JPH04335141A - Malodorous-sulfide detecting element - Google Patents
Malodorous-sulfide detecting elementInfo
- Publication number
- JPH04335141A JPH04335141A JP10716591A JP10716591A JPH04335141A JP H04335141 A JPH04335141 A JP H04335141A JP 10716591 A JP10716591 A JP 10716591A JP 10716591 A JP10716591 A JP 10716591A JP H04335141 A JPH04335141 A JP H04335141A
- Authority
- JP
- Japan
- Prior art keywords
- malodorous
- sulfide
- fluorescent substance
- fluorescent material
- fluorescence
- 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
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims abstract description 31
- 239000000463 material Substances 0.000 claims abstract description 17
- 239000000126 substance Substances 0.000 claims description 30
- 238000001514 detection method Methods 0.000 claims description 20
- 230000005284 excitation Effects 0.000 claims description 8
- 239000002861 polymer material Substances 0.000 claims description 8
- -1 oxine metal complex Chemical class 0.000 claims description 3
- WQOXQRCZOLPYPM-UHFFFAOYSA-N dimethyl disulfide Chemical compound CSSC WQOXQRCZOLPYPM-UHFFFAOYSA-N 0.000 description 18
- 230000035945 sensitivity Effects 0.000 description 8
- 150000003568 thioethers Chemical class 0.000 description 8
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- 230000008786 sensory perception of smell Effects 0.000 description 6
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 5
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 3
- 239000003205 fragrance Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 229910052725 zinc Inorganic materials 0.000 description 3
- 239000011701 zinc Substances 0.000 description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 2
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 2
- 229920002845 Poly(methacrylic acid) Polymers 0.000 description 2
- 239000003012 bilayer membrane Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000009965 odorless effect Effects 0.000 description 2
- 239000005020 polyethylene terephthalate Substances 0.000 description 2
- 229920000139 polyethylene terephthalate Polymers 0.000 description 2
- 150000004032 porphyrins Chemical class 0.000 description 2
- 239000013074 reference sample Substances 0.000 description 2
- 239000000523 sample Substances 0.000 description 2
- 125000000980 1H-indol-3-ylmethyl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([H])=C(C([H])([H])[*])C2=C1[H] 0.000 description 1
- UZSGWJQJDLCCFN-UHFFFAOYSA-N 2-acetylbenzonitrile Chemical compound CC(=O)C1=CC=CC=C1C#N UZSGWJQJDLCCFN-UHFFFAOYSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 description 1
- 238000007872 degassing Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000010355 oscillation Effects 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- ANRHNWWPFJCPAZ-UHFFFAOYSA-M thionine Chemical compound [Cl-].C1=CC(N)=CC2=[S+]C3=CC(N)=CC=C3N=C21 ANRHNWWPFJCPAZ-UHFFFAOYSA-M 0.000 description 1
Abstract
Description
【０００１】0001
【産業上の利用分野】本発明は、微量の悪臭硫化物を検
出可能な悪臭硫化物検知素子に関する。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a malodorous sulfide detection element capable of detecting trace amounts of malodorous sulfides.
【０００２】0002
【従来の技術】匂い物質の検出方法としては、特開昭６
３−２２２２４８号公報に開示されているように、水晶
発振子上に二分子膜を固定し、この二分子膜に匂い物質
を吸着させ、吸着量を水晶発振子の発振周波数の変化か
ら求める方法が提案されている。[Prior Art] As a method for detecting odorants, Japanese Patent Application Laid-open No. 6
As disclosed in Publication No. 3-222248, a bilayer membrane is fixed on a crystal oscillator, an odorant is adsorbed to the bilayer membrane, and the amount of adsorption is determined from a change in the oscillation frequency of the crystal oscillator. is proposed.
【０００３】しかしながら、この検出方法は、悪臭硫化
物については感度が低く、また温度の影響を受ける等の
問題を有し、数１０ｐｐｍオーダが検知の限界であり、
人間の嗅覚限界の濃度（数ｐｐｂ）を検出することは困
難であった。However, this detection method has problems such as low sensitivity for malodorous sulfides and being affected by temperature, and the detection limit is on the order of several tens of ppm.
It has been difficult to detect concentrations at the limit of human olfactory sense (several parts per billion).
