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WO2013039185A1 - Composé de benzoxazine et son procédé de fabrication - Google Patents

Composé de benzoxazine et son procédé de fabrication Download PDF

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Publication number
WO2013039185A1
WO2013039185A1 PCT/JP2012/073558 JP2012073558W WO2013039185A1 WO 2013039185 A1 WO2013039185 A1 WO 2013039185A1 JP 2012073558 W JP2012073558 W JP 2012073558W WO 2013039185 A1 WO2013039185 A1 WO 2013039185A1
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WO
WIPO (PCT)
Prior art keywords
dihydro
formula
group
benzoxazin
carbon atoms
Prior art date
Application number
PCT/JP2012/073558
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English (en)
Japanese (ja)
Inventor
泰裕 片岡
Original Assignee
住友化学株式会社
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 住友化学株式会社 filed Critical 住友化学株式会社
Publication of WO2013039185A1 publication Critical patent/WO2013039185A1/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
    • C08G14/00—Condensation polymers of aldehydes or ketones with two or more other monomers covered by at least two of the groups C08G8/00 - C08G12/00
    • C08G14/02—Condensation polymers of aldehydes or ketones with two or more other monomers covered by at least two of the groups C08G8/00 - C08G12/00 of aldehydes
    • C08G14/04—Condensation polymers of aldehydes or ketones with two or more other monomers covered by at least two of the groups C08G8/00 - C08G12/00 of aldehydes with phenols
    • C08G14/06—Condensation polymers of aldehydes or ketones with two or more other monomers covered by at least two of the groups C08G8/00 - C08G12/00 of aldehydes with phenols and monomers containing hydrogen attached to nitrogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
    • C07D265/04—1,3-Oxazines; Hydrogenated 1,3-oxazines
    • C07D265/12—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems
    • C07D265/14—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring
    • C07D265/16—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring with only hydrogen or carbon atoms directly attached in positions 2 and 4
    • 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
    • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
    • C08G73/02—Polyamines
    • C08G73/0233—Polyamines derived from (poly)oxazolines, (poly)oxazines or having pendant acyl groups
    • 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
    • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
    • C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule

