TW411347B - The production process and the use of poly-phenyl compounds, epoxy resin compositions and cured products - Google Patents

Abstract

Resin compositions with low viscosity, low water absorption, high adhesion, excellent heat resistance, light weight and good mechanical properties are described, which are useful as antioxidants, insulation materials, composite resins, adhesives, paints, and various industrial intermediate. They can contain poly-phenyl compounds as shown in formula (1) and epoxy resins as seen in formula (3). In formula (1), X is O or S, Q is H or 1-5C alkyl, R is H, 1-10C alkyl, alkoxyl or halogens. i, j, k, y and n are integrals. In which i is 1-6, j is 1-3, k is 1-5, y is 1-2 and n is an average between 1 and 15. In formula (3), G is dehydrate glyceryl. R, Q, X, n, y, I, j, k are the same as in formula (1).

Description

Patent Application No. 87110Π3 Revised Chinese Manual (October 88) A7 B7

Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs. 5. Description of Inventions (1) In particular, in recent years, along with its development in the field of electrical and electronics, seek for a high purity, moisture resistance, tightness, In order to increase the filler's high viscosity and reduce the viscosity of the resin, the characteristics of the resin are further improved. In addition, for aerospace materials, recreation, sports equipment, etc., a material that is lightweight and excellent in mechanical properties is sought as a structural material. Regarding these requirements, many proposals have been made regarding epoxy resins and resin compositions containing them, but they are hardly sufficient. (Means for solving the problems) In order to solve the aforementioned problems, the present inventors made intensive research on polyvalent phenol compounds and epoxy resins obtained by etherifying them with glycidyl groups, and completed the present invention. That is, the present invention relates to: (1) a polyvalent phenolic compound represented by formula ⑴, (9H) y / V / " (R) i (wherein 'X represents an oxygen atom or a sulfur atom, and q is A hydrogen atom or a carbon number alkyl group 'R is a hydrogen atom, a carbon number hydrocarbon group, an alkoxy group, or a halogen atom, and i, j, k, and y are respectively i = 1 to 6, j = i to 3, and k = l. ~ 5, y = an integer of 1 to 2. The average of 11 people means an integer of 1 to 15). (2) The polyvalent phenolic compound according to the above-mentioned ⑴ represented by formula ⑵.

• OH -5-

This paper size is in accordance with Chinese National Standard (CNS) M specification (Z10x297). Printed by the Ministry of Economic Affairs, Bureau of Work and Consumers Co-operation, 4113-47 at ------- B7 V. Description of Invention (丄) '(Technical field to which the invention belongs) The present invention relates to an S # polyvalent phenol compound and an epoxy resin obtained by acidifying glycidyl of the polyvalent compound, which can be used as a resin for various plastics Sour vinegar 'PEEK, PP0, polylithic wind and other raw materials, raw materials for thermosetting resins (epoxy resin, cyano resin, acrylic resin, etc.), oxidation inhibitors, and high-reliability semiconductor packaging 、 Insulation materials for electronic parts and various composite materials including laminated board (printed circuit board) or CFRP (complete fiber shoot plastic), adhesives, coatings, molding materials, etc., various industrial intermediates β ( Conventional technology) Polyvalent phenol compounds can be widely used in thermoplastic plastic materials, thermosetting resin materials, insulating materials for electrical and electronic parts, structural materials, adhesives, coatings, and other constituents and oxidation inhibitors. (Problems to be Solved by the Invention) However, in recent years, in order to be used in various applications, the characteristics are also required to be diversified, and conventional cases of bisphenol A or bisphenol F, phenol novolac, or cresol novolac have also emerged. Many polyvalent phenolic compounds are synthesized. Especially in the field of electrical and electronic parts, we are looking for a kind of hardening resin composition with low viscosity, low moisture absorption, and south adhesion, and its hardened material. However, it is still difficult to say that the epoxy resin obtained by 'encapsulating the glycidyl group of the test compound' has excellent electrical characteristics, heat resistance, adhesion, and moisture resistance due to workability and its cured product ( It is widely used in the fields of electrical and electronic parts, structural materials, adhesives, coatings, etc. This paper has a moderate degree of paper; J1 standard, standard (CNS) Λ4 specification (210X29 secret) (谙 read the note on the back first)悫 Matters will be rewritten on this page} 10--5 Patent No. 87110173_Amendment of Chinese Manual (October 88) A7 B7 V. Description of Invention (7)

The policy of the Consumer Cooperatives of the Central Bureau of Standards of the Ministry of Economic Affairs is described below for the epoxy resin of the present invention. The epoxy resin of the present invention represented by the formula (3) can react the polyvalent phenolic compound of the present invention represented by the formula (1) with epoxy prime in the presence of a metal oxide. Specific examples of epoxiconyl propanes that can be used, such as epoxy gas propylene production ... m epoxy gas propylene, methyl methoxide, methyl-epichlorohydrin, etc., but should be Cheap epichlorohydrin that is easily available in the industry. This reaction can be performed according to a conventional method. For example, in a mixture of a compound of the formula (I) and a epoxinan propane, all or slowly adding a test metal hydroxide such as sodium hydroxide, hydroxide dehydration, etc., and at a time between 20 and 120. (: The reaction time is 2G hours. At this time, the metal hydroxide can be used in the aqueous solution. In this case, the metal hydroxide is continuously added, and the water is continuously discharged from the reaction system under dust reduction. And epoxy tooth propylene propanes' further separation, removal of water, the method of continuous return of epoxy nanox propanes to the reaction system.… In the above method, the use of epoxy propylene The equivalent of several bases of the compound of the formula ⑴ is generally 0.5 to 20 moles, more preferably the mole. The amount of metal hydroxide used is generally 0 relative to the hydroxyl i equivalent of the compound of the formula ⑴. .H.5 moles, preferably from 0 to 12 moles. In the above reaction, by adding dimethyl hydrazone, dimethyl sulfoxide, carbamoyl methylamine, 1,3-dimethyl-2 -Aprotic polar solvents such as imidazolinone can be used to obtain epoxy resins with low hydrolyzable concentration and suitable for use as packaging materials for electronic materials. The amount of aprotic polar solvents is equivalent to that of epoxy The weight of Nansu Binghu is generally 5 ~ 200% by weight. 'It is preferably 丨 〇 ~ 10.% by weight. -1 0- This paper size applies the Chinese National Standard (CMS) Α4 specification (210X297 public love) (Please read the precautions on the back before filling in this page) Order λ No. 87110Π3 Chinese specification amendment page (1 in 88 〇Month) A7 B7

Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs. 5. Description of Inventions (1) In particular, in recent years, along with its development in the field of electrical and electronics, seek for a high purity, moisture resistance, tightness, In order to increase the filler's high viscosity and reduce the viscosity of the resin, the characteristics of the resin are further improved. In addition, for aerospace materials, recreation, sports equipment, etc., a material that is lightweight and excellent in mechanical properties is sought as a structural material. Regarding these requirements, many proposals have been made regarding epoxy resins and resin compositions containing them, but they are hardly sufficient. (Means for solving the problems) In order to solve the aforementioned problems, the present inventors made intensive research on polyvalent phenol compounds and epoxy resins obtained by etherifying them with glycidyl groups, and completed the present invention. That is, the present invention relates to: (1) a polyvalent phenolic compound represented by formula ⑴, (9H) y / V / " (R) i (wherein 'X represents an oxygen atom or a sulfur atom, and q is A hydrogen atom or a carbon number alkyl group 'R is a hydrogen atom, a carbon number hydrocarbon group, an alkoxy group, or a halogen atom, and i, j, k, and y are respectively i = 1 to 6, j = i to 3, and k = l. ~ 5, y = an integer of 1 to 2. The average of 11 people means an integer of 1 to 15). (2) The polyvalent phenolic compound according to the above-mentioned ⑴ represented by formula ⑵.

