KR20190036227A - Preparation Method of Sodium Hyaluronate Film by Automatic Control Coater and Sodium Hyaluronate Film prepared Thereof - Google Patents

Preparation Method of Sodium Hyaluronate Film by Automatic Control Coater and Sodium Hyaluronate Film prepared Thereof Download PDF

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KR20190036227A
KR20190036227A KR1020170125213A KR20170125213A KR20190036227A KR 20190036227 A KR20190036227 A KR 20190036227A KR 1020170125213 A KR1020170125213 A KR 1020170125213A KR 20170125213 A KR20170125213 A KR 20170125213A KR 20190036227 A KR20190036227 A KR 20190036227A
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film
hyaluronate
solution
thickness
present
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KR102030496B1 (en
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권동건
홍주연
방지현
만 하
이영모
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(주)진우바이오
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Priority to KR1020170125213A priority Critical patent/KR102030496B1/en
Priority to PCT/KR2017/015633 priority patent/WO2018164358A1/en
Priority to US16/491,054 priority patent/US11298855B2/en
Priority to PCT/KR2018/002727 priority patent/WO2018164489A1/en
Priority to EP18764078.4A priority patent/EP3593973A4/en
Priority to JP2019547634A priority patent/JP6985402B2/en
Priority to CN201880016376.8A priority patent/CN110382193B/en
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    • BPERFORMING OPERATIONS; TRANSPORTING
    • B29WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29CSHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
    • B29C39/00Shaping by casting, i.e. introducing the moulding material into a mould or between confining surfaces without significant moulding pressure; Apparatus therefor
    • B29C39/003Shaping by casting, i.e. introducing the moulding material into a mould or between confining surfaces without significant moulding pressure; Apparatus therefor characterised by the choice of material
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61LMETHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L27/00Materials for grafts or prostheses or for coating grafts or prostheses
    • A61L27/14Macromolecular materials
    • A61L27/20Polysaccharides
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61LMETHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L27/00Materials for grafts or prostheses or for coating grafts or prostheses
    • A61L27/50Materials characterised by their function or physical properties, e.g. injectable or lubricating compositions, shape-memory materials, surface modified materials
    • A61L27/60Materials for use in artificial skin
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61LMETHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L31/00Materials for other surgical articles, e.g. stents, stent-grafts, shunts, surgical drapes, guide wires, materials for adhesion prevention, occluding devices, surgical gloves, tissue fixation devices
    • A61L31/04Macromolecular materials
    • A61L31/042Polysaccharides
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B29WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29CSHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
    • B29C39/00Shaping by casting, i.e. introducing the moulding material into a mould or between confining surfaces without significant moulding pressure; Apparatus therefor
    • B29C39/02Shaping by casting, i.e. introducing the moulding material into a mould or between confining surfaces without significant moulding pressure; Apparatus therefor for making articles of definite length, i.e. discrete articles
    • B29C39/04Shaping by casting, i.e. introducing the moulding material into a mould or between confining surfaces without significant moulding pressure; Apparatus therefor for making articles of definite length, i.e. discrete articles using movable moulds not applied
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08LCOMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L5/00Compositions of polysaccharides or of their derivatives not provided for in groups C08L1/00 or C08L3/00
    • C08L5/08Chitin; Chondroitin sulfate; Hyaluronic acid; Derivatives thereof
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61LMETHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L2430/00Materials or treatment for tissue regeneration
    • A61L2430/34Materials or treatment for tissue regeneration for soft tissue reconstruction
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B29WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29KINDEXING SCHEME ASSOCIATED WITH SUBCLASSES B29B, B29C OR B29D, RELATING TO MOULDING MATERIALS OR TO MATERIALS FOR MOULDS, REINFORCEMENTS, FILLERS OR PREFORMED PARTS, e.g. INSERTS
    • B29K2005/00Use of polysaccharides or derivatives as moulding material

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Public Health (AREA)
  • Epidemiology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Transplantation (AREA)
  • Oral & Maxillofacial Surgery (AREA)
  • Dermatology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Surgery (AREA)
  • Vascular Medicine (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Cosmetics (AREA)
  • Medicinal Preparation (AREA)
  • Polysaccharides And Polysaccharide Derivatives (AREA)
  • Materials For Medical Uses (AREA)

Abstract

The present invention relates to a method of producing a hyaluronate film and a hyaluronate film produced thereby and, more specifically, to a method of producing a hyaluronate film, which enables a large-batch production using an automatic applicator, and a hyaluronate film which may be used as a mask pack, a patch, a film-type adhesion barrier, and the like. In particular, the method of producing a hyaluronate film comprises the steps of: (a) dissolving hyaluronate in a solvent, thereby forming a hyaluronate solution of 0.1-30.0 wt%; (b) injecting the formed hyaluronate solution into an automatic applicator and casting a film in a thickness of 0.025-5mm; and (c) drying the cast film at 30-50°C. According to the present invention, the method of producing a hyaluronate film by using an automatic applicator enables a convenient large-batch production, and can conveniently adjust properties through controlling viscosity of the hyaluronate and thickness of the film. The hyaluronate film thus produced may be used for cosmetics, drugs, packs for medical devices, patches, artificial skin, adhesion barriers, and so forth.

