JPS62223208A - Production of highly heat-resistant vinyl resin - Google Patents
Production of highly heat-resistant vinyl resinInfo
- Publication number
- JPS62223208A JPS62223208A JP6481186A JP6481186A JPS62223208A JP S62223208 A JPS62223208 A JP S62223208A JP 6481186 A JP6481186 A JP 6481186A JP 6481186 A JP6481186 A JP 6481186A JP S62223208 A JPS62223208 A JP S62223208A
- Authority
- JP
- Japan
- Prior art keywords
- vinyl
- parts
- vinyl resin
- resin
- highly heat
- 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
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 title claims abstract description 23
- 229920002554 vinyl polymer Polymers 0.000 title claims abstract description 23
- 229920005989 resin Polymers 0.000 title claims abstract description 20
- 239000011347 resin Substances 0.000 title claims abstract description 20
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- MKRBAPNEJMFMHU-UHFFFAOYSA-N 1-benzylpyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1CC1=CC=CC=C1 MKRBAPNEJMFMHU-UHFFFAOYSA-N 0.000 claims abstract description 13
- 150000001875 compounds Chemical class 0.000 claims abstract description 9
- 239000007870 radical polymerization initiator Substances 0.000 claims abstract description 6
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 abstract description 14
- 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 abstract description 4
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 abstract description 4
- 229920001577 copolymer Polymers 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 9
- 238000000034 method Methods 0.000 description 7
- 238000006116 polymerization reaction Methods 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- HIDBROSJWZYGSZ-UHFFFAOYSA-N 1-phenylpyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1=CC=CC=C1 HIDBROSJWZYGSZ-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- FVQMJJQUGGVLEP-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy 2-ethylhexaneperoxoate Chemical compound CCCCC(CC)C(=O)OOOC(C)(C)C FVQMJJQUGGVLEP-UHFFFAOYSA-N 0.000 description 2
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 2
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 2
- 238000007334 copolymerization reaction Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000010526 radical polymerization reaction 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
- 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
- YIVJZNGAASQVEM-UHFFFAOYSA-N Lauroyl peroxide Chemical compound CCCCCCCCCCCC(=O)OOC(=O)CCCCCCCCCCC YIVJZNGAASQVEM-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- FXPHJTKVWZVEGA-UHFFFAOYSA-N ethenyl hydrogen carbonate Chemical compound OC(=O)OC=C FXPHJTKVWZVEGA-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
- 239000000945 filler Substances 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229920005992 thermoplastic resin Polymers 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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〕
本発明はビニル系樹脂の製造方法く関し、更に詳しくＦ
ｉ高耐熱性ビニル系樹脂の製造方法に関する。[Detailed Description of the Invention] [Industrial Application Field] The present invention relates to a method for producing vinyl resin, and in more detail F.
i It relates to a method for producing a highly heat resistant vinyl resin.
従来より酢酸ビニル樹脂、スチレン樹脂、塩化ビニル樹
脂、メタクリル酸メチル樹脂等のビニル系樹脂が多くの
産業分野で使用されている。これらの樹脂は熱可塑性樹
脂であり、加工性に優れ比較的廉価であるため広く使用
されているが、いずれも耐熱性がｆ分でないため高熱を
受ける部分では使用できないという欠点がある。Vinyl resins such as vinyl acetate resin, styrene resin, vinyl chloride resin, and methyl methacrylate resin have been used in many industrial fields. These resins are thermoplastic resins and are widely used because they have excellent processability and are relatively inexpensive, but they all have the disadvantage that they cannot be used in areas that are exposed to high heat because their heat resistance is not f minutes.
従来から上記の樹脂の耐熱性向上の九めに、α−メチル
スチレンを共重合させる方法がある。Conventionally, the ninth method for improving the heat resistance of the above-mentioned resins is to copolymerize α-methylstyrene.
他ＫＮ−フェニルマレイミドを共重合モノマーとして用
いる方法が耐熱性向上のために提案されている（特公昭
４３−９７５３Ｃ＋）。Another method using KN-phenylmaleimide as a copolymerization monomer has been proposed for improving heat resistance (Japanese Patent Publication No. 43-9753C+).
前記のα−メチルスチレンを共重合させる方法は共重合
性が悪く、必ずしも耐熱性向上効果が充分ではなく、ま
た成形加工性が悪化する等の問題がある。The above method of copolymerizing α-methylstyrene has problems such as poor copolymerizability, not necessarily sufficient effect of improving heat resistance, and deterioration of moldability.
一方、Ｎ−ツエニルマレイミドを共重合させる方法は、
耐熱性は向上するが着色し無色透明な樹脂が得られない
という問題がある。On the other hand, the method of copolymerizing N-twenylmaleimide is
Although the heat resistance is improved, there is a problem in that it is colored and a colorless and transparent resin cannot be obtained.
