JPH0339310A - Production of emulsion containing polyhexamethylenebiguanide salt and antimicrobial, deodorizing processing agent containing same emulsion - Google Patents
Production of emulsion containing polyhexamethylenebiguanide salt and antimicrobial, deodorizing processing agent containing same emulsionInfo
- Publication number
- JPH0339310A JPH0339310A JP1175030A JP17503089A JPH0339310A JP H0339310 A JPH0339310 A JP H0339310A JP 1175030 A JP1175030 A JP 1175030A JP 17503089 A JP17503089 A JP 17503089A JP H0339310 A JPH0339310 A JP H0339310A
- Authority
- JP
- Japan
- Prior art keywords
- emulsion
- salt
- acrylate
- meth
- polyhexamethylenebiguanide
- 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.)
- Pending
Links
- 239000000839 emulsion Substances 0.000 title claims abstract description 25
- VAZJLPXFVQHDFB-UHFFFAOYSA-N 1-(diaminomethylidene)-2-hexylguanidine Polymers CCCCCCN=C(N)N=C(N)N VAZJLPXFVQHDFB-UHFFFAOYSA-N 0.000 title claims abstract description 24
- 230000001877 deodorizing effect Effects 0.000 title claims abstract description 11
- 238000004519 manufacturing process Methods 0.000 title claims description 12
- 230000000845 anti-microbial effect Effects 0.000 title abstract 2
- 238000012545 processing Methods 0.000 title description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims abstract description 17
- 229920002413 Polyhexanide Polymers 0.000 claims abstract description 16
- 239000000178 monomer Substances 0.000 claims abstract description 14
- 239000002202 Polyethylene glycol Substances 0.000 claims abstract description 10
- 229920001223 polyethylene glycol Polymers 0.000 claims abstract description 10
- 150000003839 salts Chemical class 0.000 claims abstract description 10
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract description 8
- 230000000844 anti-bacterial effect Effects 0.000 claims description 17
- 239000003795 chemical substances by application Substances 0.000 claims description 10
- 150000005215 alkyl ethers Chemical class 0.000 claims description 8
- 125000000542 sulfonic acid group Chemical group 0.000 claims description 5
- 239000000835 fiber Substances 0.000 claims description 4
- 238000005406 washing Methods 0.000 abstract description 12
- 230000002378 acidificating effect Effects 0.000 abstract description 5
- -1 acrylate alkyl ether Chemical class 0.000 abstract description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract description 4
- 229920000536 2-Acrylamido-2-methylpropane sulfonic acid Polymers 0.000 abstract description 3
- XHZPRMZZQOIPDS-UHFFFAOYSA-N 2-Methyl-2-[(1-oxo-2-propenyl)amino]-1-propanesulfonic acid Chemical compound OS(=O)(=O)CC(C)(C)NC(=O)C=C XHZPRMZZQOIPDS-UHFFFAOYSA-N 0.000 abstract description 3
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 238000002845 discoloration Methods 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- 229920003176 water-insoluble polymer Polymers 0.000 abstract 1
- 238000006116 polymerization reaction Methods 0.000 description 12
- 229920000642 polymer Polymers 0.000 description 8
- 238000000034 method Methods 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- GHXZTYHSJHQHIJ-UHFFFAOYSA-N Chlorhexidine Chemical compound C=1C=C(Cl)C=CC=1NC(N)=NC(N)=NCCCCCCN=C(N)N=C(N)NC1=CC=C(Cl)C=C1 GHXZTYHSJHQHIJ-UHFFFAOYSA-N 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 229960003260 chlorhexidine Drugs 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 239000004753 textile Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 238000004040 coloring Methods 0.000 description 4
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 description 3
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 3
- 229920000742 Cotton Polymers 0.000 description 3
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium peroxydisulfate Substances [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 3
- VAZSKTXWXKYQJF-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)OOS([O-])=O VAZSKTXWXKYQJF-UHFFFAOYSA-N 0.000 description 3
- 229910001870 ammonium persulfate Inorganic materials 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 241000191967 Staphylococcus aureus Species 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 239000003999 initiator Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000012046 mixed solvent Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- AGBXYHCHUYARJY-UHFFFAOYSA-N 2-phenylethenesulfonic acid Chemical compound OS(=O)(=O)C=CC1=CC=CC=C1 AGBXYHCHUYARJY-UHFFFAOYSA-N 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 239000002781 deodorant agent Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 125000001475 halogen functional group Chemical group 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 235000012149 noodles Nutrition 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 239000004034 viscosity adjusting agent Substances 0.000 description 1
- 238000004383 yellowing Methods 0.000 description 1
Landscapes
- Disinfection, Sterilisation Or Deodorisation Of Air (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Chemical Or Physical Treatment Of Fibers (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Abstract
Description
【発明の詳細な説明】
（産業上の利用分野）
本発明はポリヘキサメチレンビグアナイド塩を含有する
エマルジョンの製法及び該エマルジョンを含有する繊維
用抗菌防臭加工剤に関する。DETAILED DESCRIPTION OF THE INVENTION (Industrial Application Field) The present invention relates to a method for producing an emulsion containing a polyhexamethylene biguanide salt and an antibacterial and deodorizing agent for textiles containing the emulsion.