Description

자동 도포기에 의한 히알루론산염 필름의 제조방법 및 이로부터 제조된 히알루론산염 필름 {Preparation Method of Sodium Hyaluronate Film by Automatic Control Coater and Sodium Hyaluronate Film prepared Thereof}A method of producing a hyaluronate film by an automatic applicator and a hyaluronate film prepared therefrom (Preparation Method of Sodium Hyaluronate Film by Automatic Control Coater and Sodium Hyaluronate Film Prepared Thereof)

본 발명은 히알루론산염 필름의 제조방법 및 이로부터 제조된 히알루론산염 필름에 관한 것으로, 더욱 상세하게는 대량 생산이 용이한 자동 도포기에 의한 히알루론산염 필름의 제조방법과 마스크 팩, 패치, 필름형 유착방지제 등으로 활용 가능한 히알루론산염 필름에 관한 것이다.The present invention relates to a process for producing a hyaluronate film and a hyaluronate film produced therefrom, and more particularly to a process for producing a hyaluronate film by an automatic dispenser which is easy to mass- And a hyaluronate film usable as an anti-adhesion agent.

필름 제품을 대량으로 제품화하기 위해서는 균일하고, 재현성 있게 필름의 두께를 손쉽게 조절할 수 있는 것이 필수적이다. 특히 용액 상태에서 필름 제조 시 작업자 간의 숙련도의 차이가 발생하기 때문에 자동화 방법이 권장되는데, 자동 도포기 (Automatic Control Coater)를 이용한 필름 캐스팅 (Casting) 방법이 이러한 문제를 해결하는데 도움이 된다. 자동 도포기는 필름 제조 시 일정한 속도로 캐스팅하며 시료에 적용된 압력, 평탄도 등을 동일한 조건으로 제공한다는 장점이 있다. 두께 조절이 용이한 자동 도포기를 사용 시, 제품의 사용 용도에 따라 필름의 두께 조절을 통해 재현성 있는 균일한 필름 제품을 대량 생산할 수 있다.In order to mass-produce a film product, it is essential that the thickness of the film can be easily controlled in a uniform and reproducible manner. In particular, automation methods are recommended because of differences in skill between workers in film production in solution. Film casting using automatic control coater helps solve these problems. The automatic dispenser is advantageous in that the film is cast at a constant speed in the production of the film, and the pressure and flatness applied to the sample are provided under the same conditions. When using an automatic applicator with easy thickness control, it is possible to mass-produce reproducible and uniform film products by controlling the thickness of the film according to the use purpose of the product.

한편, 관절 낭액 (Synovial Fluid)과 세포외 기질 (Extracellular Matrix)에 주로 존재하는 생체 물질인 히알루론산염(Sodium Hyaluronate, Hyaluronic Acid)은 선형의 고분자 천연 다당체 (Polysaccharide)이다. 인체 결합조직, 상피 및 신경조직 등에 고루 분포되어있는 히알루론산염은 높은 생체적합성을 갖는 안전한 재료로서 수분을 다량 함유할 수 있고 우수한 점탄성을 지니고 있어 퇴행성 관절염 치료제, 점안제, 안과수술보조제 등의 의약품과 주름 개선 관련 필러와 조직 수복용 유착 방지제 등의 의료기기, 보습과 주름 개선 등의 항노화 소재로서 화장품과 식품 등 여러 분야에 걸쳐 널리 응용되고 있다. Meanwhile, Sodium Hyaluronate (Hyaluronic Acid), a biomaterial mainly present in synovial fluid and extracellular matrix, is a linear polymeric polysaccharide. Hyaluronate, which is widely distributed in human connective tissues, epithelium and nervous tissues, is a safe material with high biocompatibility. It can contain a large amount of water and has excellent viscoelasticity. Therefore, it can be used as a medicine for degenerative arthritis, eye drops, Anti-aging materials such as wrinkle-improving fillers, medical devices such as anti-adhesion agents for tissue repair, and moisturizing and wrinkle-improving materials are widely used in various fields such as cosmetics and foods.

그러나 우수한 생체 적합성으로 인해 공기 중에 노출되어 수분 이입 시 미생물 등에 의해 쉽게 오염되어 제품이 변형됨으로써 사용이 불가능해지는 문제점이 있으므로 사용 시 큰 주의가 요구된다. However, due to its excellent biocompatibility, it is exposed to the air and is easily contaminated by microorganisms and the like when the water is introduced.

시중에 유통되고 있는 화장품, 관절 주사제, 필러 등의 모든 히알루론산염 제품은 수용액 상태로서 미생물 오염 등의 염려가 매우 커서 화장품의 경우 독성의 방부제를 과량 사용하거나 의약품과 의료기기의 경우 무균 설비 하에서 생산하여야 하므로 생산의 어려움은 물론 최종 제품의 보관, 유통 및 사용에 매우 주의를 요구한다. All hyaluronate products such as cosmetics, joint injections, fillers, etc., which are on the market, are in a state of aqueous solution, so there is a great concern about microbial contamination. Therefore, cosmetic products are used in excess of toxic preservatives or in the case of pharmaceuticals and medical devices under sterile conditions It requires great attention to the storage, distribution and use of end products as well as difficulties in production.

본 발명자들은 히알루론산염 제품을 수분이 최소화된 봉합사 (Suture Fiber) 또는 필름 형태로 제조하게 되면 미생물 오염 등에 대해 높은 저항성을 가지게 됨을 확인하였으며(한국등록특허 제1709608호, 한국출원특허 제2017-0029094호), 이를 통해 액상이 아닌 고체형의 히알루론산 제품의 경우 생산 관리와 보관이 용이하여 생산자 및 사용자는 물론 시술자에게도 매우 편리한 장점이 있음을 확인할 수 있었다.The present inventors have found that when a hyaluronic acid salt product is manufactured into a suture fiber or a film having a minimum moisture content, it has a high resistance to microbial contamination (Korean Patent No. 1709608, Korean Patent Application No. 2017-0029094 Hyaluronic acid products, which are solid rather than liquid, can be easily managed for production and storage, which is convenient for producers and users as well as for practitioners.

