JPH0273829A - Maleimide based polymer having peroxy bond in molecule - Google Patents
Maleimide based polymer having peroxy bond in moleculeInfo
- Publication number
- JPH0273829A JPH0273829A JP22423688A JP22423688A JPH0273829A JP H0273829 A JPH0273829 A JP H0273829A JP 22423688 A JP22423688 A JP 22423688A JP 22423688 A JP22423688 A JP 22423688A JP H0273829 A JPH0273829 A JP H0273829A
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- JP
- Japan
- Prior art keywords
- group
- formulas
- tables
- formula
- carbon atoms
- 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
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- 229920000642 polymer Polymers 0.000 title claims abstract description 35
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 title claims description 22
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 18
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 18
- 125000004956 cyclohexylene group Chemical group 0.000 claims description 6
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 5
- 125000003107 substituted aryl group Chemical group 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 10
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 150000002978 peroxides Chemical class 0.000 abstract description 10
- 229920001400 block copolymer Polymers 0.000 abstract description 6
- -1 maleimide compound Chemical class 0.000 abstract description 6
- 239000002243 precursor Substances 0.000 abstract description 6
- 239000003607 modifier Substances 0.000 abstract description 5
- 239000011347 resin Substances 0.000 abstract description 4
- 229920005989 resin Polymers 0.000 abstract description 4
- 238000006116 polymerization reaction Methods 0.000 description 12
- 239000000178 monomer Substances 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 238000010521 absorption reaction Methods 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 239000004793 Polystyrene Substances 0.000 description 7
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 7
- 125000000864 peroxy group Chemical group O(O*)* 0.000 description 7
- 229920002223 polystyrene Polymers 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 238000000862 absorption spectrum Methods 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 229910001873 dinitrogen Inorganic materials 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- GTYRFVGHYNRSKT-UHFFFAOYSA-N 3-benzylpyrrole-2,5-dione Chemical compound O=C1NC(=O)C(CC=2C=CC=CC=2)=C1 GTYRFVGHYNRSKT-UHFFFAOYSA-N 0.000 description 3
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical group C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 3
- PWAXUOGZOSVGBO-UHFFFAOYSA-N adipoyl chloride Chemical compound ClC(=O)CCCCC(Cl)=O PWAXUOGZOSVGBO-UHFFFAOYSA-N 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 150000003949 imides Chemical class 0.000 description 3
- 230000000977 initiatory effect Effects 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 238000010926 purge Methods 0.000 description 3
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- DABFKTHTXOELJF-UHFFFAOYSA-N 1-propylpyrrole-2,5-dione Chemical compound CCCN1C(=O)C=CC1=O DABFKTHTXOELJF-UHFFFAOYSA-N 0.000 description 2
- UJTRCPVECIHPBG-UHFFFAOYSA-N 3-cyclohexylpyrrole-2,5-dione Chemical compound O=C1NC(=O)C(C2CCCCC2)=C1 UJTRCPVECIHPBG-UHFFFAOYSA-N 0.000 description 2
- UDBZRZHFPQBTAC-UHFFFAOYSA-N 3-cyclohexylpyrrole-2,5-dione;styrene Chemical compound C=CC1=CC=CC=C1.O=C1NC(=O)C(C2CCCCC2)=C1 UDBZRZHFPQBTAC-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- 239000004372 Polyvinyl alcohol Substances 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000005227 gel permeation chromatography Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000005022 packaging material Substances 0.000 description 2
- 229920002451 polyvinyl alcohol Polymers 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 229920006132 styrene block copolymer Polymers 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- 125000006702 (C1-C18) alkyl group Chemical group 0.000 description 1
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 description 1
- QYOJZFBQEAZNEW-UHFFFAOYSA-N 1-(2-methylphenyl)pyrrole-2,5-dione Chemical compound CC1=CC=CC=C1N1C(=O)C=CC1=O QYOJZFBQEAZNEW-UHFFFAOYSA-N 0.000 description 1
- QBBOVTQQOKBHBD-UHFFFAOYSA-N 1-(3-propan-2-ylphenyl)pyrrole-2,5-dione Chemical compound CC(C)C1=CC=CC(N2C(C=CC2=O)=O)=C1 QBBOVTQQOKBHBD-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
- BQTPKSBXMONSJI-UHFFFAOYSA-N 1-cyclohexylpyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1CCCCC1 BQTPKSBXMONSJI-UHFFFAOYSA-N 0.000 description 1
- SJLLJZNSZJHXQN-UHFFFAOYSA-N 1-dodecylpyrrole-2,5-dione Chemical compound CCCCCCCCCCCCN1C(=O)C=CC1=O SJLLJZNSZJHXQN-UHFFFAOYSA-N 0.000 description 1
- HOLZCMFSCBLOLX-UHFFFAOYSA-N 1-octadecylpyrrole-2,5-dione Chemical compound CCCCCCCCCCCCCCCCCCN1C(=O)C=CC1=O HOLZCMFSCBLOLX-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
- GJFDBYRHAZJJBP-UHFFFAOYSA-N 3-tert-butylpyrrole-2,5-dione Chemical compound CC(C)(C)C1=CC(=O)NC1=O GJFDBYRHAZJJBP-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 1
- GHAZCVNUKKZTLG-UHFFFAOYSA-N N-ethyl-succinimide Natural products CCN1C(=O)CCC1=O GHAZCVNUKKZTLG-UHFFFAOYSA-N 0.000 description 1
- HDFGOPSGAURCEO-UHFFFAOYSA-N N-ethylmaleimide Chemical compound CCN1C(=O)C=CC1=O HDFGOPSGAURCEO-UHFFFAOYSA-N 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- 229920002845 Poly(methacrylic acid) Polymers 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 238000012662 bulk polymerization Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 125000005439 maleimidyl group Chemical group C1(C=CC(N1*)=O)=O 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- SEEYREPSKCQBBF-UHFFFAOYSA-N n-methylmaleimide Chemical compound CN1C(=O)C=CC1=O SEEYREPSKCQBBF-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- PFUVRDFDKPNGAV-UHFFFAOYSA-N sodium peroxide Chemical compound [Na+].[Na+].[O-][O-] PFUVRDFDKPNGAV-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000010557 suspension polymerization reaction Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
Landscapes
- Graft Or Block Polymers (AREA)
- Other Resins Obtained By Reactions Not Involving Carbon-To-Carbon Unsaturated Bonds (AREA)
Abstract
Description
【発明の詳細な説明】
〈産業」二の利用分野〉
本発明は分子内にペルオキシ結合を有するマレイミド系
重合体に関し、更に詳細には、耐熱性に優れ、マレイミ
ド系ブロック共重合体の前駆体として、また他の樹脂の
改質材として利用できる新規な分子内にペルオキシ結合
を有するマレイミド系重合体に関する。[Detailed Description of the Invention] <Field of Application in Industry> The present invention relates to a maleimide-based polymer having peroxy bonds in the molecule, and more specifically, to a maleimide-based block copolymer precursor having excellent heat resistance. This invention relates to a novel maleimide polymer having a peroxy bond in the molecule, which can be used as a modifier for other resins.
