JPH0288069A - Antibacterial deodorant - Google Patents

Antibacterial deodorant

Info

Publication number
JPH0288069A
JPH0288069A JP63242144A JP24214488A JPH0288069A JP H0288069 A JPH0288069 A JP H0288069A JP 63242144 A JP63242144 A JP 63242144A JP 24214488 A JP24214488 A JP 24214488A JP H0288069 A JPH0288069 A JP H0288069A
Authority
JP
Japan
Prior art keywords
hematin
deodorizing
antibacterial
sulfate
metal
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
Application number
JP63242144A
Other languages
Japanese (ja)
Inventor
Masahiro Takatani
高谷 昌弘
Setsuo Tsuruoka
鶴岡 節雄
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Hamari Chemicals Ltd
Original Assignee
Hamari Chemicals Ltd
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Hamari Chemicals Ltd filed Critical Hamari Chemicals Ltd
Priority to JP63242144A priority Critical patent/JPH0288069A/en
Publication of JPH0288069A publication Critical patent/JPH0288069A/en
Pending legal-status Critical Current

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  • Absorbent Articles And Supports Therefor (AREA)
  • Disinfection, Sterilisation Or Deodorisation Of Air (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

(57)【要約】本公報は電子出願前の出願データであるた
め要約のデータは記録されません。
(57) [Abstract] This bulletin contains application data before electronic filing, so abstract data is not recorded.

Description

【発明の詳細な説明】 (産業上の利用分野) 本発明は抗菌効果を有する脱臭剤に関するものである。[Detailed description of the invention] (Industrial application field) The present invention relates to a deodorizing agent having an antibacterial effect.

(従来の技術) 現在知られている脱臭方法には悪臭を芳香剤、活性炭、
ゼオライト、シクロデキストリン等によりマスキング、
吸着、包接させる物理的な脱臭方法と重クロム酸カリウ
ム、過マンガン酸カリウム、硫酸、二酸化塩素、クロロ
フィル、金属ポルフィリン、金属ポルフィラジン等と反
応させる化学的な脱臭方法がある。又、悪臭発生に微生
物が関与している場合は脱臭剤と抗菌剤との混合物がよ
く用いられている。
(Prior art) Currently known deodorizing methods include using air fresheners, activated carbon, and
Masking with zeolite, cyclodextrin, etc.
There are physical deodorizing methods that involve adsorption and inclusion, and chemical deodorizing methods that involve reacting with potassium dichromate, potassium permanganate, sulfuric acid, chlorine dioxide, chlorophyll, metal porphyrin, metal porphyrazine, etc. Furthermore, when microorganisms are involved in the generation of bad odors, a mixture of a deodorizer and an antibacterial agent is often used.

一般に脱臭効率、脱臭持続性等の点から物理的な脱臭方
法より化学的な脱臭方法による脱臭剤の方が優れている
と考えられており、持に取り扱い、安全性、持続性等の
点から酸化還元能を有する金属ポルフィリン、金属ポル
フィラジン(特開昭53−16384.特開昭53−9
4293.特開昭53−133590.特開昭56−6
3355゜特開昭62142565)やクロロフィル等
が実用面において優れていると考えられている。
In general, deodorizers using chemical deodorizing methods are considered to be superior to physical deodorizing methods in terms of deodorizing efficiency, deodorizing sustainability, etc.; Metal porphyrin and metal porphyrazine having redox ability (JP-A-53-16384, JP-A-53-9
4293. Japanese Patent Publication No. 53-133590. Japanese Patent Publication No. 56-6
3355° JP-A-62142565) and chlorophyll are considered to be excellent in practical terms.

ポルフィリン骨格を有するクロロフィリンには静菌作用
があると云われているが、その作用は極めて弱く、例え
ばブドウ状球菌に対する最少発育阻止濃度は4000 
p!/1ttlである( T’、 A、 Nevina
nd B、 G、 Bibby、 J、 Dental
Research、  33 。
It is said that chlorophyllin, which has a porphyrin skeleton, has a bacteriostatic effect, but its effect is extremely weak; for example, the minimum inhibitory concentration against Staphylococcus is 4000.
p! /1ttl (T', A, Nevina
nd B, G, Bibby, J, Dental
Research, 33.

571〜579頁、1654年)。571-579, 1654).