• OH -5-

This paper size applies Chinese National Standard (CNS) M specification (Z10x297). 411347 A7 B7 V. Description of the invention ((where 'X, Q, R and j represent the same meaning as in the formula ⑴, and 1 ~ 4 (Integer). ⑶ The polyvalent phenolic compound described in the above ⑴ or ⑵, wherein X in the formula 为 is an oxygen atom. ⑷ The polyvalent phenolic compound of any of the above ⑴ to ⑶, where η is more than 10 The following: 1.5 (5) — a method of producing polyvalent phenols and a compound of the formula, characterized in that phenol is made

CNO is printed (Q) i by the standard department male laboratories in Co., Ltd. (In the formula, X, Q and j represent the compounds with the same meaning as those in formula ⑴ are condensed in the presence of a basic catalyst. (2) The production method described in the above (1), which is classified as · Dimethylbenzene brewing. 〇⑺The production method described in the above (6), wherein, (2) is 2,5, (2,2,2,2,2,2,2,2,4-tearyl) biphenyl. In the "Manufacturing Method", the facial catalyst is one or more selected from the group consisting of metal hydroxides, aging earth metal oxides, metal reduction compounds, and alkaline earth metal alkoxides. ⑼An epoxy resin , Which is represented by the formula ⑶ --1 ---.. I— —II I —----. -1 _ (Please read the notes on the back before filling in this page) (〇G) y

Q tR) i Η I -C- (Q) j (〇G) y \ dead a \ t ut

/ A -fl (Z) (R) k -6- This paper size is applicable to the national standard (CNS) A4 specification (210XM7 male t) 1 411347

V. Description of the invention (4) (where σ represents glycidyl, R, Q, X, 11 yah; j and k represent the same meaning as in formula ⑴) a ⑽ an epoxy resin, which is represented by formula ⑷ As shown.

(In the formula, G, R'Q, X, and j represent the same meaning as in formula (3), m is the average 値, which represents a real number from 0 to 20, and h is an integer from 1 to 4). ---.—.- IΙΦ! Ί Please read the note on the back ¾ and then write this page} The print by the Central Government Bureau of Zhenggong Consumers' Cooperatives (11) —A thermosetting resin combination The substance is a polyvalent phenolic compound as described in any one of the above-mentioned ⑴ to (3) and / or the epoxy resin described in the above ⑼ or ⑽. (Ii) A hardened material which is formed by hardening the thermosetting resin composition according to the above (11). (I) A semiconductor device 'uses the thermosetting resin composition described in the above (ii). 04) —A kind of thermoplastic plastic, which uses the polyvalent phenolic compound of any one of the above-mentioned ⑴ to ⑶ as a raw material. (Brief description of the drawing_single explanation) Fig. 1 shows a 1H-NMR spectrum of the polyvalent phenol compound (P1) of the present invention obtained in Example A1. Fig. 2 shows the iH-NMR spectrum of the polyvalent compound (P2) of the present invention obtained in Example 82.2. (Implementation form of the invention) The present invention is a multivalent amidine compound, which is a combination of amidines and the formula -7- This paper is used by the Chinese country ¥ ^^) A4 specifications ~ ————- _ Central Standard of the Ministry of Economic Affairs Bureau Male Workers 'Consumer Cooperatives Co., Ltd. Yinfan 411347 at' imum (5) — '' ———— It is obtained by polycondensation with the catalyst in the presence of a solvent as needed. Specific examples of the compound of formula ⑻ which can be used include furfural, 3-furfural, 3-methylfurfural '5-methylfurfural, 5-ethylfurfural, 2-thiophenol carboxylic aldehyde, and 3.thiophenol carboxylic aldehyde' 3-methyl-2-thiophenol carboxylic aldehyde and the like, χ in formula χ is preferably an oxygen atom. The compound of formula (I) is not limited to these, and it may be used alone or in combination of two or more. Examples of phenols include xylenol such as phenol, cresol, 2,6-xylenol, etc., and trimethyl glutamate, 2-second butyl-5 methyl group, etc. 2-third butyl_4_ methylphenol, alkenyl phenol 'octylphenol, phenylphenol, diphenylphenol' guaiacol, hydroquinone, resorcinol, catechol, naphthol, Dihydroxynaphthalene, methylnaphthol, allylphenol and the like are preferably 2,6-dimethylphenol or alkylphenol. Phenols are not limited to these, and two or more kinds may be used alone or in combination. The amount of phenols used is 1 mole compared to the compound of formula (1), which is generally mole, preferably from 8 to 10 moles. Examples of the solvent include, but are not limited to, methanol, ethanol, propanol, isopropanol, toluene, and xylene, and two or more kinds may be used alone or in combination. When using a solvent, the amount used is generally 5 to 500 parts by weight, and preferably 10 to 300 parts by weight relative to 100 parts by weight of phenols. The catalyst is preferably a basic compound. Even if the acidic catalyst can also be polymerized, it will also cause reactions between the compounds of formula ⑻, and many by-products. There are also methods of using organometallic compounds, but the cost is disadvantageous. Specific examples of the test catalyst that can be used include alkali metal hydroxides such as lithium argon oxide, sodium hydroxide, and hydroxide; alkaline earth metal hydroxides such as magnesium hydroxide and calcium hydroxide; and oxygen Sodium, Sodium Ethoxylate, Sodium Methoxylate, B (Please read the precautions on the back before filling this page)

