JP4592459B2 - Antibacterial composition containing chitosan - Google Patents
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Description
本発明は、キトサン誘導体を含む抗菌組成物および該抗菌組成物が表面に付着してなる高分子製品に関する。 The present invention relates to an antibacterial composition containing a chitosan derivative and a polymer product obtained by adhering the antibacterial composition to a surface.
高分子製品、特に絨毯、カーペットなどに使用される合成繊維製品に抗菌性を付与することが望まれている。抗菌性を与える物質として近年、キトサンを使用することが注目されている（特許文献１、２）。 It is desired to impart antibacterial properties to polymer products, particularly synthetic fiber products used for carpets, carpets and the like. In recent years, the use of chitosan as a substance imparting antibacterial properties has attracted attention (Patent Documents 1 and 2).
キトサンは、甲殻類から得られるキチン（β−１，４−ポリ−Ｎ−アセチル−Ｄ−グルコサミン）を熱濃アルカリ液中で脱アセチル化した誘導体（β−１，４−ポリ−Ｄ−グルコサミン）であり、生体適合性に優れた分子量５万〜５０万程度の天然高分子である。キトサンには、生分解性があり、抗菌性（特に大腸菌等、食品中などで増殖する菌の生育を阻害する作用）、保湿性、抗アレルギー性等の作用を示すばかりでなく、他の抗菌剤と比べて人体や環境に安全であることから、キトサンを含む繊維や膜などを開発する研究が盛んになってきている。
なお、キトサンの抗菌性は、分子量１０，０００以上で発揮されるが、分子量４，０００程度では発揮されない。
Chitosan is a derivative (β-1,4-poly-D-glucosamine) obtained by deacetylating chitin (β-1,4-poly-N-acetyl-D-glucosamine) obtained from crustaceans in a hot concentrated alkaline solution. It is a natural polymer having a molecular weight of about 50,000 to 500,000, which is excellent in biocompatibility. Chitosan is not only biodegradable but also antibacterial (especially an action that inhibits the growth of bacteria that grow in food such as E. coli), moisturizing and antiallergic properties, as well as other antibacterial properties. Since it is safer for the human body and the environment than agents, research to develop fibers and membranes containing chitosan has become active.
The antibacterial properties of chitosan are exhibited at a molecular weight of 10,000 or more, but not at a molecular weight of about 4,000.
キチン・キトサンを高分子表面に塗布する方法として、例えば、高分子製品の表面に紫外線を照射した後、キチン・キトサン溶液を付着させ、乾燥させる方法（特許文献３）が知られている。
しかし上記方法においては、キチン・キトサン分子は、それらのアミノ基を介した化学結合により高分子表面に付着しているため、アミノ基を失ったキトサンは十分な抗菌性を発揮できないうえ、洗濯などでキトサン膜が剥離するなどの問題がある。
As a method for applying chitin / chitosan to a polymer surface, for example, a method is known in which a chitin / chitosan solution is attached and dried after irradiating the surface of the polymer product with ultraviolet rays (Patent Document 3).
However, in the above method, chitin / chitosan molecules are attached to the polymer surface through chemical bonds via their amino groups, so that chitosans that have lost amino groups cannot exhibit sufficient antibacterial properties, and washing, etc. However, there are problems such as peeling of the chitosan film.
一方、キトサン誘導体とポリエチレングリコール誘導体を用いて合成繊維製品を加工する方法も提案されている（特許文献４）。
しかしこの方法は耐久性にすぐれた親水性能を付与することを目的とするものであり、抗菌性に関する開示はなされていない。
On the other hand, a method of processing a synthetic fiber product using a chitosan derivative and a polyethylene glycol derivative has also been proposed (Patent Document 4).
However, this method is intended to provide hydrophilic performance with excellent durability, and no disclosure regarding antibacterial properties has been made.
したがって、高分子製品にキトサンの有する抗菌性を十分に付与することができる技術が望まれている。なお、高分子製品とキトサンとは溶融しないため、溶融以外の方法でキトサンの抗菌性を高分子製品に付与する技術が求められている。
本発明は、人体に安全であり、かつ十分な抗菌性を付与することができる抗菌組成物を提供することを目的とする。 An object of the present invention is to provide an antibacterial composition that is safe to the human body and can impart sufficient antibacterial properties.
本発明は、キトサン、ゼラチンおよび架橋剤を含有する抗菌組成物を提供する。
本発明はまた、本発明の抗菌組成物が表面に付着してなる高分子製品を提供する。
さらに本発明は、本発明の抗菌組成物を高分子製品に適用し、乾燥させる高分子製品の抗菌処理方法を提供する。
The present invention provides an antimicrobial composition containing chitosan, gelatin and a crosslinking agent.