【０００４】それ故、人間の嗅覚限界の濃度の悪臭硫化
物を検出できる検知素子が望まれていた。[0004]Therefore, there has been a desire for a sensing element capable of detecting malodorous sulfides at a concentration that is at the limit of the human sense of smell.
【０００５】[0005]
【発明が解決しようとする課題】かかる現状に鑑み、本
発明は、人間の嗅覚限界の濃度までの微量悪臭硫化物質
を検出することが可能な悪臭硫化物検知素子を提供する
ことを目的とする。[Problems to be Solved by the Invention] In view of the current situation, an object of the present invention is to provide a malodorous sulfide detection element capable of detecting trace amounts of malodorous sulfide substances up to a concentration that is at the limit of human olfactory sense. .
【０００６】[0006]
【課題を解決するための手段】本発明の要旨は、蛍光物
質と蛍光物質を保持する高分子材料からなり、該蛍光物
質と悪臭硫化物とを接触させ、該蛍光物質から発せられ
る蛍光強度を測定することにより該悪臭硫化物を検知す
る悪臭硫化物検知素子であって、該高分子材料が該蛍光
物質を励起するための励起光および該蛍光物質から発せ
られる蛍光を透過し、かつ該励起光により前記蛍光物質
と同じ波長域に蛍光を発しないことを特徴とする悪臭硫
化物検知素子に存在する。[Means for Solving the Problems] The gist of the present invention is to consist of a fluorescent substance and a polymer material holding the fluorescent substance, to bring the fluorescent substance into contact with a malodorous sulfide, and to reduce the intensity of the fluorescence emitted from the fluorescent substance. A malodorous sulfide detection element that detects the malodorous sulfide by measuring the malodorous sulfide, the polymer material transmits excitation light for exciting the fluorescent substance and fluorescence emitted from the fluorescent substance, and the excitation It exists in a malodorous sulfide detection element characterized in that it does not emit fluorescence in the same wavelength range as the fluorescent substance when exposed to light.
【０００７】第２の要旨は、第１の要旨において、前記
蛍光物質がオキシン金属錯体からなることを特徴とする
悪臭硫化物検知素子に存在する。A second aspect resides in the malodorous sulfide detection element according to the first aspect, characterized in that the fluorescent substance is composed of an oxine metal complex.
【０００８】本発明の素子は、蛍光物質と蛍光物質を保
持する高分子材料から構成される。。ここで保持とは、
蛍光物質を、高分子材料中に分散、含浸、塗布した状態
を意味する。The device of the present invention is composed of a fluorescent substance and a polymeric material that holds the fluorescent substance. . Here, retention means
Refers to a state in which a fluorescent substance is dispersed, impregnated, or coated in a polymeric material.
【０００９】本発明のいう悪臭硫化物とは、いおう原子
を含む化学物質であり、例えば、硫化水素、メチルメル
カプタン、、硫化メチル、二硫化メチル等である。The malodorous sulfide referred to in the present invention is a chemical substance containing a sulfur atom, such as hydrogen sulfide, methyl mercaptan, methyl sulfide, and methyl disulfide.
【００１０】本発明において用いられる高分子材料とし
ては、蛍光物質を励起するための励起光および蛍光物質
から発せられる蛍光を透過し、かつ励起光により蛍光を
発しない材料であれば適宜の材料からなるものが用いら
れ、例えば、ポリメタクリル酸メタクリレート（ＰＭＭ
Ａ）、ポリカーボネート（ＰＣ）、ポリエチレンテレフ
タレート（ＰＥＴ）等があげられる。形態としては、例
えば、板状、フィルム等が用いられる。The polymer material used in the present invention may be any suitable material as long as it transmits excitation light for exciting the fluorescent substance and fluorescence emitted from the fluorescent substance, and does not emit fluorescence due to the excitation light. For example, polymethacrylic acid methacrylate (PMM
A), polycarbonate (PC), polyethylene terephthalate (PET), etc. As for the shape, for example, a plate shape, a film, etc. are used.
【００１１】本発明において用いられる蛍光物質として
は、例えば、金属ポルフィリン錯体、シアニン系金属錯
体、シクロペンタジエニル金属錯体、ジチオレン誘導体
の金属錯体、オキシン金属錯体等があげられるが、検出
感度の点で、表１に示したオキシン金属錯体を用いるこ
とが好ましい。Examples of fluorescent substances used in the present invention include metal porphyrin complexes, cyanine metal complexes, cyclopentadienyl metal complexes, metal complexes of dithiolene derivatives, and oxine metal complexes. Therefore, it is preferable to use the oxine metal complexes shown in Table 1.