（従来の技術〉
ポリフルキレングリコール（メタ）アクリレート又はそ
のアルキルエーテル、アルキルエステルと、酸性基を有
する重合性モノマーとを共重合させて得られるポリマー
溶液に、クロルヘキシジン又はその塩を添加することを
特徴とする抗菌加工用液の製造方法が特開昭６１−１５
２６０５号に開示されている。しかしクロルヘキシジン
は紫外線等にさらされると若干の黄変があり、重合時に
おいてもクロルヘキシジンと酸性モノマーをイオン結合
させたものを用いて重合すると、触媒の過酸化物により
褐色になったり、又、重合終了後にクロルヘキシジンを
添加する場合においても触媒活性を充分低下させておか
ないと着色の原因となる等の欠点があった。(Prior art) Chlorhexidine or its salt is added to a polymer solution obtained by copolymerizing polyfulkylene glycol (meth)acrylate or its alkyl ether or alkyl ester with a polymerizable monomer having an acidic group. A method for producing an antibacterial processing liquid is disclosed in Japanese Patent Application Laid-open No. 1986-15.
No. 2605. However, chlorhexidine has a slight yellowing when exposed to ultraviolet rays, etc. During polymerization, when ionically bonded chlorhexidine and acidic monomers are used, the peroxide in the catalyst may cause the color to turn brown, or the polymerization may occur. Even when chlorhexidine is added after completion of the reaction, there are drawbacks such as coloring unless the catalyst activity is sufficiently reduced.
（発明が解決しようとする課題）
本発明の目的は着色の問題がなく且つ安全性、洗濯耐久
性等においても優れた抗菌防臭性を有するエマルジョン
の製法、及び該エマルジョンを含有する線維用抗菌防臭
加工剤を提供することにある。(Problems to be Solved by the Invention) The purpose of the present invention is to provide a method for producing an emulsion that is free from coloring problems and has antibacterial and deodorizing properties that are excellent in terms of safety and washing durability, and an antibacterial and deodorizing method for textiles containing the emulsion. Our goal is to provide processing agents.
（課題を解決するための手段）
本発明は（ａ）ポリヘキサメチレンビグアナイド又はそ
の塩、（ｂ）スルホン酸基を有するモノマー（ｅ）ポリ
エチレングリコール（メタ）アクリレートのアルキルエ
ーテル及び（ｄ）ヒドロキシアルキル（メタ）アクリレ
ートより水に不溶なポリヘキサメチレンビグアナイド塩
を含有するエマルジョンを得る方法、及び該エマルジョ
ンを含有する繊維用抗菌防臭加工剤に係る。(Means for Solving the Problems) The present invention provides (a) polyhexamethylene biguanide or a salt thereof, (b) a monomer having a sulfonic acid group, (e) an alkyl ether of polyethylene glycol (meth)acrylate, and (d) a hydroxyalkyl The present invention relates to a method for obtaining an emulsion containing a polyhexamethylene biguanide salt that is more insoluble in water than (meth)acrylate, and an antibacterial and deodorizing agent for textiles containing the emulsion.