〈従来の技術〉
分子内にペルオキシ結合を有するビニル重合体としては
、杉材ら、王化誌69巻718頁(1966)に。<Prior Art> Vinyl polymers having peroxy bonds in the molecule are described by Sugizai et al., Wangka Shi, Vol. 69, p. 718 (1966).
分子内にペルオキシ結合を有するポリスチレンが。Polystyrene has peroxy bonds within the molecule.
また特公昭62−14567号公報に、分子内にペルオ
キシ結合を有するポリスチレン、ポリ酢酸ビニル、ポリ
メタクリル酸エステル、ポリ塩化ビニル等が開示されて
いる。Furthermore, Japanese Patent Publication No. 14567/1987 discloses polystyrene, polyvinyl acetate, polymethacrylic acid ester, polyvinyl chloride, etc., each having a peroxy bond in the molecule.
しかしながら、前述の刊行物において、マレイミド系重
合体については何等示されていない。However, the above-mentioned publications do not disclose anything about maleimide polymers.
〈発明が解決しようとする課題〉
本発明の目的は、取扱いが容易であり、耐熱性に優れ、
且つマレイミド系ブロック共重合体の1)1駆体として
、また他の樹脂の改質材として利用できる分子内にペル
オキシ結合を有するマレイミド系重合体を提供すること
にある。<Problems to be Solved by the Invention> The objects of the present invention are to provide a material that is easy to handle, has excellent heat resistance, and
Another object of the present invention is to provide a maleimide polymer having a peroxy bond in its molecule, which can be used as a 1) precursor of a maleimide block copolymer and as a modifier for other resins.
〈課題を解決するための手段〉
本発明によれば、下記−殺伐(1)
(式中R0及びR2は夫々水素原子、ハロゲン原子又は
メチル基を示し、R3は炭素数1〜18の直鎖又は分枝
アルキル基、炭素数3〜12のシクロアルキル基、炭素
数6〜18のアリール基又は置換アリール基を示す。)
で表わされる構成単位90〜99.9重量%と、
次の3種の一般式(II)〜(TV)
(式中R4は炭素数2〜10のアルキレン基を示し、■
<、は炭素数2〜10のアルキレン基、−CH2CH□
0C(1□C]12−又は−CI、CH20CH2CH
20C1(2C11□−を示す。)。<Means for Solving the Problems> According to the present invention, the following: or a branched alkyl group, a cycloalkyl group having 3 to 12 carbon atoms, an aryl group having 6 to 18 carbon atoms, or a substituted aryl group.)
90 to 99.9% by weight of structural units represented by the following three general formulas (II) to (TV) (wherein R4 represents an alkylene group having 2 to 10 carbon atoms,
<, is an alkylene group having 2 to 10 carbon atoms, -CH2CH□
0C(1□C]12- or -CI, CH20CH2CH
20C1 (indicates 2C11□-).
(式中R5は−C(CH,)z C1l□CH2C(C
I、 )2−1−C(CH3)2−O−C(CH,)2
−1R7は炭素数2〜10のアルキレン基、シクロヘキ
シレン基又はフェニレン基を示す。)及び(式中R,は
、炭素数2〜10のアルキレン基、シクロヘキシレン基
又はフェニレン基を示し、■<。(In the formula, R5 is -C(CH,)z C1l□CH2C(C
I, )2-1-C(CH3)2-O-C(CH,)2
-1R7 represents an alkylene group having 2 to 10 carbon atoms, a cyclohexylene group, or a phenylene group. ) and (in the formula, R represents an alkylene group having 2 to 10 carbon atoms, a cyclohexylene group, or a phenylene group, and ■<.
