JPH0534368B2 - - Google Patents
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- Publication number
- JPH0534368B2 JPH0534368B2 JP62112723A JP11272387A JPH0534368B2 JP H0534368 B2 JPH0534368 B2 JP H0534368B2 JP 62112723 A JP62112723 A JP 62112723A JP 11272387 A JP11272387 A JP 11272387A JP H0534368 B2 JPH0534368 B2 JP H0534368B2
- Authority
- JP
- Japan
- Prior art keywords
- compound
- formula
- group
- hydrogen atom
- methyl 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.)
- Expired - Lifetime
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- 150000001875 compounds Chemical class 0.000 claims description 25
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- 229920001187 thermosetting polymer Polymers 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- -1 glycidyloxy group Chemical group 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 3
- 125000003700 epoxy group Chemical group 0.000 claims description 3
- 239000011342 resin composition Substances 0.000 claims description 3
- 239000003822 epoxy resin Substances 0.000 description 6
- 229920000647 polyepoxide Polymers 0.000 description 6
- 238000005452 bending Methods 0.000 description 5
- 238000005266 casting Methods 0.000 description 5
- 229920005989 resin Polymers 0.000 description 5
- 239000011347 resin Substances 0.000 description 5
- NXXYKOUNUYWIHA-UHFFFAOYSA-N 2,6-Dimethylphenol Chemical compound CC1=CC=CC(C)=C1O NXXYKOUNUYWIHA-UHFFFAOYSA-N 0.000 description 4
- 239000007870 radical polymerization initiator Substances 0.000 description 4
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- FBHPRUXJQNWTEW-UHFFFAOYSA-N 1-benzyl-2-methylimidazole Chemical compound CC1=NC=CN1CC1=CC=CC=C1 FBHPRUXJQNWTEW-UHFFFAOYSA-N 0.000 description 2
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 239000002131 composite material Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000012778 molding material Substances 0.000 description 2
- 229920001568 phenolic resin Polymers 0.000 description 2
- 239000005011 phenolic resin Substances 0.000 description 2
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- PLMIYFSPVVMPMX-UHFFFAOYSA-N 2-[(4-hydroxy-3,5-dimethylphenyl)methyl]prop-2-enamide Chemical compound CC1=CC(CC(=C)C(N)=O)=CC(C)=C1O PLMIYFSPVVMPMX-UHFFFAOYSA-N 0.000 description 1
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 1
- FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 description 1
- YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 description 1
- 229920003319 Araldite® Polymers 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- 229920000049 Carbon (fiber) Polymers 0.000 description 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
- OWYWGLHRNBIFJP-UHFFFAOYSA-N Ipazine Chemical compound CCN(CC)C1=NC(Cl)=NC(NC(C)C)=N1 OWYWGLHRNBIFJP-UHFFFAOYSA-N 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 239000004760 aramid Substances 0.000 description 1
- 229920006231 aramid fiber Polymers 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 1
- 239000004917 carbon fiber Substances 0.000 description 1
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000011256 inorganic filler Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- OHBCEHHJPNBVME-UHFFFAOYSA-N n-[[3,5-dimethyl-4-(oxiran-2-ylmethoxy)phenyl]methyl]prop-2-enamide Chemical compound CC1=CC(CNC(=O)C=C)=CC(C)=C1OCC1OC1 OHBCEHHJPNBVME-UHFFFAOYSA-N 0.000 description 1
