WO2007007827A1 - Résines phénol novolaque à pont biphénylène et leur utilisation - Google Patents

Résines phénol novolaque à pont biphénylène et leur utilisation Download PDF

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Publication number
WO2007007827A1
WO2007007827A1 PCT/JP2006/313929 JP2006313929W WO2007007827A1 WO 2007007827 A1 WO2007007827 A1 WO 2007007827A1 JP 2006313929 W JP2006313929 W JP 2006313929W WO 2007007827 A1 WO2007007827 A1 WO 2007007827A1
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Prior art keywords
phenol
biphenylene
resin
epoxy resin
integer
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PCT/JP2006/313929
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English (en)
Japanese (ja)
Inventor
Noriyuki Mitani
Maki Kawano
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Ube Industries, Ltd.
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Priority to JP2007524700A priority Critical patent/JP5104308B2/ja
Priority to CN2006800229565A priority patent/CN101208368B/zh
Publication of WO2007007827A1 publication Critical patent/WO2007007827A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L61/00—Compositions of condensation polymers of aldehydes or ketones; Compositions of derivatives of such polymers
    • C08L61/04—Condensation polymers of aldehydes or ketones with phenols only
    • C08L61/06—Condensation polymers of aldehydes or ketones with phenols only of aldehydes with phenols
    • 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
    • C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G61/02—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes
    • C08G61/10—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes only aromatic carbon atoms, e.g. polyphenylenes
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
    • C08G59/62—Alcohols or phenols
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
    • C08G59/62—Alcohols or phenols
    • C08G59/621—Phenols
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins

