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WO2011058756A1 - Composé polyamide et composition de résine époxy le contenant - Google Patents

Composé polyamide et composition de résine époxy le contenant Download PDF

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Publication number
WO2011058756A1
WO2011058756A1 PCT/JP2010/006652 JP2010006652W WO2011058756A1 WO 2011058756 A1 WO2011058756 A1 WO 2011058756A1 JP 2010006652 W JP2010006652 W JP 2010006652W WO 2011058756 A1 WO2011058756 A1 WO 2011058756A1
Authority
WO
WIPO (PCT)
Prior art keywords
epoxy resin
polyamide compound
resin composition
compound
group
Prior art date
Legal status (The legal status 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 status listed.)
Ceased
Application number
PCT/JP2010/006652
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English (en)
Japanese (ja)
Inventor
齋尾佳秀
高畑義徳
森貴裕
柏崎史
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Adeka Corp
Original Assignee
Adeka Corp
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 Adeka Corp filed Critical Adeka Corp
Priority to KR1020127010350A priority Critical patent/KR101740081B1/ko
Priority to CN201080047345.2A priority patent/CN102575004B/zh
Publication of WO2011058756A1 publication Critical patent/WO2011058756A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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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
    • C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
    • C08G69/02—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids
    • C08G69/26—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from polyamines and polycarboxylic acids
    • C08G69/32—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from polyamines and polycarboxylic acids from aromatic diamines and aromatic dicarboxylic acids with both amino and carboxylic groups aromatically bound
    • 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
    • C08G59/44—Amides
    • 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
    • C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
    • C08G69/42—Polyamides containing atoms other than carbon, hydrogen, oxygen, and nitrogen
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J3/00—Processes of treating or compounding macromolecular substances
    • C08J3/20—Compounding polymers with additives, e.g. colouring
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/01—Use of inorganic substances as compounding ingredients characterized by their specific function
    • C08K3/016—Flame-proofing or flame-retarding additives
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/49—Phosphorus-containing compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/49—Phosphorus-containing compounds
    • C08K5/5399—Phosphorus bound to nitrogen
    • 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
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L77/00—Compositions of polyamides obtained by reactions forming a carboxylic amide link in the main chain; Compositions of derivatives of such polymers
    • C08L77/10—Polyamides derived from aromatically bound amino and carboxyl groups of amino-carboxylic acids or of polyamines and polycarboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/34—Silicon-containing compounds
    • C08K3/36—Silica
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L81/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing sulfur with or without nitrogen, oxygen or carbon only; Compositions of polysulfones; Compositions of derivatives of such polymers
    • C08L81/06—Polysulfones; Polyethersulfones

