JPH0577699B2 - - Google Patents
Info
- Publication number
- JPH0577699B2 JPH0577699B2 JP9281790A JP9281790A JPH0577699B2 JP H0577699 B2 JPH0577699 B2 JP H0577699B2 JP 9281790 A JP9281790 A JP 9281790A JP 9281790 A JP9281790 A JP 9281790A JP H0577699 B2 JPH0577699 B2 JP H0577699B2
- Authority
- JP
- Japan
- Prior art keywords
- polyglycolide
- weight
- present
- acetone
- film
- 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 - Lifetime
Links
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Polymers OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 claims description 26
- 229920000954 Polyglycolide Polymers 0.000 claims description 22
- 239000000203 mixture Substances 0.000 claims description 17
- 239000000126 substance Substances 0.000 claims description 9
- 229920002451 polyvinyl alcohol Polymers 0.000 claims description 6
- 239000004372 Polyvinyl alcohol Substances 0.000 claims description 5
- 229920002301 cellulose acetate Polymers 0.000 claims description 5
- 229920006238 degradable plastic Polymers 0.000 claims description 5
- 229920000233 poly(alkylene oxides) Polymers 0.000 claims description 5
- 229920000098 polyolefin Polymers 0.000 claims description 4
- 229920000642 polymer Polymers 0.000 description 11
- 229920003023 plastic Polymers 0.000 description 8
- 239000004033 plastic Substances 0.000 description 8
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 5
- 229910002091 carbon monoxide Inorganic materials 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- 239000012778 molding material Substances 0.000 description 5
- 238000010137 moulding (plastic) Methods 0.000 description 5
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 5
- -1 alcohol ester Chemical class 0.000 description 4
- 229920001903 high density polyethylene Polymers 0.000 description 4
- 239000004700 high-density polyethylene Substances 0.000 description 4
- 229920001577 copolymer Polymers 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- 239000004743 Polypropylene Substances 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 229920001155 polypropylene Polymers 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- 229920000915 polyvinyl chloride Polymers 0.000 description 2
- 239000004800 polyvinyl chloride Substances 0.000 description 2
- 238000003856 thermoforming Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-trioxane Chemical compound C1OCOCO1 BGJSXRVXTHVRSN-UHFFFAOYSA-N 0.000 description 1
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 1
- RKDVKSZUMVYZHH-UHFFFAOYSA-N 1,4-dioxane-2,5-dione Chemical compound O=C1COC(=O)CO1 RKDVKSZUMVYZHH-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 229920000704 biodegradable plastic Polymers 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 229920006237 degradable polymer Polymers 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000004088 foaming agent Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 239000011256 inorganic filler Substances 0.000 description 1
- 229910003475 inorganic filler Inorganic materials 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000013502 plastic waste Substances 0.000 description 1
- 229920001083 polybutene Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- FDRCDNZGSXJAFP-UHFFFAOYSA-M sodium chloroacetate Chemical compound [Na+].[O-]C(=O)CCl FDRCDNZGSXJAFP-UHFFFAOYSA-M 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Landscapes
- Compositions Of Macromolecular Compounds (AREA)
Description
【発明の詳細な説明】
（技術分野）
本発明は、分解性プラスチツク組成物に関する
ものである。TECHNICAL FIELD This invention relates to degradable plastic compositions.
（従来技術及びその問題点）
プラスチツクは、日常生活において、フイル
ム、容器等の各種成形品の形で広く使用されてい
る。しかし、プラスチツクの多くは自然環境の中
で分解されないため、プラスチツク使用量の増加
に伴ない、その廃棄物による公害の問題が重視さ
れてきている。このため近年、分解性を有するプ
ラスチツクの開発が広く行われてきている。(Prior Art and its Problems) Plastics are widely used in daily life in the form of various molded products such as films and containers. However, since most plastics do not decompose in the natural environment, as the amount of plastics used increases, the problem of pollution caused by plastic waste is becoming more important. For this reason, in recent years, degradable plastics have been widely developed.
