JPH01311112A - Novel heat-resistant resin - Google Patents
Novel heat-resistant resinInfo
- Publication number
- JPH01311112A JPH01311112A JP14054088A JP14054088A JPH01311112A JP H01311112 A JPH01311112 A JP H01311112A JP 14054088 A JP14054088 A JP 14054088A JP 14054088 A JP14054088 A JP 14054088A JP H01311112 A JPH01311112 A JP H01311112A
- Authority
- JP
- Japan
- Prior art keywords
- ene
- dicarboximide
- hept
- compound
- oxabicyclo
- 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.)
- Pending
Links
- 229920006015 heat resistant resin Polymers 0.000 title claims abstract description 7
- 239000000178 monomer Substances 0.000 claims abstract description 17
- 125000000391 vinyl group Chemical class [H]C([*])=C([H])[H] 0.000 claims abstract description 17
- 229920002554 vinyl polymer Chemical class 0.000 claims abstract description 17
- -1 oxabicyclo(2,2,1)hept-5-ene-2,3-dicarboximide compound Chemical class 0.000 claims abstract description 12
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 1
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 abstract description 8
- 150000001875 compounds Chemical class 0.000 abstract description 7
- 238000007334 copolymerization reaction Methods 0.000 abstract description 4
- 238000002156 mixing Methods 0.000 abstract description 3
- 229920005989 resin Polymers 0.000 abstract description 3
- 239000011347 resin Substances 0.000 abstract description 3
- 239000004342 Benzoyl peroxide Substances 0.000 abstract description 2
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 abstract description 2
- 235000019400 benzoyl peroxide Nutrition 0.000 abstract description 2
- 239000003999 initiator Substances 0.000 abstract description 2
- JFUOAGBSDGCVES-UHFFFAOYSA-N 3-but-2-enyl-4-methylpyrrolidine-2,5-dione Chemical compound CC=CCC1C(C)C(=O)NC1=O JFUOAGBSDGCVES-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 229920001577 copolymer Polymers 0.000 description 6
- 238000006116 polymerization reaction Methods 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- BQTPKSBXMONSJI-UHFFFAOYSA-N 1-cyclohexylpyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1CCCCC1 BQTPKSBXMONSJI-UHFFFAOYSA-N 0.000 description 3
- PUHQMJSQZPUXJP-UHFFFAOYSA-N 2-phenyl-3a,4,7,7a-tetrahydro-octahydro-1h-4,7-epoxyisoindole-1,3-dione Chemical compound O=C1C2C(C=C3)OC3C2C(=O)N1C1=CC=CC=C1 PUHQMJSQZPUXJP-UHFFFAOYSA-N 0.000 description 3
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 3
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- 229920001519 homopolymer Polymers 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000003505 polymerization initiator Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- KDGNCLDCOVTOCS-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy propan-2-yl carbonate Chemical compound CC(C)OC(=O)OOC(C)(C)C KDGNCLDCOVTOCS-UHFFFAOYSA-N 0.000 description 1
- MKRBAPNEJMFMHU-UHFFFAOYSA-N 1-benzylpyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1CC1=CC=CC=C1 MKRBAPNEJMFMHU-UHFFFAOYSA-N 0.000 description 1
