JP2006348118A - Polyvinylpyrrolidone-iodine complex - Google Patents
Polyvinylpyrrolidone-iodine complex Download PDFInfo
- Publication number
- JP2006348118A JP2006348118A JP2005174310A JP2005174310A JP2006348118A JP 2006348118 A JP2006348118 A JP 2006348118A JP 2005174310 A JP2005174310 A JP 2005174310A JP 2005174310 A JP2005174310 A JP 2005174310A JP 2006348118 A JP2006348118 A JP 2006348118A
- Authority
- JP
- Japan
- Prior art keywords
- polyvinylpyrrolidone
- iodine
- parts
- iodine complex
- dimethylmethane
- 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
- 229920000153 Povidone-iodine Polymers 0.000 title claims abstract description 14
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims abstract description 25
- 229920000036 polyvinylpyrrolidone Polymers 0.000 claims abstract description 21
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 claims abstract description 21
- 239000001267 polyvinylpyrrolidone Substances 0.000 claims abstract description 19
- 239000002131 composite material Substances 0.000 claims description 3
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 22
- 229910052740 iodine Inorganic materials 0.000 description 22
- 239000011630 iodine Substances 0.000 description 22
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 7
- CPKVUHPKYQGHMW-UHFFFAOYSA-N 1-ethenylpyrrolidin-2-one;molecular iodine Chemical compound II.C=CN1CCCC1=O CPKVUHPKYQGHMW-UHFFFAOYSA-N 0.000 description 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 230000000844 anti-bacterial effect Effects 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 210000000214 mouth Anatomy 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 238000001694 spray drying Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 230000003915 cell function Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229910000365 copper sulfate Inorganic materials 0.000 description 1
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 229910000043 hydrogen iodide Inorganic materials 0.000 description 1
- 239000008311 hydrophilic ointment Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 150000001451 organic peroxides Chemical group 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical group O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
Landscapes
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
Description
本発明は、ポリビニルピロリドン−ヨウ素複合体に関する。 The present invention relates to a polyvinylpyrrolidone-iodine complex.
ポリビニルピロリドン−ヨウ素複合体（ポピドンヨード）は、ポリビニルピロリドン（以下ＰＶＰともいう）とヨウ素との複合体であり、遊離のヨウ素（Ｉ２）の酸化作用による細胞機能阻害により殺菌作用等が発揮される。ＰＶＰ−ヨウ素複合体は、水溶液や親水性軟膏として、手指、皮膚、手術部位、並びに口腔内に対して殺菌作用を期待して使用されており、貯蔵時に有効ヨウ素をなるべく損失しないこと、すなわちできるだけ安定であることが要求されている。 A polyvinylpyrrolidone-iodine complex (popidone iodine) is a complex of polyvinylpyrrolidone (hereinafter also referred to as PVP) and iodine, and exhibits a bactericidal action or the like due to cell function inhibition due to the oxidizing action of free iodine (I 2 ). . The PVP-iodine complex is used as an aqueous solution or hydrophilic ointment with the expectation of bactericidal action on the fingers, skin, surgical site, and oral cavity, and should not lose effective iodine as much as possible during storage. It is required to be stable.
安定なＰＶＰ−ヨウ素複合体を得るためには、従来より種々の提案がなされており、例としては、特定の水分を含有するＰＶＰを用いること（米国特許第２９００３０５号公報）、重炭酸ナトリウムを添加すること（米国特許第２８２６５３２号公報）、ヨウ化水素又はヨウ化アルカリの形のヨウ化物を添加すること（米国特許第３８９８３２６号公報）、ギ酸又はシュウ酸あるいはそのアンモニウム塩又はアミドを添加すること（ドイツ特許第２９４２１７９号公報、特開昭５６−６５００６号公報）等が挙げられる。
しかし、これらの従来技術には、製造工程で水分調整や添加物の添加といった余分な工程を要し、製造が困難であるという問題や、安定性が不十分であるという問題があった。本発明はこの問題に鑑みて、比較的容易に製造でき、安定性に優れたＰＶＰ−ヨウ素複合体を提供することを目的とする。 However, these conventional techniques require extra steps such as moisture adjustment and addition of additives in the production process, and thus there are problems that the production is difficult and that the stability is insufficient. In view of this problem, an object of the present invention is to provide a PVP-iodine composite that can be produced relatively easily and has excellent stability.