分解性を有する高分子化合物の１つに、ポリグ
リコリドが知られている。このものは、高融点を
有し、耐熱性の点ではすぐれているが、結晶性が
高く、もろいためにプラスチツク材料としては実
用化されていない。 Polyglycolide is known as one of the degradable polymer compounds. Although this material has a high melting point and is excellent in heat resistance, it has not been put to practical use as a plastic material because of its high crystallinity and brittleness.
（発明の課題）
本発明は、分解性を有し、かつプラスチツク成
形材料として実用性あるプラスチツク組成物を提
供することをその課題とする。(Problem of the Invention) An object of the present invention is to provide a plastic composition that is degradable and has practical use as a plastic molding material.
（課題を解決するための手段）
本発明者らは、前記課題を解決すべく鋭意研究
を重ねた結果、ポリグリコリドは、ポリオレフイ
ン、ポリビニルアルコール、ポリアルキレンオキ
シド及び酢酸セルロースの中から選ばれる高分子
物質に対してすぐれたブレンド性能を有すること
を見出すとともに、ポリグリコリドとそれら高分
子物質との溶融混合物はプラスチツク成形材料と
してすぐれた実用性を有することを見出し、本発
明を完成するに至つた。(Means for Solving the Problems) As a result of intensive research to solve the above problems, the present inventors have found that polyglycolide is a polymer selected from polyolefins, polyvinyl alcohols, polyalkylene oxides, and cellulose acetate. The present inventors have discovered that polyglycolide has excellent blending performance with other substances, and that a molten mixture of polyglycolide and these polymeric substances has excellent practicality as a plastic molding material, leading to the completion of the present invention.
即ち、本発明によれば、ポリグリコリド５〜60
重量％と、ポリオレフイン、ポリビニルアルコー
ル、ポリアルキレンオキシド及び酢酸セルロース
の中から選ばれる少なくとも１種の高分子物質95
〜40重量％との溶融混合物からなる分解性プラス
チツク組成物が提供される。 That is, according to the present invention, polyglycolide 5 to 60
% by weight and at least one polymeric substance selected from polyolefin, polyvinyl alcohol, polyalkylene oxide, and cellulose acetate95
A degradable plastic composition is provided comprising a molten mixture of ~40% by weight.
本発明で用いるポリグリコリドは、グリコール
酸又はそのエステルや、クロル酢酸ナトリウムあ
るいはグリコリドを加熱することによつて得られ
る結晶ポリマーである。本発明で用いるポリグリ
コリドを好ましく製造するには、先ず、酸性触媒
の存在下、一酸化炭素とホルムアルデヒドを反応
させてポリグリコリドを生成させ、次にこのポリ
グリコリドに水又は低級アルコールを加えて解重
合反応させてグリコール酸又はその低級アルコー
ルエステルとなし、これを加熱し、重合反応させ
る。この方法によると、安価な原料を用いて高分
子量のポリグリコリドを収率よく得ることができ
るので、工業的に非常に有利である。また、本発
明においては、酸性触媒の存在下で一酸化炭素と
ホルムアルデヒドを反応させて得られる比較的低
分子量のポリグリコリドも使用することが可能で
ある。 The polyglycolide used in the present invention is a crystalline polymer obtained by heating glycolic acid or its ester, sodium chloroacetate, or glycolide. To preferably produce the polyglycolide used in the present invention, first, carbon monoxide and formaldehyde are reacted in the presence of an acidic catalyst to produce polyglycolide, and then water or a lower alcohol is added to the polyglycolide to decompose it. A polymerization reaction is carried out to produce glycolic acid or its lower alcohol ester, which is then heated and subjected to a polymerization reaction. According to this method, high molecular weight polyglycolide can be obtained in good yield using inexpensive raw materials, and therefore it is very advantageous industrially. Further, in the present invention, it is also possible to use a relatively low molecular weight polyglycolide obtained by reacting carbon monoxide and formaldehyde in the presence of an acidic catalyst.
本発明で用いるポリグリコリドとしては、その
数平均分子量が500以上、好ましくは800〜10000
の範囲にあるものが有利に用いられる。 The polyglycolide used in the present invention has a number average molecular weight of 500 or more, preferably 800 to 10,000.
Those within the range are advantageously used.