The present invention also provides a polymer product obtained by adhering the antimicrobial composition of the present invention to a surface.
Furthermore, the present invention provides an antibacterial treatment method for a polymer product, wherein the antibacterial composition of the present invention is applied to the polymer product and dried.
本発明により、種々の高分子製品に、キトサンの抗菌性を付与することが可能となる。 The present invention makes it possible to impart antibacterial properties of chitosan to various polymer products.
本発明の抗菌組成物は、キトサン、ゼラチンおよび架橋剤を含有するものである。好ましくは、キトサン濃度、ゼラチン濃度および架橋剤濃度はそれぞれ０．１〜１．０重量％、０．０２〜０．２重量％および０．０５〜０．２重量％である。 The antibacterial composition of the present invention contains chitosan, gelatin and a crosslinking agent. Preferably, the chitosan concentration, gelatin concentration and crosslinker concentration are 0.1 to 1.0 wt%, 0.02 to 0.2 wt% and 0.05 to 0.2 wt%, respectively.
本発明においてキトサンとは、分子量１０，０００〜２００，０００、好ましくは１０，０００〜７５，０００、より好ましくは１０，０００〜４０，０００、脱アセチル化度７５〜９８％のものをいう。 In the present invention, chitosan means one having a molecular weight of 10,000 to 200,000, preferably 10,000 to 75,000, more preferably 10,000 to 40,000, and a deacetylation degree of 75 to 98%.
ゼラチンは、市販のものでもよいし、天然（動物の骨、皮）由来のものでもよい。また、かかる市販または天然由来のゼラチンをアルカリ加水分解したゼラチン、酸加水分解したゼラチンを用いてもよい。ゼラチンの分子量は１０，０００〜１００，０００程度のものが好ましい。なお、ゼラチンは本発明の抗菌組成物において結合剤（バインダー）として作用すると同時に、ゼラチンは染色性が良好なことから、高分子製品、特に繊維製品の染色性が向上する。 The gelatin may be commercially available or derived from nature (animal bone, skin). Further, gelatin obtained by alkali hydrolysis or acid hydrolysis of such commercially available or naturally-derived gelatin may be used. The molecular weight of gelatin is preferably about 10,000 to 100,000. In addition, gelatin acts as a binder (binder) in the antibacterial composition of the present invention, and at the same time, gelatin has good dyeability, so that dyeability of polymer products, particularly fiber products, is improved.
架橋剤は、化学反応によってゼラチン分子を架橋させる作用を有するものであれば特に限定されず、例えば、グルタルアルデヒド、多価グリシジル化合物が挙げられる。多価グリシジル化合物としては、ソルビトールポリグリシジルエーテル、ペンタエリスリトールポリグリシジルエーテル、グリセロールポリグリシジルエーテル、レゾルシノールジグリシジルエーテル、ネオペンチルグリコールジグリシジルエーテル、水添ビスフェノールＡ型ジグリシジルエーテル、ポリエチレングリコールジグリシジルエーテル、ポリプロピレングリコールジグリシジルエーテル等が挙げられる。かかる多価グリシジル化合物としては、市販のものを使用することもでき、例えば、ナガセケムテックス（株）製、「デナコールＥＸ−９３１」、「デナコールＥＸ−８４１」、「デナコールＥＸ−４１１」、「デナコールＥＸ−２５２」、「デナコールＥＸ−３１４」、「デナコールＥＸ−６１４Ｂ」、「デナコールＥＸ−２０１」、「デナコールＥＸ−２１１」等が挙げられる。架橋剤としてはグルタルアルデヒドが特に好ましい。 The cross-linking agent is not particularly limited as long as it has an action of cross-linking gelatin molecules by a chemical reaction, and examples thereof include glutaraldehyde and polyvalent glycidyl compounds. Examples of the polyvalent glycidyl compound include sorbitol polyglycidyl ether, pentaerythritol polyglycidyl ether, glycerol polyglycidyl ether, resorcinol diglycidyl ether, neopentyl glycol diglycidyl ether, hydrogenated bisphenol A type diglycidyl ether, polyethylene glycol diglycidyl ether, Examples thereof include polypropylene glycol diglycidyl ether. As such polyvalent glycidyl compounds, commercially available ones can also be used. Examples include Denacol EX-252, Denacol EX-314, Denacol EX-614B, Denacol EX-201, and Denacol EX-211. Glutaraldehyde is particularly preferred as the cross-linking agent.
