JPH03290451A - Degradable plastic composition - Google Patents
Degradable plastic compositionInfo
- Publication number
- JPH03290451A JPH03290451A JP9281790A JP9281790A JPH03290451A JP H03290451 A JPH03290451 A JP H03290451A JP 9281790 A JP9281790 A JP 9281790A JP 9281790 A JP9281790 A JP 9281790A JP H03290451 A JPH03290451 A JP H03290451A
- Authority
- JP
- Japan
- Prior art keywords
- polyglycolide
- plastic composition
- degradable plastic
- present
- weight
- 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.)
- Granted
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 20
- 229920006238 degradable plastic Polymers 0.000 title claims abstract description 7
- 239000000126 substance Substances 0.000 claims abstract description 12
- 229920002301 cellulose acetate Polymers 0.000 claims abstract description 7
- 229920002451 polyvinyl alcohol Polymers 0.000 claims abstract description 7
- 239000004372 Polyvinyl alcohol Substances 0.000 claims abstract description 6
- 229920000233 poly(alkylene oxides) Polymers 0.000 claims abstract description 6
- 229920000098 polyolefin Polymers 0.000 claims abstract description 5
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Polymers OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 claims description 24
- 229920000954 Polyglycolide Polymers 0.000 claims description 20
- 229920000642 polymer Polymers 0.000 abstract description 13
- 238000002156 mixing Methods 0.000 abstract description 6
- 239000000463 material Substances 0.000 abstract description 3
- 230000000593 degrading effect Effects 0.000 abstract 1
- 229920003023 plastic Polymers 0.000 description 8
- 239000004033 plastic Substances 0.000 description 8
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- 239000012778 molding material Substances 0.000 description 5
- 238000010137 moulding (plastic) Methods 0.000 description 5
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 5
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 4
- -1 alcohol ester Chemical class 0.000 description 4
- 229910002091 carbon monoxide Inorganic materials 0.000 description 4
- 229920001903 high density polyethylene Polymers 0.000 description 4
- 239000004700 high-density polyethylene Substances 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 238000003825 pressing 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
- 238000006243 chemical reaction Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000000465 moulding Methods 0.000 description 2
- 238000006116 polymerization reaction Methods 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
- 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
- 230000002378 acidificating effect Effects 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
- 229910002090 carbon oxide Inorganic materials 0.000 description 1
- 239000003054 catalyst 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
- 238000012691 depolymerization reaction Methods 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
- 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
- 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
- 238000003856 thermoforming Methods 0.000 description 1
Abstract
Description
【発明の詳細な説明】
(技術分野)
本発明は、分解性プラスチック組成物に関するものであ
る。DETAILED DESCRIPTION OF THE INVENTION (Technical Field) The present invention relates to a degradable plastic composition.
(従来技術及びその問題点)
プラスチックは、日常生活において、フィルム、容器等
の各種成形量の形で広く使用されている。(Prior art and its problems) Plastics are widely used in daily life in the form of various molded quantities such as films and containers.
しかし、プラスチックの多くは自然環境の中で分解され
ないため、プラスチッ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ックの開発が広く行われ
てきている。However, since most plastics do not decompose in the natural environment, as the amount of plastic 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
ラスチッ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 is not 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、かつプラスチック成形材料と
して実用性あるプラスチッ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、ポリオレフィン、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ック成形
材料としてすぐれた実用性を有することを見出し1本発
明を完成するに至った。(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. In addition to discovering that polyglycolide has excellent blending performance with other substances, they also discovered 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1本発明によれば、ポリグリコリド5〜60重量算
と、ポリオレフィン、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2との溶融混
合物からなる分解性プラスチック組成物が提供される。Namely, according to the present invention, from 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 polyolefins, polyvinyl alcohol, polyalkylene oxide and cellulose acetate. A degradable plastic composition is provided.
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って得られる結晶ポリマーである
0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、酸性触媒ノ存在下、−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1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. In the presence of -carbon oxide and formaldehyde are reacted to produce polyglycolide, then water or a lower alcohol is added to this polyglycolide to cause a depolymerization reaction to produce glycolic acid or its lower alcohol ester, which is heated. 1 Polymerization reaction. According to this method, high molecular weight polyglycolide can be obtained in good yield using inexpensive raw materials, so 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。As the polyglycolide used in the present invention, those having a number average molecular weight of 500 or more, preferably in the range of 800 to 10,000 are advantageously used.
ポリオレフィンとしては、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ィンを主体とした
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0本発明においては、他のプラスチック、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ッ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. Commercially available polyvinyl alcohol, polyalkylene oxide (polyethylene oxide, polypropylene oxide, etc.), and cellulose acetate can be used as they are. In the present invention, other plastics such as
Even if polyvinyl chloride, polystyrene, etc. are used, blending performance is poor and it is impossible to obtain a practical plastic molding material.
本発明のプラスチック組成物は、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って5匈1れ、この
溶融混線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、熟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 prepared by melt-mixing polyglycolide and the above-mentioned polymeric substance, and molding the molten mixture 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 the aged molding may 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2、好ましくは90〜50重
量2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 to 50% by weight of polyglycolide and 95 to 40% by weight of polymeric substances, based on the total amount of polyglycolide and polymeric substances. 2, preferably 90 to 50 weight 2. If the mixing ratio of polyglycolide is smaller than the above range, the degradability of the composition will deteriorate, while if it exceeds the above range, the thermoformability of the composition will deteriorate and the mechanical properties of the molded product will be impaired. Undesirable.