本発明のポリビニルピロリドン−ヨウ素複合体は、上記の課題を解決するために、ポリビニルピロリドンの末端が１−ヒドロキシ−１，１−ジメチルメタンであるものとする（請求項１）。 In the polyvinylpyrrolidone-iodine complex of the present invention, the end of polyvinylpyrrolidone is 1-hydroxy-1,1-dimethylmethane in order to solve the above problems (claim 1).
上記において１−ヒドロキシ−１，１−ジメチルメタン末端の含有率は、ポリビニルピロリドン１モルに対して０．１〜２．０モルであることが好ましい（請求項２）。 In the above, the content of 1-hydroxy-1,1-dimethylmethane terminal is preferably 0.1 to 2.0 mol with respect to 1 mol of polyvinylpyrrolidone (Claim 2).
また、上記ポリビニルピロリドンのＫ値は１０〜３５であることが好ましい（請求項３）。 The polyvinyl pyrrolidone preferably has a K value of 10 to 35 (claim 3).
本発明によれば、ヨウ素安定性に優れたポリビニルピロリドン−ヨウ素複合体が得られる。すなわち、添加物等を使用せずに保存安定性に優れたポピドンヨード製品が得られる。 According to the present invention, a polyvinylpyrrolidone-iodine complex having excellent iodine stability can be obtained. That is, a popidone iodine product having excellent storage stability can be obtained without using additives.
本発明のポリビニルピロリドン−ヨウ素複合体は、１−ヒドロキシ−１，１−ジメチルメタン末端の導入方法には依らないが、例えばイソプロパノールのような有機溶剤の中でラジカル形成体としての有機過酸化物、例えばジアルキルパーオキサイドを使用して重合を行うことによって製造される末端が１−ヒドロキシ−１，１−ジメチルメタンであるポリビニルピロリドンに元素のヨウ素を反応させることで得られる。 The polyvinylpyrrolidone-iodine complex of the present invention does not depend on the method for introducing 1-hydroxy-1,1-dimethylmethane end, but is an organic peroxide as a radical former in an organic solvent such as isopropanol. For example, it can be obtained by reacting elemental iodine with polyvinylpyrrolidone whose terminal is 1-hydroxy-1,1-dimethylmethane produced by polymerization using dialkyl peroxide.
本発明のポリビニルピロリドン−ヨウ素複合体における１−ヒドロキシ−１，１−ジメチルメタン末端の含有率は、ポリビニルピロリドン１モルに対して０．１〜２．０モルであることが好ましく、０．２〜１．１モルであることがより好ましい。この含有率が０．１未満であるとヨウ素安定性が低下する傾向がある。この含有率は、例えば上記複合体の製造の際の、イソプロパノールのような有機溶剤とビニルピロリドンとの仕込み比を変えることによって調整することができる。 The content of 1-hydroxy-1,1-dimethylmethane terminal in the polyvinylpyrrolidone-iodine complex of the present invention is preferably 0.1 to 2.0 mol with respect to 1 mol of polyvinylpyrrolidone, 0.2 More preferably, it is -1.1 mol. If this content is less than 0.1, iodine stability tends to decrease. This content can be adjusted, for example, by changing the charging ratio between an organic solvent such as isopropanol and vinylpyrrolidone in the production of the composite.