一方、ヘマチンは生体成分として知られているが、従来
その応用はあまり研究されておらず、僅かにラノカス等
がヘマチン銅錯体がチトクロムCの酸化酵素のモデル反
応の酵素としての可能性を検討している程度である( 
E、 Lukas et、 、 J。
On the other hand, although hematin is known as a biological component, its application has not been studied much, and Lanokas et al. investigated the possibility of hematin copper complex as an enzyme for the model reaction of cytochrome C oxidase. (
E., Lukas et., J.

Chem、 Soc、 Dalton Trans、 
、  1982年、1035頁)。
Chem, Soc, Dalton Trans,
, 1982, p. 1035).

(発明が解決しようとする課題) 上記のように、従来優れた脱臭効果を有すると考えられ
ている金属ポルフィリン等においても微生物の関与する
悪臭には作用せず、抗菌剤を別に添加する必要がある。
(Problems to be Solved by the Invention) As mentioned above, even metal porphyrins, etc., which are conventionally thought to have excellent deodorizing effects, do not work against bad odors caused by microorganisms, and it is necessary to separately add an antibacterial agent. be.

例えば消臭作用を葡する鉄フタロシアニン誘導体に殺菌
効果を持つ銀イオンを添加して、足臭分解能を有する脱
臭剤が作成されている(「足臭を酵素で分解」日刊工業
新聞、昭和63年7月2日付記事)。いずれにせよ最近
の様に環境の変化にともない、あらゆる悪臭により効果
のある脱臭剤が強く望まれており、そのためには微生物
の関与する悪臭にも効果のある抗菌作用を何する脱臭剤
が必要となってくる。しかし現在名に安全で、且つ持続
性のある化学的な脱臭剤で優れた抗菌作用を何するもの
は未だ見い出されていない。
For example, a deodorizer with the ability to decompose foot odor has been created by adding silver ions, which have a bactericidal effect, to an iron phthalocyanine derivative that has a deodorizing effect ("Decomposing foot odor with enzymes", Nikkan Kogyo Shimbun, 1988 Article dated July 2). In any case, with the recent changes in the environment, there is a strong demand for deodorizers that are effective against all kinds of bad odors, and for this purpose, there is a need for deodorizers that have antibacterial effects and are also effective against bad odors caused by microorganisms. It becomes. However, at present, no chemical deodorizer that is safe and long-lasting and has excellent antibacterial activity has yet been found.

(課題を解決するための手段) 本発明者らは安全で持続性のある新しい抗菌脱臭剤を見
い出すべく、先ず安全面と云う点から生体成分に着目し
、未だ脱臭作用が検討されていないヘマチン及びその金
属塩につき種々の検討を加えた結果、驚くべき事に優れ
た脱臭効果と共に強力な抗菌作用を有している事を見い
出した。
(Means for Solving the Problems) In order to find a new antibacterial deodorizer that is safe and long-lasting, the present inventors first focused on biological components from the viewpoint of safety, and focused on hematin, whose deodorizing effect has not yet been investigated. As a result of conducting various studies on and its metal salts, it was surprisingly discovered that it has an excellent deodorizing effect as well as a strong antibacterial effect.

ヘマチンもしくはその金属錯体は第1表に示した如くア
ンモニア、トリメチルアミン、硫化水素、メチルメルカ
プタン等の代表的な悪臭分子に対して侵れた脱臭効果を
示した。これ等ヘマチン及びヘマチン金属錯体の脱臭効
果は、これ等が強力な酸化触媒として働き、悪臭分子を
化学的に酸化除去するためと考えられる。
As shown in Table 1, hematin or its metal complex exhibited a strong deodorizing effect against typical malodorous molecules such as ammonia, trimethylamine, hydrogen sulfide, and methyl mercaptan. The deodorizing effect of hematin and hematin metal complexes is thought to be due to the fact that they act as strong oxidation catalysts and chemically oxidize and remove malodorous molecules.

また、ヘマチンもしくはその金属錯体は強力な抗菌作用
を有していることが本発明者らによりはじめて確認され
た。すなわち、第2表に示す如くそれらは黄色ブドウ球
菌や枯草菌に対して12.5ti97mlの低濃度でそ
の発育を阻止することが判った。
Furthermore, the present inventors have confirmed for the first time that hematin or its metal complex has a strong antibacterial effect. That is, as shown in Table 2, they were found to inhibit the growth of Staphylococcus aureus and Bacillus subtilis at a low concentration of 12.5ti97ml.