히알루론산염 필름에 대한 연구는 본 발명자가 100% 히알루론산염을 용매 캐스팅 (Solvent Casting) 방법으로 필름을 제조한 특허(출원번호: 제2017-0029094호)를 제외하고는 전무한 상황이다. 하지만, 용매 캐스팅 방법을 이용할 경우에는 히알루론산염을 고농도로 함유하며, 균일한 외관과 물성을 갖는 히알루론산염 필름을 대량 생산이 곤란하다는 문제점이 있다.Studies on hyaluronate films have been limited by the inventors of the present invention except for a patent (Application No .: No. 2017-0029094) in which a film was manufactured by a solvent casting method of 100% hyaluronate. However, when a solvent casting method is used, there is a problem that it is difficult to mass-produce a hyaluronate film containing a hyaluronate at a high concentration and having uniform appearance and physical properties.

이에, 본 발명자들은 상기 문제점을 해결하기 위하여 노력한 결과, 히알루론산염 용액을 자동 도포기로 캐스팅 후 건조시킬 경우, 다양한 두께의 히알루론산염 필름을 균일하게 대량으로 제조할 수 있고, 히알루론산염 용액의 점도와 두께 조절을 통하여 물성 조절이 가능하다는 것을 확인하고, 본 발명을 완성하게 되었다. The present inventors have made efforts to solve the above problems. As a result, the present inventors have found that when casting a hyaluronate solution into an automatic coater and then drying it, a hyaluronate film having various thicknesses can be uniformly mass- It is confirmed that the physical properties can be controlled by controlling the viscosity and the thickness, and the present invention has been completed.

본 발명의 목적은 생체 적합성과 항 노화 기능을 지녀 다양한 분야에서 활용되고 있는 히알루론산염 필름의 제조 방법을 제공하는데 있다.It is an object of the present invention to provide a method for producing a hyaluronate film having biocompatibility and anti-aging function and being utilized in various fields.

본 발명의 다른 목적은 히알루론산염을 고농도로 함유하고, 표면이 균일한 히알루론산염 필름 및 이를 대량으로 생산하는 방법을 제공하는데 있다.Another object of the present invention is to provide a hyaluronate film containing a high concentration of hyaluronate and having uniform surface and a method of mass-producing the hyaluronate film.

본 발명의 또 다른 목적은 미생물에 대한 저항성과 우수한 기계적 물성을 갖는 히알루론산염 필름을 포함하는 마스크 팩, 패치, 의료기기용 인공 피부와 유착 방지제를 제공하는데 있다.It is still another object of the present invention to provide a mask pack, a patch, and an artificial skin and an anti-adhesion agent comprising a hyaluronate film having resistance to microorganisms and excellent mechanical properties.

상기 목적을 달성하기 위하여, 본 발명은 (a) 히알루론산염을 용매로 용해시켜 0.1~30.0중량%의 히알루론산염 용액을 제조하는 단계; (b) 상기 제조된 히알루론산염 용액을 자동 도포기에 주입하고, 0.025~5㎜의 두께로 필름을 캐스팅하는 단계; 및 (c) 캐스팅 된 필름을 30~50℃ 조건에서 건조시키는 단계를 포함하는 자동 도포기에 의한 히알루론산염 필름의 제조방법을 제공한다.In order to accomplish the above object, the present invention provides a method for producing a hyaluronate, comprising: (a) dissolving a hyaluronate in a solvent to prepare a 0.1 to 30.0 wt% hyaluronate solution; (b) casting the prepared hyaluronate solution into an automatic coater and casting the film to a thickness of 0.025 to 5 mm; And (c) drying the cast film at 30 to 50 ° C.

본 발명에 있어서, 상기 히알루론산염 용액의 점도는 300~100,000cPs 인 것을 특징으로 한다.In the present invention, the viscosity of the hyaluronate solution is 300 to 100,000 cPs.

본 발명은 또한, 상기 방법으로 제조된 히알루론산염 필름을 제공한다.The present invention also provides a hyaluronate film produced by the above method.

본 발명에 있어서, 상기 히알루론산염 필름은 인장 강도 50~300MPa인 것을 특징으로 한다.In the present invention, the hyaluronate film has a tensile strength of 50 to 300 MPa.

본 발명은 또한, 상기 히알루론산염 필름을 포함하는 마스크 팩, 패치, 인공피부 및 유착 방지제를 제공한다.The present invention also provides a mask pack, patch, artificial skin and an anti-adhesion agent comprising the hyaluronate film.

본 발명의 자동 도포기에 의한 히알루론산염 필름의 제조방법은 대량 생산이 용이하고, 히알루론산염의 점도 및 필름의 두께 조절을 통해 물성을 쉽게 조절할 수 있으며, 이를 통하여 제조된 히알루론산염 필름은 화장품, 의약품, 의료기기용 팩, 패치, 인공 피부, 유착 방지제 등의 용도로 적용이 가능하다.The method of producing a hyaluronate film by the automatic dispenser of the present invention is easy to mass-produce, and the physical properties can be easily controlled by controlling the viscosity of the hyaluronic acid salt and the thickness of the film. The hyaluronate film thus prepared can be used for cosmetics, It can be applied to medicines, packs for medical devices, patches, artificial skin, and anti-adhesion agents.

