JPH038366B2 - - Google Patents
Info
- Publication number
- JPH038366B2 JPH038366B2 JP16495882A JP16495882A JPH038366B2 JP H038366 B2 JPH038366 B2 JP H038366B2 JP 16495882 A JP16495882 A JP 16495882A JP 16495882 A JP16495882 A JP 16495882A JP H038366 B2 JPH038366 B2 JP H038366B2
- Authority
- JP
- Japan
- Prior art keywords
- copolymer
- present
- methacrylate
- formula
- peroxide
- 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
Links
- 229920001577 copolymer Polymers 0.000 claims description 25
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- PTVDYMGQGCNETM-UHFFFAOYSA-N trityl 2-methylprop-2-enoate Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(OC(=O)C(=C)C)C1=CC=CC=C1 PTVDYMGQGCNETM-UHFFFAOYSA-N 0.000 description 11
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 238000006116 polymerization reaction Methods 0.000 description 9
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 6
- 238000000034 method Methods 0.000 description 5
- 239000000178 monomer Substances 0.000 description 5
- 150000002978 peroxides Chemical class 0.000 description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 229920001002 functional polymer Polymers 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000012778 molding material Substances 0.000 description 3
- 238000010137 moulding (plastic) Methods 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- 230000009102 absorption Effects 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000007334 copolymerization reaction Methods 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 2
- 239000004926 polymethyl methacrylate Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 2
- 238000010526 radical polymerization reaction Methods 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- WMKGMCCZGTXXQU-UHFFFAOYSA-N 2,3-benzodioxine-1,4-dione Chemical compound C1=CC=C2C(=O)OOC(=O)C2=C1 WMKGMCCZGTXXQU-UHFFFAOYSA-N 0.000 description 1
- MKTOIPPVFPJEQO-UHFFFAOYSA-N 4-(3-carboxypropanoylperoxy)-4-oxobutanoic acid Chemical compound OC(=O)CCC(=O)OOC(=O)CCC(O)=O MKTOIPPVFPJEQO-UHFFFAOYSA-N 0.000 description 1
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 1
- KYIKRXIYLAGAKQ-UHFFFAOYSA-N abcn Chemical compound C1CCCCC1(C#N)N=NC1(C#N)CCCCC1 KYIKRXIYLAGAKQ-UHFFFAOYSA-N 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 229910052805 deuterium Inorganic materials 0.000 description 1
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 1
- 238000000578 dry spinning Methods 0.000 description 1
- 238000010894 electron beam technology Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000012760 heat stabilizer Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 229940049920 malate Drugs 0.000 description 1
- -1 malate peroxide Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000006224 matting agent Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 239000011253 protective coating Substances 0.000 description 1
- PQCHENNROHVIHO-UHFFFAOYSA-M silver;2-methylprop-2-enoate Chemical compound [Ag+].CC(=C)C([O-])=O PQCHENNROHVIHO-UHFFFAOYSA-M 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
- JBWKIWSBJXDJDT-UHFFFAOYSA-N triphenylmethyl chloride Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(Cl)C1=CC=CC=C1 JBWKIWSBJXDJDT-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000002166 wet spinning Methods 0.000 description 1
Landscapes
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Description
本発明は、プラスチツク成形材料として、さら
にすぐれた特性を有する機能性高分子材料とし
て、有用な新規なメタクリル酸エステル共重合体
に関する。
すなわち、本発明は、実質的に下記式
The present invention relates to a novel methacrylic acid ester copolymer useful as a plastic molding material and as a functional polymer material having excellent properties. That is, the present invention substantially comprises the following formula
【式】 及び【formula】 as well as
【式】
の反復単位からなり、さらに（）と（）と
は、
（）：（）＝１：99〜60：40
のモル比で存在するとともに、数平均分子量が
1000〜2000000であることを特徴とする、新規な
メタクリル酸エステル共重合体に関する。
本発明の新規メタクリル酸エステル共重合体は
次のようにして製造される。
メタクリル酸メチルとメタクリル酸トリフエニ
ルメチルを通常のラジカル共重合することによつ
て製造されるが、１例を示すと、メタクリル酸メ
チルとメタクリル酸トリフエニルメチルを室温で
９重量倍量のトルエンに溶かし、アゾビスイソブ
チロニトリルを両モノマーに対して１重量％加え
て、60℃に昇温して重合を開始し、24時間重合さ
せる。
この反応物を大量のメタノールに沈澱させ、
過後メタノールで洗浄し、得られた共重合体を真
空乾燥する。
本発明で使用される下記式をIt consists of a repeating unit of [Formula], and () and () exist in a molar ratio of ():()=1:99 to 60:40, and the number average molecular weight is
1,000 to 2,000,000, and relates to a novel methacrylate copolymer. The novel methacrylic acid ester copolymer of the present invention is produced as follows. It is produced by the usual radical copolymerization of methyl methacrylate and triphenylmethyl methacrylate; for example, methyl methacrylate and triphenylmethyl methacrylate are mixed into 9 times the weight of toluene at room temperature. Dissolve the mixture, add 1% by weight of azobisisobutyronitrile to both monomers, raise the temperature to 60°C to start polymerization, and polymerize for 24 hours. This reaction product is precipitated into a large amount of methanol,
After washing with methanol, the obtained copolymer is vacuum dried. The following formula used in the present invention is
【式】
構成するモノマーであるメタクリル酸トリフエニ
ルメチルは従来、公知の方法で製造できる。
即ち、メタクリル酸銀塩と塩化トリフエニルメ
チルをエーテル中で反応させて得られる。（N.A.