Definitions

  • the present invention relates to a bicyclodiene cross-linked phenol novolak obtained by reacting bis (alkoxymethyl) biphenyl or bis (methyl halide) biphenyl and a phenol mixture containing at least one divalent phenol. It relates to resin.
  • the phenol novolac resin of the present invention is used as a curing agent for epoxy resins, and can also be used as a raw material for epoxy resin, epoxy resin urethane resin, triazine resin, and polyester resin.
  • phenol novolak resins obtained by reacting bis (alkoxymethyl) biphenyl or bis (norogenated methyl) biphenyl with phenols are bis (methoxymethyl) biphenyl compounds.
  • Patent Document 1 A biphenylen-crosslinked phenol novolak resin using each isomer or a mixture thereof is disclosed.
  • the bi-phenylene cross-linked phenol novolac resin according to the prior art has a problem that the curing rate is slower than the phenol novolac resin. If the curing speed is slow, the curing time will be longer, which will adversely affect the productivity or production cost when used for each application. Therefore, there is a demand for low water absorption (low hygroscopicity), flame retardancy, and high heat resistance, as well as a high curing speed and a biphenylene-crosslinked phenol novolak resin.
  • Patent Document 1 Japanese Patent Application Laid-Open No. 08-143648
  • the object of the present invention is to provide an epoxy resin that has low water absorption (low hygroscopicity), heat resistance, flame retardancy, mechanical properties, and adhesive properties, compared with the conventional biphenylen-crosslinked phenol novolac resin. It is an object of the present invention to provide a biphenylene-crosslinked phenol novolak resin having a fast curing speed of the resin.
  • the present invention relates to the following general formula (2) comprising a reaction product of a biphenyl complex represented by the general formula (1) and a phenol mixture containing at least one divalent phenol. ) Represented by biphenylene cross-linked phenol novolac resin.
  • X represents an alkoxyl group having 1 to 4 carbon atoms or a halogen atom
  • R 2 and R 3 may be the same or different, and a plurality of R 1 and R 3 may be the same or different.
  • a chain or branched alkyl group, a substituted or unsubstituted aryl group, pi and p3 represent an integer of 0 to 4,
  • p2 represents an integer of 0 to 3
  • n represents an integer of 0 to: 15, ml, m2, and m3 each represent an integer of 1 or 2
  • a plurality of m2 may be the same or different, except that ml, m2, and m3 are all 1 or all 2.
  • the biphenylen-crosslinked phenol novolak resin obtained by the method of the present invention has low water absorption (low hygroscopicity), heat resistance, flame retardancy, mechanical properties, and adhesive properties, while being a conventional technique. Is a resin with a faster curing rate of epoxy resin than bilene crosslinked phenol novolac resin, It can contribute to the improvement of productivity.
  • the resin can be used as an epoxy resin by reacting with an epoxy resin curing agent or epichloronohydrin, and further includes a biphenylene cross-linking group as a flame retardant. Can also be used.
  • the phenols used in the present invention are compounds having one hydroxyl group in the benzene ring.
  • the phenols include substituted or unsubstituted phenol, naphthol, and bisphenol.
  • the substituent represented by R 2 and R 3 include a linear or branched alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group, and the like. 1 to 4 of these substituents may be substituted for R 1 and R 3 , and 1 to 3 of R 2 may be substituted.
  • Preferred alkyl groups include linear or branched alkyl groups such as methinole, ethyl, propinole, butyl, hexyl and octyl.
  • Specific examples include phenols: cresol, ethylphenol, n-propylphenol, octylphenol, nourphenol, phenol, monosubstituted phenols; xylenol, methylpropylphenol, dipropylphenol, dibutylphenol Disubstituted phenols such as trimethylphenol; naphthols such as naphthol and methylnaphthol; and bisphenols such as bisphenol, bisphenolanol A, and bisphenol F.
  • phenols are used alone or in combination of two or more.
  • Preferred phenols are unsubstituted phenol and meta-substituted linear or branched alkylphenols having 1 to 4 carbon atoms in view of the reactivity of the phenols, more preferably phenol and m. —Talesol.
  • the divalent phenol used in the present invention is a compound having two hydroxyl groups in the benzene ring. Specific examples include resornoresin, hydroquinone, and force teconore. These divalent phenols may be used alone or in combination of two or more. Resorcin is preferable.
  • resorcin, hydroquinone, and catechol include straight-chain or Although there is no problem even if it has at least one branched alkyl group or substituted or unsubstituted aryl group, it is preferably an unsubstituted compound.
  • the compounds contained in the divalent phenol of the present invention include a compound group having a total of two hydroxyl groups, for example, a bisphenol compound group, each having one hydroxyl group on the benzene ring in the molecule.
  • a bisphenol compound group include bisphenol, bisphenol A, and bisphenol F.
  • divalent phenols can be used alone or in combination of two or more.
  • Preferred are unsubstituted resorcin, hydroquinone, and catechol, and more preferred is unsubstituted resorcin.
  • a mixture of phenols containing at least one component of divalent phenol This is a phenol mixture.
  • the blending ratio of phenols and divalent phenols is not particularly limited. However, the content ratio of the bivalent phenol to 100 mol of the phenol mixture (the total number of moles used of the phenol and the divalent phenol) is preferably 5 to 80 monoreca. More preferably, it is 7 to 70 monolayers, more preferably 10 to 50 monolayers.
  • Bivalent phenol alone can provide a fast vinyl phenyl crosslinked phenol novolak resin with a high curing rate, but is not preferred because it may make it difficult to remove impurities in the resin production process. Furthermore, the disadvantage that the water absorption rate is relatively high is not solved.