도 1은 통상적인 자동 도포기의 설명도이다.
도 2는 히알루론산염의 점도에 따라 제조된 히알루론산염 필름의 사진이다.
도 3은 건조방식에 따라 제조된 히알루론산염 필름의 사진이다.
도 4는 본 발명의 일 실시예에 따라 제조된 히알루론산염 필름의 사진이다.
1 is an explanatory diagram of a conventional automatic dispenser.
2 is a photograph of a hyaluronate film prepared according to the viscosity of a hyaluronic acid salt.
3 is a photograph of a hyaluronate film produced according to the drying method.
4 is a photograph of a hyaluronate film produced according to an embodiment of the present invention.

본 발명에서는 히알루론산염 용액을 자동 도포기에 주입하고 건조시킬 경우, 다양한 두께의 히알루론산염 필름을 균일하게 대량으로 제조할 수 있고, 히알루론산염 용액의 점도와 두께 조절을 통하여 물성 조절이 가능하다는 것을 확인하고자 하였다. In the present invention, when a hyaluronate solution is injected into an automatic applicator and dried, it is possible to uniformly mass-produce hyaluronate films of various thicknesses and to control the physical properties through controlling the viscosity and thickness of the hyaluronate solution Respectively.

본 발명에서는 물 또는 에탄올 수용액으로 히알루론산염을 용해시켜, 0.1~30.0중량%의 히알루론산염 용액을 제조하고, 자동 도포기에 주입시키고, 다양한 두께로 캐스팅 후 30~50℃ 조건에서 건조시켜 히알루론산염 필름을 제조하였다. 그 결과, 0.1~30.0 중량%의 히알루론산염 용액 (300~100,000cPs)을 자동 도포기에서 캐스팅 후, 30~50℃의 온도 조건에서 건조시키면, 표면이 균일한 히알루론산염 필름을 대량으로 제조할 수 있다는 것을 확인할 수 있었다. 또한, 제조된 히알루론산염 필름은 기계적 물성이 우수하여, 일반 가위, 칼 및 일반 성형 몰드를 사용하여 원하는 형태로 쉽게 성형이 가능하다는 것을 확인할 수 있었다.In the present invention, a hyaluronic acid salt solution is prepared by dissolving a hyaluronic acid salt in water or an aqueous solution of ethanol to prepare a 0.1 to 30.0 wt% hyaluronate solution, casting it into an automatic coater, casting the mixture to various thicknesses, drying at 30 to 50 ° C, Acid salt film was prepared. As a result, casting of 0.1 to 30.0% by weight of hyaluronate solution (300 to 100,000 cPs) in an automatic coater and drying at a temperature of 30 to 50 ° C resulted in the production of a hyaluronate film having a uniform surface I can confirm that I can do it. In addition, the hyaluronate film produced was excellent in mechanical properties, and it was confirmed that the hyaluronate film was easily formed into a desired shape using general scissors, knives, and general molding molds.

따라서, 본 발명은 일 관점에서, (a) 히알루론산염을 용매로 용해시켜 0.1~30.0중량%의 히알루론산염 용액을 제조하는 단계; (b) 상기 제조된 히알루론산염 용액을 자동 도포기에 주입하고, 0.025~5㎜의 두께로 필름을 캐스팅하는 단계; 및 (c) 캐스팅 된 필름을 30~50℃ 조건에서 건조시키는 단계를 포함하는 자동 도포기에 의한 히알루론산염 필름의 제조방법에 관한 것이다.Accordingly, in one aspect, the present invention provides a method for producing a hyaluronate, comprising: (a) dissolving a hyaluronate in a solvent to prepare a 0.1 to 30.0 wt% hyaluronate solution; (b) casting the prepared hyaluronate solution into an automatic coater and casting the film to a thickness of 0.025 to 5 mm; And (c) drying the cast film at 30 to 50 ° C.

본 발명에 있어서, 히알루론산염은 히알루론산에 염이 결합되어 있는 것으로서, 히알루론산나트륨, 히알루론산칼슘, 히알루론산칼륨 등을 예시할 수 있으나 이에 한정되는 것은 아니다.In the present invention, the hyaluronic acid salt is a salt in which hyaluronic acid is bound, and examples thereof include sodium hyaluronate, calcium hyaluronate, and potassium hyaluronate, but are not limited thereto.

본 발명에 있어서, 히알루론산염의 분자량은 특별한 제한없이 사용할 수 있으나, 0.1~3.0MDa인 것이 바람직하다. 또한, 상기 히알루론산염 용액의 히알루론산염의 함량은 0.1~30.0중량%인 것을 특징으로 한다. 즉, 상기 히알루론산염 용액의 농도가 0.1중량% 미만인 경우에는 필름 성형의 어려움이 있고, 30중량%를 초과할 경우에는 높은 점도로 인하여 필름 표면이 불규칙하게 될 우려가 있다. 참고로, 상기 범위의 히알루론산염 용액의 점도는 300~100,000cPs에 해당된다. 저분자량의 히알루론산의 경우 고농도로 용해하여 상기 기준 점도를 맞추어야 하며 고분자량의 히알루론산의 경우 저농도로 용해하여 상기 기준 점도를 맞추어야 균일한 필름을 제조할 수 있다.In the present invention, the molecular weight of the hyaluronic acid salt can be used without particular limitation, but it is preferably 0.1 to 3.0 MDa. The content of the hyaluronate of the hyaluronate solution is 0.1 to 30.0% by weight. That is, when the concentration of the hyaluronate solution is less than 0.1% by weight, film formation is difficult. When the concentration exceeds 30% by weight, the film surface may be irregular due to high viscosity. For reference, the viscosity of the hyaluronate solution in the above range corresponds to 300 to 100,000 cPs. In the case of low molecular weight hyaluronic acid, it is necessary to dissolve at a high concentration to meet the reference viscosity. In the case of high molecular weight hyaluronic acid, it is dissolved at a low concentration and the reference viscosity must be met to produce a uniform film.