本発明の原料の一成分であるポリヘキサメチレンビグア
ナイドは下記に示す式で表わされる。Polyhexamethylene biguanide, which is a component of the raw material of the present invention, is represented by the formula shown below.
（ＮＨ（ｃＨｚ）６ＮＨＣＮＨＣ）ｎ−ｎＸ （１）
ＮＨＮＨ
（Ｘは酸性基を示す〉
ポリヘキサメチレンビグアナイドは一般に塩酸塩の形で
使用されているが水溶性が強いため、その＊までは洗濯
耐久性において不充分であり、塩の型を変え、不溶化し
更にポリマーに結合させることにより洗濯耐久性が良く
なることを発見した。(NH(cHz)6NHCNHC)n-nX (1)
NHNH (X represents an acidic group) Polyhexamethylene biguanide is generally used in the form of hydrochloride, but because it is highly water-soluble, washing durability up to * is insufficient, so changing the salt type, It has been discovered that washing durability can be improved by making it insolubilized and then bonding it to a polymer.
又ポリヘキサメチレンビグアナイドはクロルヘキシジン
の様な着色に対する影響がないため、スルホン酸とイオ
ン結合させたのち共重合させても何ら問題はなかった。Furthermore, since polyhexamethylene biguanide does not have the same effect on coloring as chlorhexidine, there was no problem even if it was ionically bonded with sulfonic acid and then copolymerized.
又ポリヘキサメチレンビグアナイドを重合終了後ただち
に添加しても着色の影響はなかった。Further, even when polyhexamethylene biguanide was added immediately after completion of polymerization, there was no effect on coloring.
即ち本発明のポリへキサメチレンビグ７ナイド塩の第１
の製法は（、）ポリヘキサメチレンビグアナイド又はそ
の塩と（ｂ）スルホン酸基を有するモノマーをイオン結
合させたのち、（ｃ）ポリエチレングリコール（メタ）
アクリレートのアルキルエーテル及び（ｄ）ヒドロキシ
アルキル（メタ）アクリレートを共重合させる方法であ
り、本発明のポリヘキサメチレンビグアナイド塩の第２
の製法は（ｂ）スルホン酸基を有するモノマー、（ｃ）
ポリエチレングリコール（メタ）アクリレートのアルキ
ルエーテル及び（ｄ）ヒドロキシアルキル（メタ）アク
リレートを共重合させたのち、（ａ）ポリヘキサメチレ
ンビグ７ナイド又はその塩を反応させる方法である。That is, the first polyhexamethylene big7nide salt of the present invention
The manufacturing method is to ionically bond (a) polyhexamethylene biguanide or its salt with (b) a monomer having a sulfonic acid group, and then (c) polyethylene glycol (meth).
This is a method of copolymerizing an alkyl ether of acrylate and (d) hydroxyalkyl (meth)acrylate, and the second polyhexamethylene biguanide salt of the present invention.
The method for producing (b) a monomer having a sulfonic acid group, (c)
In this method, after copolymerizing an alkyl ether of polyethylene glycol (meth)acrylate and (d) hydroxyalkyl (meth)acrylate, (a) polyhexamethylene big 7nide or a salt thereof is reacted.
本発明においてポリへキサメチレンビグ７ｔイドとイオ
ン結合する酸性モノマーとしては結合力の強いスルホン
酸含有モノマーが良く、スチレンスルホン酸、２−アク
リルアマイド−２−メチル−プロパンスルホン
本発明はポリヘキサメチレンビグアナイド塩を用い洗濯
耐久性のあるエマルジョン系繊維用抗菌防臭加工剤を得
るらのであり、安定な加工剤を得るための手段として、
自己乳化型のポリマーにする必要がある。乳化安定用の
モノマーとしてはポリエチレングリコール〈メタ）アク
リレートのアルキルエーテルが用いられ、これは下記式
％式％（２）
（Ｒ＋は水素原子またはメチル基、Ｒ２は炭素数１〜２
のフルキル基、麺は４〜５０の整数を示す）で表わされ
る。In the present invention, the acidic monomer that ionically bonds with polyhexamethylene biguanide is preferably a sulfonic acid-containing monomer with strong bonding strength, such as styrene sulfonic acid, 2-acrylamide-2-methyl-propanesulfone, or polyhexamethylene biguanide salt. We obtained an antibacterial and deodorizing agent for emulsion-based fibers that is durable against washing, and as a means to obtain a stable agent.