Adrova and L.K.Prokhorova、Vysokomol.
Soedin.3、1509（1961）参照）
次に本発明の共重合体の製造法について詳述す
る。
本発明の共重合体の製造法は、実質的にはラジ
カル重合法によるものである。用いられる触媒と
しては、次のようなものである。
アゾビスイソブチロニトリル、アゾビス−２，
４−ジメチルバレロニトリル、アゾビスシクロヘ
キサンカルボニトリルおよびパーオキシド系触媒
として、過酸化水素、ｔ−ブチルパーオクタエー
ト、フタリツクパーオキシド、サクシニツクパー
オキシド、ベンゾイルアセチツクパーオキシド、
ヤシ油酸パーオキシド、ラウリツクパーオキシ
ド、ステアリツクパーオキシド、マレイツクパー
オキシド、ｔ−ブチルヒドロパーオキシド、ジ−
ｔ−ブチルパーオキシド等である。
開始剤は総モノマー重量の0.01〜５重量％用い
ることが好ましい。
重合溶媒は用いることが好ましいが、ラジカル
重合を阻害したり、メタクリル酸トリフエニルメ
チルを溶解しないものであつてはならない。
重合溶媒としては、トルエン、ベンゼン、テト
ラヒドロフラン等が例示できる。重合反応は30℃
〜90℃の範囲でおこなうことが好ましい。
本発明の新規なメタクリル酸エステル共重合体
の共重合比率は次のようである。
すなわち、構成単位（）と構成単位（）の
モル比が、
（）：（）＝１：99〜60：40
好ましくは
（）：（）＝３：97〜50：50
である。
本発明の共重合体の特徴は、有機溶媒、例えば
クロロホルム等に溶解することである。構成単位
（）が60モル％以上ではクロロホルムに不溶と
なる。
又、本発明の共重合体の数平均分子量は1000以
上である。1000以下ではプラスチツク成形材料、
さらには機能性ポリマーとして用いることは困難
である。好ましくは、5000〜1000000である。
本発明の共重合体は、一般に用いられるプラス
チツク成形材料として有用である。
本発明の共重合体は、種々の溶媒、例えば前記
した有機溶媒に容易に溶解するので、この溶液を
用いて種々の成形品、例えばフイルム、繊維、シ
ート等に成形することができる。
例えば、フイルムの成形にはそれ自体周知のキ
ヤステイング法を使用することができ、また、繊
維の成形にはそれ自体周知の乾式紡糸あるいは湿
式紡糸技術を用いることができる。
また、本発明による共重合体は、上述した溶液
の形で各種基質への保護被覆を設けるための塗料
として、あるいは金属基体に対する接着剤等とし
ての利用にも供し得る。
さらに、本発明の共重合体の大きな特徴である
機能性ポリマーとしても有用である。
すなわち、本発明の共重合体は電子線レジスト
用材料として有用に用いられるものである。
なお、本発明の共重合体は、他の共重合可能な
モノマーを１種以上10モル％以下の割合で含有し
ても良い。
本発明の共重合体には、それ自体公知の処方に
従い周知の配合剤、例えば酸化防止剤、熱安定
剤、紫外線吸収剤、着色剤、難燃剤、艶消剤等を
配合してもよい。
次に、本発明について実施例をもつて詳述す
る。
実施例 １
窒素置換したガラス製重合管にメタクリル酸ト
リフエニルメチル（TrMA）0.82ｇ（2.50ｍ
mol）、メタクリル酸メチル（MMA）0.231ｇ
（2.31ｍmol）、トルエン３mlを加えて溶液とす
る。これに重合開始剤アゾビスイソブチロニトリ
ル（AIBN）0.0079ｇを加えた後、重合管を溶封
し、60℃で24時間重合させる。重合混合物を大量
のメタノール中に投じて生成ポリマーを沈澱さ
せ、一夜放置後別し、メタノールで十分洗浄し
た後、乾燥した。ポリマーの収率は0.871ｇ
（82.8％）であつた。
生成ポリマー中のメタクリル酸トリフエニルメ
チル単位の含量は元素分析より43％であつた。ま
た、その数平均分子量はGPC測定により22700で
あつた。この共重合体はクロロホルム、テトラヒ
ドロフランに可溶であるが、アセトニトリルには
溶解しない。一方、メタクリル酸トリフエニルメ
チルの単独重合体はあらゆる有機溶媒に溶解せ
ず、またメタクリル酸メチルの重合体はアセトニ
トリルに溶解する。これらの事実から、こゝに得
られた生成物がメタクリル酸トリフエニルメチル
とメタクリル酸メチルとの共重合体であることは
明らかである。
図１に共重合体の 1H NMRスペクトルをポリ
メタクリル酸メチルのそれと比較して示した。
共重合体のスペクトルはδ＝7.2ppmにフエニ
ルプロトンの吸収が現れて居り、また、α−メチ
ル基プロトン、主鎖メチレンプロトンおよびメト
キシ基プロトンの吸収が共重合体のスペクトルで
は著しく巾広くなり、メタクリル酸トリフエニル
メチル単位が鎖中に導入されていることを示して
いる。これらの重合条件および結果は表１に示し
た。
実施例 ２〜５
実施例１と同様の重合方法で表１に示したモノ
マーを用いて重合し、メタクリル酸メチル共重合
体を得た。[Formula] Triphenylmethyl methacrylate, which is a constituent monomer, can be produced by a conventionally known method. That is, it is obtained by reacting silver methacrylate and triphenylmethyl chloride in ether. (NA
Adrova and LKProkhorova, Vysokomol.
(See Soedin. 3, 1509 (1961)) Next, the method for producing the copolymer of the present invention will be described in detail. The method for producing the copolymer of the present invention is substantially based on a radical polymerization method. The catalyst used is as follows. Azobisisobutyronitrile, azobis-2,
4-dimethylvaleronitrile, azobiscyclohexanecarbonitrile and peroxide catalysts such as hydrogen peroxide, t-butyl peroctaate, phthalic peroxide, succinic peroxide, benzoylacetic peroxide,