상기 용매는 히알루론산염을 용해시키기 위한 것으로서, 100% 물 또는 에탄올 수용액을 사용할 수 있으며, 에탄올 수용액은 에탄올의 함량이 0.01~30부피%인 것이 바람직하다. 물을 단독으로 사용하여 히알루론산염을 용해시킬 경우에는 미생물 오염 방지를 위하여 많은 주의가 필요하지만, 에탄올 수용액으로 히알루론산염을 용해시킬 경우에는 에탄올 함량이 증가함에 따라 미생물 오염 방지효과가 우수할 뿐만 아니라 필름 형성시간을 단축시킬 수 있는 효과가 있다. 하지만, 에탄올 함량이 30부피%를 초과할 경우에는 히알루론산염의 분자량이 증가함에 따라 필름이 불투명해지거나 필름이 형성되지 않는 문제점이 있다. The solvent is used to dissolve the hyaluronate, and 100% water or an aqueous ethanol solution may be used, and the ethanol aqueous solution preferably has an ethanol content of 0.01 to 30% by volume. When water alone is used to dissolve hyaluronate, a great deal of attention is needed to prevent microbial contamination. However, when the hyaluronate is dissolved in an aqueous solution of ethanol, the effect of preventing microbial contamination But the film forming time can be shortened. However, when the ethanol content exceeds 30% by volume, there is a problem that the film becomes opaque or film is not formed as the molecular weight of the hyaluronic acid salt increases.

상기 캐스팅 단계는 5~20mm/s의 속도로 일정하게 수행하는 것이 바람직하다.The casting step is preferably performed at a constant speed of 5 to 20 mm / s.

본 발명에 있어서, 자동 도포기는 일반 필름 제조시 널리 사용되는 기기로서, 도 1에 도시된 바와 같이 본체와 필름의 두께를 조절하는 어플리케이터 및 두께조절 다이얼을 포함한다. In the present invention, the automatic dispenser is widely used in general film production, and includes an applicator for adjusting the thickness of the main body and the film and a thickness adjusting dial as shown in FIG.

본 발명에 있어서, 히알루론산염 필름의 두께는 0.025~5㎜인 것이 바람직하다. 히알루론산염 필름의 두께가 0.025㎜ 미만인 경우는 필름 형성이 어렵고, 5㎜를 초과할 경우에는 필름의 두께가 두꺼워짐에 따라 흐름성이 커져 표면에 주름이 발생하고 건조 시 장시간이 소요되는 단점이 있다. In the present invention, the thickness of the hyaluronate film is preferably 0.025 to 5 mm. When the thickness of the hyaluronate film is less than 0.025 mm, film formation is difficult. When the thickness of the hyaluronate film is more than 5 mm, the thickness of the film becomes thicker, resulting in increased flowability and wrinkles on the surface, have.

본 발명에 있어서, 캐스팅 된 필름의 건조는 30~50℃ 조건에서 6~24시간동안 수행하는 것이 바람직하다. 상기 건조는 30~50℃에서 수행되는 한, 특별한 제한없이 다양한 건조방법으로 수행될 수 있다. In the present invention, drying of the cast film is preferably carried out at 30 to 50 ° C for 6 to 24 hours. The drying can be carried out by various drying methods without particular limitation, as long as the drying is carried out at 30 to 50 ° C.

참고로, 용매 캐스팅 방법으로 히알루론산염 필름을 건조시키는 경우에는 항온항습 건조 조건에서는 필름이 형성되지만, 순환 건조조건에서는 필름이 형성되지 않는 문제점이 있다.For reference, when the hyaluronate film is dried by the solvent casting method, the film is formed under the constant temperature and humidity drying conditions, but the film is not formed under the circulating drying condition.

상기 건조시간은 히알루론산염 용액의 농도 및 자동 도포기 내의 어플리케이터의 조절에 따라 상기 범위 내에서 적절히 조절할 수 있다.The drying time can be appropriately adjusted within the range according to the concentration of the hyaluronate solution and the adjustment of the applicator in the automatic applicator.

본 발명은 다른 관점에서 상기 방법으로 제조된 히알루론산염 필름에 관한 것이다. The present invention relates to a hyaluronate film produced by this method from a different viewpoint.

상기 히알루론산염 필름은 인장강도가 50~300MPa인 것을 특징으로 한다.The hyaluronate film has a tensile strength of 50 to 300 MPa.

상기 히알루론산염 필름의 물성은 히알루론산염의 분자량과 농도 및 두께에 따라 조절이 가능하다. The physical properties of the hyaluronate film can be controlled depending on the molecular weight, concentration and thickness of the hyaluronic acid salt.

본 발명은 또 다른 관점에서 상기 히알루론산염 필름을 포함하는 화장품용 마스크 팩, 패치 및 의료기기용 인공 피부 및 유착 방지제에 관한 것이다. In another aspect, the present invention relates to a cosmetic mask pack, a patch, and an artificial skin and an anti-adhesion agent for a medical device comprising the hyaluronate film.