- 239000012766 organic filler Substances 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 150000003003 phosphines Chemical class 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 229920006305 unsaturated polyester Polymers 0.000 description 1
- 229920006337 unsaturated polyester resin Polymers 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
- C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
- C08F20/52—Amides or imides
- C08F20/54—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide
- C08F20/58—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide containing oxygen in addition to the carbonamido oxygen, e.g. N-methylolacrylamide, N-acryloylmorpholine
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Epoxy Resins (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Description
「産業上の利用分野」
本発明は、耐熱性及び機械的強度に優れた熱硬
化性樹脂組成物に関するものである。
「従来技術と問題点」
従来、熱硬化性樹脂としては、フエノール樹
脂、エポキシ樹脂、不飽和ポリエステル樹脂等が
知られており、接着、塗料、成型材料、複合材料
の分野で広く使用されている。これらの熱硬化性
樹脂は一般に耐熱性の高いものは強度が低く、逆
に強度の高いものは耐熱性が低いという傾向があ
り、高い耐熱性と高い強度を両立させることは困
難であつた。一方、これらの熱硬化性樹脂を成型
材料、複合材料として用いる場合、耐熱性あるい
は強度が不足するため使用用途が限定されるとい
う問題があつた。
「問題点を解決するための手段」
本発明者らは、かかる問題点を解決すべく鋭意
検討した結果、特定の化合物を組み合わせた樹脂
組成物がこれらの問題点を解決し得ることを見出
し、本発明に到達した。
即ち、本発明は下記一般式（）
（式中、Ar1はグリシジルオキシ基を少なくと
も１個有する炭素数６〜20の芳香族炭化水素を、
Ｒは水素原子またはメチル基を表し、ｎは１〜４
の整数である）で表されるグリシジル化合物(A)
と、下記一般式（）
（式中、Ar2は水酸基を少なくとも１つ有する
炭素数６〜20の芳香族炭化水素基を、Ｒは水素原
子またはメチル基を表し、ｎは１〜４の整数であ
る）で表される化合物(B)を必須成分として含有
し、前記化合物(A)のエポキシ基と前記化合物(B)の
水酸基とのモル比が80：20〜20：80の範囲である
ことを特徴とする熱硬化性樹脂組成物を内容とす
るものである。下記一般式（）
（式中、Ar1はグリシジルオキシ基を少なくと
も１個有する炭素数６〜20の芳香族炭化水素を、
Ｒは水素原子またはメチル基を表し、ｎは１〜４
の整数である）で表される。かかる化合物(A)の製
造方法は、例えば特開昭60−130580に開示されて
いる。例えば２，６−キシレノールとＮ−メチロ
ール（メタ）アクリルアミドを縮合させたのち、
エピハロヒドリンでグリシジル化することによ
り、下記構造式（）
（式中、Ｒは水素原子またはメチル基である）
で表されるグリシジル化合物きを得ることができ
る。
本発明に用いることのできる化合物(B)は、下記
一般式（）
（式中、Ar2は水酸基を少なくとも１つ有する
炭素数６〜20の芳香族炭化水素基を、Ｒは水素原
子またはメチル基を表し、ｎは１〜４の整数であ
る）で表される化合物が本発明の目的に特に好適
である。かかる化合物(B)は例えばNeth.Pat.
Appln.No.6604304に開示されている方法により製
造することができる。例えば、２，６−キシレノ
ールとＮ−メチロール（メタ）アクリルアミドを
縮合させることにより下記構造式（）
（式中、Ｒは水素原子またはメチル基である）
で表される化合物を得ることができる。
本発明に用いる化合物(A)と化合物(B)の使用量
は、化合物(A)のエポキシ基と化合物(B)水酸基との
モル比が80：20〜20：80、更に好ましくは、60：
40〜40：60の範囲となるように調節されるべきで
ある。
通常、これらの化合物の混合物は加熱すること
により硬化するが、硬化を促進させるため、適当
な触媒を使用することが望ましい。使用できる触
媒としては、エポキシ樹脂の硬化に通常使用され
ている硬化促進剤及びラジカル重合開始剤が好適
であり、これらを併用して用いることが望まし
い。
エポキシ樹脂の硬化に使用されている硬化促進
剤としては、第３級アミン、第４級アンモニウム
塩、ホスフイン類、イミダゾール類、ウレア誘導
体等があるが、これらはいずれも本発明の組成物
の硬化促進剤として有効である。
ラジカル重合開始剤としては、一般にラジカル
重合の開始剤として知られているものが任意に使
用できるが、その中でも有機過酸化物が特に適し
ている。例示すれば、ｔ−ブチルハイドロパーオ
キサイド、キユメンハイドロパーオキサイド、ジ
クミルパーオキサイド、ｔ−ブチルパーベンゾエ
ート、ベンゾイルパーオキサイド等が挙げられ
る。
これら硬化促進剤及びラジカル重合開始剤の使
用量は、所望の硬化速度が得られるように設定す
べきであるが、通常ではそれぞれ化合物(A)と化合
物(B)の合計に対して0.01重量％〜10重量％、より
好ましくは0.1重量％〜３重量％の範囲で使用す
る。本発明の組成物には必要に応じて他の熱硬化
性樹脂例えば不飽和ポリエステル、エポキシ樹
脂、フエノール樹脂等を添加してもよい。またス
チレン、メチルメタクリレート、ブチルアクリレ
ート等の不飽和結合を有するモノマーを添加して
もよい。本発明の組成物は、また必要に応じて各
種の無機及び有機フイラーを添加してもよい。
「作用・硬化」
本発明の組成物からなる硬化物は高い耐熱性と
高い強度を兼ね備えているために各種の用途で使
用できる。例えば、炭素繊維、アラミド繊維、ガ
ラス繊維等のマトリツクス樹脂、電気用耐熱積層
板、耐熱構造用接着剤、高性能SMC等の用途で
使用できる。
「実施例」
以下、本発明を具体的に実施例により説明する
が、本発明はこれら実施例のみに限定されるもの
ではない。尚、以下において「部」は「重量部」
を表す。
実施例 １
Ｎ−（４−グリシジルオキシ−３，５−ジメチ
ルフエニルメチル）アクリルアミド（前記構造式
（）でＲが水素原子であるもの、以下これを化
合物Ａ−１とする）56部及びＮ−（４−ヒドロキ
シ−３，５−ジメチルフエニルメチル）アクリル
アミド（前記構造式（）でＲが水素原子である
もの、以下これを化合物(B)−１とする）44部を加
熱し混合したものに、１−ベンジル−２−メチル
イミダゾール1.0部、ジクミルパーオキサイド1.0
部を混合し、ガラス板の間に流し込み、120℃で
２時間、その後160℃で２時間、更にその後200℃
で２時間加熱し硬化させ注型板を作成した。得ら
れた注型板について曲げ強度、引張り強度、加熱
変形温度、Tgの測定を行つた結果を表１に示す。
実施例 ２
化合物Ａ−１を65.5部及び化合物Ｂ−１を34.5
部とした他は実施例１と同様の方法により注型板
の作成を行つた。得られた注型板について曲げ強
度、引張り強度、加熱変形温度、Tgの測定を行
つた結果を表１に示す。
実施例 ３
１−ベンジル−２−メチルイミダゾールの代わ