Definitions

  • the present invention relates to a novel polyamide compound and an epoxy resin composition containing the same, and in particular, a novel polyamide compound having a specific structure in a repeating unit, and a build-up type insulating material containing the same It is related with the epoxy resin composition suitable for.
  • Epoxy resins have been widely used in printed wiring boards because of their excellent insulating properties, dimensional accuracy, and strength, and are particularly excellent in high glass transition temperature, low linear expansion coefficient, flexibility, etc. From the viewpoint of obtaining a cured product, it has been proposed to use a polyamide compound having a phenolic hydroxyl group as a curing agent (Patent Document 1).
  • thermosetting that can maintain a high peel strength for a surface with a small surface roughness.
  • mold insulating resins there is a need for mold insulating resins.
  • the tensile strength of the resin decreases as the amount of filler added increases. Arise. Therefore, the linear expansibility must be reduced without increasing the amount of filler to be blended, but no such material has yet been found.
  • a first object of the present invention is to provide a curing agent capable of imparting high peel strength to a surface having a small surface roughness to an epoxy resin without increasing the blending amount of the filler. is there.
  • the second object of the present invention is to provide an epoxy resin composition having a high peel strength with respect to a surface having a small surface roughness.
  • the present inventors function as a curing agent capable of imparting high peel strength to a surface with a small surface roughness to the epoxy resin.
  • a novel polyamide compound has been found and the present invention has been reached.
  • the present invention provides a polyamide compound having a partial structure represented by the following general formula (I) and / or general formula (I ′) in a repeating unit, and an epoxy containing the polyamide compound It is a resin composition.
  • X in the above general formula represents a hydrogen atom or a hydroxyl group.
  • the polyamide compound of the present invention may have a partial structure represented by the following general formula (II) in addition to the partial structure having a sulfone bond in the repeating unit.
  • the polyamide compound of the present invention may have a partial structure represented by the following general formula (II ′) in addition to the partial structure having a sulfone bond in the repeating unit.
  • the polyamide compound of the present invention is particularly a polyamide compound comprising a diamine compound and a dicarboxylic acid compound, and the diamine compound is 3,3′-diaminodiphenylsulfone alone or 3,3′-diaminodiphenylsulfone and 2,3 Preferably it consists only of 4-diaminophenol.
  • the epoxy resin composition of the present invention needs to contain 1 to 100 parts by mass of the polyamide compound of the present invention with respect to 100 parts by mass of the epoxy resin, and has an average particle size of 0.01 to 20 ⁇ m as a filler. It is preferable to further contain spherical silica and / or a phosphorus-based flame retardant.
  • the amount of the phosphorus-based flame retardant used is preferably 5 to 100 parts by mass with respect to 100 parts by mass in total of the epoxy resin and the polyamide compound.
  • thermosetting epoxy resin composition having high peel strength for a surface having a small surface roughness and suitable as a build-up type insulating resin material Things are obtained.
  • the polyamide compound of the present invention is a polyamide compound obtained by reacting a diamine compound containing 3,3'-diaminodiphenylsulfone as a main component with a dicarboxylic acid compound, and is not described in any literature.
  • various diamine compounds can be used in combination with the 3,3'-diaminodiphenylsulfone.
  • polyamide compound of the present invention is specifically exemplified, but the present invention is not limited to these specific examples.
  • the polyamide compound of the present invention is useful as a curing agent for an epoxy resin.
  • an epoxy resin By containing 1 to 100 parts by mass, preferably 5 to 80 parts by mass of the polyamide compound of the present invention with respect to 100 parts by mass of the epoxy resin, a small surface is obtained.
  • a thermosetting epoxy resin composition having a high peel strength with respect to the surface having roughness can be obtained.
  • the epoxy resin used in the epoxy resin composition of the present invention is not particularly limited, and can be appropriately selected from known aromatic epoxy compounds, alicyclic epoxy compounds, aliphatic epoxy compounds, and the like.
  • aromatic epoxy compound include hydroquinone, resorcinol, bisphenol A, bisphenol F, 4,4′-dihydroxybiphenyl, novolac, tetrabromobisphenol A, 2,2-bis (4-hydroxyphenyl) -1,1,
  • Examples thereof include glycidyl ether compounds of polyhydric phenols such as 1,3,3,3-hexafluoropropane.
  • Examples of the alicyclic epoxy compound include polyglycidyl ether of a polyhydric alcohol having at least one alicyclic ring, or cyclohexene oxide or cyclopentene obtained by epoxidizing a cyclohexene or cyclopentene ring-containing compound with an oxidizing agent.
  • An oxide containing compound is mentioned.
  • hydrogenated bisphenol A diglycidyl ether 3,4-epoxycyclohexylmethyl-3,4-epoxycyclohexylcarboxylate, 3,4-epoxy-1-methylcyclohexyl-3,4-epoxy-1-methylhexanecarboxylate 6-methyl-3,4-epoxycyclohexylmethyl-6-methyl-3,4-epoxycyclohexanecarboxylate, 3,4-epoxy-3-methylcyclohexylmethyl-3,4-epoxy-3-methylcyclohexanecarboxylate 3,4-epoxy-5-methylcyclohexylmethyl-3,4-epoxy-5-methylcyclohexanecarboxylate; bis (3,4-epoxycyclohexylmethyl) adipate, methylenebis (3,4-epoxycyclohexa ), 2,2-bis (3,4-epoxycyclohexyl) propane, dicyclopentadiene
  • aliphatic epoxy compound examples include polyglycidyl ether of aliphatic polyhydric alcohol or its alkylene oxide adduct, polyglycidyl ester of aliphatic long-chain polybasic acid, homopolymer synthesized by vinyl polymerization of glycidyl acrylate or glycidyl methacrylate; glycidyl acrylate Or the copolymer etc. which were synthesize
  • Typical compounds include 1,4-butanediol diglycidyl ether, 1,6-hexanediol diglycidyl ether, glycerin triglycidyl ether, trimethylolpropane triglycidyl ether, sorbitol tetraglycidyl ether, dipentaerythritol.