참고로, 유착(adhesion)은 보통 염증의 치유 과정에서 볼 수 있는 것으로, 육아조직이나 반흔(scar)을 형성할 때 서로 엉겨 붙거나, 다량으로 석출(析出)되는 섬유소가 엉기는 것을 의미한다. 일반적으로, 개복수술 후 67~93% 정도의 빈도로 유착이 발생하며 이 중 일부는 자발적으로 분해되기도 하지만, 대부분의 경우 상처 치유 후에도 유착이 존재하여 각종 후유증을 유발하므로, 수술 후의 상처 부위를 감싸 덮어주거나 약물학적 작용 등으로 주변조직과의 유착 발생을 물리, 화학적으로 차단하기 위하여 유착 방지제가 사용된다. For reference, adhesion is usually seen during the healing process of inflammation, which means that the fibrous material that is entangled or massively precipitated when forming granulation tissue or scar is entangled. Generally, adhesion occurs at a frequency of 67 ~ 93% after laparotomy, and some of them are spontaneously decomposed. However, in most cases, after wound healing, adhesion occurs and causes various sequelae. An anti-adhesion agent is used to physically and chemically block the occurrence of adhesion with surrounding tissues such as covering or pharmacological action.

[실시예][Example]

이하, 실시예를 통하여 본 발명을 더욱 상세히 설명하고자 한다. 이들 실시예는 오로지 본 발명을 예시하기 위한 것으로, 본 발명의 범위가 이들 실시예에 의해 제한되는 것으로 해석되지 않는 것은 당 업계에서 통상의 지식을 가진 자에게 있어서 자명할 것이다. Hereinafter, the present invention will be described in more detail with reference to Examples. It is to be understood by those skilled in the art that these embodiments are only for illustrating the present invention and that the scope of the present invention is not construed as being limited by these embodiments.

실시예 1: 분자량 변화에 따른 필름 형성능 확인Example 1: Determination of Film Formation Ability According to Molecular Weight Change

히알루론산염 분자량에 따른 필름 형성능을 확인하기 위하여, 분자량 0.1MDa, 0.8MDa, 1.2MDa 및 2.5MDa 총 4가지의 히알루론산 나트륨 (Hi-AquaTM) ( (주) 진우바이오)을 20부피% 에탄올 수용액에 0.1~30중량% 농도로 용해시킨 후, 자동 도포기 (COAD 411, 의왕기계, 한국)의 어플리케이터를 조절하여 0.025~5㎜ 두께의 필름을 캐스팅 후 항온항습 건조기 (상대 습도 50%, 온도 40℃)에서 6~24시간 건조하여 히알루론산염 필름을 제조하고, 점도에 따른 필름의 상태를 확인하고 도 2에 나타내었다. To confirm the film-forming ability according to the molecular weight of the hyaluronate, four hyaluronate (Hi-Aqua TM ) (Jinwai Bio) having a molecular weight of 0.1MDa, 0.8MDa, 1.2MDa and 2.5MDa (COAD 411, UWANG MACHINERY, KOREA) was controlled to cast a film having a thickness of 0.025 to 5 mm, and then dried in a constant temperature and humidity dryer (relative humidity 50%, temperature 40 ° C) for 6 to 24 hours to prepare a hyaluronate film, and the state of the film according to the viscosity was confirmed and shown in FIG.

참고로, 자동 도포기를 이용한 필름 제조를 위한 히알루론산염의 점도는 다음의 조건 하에서 측정하였다. For reference, the viscosity of the hyaluronic acid salt for producing a film using an automatic applicator was measured under the following conditions.

측정기기 Brookfield RV-II 점도계 (Spindle No. 7번, 12 rpm, 25℃) Measuring instrument Brookfield RV-II viscometer (Spindle No. 7, 12 rpm, 25 캜)

도 2에 도시된 바와 같이, 히알루론산염의 분자량에 상관없이 히알루론산염 용액의 점도 값이 300cPs 이하(저점도)인 경우에는 필름 형성이 불가능하였으며, 300~100,000cPs(최적 점도)이면 자동 도포기에 의해 표면이 균일한 필름 제조가 가능하였으나, 100,000cPs 이상(고점도)이면 높은 점도로 인해 자동 도포기 사용에도 불구하고 표면이 서로 엉기어 고르지 못한 외형을 지니기 때문에 필름 형성이 불가능함을 확인할 수 있었다. As shown in FIG. 2, irrespective of the molecular weight of the hyaluronic acid salt, film formation was impossible when the viscosity of the hyaluronate solution was 300 cPs or less (low viscosity). When the viscosity was 300 to 100,000 cPs (optimal viscosity) It was confirmed that film formation was impossible because the surface was uneven and irregular in appearance despite the use of automatic dispenser due to high viscosity when the viscosity was 100,000 cPs or more (high viscosity).

실시예 2: 건조 조건에 따른 필름 형성능 확인Example 2: Confirmation of film forming ability according to drying conditions

건조 조건에 따른 필름 형성능을 확인하기 위하여, 분자량 1.2MDa 히알루론산 나트륨을 10부피% 에탄올 수용액에 2.0 중량% 농도로 용해시킨 후 자동 도포기 내의 어플리케이터로 필름의 두께를 0.1㎜로 조절하여 캐스팅하고, 항온항습 건조기(상대 습도 50~90%와 온도 30~60℃)와 순환 건조기(온도 30~60℃)에서 6~24시간 건조하여 히알루론산염 필름을 제조하고, 건조 조건에 따른 필름의 상태를 도 3에 나타내었다. In order to confirm the film-forming ability according to the drying conditions, 1.2 M Na sodium hyaluronate was dissolved in a 10% by volume ethanol aqueous solution at a concentration of 2.0 wt%, and the film was cast by adjusting the thickness of the film to 0.1 mm with an applicator in an automatic applicator, The film was dried for 6 to 24 hours in a constant temperature and humidity dryer (relative humidity of 50 to 90% and temperature of 30 to 60 ° C) and a circulating dryer (temperature of 30 to 60 ° C) to prepare a hyaluronate film, 3.

