JPH0622560B2 - Method for producing hyaluronate sheet - Google Patents
Method for producing hyaluronate sheetInfo
- Publication number
- JPH0622560B2 JPH0622560B2 JP1089683A JP8968389A JPH0622560B2 JP H0622560 B2 JPH0622560 B2 JP H0622560B2 JP 1089683 A JP1089683 A JP 1089683A JP 8968389 A JP8968389 A JP 8968389A JP H0622560 B2 JPH0622560 B2 JP H0622560B2
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- JP
- Japan
- Prior art keywords
- hyaluronate
- sheet
- fibers
- water
- soluble organic
- 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
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- Materials For Medical Uses (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
Description
【発明の詳細な説明】 〔産業上の利用分野〕 本発明はヒアルロン酸塩シート及びその製造方法並びに
その用途に関する。DETAILED DESCRIPTION OF THE INVENTION [Field of Industrial Application] The present invention relates to a hyaluronate sheet, a method for producing the same, and use thereof.
熱傷等の傷痕の成形のためになされた植皮部もしくはそ
のために発生した採皮部等の皮膚欠損傷の治療のため、
従来から被覆保護材が用いられてきた。それらの中で古
くから最も一般的なものは医療用ガーゼもしくは医療用
不織布であるが、これらは創傷部に付着しやすく無理に
剥離すると又傷が付いてしまうという問題点があった。For the treatment of skin damage such as a skin graft part formed for the formation of a scar such as a burn or a skin sampling part generated therefor,
Conventionally, a covering protective material has been used. Among them, medical gauze or medical non-woven fabric has been the most popular from old times, but these have a problem that they tend to adhere to the wound site and are peeled off by force to cause scratches.
そこで、これらの問題点のないより優れた皮膚欠損傷用
被覆保護材を提供すべく、生体適合性の優れた天然物由
来の素材からなる該保護材が開発されている。例えば甲
殻類の外骨格等に含まれているアミノ多糖類の１種であ
るキチンの繊維からなる不織布や、コラーゲン不織布、
或いは凍結豚皮等がそれである。Therefore, in order to provide a more excellent coating protective material for skin deficiency damage that does not have these problems, the protective material made of a natural material-derived material having excellent biocompatibility has been developed. For example, a non-woven fabric composed of fibers of chitin, which is one of the aminopolysaccharides contained in the exoskeleton of crustaceans, collagen non-woven fabric,
Or frozen pig skin or the like.
しかし、これらはいずれも創面への密着性が充分でなく
患部に浸出液が貯留しやすい他、治癒後の皮膚の状態も
よくないという問題点があり、又、資源の面からも充分
な量産が難しいという問題点を抱えていた。However, none of these have sufficient adhesion to the wound surface, the exudate is likely to accumulate in the affected area, and the condition of the skin after healing is not good, and from the viewpoint of resources, sufficient mass production is not possible. I had a problem that it was difficult.
一方、ヒアルロン酸は硝子体、へその緒、皮膚、ニワト
リのトサカ等の動物組織に分布している多糖類であっ
て、近年その特性を利用して化粧品、医薬等に利用され
るようになってきており、特にヒアルロン酸の醗酵法に
よる製法が開発されてからはその用途開発も一段と盛ん
になっているものである。On the other hand, hyaluronic acid is a polysaccharide distributed in the vitreous body, umbilical cord, skin, animal tissues such as chicken mackerel, and in recent years it has come to be used in cosmetics, medicine, etc. by utilizing its characteristics. In particular, since the production method of hyaluronic acid by the fermentation method has been developed, its application development has become more active.
しかしながら、このヒアルロン酸及びその塩そのものを
直接上記の皮膚欠損傷用被覆保護材に用いようとする試
みは今までなかった。ちなみに、これに近い技術として
特開昭61-187866 号公報に医療用ガーゼまたは医療用不
織布にヒアルロン酸又はその塩を0.01〜2.0 重量％にな
るように表面処理することを特徴とする医療用被覆材が
開示されているがこれもヒアルロン酸塩それ自体からな
る創傷被覆保護材ではない。However, there has been no attempt to directly use the hyaluronic acid or its salt itself directly in the above-mentioned protective covering material for skin defect. Incidentally, as a technique similar to this, Japanese Patent Laid-Open No. 61-187866 discloses a medical coating characterized in that a medical gauze or a nonwoven fabric is surface-treated with 0.01 to 2.0% by weight of hyaluronic acid or a salt thereof. Although a material is disclosed, this is also not a wound dressing protector consisting of hyaluronate itself.