It is necessary to make it a self-emulsifying polymer. As a monomer for emulsion stabilization, an alkyl ether of polyethylene glycol (meth)acrylate is used, which is expressed by the following formula % (2) (R+ is a hydrogen atom or a methyl group, R2 is a carbon number of 1 to 2
is a furkyl group, noodles are an integer from 4 to 50).
ポリエチレングリコールの付加モル数ｍは４〜５０であ
り、特にＩＩ＋が２０〜３０のものが望ましい。The number m of added moles of polyethylene glycol is 4 to 50, and those with II+ of 20 to 30 are particularly desirable.
ポリエチレングリコール（〆り）アクリレートのアルキ
ルエーテルの使用量は製品固形分に対して１０〜４０重
量％が望ましい。The amount of alkyl ether of polyethylene glycol acrylate used is preferably 10 to 40% by weight based on the solid content of the product.
本発明においてヒドロキシアルキル（メタ）アクリレー
トとしては式
％式％（３）
（Ｒ３は水素またはメチル基、ｎは２又は３を示す）で
表わされるモノマーが好ましく、特にヒドロキシエチル
アクリレートが望ましい。ヒドロキシアルキル（メタ）
アクリレートの使用量は架橋効果があればよく固形分中
５〜１５重量％が望ましい。In the present invention, the hydroxyalkyl (meth)acrylate is preferably a monomer represented by the formula % (3) (R3 is hydrogen or a methyl group, n is 2 or 3), and hydroxyethyl acrylate is particularly desirable. Hydroxyalkyl (meth)
The amount of acrylate used is preferably 5 to 15% by weight based on the solid content, as long as it has a crosslinking effect.
本発明において重合に際しては粘度調整剤としてイソプ
ロピルアルコール等の連鎖移動効果のあるものを混入し
て重合するのが好ましく、３〜５０重量％、好ましくは
５〜３０重量％添加するのが望ましい。重合開始剤は通
常使用される開始剤はすべて利用でき、特に制限される
ものではないが水溶性であるものが望ましい。In the present invention, during polymerization, it is preferable to mix a viscosity modifier with a chain transfer effect such as isopropyl alcohol, and it is desirable to add 3 to 50% by weight, preferably 5 to 30% by weight. As the polymerization initiator, any commonly used initiator can be used, and there are no particular restrictions on the initiator, but one that is water-soluble is preferable.
本発明は上記で得られたポリヘキサメチレンビグアナイ
ド塩を含有するエマルジョンＰ、ａ維用抗菌防臭加工剤
にも係る。該加工剤においてポリヘキサメチレンビグア
ナイドの含有量は製品固形分中２０〜４０重量％とする
のが好ましい。The present invention also relates to emulsion P, a, an antibacterial and deodorizing agent for textiles containing the polyhexamethylene biguanide salt obtained above. The content of polyhexamethylene biguanide in the processing agent is preferably 20 to 40% by weight based on the solid content of the product.
本発明のポリヘキサメチレンビグアナイド塩はあらゆる
ａ継に対して抗菌防臭加工剤として使用できる６例えば
綿、ポリエステル／綿、ポリエステル、アクリル、ナイ
ロン等の繊維に通常の方法で適用される。即ち、連続処
理、浸漬処理、スプレー処理等の任意の方法を選択でき
る。本発明塩の好適な使用濃度は、被処理職維に対し０
．１〜２％ｏｗｆが適当であり、０．１％未満では、抗
菌性能に関して不足であり２％を越すとコスト面で高く
なワ実用性にかける。又洗濯耐久性を向上するには他の
樹脂等を併用することも任意である。The polyhexamethylene biguanide salts of the present invention can be used as antibacterial and deodorizing agents for all A-type fibers, such as cotton, polyester/cotton, polyester, acrylic, nylon, etc., in a conventional manner. That is, any method such as continuous treatment, immersion treatment, spray treatment, etc. can be selected. The preferred concentration of the salt of the present invention is 0 for the fiber to be treated.