ポリオレフインとしては、ポリエチレンやポリ
プロピレン、ポリブテン、エチレン／プロピレン
共重合体、エチレン／酢酸ビニル共重合体等のオ
レフインを主体とした従来公知の重合体又は共重
合体が用いられる。ポリビニルアルコールや、ポ
リアルキレンオキシド（ポリエチレンオキシド、
ポリプロピレンオキシド等）、酢酸セルロースは、
市販されているものをそのまま用いることができ
る。本発明においては、他のプラスチツク、例え
ば、ポリ塩化ビニルやポリスチレン等を用いて
も、ブレンド性能が悪く、実用性あるプラスチツ
ク成形材料を得ることはできない。 As the polyolefin, conventionally known polymers or copolymers mainly composed of olefins, such as polyethylene, polypropylene, polybutene, ethylene/propylene copolymer, and ethylene/vinyl acetate copolymer, are used. Polyvinyl alcohol, polyalkylene oxide (polyethylene oxide,
polypropylene oxide, etc.), cellulose acetate,
Commercially available products can be used as they are. In the present invention, even if other plastics such as polyvinyl chloride or polystyrene are used, the blending performance is poor and a practical plastic molding material cannot be obtained.
本発明のプラスチツク組成物は、ポリグリコリ
ドと前記高分子物質を溶融混合することによつて
得られ、この溶融混練物を押出機等の慣用の熱成
形機を用いて所要形状に成形することにより成形
物とすることができる。また、熱成形により得ら
れる成形物は、未発泡体又は発泡体であることが
でき、発泡体を得る場合には、組成物中には発泡
剤を混入する。さらに、組成物には、無機充填剤
や、顔料、酸化防止剤等の慣用の補助添加剤を加
えることができる。 The plastic composition of the present invention is obtained by melt-mixing polyglycolide and the above-mentioned polymeric substance, and by molding this melt-kneaded product into a desired shape using a conventional thermoforming machine such as an extruder. It can be made into a molded product. Furthermore, the molded product obtained by thermoforming can be an unfoamed product or a foamed product, and when a foamed product is obtained, a foaming agent is mixed into the composition. Furthermore, customary auxiliary additives such as inorganic fillers, pigments, antioxidants, etc. can be added to the composition.
ポリグリコリドと他の高分子物質との混合割合
は、ポリグリコリドと高分子物質との合計量に対
し、ポリグリコリド５〜60重量％、好ましくは10
〜50重量％及び高分子物質95〜40重量％、好まし
くは90〜50重量％である。ポリグリコリドの混合
割合が前記範囲より小さくなると、組成物の分解
性が悪くなり、一方、前記範囲より多くなると、
組成物の熱成形性が悪くなるとともに、成形物の
機械的性状が損われるので好ましくない。 The mixing ratio of polyglycolide and other polymeric substances is 5 to 60% by weight, preferably 10% by weight of polyglycolide based on the total amount of polyglycolide and polymeric substances.
~50% by weight and 95-40% by weight of polymeric material, preferably 90-50% by weight. If the mixing ratio of polyglycolide is smaller than the above range, the degradability of the composition will deteriorate; on the other hand, if it is larger than the above range,
This is not preferable because the thermoformability of the composition deteriorates and the mechanical properties of the molded product are impaired.
（発明の効果）
本発明のプラスチツク組成物は、分解性（加水
分解性及び生分解性を含む）を有するポリグリコ
リドを含み、全体的に良好な分解性を有するとと
もに、良好な成形性を有し、分解性プラスチツク
成形材料として好適のものである。また、本発明
により得られる成形物はポリグリコリドに見られ
るようなもろさはなく、強靭性を有するものであ
る。(Effects of the Invention) The plastic composition of the present invention contains polyglycolide that is degradable (including hydrolyzable and biodegradable), and has good overall degradability and good moldability. However, it is suitable as a degradable plastic molding material. Moreover, the molded product obtained by the present invention is not brittle as seen in polyglycolide, and has toughness.
