JPS63277209A - Thermosetting resin composition - Google Patents
Thermosetting resin compositionInfo
- Publication number
- JPS63277209A JPS63277209A JP11272387A JP11272387A JPS63277209A JP S63277209 A JPS63277209 A JP S63277209A JP 11272387 A JP11272387 A JP 11272387A JP 11272387 A JP11272387 A JP 11272387A JP S63277209 A JPS63277209 A JP S63277209A
- Authority
- JP
- Japan
- Prior art keywords
- compound
- group
- methyl group
- formula
- hydrogen atom
- 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.)
- Granted
Links
- 229920001187 thermosetting polymer Polymers 0.000 title claims description 8
- 239000011342 resin composition Substances 0.000 title claims description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 36
- 239000000203 mixture Substances 0.000 claims abstract description 16
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 10
- 125000003700 epoxy group Chemical group 0.000 claims abstract description 8
- -1 glycidyl compound Chemical class 0.000 claims abstract description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims 4
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims 2
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical group CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 claims 1
- 239000000853 adhesive Substances 0.000 abstract description 3
- 230000001070 adhesive effect Effects 0.000 abstract description 3
- 229940126062 Compound A Drugs 0.000 abstract 2
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 abstract 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical group C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 description 7
- 239000003822 epoxy resin Substances 0.000 description 6
- 229920000647 polyepoxide Polymers 0.000 description 6
- 229920005989 resin Polymers 0.000 description 6
- 239000011347 resin Substances 0.000 description 6
- 238000005452 bending Methods 0.000 description 5
- NXXYKOUNUYWIHA-UHFFFAOYSA-N 2,6-Dimethylphenol Chemical compound CC1=CC=CC(C)=C1O NXXYKOUNUYWIHA-UHFFFAOYSA-N 0.000 description 4
- 238000005266 casting Methods 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
- LTVUCOSIZFEASK-MPXCPUAZSA-N (3ar,4s,7r,7as)-3a-methyl-3a,4,7,7a-tetrahydro-4,7-methano-2-benzofuran-1,3-dione Chemical compound C([C@H]1C=C2)[C@H]2[C@H]2[C@]1(C)C(=O)OC2=O LTVUCOSIZFEASK-MPXCPUAZSA-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
- 125000002029 aromatic hydrocarbon group Chemical group 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
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 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
- FBHPRUXJQNWTEW-UHFFFAOYSA-N 1-benzyl-2-methylimidazole Chemical compound CC1=NC=CN1CC1=CC=CC=C1 FBHPRUXJQNWTEW-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
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-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
- 241000238557 Decapoda Species 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
- 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
- 230000000694 effects Effects 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 150000003944 halohydrins Chemical class 0.000 description 1
- 150000002460 imidazoles Chemical class 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
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- XLSZMDLNRCVEIJ-UHFFFAOYSA-N methylimidazole Natural products CC1=CNC=N1 XLSZMDLNRCVEIJ-UHFFFAOYSA-N 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- RMWQBWIPOMZVKK-UHFFFAOYSA-N n-[(4-hydroxy-3,5-dimethylphenyl)methyl]prop-2-enamide Chemical compound CC1=CC(CNC(=O)C=C)=CC(C)=C1O RMWQBWIPOMZVKK-UHFFFAOYSA-N 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
- 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
- 238000002411 thermogravimetry Methods 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)
Abstract
Description
【発明の詳細な説明】
「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。DETAILED DESCRIPTION OF THE INVENTION "Field of Industrial Application" The present invention relates to a thermosetting resin composition having excellent heat resistance and mechanical strength.
「従来技術と問題点」
従来、熱硬化性樹脂としては、フェノール樹脂、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
は困難であった。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った
。"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. . Generally, those thermosetting resins with high heat resistance tend to have low strength, and conversely, those with high strength tend to have low heat resistance, so 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.
「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
。"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.