- KTZVZZJJVJQZHV-UHFFFAOYSA-N 1-chloro-4-ethenylbenzene Chemical compound ClC1=CC=C(C=C)C=C1 KTZVZZJJVJQZHV-UHFFFAOYSA-N 0.000 description 1
- JZHGRUMIRATHIU-UHFFFAOYSA-N 1-ethenyl-3-methylbenzene Chemical compound CC1=CC=CC(C=C)=C1 JZHGRUMIRATHIU-UHFFFAOYSA-N 0.000 description 1
- HIDBROSJWZYGSZ-UHFFFAOYSA-N 1-phenylpyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1=CC=CC=C1 HIDBROSJWZYGSZ-UHFFFAOYSA-N 0.000 description 1
- OLQFXOWPTQTLDP-UHFFFAOYSA-N 2-(2-hydroxyethoxy)ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCO OLQFXOWPTQTLDP-UHFFFAOYSA-N 0.000 description 1
- HPAYEMRCHCWDMA-UHFFFAOYSA-N 2-benzyl-3a,4,7,7a-tetrahydro-octahydro-1h-4,7-epoxyisoindole-1,3-dione Chemical compound O=C1C2C(C=C3)OC3C2C(=O)N1CC1=CC=CC=C1 HPAYEMRCHCWDMA-UHFFFAOYSA-N 0.000 description 1
- LJWFVGRNDAJTKW-UHFFFAOYSA-N 2-butyl-3a,4,7,7a-tetrahydro-octahydro-1h-4,7-epoxyisoindole-1,3-dione Chemical compound C1=CC2OC1C1C2C(=O)N(CCCC)C1=O LJWFVGRNDAJTKW-UHFFFAOYSA-N 0.000 description 1
- ASXWXGRJXABJET-UHFFFAOYSA-N 2-cyclohexyl-3a,4,7,7a-tetrahydro-octahydro-1h-4,7-epoxyisoindole-1,3-dione Chemical compound O=C1C2C(C=C3)OC3C2C(=O)N1C1CCCCC1 ASXWXGRJXABJET-UHFFFAOYSA-N 0.000 description 1
- SVXGVAQSQSAJHE-UHFFFAOYSA-N 2-ethyl-3a,4,7,7a-tetrahydro-octahydro-1h-4,7-epoxyisoindole-1,3-dione Chemical compound C1=CC2OC1C1C2C(=O)N(CC)C1=O SVXGVAQSQSAJHE-UHFFFAOYSA-N 0.000 description 1
- RUPYJKKEPSEMME-UHFFFAOYSA-N 2-propan-2-yl-3a,4,7,7a-tetrahydro-octahydro-1h-4,7-epoxyisoindole-1,3-dione Chemical compound C1=CC2OC1C1C2C(=O)N(C(C)C)C1=O RUPYJKKEPSEMME-UHFFFAOYSA-N 0.000 description 1
- QJVMAKJALBUARH-UHFFFAOYSA-N 2-propyl-3a,4,7,7a-tetrahydro-octahydro-1h-4,7-epoxyisoindole-1,3-dione Chemical compound C1=CC2OC1C1C2C(=O)N(CCC)C1=O QJVMAKJALBUARH-UHFFFAOYSA-N 0.000 description 1
- BSEKZMOBPPOFFB-UHFFFAOYSA-N 3a,4,7,7a-tetrahydro-octahydro-1h-4,7-epoxyisoindole-1,3-dione Chemical class O1C2C3C(=O)NC(=O)C3C1C=C2 BSEKZMOBPPOFFB-UHFFFAOYSA-N 0.000 description 1
- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 238000005698 Diels-Alder reaction Methods 0.000 description 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 1
- YIVJZNGAASQVEM-UHFFFAOYSA-N Lauroyl peroxide Chemical compound CCCCCCCCCCCC(=O)OOC(=O)CCCCCCCCCCC YIVJZNGAASQVEM-UHFFFAOYSA-N 0.000 description 1
- WLLGXSLBOPFWQV-UHFFFAOYSA-N MGK 264 Chemical compound C1=CC2CC1C1C2C(=O)N(CC(CC)CCCC)C1=O WLLGXSLBOPFWQV-UHFFFAOYSA-N 0.000 description 1
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 description 1
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- AOJOEFVRHOZDFN-UHFFFAOYSA-N benzyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC1=CC=CC=C1 AOJOEFVRHOZDFN-UHFFFAOYSA-N 0.000 description 1
- GCTPMLUUWLLESL-UHFFFAOYSA-N benzyl prop-2-enoate Chemical compound C=CC(=O)OCC1=CC=CC=C1 GCTPMLUUWLLESL-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000012662 bulk polymerization Methods 0.000 description 1