  • Examples of the biphenyl compound represented by the following general formula (1) of the present invention include bis (alkoxymethyl) biphenyl and bis (norogenated methyl) biphenyl. These compounds are, for example, forces capable of mentioning isomers of 4, 4 'monolith, 2, 2,-isomers and 2, 4'- isomers, preferably 4, 4'- isomers. There is no problem even if these isomers are used in combination of two or more.
  • the alkoxyl group is preferably an aliphatic linear hydrocarbon alkoxyl group having 1 to 4 carbon atoms. Specific examples thereof include methoxy, ethoxy, propoxy and butoxy, and are easy to handle. Therefore, methoxy is mainly used.
  • a force chlorine atom including a fluorine atom, a chlorine atom, a bromine atom and an iodine atom is preferably used.
  • the bis (alkoxymethyl) biphenyl or bis (halogenated methyl) biphenyl isomer mixture represented by the above general formula (1) of the present invention is not particularly limited in its combination and use amount. However, it is preferable that 4, 4 'integral is contained as a main component.
  • this cross-linking agent can be synthesized by adding all at once or reacting them or by adding them in portions.
  • the batch addition at the time of charging is preferable.
  • the synthetic catalyst of the present invention is an organic acid such as oxalic acid, formic acid, acetic acid, sulfuric acid, p-toluenesulfonic acid, and Friedel-Craft type catalyst such as decyl sulfate. It can be synthesized by polymerization.
  • each isomer of divalent phenol or the amount of the mixture and phenols used is usually the isomer of bis (alkoxymethyl) biphenyl or bis (norogenated methyl) biphenyl.
  • the total amount may be 1.2 times mol or more with respect to the mixture. Preferably it is 1.3-5.5 times mole, More preferably, it is 1.4-4.5 times mole. 1.
  • the amount of the synthesis catalyst used in the present invention is 0.001 to 0.5 parts by weight, preferably 0, based on the total amount of each isomer of divalent phenol or a mixture thereof and phenols. 001-0. 2 parts by weight, more preferably in the range of 0.001-0. 1 parts by weight.
  • the amount used is small, the reaction rate is slow, and when the amount used is too large, the reaction proceeds rapidly and it becomes impossible to control the reaction.
  • the generated hydrogen halide acts as a catalyst, so that a synthesis catalyst may or may not be added.
  • the reaction temperature of the present invention depends on the isomers of the divalent phenol used or a mixture thereof and phenols, and bis (alkoxymethyl) biphenyl or bis (no-rogenated methyl) biphenol as a bridging group. Force depending on the ratio of each isomer mixture of dill. C, preferably 70 to 180. C, more preferably 80 to: 180. C. If the concentration is too low, it becomes difficult to control the reaction, and it becomes difficult to stably obtain the phenol novolak resin of the claims.
  • reaction time in the present invention depends on the reaction temperature, it is usually within 10 hours for addition condensation reaction, demethanol reaction or dehalogenation reaction.
  • reaction pressure in the present invention is usually carried out under normal pressure, but it can also be carried out under slight pressure or reduced pressure.
  • the polystyrene-reduced number average molecular weight (Mn) and weight average molecular weight (Mw) of the biphenylen bridged phenol nopolac resin represented by the general formula (2) obtained under the above reaction conditions are from those having a low molecular weight to those having a high molecular weight.
  • Mn is preferably 350 to 6800, more preferably 500 to 3500, and more preferably 500 to 3000.
  • Mw is preferably 350 to 20000, more preferably 500 to 15,000, and more preferably 500 to 13,000.
  • the repeating frequency n of the biphenylene-crosslinking group of the bibutylene-crosslinked phenol novolak resin represented by the general formula (2) obtained under the above reaction conditions is an integer from 0 to: 15, preferably from 0 to : An integer of 12, more preferably an integer of 0 to 10.
  • the biphenylene cross-linked phenol novolak resin obtained in the present invention can be used as it is as a curing agent for an epoxy resin, or can be made into an epoxy resin by reacting with epichlorohydrin. Furthermore, it can also be set as the hardened
  • epoxy resin examples include bisphenol A type epoxy resin, bisphenol F type epoxy resin, cresol novolac type epoxy resin, phenol novolac type epoxy resin, triphenol methane type epoxy resin, biphenyl type epoxy resin and the like.
  • examples include glycidyl ether type epoxy resins, glycidyl ester type epoxy resins, glycidylamine type epoxy resins, halogenated epoxy resins, and other epoxy resins having two or more epoxy groups in the molecule. These epoxy resins may be used alone or in combination of two or more.
  • Preferred epoxy resins include cresol novolac type epoxy resins and biphenyl type epoxy resins.
  • a known curing accelerator for curing an epoxy resin with a phenol resin can be used.
  • tetraphenyl phosphonium derivatives such as tetraphenyl phosphonium 'tetraphenyl pololeate, which are preferred to be heat-latent curing accelerators that exhibit activity upon heat treatment, are preferred. Is preferred.
  • the desired epoxy resin can be obtained by dissolving the residue in an organic solvent such as methylisobutyl ketone, filtering, washing with water to remove the inorganic salt, and then distilling off the organic solvent.
  • organic solvent such as methylisobutyl ketone
  • a new epoxy resin composition can be obtained using the epoxy resin thus obtained and the biphenylene-crosslinked phenol novolak resin as a curing agent.
  • the obtained epoxy resin composition can be used by adding or reacting in advance with an inorganic filler, a release agent, a colorant, a coupling agent, a flame retardant, and the like, if necessary.
  • an inorganic filler when used for semiconductor sealing applications, the addition of inorganic fillers is essential.
  • examples of such inorganic fillers include amorphous silica, crystalline silica, alumina, calcium silicate, calcium carbonate, talc, my strength, barium sulfate, etc.