411347 A7-Central Bureau of Standards, Bay Area! Printed by the Industrial Consumers' Cooperatives. 5. Description of the invention (6) ---- Metal-based oxides of milk-based, third-butoxy materials, alkaline earth metal alkoxides such as magnesium methoxylate, magnesium oxylate, etc. Etc., but it is not limited to this, it can be used alone or in combination. The amount of the catalyst used is more than 1 mole per mol, generally 0'005 ~ 2 · 0 mole, preferably 0.01 ~ 1.1 mole. . 2. The reaction is based on the compound represented by formula (a). (In the solvent, if necessary,%.) A catalyst is added to the tritium compound to heat the reaction. In addition, after heating the mixture of amidines and the catalyst (adding the catalyst as needed), the compound of formula ⑻ can also be slowly added. The reaction time is 5 to 100 hours. The reaction temperature is 50 to ΐ5 () χ :. After the reaction is completed, the reaction mixture is neutralized, and the unreacted raw materials and solvents are removed under excessive pressure or heat and pressure to obtain the polyvalent alcohol compound of the present invention. When the polyvalent brewing compound of the present invention thus obtained is a polymer compound containing a compound in which η exceeds 0 in Formula (I), ^ is preferably ^ or more and 忉 or less. The polyvalent amidine compound of the present invention represented by the formula (I) is obtained by purifying the compound of the formula (I) obtained by the aforementioned method. In the synthesis of formula-like compounds, it becomes a variety of raw materials. By using 2,6-dialkylphenol, 2,3,6-trialkylphenol, 2'5,6-tetraalkylphenol, etc. Specific phenols can also be 'synthesized selectively' using this compound as a raw material. If an epoxy resin or a cyano resin is synthesized, the reactivity will increase. When used as a hardener for the epoxy resin or cyanate resin described below, The reactivity is good, so the hardenability can be improved. The polyvalent phenolic compound of the present invention thus obtained can be used directly as a raw material for thermoplastics < or as a thermosetting resin composition as described later. Please m Reading item f Φ-The paper size of the booklet, Jia Pi (CNSU ^ iTTTox 297 ^ t 'Patent No. 87110173 _ Petition for Chinese Manual Amendment Page (October 88) A7 B7 V. Description of Invention (7)