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- XJELOQYISYPGDX-UHFFFAOYSA-N ethenyl 2-chloroacetate Chemical compound ClCC(=O)OC=C XJELOQYISYPGDX-UHFFFAOYSA-N 0.000 description 1
- UIWXSTHGICQLQT-UHFFFAOYSA-N ethenyl propanoate Chemical compound CCC(=O)OC=C UIWXSTHGICQLQT-UHFFFAOYSA-N 0.000 description 1
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 description 1
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 1
- QQYNRBAAQFZCLF-UHFFFAOYSA-N furan-maleic anhydride adduct Chemical compound O1C2C3C(=O)OC(=O)C3C1C=C2 QQYNRBAAQFZCLF-UHFFFAOYSA-N 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 125000005395 methacrylic acid group Chemical group 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- WFKDPJRCBCBQNT-UHFFFAOYSA-N n,2-dimethylprop-2-enamide Chemical compound CNC(=O)C(C)=C WFKDPJRCBCBQNT-UHFFFAOYSA-N 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- QIWKUEJZZCOPFV-UHFFFAOYSA-N phenyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1=CC=CC=C1 QIWKUEJZZCOPFV-UHFFFAOYSA-N 0.000 description 1
- WRAQQYDMVSCOTE-UHFFFAOYSA-N phenyl prop-2-enoate Chemical compound C=CC(=O)OC1=CC=CC=C1 WRAQQYDMVSCOTE-UHFFFAOYSA-N 0.000 description 1
- BOQSSGDQNWEFSX-UHFFFAOYSA-N propan-2-yl 2-methylprop-2-enoate Chemical compound CC(C)OC(=O)C(C)=C BOQSSGDQNWEFSX-UHFFFAOYSA-N 0.000 description 1
- LYBIZMNPXTXVMV-UHFFFAOYSA-N propan-2-yl prop-2-enoate Chemical compound CC(C)OC(=O)C=C LYBIZMNPXTXVMV-UHFFFAOYSA-N 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000003507 refrigerant Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000010557 suspension polymerization reaction Methods 0.000 description 1
Landscapes
- 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、Ｎ−置換オキサビシクロ［２，２゜１コヘプ
ト−５−エン−２，３−ジカルボキシイミド化合物及び
ビニル系単量体からなる新規な耐熱性樹脂に関する。DETAILED DESCRIPTION OF THE INVENTION <Industrial Application Field> The present invention relates to the production of N-substituted oxabicyclo[2,2゜1-cohept-5-ene-2,3-dicarboximide compounds and vinyl monomers. The present invention relates to a new heat-resistant resin.
〈従来の技術〉
Ｎ−置換オキサビシクロ［２，２，１］ヘプト−５−エ
ン−２，３−ジカルボキシイミドの重合体に関する研究
は、たとえばＮ、Ｇ、 Ｇａｙｌｏｒｄら；Ｊ、Ｐｏｌ
ｙｍ、Ｓｃｉ、、Ｐｏｌｙｍ、Ｃｈｅａ＋、Ｅｄ、、１
６．１５２７（Ｉ９７８）に示されるようにオキサビシ
クロ［２，２，１］ヘプト−５−エン−２，３−ジカル
ボン酸無水物のホモ重合体に関する研究は報告されてい
るが、該酸無水物とビニル系単量体との共重合体に関す
る研究は全く行なわれていない。<Prior Art> Studies on polymers of N-substituted oxabicyclo[2,2,1]hept-5-ene-2,3-dicarboximides are described, for example, by N. G. Gaylord et al.; J. Pol.
ym,Sci,,Polym,Chea+,Ed,,1
6.1527 (I978), studies on homopolymers of oxabicyclo[2,2,1]hept-5-ene-2,3-dicarboxylic acid anhydride have been reported; No research has been conducted on copolymers of vinyl monomers and vinyl monomers.
〈発明が解決しようとする課題〉
本発明の目的は、Ｎ−１換オキサビシクロ［２゜２．１
］ヘプト−５−エン−２，３−ジカルボキシイミド化合
物とビニル系単量体とを共重合させてなる新規な耐熱性
樹脂を提供することにある。<Problems to be Solved by the Invention> The purpose of the present invention is to solve the problem by solving N-1-substituted oxabicyclo
] An object of the present invention is to provide a novel heat-resistant resin obtained by copolymerizing a hept-5-ene-2,3-dicarboximide compound and a vinyl monomer.