【００１２】0012
【表１】
ここで、ＯＸ：Ｃ９Ｈ７ＮＯ、ＯＸ’：Ｃ９Ｈ８Ｎ
Ｏ−[Table 1] Here, OX:C9H7NO, OX':C9H8N
O-
【００１３】本発明の悪臭検知素子は、例えば次の
方法により作製することができる。すなわち、上記蛍光
物質の少なくとも１種を上記の高分子材料の溶液に分散
した後、キャストフィルムを作製し、表１の乾燥温度で
乾燥することにより得られる。あるいは高分子材料に蛍
光物質を含浸または塗布する事によっても得られる。蛍
光物質の高分子材料に対する重量比は、分散及び含浸す
る場合、０．００５〜２０％が好ましく、０．０１〜５
％がより好ましい。０．０１〜５％の範囲で素子の感度
、精度はより向上する。蛍光物質を塗布する場合は、１
００Å〜１０μｍが好ましく、５００Å〜１μｍがより
好ましい。５００Å〜１μｍの範囲で感度、精度はより
一層向上する。The malodor detection element of the present invention can be produced, for example, by the following method. That is, it can be obtained by dispersing at least one of the above fluorescent substances in a solution of the above polymer material, producing a cast film, and drying it at the drying temperature shown in Table 1. Alternatively, it can also be obtained by impregnating or coating a polymeric material with a fluorescent substance. When dispersing and impregnating, the weight ratio of the fluorescent substance to the polymer material is preferably 0.005 to 20%, and 0.01 to 5%.
% is more preferable. The sensitivity and accuracy of the element are further improved within the range of 0.01 to 5%. When applying fluorescent material, 1
00 Å to 10 μm is preferable, and 500 Å to 1 μm is more preferable. Sensitivity and accuracy are further improved in the range of 500 Å to 1 μm.
【００１４】[0014]
【作用】このようにして作製された悪臭検知素子を悪臭
硫化物と接触させてると、蛍光物質の発光強度が変化す
る。しかもこの変化量は微量の悪臭硫化物でも大きく変
化するため、人間の嗅覚程度の微量な悪臭硫化物濃度ま
でも検出する事が可能となる。[Function] When the malodor detecting element thus prepared is brought into contact with malodorous sulfide, the emission intensity of the fluorescent substance changes. Moreover, since this amount of change changes greatly even with a trace amount of malodorous sulfide, it is possible to detect concentrations of malodorous sulfide as small as the human sense of smell.
【００１５】[0015]
【実施例】以下に実施例をあげて本発明を詳細に説明す
るが、本発明がこれら実施例に限定されないことはいう
までもない。EXAMPLES The present invention will be explained in detail with reference to Examples below, but it goes without saying that the present invention is not limited to these Examples.
【００１６】（実施例１）本実施例では、高分子材料と
してポリメタクリル酸メタクリレート（ＰＭＭＡ）、蛍
光物質として、オキシン亜鉛錯体を用いた。(Example 1) In this example, polymethacrylic acid methacrylate (PMMA) was used as the polymer material, and oxine zinc complex was used as the fluorescent material.
【００１７】ＰＭＭＡの２０重量％メチルエチルケトン
溶液２５ｇ中にオキシン亜鉛錯体２ｍｇを加え均一に分
散させた後、ガラス板上にアプリケータを用いてキャス
トしフィルムを作製した。作製したフィルムを９０℃の
オーブン中で５時間乾燥し、膜厚５０μｍの図１に示す
構造の悪臭硫化物検知素子４を得た。After adding 2 mg of oxine zinc complex to 25 g of a 20% by weight solution of PMMA in methyl ethyl ketone and uniformly dispersing it, the mixture was cast onto a glass plate using an applicator to prepare a film. The produced film was dried in an oven at 90° C. for 5 hours to obtain a malodorous sulfide detection element 4 having a film thickness of 50 μm and having the structure shown in FIG. 1.