．． 1 to 2% OWF is appropriate; less than 0.1% is insufficient in terms of antibacterial performance, and more than 2% is expensive and impractical. Further, in order to improve washing durability, it is optional to use other resins in combination.
（実 施 例）
以下に本発明エマルジョンの製造例、本発明の繊維用抗
菌防臭加工剤の抗菌性を測定する試験例を示す。(Example) Examples of manufacturing the emulsion of the present invention and test examples for measuring the antibacterial properties of the antibacterial and deodorizing agent for textiles of the present invention are shown below.
製造例１
ポリヘキサメチレンビグアナイド塩酸塩２０％溶液２７
０部に４０％ＮａＯＨ溶液２５部を加え８を件するとポ
リヘキサメチレンビグアナイドが不溶化し、析出する。Production Example 1 Polyhexamethylene biguanide hydrochloride 20% solution 27
When 25 parts of a 40% NaOH solution was added to 0 parts and the process was repeated in step 8, polyhexamethylene biguanide was insolubilized and precipitated.
このポリマーを取り出し水２７０部を加え、２−アクリ
ルアミド−２−メチルプロパンスルホン酸３６部を加え
て中和すると、水に溶解して透明な溶液１こなる。これ
にメトキシポリエチレングリコールメタクリレート（分
子ｆｆ１１０００）４：３ｇ、ヒドロキシエチルアクリ
レート１５部、インプロパノール３５部を加え、窒素気
流下６０〜７０°Ｃに加温し過硫酸アンモニウム４％水
溶液１０部を５回に分けて３０分毎に加えて重合させた
のち、８０℃で４時間攪拌して重合を完結させる。重合
開始前は透明液体であるが重合が進むにつれエマルジョ
ン化する０重合終了後、水１２９部を加えると固形分約
２５％の安定す白色のエマル７ョンが得られた。このエ
マルジョンの粘度（Ｂ型粘度計、２５℃、以下同様）は
１０００ｃｐｓであった。This polymer was taken out, 270 parts of water was added thereto, and 36 parts of 2-acrylamido-2-methylpropanesulfonic acid was added to neutralize the polymer, which dissolved in water to form one transparent solution. To this was added 4:3 g of methoxypolyethylene glycol methacrylate (molecule FF11000), 15 parts of hydroxyethyl acrylate, and 35 parts of impropanol, heated to 60-70°C under a nitrogen stream, and added 10 parts of a 4% ammonium persulfate aqueous solution 5 times. The mixture was added in portions every 30 minutes for polymerization, and then stirred at 80° C. for 4 hours to complete the polymerization. Before the start of polymerization, it was a transparent liquid, but as the polymerization proceeded, it turned into an emulsion.After the polymerization was completed, 129 parts of water was added, and a stable white emulsion with a solid content of about 25% was obtained. The viscosity of this emulsion (B-type viscometer, 25° C., hereinafter the same) was 1000 cps.
製造例２
メトキシポリエチレングリコールメタクリレート（分子
量約１０００）４３部、２−アクリルアミド−２−メチ
ルプロパンスルホン酸３６１１Ｓ、 ２−１：、 ）’
ロキシエチルアクリレート１５部をインプロパ／−ル３
５部、水２７０部の混合溶媒に溶解し窒素気流下６０℃
〜７０℃に加熱溶解した。過硫酸アンモニウム４％水溶
液１０ｇを５回に分けて３０分毎に加えて重合させた後
、８０℃で４時間撹拌して重合を完結させた後冷却し、
水１２９部を添加、する。これと別にポリヘキサメチレ
ンビグアナイド塩酸塩２０％水溶液２７０部に苛性ソー
ダ４０％溶液２５部を加え沈殿した塩基性ポリヘキサメ
チレンビグアナイドを重合したポリマー中に撹拌しなが
ら添加すると安定な白色のエマル７ョンが得られた。こ
のエマル７ョンの粘度は９００ｅｐｓであった。Production Example 2 43 parts of methoxypolyethylene glycol methacrylate (molecular weight approximately 1000), 2-acrylamido-2-methylpropanesulfonic acid 3611S, 2-1:, )'
15 parts of loxethyl acrylate to 3 parts of inpropar/-
Dissolved in a mixed solvent of 5 parts and 270 parts of water and heated at 60°C under a nitrogen stream.