く課題を解決するための手段〉
本発明者らはＮ−２２換オキサビシクロ［２，２゜１コ
ヘプト−５−エン−２，３−ジカルボキシイミドの新規
な共重合体について鋭意検討した結果本発明を完成した
。Means for Solving the Problems The present inventors have conducted extensive studies on a novel copolymer of N-22-substituted oxabicyclo[2,2゜1-cohept-5-ene-2,3-dicarboximide]. The invention has been completed.
すなわち、本発明によれば、−形成（Ｊ）○
■
（式中、Ｒは水素原子、炭素数１〜１８の直鎖アルキル
基、分岐アルキル基、シクロアルキル基、アリール基ま
たはアラルキル基を表わす、）で示されるＮ−置換オキ
サビシクロ［２，２，１］へブドー５−エン−２，３−
ジカルボキシイミド化合物およびこれと共重合可能なビ
ニル系単量体を共重合してなる耐熱性樹脂が提供される
。That is, according to the present invention, - formation (J) , ) N-substituted oxabicyclo[2,2,1]hebdo-5-ene-2,3-
Provided is a heat-resistant resin formed by copolymerizing a dicarboximide compound and a vinyl monomer copolymerizable with the dicarboximide compound.
以下、本発明につき更に詳細に説明する。The present invention will be explained in more detail below.
本発明では一般式（Ｉ）
にて示されるＮ−置換オキサビシクロ［２，２゜１コヘ
プト−５−エン−２，３−ジカルボキシイミド化合物を
用いる。式中、Ｒは水素原子、炭素数１〜１８の直鎖ア
ルキル基１分岐アルキル基、シクロアルキル基、アリー
ル基またはアラルキル基を表わす。炭素数が１９以上と
なると製造が困難となるので使用できない。本発明にて
用いられる化合物（Ｉ）としては、オキサビシクロ［２
゜２．１コヘブト−５−エン−２，３−ジカルボキシイ
ミド、Ｎ−メチルオキサビシクロ［２，２゜１］ヘプト
−５−エン−２，３−ジカルボキシイミド、Ｎ−エチル
オキサビシクロ［２，２，１］ヘプト−５−エン−２，
３−ジカルボキシイミド。In the present invention, an N-substituted oxabicyclo[2,2°1-cohept-5-ene-2,3-dicarboximide compound represented by the general formula (I) is used. In the formula, R represents a hydrogen atom, a straight chain alkyl group having 1 to 18 carbon atoms, a monobranched alkyl group, a cycloalkyl group, an aryl group, or an aralkyl group. If the number of carbon atoms is 19 or more, it becomes difficult to manufacture and cannot be used. Compound (I) used in the present invention includes oxabicyclo[2
゜2.1 Kohebut-5-ene-2,3-dicarboximide, N-methyloxabicyclo[2,2゜1]hept-5-ene-2,3-dicarboximide, N-ethyloxabicyclo[ 2,2,1]hept-5-ene-2,
3-dicarboximide.