本発明はこの新知見に基づくもので、ヘマチンもしくは
その金属錯体を含有してなる抗菌脱臭剤である。
The present invention is based on this new knowledge, and is an antibacterial deodorizing agent containing hematin or a metal complex thereof.

ヘマチンはヒトの糞便中に、特に肉食または胃出血のと
きに多くみられ、普通には天然でタンパク買などと複合
体を形成して存在している。通常ヘマチンはヘミンを希
アルカリに溶かし、酢酸等で酸性とし析出する粗ヘマチ
ンをピリジン等から再結晶すると得ることができる。又
その金属錯体はヘマチンの希アルカ、すmHに対応する
金属塩の溶液を添加することにより得ることができる。
Hematin is found in large quantities in human feces, especially when meat is eaten or gastric bleeding occurs, and it normally exists naturally in the form of a complex with proteins. Normally, hematin can be obtained by dissolving hemin in a dilute alkali, acidifying it with acetic acid, etc., and recrystallizing the precipitated crude hematin from pyridine or the like. Alternatively, the metal complex can be obtained by adding a solution of a metal salt corresponding to a dilute alkali of hematin, SumH.

通常使用される金属塩としては硫酸銅、硫酸亜鉛、硫酸
アルミニウム、硫酸アンチモン、硫酸コバルト、硫酸ス
ズ、硫酸鉛、硫酸白金、硫酸ニッケル、硫酸ビスマス、
硫酸マグネシウム、硫酸マンガン、硝酸銅、硝酸亜鉛、
硝酸マグネシウム、塩化第二鉄、燐酸銅、酢酸亜鉛、酢
酸銅、酢酸マグネシウム、乳酸カルシウム、乳酸ニッケ
ル等を挙げることができるが、持にヘマチンと金属錯体
を形成する金属として銅、鉄、マンガン、ニッケル、コ
バルト、マグネシウム、スズ、アルミニウムまたはこれ
らの水酸化金属やハロゲン化金属などが経済性、安全性
等の点から好んで用いられる。しかしこれ等の金属に何
ら限定されることなく、ヘマチンと錯体を形成する金属
塩であればいずれを用いても良い。
Commonly used metal salts include copper sulfate, zinc sulfate, aluminum sulfate, antimony sulfate, cobalt sulfate, tin sulfate, lead sulfate, platinum sulfate, nickel sulfate, bismuth sulfate,
Magnesium sulfate, manganese sulfate, copper nitrate, zinc nitrate,
Magnesium nitrate, ferric chloride, copper phosphate, zinc acetate, copper acetate, magnesium acetate, calcium lactate, nickel lactate, etc. can be mentioned, but copper, iron, manganese, Nickel, cobalt, magnesium, tin, aluminum, or metal hydroxides or metal halides thereof are preferably used from the viewpoint of economy, safety, and the like. However, without being limited to these metals, any metal salt that forms a complex with hematin may be used.

本発明の抗菌脱臭剤はその使用において特に形態を制限
されるものではなく、その効果が発揮される限りいずれ
の形態でもよい。例えば原体のまま使用しても良いが、
必要に応じて水、活性炭、ゼオライト、でんぷん、おが
(ず、シクロデキストリン、発泡スチロール、発泡コン
クリート、発泡樹脂、軽石、各種繊維、ゴム、活性アル
ミナ、シリカゲル、ケイソウ土、カオリン、モレキュラ
シーブ、ベントナイト、二酸化チタン、炭酸マグネシウ
ム、酸化マグネシウム、接着剤、セルロース、ゼラチン
、カゼイン、ガム類、フィルム、パルプ、紙、皮革、布
、木材、鉱物、セロファン、セラミックス、プラスチッ
ク等に溶解、吸着、付着、含浸あるいは化学結合させて
用いることが出来る。
The antibacterial deodorizer of the present invention is not particularly limited in its form in use, and may be in any form as long as its effects are exhibited. For example, it may be used as is, but
Water, activated carbon, zeolite, starch, sawdust, cyclodextrin, styrofoam, foamed concrete, foamed resin, pumice, various fibers, rubber, activated alumina, silica gel, diatomaceous earth, kaolin, molecular sieve, bentonite, dioxide as required. Dissolved, adsorbed, attached, impregnated or chemically applied to titanium, magnesium carbonate, magnesium oxide, adhesives, cellulose, gelatin, casein, gums, films, pulp, paper, leather, cloth, wood, minerals, cellophane, ceramics, plastics, etc. Can be used in combination.