Coco acid peroxide, laurick peroxide, stearic peroxide, malate peroxide, t-butyl hydroperoxide, di-
t-butyl peroxide and the like. The initiator is preferably used in an amount of 0.01 to 5% by weight based on the total monomer weight. It is preferable to use a polymerization solvent, but it must not inhibit radical polymerization or not dissolve triphenylmethyl methacrylate. Examples of the polymerization solvent include toluene, benzene, and tetrahydrofuran. Polymerization reaction at 30℃
It is preferable to carry out the heating in the range of ~90°C. The copolymerization ratio of the novel methacrylic acid ester copolymer of the present invention is as follows. That is, the molar ratio of the structural unit () to the structural unit () is ():()=1:99 to 60:40, preferably ():()=3:97 to 50:50. A feature of the copolymer of the present invention is that it is soluble in organic solvents such as chloroform. If the structural unit () is 60 mol% or more, it becomes insoluble in chloroform. Further, the number average molecular weight of the copolymer of the present invention is 1000 or more. Below 1000, plastic molding materials,
Furthermore, it is difficult to use it as a functional polymer. Preferably, it is 5,000 to 1,000,000. The copolymers of this invention are useful as commonly used plastic molding materials. Since the copolymer of the present invention is easily dissolved in various solvents, such as the above-mentioned organic solvents, this solution can be used to form various molded products, such as films, fibers, sheets, etc. For example, casting methods known per se may be used to form the film, and dry spinning or wet spinning techniques known per se may be used to form the fibers. The copolymer according to the invention can also be used in the form of a solution as described above, as a paint for providing a protective coating on various substrates, or as an adhesive for metal substrates. Furthermore, it is useful as a functional polymer, which is a major feature of the copolymer of the present invention. That is, the copolymer of the present invention can be usefully used as a material for electron beam resist. In addition, the copolymer of the present invention may contain one or more types of other copolymerizable monomers in a proportion of 10 mol% or less. The copolymer of the present invention may be blended with well-known compounding agents such as antioxidants, heat stabilizers, ultraviolet absorbers, colorants, flame retardants, matting agents, etc. according to known formulations. Next, the present invention will be described in detail with reference to examples. Example 1 0.82 g (2.50 m) of triphenylmethyl methacrylate (TrMA) was placed in a glass polymerization tube purged with nitrogen.