도 3에 도시된 바와 같이, 자동 도포기에 의하여 제조된 히알루론산염 필름은 항온항습 건조기 뿐만 아니라, 순환 건조기에서도 필름 표면이 매우 균일하게 잘 형성되는 것을 확인할 수 있었다. As shown in FIG. 3, it was confirmed that the film surface of the hyaluronate film produced by the automatic applicator was uniformly formed in the circulation drier as well as the constant temperature and humidity drying dryer.

또한, 순환 건조기를 이용할 경우에는 항온항습 건조기에서 보다 건조 시간이 12시간 이상 단축되어 보다 신속하게 히알루론산염 필름을 생산할 수 있음을 확인할 수 있었다.In addition, when the circulation dryer was used, it was confirmed that the drying time was shortened more than 12 hours in the constant temperature and humidity dryer, and the hyaluronate film could be produced more quickly.

비교예 1: 히알루론산염 용액 점도에 따른 필름 형성능 확인Comparative Example 1: Determination of film forming ability according to viscosity of hyaluronate solution

히알루론산염의 용액 점도에 따른 필름 캐스팅에 의한 필름 형성능을 확인하기 위하여 분자량 0.1~2.5MDa인 히알루론산나트륨 (Hi-AquaTM) ((주) 진우바이오)을 10부피% 에탄올 수용액에 0.1~30중량%의 농도로 용해시킨 후 자동 도포기의 어플리케이터로 필름의 두께를 0.1㎜로 조절하여 캐스팅하고 항온항습 건조기(상대 습도 50%와 온도 50℃)에서 24시간 이상 건조하여 히알루론산염 필름을 제조하고, 점도에 따른 필름의 상태를 확인하고 도 4에 나타내었다. In order to confirm the film forming ability by film casting according to the solution viscosity of the hyaluronic acid salt, hyaluronic acid sodium salt (Hi-Aqua TM ) having a molecular weight of 0.1 to 2.5 MDa (Jinwoo Bio) was added to a 10 volume% %, The film was adjusted to a thickness of 0.1 mm with an applicator of an automatic applicator, casted and dried in a constant-temperature and constant-humidity dryer (relative humidity 50% and a temperature of 50 ° C) for 24 hours or more to prepare a hyaluronate film , And the state of the film according to the viscosity was confirmed and shown in Fig.

자동 도포기를 이용한 필름 제조를 위한 히알루론산염의 점도는 실시예 1과 동일하게, 다음의 조건 하에서 측정하였다.The viscosity of the hyaluronate for producing a film using an automatic applicator was measured under the following conditions in the same manner as in Example 1. [

측정기기 Brookfield RV-II 점도계 (Spindle No. 7번, 12 rpm, 25℃) Measuring instrument Brookfield RV-II viscometer (Spindle No. 7, 12 rpm, 25 캜)

히알루론산염의 분자량에 상관없이 히알루론산염 용액의 점도 값이 300cPs 이하(저점도)의 경우에는 필름 형성이 불가능하였으며 100,000cPs 이상(고점도)일 경우에는 과도한 점성으로 인해 표면이 균일한 필름 형성이 불가능하며 최적 점도에서 건조시킬 경우, 도 4에 나타낸 것과 같이 표면이 균일하게 필름이 잘 형성됨을 확인할 수 있었다. Regardless of the molecular weight of the hyaluronate, film formation is not possible when the viscosity of the hyaluronate solution is less than 300 cPs (low viscosity). When the viscosity is higher than 100,000 cPs (high viscosity), it is impossible to form a uniform film on the surface due to excessive viscosity. And it was confirmed that the film was uniformly formed on the surface as shown in FIG. 4 when dried at the optimum viscosity.

비교예 2: 필름 두께에 따른 필름 형성능 확인Comparative Example 2: Determination of film formability according to film thickness

자동 도포기의 어플리케이터의 두께 조절에 따른 히알루론산염의 필름 형성능을 확인하기 위하여 분자량 1.2MDa 히알루론산 나트륨을 10부피% 에탄올 수용액에 2.0 중량% 농도로 용해시킨 후 필름 어플리케이터로 필름의 두께를 0.024~5.001㎜로 조절하여 캐스팅하고 항온 항습 건조기(상대 습도 50%와 온도 50℃)에서 24시간 이상 건조하여 히알루론산염 필름을 제조하고, 건조 조건에 따른 필름의 상태를 도 5에 나타내었다.In order to confirm the film forming ability of the hyaluronate according to the thickness of the applicator of the automatic applicator, the sodium molecular weight of 1.2MDa hyaluronate was dissolved in a 10% by volume aqueous ethanol solution at a concentration of 2.0% by weight and the thickness of the film was adjusted to 0.024 to 5.001 Mm and dried for 24 hours or longer in a constant-temperature and constant-humidity dryer (relative humidity of 50% and temperature of 50 ° C) to prepare a hyaluronate film, and the state of the film according to the drying condition is shown in FIG.

도 5에 도시된 바와 같이, 필름의 두께가 0.025㎜ 미만일 경우에는 필름 표면이 매우 굴곡을 이루어 활용이 곤란하였으며, 5㎜를 초과할 경우에는 성형이 불가능한 상태로 캐스팅되며, 성형이 되더라도 필름 표면이 균일하지 못하고 건조 시 과도한 시간이 소요되어 필름이 변형됨으로 필름 제조에 적합하지 않음을 확인할 수 있었다. As shown in FIG. 5, when the thickness of the film is less than 0.025 mm, the surface of the film is extremely curved and difficult to use. When the thickness exceeds 5 mm, the film is cast in a state in which molding is impossible. It was found that the film was not uniform and not suitable for film production because the film was deformed due to excessive time for drying.