は−C(CH2)2 CH2CH2C(CHz )2−
1−C(CH,)2−O−C(CH,、ルー、C(CH
s)z−OC(CH3)2−を示す。)から成る群の1
種又は2種以上より選択されるペルオキシ結合を含む構
成単位0.1〜10重量%とからなり、粘度平均分子量
1700〜530000であることを特徴とする分子内
にペルオキシ結合を有するマレイミド系重合体が提供さ
れる。is -C(CH2)2 CH2CH2C(CHz )2-
1-C(CH,)2-O-C(CH,, Roux, C(CH
s) z-OC(CH3)2-. ) of the group consisting of
A maleimide polymer having a peroxy bond in the molecule, comprising 0.1 to 10% by weight of a structural unit containing a peroxy bond selected from one species or two or more types, and having a viscosity average molecular weight of 1,700 to 530,000. is provided.
以下更に詳細に説明する。This will be explained in more detail below.
本発明の分子内にペルオキシ結合を有するマレ−c(c
x−r、)2−■−c(c■−r、)、−を示し、
イミド系重合体は、マレイミド化合物構成単位(以T:
MICと略す。)と特定のポリメリックペルオキシド構
成単位(以下PMPOCと略す。)とを特定の割合で含
むことを特徴とする。Male-c (c) having a peroxy bond in the molecule of the present invention
x-r,)2-■-c(c■-r,),-, and the imide polymer is a maleimide compound structural unit (hereinafter T:
It is abbreviated as MIC. ) and a specific polymeric peroxide structural unit (hereinafter abbreviated as PMPOC) in a specific ratio.
本発明に用いる前記MICは、下記−殺伐(I)にて表
わすことができ、
K。The above-mentioned MIC used in the present invention can be represented by the following - killing (I), K.
(式中R1及びR2は夫々水素原子、ハロゲン原子又は
メチル基を示し、R3は炭素数1〜18アルキル基、炭
素数3〜10のシクロアルキル基、炭素数6〜18のア
リール基又は置換アリール基を示す。この際R1が炭素
数19以上のアルキル基、炭素数11以上のシクロアル
キル基又は炭素数19以」二の7リール基若しくは置換
アリール基である場合には製造が困難となるので使用で
きない。前記−殺伐(1)にて示されるMICとを形成
するモノマーとしては、例えば、N−メチルマレイミド
、N−エチルマレイミド、N−n−プロピルマレイミド
、N−1−プロピルマレイミド、N−tブチルマレイミ
ド、N−ドデシルマレイミド、N−オクタデシルマレイ
ミド、N−フェニルマレイミド、N−2−メチルフェニ
ルマレイミド、N−3−イソプロピルフェニルマレイミ
ド、N−シクロへキシルマレイミド及びN−ベンジルマ
レイミド等から成る群の1種又は2種以−ヒより選択さ
れる化合物又は混合物を好ましく挙げることができる。(In the formula, R1 and R2 each represent a hydrogen atom, a halogen atom, or a methyl group, and R3 is a C1-C18 alkyl group, a C3-10 cycloalkyl group, a C6-18 aryl group, or a substituted aryl group) In this case, if R1 is an alkyl group having 19 or more carbon atoms, a cycloalkyl group having 11 or more carbon atoms, a 7-aryl group having 19 or more carbon atoms, or a substituted aryl group, production will be difficult. Cannot be used. Examples of monomers that form the MIC shown in -killing (1) include N-methylmaleimide, N-ethylmaleimide, N-n-propylmaleimide, N-1-propylmaleimide, N- A group consisting of t-butylmaleimide, N-dodecylmaleimide, N-octadecylmaleimide, N-phenylmaleimide, N-2-methylphenylmaleimide, N-3-isopropylphenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, etc. Preferred examples include compounds or mixtures selected from one or more of the following.
本発明に用いる前記PMPOCは、下記−殺伐(If)
、(I[I)又は(IV)で表わすことができ、式中R
4は炭素数2〜10のアルキレン基を示し。The PMPOC used in the present invention has the following - killing (If)
, (I[I) or (IV), in which R
4 represents an alkylene group having 2 to 10 carbon atoms.
R9は炭素数2〜10のアルキレン基、C)I、CIl
、0CR2CH,−又は−CH2CH20CH2CH2
0cH2CH,−を示す。またR6は−C(CI(i)
zCH2CH2C(CHa)z−1−c(cH,>z−
O−c<crr3)2−1C(CR3)z @ C(C
H3)z−を示し、R7はm素数2〜10のアルキレン
基、シクロヘキシレン基又はフェニレン基を示す。更に
式中R,ハ、炭素数2〜10のアルキレン基、シクロヘ
キシレン基又はフェニレン基を示し、R9はC(CI、
)、 CH2Cl1□c(CI3’)2−1c(cr
r、)2−O−c(cHJ)2−1物干ツマ−との重合
性が良好であって、得られるマレイミド系重合体中にお
いて、ペルオキシ基が熱的に安定に存在することができ
る。更に重合開始剤としての役割も同時にはだすので、
重合開始能率にも非常に優れたものである。R9 is an alkylene group having 2 to 10 carbon atoms, C)I, CIl
, 0CR2CH, - or -CH2CH20CH2CH2
Indicates 0cH2CH,-. Also, R6 is -C(CI(i)
zCH2CH2C(CHa)z-1-c(cH,>z-
O-c<crr3)2-1C(CR3)z @C(C
H3) represents z-, and R7 represents an alkylene group, a cyclohexylene group, or a phenylene group in which m has a prime number of 2 to 10. Further, in the formula, R, C represents an alkylene group having 2 to 10 carbon atoms, a cyclohexylene group, or a phenylene group, and R9 represents C(CI,
), CH2Cl1□c(CI3')2-1c(cr
r,)2-O-c(cHJ)2-1 has good polymerizability with the drying agent, and the peroxy group can exist thermally stably in the resulting maleimide polymer. . Furthermore, since it also plays a role as a polymerization initiator,
It also has excellent polymerization initiation efficiency.