  • Glycidyl ethers of polyhydric alcohols such as hexaglycidyl ether of polyethylene glycol, diglycidyl ether of polyethylene glycol, diglycidyl ether of polypropylene glycol; one or more of aliphatic polyhydric alcohols such as propylene glycol, trimethylolpropane and glycerin Polyglycidyl ether of polyether polyol obtained by adding an alkylene oxide of diglycidyl ester of aliphatic long chain dibasic acid It is.
  • latent curing agent examples include dicyandiamide, hydrazide, imidazole compound, amine adduct, ketimine, and tertiary amine.
  • polyamine compound examples include aliphatic polyamines such as ethylenediamine, diethylenetriamine, and triethylenetetramine; mensendiamine, isophoronediamine, bis (4-amino-3-methylcyclohexyl) methane, bis (aminomethyl) cyclohexane, 3, Alicyclic polyamines such as 9-bis (3-aminopropyl) 2,4,8,10-tetraoxaspiro [5,5] undecane; aliphatic amines having an aromatic ring such as m-xylylenediamine; Phenylenediamine, 2,2-bis (4-aminophenyl) propane, diaminodiphenylmethane, diaminodiphenylsulfone, ⁇ , ⁇ -bis (4-aminophenyl) -p-diisopropylbenzene, 2,2-bis (4-aminophenyl) ) -1,1,1,3,3,3-hexa
  • polyphenol compound examples include phenol novolak, o-cresol novolak, t-butylphenol novolak, dicyclopentadiene cresol, terpene diphenol, terpene dicatechol, 1,1,3-tris (3-tert-butyl-4- Hydroxy-6-methylphenyl) butane, butylidenebis (3-tert-butyl-4-hydroxy-6-methylphenyl), 2,2-bis (4-hydroxyphenyl) -1,1,1,3,3,3 -Hexafluoropropane and the like.
  • phenol novolac is preferable because the electrical properties and mechanical strength of the resulting epoxy resin are suitable for laminates.
  • ⁇ A flame retardant such as a phosphorus flame retardant can be blended in the epoxy resin composition of the present invention.
  • the blending amount of the flame retardant is preferably 5 to 100 parts by mass with respect to 100 parts by mass in total of the epoxy resin and the curing agent.
  • R 1 , R 2 and R 3 in the above formula each independently represent a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, a cycloalkyl group or a halogen atom, and Z 1 and Z 2 are A direct bond or an alkylene group or alkylidene group having 1 to 4 carbon atoms; ring C represents an arylene group, cycloalkylene group or arylene-alkylene (alkylidene) -arylene group having 6 to 18 carbon atoms .
  • the epoxy resin composition of the present invention is excellent in physical properties (high glass transition temperature, low linear expansion coefficient, tensile strength, elongation, flexibility, etc.) of the cured product without using a filler, Furthermore, it is preferable to use a filler (filler).
  • a filler filler
  • fiber fillers such as glass fibers, aluminum borate whiskers, boron nitride whiskers, potassium titanate whiskers, and titanium oxide whiskers, and spherical fillers such as silica, fused silica, and alumina are used. Is preferred.
  • silica alumina, aluminum borate, aluminum nitride, boron nitride, potassium titanate, titanium oxide, etc.
  • a fibrous filler When using a fibrous filler, it is preferable to appropriately select the length in the major axis direction and the aspect ratio according to the application.
  • a spherical filler those having a true spherical shape and a small particle diameter are preferred, and those having an average particle diameter in the range of 0.01 to 20 ⁇ m are particularly preferred.
  • plasticizers such as natural waxes, synthetic waxes and metal salts of long chain aliphatic acids; release agents such as acid amides, esters and paraffins; stress relieving agents such as nitrile rubber and butadiene rubber; trioxide Inorganic flame retardants such as antimony, antimony pentoxide, tin oxide, tin hydroxide, molybdenum oxide, zinc borate, barium metaborate, red phosphorus, aluminum hydroxide, magnesium hydroxide, calcium aluminate; tetrabromobisphenol A, anhydrous tetrabromo Brominated flame retardants such as phthalic acid, hexabromobenzene, brominated phenol novolak, etc .; phosphorus flame retardants other than the aforementioned phosphorus flame retardants; silane coupling agents, titanate coupling agents, aluminum coupling agents, etc.
  • Coupling agents coloring agents such as dyes and pigments; oxidation stabilizers, light stabilizers, moisture resistance improvers Thixotropic agents, diluents, antifoaming agents, other various resins, tackifiers, antistatic agents, lubricants, UV absorbers, alcohols, ethers, acetals, ketones, esters, alcohols Esters, ketone alcohols, ether alcohols, ketone ethers, ketone esters and ester ethers, organic solvents such as aromatic solvents, and the like can also be blended.
  • the epoxy resin composition of the present invention is suitable for use as an electrical / electronic material insulating resin, such as a multilayer printed wiring board, a semiconductor interposer, a semiconductor passivation film, or for applications such as heat resistant composite materials for aerospace. .
  • PA-2 Weight average molecular weight: 5970, Viscosity: 200 mPas (25 ° C., 30% by mass NMP solution)
  • PA-3 Weight average molecular weight: 13540 Viscosity: 525 mPas (25 ° C., 30% by mass NMP solution)
  • PA-4 Weight average molecular weight: 50370, Viscosity: 2500 mPas (25 ° C, 30% by mass NMP solution)
  • Examples 1 to 4 The following epoxy resin compositions described in Table 1 were prepared using polyamide compounds PA-1 to PA-4. A compounding quantity is a mass ratio.
  • An epoxy resin composition containing polyamide was applied to a thickness of 40 ⁇ m on a PET sheet, and a thin film resin dried at 100 ° C. for 10 minutes was vacuum-heat laminated at 100 ° C. on a glass epoxy substrate. Further, after curing at 180 ° C. for 1 hour to clean the surface, plating was performed to obtain a test piece for adhesion strength measurement, and the following measurements were performed.
  • Comparative Examples 1-7 The epoxy resin composition described in Table 2 was prepared. A compounding quantity is a mass ratio.
  • HPA-1 to HPA-7 are the compounds shown below.
  • thermosetting epoxy resin composition having a high peel strength with respect to a surface having a small surface roughness can be obtained. It is suitable as a build-up type insulating resin material, and can be used for insulating materials for electrical and electronic materials such as multilayer printed wiring boards , semiconductor interposers, semiconductor passivation films, and heat resistant composite materials for aerospace, etc. It is.