本発明は上記した事情に鑑みて、生体適合性があり、皮
膚欠損傷或いは創傷等の人体表面部の患部への密着性に
優れ、保湿性なども良好で、治癒後の表皮の状態もなめ
らかになるような優れた皮膚欠損傷被覆保護材の開発を
目的になされたものである。In view of the above circumstances, the present invention has biocompatibility, excellent adhesion to the affected part of the human body surface part such as skin defect or wound, good moisturizing property, and smooth state of the epidermis after healing. The purpose of the invention is to develop an excellent protective material for skin defect damage such as
本発明者らは以前より研究してきたヒアルロン酸塩が本
来有している保湿性、保水性及び生体への親和性に着目
し、これを利用すると極めて優れた皮膚欠損傷に対する
被覆保護材になり得るという知見を得るとともにヒアル
ロン酸塩のシート化技術を開発し、本発明に到達した。The present inventors have focused their attention on the inherent moisturizing properties, water retaining properties and bioaffinity of hyaluronate, which have been studied for a long time. The present invention has been accomplished by obtaining the knowledge that it can be obtained and developing a sheeting technique for hyaluronate.
すなわち本発明は、ヒアルロン酸塩の繊維からなるシー
トを製造するために水溶性有機溶媒の最終濃度が50 V／
V ％以上になるように該溶媒中にヒアルロン酸水溶液を
導入し、繊維状ヒアルロン酸塩を凝固析出せしめ、次い
で液中で破砕して単繊維にした後、これを抄造し、乾燥
することを特徴とする該シートの製造方法を提供するも
のである。That is, the present invention provides a final concentration of water-soluble organic solvent of 50 V /
Introduce an aqueous solution of hyaluronic acid into the solvent so as to be V% or more to coagulate and precipitate the fibrous hyaluronate, and then crush it in a liquid to form a single fiber, which is then made into paper and dried. The present invention provides a characteristic method for producing the sheet.
以下本発明を詳細に説明する。The present invention will be described in detail below.
ヒアルロン酸は硝子体、へその緒、皮膚、ニワトリのト
サカ等に含まれているグリコサミノグリカンの１種であ
る。Hyaluronic acid is a type of glycosaminoglycan contained in the vitreous, umbilical cord, skin, chicken mackerel and the like.
本発明においてはこのヒアルロン酸塩を原料として用い
る。ヒアルロン酸塩としては好ましくはナトリウム、カ
リウム、カルシウムの塩であり、特に好ましくはナトリ
ウム塩である。In the present invention, this hyaluronate is used as a raw material. The hyaluronic acid salt is preferably a sodium, potassium or calcium salt, and particularly preferably a sodium salt.
ヒアルロン酸塩を製造するには動物組織、例えばニワト
リのトサカ、へその緒などを細砕した後、プロテアーゼ
や溶媒処理によりタンパク質等の不純物を除き、硫酸ア
ンモニウムで分別沈澱を行い製造するか、近年発展した
ヒアルロン酸生産菌を利用した醗酵法により製造するこ
とができる。いずれの方法によるとしても用いるヒアル
ロン酸塩は充分精製し、純度の高いものを用いる必要が
ある。To produce hyaluronate, animal tissues such as chicken mackerel, umbilical cord and the like are crushed, proteins and other impurities are removed by protease or solvent treatment, and then precipitation is performed with ammonium sulfate. It can be produced by a fermentation method using an acid-producing bacterium. Whichever method is used, it is necessary to sufficiently purify the hyaluronate to be used and use a highly pure one.
このヒアルロン酸塩を次に示す方法にて繊維状にする。This hyaluronate is made into a fiber by the following method.
すなわち、まずヒアルロン酸塩、例えばヒアルロン酸ナ
トリウム等を水に溶解し、 0.1〜2.0 W／V ％の水溶液
とする。該ヒアルロン酸塩水溶液の濃度は 0.1W／V ％
未満では粉末化して濾取脱水が困難になるので好ましく
なく、又2.0W／V ％を越えると析出沈澱はするものの内
部流動性のゼリー状となってしまうので好ましくない。That is, first, a hyaluronate, such as sodium hyaluronate, is dissolved in water to form an aqueous solution of 0.1 to 2.0 W / V%. The concentration of the hyaluronate aqueous solution is 0.1 W / V%
If it is less than 2.0 W / V%, it is not preferable because it becomes powdered and the dehydration by filtration becomes difficult, and if it exceeds 2.0 W / V%, it precipitates and precipitates but it becomes a jelly of internal fluidity, which is not preferable.