本発明に用いる前記−殺伐(n)で示されるI〕MPO
Cはジアシル型であり、例えば特公昭62−14567
号公報に記載される方法等により製造することができる
。該ジアシル型ポリメリックペルオキシドとしては、例
えば、
c(cr(、)z−■−c(cIia)z−を示す。I] MPO used in the present invention, denoted by the above-denoted (n)
C is diacyl type, for example, Japanese Patent Publication No. 62-14567
It can be manufactured by the method described in the above publication. Examples of the diacyl polymeric peroxide include c(cr(,)z-■-c(cIia)z-.
前記−殺伐(IT) −(IV) テ表わされるPMP
○Cを形成するモノマーは、前記マレイミド化合(n=
2〜20の正数を示す。)等を好ましく挙げることがで
きる。Said - Extermination (IT) - (IV) PMP expressed by Te
The monomer forming ○C is the maleimide compound (n=
Indicates a positive number from 2 to 20. ) etc. can be preferably mentioned.
また本発明に用いる前記−殺伐(I[r)で示されるP
MPOCは、エステル型であり5例えば二塩基酸ジクロ
ライドとアルキレンジヒドロペルオキシドとを水酸化ナ
トリウム水溶液存在下、反応させる方法等番こより製造
することができる。Mエステル型ポリメリックペルオキ
シドとしては、例えば
(n=2〜20の正数を示す。)等を好ましく挙げるこ
とができる。In addition, P represented by the above-mentioned -killing (I[r)] used in the present invention
MPOC is an ester type and can be produced, for example, by a method in which dibasic acid dichloride and alkylene dihydroperoxide are reacted in the presence of an aqueous sodium hydroxide solution. Preferred examples of the M ester type polymeric peroxide include (n = a positive number of 2 to 20).
更に本発明に用いる前記−殺伐(IV)で示されるPM
POCは、カーボネート型であり1例えば2価のアルコ
ールにホスゲンを反応させる方法等により製造すること
ができ、具体的には、アルキレンジクロロホルメートと
ジヒドロペルオキシドとを水酸化ナトリウム水溶液存在
下、反応させる方法等により得ることができる。該カー
ボネー1−型ボリメリックペルオキシドとしては、例え
ば等を好ましく挙げることができる。Further, the PM represented by -killing (IV) used in the present invention
POC is a carbonate type and can be produced by, for example, reacting a dihydric alcohol with phosgene, and specifically, by reacting an alkylene dichloroformate with a dihydroperoxide in the presence of an aqueous sodium hydroxide solution. It can be obtained by a method etc. Preferred examples of the carbonate 1-type polymeric peroxide include the following.
本発明の分子内にペルオキシ結合を有するマレイミド系
重合体は、前記MICと、前記−殺伐HI)で示される
PMPOC,前記−殺伐(III)で示されるPMPO
C及び前記−殺伐(IV)で示されるPMPOCから成
る群の1種又は2種以上より選択されるPMPOCとの
重合体であって、前記PMPOCの選択は、ペルオキシ
結合の10時間半減期温度(10時間後にペルオキシ基
の濃度が半分になる温度で、ペルオキシ基の熱分解速度
の指数)及び溶解性等に基づいて行なわれる。The maleimide polymer having a peroxy bond in the molecule of the present invention has the above-mentioned MIC, PMPOC shown by the above-mentioned -Sakatsu HI), and PMPO shown by the above-mentioned -Sakatsu (III).
C and PMPOC selected from one or more of the group consisting of PMPOC represented by -killing (IV), wherein the selection of the PMPOC is based on the 10-hour half-life temperature of the peroxy bond ( This is carried out at a temperature at which the concentration of peroxy groups becomes half after 10 hours, based on the index of thermal decomposition rate of peroxy groups), solubility, etc.
また本発明の分子内にペルオキシ結合を有するマレイミ
ド重合体を用いて他のビニルモノマーを重合してブロッ
ク重合体を製造する際に好ましいペルオキシ結合、即ち
10時間半減期温度及び重合開始効率も考慮して選択さ
れる。前記MIC及びPMPOC夫々ノ含夫々金含有割
合C90−99,9重量でに対し、 PMPOC0,1
〜10重量%の割合である。この際MICの含有割合が
99.9重量%を超える場合、即ち、PMPOCの含有
割合が0.1重量%未満の場合には、PMPOCの含有
割合が少なすぎて。In addition, when producing a block polymer by polymerizing other vinyl monomers using the maleimide polymer having a peroxy bond in the molecule of the present invention, the preferable peroxy bond, that is, the 10-hour half-life temperature and polymerization initiation efficiency are also taken into consideration. selected. The respective gold content ratios of the MIC and PMPOC are C90-99,9 by weight, and PMPOC0,1
The proportion is ~10% by weight. At this time, if the MIC content exceeds 99.9% by weight, that is, if the PMPOC content is less than 0.1% by weight, the PMPOC content is too small.
ブロック共重合体の前駆体又は改質剤として使用できな
い。またMICの含有割合が90重量%未満の場合、即
ちPMPOCの含有割合が10重量%を超える場合には
、PMPOCが高濃度となり、取扱い上の危険性が生じ
、貯蔵安定性が低下する。Cannot be used as a precursor or modifier for block copolymers. Further, when the content of MIC is less than 90% by weight, that is, when the content of PMPOC exceeds 10% by weight, the concentration of PMPOC becomes high, creating a handling hazard and reducing storage stability.