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Epoxy Resins (AREA)
  • Polyamides (AREA)

Abstract

Cette invention concerne un composé polyamide qui est caractérisé en ce qu'il contient une structure partielle représentée par la formule générale (I) et/ou la formule générale (I') dans un motif à répétition. (Dans les formules, X représente un atome d'hydrogène ou un groupe hydroxyle). Cette invention concerne également une composition de résine époxy qui utilise ledit composé à titre d'agent de durcissage. Le composé polyamide selon l'invention permet d'obtenir une résine époxy ayant une résistance au pelage élevée par rapport une surface à basse rugosité superficielle, sans augmenter la quantité de charge incorporée.
PCT/JP2010/006652 2009-11-13 2010-11-12 Composé polyamide et composition de résine époxy le contenant Ceased WO2011058756A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
KR1020127010350A KR101740081B1 (ko) 2009-11-13 2010-11-12 폴리아미드 화합물 및 그것을 함유하여 이루어지는 에폭시 수지 조성물
CN201080047345.2A CN102575004B (zh) 2009-11-13 2010-11-12 聚酰胺化合物及含有它而成的环氧树脂组合物

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2009-259933 2009-11-13
JP2009259933A JP5683093B2 (ja) 2009-11-13 2009-11-13 ポリアミド化合物及びそれを含有してなるエポキシ樹脂組成物

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WO2011058756A1 true WO2011058756A1 (fr) 2011-05-19

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PCT/JP2010/006652 Ceased WO2011058756A1 (fr) 2009-11-13 2010-11-12 Composé polyamide et composition de résine époxy le contenant

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JP (1) JP5683093B2 (fr)
KR (1) KR101740081B1 (fr)
CN (1) CN102575004B (fr)
TW (1) TWI496815B (fr)
WO (1) WO2011058756A1 (fr)

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JP2015021086A (ja) * 2013-07-22 2015-02-02 住友ベークライト株式会社 樹脂組成物、樹脂シート、プリプレグ、積層板、プリント配線板、及び半導体装置

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JP2013079326A (ja) * 2011-10-04 2013-05-02 Adeka Corp 樹脂組成物、該組成物を含有するビルドアップ用絶縁体、及び該組成物を用いたプリプレグ
JP6067922B2 (ja) * 2014-02-20 2017-01-25 アクロン ポリマー システムズ，インク． ディスプレイ用素子、光学用素子、照明用素子又はセンサ素子の製造のための芳香族ポリアミド溶液
CN105491839A (zh) * 2014-10-02 2016-04-13 亚克朗聚合物系统公司 盖构件和电子器件
JP2016098260A (ja) * 2014-11-18 2016-05-30 住友ベークライト株式会社 ポリアミド溶液
CN113248689B (zh) * 2021-06-23 2022-07-12 万华化学集团股份有限公司 一种多官能度酰胺混合物及其制备方法、一种预浸料
WO2025126940A1 (fr) * 2023-12-14 2025-06-19 東レ株式会社 Polymère, polyamide aromatique, corps moulé, film, capteur de vibrations, haut-parleur, et système de surveillance de l'état des structures

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JP2015021086A (ja) * 2013-07-22 2015-02-02 住友ベークライト株式会社 樹脂組成物、樹脂シート、プリプレグ、積層板、プリント配線板、及び半導体装置

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CN102575004A (zh) 2012-07-11
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