The mixture was heated and dissolved at ~70°C. After polymerizing by adding 10 g of 4% ammonium persulfate aqueous solution in 5 portions every 30 minutes, the mixture was stirred at 80°C for 4 hours to complete the polymerization, and then cooled.
Add 129 parts of water. Separately, 25 parts of a 40% solution of caustic soda was added to 270 parts of a 20% aqueous solution of polyhexamethylene biguanide hydrochloride, and the precipitated basic polyhexamethylene biguanide was added to the polymerized polymer with stirring to form a stable white emulsion. was gotten. The viscosity of this emulsion was 900 eps.
製造例３
メトキシポリエチレングリコールメタクリレート（分子
量約１０００）４３部、２−アクリル７ミド一２＝メチ
ルプロパンスルホン酸３６部、２−ヒドロキシエチルア
クリレート１５部をインプロパノール３５部、水３００
部の混合溶媒に溶解し窒素式流下６０℃〜７０℃に加熱
溶解した。過硫酸アンモニウム４％水溶液１０部を５回
に分けて３０分毎に加えて重合させた後、８０℃で４時
間撹拌して重合を完結させた後冷却する。このポリマー
をアンモニアで中和した後、ポリへキサメチレンピグア
ナイド塩酸塩２０％水溶ｌ ２７０ｇを重合したポリマ
ー中に撹拌しながら加えると固形分２０％の安定な白色
のエマル７ョンが得られた。このエマルジョンの粘度は
５００ｃｐＳであった。Production Example 3 43 parts of methoxypolyethylene glycol methacrylate (molecular weight approximately 1000), 36 parts of 2-acrylic 7mido-2-methylpropanesulfonic acid, 15 parts of 2-hydroxyethyl acrylate, 35 parts of inpropanol, and 300 parts of water.
The mixture was dissolved in a mixed solvent of 100 ml and heated to 60° C. to 70° C. under a nitrogen atmosphere. 10 parts of a 4% ammonium persulfate aqueous solution was added in 5 portions every 30 minutes for polymerization, and the mixture was stirred at 80° C. for 4 hours to complete the polymerization, followed by cooling. After neutralizing this polymer with ammonia, 270 g of polyhexamethylene piguanide hydrochloride 20% aqueous solution was added to the polymerized polymer with stirring to obtain a stable white emulsion with a solid content of 20%. It was done. The viscosity of this emulsion was 500 cpS.
本発明の抗菌防臭剤のｗＬｍに対する抗菌性を確認する
ため、以下の条件で抗菌性の測定及び洗濯を行った。In order to confirm the antibacterial properties of the antibacterial deodorant of the present invention against wLm, antibacterial properties were measured and washed under the following conditions.
（１）抗菌性の測定
供試試料を黄色ブドウ状球菌を植種した寒天培地上に１
．０％濃度におき、３７°Ｃで２４時時間的培養を行い
、試料周辺の黄色ブドウ状球菌の成育の有無により抗菌
効果を判定した。判定はハローの大きさにより行った。(1) Antibacterial measurement test sample was placed on an agar medium inoculated with Staphylococcus aureus.
．． At a concentration of 0%, culture was performed for 24 hours at 37°C, and the antibacterial effect was determined by the presence or absence of growth of Staphylococcus aureus around the sample. Judgment was made based on the size of the halo.
（２）洗濯方法
家庭洗濯機にてニュービーズ０．２％濃度で４０℃に保
ちながら５分間洗濯し、オーバー７０−にてすすぎを５
分間行い、乾燥することを洗濯回数１回として、繰り返
し洗濯は上記操作を繰Ｉ）返すことにより実施する。(2) Washing method: Wash in a home washing machine with New Beads at a concentration of 0.2% for 5 minutes at 40°C, then rinse at 70°C for 5 minutes.
Repeated washing is carried out by repeating the above operation (I), with washing for 1 minute and drying as one washing cycle.