この水溶液の粘度は0.1W／V ％の時は 200CPであるが、
1.0W／V ％の場合は25,000CPであり、2.0W／V ％のでは
250,000CPというかなり粘調な液となる。The viscosity of this aqueous solution is 200 CP at 0.1 W / V%,
At 1.0W / V% it is 25,000CP, at 2.0W / V%
A viscous liquid of 250,000 CP.
次にこのヒアルロン酸塩水溶液を水溶性有機溶媒の中に
入れると凝固して繊維状となる。該繊維状物の構造はよ
り細いヒアルロン酸塩の繊維が互いに絡み合った構造に
なっている。Then, when this aqueous solution of hyaluronate is put into a water-soluble organic solvent, it is solidified into a fibrous state. The fibrous structure has a structure in which finer hyaluronate fibers are intertwined with each other.
水溶性有機溶媒としてはメタノール、エタノール、アセ
トン、ｎ−プロパノール、イソプロパノール、又はアセ
トニトリルが好ましい。The water-soluble organic solvent is preferably methanol, ethanol, acetone, n-propanol, isopropanol or acetonitrile.
又、水溶性有機溶媒の最終濃度は50 V／V ％以上、好ま
しくは60〜80 V／V ％、特に好ましくは70〜75 V／V ％
である。すなわち、ヒアルロン酸塩水溶液から加わる水
分によって該溶媒の濃度は低下するのであるが、50 V／
V ％以上を保っていないとヒアルロン酸塩が繊維状に析
出してこなくなくなるので好ましくない。The final concentration of the water-soluble organic solvent is 50 V / V% or more, preferably 60 to 80 V / V%, particularly preferably 70 to 75 V / V%.
Is. That is, the concentration of the solvent is lowered by the water added from the hyaluronate aqueous solution,
If V% or more is not maintained, hyaluronate will not be deposited in a fibrous state and will not disappear, which is not preferable.
ヒアルロン酸塩（ドープ）を凝固液である水溶性有機溶
媒中に導入する方法としては容器などから粘調なヒアル
ロン酸塩水溶液を直接水あめ状に自然垂下することによ
り撹拌されている水溶性有機溶媒中に導入する方法もと
ることができるが、工業的にはギヤポンプ等を用いて径
が0.01〜0.5 mm程度のノズルから上記のドープを凝固液
中に吐出せしめて行うのがよい。As a method for introducing the hyaluronate (dope) into the water-soluble organic solvent that is the coagulating liquid, the water-soluble organic solvent that is agitated by naturally hanging a viscous hyaluronate aqueous solution directly from a container or the like into a starch syrup is used. Although it can be introduced into the coagulation solution, it is industrially preferable to discharge the above dope into the coagulating liquid from a nozzle having a diameter of about 0.01 to 0.5 mm using a gear pump or the like.
以上によって得られた繊維状物はそのままではシート化
に適した状態になっていないので、細繊維が絡み合って
太い糸状をなしているものをほぐし、且つ長さもシート
化に適した２〜５mm程度の短繊維にする必要がある。繊
維の長さが上記範囲をはずれて短くなりすぎると綿状に
なりシート化が困難となり、一方長すぎると繊維同志が
分散媒中で塊状化し均一な分散が困難になるので好まし
くない。これに反して上記の２〜５mm程度の長さではシ
ート内の繊維の絡みも適当となり、且つヒアルロン酸塩
繊維の特徴である自己接着性が有効に働いて繊維間の接
着結合も良好となるという効果が得られる。The fibrous material obtained by the above is not in a state suitable for sheeting as it is, so loosen the thick fibers that are entangled with fine fibers, and the length is also suitable for sheeting 2 to 5 mm Need to be short fiber. If the fiber length is out of the above range and becomes too short, it becomes cotton-like and becomes difficult to form into a sheet. On the other hand, if it is too long, the fibers are agglomerated in the dispersion medium and uniform dispersion becomes difficult, which is not preferable. On the contrary, when the length is about 2 to 5 mm, the entanglement of the fibers in the sheet becomes appropriate, and the self-adhesiveness which is a characteristic of hyaluronate fibers works effectively, and the adhesive bond between the fibers becomes good. The effect is obtained.
