results. The method is shown below.
  • Peak S of an, 5 is, in .smallcircle when more than 22 O e C, when 1 80-21 9-hand ⁇ When the value is 1 179 or less, it is indicated by X.
  • Comparative Example 4 ⁇ ⁇ X Comparative Example 5 ⁇ ⁇ X
  • Table 3 show that the epoxy resin compositions of Comparative Examples 1 to 5 have sufficient performance among the viscoelastic spectrum of the cured product, high-temperature bow I, and high-temperature elongation.
  • the epoxy resin product of the example shows that the performance is excellent in all of these properties.
  • thermosetting epoxy product of the present invention can be diluted with an organic solvent according to the formula below to prepare a relatively low viscosity of 2 to 1000 cps. Also, without using a solvent, after mixing the evoxy compound and the N-substituted melamine, they are pre-heated to form a B-stage or oligomer and adjusted to a relatively low viscosity of 1000 to 1000 cps. It has the feature of being able to.
  • the storage stability after mixing is extremely high, at least 6 months at room temperature, and the blending stability with various liquid materials. In addition, the fiber before curing can be easily cured.
  • This curing is usually a gas furnace, a hot air furnace, an infrared ray Italy, microwave oven, can be cured in degrees about 1 0 0 ⁇ 2 0 0 e C in 1-5 hours using an induction heating furnace or the like.
  • the solvent can be volatilized and the above-mentioned step S can be performed.
  • it is possible to mix and trap inorganic fillers such as silica particles, alumina particles, and glass, and it has good ⁇ f properties with wood materials, materials, and various objects.
  • the thermosetting epoxy composition of the present invention is easy to handle.
  • the ii resin obtained by thermosetting the curable epoxy compound of the present invention has extremely high resistance and high chemical resistance. Therefore, ⁇ vehicles, ceramic paints ' ⁇ , concrete paints' glue, sealinks for construction / adhesion, paper and processing i ⁇ agents, glass cloth epoxy composites, carbon composites, boron fiber reinforced Composite materials, female transmutation, pharmaceuticals' binder for pesticides, plastic It is also useful for applications such as surface coating agents for coatings, glass breakage prevention coating agents, female-type maskin U, and resin sealants for electronic components.

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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)
  • Compositions Of Macromolecular Compounds (AREA)

Abstract

La présente invention concerne une composition époxy thermodurcissable comprenant un ou plusieurs composés époxy trifonctionnels dont la structure moléculaire est caractérisée par une disposition symétrique des groupes époxy, et une ou plusieurs mélamines substituées en N, correspondant à la formule générale (I), (où X est (a) et R1 à R6 sont, chacun de façon indépendante, H, C¿1?-C18 alkyle, C1-C18 hydroxyalkyle, C4-C8 cycloalkyle, C5-C9 cycloalkylméthyle ou C5-C9 méthylcycloalkyle, à condition que trois à cinq éléments de R?1 à R6¿ soient hydrogène, ou alternativement R5 et R6 puissent s'unir pour former -(CH¿2?)4-7- ou -CH2CH2-O-CH2-CH2-), caractérisé par le fait que le volume de l'atome d'hydrogène actif présent dans les groupes amino primaires et/ou secondaires de la mélamine substituée ou des mélamines substituées est compris entre 0,1 à 0,7 équivalent par équivalent du groupe époxy du ou des composés époxy trifonctionnels; et une composition réfractaire à base de résine époxy, obtenue par thermodurcissement de ladite composition époxy. Ladite composition époxy est facile à manipuler et présente une résistance à la chaleur et aux produits chimiques très élevée.
PCT/JP1996/000621 1995-03-14 1996-03-13 Composition refractaire a base de resine epoxy WO1996028490A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU49534/96A AU4953496A (en) 1995-03-14 1996-03-13 Heat-resistant epoxy resin composition

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JP7/54070 1995-03-14
JP5407095 1995-03-14

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Publication Number Publication Date
WO1996028490A1 true WO1996028490A1 (fr) 1996-09-19

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102008061137A1 (de) 2008-12-09 2010-06-10 Borealis Agrolinz Melamine Gmbh Neue Triazinpolymere, Verfahren zu deren Herstellung und deren Verwendung

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS61501154A (ja) * 1984-01-31 1986-06-12 ザ　ダウ　ケミカル　カンパニー エポキシ樹脂組成物およびそれからラミネ−トを製造する方法
JPS6270415A (ja) * 1985-07-31 1987-03-31 ザ　ダウ　ケミカル　カンパニ− エポキシ樹脂組成物
JPH02173747A (ja) * 1988-12-27 1990-07-05 Tamura Kaken Kk 感光性樹脂組成物
JPH0379621A (ja) * 1989-05-12 1991-04-04 Mitsubishi Electric Corp 積層板用樹脂組成物
JPH0657209A (ja) * 1992-08-07 1994-03-01 Mazda Motor Corp 塗料組成物

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS61501154A (ja) * 1984-01-31 1986-06-12 ザ　ダウ　ケミカル　カンパニー エポキシ樹脂組成物およびそれからラミネ−トを製造する方法
JPS6270415A (ja) * 1985-07-31 1987-03-31 ザ　ダウ　ケミカル　カンパニ− エポキシ樹脂組成物
JPH02173747A (ja) * 1988-12-27 1990-07-05 Tamura Kaken Kk 感光性樹脂組成物
JPH0379621A (ja) * 1989-05-12 1991-04-04 Mitsubishi Electric Corp 積層板用樹脂組成物
JPH0657209A (ja) * 1992-08-07 1994-03-01 Mazda Motor Corp 塗料組成物

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102008061137A1 (de) 2008-12-09 2010-06-10 Borealis Agrolinz Melamine Gmbh Neue Triazinpolymere, Verfahren zu deren Herstellung und deren Verwendung

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