本発明は高耐熱性であって且つ透明性に優れたビニル系
樹脂の製造方法を提供することを目的としている。An object of the present invention is to provide a method for producing a vinyl resin having high heat resistance and excellent transparency.
本発明は、ビニル系樹脂を製造する際に１ビ二ル系不飽
和化合物５０〜９９重ｆ％とＮ−ベンジルマレイミド１
〜５０重量％とをラジカル重合開始剤の存在下に共重合
させることを特徴とする高耐熱性ビニル系樹脂の製造方
法を提供するものである。The present invention uses 50 to 99 wt % of 1 vinyl unsaturated compound and 1 N-benzylmaleimide when producing vinyl resin.
The present invention provides a method for producing a highly heat-resistant vinyl resin, which is characterized by copolymerizing 50% by weight of the vinyl resin in the presence of a radical polymerization initiator.
本発明に用いるビニル系不飽和化合物としては、例えば
酢１曹ビニル、スチレン、塩化ビニル、メタクリル酸メ
チル、メタクリル酸エチル、アクリル酸メチル、アクリ
ロニトリル等があり、これらは単独で用いるほか２櫨以
上組み合わせて共重合させてもよい。Examples of the vinyl unsaturated compounds used in the present invention include vinyl monocarbonate, styrene, vinyl chloride, methyl methacrylate, ethyl methacrylate, methyl acrylate, and acrylonitrile, which may be used alone or in combination of two or more. It may also be copolymerized.
Ｎ−ベンジルマレイミドＦｉ重合性が高く、上記のビニ
ル系不飽和化合物と容易に共重合するほか、小遣の含有
量で共重合体に耐熱性を付与し、しかも着色性がないた
め無色透明な樹脂が得られる。N-benzylmaleimide Fi has high polymerizability and is easily copolymerized with the above-mentioned vinyl unsaturated compounds. It also imparts heat resistance to the copolymer with a small amount of content, and is colorless and transparent because it has no coloring property. is obtained.
共１合モノマーの仕込比率は、ビニル系不飽和化合物５
０〜９９重址チ好ましくは６０〜９８重１％、！：、Ｎ
−ベンジルマレイミド１〜５０’ｊＪ蝋％好ましくは２
〜４０．Ｔｌｉ盪チである。Ｎ−ベンジルマレイミドの
遺がｌｌｉ遣チ未満では耐熱性の改善効果が発現せず、
また５０１ｉ［４を越えるとビニル系樹脂の本来の優れ
た物性が損なわれる。The charging ratio of co-monomers is 5 vinyl unsaturated compounds.
0-99 weight, preferably 60-98 weight 1%! :,N
- Benzylmaleimide 1 to 50'J wax% preferably 2
~40. It's a good idea. If the residual content of N-benzylmaleimide is less than 100%, the heat resistance improvement effect will not appear.
Moreover, if it exceeds 501i[4, the originally excellent physical properties of the vinyl resin will be impaired.
本発明では上述のモノマー成分をラジカル重合開始剤の
存在下に共重合させる。ラジカル重合開始剤として＋ｉ
過酸化ベンゾイル、ラウロイルペルオ中シト、ｔ−ブチ
ルペルオキシ−２−エチルヘキサノエート、ｔ−ブチル
ペルオキシイソプロビルカーボネート、アゾビスイソブ
チ目ニトリル等等のラジカル重合法により実施すること
ができる。In the present invention, the above monomer components are copolymerized in the presence of a radical polymerization initiator. +i as a radical polymerization initiator
It can be carried out by a radical polymerization method using benzoyl peroxide, lauroyl peroxide, t-butylperoxy-2-ethylhexanoate, t-butylperoxyisopropyl carbonate, azobisisobutylene nitrile, and the like.
共重合は通常３０〜２００℃で１〜２４時間椙時間表う
。Copolymerization is usually carried out at 30 to 200°C for 1 to 24 hours.
なお、本発明においては必要に応じてガラス繊維充填剤
、安定剤等の添加剤を加えることもできる。In addition, in the present invention, additives such as glass fiber fillers and stabilizers may be added as necessary.
本発明の方法によればラジカル重合により容易に共重合
体を得ることができ、その樹脂は耐熱性の向上と共に１
分解温度等によって６１１１定される熱安定性が著しく
向上し、ビニル系樹脂の本来の特徴である透明性を失わ
ず、加工性に変化もなく、脆さの増大等も伴なわないの
で、実用上の価値が大きい。According to the method of the present invention, a copolymer can be easily obtained by radical polymerization, and the resin has improved heat resistance and 1
Thermal stability, which is determined by 6111 depending on the decomposition temperature, etc., has been significantly improved, and the original characteristics of vinyl resins, such as transparency, are not lost, there is no change in processability, and there is no increase in brittleness, so it is suitable for practical use. The value above is great.