【００１８】次に、悪臭硫化物質検知素子４を図２に示
すように蛍光測定用ホルダー３に固定し、デシケータ内
に入れ脱気を充分に行なった。あらかじめ種々の濃度に
調整した無臭袋内の二硫化メチルをデシケータ内に導入
し、上記検知素子４に１０分間接触させた。また、参照
試料として、悪臭硫化物を導入しない無臭気状態に放置
した試料も併せて用意した。Next, the malodorous sulfide substance detection element 4 was fixed to the fluorescence measurement holder 3 as shown in FIG. 2, and placed in a desiccator for sufficient degassing. Methyl disulfide in an odorless bag, which had been adjusted to various concentrations in advance, was introduced into the desiccator and brought into contact with the detection element 4 for 10 minutes. In addition, as a reference sample, a sample left in an odorless state without introducing malodorous sulfides was also prepared.
【００１９】以上の試料について、日本分光工業株式会
社製ＦＰ−７７７分光蛍光光度計を用い、図２に示すよ
うに３８２ｎｍの励起光を照射して、素子４から発せら
れる波長５００ｎｍの蛍光の強度を測定した。結果を図
３に示す。図３は、参照試料の蛍光強度に対し、種々の
濃度の二硫化メチルを接触させたときの蛍光強度の減少
率（％）を示すグラフである。The above sample was irradiated with excitation light of 382 nm as shown in FIG. 2 using an FP-777 spectrofluorometer manufactured by JASCO Corporation, and the intensity of fluorescence at a wavelength of 500 nm emitted from element 4 was measured. was measured. The results are shown in Figure 3. FIG. 3 is a graph showing the reduction rate (%) of the fluorescence intensity of the reference sample when it is brought into contact with various concentrations of methyl disulfide.
【００２０】図３から明らかなように、ｐｐｂのオーダ
ーまで二硫化メチルの濃度に応じて蛍光強度は変化し、
蛍光強度の減少率は濃度の対数と直線関係にあることが
分かった。人間の嗅覚の二硫化メチルに対する閾値濃度
が３ｐｐｂ程度であることから、本実施例の素子は人間
の嗅覚感度に匹敵し、また感度特性が濃度の対数に比例
することから、におい物質の濃度を人間の匂いに対する
感覚として定量的に得ることも可能となった。As is clear from FIG. 3, the fluorescence intensity changes depending on the concentration of methyl disulfide up to the order of ppb.
It was found that the rate of decrease in fluorescence intensity had a linear relationship with the logarithm of the concentration. Since the threshold concentration of the human sense of smell for methyl disulfide is about 3 ppb, the element of this example is comparable to the human sense of smell sensitivity, and since the sensitivity characteristic is proportional to the logarithm of the concentration, the element of this example can reduce the concentration of odorants. It has also become possible to quantitatively obtain the human sense of smell.
【００２１】（実施例２）実施例１と同じ悪臭検知素子
を用い、同様にして二硫化メチル以外の悪臭硫化物に対
する悪臭硫化物検知素子の蛍光強度減少率を測定した。
結果を表２に示す。(Example 2) Using the same malodor detecting element as in Example 1, the rate of decrease in fluorescence intensity of the malodorous sulfide detecting element with respect to malodorous sulfides other than methyl disulfide was measured in the same manner. The results are shown in Table 2.
【００２２】[0022]
【表２】[Table 2]
【００２３】表２から明らかなように、蛍光強度の減少
が確認され、本実施例の悪臭検知素子は、二硫化メチル
の場合と同様に、種々の悪臭硫化物に対しても、高い検
出感度を有することが分かった。As is clear from Table 2, a decrease in fluorescence intensity was confirmed, and the malodor detection element of this example has high detection sensitivity for various malodorous sulfides, as in the case of methyl disulfide. It was found that it has
【００２４】（実施例３）ポルフィリンマグネシウム錯
体について、実施例１と同様にして、キャストフィルム
を作製し、１００℃乾燥させて悪臭硫化物検知素子を作
製した。この素子について、実施例１と同様に二硫化メ
チルに接触させ蛍光強度の減少率の測定した。ここで、
励起光の波長は４２０ｎｍ、蛍光波長は６００ｎｍを用
いた。(Example 3) A cast film of the porphyrin magnesium complex was produced in the same manner as in Example 1, and dried at 100°C to produce a malodorous sulfide detection element. This element was brought into contact with methyl disulfide in the same manner as in Example 1, and the rate of decrease in fluorescence intensity was measured. here,
The excitation light wavelength was 420 nm, and the fluorescence wavelength was 600 nm.