mol), methyl methacrylate (MMA) 0.231g
(2.31 mmol) and 3 ml of toluene to make a solution. After adding 0.0079 g of a polymerization initiator azobisisobutyronitrile (AIBN) to this, the polymerization tube was melt-sealed and polymerized at 60° C. for 24 hours. The polymerization mixture was poured into a large amount of methanol to precipitate the produced polymer, which was left to stand overnight, separated, thoroughly washed with methanol, and then dried. Polymer yield is 0.871g
(82.8%). The content of triphenylmethyl methacrylate units in the produced polymer was found to be 43% by elemental analysis. Moreover, its number average molecular weight was 22,700 by GPC measurement. This copolymer is soluble in chloroform and tetrahydrofuran, but not in acetonitrile. On the other hand, a homopolymer of triphenylmethyl methacrylate is not soluble in any organic solvent, and a polymer of methyl methacrylate is soluble in acetonitrile. From these facts, it is clear that the product thus obtained is a copolymer of triphenylmethyl methacrylate and methyl methacrylate. Figure 1 shows the 1 H NMR spectrum of the copolymer in comparison with that of polymethyl methacrylate. In the spectrum of the copolymer, the absorption of phenyl protons appears at δ = 7.2 ppm, and the absorptions of α-methyl group protons, main chain methylene protons, and methoxy group protons become significantly broader in the spectrum of the copolymer. , indicating that triphenylmethyl methacrylate units have been introduced into the chain. These polymerization conditions and results are shown in Table 1. Examples 2 to 5 The monomers shown in Table 1 were polymerized using the same polymerization method as in Example 1 to obtain methyl methacrylate copolymers.
図−１Ａおよび図−１Ｂは、それぞれ本発明の
共重合体であるメタクリル酸メチルとメタクリル
酸トリフエニルメチルとの共重合体とポリメタク
リル酸メチルの 1H NMRスペクトル（重クロロ
ホルム溶液、55℃、100MHz）である。
Figures 1A and 1B show 1 H NMR spectra of the copolymer of methyl methacrylate and triphenylmethyl methacrylate and polymethyl methacrylate, respectively, which are copolymers of the present invention (deuterium chloroform solution, 55°C, 100MHz).
Claims (1)
と 【式】 99〜40モル％の式（）で示される構造単位 【式】 とからなる数平均分子量1000〜2000000の新規な
メタクリル酸エステル共重合体。[Claims] 1 A number average molecular weight of 1000 to 1000, consisting of 1 to 60 mol% of the structural unit represented by the formula () and [Formula] 99 to 40 mol% of the structural unit [formula] represented by the formula () 2,000,000 new methacrylic acid ester copolymers.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP16495882A JPS5956414A (en) | 1982-09-24 | 1982-09-24 | Novel methacrylate copolymer |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP16495882A JPS5956414A (en) | 1982-09-24 | 1982-09-24 | Novel methacrylate copolymer |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5956414A JPS5956414A (en) | 1984-03-31 |
| JPH038366B2 true JPH038366B2 (en) | 1991-02-05 |
Family
ID=15803090
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP16495882A Granted JPS5956414A (en) | 1982-09-24 | 1982-09-24 | Novel methacrylate copolymer |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5956414A (en) |
-
1982
- 1982-09-24 JP JP16495882A patent/JPS5956414A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5956414A (en) | 1984-03-31 |
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