以下、実施例および比較例によって本発明を説明する。 The present invention will be explained below with reference to Examples and Comparative Examples.
例中の部及びチは重量基準である。Parts and parts in the examples are based on weight.
実施例１゜
メタクリル酸メチル（ＭＭＡ）９８．７部、Ｎ−ベンジ
ルマレイミド（ＢＺＭＩ）１．３部、アゾビスイソブチ
ロニトリル０．３部およびベンゼン１８０部を重合管に
採取し、これを真空ラインに接続した。その後液体窒素
を用いて重合管を冷却し、真空（Ｉ Ｘ １０−” 〜
２ Ｘ １０−”Ｔｏｒｒ）とじな。その後、乾燥窒素
でＩ Ｔｏｒｒ とした。これらの操作を３回くり返し
たあと重合管を封管した。この重合管を６０℃に保った
恒温槽中で撮り混ぜながら２４時間かけて重合を行なっ
た。重合終了後に開管し、内容物を多量のメタノール中
に投入して重合物を沈澱させた。沈澱を戸別してメタノ
ールでよく洗浄した後、少量のテトラヒドロフランに溶
解させた後、再びメタノール中に投入して沈澱させた。Example 1 98.7 parts of methyl methacrylate (MMA), 1.3 parts of N-benzylmaleimide (BZMI), 0.3 parts of azobisisobutyronitrile and 180 parts of benzene were collected in a polymerization tube, and Connected to vacuum line. Thereafter, the polymerization tube was cooled using liquid nitrogen, and vacuum (I
After that, the pressure was increased to I Torr with dry nitrogen. After repeating these operations three times, the polymerization tube was sealed. This polymerization tube was photographed in a constant temperature bath kept at 60°C. Polymerization was carried out for 24 hours while stirring. After the polymerization was completed, the tube was opened and the contents were poured into a large amount of methanol to precipitate the polymer. After washing the precipitate thoroughly with methanol, it was poured into a small amount of tetrahydrofuran. After dissolving it in water, it was poured into methanol again to precipitate it.
この操作を３回くり返して共重合体を精製した後減圧乾
燥して重合体７２部を得た。得られたものは白色の粉末
であるが、薄板に成形すると無色透明であった。共重合
体粉末を１７０℃にて圧、縮成形し、厚さ３部ｍの試験
片とし、表ＩＫ示す各種の試験を行なった。その結果を
表１に示す。This operation was repeated three times to purify the copolymer, which was then dried under reduced pressure to obtain 72 parts of the polymer. The obtained product was a white powder, but when molded into a thin plate, it was colorless and transparent. The copolymer powder was compressed and compression molded at 170°C to form a test piece with a thickness of 3 parts m, and various tests shown in Table IK were conducted. The results are shown in Table 1.
実施例２〜５
ＢＺＭＩの量を表ＩＫ示すように変えた以外は実施例１
と同様にして共重合体を得た。その結果を表１に示す。Examples 2-5 Example 1 except that the amount of BZMI was changed as shown in Table IK.
A copolymer was obtained in the same manner as above. The results are shown in Table 1.
実施例６〜１０
ビニル系不飽和化合物としてスチレンを用い、ＢＺＭＩ
の量を表２に示すように変えた以外は実施例１と同様に
して共重合体を得た。その結果を表２に示す。Examples 6 to 10 Using styrene as the vinyl unsaturated compound, BZMI
A copolymer was obtained in the same manner as in Example 1 except that the amount of was changed as shown in Table 2. The results are shown in Table 2.
実施例１１
スチレン７０部、アクリロニトリル２０部、ＢＺＭＩＩ
Ｏ部、ｔ−ブチルペルオキシ−２エチルヘキサノエート
１部、ベンゼン１８０部を用いて重合温変７０℃とした
以外は実施ｔｆ’ｌＪ １と同様にして共重合体を得た
。その結果を表２に示す。Example 11 70 parts of styrene, 20 parts of acrylonitrile, BZMII
A copolymer was obtained in the same manner as in Example tf'lJ 1, except that part O, 1 part of t-butylperoxy-2-ethylhexanoate, and 180 parts of benzene were used and the polymerization temperature was changed to 70°C. The results are shown in Table 2.