The policy of the Consumer Cooperatives of the Central Bureau of Standards of the Ministry of Economic Affairs is described below for the epoxy resin of the present invention. The epoxy resin of the present invention represented by the formula (3) can react the polyvalent phenolic compound of the present invention represented by the formula (1) with epoxy prime in the presence of a metal oxide. Specific examples of epoxiconyl propanes that can be used, such as epoxy gas propylene production ... m epoxy gas propylene, methyl methoxide, methyl-epichlorohydrin, etc., but should be Cheap epichlorohydrin that is easily available in the industry. This reaction can be performed according to a conventional method. For example, in a mixture of a compound of the formula (I) and a epoxinan propane, all or slowly adding a test metal hydroxide such as sodium hydroxide, hydroxide dehydration, etc., and at a time between 20 and 120. (: The reaction time is 2G hours. At this time, the metal hydroxide can be used in the aqueous solution. In this case, the metal hydroxide is continuously added, and the water is continuously discharged from the reaction system under dust reduction. And epoxy tooth propylene propanes' further separation, removal of water, the method of continuous return of epoxy nanox propanes to the reaction system.… In the above method, the use of epoxy propylene The equivalent of several bases of the compound of the formula ⑴ is generally 0.5 to 20 moles, more preferably the mole. The amount of metal hydroxide used is generally 0 relative to the hydroxyl i equivalent of the compound of the formula ⑴. .H.5 moles, preferably from 0 to 12 moles. In the above reaction, by adding dimethyl hydrazone, dimethyl sulfoxide, carbamoyl methylamine, 1,3-dimethyl-2 -Aprotic polar solvents such as imidazolinone can be used to obtain epoxy resins with low hydrolyzable concentration and suitable for use as packaging materials for electronic materials. The amount of aprotic polar solvents is equivalent to that of epoxy The weight of Nansu Binghu is generally 5 ~ 200% by weight. 'It is preferably 丨 〇 ~ 10.% by weight. -1 0- This paper size applies Chinese National Standard (CMS) A4 specification (210X297 public love) (Please read the notes on the back before filling in this page) Order λ 411347 A7 B7 V. Description of the invention (8) One other than the aforementioned solvents 'With the addition of alcohols such as methanol, ethanol, etc., the reaction is easy to proceed. Also,' toluene, methane, etc. can be used as solvents. ^ ---- ^! (谙 Please read the precautions on the back before filling in this page ) In addition, in the mixture of the compound of the formula VII and the excess epoxinan propanes, a fourth-order ammonium such as tetramethylammonium chloride, tetramethylammonium bromide, vaporized fluorenylbenzyl ammonium, and the like can be used. A salt is used as a catalyst, and a solid or aqueous solution of an alkali metal hydroxide such as sodium hydroxide or potassium hydroxide is added to a haloether of a compound of the formula (I) obtained by reacting at 50 ec to 150 ° for one hour. The reaction is performed at 20 to 12.0 for 1 to 20 hours to make ring opening from the alcohol ether, and the epoxy resin of the present invention can also be obtained. The amount of the fourth-stage recorded salt at this time is relative to the compound of formula ⑴ The hydroxyl group is generally 0.001 to 0.2, and it is preferably mol. After these reactants are washed with water or under water and reduced pressure, excess epoxy compounds are removed, and then dissolved in solvents such as toluene, xylene, methyl isobutyl ketone, etc., and steel hydroxide and hydroxide are added. Wait for the test of the aqueous solution of the metal oxychloride, and then carry out the reaction. At this time, the amount of the test metal oxynitride is relative to the hydroxyl group of the compound of formula 当! The reaction temperature is generally 50 ~ 120 ° C, and the reaction time is generally 0.5 ~ 2 hours. After the printing reaction of the Mogong Cooperative Cooperative of the Central Procurement Bureau of the Ministry of Ports of Hong Kong is finished, it is washed by filtration. After removing the by-product salts, the solvent such as toluene, xylene, methyl isobutyl ketone and the like is distilled off under heating and reduced pressure to obtain an epoxy resin with few hydrolysates. In addition, the step of synthesizing the compound of the formula (I) and the step of epoxidation may be performed continuously. For example, after reacting the compound of formula ⑻ with the test method by the aforementioned method, 'by neutralizing or filtering, distillation under heating and reduced pressure, etc., without removing unreacted raw materials and solvents,' the epoxy compound is directly added to In the Department, the former -11- Pu Zhilong seniority applies the Chinese storehouse standard (CNS) Λ4 specification (210X 297 mm) Qingmanbuzhongzhong # 半 局 贞 工 消 贽 Cooperation private seal " 411347 Αν _____ _ B7_ — V. Description of the invention (9) ~ The method described above is carried out for epoxidation. In the final solvent distillation stage, unreacted epoxides can be distilled off together with the solvent. Also, the epoxy resin of the present invention represented by the formula (I) can be obtained by epoxy-oxidizing the compound represented by the formula (I) in the same manner as described above.値 Very large compounds. Hereinafter, the thermosetting resin composition of the present invention will be described. Β The polyvalent compound of the present invention is used as a curing agent for epoxy resins and / or cyanate resins. In this case, the polyvalent phenol of the present invention can be used. Compounds are used alone or in combination with other hardeners. When used in combination, the proportion of the polyvalent phenol compound of the present invention in the total hardener is preferably 10% by weight or more, and more preferably 20% by weight or more. Specific examples of other hardeners that can be used in combination with the various resins of the present invention include ammonia-based compounds, acid anhydride-based compounds, amido-based compounds, and phenol-based compounds. Specific examples of other hardeners that can be used are: diaminodiphenylmethane, dihexyltriamine, triethylenetriamine, diaminodiphenylphosphonium, isophora diamine, dicyano Polyamine resin synthesized by diamidine, linoleic acid dimers and ethylenediamine, g too acidic acid, 1,2,4- trimellitic acid, pyromellitic acid, maleic acid liver, tetrahydrog Too-acid fiber, methyltetrahydrogenate, nadic anhydride, hexahydrophthalic anhydride, methylhexahydrophthalic anhydride, bisphenols, phenols Alkyl-substituted phenol, dihydroxybenzene, dibasic test, etc.) and various polycondensates, polymers of phenols and various diene compounds, polycondensates of g # and aromatic dimethylol groups Phenols and their denaturants, imidazole, BF3-amine complexes, guanidine derivatives, etc. Specific examples of the epoxy resin that can be used in the thermosetting resin composition of the present invention are mainly the epoxy resin of the present invention, and the other epoxy resins are -12- This paper size applies to Chinese national standards ( CNS) A4 specification (2 〖〇χ 297 公 瀣） ----- H-l · --In-* n------ τ I-* Please read the precautions on the back first " (Fill in this page) Printed by the Central Standards Bureau of the Ministry of Economic Affairs, M Industrial and Consumer Cooperatives, 411347 A7-________ B7 V. Description of the invention (1〇) Niu Huan and other types of tests, the enemy ' Examination, monophenylbenzene, dihydroxy hydrazone, etc.) polycondensates with various aldehydes, phenols, polymers of various olefin compounds, polycondensates of phenols and aromatic dimethylol, bisphenols Glycidyl ether epoxy resin, alicyclic epoxy resin, glycidyl amine epoxy epoxy resin 3 glycidyl vinegar epoxy resin, etc. The epoxy resin used may be known, and is not limited to these. These can be used alone or in combination of two or more. When the epoxy resin of the present invention is used as the epoxy resin in the thermosetting resin composition of the present invention, the epoxy resin of the present invention can be used alone or in combination with other epoxy resins described above. When other epoxy resins are used in combination, the proportion of the epoxy resin of the present invention in the total epoxy resin is preferably 20% by weight, and more preferably 30% by weight or more. &Amp; The thermosetting resin composition of the present invention When an epoxy resin is contained, it may also be used as an epoxy resin hardening accelerator, if necessary. Examples of the hardening accelerator include: imidazole compounds such as 2-methylimidazole and 2-ethylimidazole, boron difluoride complexes such as phosphorus compounds such as triphenylphosphonium, trioctyllin, etc. The amount of the compound used is relative to epoxy The resin is 100 parts by weight and is 0.001 to 15 parts by weight, and preferably 0 to 1 to 10 parts by weight. Specific examples of the cyanate resin that can be used in the thermosetting resin composition of the present invention include: dicyanooxybenzene, tricyanooxybenzene, dicyanohydrin, dicyanobiphenyl, 2 , 2, _bis (4-cyanooxyphenyl) propane, bis (4-cyanooxyphenyl) methane, bis (3,5-dimethyl-4-cyanooxyphenyl) methane, 2,2_-bis (3,5-diamidino_4_cyanooxyphenyl) propane, 2,2, _bis (4_cyanooxybenzyl) ethyl-13- paper & _Cause (CNS) Α4 Specification (21〇 × 297 公 楚) ---------^ --------, Order "(Please read the precautions on the back before filling in this book Page) 'Economy Central #Bi Bureau employees allow the cooperative to print on 411347 Α7 Β7 V. Description of the invention (η) Appearance, 2,2'-bis (4-cyanooxyphenyl) hexafluoropropane, bis (4- Cyanooxyphenyl) pyrene, bis (4-aminooxyphenyl) sulfide bond, self-intentioned sulfanilic acid, and the hydroxyl group of fen / dicyclopentane dicondensate condensate is converted into cyanooxy, but not It is limited to these. When the thermosetting resin composition of the present invention contains a cyanate resin, it is necessary to triquantize the cyanooxy group to form a sym-triazine, if necessary. The ring may also contain catalysts such as zinc naphthenate, cobalt naphthenate, copper naphthenate, lead naphthenate, zinc octoate, tin octoate, lead acetamidate, dibutyltin maleate, and the like. The media is 1,000 parts by weight with respect to the total weight of the thermosetting resin composition, generally 0.0001 to 0.10 parts by weight, and preferably 0 00015 to 0 0015 parts by weight. In order to make the thermosetting resin composition of the present invention The hardened material is hardened, and it is difficult to give flame resistance. It is only necessary to use the glycidyl ether of tetrabromobisphenol A or β / bromofluorenol novolac epoxy resin together. The hardened material usually contains 10 to 40 weight. % 'Is preferably 12 to 35% by weight, and more preferably 15 to 27% by weight of bromine, as long as the above-mentioned epoxy resin is blended. The thermosetting resin composition of the present invention may contain the aforementioned epoxy resin and cyanic acid The ester resin may be used alone or in combination. In the thermosetting resin composition of the present invention, the amount of the hardener used is generally from 0 to 15 equivalents relative to 1 equivalent of the epoxy resin, and preferably 0.6M 2 equivalents. Relative to 1 equivalent of cyanate resin, generally 0 ~ 15 equivalents, preferably 0 2 In the thermosetting resin composition of the present invention, known additives need to be adjusted. Specific examples of the additives that can be used include, for example, polybutadiene and its denaturants, and denatured copolymers of propionitrile. , Polyphenylene ether, polystyrene, polyethylene, polyimide, fluororesin, maleimide-based compounds-14- This paper is suitable for the standard / ί] National Park Material Transfer (CNS) A4 Specification (2 丨0 彳 297 公 楚) ^ 1 »»---·-I II ΐ---: I— I -I-I-. -I ^ —-. (Please read the notes on the back before filling out this page ) 411347 A7 -________ B7 V. Description of the Invention (12) — Silicone gel, silicone oil, and silicon oxide, aluminum oxide, calcium carbonate, quartz powder, aluminum powder, graphite, talc, clay 'iron oxide' oxidation Inorganic fillers such as titanium, aluminum nitride, asbestos, mica, glass powder, glass fibers, glass nonwovens, or carbon fibers, surface treatment agents for fillers such as silane coupling agents, release agents, carbon black, phthalocyanine Coloring agents such as blue, phthalocyanine green, etc. The thermosetting resin composition of the present invention can be uniformly prepared in a predetermined ratio. Mixing the components described above is obtained. The mixture can be heated and melted at a temperature 20 to 1 OCTC higher than the softening point of each component as required. Further, each component of the thermosetting resin composition may be uniformly dispersed or dissolved in a solvent or the like, and may be mixed. The solvent is not particularly limited, but specific examples that can be used include toluene, xylene, methyl ethyl ketone, methyl isobutyl ketone, dioxane, methyl cellosolve, and dimethylmethaneamine. These solvents are used in an amount of 100 parts by weight with respect to the resin, generally 5 to 300 parts by weight, and preferably 10 to 15 parts by weight. The Ministry of Economy-Ministry of Standards and Industry Bureau of Pakung Consumers 'Cooperative Co., Ltd. printed 5' The thermosetting resin composition of the present invention is suitable for use in a low-dielectric laminate. When used as a laminated board, in order to require flame resistance, the hardened material generally contains 10 to 40% by weight, preferably 12 to 35% by weight, and more preferably 15 to 27% by weight bromine. A halogenated epoxy resin or Compounds containing halogens in their molecules act as hardeners. Such a laminated board is prepared by, for example, dissolving the thermosetting resin composition of the present invention in a solvent to form a varnish, and impregnating the varnish with cellophane, non-woven fabric, synthetic fibers, paper, etc. The substrate is heated and dried to remove the solvent. To make a prepreg. Secondly, a predetermined number of the prepregs are stacked to form a laminated body, where copper foils are laminated on one or both sides of the laminated body, and the composition of the present invention is hardened by heating and pressing. At this time, the solvent is -15- The standard of this paper is applicable to China National Standard (CNS) A4 specification (2 10 × 297 mm) 411347 at _____B7 V. Description of the invention (13) For example, toluene, xylene, propane, Methyl ethyl ether, methyl isobutyl hydrazone, dimethyl methylamine, etc. These solvents are generally used in the mixture of the composition of the present invention and the solvent in an amount of 10 to 70% by weight, preferably 15 to 65% by weight. When the invented polyvalent phenolic compound is used as a thermoplastic plastic raw material, the same well-known method as the conventional phenolic compound can be adopted. (Examples) Hereinafter, the present invention will be described more specifically with reference to examples. The present invention is not limited to these embodiments. In the examples, the epoxy group equivalent 'penetration point', hydrolyzable chlorine concentration, melting dryness, and melting point were measured under the following conditions. In the following, parts mean parts by weight. ① Epoxy group equivalent Measured in accordance with JIS K-723 6. ② Softening point Measured in accordance with JIS K-7234. ③ Hydrolysable chlorine concentration Add the IN KOH ethanol solution to the dioxane solution of the sample, reflux for 30 minutes, and measure the amount of free gas by the silver nitrate titration method, and divide by the weight of the sample, 値. Printed by the Central Standards Bureau of the Ministry of Economic Affairs, Consumers ’Cooperatives ----------- ^ w .------ ^, order; (Please read the notes on the back before filling out this page) ④ Melt dryness measuring machine with cone plate method at a melting viscosity of 150 ° C: ICI ifj temperature dryness meter (manufactured by SEARCH EQUIPMENT (LONDON) LTD.) ° cone Number: 3 (measurement range: 0 ~ 20 poise) Sample volume: 0.15 soil 0.01 g -16- This paper size is applicable to China National Standard (CNS) A4C grid (210X 297 mm) A7 B7 411347 V. Description of the invention (14) ⑤ The melting point is measured by DSC method, and the temperature rise rate is 10 ° C / min. Example A1 In a flask equipped with a stirrer, a reflux cooling tube, and a stirring device, 244 parts of 2,6-dimethylbenzene, 122 parts of methanol are fed, After stirring and dissolving 7 parts of sodium hydroxide, and heating to a reflux state, 96 parts of furfural was dropped over 2 hours. Then, after reacting at reflux temperature for 15 hours, it was neutralized with 140 parts of a 20% sodium dihydrogen phosphate aqueous solution, and 500 parts of water was added. Then, the precipitated crystals were recovered by filtration, washed with a solution of methanol: water = 1: 1, and then dried with a reduced-pressure dryer. As a result, the following formula (5) is obtained. Please read the note on the back * first.