短繊維化の方法としては公知の短繊維化技術が使用でき
るが、水溶性有機溶媒中で翼付きミキサー例えばカッタ
ーミキサーやジューサーミキサー等を用いて当該繊維状
物を細かく粉砕する方法が簡便である。この場合、該ミ
キサーの回転数としては2000〜5000rpm 程度が好まし
く、時間は10〜30秒程度がよい。又、短繊維化の際、使
用する溶媒は紡糸に使用した前記の水溶性有機溶媒が好
適であり、その濃度は90〜99 V／V ％のものが好まし
い。As a method of shortening the fiber, a known technique of shortening the fiber can be used, but a method of finely pulverizing the fibrous material in a water-soluble organic solvent using a bladed mixer such as a cutter mixer or a juicer mixer is convenient. . In this case, the rotation speed of the mixer is preferably about 2000 to 5000 rpm, and the time is preferably about 10 to 30 seconds. In the case of shortening the fibers, the solvent used is preferably the above-mentioned water-soluble organic solvent used for spinning, and the concentration thereof is preferably 90 to 99 V / V%.
以上によって得られたヒアルロン酸塩の短繊維からシー
トを製造するには和紙の抄造と似た方法によって行うこ
とができる。A sheet similar to the papermaking of Japanese paper can be used to produce a sheet from the hyaluronate short fibers obtained as described above.
すなわち、まず水溶性有機溶媒等の分散液中で当該短繊
維を均一な分散になるように撹拌した後、これを分散液
は通すが該短繊維は通さない固液分離装置、例えば各種
濾材の上に必要量流し込む。この際、厚みが平均的にな
るように流し込むことが好ましく、又吸引濾過の方式を
用いると製造時間を短縮することができる。That is, first, after stirring the short fibers in a dispersion liquid such as a water-soluble organic solvent so as to obtain a uniform dispersion, a solid-liquid separation device that allows the dispersion liquid to pass but does not pass the short fibers, for example, various filter media. Pour the required amount on top. At this time, it is preferable to pour the solution so that the thickness becomes uniform, and if a suction filtration method is used, the manufacturing time can be shortened.
濾材は公知の濾紙、金網、濾布、セラミックもしくはプ
ラスチックフィルター等の中から適宜選択して使用すれ
ばよい。The filter material may be appropriately selected and used from known filter papers, wire nets, filter cloths, ceramics, plastic filters and the like.
又短繊維を分散させておく分散液は、該短繊維を溶解も
しくは変質せしめない溶媒ならいずれも使用できるが、
紡糸及び短繊維化時に使用したのと同じ水溶性有機溶媒
を用いた方が回収再使用の際、経済的であり好ましい。As the dispersion liquid in which the short fibers are dispersed, any solvent which does not dissolve or modify the short fibers can be used.
The use of the same water-soluble organic solvent as that used for spinning and shortening the fibers is economical and preferable for recovery and reuse.
このようにして得られたヒアルロン酸塩繊維シートはい
わゆる湿紙の状態となっている。該シート中に含まれる
水分量は短繊維化時に使用した溶媒が90〜99 V／V ％と
した場合通常 1.0〜11.0V／V ％が好ましく、良好なシ
ートを得るため特に好ましい水分量は５〜６ V／V ％で
ある。The hyaluronate fiber sheet thus obtained is in a so-called wet paper web state. The amount of water contained in the sheet is usually 1.0 to 11.0 V / V% when the solvent used for shortening the fibers is 90 to 99 V / V%, and a particularly preferable amount of water is 5 to obtain a good sheet. ~ 6 V / V%.
この湿紙状シートを通常の乾燥機等を用いて乾燥すると
目的とするシートが得られる。この場合乾燥条件は乾燥
温度が通常50〜90℃、好ましくは60〜80℃、乾燥時間が
30分〜60分である。The target sheet can be obtained by drying the wet paper web-like sheet using an ordinary dryer or the like. In this case, the drying condition is that the drying temperature is usually 50 to 90 ° C, preferably 60 to 80 ° C, and the drying time is
30 to 60 minutes.