実施例１２〜工６
ビニル系不飽和化合物として酢僧ビニルを用い、ＢＺＭ
Ｉの２を表３に示すように変えた以外は実施例１と同様
にして共重合体を得た。その結果を表３に示す。Examples 12 to 6 Using vinegar vinyl as the vinyl unsaturated compound, BZM
A copolymer was obtained in the same manner as in Example 1 except that 2 of I was changed as shown in Table 3. The results are shown in Table 3.
比較例１および２ ＢＺＭＩを０部としＭＭＡ １０ （ｌ用イタモ。Comparative examples 1 and 2 BZMI is 0 parts and MMA is 10 (Itamo for l.
を比較例１とし、Ｎ−フェニルマレイミド１０部および
Ｍ Ｍ Ａ ９０部を用いたものを比較例２とし、その
他は実施例１と同様にして重合体または共重合体を得た
。その結果を表ＩＫ示す。Comparative Example 1 was prepared using 10 parts of N-phenylmaleimide and 90 parts of MMA. The results are shown in Table IK.
比較例３および４
Ｂ Ｚ Ｍ Ｉを０部としスチレン１００部を用いたも
のを比較例３とし、Ｎ−フェニルマレイミド１０部およ
びスチレン９０部用いたものを比較例４とし、その他は
実施例工と同１１１Ｋ１．．て重合体または共重合体を
得た。その結果を表２に示す。Comparative Examples 3 and 4 Comparative Example 3 used 0 parts of BZM I and 100 parts of styrene, Comparative Example 4 used 10 parts of N-phenylmaleimide and 90 parts of styrene, and the other examples Same as 111K1. ．． A polymer or copolymer was obtained. The results are shown in Table 2.
比較例５および６
ＢＺＭＩを０部とし酢酸ビニル１００部を用いたものを
比較例５とし、Ｎ−フェニルマレイミド１０部および酢
酸ビニル９０部用いたものを比較例６とし、その他は実
施例１と同様にして重合体または共重合体を得た。その
結果を表３に示す。Comparative Examples 5 and 6 Comparative Example 5 uses 0 parts of BZMI and 100 parts of vinyl acetate, Comparative Example 6 uses 10 parts of N-phenylmaleimide and 90 parts of vinyl acetate, and the rest is the same as Example 1. A polymer or copolymer was obtained in the same manner. The results are shown in Table 3.
以上表１、表２および表３の結果から明らかなように、
本発明の方法により得られたものはいずれも耐熱性の向
上が認められ、透明性も良好である。As is clear from the results in Tables 1, 2, and 3 above,
All of the materials obtained by the method of the present invention have improved heat resistance and good transparency.
Claims (1)
０〜９９重量％とＮ−ベンジルマレイミド１〜５０重量
％とをラジカル重合開始剤の存在下に共重合させること
を特徴とする高耐熱性ビニル系樹脂の製造方法。When producing vinyl resin, vinyl unsaturated compounds 5
A method for producing a highly heat-resistant vinyl resin, which comprises copolymerizing 0 to 99% by weight of N-benzylmaleimide and 1 to 50% by weight in the presence of a radical polymerization initiator.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6481186A JPS62223208A (en) | 1986-03-25 | 1986-03-25 | Production of highly heat-resistant vinyl resin |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6481186A JPS62223208A (en) | 1986-03-25 | 1986-03-25 | Production of highly heat-resistant vinyl resin |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS62223208A true JPS62223208A (en) | 1987-10-01 |
Family
ID=13269000
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP6481186A Pending JPS62223208A (en) | 1986-03-25 | 1986-03-25 | Production of highly heat-resistant vinyl resin |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS62223208A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5073615A (en) * | 1989-03-13 | 1991-12-17 | Continental Polymers, Inc. | High temperature heat resistant acrylics |
| WO1993003076A1 (en) * | 1989-03-13 | 1993-02-18 | Ici Acrylics, Inc. | High temperature heat resistant acrylics |
| US5430115A (en) * | 1988-08-15 | 1995-07-04 | Mitsubishi Rayon Co., Ltd. | Maleimide copolymer and a process for producing the same |
-
1986
- 1986-03-25 JP JP6481186A patent/JPS62223208A/en active Pending
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5430115A (en) * | 1988-08-15 | 1995-07-04 | Mitsubishi Rayon Co., Ltd. | Maleimide copolymer and a process for producing the same |
| US5073615A (en) * | 1989-03-13 | 1991-12-17 | Continental Polymers, Inc. | High temperature heat resistant acrylics |
| WO1993003076A1 (en) * | 1989-03-13 | 1993-02-18 | Ici Acrylics, Inc. | High temperature heat resistant acrylics |
| US5319043A (en) * | 1989-03-13 | 1994-06-07 | Ici Acrylics, Inc. | High temperature heat resistant acrylics method of manufacture |
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