-Ordered. Printed by the Ministry of Economic Affairs, Central Standard Bureau, Ministry of Work, and Cooperation. Printed 304 parts of the polyvalent phenol compound (Pl) of the present invention as shown. Melting point: i47 ° C. iH-NMR spectrum (CDC13 '3 00 MHz): Figure 1. Example A2 A flask equipped with a stirrer, a reflux cooling tube, and a stirring device was fed with 328 parts of 2-third butyl-5-methylphenol, 328 parts of methanol, and 4 parts of sodium hydroxide. After stirring and dissolving, After heating to a reflux state, 96 parts of bran was dripped over 2 hours. Then, at the reflux temperature, 4 parts of sodium hydroxide were added every 2 hours while reacting, for a total of 36 parts. After dripping furfural, the reaction should be completed. After 35 hours, 240 parts of methanol, 240 parts of water, and 200 parts of 3 5% hydrochloric acid aqueous solution were added. Then, the precipitated crystals were recovered by filtration, and washed with a solution of methanol: water = 2: 1. It was further washed with methanol and dried in a reduced-pressure dryer. As a result, it was obtained that the Chinese National Standards (CNS) A4 standard (210X 297 mm) was applied at the paper scale. 411347 A7 _ · B7 V. Description of the invention (15) The following formula:

332 parts of β-melting point of the present invention overcharged face compound (! * 2): 236.2371. iH-NMR spectrum (CDC13, 300 MHz): Figure 2. Example A3 In a flask equipped with a stirrer, a reflux cooling tube, and a stirring device, 113 parts of phenol and 28 parts of methanol and 12 parts of sodium hydroxide were charged. After stirring, dissolving, and heating to form a reflux state, the bran was dropped in 2 hours. 29 servings. Then, after reacting at reflux temperature (90 to 100 ° C) for 20 hours, 30 parts of a 35% aqueous solution of hydrochloric acid was neutralized, and 5 parts of an 80% aqueous solution of hydrazine was added. Then, methyl isobutyl hydrazone 1 was added, and after washing with water, the unreacted, methyl isobutyl ketone was removed under heating and reduced pressure, and the following formula (7) was obtained.

Η m The Ministry of Economic Affairs has awarded it-Bureau®! : Industrial Cooperative Press ^ (Please read the notes on the back before filling this page) [wherein, n = 3.1 (average 値)] 332 copies of the multivalent age compound (P3) of the present invention. The softening point of the obtained polyvalent phenolic compound was 92 ° C, and the melt viscosity was 5.1P. Example A4 In Example A1, except for changing 244 parts of 2,6-dimethylphenol to 2,5-di-18- This paper size is applicable to China National Standard (CNS) Λ4 specification (2! 0X297 mm ) 411347 A7 Β7 16 V. Description of the invention (Except for 244 parts of methylbenzene, the rest is subjected to the same operation, and the following formula is obtained:

301 parts of the polyvalent phenolic compound (P4) of the present invention are shown. The melting point of the obtained polyvalent phenolic compound was 192 ° C. Example A5 In Example A1, except that 244 parts of 2,6-dimethylphenol was changed to 272 parts of 2,3,6-trimethyl, and sodium hydroxide was changed to 5 parts of lithium hydroxide. Perform the same operation and get the following formula: ί-!---~ ——- (Please read the precautions on the back first and then complete this page)

298 parts of the polyvalent phenolic compound of the present invention (1 > 5) shown by the Indian Institute of Standards and Technology ’s Ordnance Industry Cooperative Co., Ltd. India Bi. The melting point of the obtained polyvalent phenolic compound was 176 ° C. Example A6 In Example A1, the same operation was performed except that sodium hydroxide was changed to 5 parts of lithium hydroxide, furfural was changed to 112 parts of 2-thiophenol carboxyaldehyde, and the reaction time was changed to hours.述 式 ⑽ Η