(発明の効果)
本発明の一プラスチック組成物は、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もに、良好な
成形性を有し、分解性プラスチッ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) One plastic composition of the present invention has good moldability in polyglycos having degradability (including hydrolyzability and biodegradability), and is suitable as a degradable plastic molding material. It is. 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ック成形材料と
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) 次に本発明を実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10.0
g、ジクロルメタン3〇−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/
aJ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1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1ooom下のポリグリコリド
)4.3gを得た。Example 1 Trioxane 10.0 was placed in a stainless steel autoclave.
g, 30-g of dichloromethane and 4 mmol of chlorosulfonic acid were charged in a carbon monoxide atmosphere, and further 55 kg/
After one reaction in which carbon monoxide was injected until it reached aJ, the temperature was raised to 180°C while stirring, and the reaction was carried out for 2 hours.
Release unreacted carbon monoxide, wash out the contents of the autoclave with acetone, and remove 8.6 g of acetone-insoluble polymer (polyglycolide with a molecular weight of about 1200 or more) and 4 g of acetone-soluble polymer (polyglycolide with a molecular weight of about 1000 or less). .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、50kg/
aJの条件で加圧するとフィルムに成形でき、このフィ
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 mixed at 150°C for 5 minutes at 50 kg/kg.
It was confirmed that it could be formed into a film by applying pressure under the conditions of aJ, and 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0.5gと高
密度ポリエチレン0.5gを溶融混合し、150℃、5
分、50kg/aJの条件で加圧するとフィルムに成形
でき、このものも充分な柔軟性を有することがわかった
。Example 2 0.5 g of the acetone-insoluble polymer obtained in Example 1 and 0.5 g of high-density polyethylene were melt-mixed and heated at 150°C for 5
It was found that it could be formed into a film by applying pressure under the conditions of 50 kg/aJ and this film also had sufficient flexibility.
また、このフィルムを水中で、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2減少し
た。When this film was heat-treated in water at 100° C. for 1 hour, it was hydrolyzed and its weight decreased by about 20%.
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ィルムの成形を試み
たが、ブレンド物は非常にもろく、フィルムには成形で
きなかった。Comparative Example 1 An attempt was made to form a film under the same conditions using polyvinyl chloride instead of 0.8 g of high-density polyethylene in Example 1, but the blend was extremely brittle and 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
実験を行ったところ、この場合も柔軟性あるフィルムを
得ることができた。Example 3 An experiment was conducted in the same manner as in Example 1 except that 0.8 g of polypropylene was used instead of 0.8 g of high-density polyethylene, and a flexible film was also obtained in this case.
比較例2
実施例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ったと
ころ、フィルムを得ることができなかった。Comparative Example 2 When an experiment was conducted in the same manner as in Example 1 using 0.5 g of the acetone-insoluble polymer and 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0.5gとポ
リエチレンオキシド(分子量約20,000)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1
60℃、50kg/cd、5分の条件で加圧すると、柔
軟性あるフィルムが得られた。Example 4 In Example 1, 0.5 g of acetone-insoluble polymer and 0.5 g of polyethylene oxide (molecular weight approximately 20,000)
A molten mixture was made in the same manner except that 1
A flexible film was obtained by applying pressure at 60° C., 50 kg/cd, and 5 minutes.
実施例5
”’;i゛
−前例1において、アセトン不溶性重合体0.5gと、
ポリビニルアルコール(分子量:約90,000)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/aJの条件で加圧すると
、柔軟性あるフィルムが得られた。Example 5 ``';i'' - In Example 1, 0.5 g of acetone-insoluble polymer and
Polyvinyl alcohol (molecular weight: approximately 90,000) 0.
A molten mixture was prepared in the same manner except that 5 g was used, and this was pressurized at 130° C. for 5 minutes at 50 kg/aJ 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0.5g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ったところ、この場合にも柔
軟性あるフィルムが得られた。Example 6 In Example 1, 0.5 g of acetone-insoluble polymer and
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)
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
性プラスチック組成物。(1) A degradable plastic composition consisting of 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. thing.
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 |
DE69119966T DE69119966T2 (en) | 1990-04-06 | 1991-03-14 | Biodegradable plastic composition |
EP91302168A EP0450777B1 (en) | 1990-04-06 | 1991-03-14 | Biodegradable plastics 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 true JPH03290451A (en) | 1991-12-20 |
JPH0577699B2 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) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2015509555A (en) * | 2012-03-08 | 2015-03-30 | フロリダ大学 リサーチファウンデーション インコーポレイティッド | Polyglycolic acid and its copolymer made from C1 raw material |
-
1990
- 1990-04-06 JP JP9281790A patent/JPH03290451A/en active Granted
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2015509555A (en) * | 2012-03-08 | 2015-03-30 | フロリダ大学 リサーチファウンデーション インコーポレイティッド | Polyglycolic acid and its copolymer made from C1 raw material |
Also Published As
Publication number | Publication date |
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JPH0577699B2 (en) | 1993-10-27 |
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