  • amorphous silica, crystalline Preferred is silica.
  • the blending ratio of these additives may be the same as the ratio in the known semiconductor sealing epoxy resin composition.
  • the temperature was raised to C and unreacted components were removed by vacuum steaming treatment, and the resulting resin had a soft spot of 65.3 ° C.
  • Gel permeation chromatographic analysis hereinafter abbreviated as GPC.
  • the polystyrene equivalent number average molecular weight (Mn) was 773 and the weight average molecular weight (Mw) was 920.
  • Thermometer charging ⁇ Glass with a capacity of 1000 parts, equipped with a distillation outlet, a condenser and a stirrer Flasks made of this material (16.68 Monoles), Reso 'Noresin 22 (0.2 Monole), 4, 4, —Bismethoxymethinorebiphenol 112. 63 ⁇ 4 (0.465 Monole) and 50 put weight 0/0 sulfuric 0.
  • a 1000-volume glass flask equipped with a thermometer, charging / distilling outlet, condenser and stirrer Kofenore 169.2 2 (1.8 monole), nodroquinone 11 (0.1 monole), cateconore 11 ⁇ (0.1 monole), 4, 4, _bismethoxymethylenorebifeninore 112. 63 ⁇ 4 (0.465 mol) and 50 wt% sulfuric acid Then, the reaction was carried out at an internal temperature of 110 ° C to 140 ° C for 3 hours and further at 165 ° C for 3 hours, and cooled to 95 ° C.
  • the softening point of the obtained resin was 70.9 ° C.
  • the number average molecular weight (Mn) in terms of polystyrene was 725, and the weight average molecular weight (Mw) was 858.
  • Thermometer charging ⁇ Glass with a capacity of 1000 parts, equipped with a distillation outlet, a condenser and a stirrer Flasks made of this product (Konoenore 178. 63 ⁇ 4 (1.90 monole), Reso 'noresin ll (0.10 monole), 4, 4, _bismethoxymethinorebifeninore 112. 63 ⁇ 4 (0.465 monole) and 50 ⁇ / ⁇ Sulfuric acid 0.1. Put 10 ⁇ into a 4-necked flask and react under nitrogen flow at an internal temperature of 110 ° C ⁇ : 140 ° C for 3 hours and then at 165 ° C for 3 hours until 95 ° C.
  • the softening point of the obtained resin was 74 ° C.
  • the polystyrene equivalent number average molecular weight (Mn) by GPC was 811 and the weight average molecular weight (Mw) was 1005.
  • the internal temperature was raised to 160 ° C, and unreacted components were removed by a vacuum steaming process.
  • the softness point of the obtained resin was 97 ° C.
  • the number average molecular weight (Mn) in terms of polystyrene by GPC was 912, and the weight average molecular weight (Mw) was 1127.
  • the inner temperature 110 ° C ⁇ Reaction was carried out at 140 ° C for 3 hours and further at 165 ° C for 3 hours, and cooled to 95 ° C.
  • the softness point of the obtained resin was 90.3 ° C.
  • the number average molecular weight (Mn) in terms of polystyrene by GPC was 925, and the weight average molecular weight (Mw) was 1180.
  • the internal temperature was raised to 160 ° C, and unreacted components were removed by decompression-steaming treatment, and the resulting resin had a soft spot of 73.0 ° C.
  • the average molecular weight (Mn) was 822 and the weight average molecular weight (Mw) was 957.
  • the internal temperature was raised to 160 ° C, and unreacted components were removed by a reduced pressure one steaming process.
  • the softening point of the obtained resin was 78.0 ° C.
  • the number average molecular weight (Mn) in terms of polystyrene by GPC was 882, and the weight average molecular weight (Mw) was 1171.
  • the internal temperature was raised to 160 ° C., and unreacted components were removed by a reduced pressure one steaming process.
  • the softening point of the obtained resin was 74 ° C.
  • the number average molecular weight (Mn) in terms of polystyrene by GPC was 915, and the weight average molecular weight (Mw) was 1191.
  • the internal temperature was raised to 160 ° C., and unreacted components were removed by decompression treatment.
  • the softening point of the obtained resin was 95 ° C.
  • the number average molecular weight (Mn) in terms of polystyrene by GPC was 891, and the weight average molecular weight (Mw) was 1038.
  • the analysis method of the resin and the curing agent obtained in the present invention is as follows.
  • ImolZL potassium hydroxide amount [ml] required for sample measurement
  • Measuring device Set sample on TMA_60 (manufactured by SHIMADZU) and measure in N atmosphere.
  • Tg glass transition temperature
  • Table 1 shows the physical properties of phenol novolak resins synthesized according to the above examples:! To 11 and comparative examples:! To 3.
  • each phenol novolak resin in Table 1 the epoxy resin Nippon Kayaku Co. E_ ⁇ _CN_ 10 2 ⁇ _ 7 0 (epoxy equivalent l ⁇ g / eq), a curing accelerator Triphenylphosphine was used as Compounded in the same equivalent ratio as the above epoxy resin, heated to 150 ° C, melt mixed, cast in a mold heated to 150 ° C after vacuum degassing, and at 150 ° C for 5 hours, 180 ° Cured with C for 3 hours to obtain a cured epoxy resin.
  • Table 2 shows the composition and physical properties of the resulting cured epoxy resin.
  • Each phenol novolak resin in Table 1 was used as a curing agent, Epoxy Coat YX-4000 (epoxy equivalent 187 g / eq) manufactured by Japan Epoxy Resin Co., Ltd. as an epoxy resin, and Triphenylphosphine as a curing accelerator. used. Compounded at the same equivalent ratio as the above epoxy resin, heated to 150 ° C, melted and mixed, cast into a mold heated to 150 ° C after vacuum degassing, and 180 ° C for 5 hours at 150 ° C. Cured with C for 3 hours to obtain a cured epoxy resin. Table 3 shows the composition and physical properties of the cured epoxy resin.
  • Biphenylene bridging group monobismethoxymethylbiphenyl monobischloromethylbiphenyl (
  • the epoxy resin can be used in comparison with the conventional biphenylen-crosslinked phenol novolac resin.
  • a biphenylene-crosslinked phenol novolac resin having a high curing rate can be provided.
  • the biphenylene cross-linked phenol novolak resin of the present invention can be used as an epoxy resin by reacting with epichlorohydrin, and further includes a biphenylene cross-linking group, so that it is also used as a flame retardant. be able to.