りに、トリフエニルホスフイン1.0部、ジクミル
パーオキサイドの代わりにｔ−ブチルハイドロパ
ーオキサイド1.0部を用いた他は実施例１と同様
の方法で注型板を作成した。得られた注型板につ
いて曲げ強度、引張り強度、加熱変形温度、Tg
の測定を行つた結果を表１に示す。
比較例 １
エピビス型エポキシ樹脂（商品名エピコート
828、油化シエル(株)製）100部、無水メチルナジツ
ク酸79.6部、Ｎ，Ｎ−ジメチルベンジルアミン
0.7部を混合しガラス板の間に流し込み、140℃で
１時間、その後150℃で15時間加熱し硬化させ注
型板を作成した。得られた注型板について曲げ強
度、引張り強度、加熱変形温度、Tgの測定を行
つた結果を表１に示す。
比較例 ２
４，4′−ジアミノジフエニルメタンとエピクロ
ルヒドリンから得られる多官能エポキシ樹脂（商
品名アラルダイトMY720、チバガイギー社製）
100部、無水メチルナジツク酸126部を混合しガラ
ス板の間に流し込み、100℃で２時間、その後150
℃で２時間、更にその後200℃で２時間加熱し硬
化させ注型板を作成した。得られた注型板につい
て曲げ強度、引張り強度、加熱変形温度、Tgの
測定を行つた結果を表１に示す。
"Industrial Application Field" The present invention relates to a thermosetting resin composition having excellent heat resistance and mechanical strength. "Prior Art and Problems" Conventionally, known thermosetting resins include phenolic resin, epoxy resin, and unsaturated polyester resin, which are widely used in the fields of adhesives, paints, molding materials, and composite materials. . These thermosetting resins generally have a tendency that those with high heat resistance have low strength, and conversely, those with high strength tend to have low heat resistance, and it has been difficult to achieve both high heat resistance and high strength. On the other hand, when these thermosetting resins are used as molding materials or composite materials, there is a problem that their uses are limited due to insufficient heat resistance or strength. "Means for Solving the Problems" As a result of intensive study to solve these problems, the present inventors discovered that a resin composition combining specific compounds could solve these problems, We have arrived at the present invention. That is, the present invention is based on the following general formula () (In the formula, Ar 1 is an aromatic hydrocarbon having 6 to 20 carbon atoms having at least one glycidyloxy group,
R represents a hydrogen atom or a methyl group, and n is 1 to 4
glycidyl compound (A), which is an integer of
and the following general formula () (In the formula, Ar 2 is an aromatic hydrocarbon group having at least one hydroxyl group and having 6 to 20 carbon atoms, R is a hydrogen atom or a methyl group, and n is an integer of 1 to 4.) A thermosetting product containing a compound (B) as an essential component, wherein the molar ratio of the epoxy group of the compound (A) to the hydroxyl group of the compound (B) is in the range of 80:20 to 20:80. The content is a synthetic resin composition. General formula below () (In the formula, Ar 1 is an aromatic hydrocarbon having 6 to 20 carbon atoms having at least one glycidyloxy group,
R represents a hydrogen atom or a methyl group, and n is 1 to 4
is an integer). A method for producing such compound (A) is disclosed, for example, in JP-A-60-130580. For example, after condensing 2,6-xylenol and N-methylol (meth)acrylamide,
By glycidylation with epihalohydrin, the following structural formula () is obtained. (In the formula, R is a hydrogen atom or a methyl group)
A glycidyl compound represented by the formula can be obtained. Compound (B) that can be used in the present invention has the following general formula () (In the formula, Ar 2 is an aromatic hydrocarbon group having at least one hydroxyl group and having 6 to 20 carbon atoms, R is a hydrogen atom or a methyl group, and n is an integer of 1 to 4.) Compounds are particularly suitable for the purposes of the present invention. Such compounds (B) are described, for example, by Neth.Pat.