前記MICとPMPOCとの含有量を調べるには、得ら
れた分子内にペルオキシ結合を有するマレイミド系重合
体中の全窒素量をケルブール法等により測定することに
よって、MICの含有量を、また活性酸素量をヨードメ
トリー法等により測定することによって、PMPOCの
含有量を定量することができる。In order to investigate the content of MIC and PMPOC, the total nitrogen content in the obtained maleimide polymer having peroxy bonds in the molecule is measured by the Kerbourg method, etc., and the content of MIC and activity The content of PMPOC can be determined by measuring the amount of oxygen by iodometry or the like.
本発明の分子内にペルオキシ結合を有するマレイミド系
重合体の粘度平均分子量は1700〜530000の範
囲である。この際該粘度平均分子量が1700未満の場
合には1分子量が少なくなり、耐熱性に優れたブロック
共重合体を製造するための前駆体とならないので好まし
くなく、また、530000を超える場合には、溶媒へ
の溶解性が低下し、不純物の除去が困難となるので好ま
しくない。本発明にて規定する粘度平均分子量とは、極
限粘度から求めたポリスチレン換算粘度平均分子量であ
る。The viscosity average molecular weight of the maleimide polymer having peroxy bonds in the molecule of the present invention is in the range of 1,700 to 530,000. In this case, if the viscosity average molecular weight is less than 1,700, the molecular weight per molecular weight will decrease and it will not be a precursor for producing a block copolymer with excellent heat resistance, which is not preferable, and if it exceeds 530,000, This is not preferred because the solubility in the solvent decreases and it becomes difficult to remove impurities. The viscosity average molecular weight defined in the present invention is the viscosity average molecular weight in terms of polystyrene determined from the intrinsic viscosity.
すなオ〕ち粘度平均分子量は極限粘度(’1.)から下
記(1)式より求められ、極限粘度数0.02〜1.6
は、ポリスチレン換算粘度平均分子量1700〜530
000に相当する。In other words, the viscosity average molecular weight is determined from the intrinsic viscosity ('1.) by the following formula (1), and the intrinsic viscosity number is 0.02 to 1.6.
is polystyrene equivalent viscosity average molecular weight 1700-530
Corresponds to 000.
(n)=K・ (−M v )’ ・・・ (1
)(式中には定数であり、K X 10103(100
/ g )=0.0716である。またα=9.76は
25℃、クロロホルム溶液中のポリスチレンの数値であ
る。)(ワイリー・インターサイエンス社版「ポリマー
ハンドブック」第2版IV−17)。(n)=K・(-Mv)'...(1
) (is a constant in the formula, K X 10103 (100
/g)=0.0716. Further, α=9.76 is the numerical value of polystyrene in a chloroform solution at 25°C. ) ("Polymer Handbook" 2nd edition IV-17, published by Wiley Interscience).
本発明において、得られたマレイミド系重合体の粘度平
均分子量は、ゲルパーミェーションクロマトグラフィ(
GPC)等により測定することができる。In the present invention, the viscosity average molecular weight of the obtained maleimide polymer can be determined by gel permeation chromatography (
GPC) and the like.
本発明の分子内にペルオキシ結合を有するマレイミド系
重合体を製造するには、例えば溶液重合法、懸濁重合法
、塊状重合法等の公知の重合法により製造することがで
きる。具体的には前記MICモノマーと前記PMPOC
モノマーとを、好ましくは、重合温度
40〜120℃、重合時間3〜20時間の範囲で重合す
ることにより製造することができる。この際のMICモ
ノマーとPMPOCモノマーとの仕込み量は、MICモ
ノマー100重量部に対して。The maleimide polymer having peroxy bonds in the molecule of the present invention can be produced by known polymerization methods such as solution polymerization, suspension polymerization, and bulk polymerization. Specifically, the MIC monomer and the PMPOC
Monomers, preferably at a polymerization temperature of 40 to 120°C and a polymerization time of 3 to 20 hours. The amounts of the MIC monomer and PMPOC monomer at this time are based on 100 parts by weight of the MIC monomer.
PMPOCモノマー0,2〜30重量部、特に好ましく
は0.5〜20重量部であることが望ましい。前記PM
POCモノマーの仕込み量が0.2重量部未満の場合に
は、重合速度が著しく低下し、また生成した分子内にペ
ルオキシ結合を有するマレイミド系重合体中のペルオキ
シ基濃度が低いので好ましくなく、また30重量部を超
える場合には、ペルオキシ基濃度が高すぎて1重合反応
が暴走する恐れがあるので好ましくない。Preferably, the amount of PMPOC monomer is from 0.2 to 30 parts by weight, particularly preferably from 0.5 to 20 parts by weight. Said PM
If the amount of POC monomer charged is less than 0.2 parts by weight, the polymerization rate will drop significantly and the concentration of peroxy groups in the maleimide polymer having peroxy bonds in the produced molecules will be low, which is not preferable. If it exceeds 30 parts by weight, the peroxy group concentration will be too high and the monopolymerization reaction may run out of control, which is not preferable.