結果を第１表に示す。表において例えばＬ−１０は洗濯
回数１０回を示す。The results are shown in Table 1. In the table, for example, L-10 indicates the number of washings 10 times.
第１表 （ポリエステル／綿：６５／３５）出 願
人Table 1 (Polyester/Cotton: 65/35) Application
Man
Claims (3)
塩と （ｂ）スルホン酸基を有するモノマーをイオン結合させ
たのち、 （ｃ）ポリエチレングリコール（メタ）アクリレートの
アルキルエーテル及び （ｄ）ヒドロキシアルキル（メタ）アクリレートを共重
合させることを特徴とする水に不溶なポリヘキサメチレ
ンビグアナイド塩を含有するエマルジョンの製法。(1) After (a) polyhexamethylene biguanide or its salt and (b) a monomer having a sulfonic acid group are ionically bonded, (c) an alkyl ether of polyethylene glycol (meth)acrylate and (d) hydroxyalkyl (meth) ) A method for producing an emulsion containing a water-insoluble polyhexamethylene biguanide salt, characterized by copolymerizing an acrylate.
アルキルエーテル及び （ｄ）ヒドロキシアルキル（メタ）アクリレートを共重
合させたのち、 （ａ）ポリヘキサメチレンビグアナイド又はその塩を反
応させることを特徴とする水に不溶なポリヘキサメチレ
ンビグアナイド塩を含有するエマルジョンの製法。(2) After copolymerizing (b) a monomer having a sulfonic acid group, (c) alkyl ether of polyethylene glycol (meth)acrylate, and (d) hydroxyalkyl (meth)acrylate, (a) polyhexamethylene biguanide or A method for producing an emulsion containing a water-insoluble polyhexamethylene biguanide salt, which comprises reacting the salt.
グアナイド塩を含有するエマルジョンを用いたエマルジ
ョン系繊維用抗菌防臭加工剤。(3) An antibacterial and deodorizing agent for emulsion-based fibers using an emulsion containing the polyhexamethylene biguanide salt obtained in claim 1 or 2.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1175030A JPH0339310A (en) | 1989-07-05 | 1989-07-05 | Production of emulsion containing polyhexamethylenebiguanide salt and antimicrobial, deodorizing processing agent containing same emulsion |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1175030A JPH0339310A (en) | 1989-07-05 | 1989-07-05 | Production of emulsion containing polyhexamethylenebiguanide salt and antimicrobial, deodorizing processing agent containing same emulsion |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH0339310A true JPH0339310A (en) | 1991-02-20 |
Family
ID=15988992
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1175030A Pending JPH0339310A (en) | 1989-07-05 | 1989-07-05 | Production of emulsion containing polyhexamethylenebiguanide salt and antimicrobial, deodorizing processing agent containing same emulsion |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0339310A (en) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2349644A (en) * | 1999-05-01 | 2000-11-08 | Biointeractions Ltd | Infection resistant polymers, methods for their preparation, and their uses |
| US6646861B1 (en) | 2000-03-31 | 2003-11-11 | Hitachi, Ltd. | Gas insulated switchgear |
| WO2004100664A1 (en) | 2003-05-15 | 2004-11-25 | Arch Uk Biocides Limited | Composition comprising an acidic copolymer and an antimicrobial agent and use thereof |
| US20100249249A1 (en) * | 2007-12-03 | 2010-09-30 | Stefan Stumpe | Reduction of the Formation of Biofilm by Means of Multifunctional Copolymers |
| EP1624754B1 (en) * | 2003-05-15 | 2011-02-09 | Arch UK Biocides Limited | Antimicrobial composition containing a polymeric biguanide and a copolymer and use thereof |
| US8603453B2 (en) | 2003-05-20 | 2013-12-10 | Arch Uk Biocides Limited | Antimicrobial polymeric biguanide and acidic co-polymer composition and method of use |
-
1989
- 1989-07-05 JP JP1175030A patent/JPH0339310A/en active Pending
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2349644A (en) * | 1999-05-01 | 2000-11-08 | Biointeractions Ltd | Infection resistant polymers, methods for their preparation, and their uses |
| JP2002542847A (en) * | 1999-05-01 | 2002-12-17 | バイオインターラクションズ リミテッド | Infection resistant polymers and their preparation and use |