19- The paper size is in accordance with China Financial Standard Complete (CNS) M specifications (Bie Magic 97 41134 ^ a7 B7 '----- V. 307 copies of the compound of the present invention (P6) shown in the description of the invention (17) The melting point of the obtained polyvalent compounds is 167Ό. Example A7 ίί! (Jingxian first read the precautions on the back and then fill in this page} In Example A6, 'Except the 2,6- -methyl Benzene brewing was changed from 244 parts to 2,5 to 244 parts of dimethylphenol, and the reaction time was changed to other than 30 hours. The same operation was performed, and the following formula was obtained:

284 parts of the polyvalent phenol compound (P7) of the present invention are shown. The melting point of the obtained polyvalent compounds was 216 ° C. Example A8 The same operation was performed in Example A6, except that 244 parts of 2,6-dimethylphenol was changed to 272 parts of 2,3,6-trimethylphenol and the reaction time was changed to 60 hours. Can be obtained by the following formula:

^ Printed by Hong Kong ’s Ministry of Central Standards · Printed by the Bureau of Work and Industry Cooperative Cooperatives The present invention shows 284 parts of polyvalent phenolic compounds (P8) and the melting point of the obtained polyvalent phenolic compounds is 163 ° C. Example A9 ~ Al 1 epoxy resin was prepared in the amount shown in Table 1 with ortho-a have one epoxy resin [-20] The size of this paper is applicable to Chinese National Standard (CNS) Λ4 specification (2Ι ×× 297 mm). Ministry of Work, Central Bureau of Standards and Labor, Cooperatives, Cooperatives, Innu 411347 at _____B7 V. Description of the invention (18) The system of chemical medicine (stock), EOCN-1020, epoxy equivalent 198 "£ (1 softening point 65. 〇) (E1 ) 100 parts with the polyvalent phenol compound (ρι) ~ (ρ3) of the present invention, 1 part of the hardening accelerator (di Feng · jiphos), kneaded by a biaxial roller, pulverized and bonded, and then I75 C, A resin molded body can be obtained by using a Trausfei * molding machine under the condition of ISO seconds, and cured at 180 C for 8 hours to obtain a cured product of the present invention. The characteristics of the obtained cured product are measured under the following conditions. The results are shown in the table ^ Medium. • Glass transition temperature (TMA): tm-7000 temperature rise rate 2 ° C / min ° manufactured by Hori Kogyo Co., Ltd. • Water absorption rate: disk-shaped test piece with a boiling diameter of 5 cm x thickness of 4 min in 100 C water Weight increase rate after 24 hours (%) • Peel strength of copper foil: According to the method described in JiS C-64S1 (peel strength) Implementation. • Izod impact test: implemented according to Jis K77H). Table] 1 Example A9 A10 All Hardener P1 P2 P3 Hardening dose (parts) 134 169 133 Glass transition temperature (° c) 132 130 149 Water absorption (%) ) 1.02 0.99 1.13 Peel strength of copper foil (kg / cm) 2.5 2.6 2.5 Izod (kg / mm2) 21 23 17 Example B1 is compared with 161 parts of the polyvalent phenolic compound (P1) obtained in Example A1. 500 parts of epoxy gas propane (ECH, the same below) was fed into the reaction vessel, and diya-21- This paper size is in accordance with the Chinese National Standard (CNS) Λ4 specification (21〇χ297297) ----- Φ-- ---- rlr ·: (Please read the precautions of Back® first, and then fill in this page) 411347 A7 B7 V. Send out the instructions (19) 100 parts of ketone (DMS0 :, the same below), heat and stir After dissolution, while maintaining the temperature at 45 ° C, the reaction system was maintained at 45 Torr, and 100 parts of a 40% by weight aqueous sodium hydroxide solution was continuously dropped over 4 hours. At this time, the azeotropically distilled ECH and The water is cooled, and after liquid separation, only the reverse layer, ECH, is returned to the reaction system, and the reaction is performed on one side. Hydrogen and oxygen After the dropping of the sodium aqueous solution was completed, the reaction was performed at 45 ° C for 3 hours, and further reacted at 70 ° C for 30 minutes. After that, the water was repeatedly washed to remove the by-produced salt and difluorenylphosphine, and the excess was distilled off from the oil layer under heating and reduced pressure For epoxy propane, 500 parts of methyl isobutyl ketone was added to the residue and dissolved. With this fluorenyl isobutyl ketone solution, the solution was heated to 70 ° C, and 4 parts of 30% sodium hydroxide aqueous solution was added. After reacting for 1 hour, the reaction solution was repeatedly washed with water until the washing solution became neutral. Then, methyl isobutyl ketone was distilled off from the oil layer under heating and reduced pressure to obtain formula (13)

CHb τ (13) ----------------- ?! '「(Please read the notes on the back before filling this page) Central Bureau of Standards, Ministry of Economic Affairs, MT; [Wherein G represents a glycidyl group. In addition, hunger is 0.03 (average 値)] 210 parts of the epoxy resin (El) of the present invention. The epoxy equivalent of the epoxy resin (E1) is 222 g. / eq, softening point is 4yC, melt viscosity is 0.4 poise, and hydrolyzable chlorine concentration is 370 ppm. Example B 2 In Example B1, except that 161 parts of polyvalent phenolic compound (P1) was changed to Example Except for 203 parts of polyvalent phenolic compound (P2) obtained in A2, 650 parts in ECH and 120 parts in DMSO, the rest was performed in the same manner as in Example B. -22- Mystery & 'Manufacturing t. (CNS) μ specifications (plus heart 7 cm) A7 B7

Printed by the Central Department of the Ministry of Standards and Excise Department, Beigong Xiaoxian Cooperative ¾ 411347 V. Description of the invention (20) As a result, the formula (14) 〇CH2ijWCH, 0 C (CH3) 3 oh (HjC} jC-

(14) [In the formula, G represents a glycidyl group. m = 0.04 (average 値)] 245 parts of the present epoxy resin (E2). The epoxy resin (E2) has an equivalent weight of 270 g / eq, a softening point of 68 ° C, a volume capacity of 0.4 poise, and a hydrolyzable chlorine concentration of 36 ppm. Example B3 In Example B1, except that 161 parts of the polyvalent phenolic compound (Pl) was changed to 133 parts of the polyvalent phenolic compound (P3) obtained in Example A3, ECH was changed to 400 parts, and DMS0 was changed to 100 Other operations were performed in the same manner as in Example B1. As a result, the formula (15) is obtained

-H (is) [wherein G represents a glycidyl group, and n = 4.9 (average 値)] 170 parts of the present epoxy resin (E3). Epoxy resin (E3) has an epoxy equivalent of 225 g / eq, a softening point of 65 ° C, a melting dryness of 3.6 poise, and a hydrolyzable gas concentration of 410 ppm. Example B4 In a flask equipped with a stirrer, a reflux cooling tube, and a stirring device, 56 parts of phenol, 28 parts of methanol, and 2 parts of sodium hydroxide were fed. After stirring and dissolving, they were heated. Bi (CNS) Λ4 size (210X 297 mm) (Please read the precautions on the back to complete this page)