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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)
  • Epoxy Resins (AREA)
  • Phenolic Resins Or Amino Resins (AREA)
  • Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)

Abstract

La présente invention concerne des résines phénol novolaque à pont biphénylène représentées par la formule générale (2). Lesdites résines consistent en produits de la réaction entre un composé biphényle représenté par la formule générale (1) et un mélange de phénols contenant au moins un phénol dihydrique : (1) (dans laquelle X est un alcoxy ayant de 1 à 4 atomes de carbone ou un halogéno) (2) (dans laquelle R1, R2 et R3 sont chacun indépendamment un alkyle substitué ou non substitué, linéaire ou ramifié ayant de 1 à 10 atomes de carbone ou un aryle substitué ou non substitué, à condition que les R1, R2 et R3 soient chacun identiques ou différents les uns des autres ; p1 et p3 sont chacun un nombre entier de 1 à 4 ; p2 est un nombre entier de 1 à 3 ; n est un nombre entier de 0 à 15 ; m1, m2 et m3 sont chacun un nombre entier égal à 1 ou 2 et les m2 peuvent être identiques ou différents les uns des autres, en exceptant le cas où m1, m2 et m3 sont tous égaux à 1 et le cas où m1, m2 et m3 sont tous égaux à 2).
PCT/JP2006/313929 2005-07-13 2006-07-13 Résines phénol novolaque à pont biphénylène et leur utilisation WO2007007827A1 (fr)

Priority Applications (2)

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JP2007524700A JP5104308B2 (ja) 2005-07-13 2006-07-13 ビフェニレン架橋フェノールノボラック樹脂ならびにその用途
CN2006800229565A CN101208368B (zh) 2005-07-13 2006-07-13 亚联苯基交联线型酚醛树脂及其用途

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JP2005-203746 2005-07-13

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