Definitions

  • the present invention relates to a benzoxazine compound and a method for producing the same.
  • Ring-opening polymerization proceeds by heating the benzoxazine compound, specifically 2,2-bis (3,4-dihydro-3-phenyl-1,3-benzoxazine) propane, at a low temperature, and the benzoxazine compound is cured and cured. It is known to produce a cured oxazine resin (Japanese Patent Laid-Open No. 2000-178332).
  • the present invention includes the following inventions.
  • Formula (1) (In the formula, X represents the formula (A-1), the formula (A-2) or the formula (A-3).
  • Represents a group represented by R 1 to R 25 each independently represents a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an alkyloxy group having 1 to 6 carbon atoms, a halogen atom, or a cyano group.
  • R 1 and Y 2 each independently represent an alkyl group having 1 to 6 carbon atoms or a phenyl group which may be substituted with an alkyl group having 1 to 4 carbon atoms.
  • Y 1 and Y 2 each independently represent an alkyl group having 1 to 6 carbon atoms or a phenyl group which may be substituted with an alkyl group having 1 to 4 carbon atoms.
  • a process comprising reacting a primary amine compound represented by formula and formaldehyde in the presence of a base.
  • the compounds of the present invention have the formula (1) (In the formula, X represents the formula (A-1), the formula (A-2) or the formula (A-3).
  • R 1 and Y 2 each independently represent an alkyl group having 1 to 6 carbon atoms or a phenyl group which may be substituted with an alkyl group having 1 to 4 carbon atoms.
  • Preferable X includes a group represented by formula (A-1) or formula (A-2).
  • alkyl group having 1 to 6 carbon atoms include methyl group, ethyl group, n-propyl group, isopropyl group, t-butyl group, n-hexyl group and cyclohexyl group.
  • alkyloxy group having 1 to 6 carbon atoms include methoxy group, ethoxy group, n-propoxy group, isopropoxy group, t-butoxy group, n-hexyloxy group and cyclohexyloxy group.
  • halogen atom examples include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.
  • phenyl group that may be substituted with an alkyl group having 1 to 4 carbon atoms include a phenyl group, an o-toluyl group, an m-toluyl group, a p-toluyl group, a 4-isopropylphenyl group, and a 4-t-butylphenyl group. Is mentioned.
  • Examples of the compound of the present invention include 1,4-bis (3,4-dihydro-3-phenyl-1,3-benzoxazin-6-yl) benzene, 1- (3,4-dihydro-8-methyl-3). -Phenyl-1,3-benzoxazin-6-yl) -4- (3,4-dihydro-3-phenyl-1,3-benzoxazin-6-yl) benzene, 1- (3,4-dihydro- 8-ethyl-3-phenyl-1,3-benzoxazin-6-yl) -4- (3,4-dihydro-3-phenyl-1,3-benzoxazin-6-yl) benzene, 1- (3 , 4-Dihydro-8-isopropyl-3-phenyl-1,3-benzoxazin-6-yl) -4- (3,4-dihydro-3-phenyl-1,3-benzoxazin-6-yl) benzene
  • the compound of the present invention has the formula (4) (Wherein R 1 to R 6 and X have the same meaning as described above.)
  • a bisphenol compound represented by the formula (hereinafter sometimes referred to as bisphenol compound (4)), formula (5) Y 1 —NH 2 (5) (In the formula, Y 1 represents the same meaning as described above.)
  • a primary amine compound represented by: Formula (6) Y 2 —NH 2 (6) (Where Y 2 represents the same meaning as described above) Can be produced by a production method including a step of reacting a primary amine compound and formaldehyde represented by the above in the presence of a base.
  • Examples of the bisphenol compound (4) include 1,4-bis (4-hydroxyphenyl) benzene, 1,4-bis (4-hydroxyphenyl) cyclohexene, 1,4-bis (4-hydroxyphenyl) cyclohexane, 1- ( 3-methyl-4-hydroxyphenyl) -4- (4-hydroxyphenyl) benzene, 1- (3-methyl-4-hydroxyphenyl) -4- (4-hydroxyphenyl) cyclohexene, 1- (3-methyl- 4-hydroxyphenyl) -4- (4-hydroxyphenyl) cyclohexane, 1- (3-ethyl-4-hydroxyphenyl) -4- (4-hydroxyphenyl) benzene, 1- (3-ethyl-4-hydroxyphenyl) ) -4- (4-hydroxyphenyl) cyclohexene, 1- (3-ethyl-4-hydroxyphene) L) -4- (4-hydroxyphenyl) cyclohexane, 1- (3-isopropyl-4-hydroxy
  • the bisphenol compound (4) can be produced by the methods described in JP 2002-308808 A, JP 2002-308809 A, and JP 2002-363117 A.
  • Examples of the primary amine compound represented by the formula (5) and the primary amine compound represented by the formula (6) include methylamine, ethylamine, n-propylamine, isopropylamine, n-butylamine, t-butylamine, and n-hexyl. Examples include amines, cyclohexylamine, aniline, o-toluidine, m-toluidine, p-toluidine, 4-isopropylaniline, and 4-t-butylaniline.
  • the amount of the primary amine compound represented by the formula (5) and the primary amine compound represented by the formula (6) is usually 1 to 20 moles per 1 mole of the bisphenol compound (5), respectively.
  • the amount is preferably 1.5 mol to 10 mol, more preferably 1.8 mol to 5 mol.
  • Formaldehyde includes formaldehyde aqueous solution, 1,3,5-trioxane, and paraformaldehyde.
  • the amount of formaldehyde used is usually 2 to 100 moles, preferably 3 to 20 moles, more preferably 3.5 to 10 moles with respect to 1 mole of the bisphenol compound (4). .
  • Bases include alkali metal hydroxides such as sodium hydroxide and potassium hydroxide; alkaline earth metal hydroxides such as calcium hydroxide and barium hydroxide; alkali metal carbonates such as sodium carbonate and potassium carbonate; hydrogen carbonate Alkali metal hydrogen carbonates such as sodium and potassium hydrogen carbonate; triethylamine, diisopropylethylamine, dipropylamine, dibutylamine, tributylamine, pyrrolidine, piperidine, diamylamine, dicyclohexylamine, tripropylamine and 1,8-diazabicyclo [5,4 , 0] secondary or tertiary amines such as undec-7-ene; basic nitrogen-containing heterocyclic compounds such as pyridine and imidazole.