Ｎ−ｎ−プロピルオキサビシクロ［２，２，１］ヘプト
−５−エン−２，３−ジカルボキシイミド、Ｎ−イソプ
ロピルオキサビシクロ［２，２，１］ヘプト−５−エン
−２，３−ジカルボキシイミド、Ｎ−ｎ−ブチルオキサ
ビシクロ［２，２，１］ヘプト−５−エン−２，３−ジ
カルボキシイミド、Ｎ−イソブチルオキサビシクロ［２
，２，１］ヘプト−５−エン−２，３−ジカルボキシイ
ミド、Ｎ−（３−メチルプロピル）オキサビシクロ［２
゜２．１］ヘプト−５−エン−２，３−ジカルボキシイ
ミド、Ｎ−ｎ−ヘキシルオキサビシクロ［２゜２．１］
ヘプト−５−エン−２，３−ジカルボキシイミド、Ｎ−
ｎ−オクチルオキサビシクロ［２゜２．１］ヘプト−５
−エン−２，３−ジカルボキシイミド、Ｎ−ｎ−ドデシ
ルオキサビシクロ［２゜２．１］ヘプト−５−エン−２
，３−ジカルボキシイミド、Ｎ−ｎ−オクタデシルオキ
サビシクロ［２，２，１］ヘプト−５−エン−２，３−
ジカルボキシイミド、Ｎ−シクロヘキシルオキサビシク
ロ［２，２，１］ヘプト−５−エン−２，３−ジカルボ
キシイミド、Ｎ−フェニルオキサビシクロ［２，２，１
］ヘプト−５−エン−２，３−ジカルボキシイミド、Ｎ
−ベンジルオキサビシクロ［２，２，１］ヘプト−５−
エン−２，３−ジカルボキシイミドなどが挙げられる。N-n-propyloxabicyclo[2,2,1]hept-5-ene-2,3-dicarboximide, N-isopropyloxabicyclo[2,2,1]hept-5-ene-2,3- Dicarboximide, N-n-butyloxabicyclo[2,2,1]hept-5-ene-2,3-dicarboximide, N-isobutyloxabicyclo[2
,2,1]hept-5-ene-2,3-dicarboximide, N-(3-methylpropyl)oxabicyclo[2
゜2.1] hept-5-ene-2,3-dicarboximide, N-n-hexyloxabicyclo[2゜2.1]
hept-5-ene-2,3-dicarboximide, N-
n-octyloxabicyclo[2゜2.1]hept-5
-ene-2,3-dicarboximide, N-n-dodecyloxabicyclo[2°2.1]hept-5-ene-2
, 3-dicarboximide, N-n-octadecyloxabicyclo[2,2,1]hept-5-ene-2,3-
Dicarboximide, N-cyclohexyloxabicyclo[2,2,1]hept-5-ene-2,3-dicarboximide, N-phenyloxabicyclo[2,2,1
]Hept-5-ene-2,3-dicarboximide, N
-benzyloxabicyclo[2,2,1]hept-5-
Examples include ene-2,3-dicarboximide.
これらの化合物（Ｉ）は通常フランおよびＮ−ｔ？１Ｆ
換マレイミドのディールスアルダー反応により合成する
ことができる。These compounds (I) are usually furan and Nt? 1F
It can be synthesized by Diels-Alder reaction of converted maleimide.
本発明では化合物（Ｉ）と共重合可能なビニル系単量体
を用いる。かようなビニル系単量体としては、アクリル
酸メチル、アクリル酸エチル、アクリル酸イソプロピル
、アクリル酸−ｎ−ブチル、アクリル酸フェニル、アク
リル酸ベンジル、メタクリル酸メチル、メタクリル酸エ
チル、メタクリル酸イソプロピル、メタクリル酸−ｎ−
ブチル、メタクリル酸フェニル、メタクリル酸ベンジル
、エチレングリコールメタクリレート、ジエチレングリ
コールメタクリレート、アクロレイン、アクリロニトリ
ル、アクリルアミド、Ｎ、Ｎ’ −ジメチルアクリルア
ミド、スチレン、α−メチルスチレン、０−メチルスチ
レン、ｍ−メチルスチレン、ｐ−メチルスチレン、２，
６−シメチルスチレン、０−クロロスチレン、ｐ−クロ
ロスチレン、２゜４．６−トリクロロスチレン、酢酸ビ
ニル、プロピオン酸ビニル、クロル酢酸ビニル、エチレ
ン、プロピレン、イソブチレン、１，３−ブタジェンな
どが挙げられ、これらは２種以上混合して用いることも
できる。これらのビニル系単量体の中で特に好ましい単
量体はスチレン、メタクリル酸メチルおよび酢酸ビニル
である。In the present invention, a vinyl monomer copolymerizable with compound (I) is used. Examples of such vinyl monomers include methyl acrylate, ethyl acrylate, isopropyl acrylate, n-butyl acrylate, phenyl acrylate, benzyl acrylate, methyl methacrylate, ethyl methacrylate, isopropyl methacrylate, Methacrylic acid-n-
Butyl, phenyl methacrylate, benzyl methacrylate, ethylene glycol methacrylate, diethylene glycol methacrylate, acrolein, acrylonitrile, acrylamide, N,N'-dimethylacrylamide, styrene, α-methylstyrene, 0-methylstyrene, m-methylstyrene, p- methylstyrene, 2,
Examples include 6-dimethylstyrene, 0-chlorostyrene, p-chlorostyrene, 2゜4.6-trichlorostyrene, vinyl acetate, vinyl propionate, vinyl chloroacetate, ethylene, propylene, isobutylene, 1,3-butadiene, etc. These can also be used in combination of two or more types. Particularly preferred among these vinyl monomers are styrene, methyl methacrylate and vinyl acetate.