Cれ等素材に吸着、付着、含゛浸あるいは化学結合等さ
れた抗菌脱臭剤は各種用途に応じて多方面にわたり使用
される。例えば、衣料用品、各種フィルター、紙オムツ
、マスク、各種バット、肌着、寝装具、靴下、包装、空
気清浄器、内装材、各種ポリ袋、トイレタリー用品、口
腔用品、ペット用品、冷蔵庫用品、石ケン、洗剤、スリ
ッパ、生理用品、カーペット、シュウタン、軍用品、造
花、たばこパイプ、歯磨、化粧品、病人用シート、綿、
インク、塗料、各種シート、マット、ティシュ、ぬれハ
ンカチ、鮮度保持紙、カーテン、フスマ、障子、香料等
に使用される。
Antibacterial deodorizers that are adsorbed, attached, impregnated, or chemically bonded to materials such as carbon fibers are used in a wide variety of applications depending on the purpose. For example, clothing supplies, various filters, disposable diapers, masks, various bats, underwear, bedding, socks, packaging, air purifiers, interior materials, various plastic bags, toiletry supplies, oral supplies, pet supplies, refrigerator supplies, soap. , detergents, slippers, sanitary products, carpets, toiletries, military supplies, artificial flowers, tobacco pipes, toothpaste, cosmetics, patient sheets, cotton,
Used in ink, paint, various sheets, mats, tissues, wet handkerchiefs, freshness-preserving paper, curtains, bran, shoji screens, fragrances, etc.

本発明の脱臭剤は必要に応じて、この皿の脱臭剤に慣用
される充用剤、結合剤、助剤、着色剤等の補助添加成分
を併用することが出来る。
The deodorizing agent of the present invention may contain, if necessary, auxiliary additive components such as fillers, binders, auxiliary agents, and coloring agents that are commonly used in deodorizing agents for dishes.

(実施例) 次に本発明を具体的に説明するため、実施例を挙げて効
果を示すが、これ等の実施例によって本発明は何ら限定
されるものではない。
(Example) Next, in order to specifically explain the present invention, examples will be given to show the effects, but the present invention is not limited to these examples in any way.

実施例1 ヘマチン1gをクロロホルム100 yttに溶解し、
これを調紙(東洋濾紙嵐2)10gに1%吸着させ、乾
燥したものから1yを取り脱臭剤供試料とした。
Example 1 1 g of hematin was dissolved in 100 ytt of chloroform,
This was adsorbed at 1% on 10 g of paper (Toyo Roshi Arashi 2), and 1y was taken from the dried product and used as a deodorizing agent sample.

実施例2 ヘマチン2註0 5 yxlに溶解後、純水100肩tを加えて希釈した
溶液に、別に水25m1に硝酸銅・3水塩751Fを溶
解した液を加えて充分混合した後、希硝酸でpHを6.
9−70に調整し、析出するヘマチン銅錯体をP取、水
洗機水中に分散させて、これを不織布2gに乾燥後1%
となる様に吸着させ、乾燥したものから11を取り脱臭
剤供試料とした。
Example 2 After dissolving hematin in 0.5 yxl, add 100 tons of pure water to dilute the solution. Separately, add a solution of copper nitrate trihydrate 751F in 25 ml of water and mix thoroughly. Adjust the pH to 6. with nitric acid.
9-70, remove the precipitated hematin copper complex, disperse it in washing machine water, and apply it to 2g of nonwoven fabric at 1% after drying.
11 was taken from the dried product and used as a deodorizing agent sample.

実施例3 ヘマチン200〜を1規定カセイソーダ水溶液5 ml
に溶解後、純水10 0 mlを加えて希釈した溶液に
、別に水25m1に塩化第二鉄・6水塩85#Igを溶
解した液を加えて充分混合した後、希硝酸でpHを5.
 8 − 5. 9に調整し、析出するヘマチン鉄錯体
をP取、水洗機水中に分散させて、これを綿花2yに乾
燥後1%となる様吸着させ、乾燥したものから1gを取
り脱臭剤供試料とした。
Example 3 5 ml of 1N caustic soda aqueous solution of hematin 200~
To the diluted solution by adding 100 ml of pure water, add a solution of 85 #Ig of ferric chloride hexahydrate dissolved in 25 ml of water and mix well, then adjust the pH to 5 with dilute nitric acid. ..
8-5. 9, the precipitated hematin iron complex was taken out, dispersed in washing machine water, adsorbed on cotton 2y to a concentration of 1% after drying, and 1g was taken from the dried material and used as a deodorizer sample. .