〈発明の効果〉
本発明の分子内にペルオキシ結合を有するマレイミド系
重合体は、耐熱性の高いMICとラジカル重合開始能を
有するPMPOCとから構成されるので、安全性、貯蔵
安定性及び取扱い性に優れ、且つマレイミド系ブロック
共重合体の前駆体として、また他の樹脂の改質剤として
利用することができる。<Effects of the Invention> The maleimide polymer having a peroxy bond in the molecule of the present invention is composed of MIC with high heat resistance and PMPOC with radical polymerization initiating ability, so it has excellent safety, storage stability, and ease of handling. It has excellent properties and can be used as a precursor for maleimide block copolymers and as a modifier for other resins.
〈実施例〉
以下、参考例及び実施例により更に詳細に説明するが本
発明はこれらに限定されるものではない。<Examples> The present invention will be explained in more detail below using reference examples and examples, but the present invention is not limited thereto.
温度計、撹拌機を備えた4つ目フラスコに、アジピン酸
クロライド183部とトリエチレングリコール75部と
を仕込んだ。次いで窒素ガス気流下、20℃で60分間
撹拌したところ、粘稠な無色の液体のトリエチレングリ
コールビス(アジポイルクロラド)210部が得られた
。A fourth flask equipped with a thermometer and a stirrer was charged with 183 parts of adipic acid chloride and 75 parts of triethylene glycol. The mixture was then stirred at 20° C. for 60 minutes under a nitrogen gas stream to obtain 210 parts of triethylene glycol bis(adipoyl chloride) as a viscous colorless liquid.
次に温度計、撹拌機1滴下ロートを備えた4つロフラス
コに50%過酸化水素水と10%水酸化ナトリウム水溶
液420部とを仕込み、過酸化ナトリウム水溶液を11
製した。その後激しく撹拌しながら反応温度を5℃に保
ち、先に調製したトリエチレングリコールビス(アジポ
イルクロライド)176部を20分間かけて滴下した。Next, 50% hydrogen peroxide solution and 420 parts of 10% sodium hydroxide solution were placed in a four-bottle flask equipped with a thermometer, a stirrer, and a dropping funnel, and 11 parts of the sodium peroxide solution was added.
Manufactured. Thereafter, while stirring vigorously and keeping the reaction temperature at 5° C., 176 parts of the previously prepared triethylene glycol bis(adipoyl chloride) was added dropwise over 20 minutes.
そのまま30分間撹拌を続けたところ、白色固体が生成
した。When stirring was continued for 30 minutes, a white solid was produced.
これを濾過し、IQの冷水で2度洗浄した後、真空乾燥
させて白色の粉末140部を得た。得られた白色粉末の
分子量を蒸気圧平衡法分子量測定装置(日立製作所製r
VPo−115型」)で測定したところ2340 (n
弁5.8)であった。ヨードメトリー法で測定した活性
酸素量は2.19%であった。従って純度は99.5%
であった。また赤外吸収スペクトルは1725cm−”
にエステル基のカルボニル基の吸収が、1.780 。This was filtered, washed twice with IQ cold water, and then vacuum dried to obtain 140 parts of a white powder. The molecular weight of the obtained white powder was measured using a vapor pressure equilibrium molecular weight measuring device (manufactured by Hitachi, Ltd.).
2340 (n
The valve was 5.8). The amount of active oxygen measured by iodometry was 2.19%. Therefore, the purity is 99.5%
Met. In addition, the infrared absorption spectrum is 1725 cm-”
The absorption of the carbonyl group of the ester group is 1.780.
1805as−”にジアシル基のカルボニル基の吸収が
、更に875ai−”にペルオキシ基の吸収が認められ
た。Absorption of the carbonyl group of the diacyl group was observed at 1805as-'', and absorption of the peroxy group was further observed at 875ai-''.
ヌ】111
温度計、撹拌機及びジムロート冷却器を備えた4つ目フ
ラスコに、0.5重量%のポリビニルアルコール水溶液
250部を仕込んだ。次にシクロへキシルマレイミド8
0部と参考例1で合成した10部とをメチルエチルケト
ン20部に分散させ仕込んだ。次いで反応器内を窒素ガ
スで置換しながら撹拌下に75℃で3時間重合させた。111 A fourth flask equipped with a thermometer, a stirrer, and a Dimroth condenser was charged with 250 parts of a 0.5% by weight aqueous polyvinyl alcohol solution. Next, cyclohexylmaleimide 8
0 parts and 10 parts synthesized in Reference Example 1 were dispersed and charged in 20 parts of methyl ethyl ketone. Next, polymerization was carried out at 75° C. for 3 hours while stirring while purging the inside of the reactor with nitrogen gas.
生成した重合物を戸別し、水洗した後クロロホルムに溶
解させ、次いで下葉のメタノール中に投じて重合物を析
出させた。これを戸別し、真空乾燥して白色粉体の重合
物76部を得た。The produced polymer was taken from house to house, washed with water, dissolved in chloroform, and then poured into lower leaves of methanol to precipitate the polymer. This was delivered to each house and dried under vacuum to obtain 76 parts of a white powder polymer.