  • alkali metal hydroxides such as sodium hydroxide and potassium hydroxide
  • alkaline earth metal hydroxides such as calcium hydroxide and barium hydroxide
  • alkali metal carbonates such as sodium carbon
  • the amount of the base used is usually from 0.001 mol to 100 mol, preferably from 0.005 mol to 20 mol, more preferably from 0.01 mol to 1 mol, relative to 1 mol of the bisphenol compound (4). 10 moles.
  • the base When the base is a liquid, the base may be used as a solvent, and the amount of the base used in that case is not particularly limited.
  • the reaction is usually carried out in the presence of a solvent. The solvent may be refluxed during the reaction.
  • Solvents include alcohol solvents such as methanol, ethanol, isopropyl alcohol, n-butyl alcohol, n-hexyl alcohol and cyclohexyl alcohol; ether solvents such as tetrahydrofuran, dioxane and dimethoxyethane; aliphatics such as toluene, xylene and benzene Hydrocarbon solvents; aprotic polar solvents such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylpyrrolidinone and dimethyl sulfoxide; nitrile solvents such as acetonitrile and benzonitrile; dichloromethane, chloroform, 1,2- Halogenated hydrocarbon solvents such as dichloroethane, carbon tetrachloride and chlorobenzene; water; and the like.
  • alcohol solvents such as methanol, ethanol, isopropyl alcohol, n-butyl alcohol, n-
  • the solvent a plurality of types of solvents may be mixed and used. Further, as described above, a base may be used as a solvent.
  • the reaction may be carried out under normal pressure conditions, under pressure conditions, or under reduced pressure conditions. Moreover, you may carry out in inert gas atmosphere, such as nitrogen gas and argon gas.
  • the reaction temperature is usually 0 ° C. to 150 ° C., preferably 20 ° C. to 120 ° C., and more preferably 40 ° C. to 100 ° C.
  • the reaction can be followed by measurement such as liquid chromatography. It is preferable to carry out the reaction until an increase in the compound of the present invention or a decrease in the bisphenol compound (4) is not observed.
  • the reaction time is usually 1 hour to 100 hours.
  • the compound of the present invention can be obtained by subjecting the resulting reaction mass to concentration treatment and / or filtration treatment.
  • the taken-out compound of the present invention can be further purified by ordinary purification means such as washing with a solvent and recrystallization.
  • the resin cured product of the present invention is obtained by thermally curing the compound of the present invention.
  • the resin cured product of the present invention may be a resin cured product obtained by curing one kind of the compound of the present invention, or a resin cured product obtained by curing a mixture of two or more different compounds of the present invention. It may be a thing.
  • the method for producing the cured resin product of the present invention (a) a method in which the compound of the present invention is heated to a predetermined temperature and cured, (b) the compound of the present invention is heated and melted and poured into a mold, etc. Examples include a method in which the mold is further heated and cured, and (c) a method in which a melt of the compound of the present invention is injected into a preheated mold and cured.
  • ADVANTAGE OF THE INVENTION According to this invention, it is possible to provide the benzoxazine compound used as the raw material used in order to manufacture the benzoxazine resin hardened
  • the thermal diffusivity was measured by the TWA method (thermal phase diffusivity measuring device, Eye Phase Mobile, manufactured by Eye Phase Co., Ltd.).
  • Example 1 5.00 g of 1- (3-methyl-4-hydroxyphenyl) -4- (4-hydroxyphenyl) benzene, 0.092 g of potassium hydroxide, 10.0 g of methanol and 3.37 g of aniline were charged to an internal temperature of 5 ° C. After cooling and charging 5.88 g of 37% aqueous formaldehyde solution, the mixture was reacted for 23 hours under reflux conditions.
  • Example 3 1- (3,4-Dihydro-8-methyl-3-phenyl-1,3-benzoxazin-6-yl) -4- (3,4-dihydro-3-phenyl-1) obtained in Example 1 , 3-Benzoxazin-6-yl) benzene 0.8 g was spread on an aluminum plate and degassed with a vacuum heating apparatus at 170 ° C. for 1 hour 30 minutes. Then, this was heated up to 190 degreeC, and also heat-cured by heat-retaining at 190 degreeC for 4 hours, and the brown benzoxazine resin hardened
  • Example 4 3-Benzoxazin-6-yl) cyclohexene was spread on an aluminum plate and degassed with a vacuum heating apparatus at 150 ° C. for 1 hour.
  • the present invention it is possible to manufacture and provide a cured benzoxazine resin having a higher thermal conductivity.
  • ADVANTAGE OF THE INVENTION it is possible to provide the benzoxazine compound used as the raw material used in order to manufacture the benzoxazine resin hardened
  • the cured benzoxazine resin is useful as an insulating material that requires heat dissipation.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Phenolic Resins Or Amino Resins (AREA)