即ち、本発明は少なくとも１個のエポキシ基と少なくと
も１個のナタリルアミドメチル基またはメタクリルアミ
ドメチル基を存する化合物（Ａ）と、少なくとも１個の
水酸基と少なくとも１個のアクリルアミドメチル基また
はメタクリルアミドメチル基を有する化合物（Ｂ）を必
須成分として含有す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。That is, the present invention provides a compound (A) having at least one epoxy group and at least one natalylamide methyl group or methacrylamide methyl group, and a compound (A) having at least one hydroxyl group and at least one acrylamide methyl group or methacrylamide methyl group. The thermosetting resin composition is characterized by containing a compound (B) having a methyl group as an essential component.
本発明に用いることのできる化合物（Ａ）は、少なくと
も１個のエポキシ基と少なくとも１個のアクリルアミド
メチル基またはメタクリルアミドメチル基を有する化合
物であれば特に限定されないが、下記一般式（Ｉ）
￥
（ＣＨｚ ＝ＣＣＮＨＣＨｚ＋ＴＡｒ’ （１）（
式中、Ａｒ’ 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
表される化合物（Ａ）が本発明の目的に特に好適である
。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０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、エビ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（ＩＩ）
（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。The compound (A) that can be used in the present invention is not particularly limited as long as it has at least one epoxy group and at least one acrylamide methyl group or methacrylamide methyl group, but may be represented by the following general formula (I) ¥ (CHz = CCNHCHz+TAr' (1) (
In the formula, Ar' is an aromatic hydrocarbon having 6 to 20 carbon atoms having at least one glycidyloxy group, R is a hydrogen atom or a methyl group, and n is an integer of 1 to 4. Compound (A) is particularly suitable for the purposes of the present invention. The method for producing such compound (A) is described, for example, in JP-A-60
For example, by condensing 2,6-xylenol and N-methylol (meth)acrylamide and glycidylating it with shrimp halohydrin, the following structural formula (II) (wherein R is a hydrogen atom) is obtained. or a methyl group) can be obtained.
本発明に用いることのできる化合物（Ｂ）は、少なくと
も１個の水酸基と少なくとも１個のアクリルアミドメチ
ル基またはメタクリルアミドメチル基を有する化合物で
あれば良く、特に限定されないが、下記一般式（Ｉ［ｌ
）
す
（ＣＨｔ −Ｃ−Ｃ−ＮＨ−ＣＨｚ−）−ｒＡｒ”
（Ｉ［Ｉ ）（式中、Ａｒ”は水酸基を少なくとも１つ
存する炭素数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、Ａｐｐｌ
ｎ、Ｎｏ、６，６０４，３０４に開示されている方法に
より製造することができる９例えは、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（ＩＶ）（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。The compound (B) that can be used in the present invention is not particularly limited as long as it has at least one hydroxyl group and at least one acrylamide methyl group or methacrylamide methyl group. l
) Su(CHt-C-C-NH-CHz-)-rAr”
(I[I) (wherein, Ar" represents an aromatic hydrocarbon group having at least one hydroxyl group and having 6 to 20 carbon atoms, R represents a hydrogen atom or a methyl group, and n is an integer of 1 to 4. )
Compounds represented by are particularly suitable for the purposes of the present invention. Such compounds (B) include, for example, Neth, Pat, Appl
For example, the following structural formula (IV) can be produced by condensing 2,6-xylenol and N-methylol (meth)acrylamide. A compound represented by the formula (wherein R is a hydrogen atom or a methyl group) can be obtained.
本発明に用いる化合物（Ａ）と化合物（Ｂ）の使用量は
、化合￥！ｙＪ（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。The amounts of compound (A) and compound (B) used in the present invention are compound ¥! The molar ratio of the epoxy group of yJ (A) to the hydroxyl group of compound (B) should be adjusted to be in the range of 80:20 to 20:80, more preferably 60:40 to 40:60.
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。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.
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、ホスフィン
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。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.
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、キュメンハイドロ
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。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. For example,
Examples include t-butyl hydroperoxide, cumene hydroperoxide, dicumyl peroxide, t-butyl perbenzoate, and benzoyl peroxide.
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％〜１゜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、フェ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−１・、
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ィラーを添加してもよい。The usage amounts of these curing accelerators and radical polymerization initiators are as follows:
The setting should be such that the desired curing speed is obtained;
Usually 0.01% to 1% by weight, more preferably 0.01% to 1% by weight, based on the total of compound (A) and compound (B).