It can be manufactured by the method disclosed in Appln.No.6604304. For example, by condensing 2,6-xylenol and N-methylol (meth)acrylamide, the following structural formula () (In the formula, R is a hydrogen atom or a methyl group)
A compound represented by can be obtained. The amount of compound (A) and compound (B) used in the present invention is such that the molar ratio of the epoxy group of compound (A) to the hydroxyl group of compound (B) is 80:20 to 20:80, more preferably 60:
It should be adjusted to be in the range of 40-40:60. Usually, mixtures of these compounds are cured by heating, but it is desirable to use a suitable catalyst to accelerate the curing. As catalysts that can be used, curing accelerators and radical polymerization initiators that are commonly used for curing epoxy resins are suitable, and it is desirable to use these in combination. Curing accelerators used for curing epoxy resins include tertiary amines, quaternary ammonium salts, phosphines, imidazoles, and urea derivatives, all of which can be used to cure the composition of the present invention. Effective as a promoter. As the radical polymerization initiator, any one generally known as a radical polymerization initiator can be used, but among them, organic peroxides are particularly suitable. Examples include t-butyl hydroperoxide, cumene hydroperoxide, dicumyl peroxide, t-butyl perbenzoate, and benzoyl peroxide. The amounts of these curing accelerators and radical polymerization initiators should be set so as to obtain the desired curing speed, but usually each is 0.01% by weight based on the total of compound (A) and compound (B). It is used in a range of 10% by weight, more preferably 0.1% by weight to 3% by weight. Other thermosetting resins such as unsaturated polyesters, epoxy resins, phenolic resins, etc. may be added to the composition of the present invention, if necessary. Furthermore, monomers having unsaturated bonds such as styrene, methyl methacrylate, and butyl acrylate may be added. The composition of the present invention may also contain various inorganic and organic fillers, if necessary. "Action/Curing" The cured product made from the composition of the present invention has both high heat resistance and high strength, so it can be used for various purposes. For example, it can be used for matrix resins such as carbon fibers, aramid fibers, and glass fibers, heat-resistant laminates for electrical use, adhesives for heat-resistant structures, and high-performance SMC. "Examples" Hereinafter, the present invention will be specifically explained using Examples, but the present invention is not limited only to these Examples. In addition, "parts" in the following are "parts by weight"
represents. Example 1 56 parts of N-(4-glycidyloxy-3,5-dimethylphenylmethyl)acrylamide (structural formula () in which R is a hydrogen atom, hereinafter referred to as compound A-1) and N -44 parts of (4-hydroxy-3,5-dimethylphenylmethyl)acrylamide (structural formula () above, in which R is a hydrogen atom, hereinafter referred to as compound (B)-1) were heated and mixed. Ingredients: 1.0 part of 1-benzyl-2-methylimidazole, 1.0 part of dicumyl peroxide.
Pour between glass plates and heat at 120°C for 2 hours, then at 160°C for 2 hours, then at 200°C.