また、本発明の組成物のうち、高分子物質とし
てポリビニルアルコール、ポリアルキレンオキシ
ド又は酢酸セルロースを用いたものは、それら高
分子物質も生分解性を有することから、完全生分
解性プラスチツク成形材料として用いることがで
きる。 Furthermore, among the compositions of the present invention, those using polyvinyl alcohol, polyalkylene oxide, or cellulose acetate as polymeric substances can be used as completely biodegradable plastic molding materials because these polymeric substances are also biodegradable. Can be used.
（実施例）
次に本発明を施例によりさらに詳細に説明す
る。(Example) Next, the present invention will be explained in more detail with reference to Examples.
実施例 １
ステンレス製オートクレーブに、トリオキサン
10.0ｇ、ジクロルメタン30ml及びクロルスルホン
酸４ミリモルを一酸化炭素雰囲気下で仕込み、さ
らに55Kg／cm2になるまで一酸化炭素を圧入した
後、かきまぜながら180℃に昇温し、２時間反応
を行わせた。反応後、未反応の一酸化炭素を放出
し、オートクレーブの内容物をアセトンで洗い出
し、アセトン不溶性重合体（分子量約1200以上の
ポリグリコリド）8.6ｇ、アセトン可溶性重合体
（分子量約1000以下のポリグリコリド）4.3ｇを得
た。Example 1 Trioxane was placed in a stainless steel autoclave.
10.0 g of dichloromethane, 30 ml of dichloromethane, and 4 mmol of chlorosulfonic acid were charged in a carbon monoxide atmosphere, and carbon monoxide was further pressurized until the concentration reached 55 kg/cm 2 .Then, the temperature was raised to 180°C while stirring, and the reaction was carried out for 2 hours. I made it. After the reaction, unreacted carbon monoxide is released, and the contents of the autoclave are washed out with acetone to remove 8.6 g of acetone-insoluble polymer (polyglycolide with a molecular weight of about 1200 or more) and acetone-soluble polymer (polyglycolide with a molecular weight of about 1000 or less). ) 4.3g was obtained.
次にアセトン不溶性重合体0.2ｇと高密度ポリ
エチレン0.8ｇを溶融混合し、150℃、５分、50
Kg／cm2の条件で加圧するとフイルムに成形でき、
このフイルムは充分な柔軟性を有することが確認
された。 Next, 0.2 g of acetone-insoluble polymer and 0.8 g of high-density polyethylene were melt-mixed and heated at 150°C for 5 minutes.
It can be formed into a film by applying pressure under Kg/ cm2 conditions.
It was confirmed that this film had sufficient flexibility.
実施例 ２
実施例１で得られたアセトン不溶性重合体0.5
ｇと高密度ポリエチレン0.5ｇを溶融混合し、150
℃、５分、50Kg／cm2の条件で加圧するとフイルム
に成形でき、このものも充分な柔軟性を有するこ
とがわかつた。Example 2 Acetone-insoluble polymer obtained in Example 1 0.5
g and 0.5 g of high-density polyethylene are melt-mixed,
It was found that by pressurizing at 50 kg/cm 2 at 50° C. for 5 minutes, it could be formed into a film, which also had sufficient flexibility.
また、このフイルムを水中で、100℃、１時間
加熱処理すると、加水分解し、その重量が約20重
量％減少した。 When this film was heated in water at 100°C for 1 hour, it was hydrolyzed and its weight decreased by about 20% by weight.
比較例 １
実施例１の高密度ポリエチレン0.8ｇの代りに、
ポリ塩化ビニルを用いて同様の条件でフイルムの
成形を試みたが、ブレンド物は非常にもろく、フ
イルムには成形できなかつた。Comparative Example 1 Instead of 0.8g of high density polyethylene in Example 1,
An attempt was made to form a film using polyvinyl chloride under similar conditions, but the blend was so brittle that it could not be formed into a film.
実施例 ３
実施例１において、高密度ポリエチレン0.8ｇ
の代りに、ポリプロピレン0.8ｇを用いた以外は
同様にして実験を行つたところ、この場合も柔軟
性あるフイルムを得ることができた。Example 3 In Example 1, 0.8g of high density polyethylene
An experiment was conducted in the same manner except that 0.8 g of polypropylene was used instead, and a flexible film was also obtained in this case.