得られたシクロへキシルマレイミド重合体について、ク
ロロホルム中25℃で極限粘度〔1〕を測定したところ
0.374であり、ポリスチレン換算粘度平均分子量は
78000であった。またヨードメトリー法により求め
た活性酸素量は0゜23%であった。従って、分子内に
導入されたペルオキシ基を含む構成昨位の含有割合は、
5.9%であることが判った。また、赤外吸収スペクト
ルを測定した結果、1805■−1と1780an−’
にポリメリックペルオキシドのジアシルペルオキシ基に
よるカルボニル基の吸収が、17QQan−’にはマレ
イミド基のカルボニル基の吸収が認められた。以上から
この重合物は分子内にペルオキシ結合を有するポリシク
ロへキシルマレイミドであることが判った。第1図に得
られた生成物のI[チャートを、また反応条件及び各測
定結果を表1に示す。The intrinsic viscosity [1] of the obtained cyclohexylmaleimide polymer was measured at 25° C. in chloroform and found to be 0.374, and the viscosity average molecular weight in terms of polystyrene was 78,000. The amount of active oxygen determined by iodometry was 0.23%. Therefore, the content ratio of the constituents containing peroxy groups introduced into the molecule is:
It was found to be 5.9%. In addition, as a result of measuring the infrared absorption spectrum, 1805■-1 and 1780an-'
In 17QQan-', absorption of the carbonyl group by the diacylperoxy group of the polymeric peroxide was observed, and absorption of the carbonyl group of the maleimide group was observed in 17QQan-'. From the above, it was found that this polymer was polycyclohexylmaleimide having a peroxy bond in the molecule. FIG. 1 shows the I chart of the obtained product, and Table 1 shows the reaction conditions and measurement results.
犬111し−y
マレイミド化合物、ポリメリックペルオキシドの種類と
量1重合温度及び重合時間を代えた以外は実施例1と同
様にマレイミド系重合体を調製した。条件及び各測定結
果を表1に示す。1. Type and amount of maleimide compound and polymeric peroxide 1 A maleimide polymer was prepared in the same manner as in Example 1, except that the polymerization temperature and time were changed. Table 1 shows the conditions and measurement results.
大差〕−失
温度計、撹拌機および還流冷却器を備えた4つ[]フラ
スコに、ベンジルマレイミド40部。40 parts of benzylmaleimide in 4 flasks equipped with a loss thermometer, a stirrer, and a reflux condenser.
10部およびテトラヒドロフラン300部を仕込み、系
内を窒素ガス置換しながら撹拌下、60℃で3時間反応
させた。重合液を大旦のメタノール中に投じて重合物を
析出させた。次いで炉別して、真空乾燥し、白色の粉体
を32部得た。10 parts and 300 parts of tetrahydrofuran were charged, and the reaction was carried out at 60° C. for 3 hours while stirring and purging the system with nitrogen gas. The polymerization solution was poured into methanol in a large pot to precipitate a polymer. The mixture was then separated in a furnace and dried under vacuum to obtain 32 parts of white powder.
得られたベンジルマレイミド重合体を、クロロホルム中
25℃で、極限粘度〔牝〕を測定したところ、0.22
5であり、ポリスチレン換算粘度平均分子量は4000
0であった。またヨードメトリー法による活性酸素量は
0.44%であった。The intrinsic viscosity (female) of the obtained benzylmaleimide polymer was measured in chloroform at 25°C and found to be 0.22.
5, and the polystyrene equivalent viscosity average molecular weight is 4000
It was 0. The amount of active oxygen determined by iodometry was 0.44%.
赤外吸収スペクトルを測定した結果、1805.178
0(ff−’にポリメリックペルオキシドのジアシル基
のカルボニル基の吸収が、1700an−’にイミド環
のカルボニルの吸収が認められた。以上からこの白色の
重合体は分子内にペルオキシ結合を有するベンジルマレ
イミド重合体であることが解った。As a result of measuring the infrared absorption spectrum, 1805.178
Absorption of the carbonyl group of the diacyl group of the polymeric peroxide was observed at 0(ff-') and absorption of the carbonyl group of the imide ring at 1700an-'. From the above, this white polymer is a benzylmaleimide having a peroxy bond in the molecule. It turned out to be a polymer.
反応条件及び各測定結果を表2に示す。Table 2 shows the reaction conditions and each measurement result.
叉庭仕旦二旦
マレイミド化合物、ポリメリックペルオキシド及び溶媒
の種類と量、重合温度及び重合時間を代えた以外は、実
施例4と同様にマレイミド系重合体の調製を行なった。A maleimide polymer was prepared in the same manner as in Example 4, except that the types and amounts of the maleimide compound, polymeric peroxide, and solvent, polymerization temperature, and polymerization time were changed.
条件及び各測定結果を表2−2q
豊11圀
[シクロへキシルマレイミド−スチレンブロック共重合
体の製造]
温度計、撹拌機、還流冷却器を備えた4つ目フラスコに
0.5%ポリビニルアルコール水溶液300部を仕込み
1次にスチレンモノマー80部に実施例1で製造した分
子内にペルオキシ結合を有するポリシクロへキシルマレ
イミド20部を溶解させた溶液を仕込んだ。反応器内を
窒素ガスで置換させながら撹拌下570℃で8時間重合
反応を行なった。生成した白色粉体を戸別し、水洗した
後真空乾燥を行なった。得られた重合物の重量は88部
であった。Conditions and measurement results are shown in Table 2-2q. Yutaka 11-kuni [Production of cyclohexylmaleimide-styrene block copolymer] 0.5% polyvinyl alcohol was placed in a fourth flask equipped with a thermometer, stirrer, and reflux condenser. 300 parts of an aqueous solution was charged, and then a solution in which 20 parts of the polycyclohexylmaleimide produced in Example 1 and having a peroxy bond in the molecule was dissolved in 80 parts of styrene monomer was charged. The polymerization reaction was carried out at 570° C. for 8 hours while stirring while purging the inside of the reactor with nitrogen gas. The produced white powder was delivered to each house, washed with water, and then vacuum dried. The weight of the obtained polymer was 88 parts.