本発明の抗菌組成物の調製方法は、本発明の抗菌組成物が得られる限り特に限定されず、各成分を同時に水に添加してもよいし、それぞれ水溶液とした後に混合してもよい。あるいは、成分の一部の水溶液に残りの成分を添加してもよい。そのような調製方法としては例えば、キトサン水溶液とゼラチン水溶液を混合した液に架橋剤を添加する方法が挙げられる。 The method for preparing the antibacterial composition of the present invention is not particularly limited as long as the antibacterial composition of the present invention is obtained. Each component may be added to water at the same time, or may be mixed after being made into an aqueous solution. Alternatively, the remaining components may be added to a partial aqueous solution of the components. Examples of such a preparation method include a method of adding a cross-linking agent to a liquid obtained by mixing a chitosan aqueous solution and a gelatin aqueous solution.
本発明による抗菌組成物が表面に付着してなる高分子製品とは、本発明による抗菌組成物を適用され、水分を乾燥により除去することにより、本発明の抗菌物質、即ちキトサンがその表面に付着した高分子製品である。本発明の抗菌組成物を付着される高分子製品は特に限定されず、合成高分子からなる製品であっても天然高分子からなる製品であってもよい。本発明においては、抗菌物質であるキトサンがゼラチンの接着力および架橋剤による化学反応によって高分子製品に付着する。 The polymer product obtained by adhering the antibacterial composition according to the present invention to the surface is applied with the antibacterial composition according to the present invention, and the antibacterial substance of the present invention, that is, chitosan, is applied to the surface by removing moisture by drying. Adhered polymer product. The polymer product to which the antibacterial composition of the present invention is attached is not particularly limited, and may be a product made of a synthetic polymer or a product made of a natural polymer. In the present invention, chitosan, which is an antibacterial substance, adheres to a polymer product by the adhesive force of gelatin and a chemical reaction by a crosslinking agent.
高分子製品の主成分である高分子素材は、天然または合成のいずれであってもよく天然高分子としては、綿、麻、羊毛など、合成高分子としては、ポリオレフィン系、ポリエステル系、全芳香族ポリマー、ポリ塩化ビニリデン、ポリアクリロニトリル系、ポリフッ素系、ポリエポキシ系などが挙げられる。具体的には、ポリオレフィン系合成高分子として、ポリエチレン、ポリプロピレン、エチレンとプロピレンの共重合物または混合物が、ポリエステル系高分子化合物として、ＰＥＴ（ポリエチレンテレフタラート）、ＰＢＴ（ポリブチレンテレフタラート）、ポリエチレン２・６ナフタレート、ポリアリレート、ＰＥＴとＰＢＴの共重合物または混合物が、全芳香族系ポリマーとして、ポリフェニレンサルファイド、ポリイミド、ポリ−ｐ−フェニレン・テレフタルイミド、ポリ−ｍ−フェニレンイソフタルアミド、ポリアリレン・サルファイトが例示される。 The polymer material that is the main component of the polymer product may be either natural or synthetic. Natural polymers include cotton, hemp and wool. Synthetic polymers include polyolefins, polyesters, and aromatics. Group polymer, polyvinylidene chloride, polyacrylonitrile, polyfluorine, polyepoxy and the like. Specifically, polyethylene, polypropylene, a copolymer or mixture of ethylene and propylene is used as the polyolefin-based synthetic polymer, and PET (polyethylene terephthalate), PBT (polybutylene terephthalate), polyethylene is used as the polyester-based polymer compound. 2.6 Naphthalate, Polyarylate, Copolymer or Mixture of PET and PBT are all aromatic polymers such as polyphenylene sulfide, polyimide, poly-p-phenylene terephthalimide, poly-m-phenylene isophthalamide, polyarylene. An example is sulfite.
高分子製品とは、上記のような高分子素材からなる成形品または繊維製品を意味する。具体的には、高分子素材製の成形品、糸、紐、ロープ、織物、不織布などの繊維製品、シート、フィルムなどが挙げられる。 The polymer product means a molded product or a fiber product made of the polymer material as described above. Specific examples include molded articles made of a polymer material, yarns, strings, ropes, textiles such as woven fabrics and non-woven fabrics, sheets and films.
かかる高分子製品のなかでも合成繊維製品が好ましく、合成繊維製品としては特に再生材料として注目されているＰＥＴ繊維製品が好ましい。合成繊維製品の具体例としては、特にハウスダストによるアレルギーなどが問題になっていることから、カーペットが好ましい。また、作業服や白衣など、衛生面が重視される繊維製品なども例示される。 Among such polymer products, synthetic fiber products are preferable, and as the synthetic fiber products, PET fiber products that are particularly attracting attention as recycled materials are preferable. As a specific example of the synthetic fiber product, carpet is preferable because allergy due to house dust is a problem. In addition, textile products such as work clothes and lab coats where hygiene is important are exemplified.