【００２５】実施例１の素子と比べて、悪臭硫化物の濃
度に対する蛍光減少率は小さく、また感度も低いが、数
１０ｐｐｂオーダーでは悪臭硫化物を検出できることを
示した。Compared to the device of Example 1, the fluorescence reduction rate with respect to the concentration of malodorous sulfides was small and the sensitivity was low, but it was shown that malodorous sulfides could be detected at levels of several tens of ppb.
【００２６】[0026]
【発明の効果】本発明により、人間の嗅覚限界の濃度の
悪臭硫化物を検出することができ、しかも悪臭硫化物の
濃度変化に対し、人間の嗅覚と同じ感度特性を有する悪
臭硫化物検出素子を提供することが可能となる。Effects of the Invention According to the present invention, a malodorous sulfide detection element is capable of detecting malodorous sulfide at a concentration that is at the limit of human olfactory sense, and has the same sensitivity characteristics as the human sense of smell with respect to changes in the concentration of malodorous sulfide. It becomes possible to provide
【図１】悪臭硫化物検知素子の構成を示す概略図。FIG. 1 is a schematic diagram showing the configuration of a malodorous sulfide detection element.
【図２】悪臭硫化物素子の蛍光強度を測定する方法を示
す概略図。FIG. 2 is a schematic diagram showing a method for measuring the fluorescence intensity of a malodorous sulfide element.
【図３】二硫化メチル濃度と蛍光強度の変化率との関係
を示すグラフ。FIG. 3 is a graph showing the relationship between methyl disulfide concentration and rate of change in fluorescence intensity.
１ ＰＭＭＡ、 ２ オキシン亜鉛錯体、 ３ 透明石英板、 ４ 悪臭硫化物検知素子。 1 PMMA, 2 Oxine zinc complex, 3 Transparent quartz plate, 4 Malodorous sulfide detection element.
Claims (2)
材料からなり、該蛍光物質と悪臭硫化物とを接触させ、
該蛍光物質から発せられる蛍光強度を測定することによ
り、該悪臭硫化物を検知する悪臭硫化物検知素子であっ
て、該高分子材料が、該蛍光物質を励起するための励起
光および該蛍光物質から発せられる蛍光を透過し、かつ
該励起光により前記蛍光物質と同じ波長域に蛍光を発し
ない材料であることを特徴とする悪臭硫化物検知素子。Claim 1: Comprised of a fluorescent substance and a polymer material holding the fluorescent substance, the fluorescent substance and a malodorous sulfide are brought into contact with each other,
A malodorous sulfide detection element that detects the malodorous sulfide by measuring the fluorescence intensity emitted from the fluorescent substance, wherein the polymer material is configured to absorb excitation light for exciting the fluorescent substance and the fluorescent substance. 1. A malodorous sulfide detection element characterized by being made of a material that transmits fluorescence emitted from the substance and does not emit fluorescence in the same wavelength range as the fluorescent substance due to the excitation light.
なることを特徴とする請求項１記載の悪臭硫化物検知素
子。2. The malodorous sulfide detection element according to claim 1, wherein the fluorescent substance is composed of an oxine metal complex.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10716591A JPH04335141A (en) | 1991-05-13 | 1991-05-13 | Malodorous-sulfide detecting element |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10716591A JPH04335141A (en) | 1991-05-13 | 1991-05-13 | Malodorous-sulfide detecting element |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH04335141A true JPH04335141A (en) | 1992-11-24 |
Family
ID=14452137
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP10716591A Pending JPH04335141A (en) | 1991-05-13 | 1991-05-13 | Malodorous-sulfide detecting element |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH04335141A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2005039656A1 (en) * | 2003-10-16 | 2005-05-06 | Kimberly-Clark Worldwide, Inc. | Odor controlling article including a visual indicating device for monitoring odor absorption |
-
1991
- 1991-05-13 JP JP10716591A patent/JPH04335141A/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2005039656A1 (en) * | 2003-10-16 | 2005-05-06 | Kimberly-Clark Worldwide, Inc. | Odor controlling article including a visual indicating device for monitoring odor absorption |
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