化合物（Ｉ）とビニル系単量体との配合割合は特に臨界
的なものではないが、化合物（■）１モル〜９９モルに
対し、ビニル系単量体９９〜１モル、好ましくは化合物
（Ｉ）１０〜９０モルに対し、ビニル系単量体９９〜１
モル配合するのが望ましい。The blending ratio of compound (I) and vinyl monomer is not particularly critical, but it is preferably 99 to 1 mol of vinyl monomer per 1 mol to 99 mol of compound (■), preferably compound (■). I) 99 to 1 vinyl monomer per 10 to 90 moles
It is desirable to mix moles.
本発明による新規な共重合体は、Ｎ−ｆｉ置換オキサビ
シクロ２，２．１コヘプト−５−エン−２゜３−ジカル
ボキシイミド化合物、およびこれと共重合可能なビニル
系単量体をラジカル重合開始剤の存在下、共重合させる
ことによって得ることができる。ラジカル開始剤として
は、ベンゾイルパーオキサイド、ラウロイルパーオキサ
イド、１−ブチルパーオキシ−２−エチルヘキサノエー
ト、ｔ−ブチルパーオキシイソプロピルカーボネート。The novel copolymer according to the present invention comprises a N-fi-substituted oxabicyclo 2,2.1-cohept-5-ene-2゜3-dicarboximide compound and a vinyl monomer copolymerizable with the same as a radical. It can be obtained by copolymerization in the presence of a polymerization initiator. Examples of radical initiators include benzoyl peroxide, lauroyl peroxide, 1-butylperoxy-2-ethylhexanoate, and t-butylperoxyisopropyl carbonate.
アゾイソブチロニトリル等の公知のものを挙げることが
できる。共重合反応は公知の懸濁重合、溶液重合および
バルク重合等のラジカル重合法により実施することがで
きる。共重合反応は通常、温度３０〜２００℃の範囲で
１〜２４時間行うのが、望ましい。Known ones such as azoisobutyronitrile can be mentioned. The copolymerization reaction can be carried out by known radical polymerization methods such as suspension polymerization, solution polymerization, and bulk polymerization. It is desirable that the copolymerization reaction is normally carried out at a temperature in the range of 30 to 200°C for 1 to 24 hours.
〈発明の効果〉
本発明によれば、従来知られていないＮ−置換オキサビ
シクロ［２，２，１］ヘプト−５−エン−２，３−ジカ
ルボキシイミド化合物とビニル系単量体とからなる新規
な共重合体を得ることができる。<Effects of the Invention> According to the present invention, from a hitherto unknown N-substituted oxabicyclo[2,2,1]hept-5-ene-2,3-dicarboximide compound and a vinyl monomer, A new copolymer can be obtained.
また、得られた新規な共重合体は、各種汎用樹脂とブレ
ンドすることにより、耐熱性の向上とともに、軟化点等
によって測定される熱安定性を向上させることができる
。Moreover, by blending the obtained novel copolymer with various general-purpose resins, it is possible to improve not only heat resistance but also thermal stability measured by softening point and the like.
〈実施例〉
以下、参考例、実施例及び比較例によって本発明を具体
的に説明するが、本実施例は本発明を限定するものでは
ない。<Example> The present invention will be specifically described below using reference examples, working examples, and comparative examples, but the present invention is not limited to the present invention.