本発明の抗菌組成物を繊維に付着させる場合、繊維重量に対するキトサンおよびゼラチンの付着量は、それぞれ、０．２〜１．０重量％および０．２〜０．８重量％が好ましい。 When the antibacterial composition of the present invention is attached to the fiber, the attached amount of chitosan and gelatin with respect to the fiber weight is preferably 0.2 to 1.0% by weight and 0.2 to 0.8% by weight, respectively.
本発明の抗菌処理方法は、本発明による抗菌組成物を高分子製品に適用する工程および乾燥させる工程を含む。ここで抗菌組成物の適用は、高分子製品に対して抗菌組成物をスプレー装置などにより噴霧して行ってもよいし、抗菌組成物に高分子製品を浸漬して行ってもよい。 The antibacterial treatment method of the present invention includes a step of applying the antibacterial composition according to the present invention to a polymer product and a step of drying. Here, the antibacterial composition may be applied by spraying the antibacterial composition with a spray device or the like on the polymer product, or by immersing the polymer product in the antibacterial composition.
乾燥工程は、抗菌組成物から水分を実質的に除去される限りいかなる方法を用いて行ってもよいが、例えば、繊維をコンベアに載せて１００〜１１０℃で１０〜２０分間熱風乾燥するとよい。乾燥により水分を実質的に除去することにより、抗菌物質であるキトサンを含有する硬化膜が形成される。 The drying step may be performed using any method as long as moisture is substantially removed from the antibacterial composition. For example, the fiber is placed on a conveyor and dried with hot air at 100 to 110 ° C. for 10 to 20 minutes. By substantially removing moisture by drying, a cured film containing chitosan which is an antibacterial substance is formed.
本発明の抗菌処理方法において所望によりさらに熱処理工程を含めてもよい。熱処理は繊維をコンベアに載せて、１１０〜１３０℃にて１０〜３０分間程度行うとよい。熱処理は、乾燥工程と同時に行ってもよいし、乾燥工程の前または後に行ってもよい。熱処理によって架橋反応が促進される。 If desired, the antibacterial treatment method of the present invention may further include a heat treatment step. The heat treatment may be performed for about 10 to 30 minutes at 110 to 130 ° C. with the fiber placed on a conveyor. The heat treatment may be performed simultaneously with the drying step, or may be performed before or after the drying step. The crosslinking reaction is promoted by the heat treatment.
以下、本発明を実施例によりさらに詳細に説明する。 Hereinafter, the present invention will be described in more detail with reference to examples.
（有）グラスベンチャー製キトサン（分子量４０，０００、脱アセチル化度９５％）を４％酢酸水に溶解し、１重量％のキトサン水溶液を調製した。また、宏榮化成（株）製牛骨由来アルカリ処理ゼラチン（分子量１００，０００）を水に溶解し、１重量％のゼラチン水溶液を調製した。これらの水溶液を１．５：１．０の比率で混合し、さらに架橋剤としてグルタルアルデヒドを０．１重量％になるように添加し、本発明の抗菌組成物である塗布液を得た。 (Yes) Glass Venture Chitosan (molecular weight 40,000, deacetylation degree 95%) was dissolved in 4% acetic acid water to prepare a 1% by weight chitosan aqueous solution. Further, beef bone-derived alkali-treated gelatin (molecular weight: 100,000) manufactured by Hiroshi Kasei Co., Ltd. was dissolved in water to prepare a 1% by weight gelatin aqueous solution. These aqueous solutions were mixed at a ratio of 1.5: 1.0, and glutaraldehyde was added as a cross-linking agent so as to be 0.1% by weight to obtain a coating solution which is an antibacterial composition of the present invention.
ＰＥＴ繊維の製造設備の押出ノズルと延伸紡糸部との間に、塗布液の噴霧設備を設置した。噴霧設備に上記塗布液を注入し、キトサン、ゼラチンの付着量が０．６８、０．４５（繊維に対する重量％）となるように噴霧設備を調節して塗布液をＰＥＴ繊維に適用し、乾燥及び熱処理工程を施して、試料を作成した。 A spraying facility for the coating liquid was installed between the extrusion nozzle and the stretch spinning section of the PET fiber manufacturing facility. Inject the above coating solution into the spraying equipment, adjust the spraying equipment so that the adhesion amount of chitosan and gelatin is 0.68, 0.45 (weight% with respect to the fiber), apply the coating liquid to the PET fiber, and dry And a heat treatment step was performed to prepare a sample.