실험예 1: 히알루론산염 필름의 기계적 물성 측정Experimental Example 1: Measurement of mechanical properties of a hyaluronate film

실시예 1에서 제조된 히알루론산염 필름의 기계적 물성을 측정하기 위하여, TA-XT2i Texture Analyzer (Stable Micro System, UK)를 사용하여 제조된 필름을 3cm × 5cm로 자르고, 인장그립(Tensile grips) 부분에 장착한 후 인장강도 및 신장율을 측정하고 그 결과를 표 1에 나타내었다.In order to measure the mechanical properties of the hyaluronate film prepared in Example 1, the film prepared using the TA-XT2i Texture Analyzer (Stable Micro System, UK) was cut into 3 cm x 5 cm, and the tensile grips And tensile strength and elongation were measured. The results are shown in Table 1. [Table 1]

히알루론산염 용액의 분자량 (MDa)The molecular weight of the hyaluronate solution (MDa) 0.10.1 0.80.8 1.21.2 1.51.5 2.52.5 인장 강도
(Tensile Strength)
The tensile strength
(Tensile Strength)
30~3530 to 35 120~130120 ~ 130 151~170151-170 210~240210-240 300~321300 to 321
신장율 (%)Elongation (%) 12~1512 to 15 25~3325 to 33 45~5045 to 50 55~5855 to 58 65~6865 ~ 68

히알루론산염 필름의 기계적 물성 측정 결과 필름 제조 시의 히알루론산염의 농도 또는 히알루론산의 용액의 점도에는 영향을 받지 않고 분자량에 영향을 받음을 알 수 있었다. The mechanical properties of the hyaluronate film were found to be affected by the molecular weight without being influenced by the concentration of the hyaluronate or the viscosity of the solution of the hyaluronic acid at the time of film production.

표 1로부터, 히알루론산염의 분자량이 높아질수록 인장 강도 30~321MPa로 증가하며 또한 인장 강도는 12~68%로 증가되어짐을 알 수 있었다. From Table 1, it can be seen that as the molecular weight of the hyaluronic acid salt increases, the tensile strength increases to 30 ~ 321 MPa and the tensile strength increases to 12 ~ 68%.

이상으로 본 발명 내용의 특정한 부분을 상세히 기술하였는바, 당업계의 통상의 지식을 가진 자에게 있어서 이러한 구체적 기술은 단지 바람직한 실시 양태일 뿐이며, 이에 의해 본 발명의 범위가 제한되는 것이 아닌 점은 명백할 것이다. 따라서 본 발명의 실질적인 범위는 첨부된 청구항들과 그것들의 등가물에 의하여 정의된다고 할 것이다.While the present invention has been particularly shown and described with reference to specific embodiments thereof, those skilled in the art will appreciate that such specific embodiments are merely preferred embodiments and that the scope of the present invention is not limited thereto will be. It is therefore intended that the scope of the invention be defined by the claims appended hereto and their equivalents.

Claims (8)

(a) 히알루론산염을 용매로 용해시켜 0.1~30.0중량%의 히알루론산염 용액을 제조하는 단계;
(b) 상기 제조된 히알루론산염 용액을 자동 도포기에 주입하고, 0.025~5㎜의 두께로 필름을 캐스팅하는 단계; 및
(c) 캐스팅 된 필름을 30~50℃ 조건에서 건조시키는 단계를 포함하는 자동 도포기에 의한 히알루론산염 필름의 제조방법.
(a) dissolving hyaluronate as a solvent to prepare 0.1 to 30.0% by weight of a hyaluronate solution;
(b) casting the prepared hyaluronate solution into an automatic coater and casting the film to a thickness of 0.025 to 5 mm; And
(c) drying the cast film at 30 to 50 ° C.
제1항에 있어서, 상기 히알루론산염 용액의 점도는 300~100,000cPs인 것을 특징으로 하는 자동 도포기에 의한 히알루론산염 필름의 제조방법.
The method for preparing a hyaluronate film according to claim 1, wherein the viscosity of the hyaluronate solution is 300 to 100,000 cPs.
제1항 또는 제2항의 방법으로 제조된 히알루론산염 필름.
A hyaluronate film produced by the method of claim 1 or 2.
제3항에 있어서, 상기 히알루론산염 필름의 인장강도는 50~300 MPa인 것을 특징으로 하는 히알루론산염 필름.
The hyaluronate film according to claim 3, wherein the hyaluronate film has a tensile strength of 50 to 300 MPa.
제3항의 히알루론산염 필름을 포함하는 마스크 팩.
A mask pack comprising the hyaluronate film of claim 3.
제3항의 히알루론산염 필름을 포함하는 패치.
A patch comprising the hyaluronate film of claim 3.
제3항의 히알루론산염 필름을 포함하는 인공피부.
An artificial skin comprising the hyaluronate film of claim 3.
제3항의 히알루론산염 필름을 포함하는 유착 방지제. An anti-adhesion agent comprising the hyaluronate film of claim 3.
KR1020170125213A 2017-03-07 2017-09-27 Preparation Method of Sodium Hyaluronate Film by Automatic Control Coater and Sodium Hyaluronate Film prepared Thereof KR102030496B1 (en)

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