実施例4 ヘマチン2 0 0 M9を1規定カセイソーダ水溶液
5 mlに溶解後、純水1 0 0 mlを加えて希釈
した溶液に、別に水25村に塩化コバルト・6水塩75
mgを溶解した液を加えて充分混合した後、希硝酸でp
 i−Iを5. 9 − 6. 0に調整し、析出する
ヘマチンコバルト錯体をP取、水洗機水中に分散させて
、これを活性炭2yに乾燥後1%となる様吸着させ、乾
燥したものから1gを取り脱臭剤供試料とした。
Example 4 After dissolving hematin 200 M9 in 5 ml of 1N caustic soda aqueous solution, 100 ml of pure water was added to dilute the solution, and 75 ml of cobalt chloride hexahydrate was separately added to 25 ml of water.
After adding the solution containing 100 mg of nitric acid and mixing thoroughly, p
i-I 5. 9-6. 0, the precipitated hematin cobalt complex was taken out, dispersed in washing machine water, adsorbed on activated carbon 2y to a concentration of 1% after drying, and 1 g was taken from the dried product and used as a deodorizer sample. .

実施例5 ヘマチン200〜を1規定−カセイソーダ水溶液5 m
lに溶解後、純水1 0 0 rnlを加えて希釈した
溶液に、別に水25m1に硝酸マンガン・4水塩79N
を溶解jノだ液を加えて充分混合した後、希硝酸でpH
を6. 9 − 7. 0に調整し、析出するヘマチン
マンガン錯体をP取、水洗機水中に分散させて、これを
シリカゲル2yに乾燥後1%になる様吸着させ、乾燥し
たものから1f/を取り脱臭剤供試料とした。
Example 5 Hematin 200 ~ 1 N-caustic soda aqueous solution 5 m
1, add 100 rnl of pure water to dilute the solution, and separately add 79N of manganese nitrate tetrahydrate to 25ml of water.
After adding saliva and mixing thoroughly, adjust the pH with dilute nitric acid.
6. 9-7. 0, the hematin manganese complex precipitated was removed, dispersed in washing machine water, adsorbed on silica gel 2y to a concentration of 1% after drying, and 1f/ was taken from the dried product and used as a deodorizer sample. did.

脱臭試験 2e容のテトラ−バックに実施例1〜5で調製した脱臭
剤供試料1gを入れ、密封した後、所定の虐度に調整し
た悪臭ガス(アンモニヤ、トリメチルアミン、硫化水素
、メチルメルカプタン)を各々1eを通じた後、経時的
に悪臭ガス濃度をガス検知管(株式会社ガスチック社製
)にて測定した。測定結果は一括して第1表に示す。
Deodorization test 1 g of the deodorizer sample prepared in Examples 1 to 5 was placed in a 2e volume Tetra bag, and after sealing, malodorous gases (ammonia, trimethylamine, hydrogen sulfide, methyl mercaptan) adjusted to a specified severity were added. After passing through 1e, the concentration of malodorous gas was measured over time using a gas detection tube (manufactured by Gastic Co., Ltd.). The measurement results are summarized in Table 1.

この結果から明らかな様に本発明脱臭剤はいずれの悪臭
ガスに対しても、又どのような剤型においても浸れた脱
臭効果を葡していることが確認された。
As is clear from these results, it was confirmed that the deodorizing agent of the present invention has a strong deodorizing effect against any malodorous gas and in any dosage form.