．． It is used in a range of 1% 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 as necessary, and styrene, methyl methacrylate-1,
A monomer having an unsaturated bond such as butyl acrylate may be added. The composition of the present invention may also contain various inorganic and organic fillers, if necessary.
「作用・効果」
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０例え
ば、炭素繊維、アラミド繊維、ガラス繊維等のマトリッ
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。"Action/Effect" The cured product made of the composition of the present invention has both high heat resistance and high strength, so it can be used for various purposes.For example, matrix resins such as carbon fiber, aramid fiber, glass fiber, It can be used for applications such as heat-resistant laminates, heat-resistant structural adhesives, and high-performance SMC.
「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。"Examples" The present invention will be specifically explained below using Examples, but the present invention is not limited only to these Examples.
In the following, "parts" represent "parts by weight."
実施例Ｉ
Ｎ−（４−グリシジルオキシ−３，５−ジメチルフェニ
ルメチル）アクリルアミド（前記構造式（ｎ）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）５
６部及びＮ−（４−ヒドロキシ−３，５−ジメチルフェ
ニルメチル）アクリルアミド（前記構造式（ｒＶ）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の測定を行った結果を表１に示す。Example I N-(4-glycidyloxy-3,5-dimethylphenylmethyl)acrylamide (structural formula (n) above, where R is a hydrogen atom, hereinafter referred to as compound A-1)5
6 parts and N-(4-hydroxy-3,5-dimethylphenylmethyl)acrylamide (R in the above structural formula (rV)
1-benzyl-2-
Mix 1.0 part of methylimidazole and 1.0 part of dicumyl peroxide, pour it between glass plates, and heat at 120°C.
for 2 hours, then at 160°C for 2 hours, and then at 200°C.
The mixture was cured by heating at ℃ for 2 hours to prepare a casting plate. The bending strength, tensile strength, heating deformation temperature,
Table 1 shows the results of Tg measurements.
実施例２
化合物Ａ−１を６５．５部及び化合！ｌ１ｌｌＩＢ−１
を３４．５部とした他は実施例１と同様の方法により注
型板の作成を行った。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の測定を行った結果
を表１に示す。Example 2 65.5 parts of compound A-1 and compound! l1llIB-1
A casting plate was prepared in the same manner as in Example 1, except that the amount was changed to 34.5 parts. Table 1 shows the results of measuring the bending strength, tensile strength, heating deformation temperature, and Tg of the obtained cast plate.
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
リフェニルホスフィン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の測定を行った結果を表１に示す。Example 3 1.0 part of triphenylphosphine instead of 1-benzyl-2-methylimidazole, 1.0 part of t-butyl hydroperoxide instead of dicumyl peroxide
A casting plate was prepared in the same manner as in Example 1, except that a mold was used. Table 1 shows the results of measuring the bending strength, tensile strength, heating deformation temperature, and Tg of the obtained cast plate.
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
化シェル（株）製）１００部、無水メチルナジック酸７
９．６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の測定を行った結果を表１に示す。Comparative Example 1 100 parts of Epibis type epoxy resin (trade name Epicote 828, manufactured by Yuka Shell Co., Ltd.), 7 parts of methylnadic anhydride
9.6 parts of N,N-dimethylbenzylamine and 0.7 parts of N,N-dimethylbenzylamine were mixed, poured between glass plates, heated at 140°C for 1 hour, and then heated at 150°C for 15 hours to harden to prepare a casting plate. Table 1 shows the results of measuring the bending strength, tensile strength, heating deformation temperature, and Tg of the obtained cast plate.
比較例２
４，４′−ジアミノジフェ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
チルナジック酸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。Comparative Example 2 100 parts of a polyfunctional epoxy resin obtained from 4,4'-diaminodiphenylmethane and epichlorohydrin (trade name Araldite MY720, manufactured by Ciba Geigy) and 126 parts of methylnadic anhydride were mixed, poured between glass plates, and heated at 100°C for 2 hours. After that, the mixture was heated at 150° C. for 2 hours, and then at 200° C. for 2 hours to harden, and a cast plate was prepared.