比較例 ２
施例１において、アセトン不溶性重合体0.5ｇ
とポリスチレン0.5ｇを用いて同様にして実験を
行つたところ、フイルムを得ることができなかつ
た。Comparative Example 2 In Example 1, 0.5 g of acetone-insoluble polymer
When a similar experiment was conducted using 0.5 g of polystyrene, no film could be obtained.
実施例 ４
実施例１において、アセトン不溶性重合体0.5
ｇとポリエチレンオキシド（分子量約20000）0.5
ｇを用いた以外は同様にして溶融混合物を作り、
これを160℃、50Kg／cm2、５分の条件で加圧する
と、柔軟性あるフイルムが得られた。Example 4 In Example 1, acetone-insoluble polymer 0.5
g and polyethylene oxide (molecular weight approximately 20,000) 0.5
A molten mixture was made in the same manner except that g was used,
When this was pressurized at 160° C. and 50 kg/cm 2 for 5 minutes, a flexible film was obtained.
実施例 ５
実施例１において、アセトン不溶性重合体0.5
ｇと、ポリビニルアルコール（分子量：約90000）
0.5ｇを用いた以外は同様にして溶融混合物を作
り、これを130℃、５分、50Kg／cm2の条件で加圧
すると、柔軟性あるフイルムが得られた。Example 5 In Example 1, acetone-insoluble polymer 0.5
g and polyvinyl alcohol (molecular weight: approx. 90,000)
A molten mixture was prepared in the same manner except that 0.5 g was used, and this was pressurized at 130° C. for 5 minutes at 50 Kg/cm 2 to obtain a flexible film.
実施例 ６
実施例１において、アセトン不溶性重合体0.5
ｇと、酢酸セルロース（重合度：約150）0.5ｇを
用いた以外は同様にして実験を行つたところ、こ
の場合にも柔軟性あるフイルムが得られた。Example 6 In Example 1, acetone-insoluble polymer 0.5
An experiment was conducted in the same manner except that 0.5 g of cellulose acetate (degree of polymerization: about 150) was used, and a flexible film was also obtained in this case.
Claims (1)
イン、ポリビニルアルコール、ポリアルキレンオ
キシド及び酢酸セルロースの中から選ばれる少な
くとも１種の高分子物質95〜40重量％との溶融混
合物からなる分解性プラスチツク組成物。1. A degradable plastic composition comprising a molten mixture of 5 to 60% by weight of polyglycolide and 95 to 40% by weight of at least one polymeric substance selected from polyolefin, polyvinyl alcohol, polyalkylene oxide and cellulose acetate.
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9281790A JPH03290451A (en) | 1990-04-06 | 1990-04-06 | Degradable plastic composition |
| US07/668,153 US5227415A (en) | 1990-04-06 | 1991-03-12 | Biodegradable plastic composition |
| EP91302168A EP0450777B1 (en) | 1990-04-06 | 1991-03-14 | Biodegradable plastics composition |
| DE69119966T DE69119966T2 (en) | 1990-04-06 | 1991-03-14 | Biodegradable plastic composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9281790A JPH03290451A (en) | 1990-04-06 | 1990-04-06 | Degradable plastic composition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH03290451A JPH03290451A (en) | 1991-12-20 |
| JPH0577699B2 true JPH0577699B2 (en) | 1993-10-27 |
Family
ID=14064979
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP9281790A Granted JPH03290451A (en) | 1990-04-06 | 1990-04-06 | Degradable plastic composition |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH03290451A (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4492767B2 (en) * | 2000-02-25 | 2010-06-30 | 三菱瓦斯化学株式会社 | Resin composition |
| WO2013134635A1 (en) * | 2012-03-08 | 2013-09-12 | University Of Florida Research Foundation, Inc. | Polyglycolic acid and copolymers thereof from c1 feedstocks |
-
1990
- 1990-04-06 JP JP9281790A patent/JPH03290451A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPH03290451A (en) | 1991-12-20 |
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Legal Events
| Date | Code | Title | Description |
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| EXPY | Cancellation because of completion of term |