見主班上
くＮ−シクロへキシルオキサビシクロ［２，２゜１］ヘ
プト−５−エン−２，３−ジカルボキシイミドの調製〉
Ｎ−シクロヘキシルマレイミド１７．６ｇ（０，１モル
）を６０ｍＱのトルエンに溶解し、フラン２０．４ｇ
（０，１モル）を撹拌しながら滴下した。滴下終了後、
３時間還流させながらさらに撹拌した。反応終了後、溶
媒を除去し、粗結晶１８．５ｇ （収率７５．０％）を
得た。シクロヘキサンにより再結晶を行ない、最終的に
収率６２．３％にて目的物１５．４ｇを得た。Preparation of N-cyclohexyloxabicyclo[2,2゜1]hept-5-ene-2,3-dicarboximide> 17.6 g (0.1 mol) of N-cyclohexylmaleimide was added to 60 mQ 20.4g of furan dissolved in toluene
(0.1 mol) was added dropwise with stirring. After finishing dropping,
The mixture was further stirred while refluxing for 3 hours. After the reaction was completed, the solvent was removed to obtain 18.5 g of crude crystals (yield: 75.0%). Recrystallization was performed using cyclohexane, and 15.4 g of the target product was finally obtained with a yield of 62.3%.
蔓工旌Ｉ
くＮ−フェニルオキサビシクロ［２，２，１１ヘプト−
５−エン−２，３−ジカルボキシイミドの調製〉
Ｎ−シクロへキシルマレイミドを、Ｎ−フェニルマレイ
ミド１７．３ｇ （０，１モル）とした以外は参考例１
と同様にしてＮ−フェニルオキサビシクロ［２，２，１
］ヘプト−５−エン−２，３−ジカルボキシイミドを調
製した。Vine Kogyo I KuN-phenyloxabicyclo[2,2,11hept-
Preparation of 5-ene-2,3-dicarboximide> Reference Example 1 except that 17.3 g (0.1 mol) of N-phenylmaleimide was used instead of N-cyclohexylmaleimide.
In the same manner as N-phenyloxabicyclo[2,2,1
] Hept-5-ene-2,3-dicarboximide was prepared.
収量は２０．１ｇ （収率８３．３％）であった。The yield was 20.1 g (yield 83.3%).
更炙孤立
〈Ｎ−ベンジルオキサビシクロ［２，２，１］ヘプト−
５−エン−２，３−ジカルボキシイミドの！ｌｉ製〉
Ｎ−シクロヘキシルマレイミドを、Ｎ−ベンジルマレイ
ミド１８．７ｇ （０，１モル）とした以外は参考例１
と同様にしてＮ−ベンジルオキサビシクロ［２，２，１
］ヘプト−５−エン−２，３−ジカルボキシイミドを調
製した。Sararoki isolated〈N-benzyloxabicyclo[2,2,1]hept-
of 5-ene-2,3-dicarboximide! Made by Li> Reference Example 1 except that 18.7 g (0.1 mol) of N-benzylmaleimide was used instead of N-cyclohexylmaleimide.
In the same manner as N-benzyloxabicyclo[2,2,1
] Hept-5-ene-2,3-dicarboximide was prepared.
収量は２０．７ｇ （収率８１．１％）であった。The yield was 20.7 g (yield 81.1%).