本発明のヒアルロン酸塩繊維シートはヒアルロン酸塩繊
維が自己接着性を有するため、一般の不織布で必須の接
着剤を使用しないにもかかわらず、各繊維が互いに接着
結合し、優れた強度を有している。又、このシートはヒ
アルロン酸が天然物由来のものであり上記のように接着
剤の使用もないため、人体に対しては安全であり、優れ
た吸、保水性並びに保湿性とともに生体への適合性も優
れているという効果が得られる。Since the hyaluronate fiber sheet of the present invention has self-adhesiveness, the hyaluronate fibers have excellent strength because each fiber is adhesively bonded to each other even though an essential adhesive is not used in a general nonwoven fabric. is doing. In addition, since hyaluronic acid is derived from a natural product and no adhesive is used as described above, this sheet is safe for the human body and has excellent absorbency, water retention and moisture retention as well as compatibility with living organisms. The effect that it is excellent is obtained.
したがって、これらの効果、特性を利用して本発明シー
トを皮膚欠損傷用被覆保護材として用いた場合、患部か
ら滲み出す液体を素早く吸収、保持して表皮形成を促進
し、治癒後の表皮の状態もなめらかで良好という効果が
得られる。Therefore, when using the sheet of the present invention as a coating protective material for skin deficiency damage by utilizing these effects and characteristics, the liquid exuding from the affected area is quickly absorbed and retained to promote the formation of epidermis, and to promote the formation of epidermis after healing. The effect is that the condition is smooth and good.
以下実施例で本発明を説明する。 The present invention will be described below with reference to examples.
実施例１ ゆっくり撹拌されている95％メタノール1000ml中に粘調
なヒアルロン酸ナトリウムの１ W／V ％水溶液 300mlを
徐々に垂下しつつ導入すると、直ちに凝固して繊維状物
を形成する。この場合のメタノールの最終濃度は約73 V
／V ％であった。Example 1 300 ml of a 1 W / V% aqueous solution of viscous sodium hyaluronate was slowly dropped into 1000 ml of 95% methanol which was slowly stirred, and immediately solidified to form a fibrous substance. The final concentration of methanol in this case is about 73 V
/ V%.
この繊維状物を液体から取り出し、濾別によって充分液
をしぼった後、再び95％メタノール500 ml中に入れ、市
販のジュースミキサーを用い4130rpm で約20秒激しく撹
拌したところ、繊維状物は破砕され、長さ２〜５mmの短
繊維となった。This fibrous material was taken out of the liquid, sufficiently squeezed by filtration, put again in 500 ml of 95% methanol, and vigorously stirred at 4130 rpm for about 20 seconds using a commercially available juice mixer. To be a short fiber having a length of 2 to 5 mm.
続いてこれを適度に撹拌して、該短繊維が均一に分散さ
れた分散液（ドープ）を調製し、吸引濾過装置に設けら
れた直径 150mmの円形濾紙上に流し込むと湿紙様のシー
トが得られた。Then, this is stirred appropriately to prepare a dispersion liquid (dope) in which the short fibers are uniformly dispersed, and when poured into a circular filter paper with a diameter of 150 mm provided in a suction filtration device, a wet paper-like sheet is obtained. Was obtained.
このシートを電熱式乾燥機に入れ60℃で30分間乾燥する
と直径 150mmの円形のヒアルロン酸ナトリウム繊維シー
トが得られた。このシートは白色で濾紙のような外観を
持ち、厚さが約 0.5mmの均一なシートであった。This sheet was placed in an electric heating dryer and dried at 60 ° C. for 30 minutes to obtain a circular sodium hyaluronate fiber sheet having a diameter of 150 mm. This sheet was white and had a filter paper-like appearance, and was a uniform sheet having a thickness of about 0.5 mm.
このシートから 1.5cm2の試験片を切り取り、相対湿度8
1％中に24時間放置した後の重量増加を測定しその吸湿
性を測定したところ18.7％であった。Cut a 1.5 cm 2 test piece from this sheet and
After being left in 1% for 24 hours, the weight increase was measured and the hygroscopicity was 18.7%.
又、巾２mmの帯状試料を切り取り、両端を固定し一端に
おもりを加えて引っ張り、切れたときの荷重量によって
強度を測定したところ41.59 ｇ重の強度があることがわ
かった。Further, a band-shaped sample having a width of 2 mm was cut out, both ends were fixed, a weight was applied to one end and the sample was pulled, and the strength was measured by the load amount at the time of breaking, and it was found that the strength was 41.59 g.