| US7771743B1 (en) | 1999-05-01 | 2010-08-10 | Biointeractions, Ltd. | Infection resistant polymers, their preparation and uses |
| US6646861B1 (en) | 2000-03-31 | 2003-11-11 | Hitachi, Ltd. | Gas insulated switchgear |
| WO2004100664A1 (en) | 2003-05-15 | 2004-11-25 | Arch Uk Biocides Limited | Composition comprising an acidic copolymer and an antimicrobial agent and use thereof |
| EP1624755A1 (en) * | 2003-05-15 | 2006-02-15 | Arch UK Biocides Limited | Composition comprising an acidic copolymer and an antimicrobial agent and use thereof |
| JP2006528232A (en) * | 2003-05-15 | 2006-12-14 | アーチ ユーケイ バイオサイドズ リミテッド | Composition comprising acid copolymer and antimicrobial agent and use thereof |
| EP1624754B1 (en) * | 2003-05-15 | 2011-02-09 | Arch UK Biocides Limited | Antimicrobial composition containing a polymeric biguanide and a copolymer and use thereof |
| JP4857111B2 (en) * | 2003-05-15 | 2012-01-18 | アーチ ユーケイ バイオサイドズ リミテッド | Composition comprising acid copolymer and antimicrobial agent and use thereof |
| US8603453B2 (en) | 2003-05-20 | 2013-12-10 | Arch Uk Biocides Limited | Antimicrobial polymeric biguanide and acidic co-polymer composition and method of use |
| US20100249249A1 (en) * | 2007-12-03 | 2010-09-30 | Stefan Stumpe | Reduction of the Formation of Biofilm by Means of Multifunctional Copolymers |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| GB2081725A (en) | A Process for the Production of a Hydrogel | |
| JPH0270705A (en) | Manufacture of polymer | |
| GB2104091A (en) | Detergent composition | |
| CN101643531A (en) | Poly N-vinyl pyrrolidone-contained amphiphilic copolymer grafted by natural high polymer or water-solubility derivative thereof and preparation method thereof | |
| CN102559409A (en) | Polymers for high-surfactant formulations | |
| RU2141491C1 (en) | Antiseptic textile material and method of antiseptic protection of solid substrate | |
| JP3259143B2 (en) | Method for producing water absorbent resin | |
| DE4221863C2 (en) | Copolymers of allyliminodiacetic acid with unsaturated carboxylic acids and their use as complexing agents, peroxide stabilizers, builders in detergents and cleaners and dispersants | |
| JPH0339310A (en) | Production of emulsion containing polyhexamethylenebiguanide salt and antimicrobial, deodorizing processing agent containing same emulsion | |
| JP4146900B2 (en) | Water-soluble polymers and their use in cosmetics | |
| DE69311867T2 (en) | Process for the preparation of crosslinked polymers containing carboxyl groups | |
| JPS6213361B2 (en) | ||
| JPH0469601B2 (en) | ||
| JPH0616738A (en) | Method for grafting vinyl monomer onto polyvinyl alcohol | |
| JP3194241B2 (en) | Method for modifying cellulose fiber | |
| JP4896300B2 (en) | Method for producing (meth) acrylic acid (co) polymer | |
| CN115725803B (en) | pH-responsive amphoteric polymer, intermediate and leather fatliquor containing the polymer | |
| JPS5941656B2 (en) | Method for imparting anticoagulant properties to regenerated cellulose | |
| JPH039927B2 (en) | ||
| JPS61130318A (en) | Diallylamine polymer, its production and dye fixing agent containing the same | |
| JPH02248410A (en) | Production of amphoteric copolymer | |
| EP0637328B1 (en) | Polyetheramidoamine superabsorbent hydrogels | |
| JPS61133213A (en) | Diallylamine copolymer, production thereof and color fastness enhancer containing same | |
| JP2669519B2 (en) | Darkening agent | |
| JPS6189208A (en) | Polyvinyl alcohol macromonomer, and graft copolymer prepared therewith |