また、上記ポリビニルピロリドンのＫ値は１０〜３５であることが好ましく、１５〜３３であることがより好ましい。Ｋ値とは、ドイツの化学者フィケンチャーにより提案された重合度を表わす定数（ツェルローゼヘミー１３巻５８〜６４頁、７１〜７４頁（１９３２年）参照）であり、Ｋ値が１０未満であるとヨウ素安定性が低下する傾向があり、３５を超えると粘性が高く扱いにくくなる傾向がある。 The polyvinyl pyrrolidone has a K value of preferably 10 to 35, more preferably 15 to 33. K value is a constant representing the degree of polymerization proposed by German chemist Fikencher (see Zellrose Hemy 13: 58-64, 71-74 (1932)), and the K value is less than 10. When it exists, there exists a tendency for iodine stability to fall, and when it exceeds 35, there exists a tendency for viscosity to become high and to become difficult to handle.
ヨウ素安定性は、ＰＶＰ−ヨウ素複合体がその調製物、特に水溶液において貯蔵時にどの程度のヨウ素損失を起こすかで示され、ヨウ素損失が３％以下であれば安定性良好と判断できる。 Iodine stability is indicated by how much iodine loss occurs during storage of the PVP-iodine complex in the preparation, particularly in an aqueous solution, and it can be judged that the stability is good if the iodine loss is 3% or less.
以下、本発明の実施例を説明するが、本発明は以下の実施例によって限定されるものではない。なお、以下において、「部」及び「％」は重量基準である。 Examples of the present invention will be described below, but the present invention is not limited to the following examples. In the following, “parts” and “%” are based on weight.
［製造例１］
耐圧攪拌容器中にイソプロパノール８０部及びビニルピロリドン３５０部、イソプロパノール７０部、及びジ三級ブチルパーオキサイド１．７５部からなる混合物のうち４０部を予め装入して１２０℃に加熱した。残りの混合物を３時間かけて添加し、単量体ビニルピロリドン含量が０．５％以下になるまで３時間加熱を続けた。反応後、水蒸気の導入によりイソプロパノールを留去して水溶液とした後、噴霧乾燥により粉末状ポリビニルピロリドンを得た。
[Production Example 1]
40 parts of a mixture consisting of 80 parts of isopropanol, 350 parts of vinylpyrrolidone, 70 parts of isopropanol and 1.75 parts of di-tert-butyl peroxide was charged in advance in a pressure-resistant stirring vessel and heated to 120 ° C. The remaining mixture was added over 3 hours and heating was continued for 3 hours until the monomeric vinylpyrrolidone content was below 0.5%. After the reaction, isopropanol was distilled off by introduction of water vapor to obtain an aqueous solution, and then powdered polyvinylpyrrolidone was obtained by spray drying.
［製造例２］
イソプロパノール８０部に代えて６５部を用いた以外は、実施例１と同様にして粉末状ポリビニルピロリドンを得た。
[Production Example 2]
Powdered polyvinyl pyrrolidone was obtained in the same manner as in Example 1 except that 65 parts were used instead of 80 parts of isopropanol.
［製造例３］
イソプロパノール８０部に代えて２００部を用いた以外は、実施例１と同様にして粉末状ポリビニルピロリドンを得た。
[Production Example 3]
Powdered polyvinyl pyrrolidone was obtained in the same manner as in Example 1 except that 200 parts were used instead of 80 parts of isopropanol.
［比較製造例］
攪拌容器中で水７００部及びビニルピロリドン３００部を混合し、０．０１％硫酸銅水溶液２．３部、３０％過酸化水素水９部を添加し、重合を開始した。重合中はｐＨを７以上に調製した。３時間反応させた後、さらに３０％過酸化水素水０．５部を添加し、単量体ビニルピロリドン含量を低下させた後、噴霧乾燥により粉末状ポリビニルピロリドンを得た。
[Comparative manufacturing example]
In a stirring vessel, 700 parts of water and 300 parts of vinylpyrrolidone were mixed, 2.3 parts of 0.01% aqueous copper sulfate solution and 9 parts of 30% aqueous hydrogen peroxide were added, and polymerization was started. During the polymerization, the pH was adjusted to 7 or higher. After reacting for 3 hours, 0.5 part of 30% hydrogen peroxide was further added to lower the monomer vinylpyrrolidone content, and then powdered polyvinylpyrrolidone was obtained by spray drying.