I Printed by the Ministry of Standards and Labor Administration of the People ’s Republic of China Standards Bureau 411347 A7 __________ B7 V. Description of the invention (21) Reflowed, and 29 parts of bran were dropped in 2 hours. Then, after reacting at a reflux temperature (80 to 90 ° C) for 20 hours, 25 parts of epichlorohydrin was added, and 12 parts of flake-shaped sodium hydroxide were continuously added at 70 ° C for 1 hour. After the addition of sodium hydroxide was completed, the reaction was carried out at 70 ° C for 1 hour. Subsequently, after washing with water repeatedly to remove by-produced salts and methanol, excess epichlorohydrin was distilled off from the oil layer under heating and reduced pressure, and 300 parts of fluorenyl isobutyl ketone was added to the residue to decompose. This methyl isobutyl ketone solution was heated to 70 ° T, and 4 parts of 30% by weight aqueous sodium hydroxide solution was added and reacted for 1 hour, and then the reaction solution was repeatedly washed with water until the washing solution became neutral. Then, methyl isobutyl ketone 'was distilled off from the oil layer under heating and reduced pressure to obtain 4) 70 parts of the epoxy resin of the present invention represented by the aforementioned formula (4) [n in formula (n = 4.9 (average)) ]. The epoxy equivalent (E4) has an epoxy equivalent of 24 g / eq and a 66 ° C melting point and a dry weight of 2.3 poise. The hydrolyzable chlorine concentration is 780 j > pm. Example B 5 The same operation as in Example B1 was performed in Example B1 except that 161 parts of the polyvalent phenol compound (P1) was changed to 161 parts of the polyvalent phenol compound (p4) obtained in Example A4. . As a result, the following formula can be obtained:

[Wherein G represents a glycidyl group. ) ^ = 0.08 (average 値)] 221 parts of the epoxy resin (E5) of the present invention shown. Epoxy equivalent of epoxy resin (E5) is 2j2 g / eq, softening point is 66 ° C, melting particle size is 0,5 poise, plus -24- This paper size applies to China National Standard (CNS) A4 specifications (2! 〇χ29? Mm) ---------- ♦ II (谙 Please read the notes on the back first # -Fill this page)

, tT A7 Printed by the Ministry of Standards and Quarantine Bureau of the Ministry of Liability and Labor Cooperatives 411347 ----------__ B7 V. Description of the invention (22) The concentration of water-decomposable chlorine is 380 ppm. Example B6 In Example B1, the same operation as in Example B1 was performed except that 161 parts of the polyvalent phenolic compound (ρι) was changed to 175 parts of the polyphenolic compound (p5) obtained in Example A5. . As a result, the following formula can be obtained:

[Wherein G represents a glycidyl group, m = 〇03 (average 値)] 219 parts of the present epoxy resin (£ 6) represented by. The epoxy group equivalent (E6) had an epoxy group equivalent of 238 g / eq and a pour point of 68. (:, Melt viscosity is 1.0 poise, hydrolyzable gas concentration is 370 ppm. Example B7 In Example B1, 161 parts of the polyvalent phenolic compound (P1) was changed to the polyvalent value obtained in Example A6. Except for 169 parts of phenolic compound (p6), the same operation as in Example B1 was carried out. As a result, Formula 以 was obtained.

[Wherein G is a glycidyl group, m = 0.04 (average 値)] 216 parts of the present epoxy resin (E7). Epoxy equivalent of epoxy resin (E7) is 233 g / eq 'softening point is 50 ° C, melting particle size is 0.4 poise' hydrolyzability. Chlorine concentration is' 400 ppm ° -25- This paper size applies to China Garden Home Standard (_CNS) Μ Specifications (210X 297mm) '(Please read the note on the back first' Implementation I fill out this page)

411347

A7 V. Description of the invention (23) Example B8 In Example B1, except that 161 parts of the polyvalent phenolic compound (Pl) was changed to 69 parts of the polyvalent phenolic compound (p7) obtained in Example A7, the rest The same operation as in Example B1 was performed. As a result, the following formula can be obtained:

〇CH2 ^ HCHj〇 CHa 〇H

.0G ⑽ [wherein G represents a glycidyl group, m = 〇07 (average 値)] 214 parts of the present epoxy resin (E8). Epoxy resin (E8) has an epoxy group equivalent of 239 g / eq, a softening point of 71 ° C, a melt viscosity of 0.6 poise, and a hydrolyzable gas concentration of 390 ppm. Example B9 The same operation as in Example B1 was performed in Example B1, except that 161 parts of the polyvalent phenol compound (ρm) was changed to 183 parts of the polyvalent phenol compound (p8) obtained in Example A8. As a result, you can get the formula ⑽ -------- ^ — 0 clothing! (Please read the notes on the back # -fill this page first)

ch3 oh 1

(20) Printed by Wu Gong Consumer Cooperative of the Ministry of Economic Affairs [In the formula, 'G represents glycidyl group, m = 0 04 (average 214)] The present epoxy resin is 9) 214 copies. The epoxy resin (E9) had an epoxy content of 248 g / eq and a softening point of 74. (: Melting viscosity is 410 ppm with decomposable lice concentration by adding I. Examples B10 to 18 The epoxy resins (E1) to (E9) obtained in Examples m to B9, compared to Guang-26- this paper The standard is applicable to the Chinese National Standard (CNS) A4 specification (210X297 mm) 411347 A7 B7 V. Description of the invention (24) 1 equivalent of oxygen resin, formulated with a hardener (phenol and phenol while the resin (made by Benhua Pharmaceutical Co., Ltd., PN- 80, 150 ° C melt viscosity 1.5 poise, softening point 86 ° C, hydroxyl equivalent 106 g / eq) 1 hydroxyl equivalent, and further 1 epoxy resin to mix 1 part hardening accelerator (triphenyl phosphorus), transfer The molded resin molded body was hardened at 160 ° C for 2 hours, and further hardened at 180 ° C for 8 hours. The physical property measurement results of the hardened products thus obtained are shown in Tables 2 and 3. Method to measure physical properties. • Water absorption: same as that of Examples A9 to Al 1. • Copper foil peel strength: 180 ° Peel test measurement temperature: 30 ° C Tensile speed: 200 mm / min Copper foil:铉 〆-Kobu Co., Ltd. JTC foil 70 • Izod impact test: same as the implementation Example A9-A11 is carried out; then determined. M- ·--. _ I---I (锜 Please read the note on the back before you fill in * | this page) Printed by the Shell Standard Consumer Cooperative of the Central Bureau of Standardization of the Ministry of Economic Affairs ¾ Table 2 Example B10 B11 B12 B13 B14 Epoxy resin E1 E2 E3 E4 E5 Water absorption (%) 1.2 1.1 1.3 1.2 1.2 Copper foil peel strength (kg / cm) 2.8 2.6 2.4 2.5 2.9 Izod CKJ / m2) 23 14 11 13 13 Table 3 Example B15 B16 B17 B18 Epoxy resin E6 E7 E8 E9 -27- This paper size applies to China National Standard (CNS) Λ4 Regulation 彳 210 210 x 297 " T " V. Description of the invention (41i347 A7 B7 25 Water absorption Rate (%) 1.1 Peel strength of copper foil (kg / cm) 2.7 Izod (KJ / m2). 20 (Effect of the invention) The compound of the present invention can be used as: Materials such as PEEK, PP〇, Polyfluorene, etc.) are used as raw materials for thermosetting resins (ring! Resins), cyanic acid resins, acetic acid resins, etc., and are used for high-reliability semiconductor packaging. Main electrical and electronic parts insulation materials, and laminated board (printed circuit board) WFRp (carbon fiber Chemical plastics ^ King of various composite materials, adhesives, coatings, molding materials, etc .; Various industrial intermediates ... If the production method of the present invention is used, the formation of by-products can be suppressed. The multivalent test compound of the present invention. 1.1 1.0 1.2 2.7 2.7 2.7 24 17 13 (Please read the notes on the back and fill in this page first) • 1T · Printed by the Consumers ’Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs 4'ls. In addition, the epoxy resin of the present invention is caused by The hardened product has excellent moisture and water resistance), impact resistance, and adhesion. Therefore, it is mainly based on gas and electron zero insulation materials (high reliability semiconductor packaging materials, etc.), laminated boards (printing boards, etc.) or CFRP. A variety of composite materials, adhesives, coatings, etc .: extremely useful, especially when used in semiconductor packaging materials, has excellent cracking properties. The paper size applies to the Chinese National Standard (CN'S) Λ4 specification (210 × 297 mm)