Abstract

La présente invention concerne un composé de benzoxazine représenté par la formule (1) (dans laquelle X représente un groupe représenté par la formule (A-1), la formule (A-2) ou la formule (A-3); R1 à R25 représentent chacun indépendamment un atome d'hydrogène, un groupe alkyle en C1 à C6, un groupe alkyloxy en C1 à C6, un atome d'halogène, ou un groupe cyano; et Y1 et Y2 représentent chacun indépendamment un groupe alkyle en C1 à C6 ou un groupe phényle qui peut être substitué par un groupe alkyle en C1 à C4).
PCT/JP2012/073558 2011-09-15 2012-09-07 Composé de benzoxazine et son procédé de fabrication WO2013039185A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2011-201522 2011-09-15
JP2011201522A JP2013060407A (ja) 2011-09-15 2011-09-15 ベンゾオキサジン化合物およびその製造方法

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN108484519A (zh) * 2018-02-05 2018-09-04 中国科学院宁波材料技术与工程研究所 一种基于厚朴衍生物的苯并恶嗪树脂单体及其制备方法和应用
CN113150229A (zh) * 2021-04-12 2021-07-23 中北大学 一种高残碳含氟吡啶型苯并噁嗪树脂及其制备方法

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CN102516194B (zh) * 2011-10-18 2014-08-13 广东生益科技股份有限公司 苯并噁嗪中间体及其制备方法
PT3450499T (pt) 2016-04-28 2024-01-12 Jxtg Nippon Oil & Energy Corp Composição de resina curável e produto curado obtido a partir da mesma
JP6849698B2 (ja) 2016-12-09 2021-03-24 Ｅｎｅｏｓ株式会社 硬化樹脂用組成物、該硬化樹脂用組成物の硬化物及び硬化方法、並びに半導体装置
WO2018181857A1 (fr) 2017-03-31 2018-10-04 Ｊｘｔｇエネルギー株式会社 Composition de résine durcissable, produit durci de ladite composition, procédé de production de ladite composition et dudit produit durci, et dispositif à semi-conducteur
CN111278883B (zh) 2017-10-27 2022-12-30 Jxtg能源株式会社 固化树脂用组合物、该组合物的固化物、该组合物和该固化物的制造方法、以及半导体装置
CN111278882B (zh) 2017-10-27 2022-12-30 Jxtg能源株式会社 固化树脂用组合物、该组合物的固化物、该组合物和该固化物的制造方法、以及半导体装置
CN111278884B (zh) 2017-10-27 2022-12-30 Jxtg能源株式会社 固化树脂用组合物、该组合物的固化物、该组合物和该固化物的制造方法、以及半导体装置
US20220106437A1 (en) 2018-12-10 2022-04-07 Eneos Corporation Composition for curable resin, cured product of said composition, production method for said composition and said cured product, and semiconductor device
JP7569784B2 (ja) 2019-04-26 2024-10-18 株式会社Ｅｎｅｏｓマテリアル 硬化樹脂用組成物、該組成物の硬化物、該組成物および該硬化物の製造方法、ならびに半導体装置
JP2022013415A (ja) * 2020-07-03 2022-01-18 Ｅｎｅｏｓ株式会社 ベンゾオキサジン化合物含有混合物の製造方法
JP2022013410A (ja) * 2020-07-03 2022-01-18 Ｅｎｅｏｓ株式会社 ベンゾオキサジン化合物含有混合物、これを含む硬化性組成物および該硬化性組成物を硬化させてなる硬化物

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JP2006306778A (ja) * 2005-04-28 2006-11-09 Yokohama Rubber Co Ltd:The 新規化合物およびそれを用いた硬化性樹脂組成物
WO2008123237A1 (fr) * 2007-03-26 2008-10-16 Sumitomo Chemical Company, Limited Composition de résine époxy

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JPH1171498A (ja) * 1997-05-01 1999-03-16 Advanced Ceramics Corp 高熱伝導性ポリベンゾオキサジン系材料を形成させるための組成物およびその製造法
JP2006306778A (ja) * 2005-04-28 2006-11-09 Yokohama Rubber Co Ltd:The 新規化合物およびそれを用いた硬化性樹脂組成物
WO2008123237A1 (fr) * 2007-03-26 2008-10-16 Sumitomo Chemical Company, Limited Composition de résine époxy

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN108484519A (zh) * 2018-02-05 2018-09-04 中国科学院宁波材料技术与工程研究所 一种基于厚朴衍生物的苯并恶嗪树脂单体及其制备方法和应用
CN108484519B (zh) * 2018-02-05 2019-12-03 中国科学院宁波材料技术与工程研究所 一种基于厚朴衍生物的苯并恶嗪树脂单体及其制备方法和应用
CN113150229A (zh) * 2021-04-12 2021-07-23 中北大学 一种高残碳含氟吡啶型苯并噁嗪树脂及其制备方法
CN113150229B (zh) * 2021-04-12 2022-07-05 中北大学 一种高残碳含氟吡啶型苯并噁嗪树脂及其制备方法

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