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の測定を行った結果を表１に示す。Table 1 shows the results of measuring the bending strength, tensile strength, heating deformation temperature, and Tg of the obtained cast plate.
表 １
上記表１の結果から明らかな如く、本発明の樹脂である
。Table 1 As is clear from the results in Table 1 above, this is the resin of the present invention.
Claims (1)
クリルアミドメチル基またはメタクリルアミドメチル基
を有する化合物（Ａ）と、少なくとも１個の水酸基と少
なくとも１個のアクリルアミドメチル基またはメタクリ
ルアミドメチル基を有する化合物（Ｂ）を必須成分とし
て含有することを特徴とする熱硬化性樹脂組成物。 ２、化合物（Ａ）が下記一般式（ I ） ▲数式、化学式、表等があります▼（ I ） （式中、Ａｒ＾１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である特許請求の範囲第１
項記載の組成物。 ３、グリシジル化合物が下記構造式（II） ▲数式、化学式、表等があります▼（II） （式中、Ｒは水素原子またはメチル基である）で表され
る化合物である特許請求の範囲第２項記載の組成物。 ４、化合物（Ｂ）が下記一般式（III） ▲数式、化学式、表等があります▼（III） （式中、Ａｒ＾２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
化合物である特許請求の範囲第１項記載の組成物。 ５、化合物（Ｂ）が下記構造式（IV） ▲数式、化学式、表等があります▼（IV） （式中、Ｒは水素原子またはメチル基である）で表され
る化合物である特許請求の範囲第４項記載の組成物。 ６、化合物（Ａ）のエポキシ基と化合物（Ｂ）の水酸基
とのモル比が８０：２０〜２０：８０の範囲である特許
請求の範囲第１項乃至第５項の各項記載の組成物。[Claims] 1. A compound (A) having at least one epoxy group and at least one acrylamide methyl group or methacrylamide methyl group, and at least one hydroxyl group and at least one acrylamide methyl group or methacrylamide group; A thermosetting resin composition comprising a compound (B) having an amidomethyl group as an essential component. 2. Compound (A) has the following general formula (I) ▲There are mathematical formulas, chemical formulas, tables, etc.▼(I) (In the formula, Ar^1 represents at least one glycidyloxy group.
aromatic hydrocarbon having 6 to 20 carbon atoms, R represents a hydrogen atom or a methyl group, and n is an integer of 1 to 4)
Claim 1, which is a glycidyl compound represented by
Compositions as described in Section. 3. Claims No. 1 in which the glycidyl compound is a compound represented by the following structural formula (II) ▲There are mathematical formulas, chemical formulas, tables, etc.▼(II) (wherein R is a hydrogen atom or a methyl group) Composition according to item 2. 4. Compound (B) has the following general formula (III) ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (III) (In the formula, Ar^2 is an aromatic hydrocarbon having 6 to 20 carbon atoms and having at least one hydroxyl group. The composition according to claim 1, wherein R is a hydrogen atom or a methyl group, and n is an integer of 1 to 4. 5. A patent claim in which the compound (B) is a compound represented by the following structural formula (IV) ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (IV) (wherein R is a hydrogen atom or a methyl group) A composition according to scope item 4. 6. The composition according to each of claims 1 to 5, wherein the molar ratio of the epoxy group of compound (A) to the hydroxyl group of compound (B) is in the range of 80:20 to 20:80. .
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 true JPS63277209A (en) | 1988-11-15 |
| JPH0534368B2 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) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1991017192A1 (en) * | 1990-04-28 | 1991-11-14 | Kanegafuchi Kagaku Kogyo Kabushiki Kaisha | Modified polyolefin polymer, production thereof, and resin composition containing the same |
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 |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1991017192A1 (en) * | 1990-04-28 | 1991-11-14 | Kanegafuchi Kagaku Kogyo Kabushiki Kaisha | Modified polyolefin polymer, production thereof, and resin composition containing the same |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0534368B2 (en) | 1993-05-21 |
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