Claims (1)

No. 871l | 〇173 Special Shousen tyan 4 7 Chinese cloth _ revised patent scope (October 88), patent application scope A8 B8 C8 D8 —ifiAJ polyvalent phenol compounds, which are represented by formula (1) 〇H) yr (QH) y \ N / ~ TR iQ) jm iD 2. (where 'X represents an oxygen atom or a sulfur atom' Q represents a hydrogen atom or a carbon atom. 5 alkyl group 'R represents a hydrogen atom, Carbon number M. A hydrocarbon group or alkyl group, i, j, k and y respectively represent an integer of 6, 6 = j ~ 3, 5, 5, y = i ~ 2. N is the average value, a real number of 1M5 ). The polyvalent phenolic compound according to item i of the patent application scope is represented by 33. Base H (R) h (Please read the notes on the back before filling this page) 3. Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs 4. (where X, Q, R, and j represent the same meaning as in the formula (1), and h is an integer from 1 to 4). According to the polyvalent phenolic compound according to item 丨 or 2 of the scope of the applied patent, wherein X in formula 为 is an oxygen atom β, '— a method for preparing a polyvalent phenolic compound, which is characterized by formula ⑻ ~ phenols and CHO (Q) i (S) The size of this paper + ¾¾ Standard (CNS) _ A4 size (210X297 mm) No. 871l | 〇173 Special Shousen tyan 4 7 Chinese cloth _ revised version of patent scope (10 of 88) Month), the scope of patent application A8 B8 C8 D8 —ifiAJ polyvalent phenol compounds, which are represented by formula (0H) yr (QH) y \ N / ~ TR iQ) jm iD 2. (wherein 'X Represents an oxygen atom or a sulfur atom, 'Q represents a hydrogen atom or an alkyl group of carbon 凄 .5', R represents a hydrogen atom, a carbon number of M. A hydrocarbon group or an alkyl group, i, j, k, and y represent bu 6, j, respectively = i ~ 3, bubu5, y = integers from i ~ 2. n is the average value and is a real number of 1M5). The polyvalent phenolic compound according to item i of the patent application scope is represented by 33. Base H (R) h (Please read the notes on the back before filling this page) 3. Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs 4. (where X, Q, R, and j represent the same meaning as in the formula (1), and h is an integer from 1 to 4). According to the polyvalent phenolic compound according to item 丨 or 2 of the scope of the applied patent, wherein X in formula 为 is an oxygen atom β, '— a method for preparing a polyvalent phenolic compound, which is characterized by formula ⑻ ~ phenols and CHO (Q) i (S) The size of this paper + ¾¾ Standard (CNS) _ A4 specification (210X297 mm) 411347 A8 B8 C8 D8 Patent application scope 5. (In the formula, X, (3 and ′) and formula ⑴ The same meaning as in the above) is shown. The compound is condensed in the presence of a test catalyst. * 'The manufacturing method according to item 4 of the scope of patent application, in which 2,6 -dimethylbenzyl. 6. 8. According to the manufacturing method of the applied β patent | a garden spear 4, and 2,5-dimethylphenol. ^ 'According to the manufacturer of any of the patent application scope items 4 ~ 6 t The alkaline catalyst is selected from the group consisting of alkali metal hydroxides and alkaline earth metals; f compounds, alkali metal alkoxides, and alkaline earth metal alkoxides, and more than one species. ≪ S > An epoxy resin , Which is represented by formula (⑶) (〇G) y) (R) i-ι -C- 'X \ N * / V .J (R) k -R (3) (where G is a glycidyl group, and R, Q, and X k are the same as those in formula ⑴ The same meaning). 9. An epoxy resin, which is represented by the formula ⑷, η, y, i, j and (Notes on the back of the poem before you fill out this page j for the Central Standards Bureau employee consumer cooperatives India Chang H (R) nG. Office (Q) i -och2 ^ hch2o OH (In the formula, G, R, Q, X, and j represent the same meanings as in formula (3). M is the average value, which represents a real number of 0 to 20, and h is an integer of Tables 1 to 4.) Applicable to Chinese National Standard (CNS) A4 standard (210X297 mm) 7 4 3 i 1 4 ABCD 6. Application scope of patent-10 · A thermosetting resin composition, which is relative to epoxy group in epoxy resin 1 equivalent, containing 0.5 to 5 equivalents of epoxy resin and the polyvalent phenolic compound in the first scope of the patent application. 11. A thermosetting resin composition comprising 0.5 to 1.5 equivalents of an epoxy resin and a hardener in accordance with the patent application No. 8 with respect to 1 equivalent of the epoxy group in the epoxy resin. 12_ A thermosetting resin composition containing 1 equivalent of epoxy groups in an epoxy resin, containing an epoxy resin in the patent application No. 8 and a polyvalent phenol compound in the patent application No. 1; 5 to 1.5 equivalents. 13. A thermosetting resin composition ', which is based on i equivalent of a cyanate resin, and contains 0 to 1.5 equivalents of a polyvalent phenolic compound and a polyvalent phenolic compound in the range of patent application. —— (Please read the notes on the back before filling out this page) I Printed by the Consumers' Cooperative of the Central Bureau of Standards, Ministry of Economic Affairs This paper size applies to China National Standard (CNS) A4 (210X297 mm)