［実施例１〜３、比較例］
上記により得られたポリビニルピロリドンにつき、以下の方法で１−ヒドロキシ−１，１−ジメチルメタン末端の含有率及びＫ値を測定し、さらにポリビニルピロリドン−ヨウ素複合体を調製してそのヨウ素損失・ヨウ素安定の評価を行った。結果を表１に示す。
[Examples 1 to 3, Comparative Example]
With respect to the polyvinylpyrrolidone obtained as described above, the content and K value of 1-hydroxy-1,1-dimethylmethane terminal are measured by the following method, and a polyvinylpyrrolidone-iodine complex is further prepared to obtain iodine loss / iodine. Evaluation of stability was performed. The results are shown in Table 1.
［１−ヒドロキシ−１，１−ジメチルメタン末端の含有率］
１Ｈ−ＮＭＲ測定におけるピロリドン環由来のシグナル積分値と、１−ヒドロキシ−１，１−ジメチルメタン末端由来のシグナル積分値の比率と、ＧＰＣ法による平均分子量から算出した。
[Content of 1-hydroxy-1,1-dimethylmethane terminal]
It calculated from the ratio of the signal integral value derived from the pyrrolidone ring in 1 H-NMR measurement, the signal integral value derived from 1-hydroxy-1,1-dimethylmethane terminal, and the average molecular weight by GPC method.
［Ｋ値］
ツェルローゼヘミー１３巻５８〜６４頁、７１〜７４頁に記載のフィケンチャーの方法により測定した。
[K value]
It was measured by the method of the fixture described in Zellrose Chemie Vol. 13, pages 58-64, pages 71-74.
［ヨウ素損失・ヨウ素安定性］
粉末状ポリビニルピロリドン８３重量部と粉砕したヨウ素１７重量部を揺動式混合機中で６時間室温で混合し、続いて９５℃で１５時間熱処理した。得られたポリビニルピロリドン−ヨウ素複合体を試料とし、有効ヨウ素含量が１％の水溶液を８０℃で１５時間貯蔵した場合の有効ヨウ素の変化量からヨウ素損失を算出した。有効ヨウ素量の測定はチオ硫酸ナトリウムによる滴定にて行った。
[Iodine loss / iodine stability]
83 parts by weight of powdered polyvinylpyrrolidone and 17 parts by weight of pulverized iodine were mixed in a rocking mixer for 6 hours at room temperature, followed by heat treatment at 95 ° C. for 15 hours. The obtained polyvinylpyrrolidone-iodine complex was used as a sample, and iodine loss was calculated from the amount of change in effective iodine when an aqueous solution having an effective iodine content of 1% was stored at 80 ° C. for 15 hours. The effective iodine amount was measured by titration with sodium thiosulfate.
ヨウ素損失が３％以下の場合、ヨウ素安定を「○」と評価し、３％を超える場合、「×」と評価した。 When iodine loss was 3% or less, iodine stability was evaluated as “◯”, and when it exceeded 3%, it was evaluated as “x”.
本発明のポリビニルピロリドン−ヨウ素複合体は、手指、皮膚、手術部位、口腔内の殺菌用途等に用いられる。
The polyvinylpyrrolidone-iodine complex of the present invention is used for sterilization of fingers, skin, surgical site, oral cavity, and the like.
Claims (3)
ポリビニルピロリドンの末端が１−ヒドロキシ−１，１−ジメチルメタンである
ことを特徴とする、ポリビニルピロリドン−ヨウ素複合体。 A composite composed of polyvinylpyrrolidone and iodine,
The end of polyvinylpyrrolidone is 1-hydroxy-1,1-dimethylmethane. Polyvinylpyrrolidone-iodine complex characterized by the above-mentioned.