The mixture was heated and cured for 2 hours to create a casting plate. Table 1 shows the results of measuring the bending strength, tensile strength, heat deformation temperature, and Tg of the obtained cast plate. Example 2 65.5 parts of compound A-1 and 34.5 parts of compound B-1
A casting plate was prepared in the same manner as in Example 1, except that the mold plate was made into a mold. Table 1 shows the results of measuring the bending strength, tensile strength, heat deformation temperature, and Tg of the obtained cast plate. Example 3 The same method as in Example 1 was used except that 1.0 part of triphenylphosphine was used instead of 1-benzyl-2-methylimidazole and 1.0 part of t-butyl hydroperoxide was used instead of dicumyl peroxide. A casting board was created. The bending strength, tensile strength, heating deformation temperature, Tg of the obtained cast plate
The results of the measurements are shown in Table 1. Comparative example 1 Epibis type epoxy resin (trade name Epicoat)
828, manufactured by Yuka Ciel Co., Ltd.) 100 parts, 79.6 parts of methylnadzic anhydride, N,N-dimethylbenzylamine
0.7 part of the mixture was mixed and poured between glass plates, and heated at 140°C for 1 hour and then at 150°C for 15 hours to harden and create a casting plate. Table 1 shows the results of measuring the bending strength, tensile strength, heat deformation temperature, and Tg of the obtained cast plate. Comparative Example 2 Multifunctional epoxy resin obtained from 4,4'-diaminodiphenylmethane and epichlorohydrin (trade name: Araldite MY720, manufactured by Ciba Geigy)
Mix 100 parts of methylnadzic anhydride and 126 parts of methylnadzic acid anhydride, pour between glass plates, heat at 100℃ for 2 hours, and then heat at 150℃.
The mixture was cured by heating at 200°C for 2 hours and then at 200°C for 2 hours to prepare a casting plate. Table 1 shows the results of measuring the bending strength, tensile strength, heat deformation temperature, and Tg of the obtained cast plate.
【表】
である。
[Table]
Claims (1)
も１個有する炭素数６〜20の芳香族炭化水素を、
Ｒは水素原子またはメチル基を表し、ｎは１〜４
の整数である）で表されるグリシジル化合物(A)
と、下記一般式（） （式中、Ar2は水酸基を少なくとも１つ有する
炭素数６〜20の芳香族炭化水素基を、Ｒは水素原
子またはメチル基を表し、ｎは１〜４の整数であ
る）で表される化合物(B)を必須成分として含有
し、前記化合物(A)のエポキシ基と前記化合物(B)の
水酸基とのモル比が80：20〜20：80の範囲である
ことを特徴とする熱硬化性樹脂組成物。 ２ 化合物(A)が下記構造式（） （式中、Ｒは水素原子またはメチル基である）
で表される特許請求の範囲第１項記載の組成物。 ３ 化合物(B)が下記一般式（） （式中、Ｒは水素原子またはメチル基である）
で表される特許請求の範囲第１項記載の組成物。[Claims] 1. The following general formula () (In the formula, Ar 1 is an aromatic hydrocarbon having 6 to 20 carbon atoms having at least one glycidyloxy group,
R represents a hydrogen atom or a methyl group, and n is 1 to 4
glycidyl compound (A), which is an integer of
and the following general formula () (In the formula, Ar 2 is an aromatic hydrocarbon group having at least one hydroxyl group and having 6 to 20 carbon atoms, R is a hydrogen atom or a methyl group, and n is an integer of 1 to 4.) A thermosetting product containing a compound (B) as an essential component, wherein the molar ratio of the epoxy group of the compound (A) to the hydroxyl group of the compound (B) is in the range of 80:20 to 20:80. resin composition. 2 Compound (A) has the following structural formula () (In the formula, R is a hydrogen atom or a methyl group)
The composition according to claim 1, which is represented by: 3 Compound (B) has the following general formula () (In the formula, R is a hydrogen atom or a methyl group)
The composition according to claim 1, which is represented by:
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11272387A JPS63277209A (en) | 1987-05-08 | 1987-05-08 | Thermosetting resin composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11272387A JPS63277209A (en) | 1987-05-08 | 1987-05-08 | Thermosetting resin composition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS63277209A JPS63277209A (en) | 1988-11-15 |
| JPH0534368B2 true JPH0534368B2 (en) | 1993-05-21 |
Family
ID=14593918
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP11272387A Granted JPS63277209A (en) | 1987-05-08 | 1987-05-08 | Thermosetting resin composition |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS63277209A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE69130664D1 (en) * | 1990-04-28 | 1999-02-04 | Kanegafuchi Chemical Ind | MODIFIED OLEFIN POLYMER, METHOD FOR THE PRODUCTION AND RESIN COMPOSITION THAT CONTAINS THIS POLYMER |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS56136865A (en) * | 1980-03-28 | 1981-10-26 | Kanebo Ltd | Adhesive composition for hard living tissue |
-
1987
- 1987-05-08 JP JP11272387A patent/JPS63277209A/en active Granted
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS56136865A (en) * | 1980-03-28 | 1981-10-26 | Kanebo Ltd | Adhesive composition for hard living tissue |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS63277209A (en) | 1988-11-15 |
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