得られた試料を用いて、筒編み地（７ｃｍｘ２０ｃｍ）を作り抗菌性試験の被験サンプルとした。抗菌性試験の方法はシェイクフラスコ法で行った。 Using the obtained sample, a tubular knitted fabric (7 cm × 20 cm) was made and used as a test sample for the antibacterial test. The antibacterial test was performed by the shake flask method.
大腸菌株ＯＷ６(Escherichia coli OW6)、枯草菌株１６８(Bacillus subtilis 168)をＬＢ液体培地（トリプトンペプトン１０ｇ／ｌ、イーストエクストラクト５ｇ／ｌ、ＮａＣｌ５ｇ／ｌ、ＭｎＣｌ２・４Ｈ２Ｏ ０．１ｍＭ、ｐＨ７．０）中で３７℃、１２０ｒｐｍで１６時間培養した。得られた培養液０．０２ｍｌを、被験サンプルまたは対照サンプル（３ｃｍｘ３ｃｍ）を浸したＬＢ液体培地２０ｍｌを含むフラスコに入れて、３７℃、１２０ｒｐｍで７時間培養し濁度（波長６５０ｎｍで測定）の変化を調べた。測定結果を表１に示す。 Escherichia coli OW6, Bacillus subtilis 168, LB liquid medium (trypton peptone 10 g / l, yeast extract 5 g / l, NaCl 5 g / l, MnCl 2 .4H 2 O 0.1 mM, The cells were cultured at 37 ° C. and 120 rpm for 16 hours in pH 7.0). 0.02 ml of the obtained culture solution was put into a flask containing 20 ml of LB liquid medium soaked with a test sample or a control sample (3 cm × 3 cm), cultured at 37 ° C. and 120 rpm for 7 hours, and turbidity (measured at a wavelength of 650 nm). We examined changes. The measurement results are shown in Table 1.
以上の結果から、キトサンで加工したＰＥＴ繊維は大腸菌株ＯＷ６および枯草菌株１６８の増殖を抑制し、抗菌性を示すことが判明した。 From the above results, it was found that PET fibers processed with chitosan suppressed the growth of E. coli strain OW6 and Bacillus subtilis strain 168 and exhibited antibacterial properties.
本発明の抗菌組成物は、様々な高分子製品、特にカーペット、作業服、白衣などの繊維製品に用いることができる。
The antibacterial composition of the present invention can be used for various polymer products, particularly textile products such as carpets, work clothes, and white robes.
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| WO2014038620A1 (en) * | 2012-09-10 | 2014-03-13 | ロート製薬株式会社 | Allergen-reducing agent |
| JP6286639B2 (en) * | 2013-10-07 | 2018-03-07 | 群馬県 | Textile finishing agent |
| CN113652869B (en) * | 2021-08-16 | 2022-05-03 | 广东安之伴实业有限公司 | Preparation process of anti-mite and antibacterial fabric |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0376871A (en) * | 1988-10-17 | 1991-04-02 | Asahi Kasei Textile:Kk | Fabric having good absorbency and its production |
| JPH04257301A (en) * | 1991-02-12 | 1992-09-11 | Asahi Chem Ind Co Ltd | Antifungal and deodorizing leg product and its production |
| JPH0711579A (en) * | 1992-11-09 | 1995-01-13 | Nakagawa Momoki | Functional fiber and fiber product |
| JPH09158048A (en) * | 1995-12-01 | 1997-06-17 | Toray Ind Inc | Functional fiber product |
| JP2001207381A (en) * | 2000-12-20 | 2001-08-03 | Nakamura Kenji | Composition for fiber treatment |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2613769B2 (en) * | 1987-09-02 | 1997-05-28 | 有限会社エム・エス・ケー | Processing of textile products |
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Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0376871A (en) * | 1988-10-17 | 1991-04-02 | Asahi Kasei Textile:Kk | Fabric having good absorbency and its production |
| JPH04257301A (en) * | 1991-02-12 | 1992-09-11 | Asahi Chem Ind Co Ltd | Antifungal and deodorizing leg product and its production |
| JPH0711579A (en) * | 1992-11-09 | 1995-01-13 | Nakagawa Momoki | Functional fiber and fiber product |
| JPH09158048A (en) * | 1995-12-01 | 1997-06-17 | Toray Ind Inc | Functional fiber product |
| JP2001207381A (en) * | 2000-12-20 | 2001-08-03 | Nakamura Kenji | Composition for fiber treatment |
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