次いで得られた熱シクロヘキサンで12時間抽出を行い
スチレンの単独重合体を分離し、赤外吸収スペクトルを
測定したところ、1700Ql−”にイミド環のカルボ
ニル基の吸収が、1600dll−’1450(!l−
”にフェニル基の炭素−水素振動の吸収が認められた。Next, the resulting hot cyclohexane was extracted for 12 hours to separate the styrene homopolymer, and the infrared absorption spectrum was measured. As a result, the absorption of the carbonyl group of the imide ring was at 1700Ql-'1450(!l). −
” absorption of carbon-hydrogen vibration of phenyl group was observed.
従って得られた重合物はシクロへキシルマレイミド−ス
チレンブロック共重合体であり、そのブロック効率は抽
出残分か678%であることが判った。Therefore, it was found that the obtained polymer was a cyclohexylmaleimide-styrene block copolymer, and its blocking efficiency was 678% of the extraction residue.
第1図は実施例1で製造した分子内にペルオキシ結合を
有するマレイミド系重合体のJRを示すチャートである
。FIG. 1 is a chart showing the JR of the maleimide polymer having peroxy bonds in the molecule produced in Example 1.
Claims (1)
又はメチル基を示し、R_3は炭素数1〜18の直鎖又
は分枝アルキル基、炭素数3〜12のシクロアルキル基
、炭素数6〜18のアリール基又は置換アリール基を示
す。)で表わされる構成単位90〜99.9重量%と、 次の3種の一般式(II)〜(IV) ▲数式、化学式、表等があります▼・・・(II) (式中R_4は炭素数2〜10のアルキレン基を示し、
R_5は炭素数2〜10のアルキレン基、−CH_2C
H_2OCH_2CH_2−又は−CH_2CH_2O
CH_2CH_2OCH_2CH_2−を示す。)、 ▲数式、化学式、表等があります▼(III) (式中R_6は−C(CH_3)_2CH_2CH_2
C(CH_3)_2−、▲数式、化学式、表等がありま
す▼、 ▲数式、化学式、表等があります▼又は ▲数式、化学式、表等があります▼を示し、 R_7は炭素数2〜10のアルキレン基、シクロヘキシ
レン基又はフェニレン基を示す。)及び▲数式、化学式
、表等があります▼・・・(IV) (式中R_8は、炭素数2〜10のアルキレン基、シク
ロヘキシレン基又はフェニレル基を示し、R_9は−C
(CH_3)_2CH_2CH_2C(CH_3)_2
−、▲数式、化学式、表等があります▼、 ▲数式、化学式、表等があります▼又は ▲数式、化学式、表等があります▼を示す。) から成る群の1種又は2種以上より選択されるペルオキ
シ結合を含む構成単位0.1〜10重量%とからなり、
粘度平均分子量1700〜530000であることを特
徴とする分子内にペルオキシ結合を有するマレイミド系
重合体。[Claims] The following general formula (I) ▲ Numerical formulas, chemical formulas, tables, etc. are included ▼... (I) (In the formula, R_1 and R_2 each represent a hydrogen atom, a halogen atom, or a methyl group, and R_3 is a carbon 90 to 99.9 weight structural units represented by a linear or branched alkyl group having 1 to 18 carbon atoms, a cycloalkyl group having 3 to 12 carbon atoms, an aryl group having 6 to 18 carbon atoms, or a substituted aryl group. % and the following three general formulas (II) to (IV) ▲There are mathematical formulas, chemical formulas, tables, etc.▼...(II) (In the formula, R_4 represents an alkylene group having 2 to 10 carbon atoms,
R_5 is an alkylene group having 2 to 10 carbon atoms, -CH_2C
H_2OCH_2CH_2- or -CH_2CH_2O
CH_2CH_2OCH_2CH_2- is shown. ), ▲There are mathematical formulas, chemical formulas, tables, etc.▼(III) (In the formula, R_6 is -C(CH_3)_2CH_2CH_2
C(CH_3)_2-, ▲There are mathematical formulas, chemical formulas, tables, etc.▼, ▲There are mathematical formulas, chemical formulas, tables, etc.▼ or ▲There are mathematical formulas, chemical formulas, tables, etc.▼, R_7 is a carbon number of 2 to 10 Indicates an alkylene group, a cyclohexylene group, or a phenylene group. ) and ▲Mathematical formulas, chemical formulas, tables, etc.▼...(IV) (In the formula, R_8 represents an alkylene group having 2 to 10 carbon atoms, a cyclohexylene group, or a phenyl group, and R_9 represents -C
(CH_3)_2CH_2CH_2C(CH_3)_2
−, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ or ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼. 0.1 to 10% by weight of a structural unit containing a peroxy bond selected from one or more of the group consisting of
A maleimide polymer having a peroxy bond in the molecule, characterized by having a viscosity average molecular weight of 1,700 to 530,000.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP22423688A JPH0273829A (en) | 1988-09-07 | 1988-09-07 | Maleimide based polymer having peroxy bond in molecule |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP22423688A JPH0273829A (en) | 1988-09-07 | 1988-09-07 | Maleimide based polymer having peroxy bond in molecule |
Publications (1)
Publication Number | Publication Date |
---|---|
JPH0273829A true JPH0273829A (en) | 1990-03-13 |
Family
ID=16810629
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP22423688A Pending JPH0273829A (en) | 1988-09-07 | 1988-09-07 | Maleimide based polymer having peroxy bond in molecule |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPH0273829A (en) |
-
1988
- 1988-09-07 JP JP22423688A patent/JPH0273829A/en active Pending
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