───────────────────────────────────────────────────── フロントページの続き (56)参考文献 特開 平２−14019（ＪＰ，Ａ) ─────────────────────────────────────────────────── ─── Continuation of the front page (56) References JP-A-2-14019 (JP, A)
Claims (4)
上になるように該溶媒中にヒアルロン酸塩水溶液を導入
し、繊維状になったヒアルロン酸塩を凝固析出せしめ、
次いでそれを液中で破砕して短繊維にした後、該繊維を
抄造し、乾燥することを特徴とするヒアルロン酸塩の繊
維からなるシートの製造方法。1. An aqueous hyaluronate solution is introduced into the solvent so that the final concentration of the water-soluble organic solvent is 50 v / v% or more, and the fibrous hyaluronate is coagulated and precipitated.
Then, it is crushed in a liquid to make short fibers, the fibers are made into paper, and dried, and a method for producing a sheet made of hyaluronate fibers.
ル、アセトン、ｎ−プロパノール、イソ−プロパノー
ル、及びアセトニトリルから選ばれた１以上の溶媒であ
ることを特徴とする請求項１記載の製造方法。2. The method according to claim 1, wherein the water-soluble organic solvent is at least one solvent selected from methanol, ethanol, acetone, n-propanol, iso-propanol, and acetonitrile.
ム、ヒアルロン酸カリウム、及びヒアルロン酸カルシウ
ムから選ばれた１種以上である請求項１記載の製造方
法。3. The method according to claim 1, wherein the hyaluronate is one or more selected from sodium hyaluronate, potassium hyaluronate, and calcium hyaluronate.
損傷用被覆保護材。4. A cover protective material for skin defect, which comprises a hyaluronate fiber sheet.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1089683A JPH0622560B2 (en) | 1989-04-11 | 1989-04-11 | Method for producing hyaluronate sheet |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1089683A JPH0622560B2 (en) | 1989-04-11 | 1989-04-11 | Method for producing hyaluronate sheet |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH02268765A JPH02268765A (en) | 1990-11-02 |
| JPH0622560B2 true JPH0622560B2 (en) | 1994-03-30 |
Family
ID=13977566
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1089683A Expired - Lifetime JPH0622560B2 (en) | 1989-04-11 | 1989-04-11 | Method for producing hyaluronate sheet |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0622560B2 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1326883C (en) * | 2005-11-04 | 2007-07-18 | 山东福瑞达生物化工有限公司 | Method for preparing calcium hyauronate |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1254170B (en) * | 1991-12-18 | 1995-09-11 | Mini Ricerca Scient Tecnolog | COMPOSITE MEMBRANES FOR GUIDED REGENERATION OF FABRICS |
| IT1254704B (en) * | 1991-12-18 | 1995-10-09 | Mini Ricerca Scient Tecnolog | NON-WOVEN FABRIC ESSENTIALLY CONSTITUTED FROM DERIVATIVES OF HYALURONIC ACID |
| US5824335A (en) * | 1991-12-18 | 1998-10-20 | Dorigatti; Franco | Non-woven fabric material comprising auto-crosslinked hyaluronic acid derivatives |
| JP3418895B2 (en) * | 1995-11-30 | 2003-06-23 | 株式会社トンボ鉛筆 | Solid adhesive composition |
| CZ302994B6 (en) * | 2010-12-31 | 2012-02-08 | Cpn S.R.O. | Hyaluronic fibers, process of their preparation and use |
| US20210228768A1 (en) * | 2017-07-26 | 2021-07-29 | Youreh Co., Ltd. | Wound dressing comprising hyaluronic acid-calcium and polylysine and manufacturing method therefor |
| KR102338355B1 (en) * | 2021-05-17 | 2021-12-22 | 주식회사 우럭 | Method Of Producing Hyaluronic Acid Non Woven Fabric |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0214019A (en) * | 1988-06-30 | 1990-01-18 | Tonen Corp | Fibrous shaped material and production thereof |
-
1989
- 1989-04-11 JP JP1089683A patent/JPH0622560B2/en not_active Expired - Lifetime
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1326883C (en) * | 2005-11-04 | 2007-07-18 | 山东福瑞达生物化工有限公司 | Method for preparing calcium hyauronate |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH02268765A (en) | 1990-11-02 |
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