以下余白 抗14試験 (1)最少発育阻止C層間(MIC)の測定試EflO
Omqを10m1のジメチルスルホキシドに俗解して1
0.000 ti!J/肩lの試料原液を調製した。こ
の原液をジメチルスルホキシドで希釈してs、o o 
o、+、 000.500.250.125.100.
50.25.125.1μり/mlの希釈系列を作り試
験に用いた。試料原液及び希釈系列の各々から無菌的に
1 mlをシャーレにとり、感受性用寒天培地9 ml
と混合して平板培地を調製した。
The following margin anti-14 test (1) Minimum growth inhibition C interlayer (MIC) measurement test EflO
Omq is commonly understood as 10ml of dimethyl sulfoxide.
0.000ti! A sample stock solution of J/shoulder l was prepared. This stock solution was diluted with dimethyl sulfoxide and s, o o
o, +, 000.500.250.125.100.
A dilution series of 50.25.125.1 μl/ml was prepared and used in the test. Aseptically take 1 ml of each sample stock solution and dilution series into a Petri dish, and add 9 ml of sensitive agar medium.
A plate medium was prepared by mixing with

試験用細菌液は、日本化学療法学会の定めるM I C
測定法(1980)に基づき調製した。その菌液を上記
の平板培地に1白金耳ずつ塗布し、37°Cで24時間
培養して、菌の発育のみられない最小0度をMICとし
た。試験結果を一括して第2表に示す。
The bacterial solution for testing is MIC specified by the Japanese Society of Chemotherapy.
It was prepared based on the measurement method (1980). The bacterial solution was applied one platinum loop at a time to the above-mentioned plate medium and cultured at 37°C for 24 hours, and the lowest temperature of 0°C at which no bacterial growth was observed was defined as the MIC. The test results are summarized in Table 2.

(2)  シェークフラスコ法による測定実施例1〜5
で調製した脱臭剤供試料を滅菌後、試験菌の懸濁緩衝液
を注加し、密閉容器中で150回/分、1時間振盪後の
生菌数を計測し、圧加懸濁液の菌数に対する減少率を求
めた。試験結果は一括して第3表に示す。
(2) Measurement Examples 1 to 5 by shake flask method
After sterilizing the deodorant sample prepared in step 1, a suspension buffer of the test bacteria was added, and the number of viable bacteria was counted after shaking at 150 times/min for 1 hour in a closed container. The reduction rate for the number of bacteria was determined. The test results are summarized in Table 3.

以上の結果から本発明脱臭剤は優れた抗菌作用を有して
いることが判明し、微生物の関与する悪臭にも効果のあ
ることが確認された。
From the above results, it was found that the deodorizing agent of the present invention has excellent antibacterial action, and it was also confirmed that it is effective against bad odors caused by microorganisms.

以下余白 (発明の効果) 本発明によれば強力な抗菌作用も葺しているため微生物
の関与する悪臭にも効果を示しかつ安全で且つ持続性の
ある化学的な脱臭作用を有する極めて実用性の高い抗菌
脱臭剤が提供される。
Margin below (Effects of the invention) According to the present invention, it has a strong antibacterial effect, so it is effective against bad odors caused by microorganisms, and has a safe and long-lasting chemical deodorizing effect, making it extremely practical. A highly antibacterial deodorizer is provided.

手  続  補  正  書  (自発 )平成1 年
′ら7日
Procedural Amendment (Voluntary) 1999' et al. 7th

Claims (1)

【特許請求の範囲】[Claims] ヘマチンもしくはその金属錯体を含有してなる抗菌脱臭
剤。
An antibacterial deodorizer containing hematin or its metal complex.
JP63242144A 1988-09-26 1988-09-26 Antibacterial deodorant Pending JPH0288069A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP63242144A JPH0288069A (en) 1988-09-26 1988-09-26 Antibacterial deodorant

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP63242144A JPH0288069A (en) 1988-09-26 1988-09-26 Antibacterial deodorant

Publications (1)

Publication Number Publication Date
JPH0288069A true JPH0288069A (en) 1990-03-28

Family

ID=17084972

Family Applications (1)

Application Number Title Priority Date Filing Date
JP63242144A Pending JPH0288069A (en) 1988-09-26 1988-09-26 Antibacterial deodorant

Country Status (1)

Country Link
JP (1) JPH0288069A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0806935A2 (en) * 1995-02-03 1997-11-19 Beiersdorf Aktiengesellschaft Anti-adhesive active principles
CN103477997A (en) * 2013-08-29 2014-01-01 江苏中恒宠物用品股份有限公司 Machining process for pet urinal pad with deodorizing function

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0806935A2 (en) * 1995-02-03 1997-11-19 Beiersdorf Aktiengesellschaft Anti-adhesive active principles
CN103477997A (en) * 2013-08-29 2014-01-01 江苏中恒宠物用品股份有限公司 Machining process for pet urinal pad with deodorizing function

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