The polyvinyl pyrrolidone-iodine complex according to claim 1 or 2, wherein the polyvinyl pyrrolidone has a K value of 10 to 35.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2005174310A JP2006348118A (en) | 2005-06-14 | 2005-06-14 | Polyvinylpyrrolidone-iodine complex |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2005174310A JP2006348118A (en) | 2005-06-14 | 2005-06-14 | Polyvinylpyrrolidone-iodine complex |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JP2006348118A true JP2006348118A (en) | 2006-12-28 |
Family
ID=37644296
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2005174310A Pending JP2006348118A (en) | 2005-06-14 | 2005-06-14 | Polyvinylpyrrolidone-iodine complex |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2006348118A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102643377A (en) * | 2012-05-10 | 2012-08-22 | 上海宇昂生物科技有限公司 | Preparation method of homopolymerized N-vinyl butyl lactam iodine with 20% of effective iodine content |
| WO2017193326A1 (en) * | 2016-05-12 | 2017-11-16 | Boai Nky Pharmaceuticals Ltd. | Degradable vinylpyrrolidone homopolymers and copolymers and methods for preparing the same |
-
2005
- 2005-06-14 JP JP2005174310A patent/JP2006348118A/en active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102643377A (en) * | 2012-05-10 | 2012-08-22 | 上海宇昂生物科技有限公司 | Preparation method of homopolymerized N-vinyl butyl lactam iodine with 20% of effective iodine content |
| WO2017193326A1 (en) * | 2016-05-12 | 2017-11-16 | Boai Nky Pharmaceuticals Ltd. | Degradable vinylpyrrolidone homopolymers and copolymers and methods for preparing the same |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US5296239A (en) | Peracetic acid compositions and process for obtaining these compositions | |
| DK156983B (en) | PROCEDURE FOR THE PREPARATION OF A GERMICID ORGANIC IODOPHORIAN COMPOSITION | |
| JP3399874B2 (en) | Detergent builder, method for producing the same, poly (meth) acrylic acid (salt) polymer and use | |
| WO1989000006A1 (en) | Biocidal composition | |
| JP2006348118A (en) | Polyvinylpyrrolidone-iodine complex | |
| JP2007070303A (en) | METHOD FOR PRODUCING alpha-LIPOIC ACID ALKALI SALT | |
| US7824503B2 (en) | Aqueous hydrogen peroxide-containing composition and its use for cleaning surfaces | |
| CN102125053B (en) | High-stability non-ionic N-vinyl butyrate lactam iodine solution and related preparation method | |
| EP2187862B1 (en) | Tooth-bleaching preparations | |
| CN113729033A (en) | Chlorine-containing disinfectant with high thermal stability and preparation method thereof | |
| US4732617A (en) | Fluoride-containing compositions | |
| JP2853254B2 (en) | Chlorotrifluoroethylene / perfluoro (alkyl vinyl ether) copolymer | |
| JP2991987B2 (en) | Basic aluminum chloride and method for producing the same | |
| WO2014151439A1 (en) | Itaconic acid polymers for oral care applications | |
| JPH10510873A (en) | Stable aqueous stock solution of copolymer of crosslinked low alkyl vinyl ether and maleic anhydride. | |
| CN116267919B (en) | Potassium hydrogen persulfate compound powder and preparation method thereof | |
| WO1993019727A1 (en) | Toothpaste composition | |
| JPH04224518A (en) | Novel antibacterial composition and method of its preparation | |
| JP4412428B2 (en) | Peracetic acid composition | |
| CN1443061A (en) | Oral composition | |
| US5158768A (en) | Process for preparing a stable, low K-value, water-soluble PVP-iodine product | |
| JPH0381310A (en) | Dipolar electrolyte hydrophylic polymer, its manufacture and its use as absorbent | |
| JP4330091B2 (en) | Method for producing low viscosity sodium carboxymethylcellulose | |
| JPS63235313A (en) | Preparation of maleic acid copolymer | |
| JP2007084461A (en) | Cosmetic composition |