去Ｗご」−
バイレッ々スガラス重合管に表１に示す組成にて参考例
１〜３にて調製したＮ−シクロへキシルオキサビシクロ
［２，２，１］ヘプト−５−エン−２，３−ジカルボキ
シイミド（以下ＣＨ○と略す）、Ｎ−フェニルオキサビ
シクロ［２，２，１］ヘプト−５−エン−２，３−ジカ
ルボキシイミド（以下Ｐｈｏと略す）又はＮ−ベンジル
オキサビシクロ［２，２，１］ヘプト−５−エン−２，
３ジカルボキシイミド（以下ＢｚＯと略す）と共重合可
能なビニル系単量体（コモノマーＭ２と略す）及び２，
５−ジメチル−２，５−ジｔ−ブチルペルオキシヘキシ
ン−３（商品名［パーヘキシン−２５ＢＪ日本油脂（株
）１２重合開始剤）を秤り取り、冷媒に浸した後真空脱
気（０，０ＩＴｏｒｒ） シ、乾燥窒素ガスを導入した
。そして通常行われる液−面状態をくり返し封管した後
重合反応を行った。- N-cyclohexyloxabicyclo[2,2,1]hept-5-ene-2,3 prepared in Reference Examples 1 to 3 with the composition shown in Table 1 in a Bayless glass polymerization tube. -dicarboximide (hereinafter abbreviated as CH○), N-phenyloxabicyclo[2,2,1]hept-5-ene-2,3-dicarboximide (hereinafter abbreviated as Pho) or N-benzyloxabicyclo[ 2,2,1]hept-5-ene-2,
3 A vinyl monomer (abbreviated as comonomer M2) copolymerizable with dicarboximide (hereinafter abbreviated as BzO), and 2,
5-Dimethyl-2,5-di-t-butylperoxyhexine-3 (trade name: Perhexine-25BJ Nippon Oil & Fats Co., Ltd. 12 polymerization initiator) was weighed out, immersed in a refrigerant, and then vacuum degassed (0, 0ITorr) Dry nitrogen gas was introduced. Then, the tube was repeatedly sealed in the liquid level state that is normally carried out, and then a polymerization reaction was carried out.
重合後、過剰のメタノール中に重合物を投じて沈殿させ
、得られた共重合体を炉別し、メタノールでよく洗浄し
、真空乾燥させた。重合反応結果を表２に示す。After polymerization, the polymer was poured into excess methanol to precipitate it, and the resulting copolymer was separated in a furnace, thoroughly washed with methanol, and dried under vacuum. Table 2 shows the polymerization reaction results.
よ較射↓二附
実施例１〜８に準じてスチレン、メタアクリル酸メチル
、酢酸ビニルのホモ重合体を各々製造した。重合反応結
果を表２に示す。Homopolymers of styrene, methyl methacrylate, and vinyl acetate were each produced according to Examples 1 to 8 of the appendix. Table 2 shows the polymerization reaction results.
Claims (1)
基、分岐アルキル基、シクロアルキル基、アリール基ま
たはアラルキル基を表わす。）で示されるＮ−置換オキ
サビシクロ［２，２，１］ヘプト−５−エン−２，３−
ジカルボキシイミド化合物およびこれと共重合可能なビ
ニル系単量体を共重合してなる耐熱性樹脂。[Claims] General formula (I) ▲Mathematical formulas, chemical formulas, tables, etc.▼(I) (In the formula, R is a hydrogen atom, a straight chain alkyl group having 1 to 18 carbon atoms, a branched alkyl group, a cycloalkyl group) N-substituted oxabicyclo[2,2,1]hept-5-ene-2,3-
A heat-resistant resin made by copolymerizing a dicarboximide compound and a vinyl monomer copolymerizable with the dicarboximide compound.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP14054088A JPH01311112A (en) | 1988-06-09 | 1988-06-09 | Novel heat-resistant resin |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP14054088A JPH01311112A (en) | 1988-06-09 | 1988-06-09 | Novel heat-resistant resin |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH01311112A true JPH01311112A (en) | 1989-12-15 |
Family
ID=15271049
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP14054088A Pending JPH01311112A (en) | 1988-06-09 | 1988-06-09 | Novel heat-resistant resin |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH01311112A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9212241B2 (en) | 2011-12-28 | 2015-12-15 | Samsung Electronics Co., Ltd. | Optical film and display device including same |
-
1988
- 1988-06-09 JP JP14054088A patent/JPH01311112A/en active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9212241B2 (en) | 2011-12-28 | 2015-12-15 | Samsung Electronics Co., Ltd. | Optical film and display device including same |
| US9856353B2 (en) | 2011-12-28 | 2018-01-02 | Samsung Electronics Co., Ltd. | Optical film and display device including same |
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