JPH09135893A - Antibacterial material and antibacterial molding using the same - Google Patents
Antibacterial material and antibacterial molding using the sameInfo
- Publication number
- JPH09135893A JPH09135893A JP7300118A JP30011895A JPH09135893A JP H09135893 A JPH09135893 A JP H09135893A JP 7300118 A JP7300118 A JP 7300118A JP 30011895 A JP30011895 A JP 30011895A JP H09135893 A JPH09135893 A JP H09135893A
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- Prior art keywords
- antibacterial
- group
- phenoxy resin
- functional group
- formula
- Prior art date
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- Materials For Medical Uses (AREA)
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Abstract
Description
【０００１】[0001]
【発明の属する技術分野】本発明は、高分子基材に塗布
可能な、抗菌性材料に関する。TECHNICAL FIELD The present invention relates to an antibacterial material that can be applied to a polymer substrate.
【０００２】[0002]
【従来の技術】医療の分野においては、ポリウレタンな
どの高分子材料から成る医療用具を患者の体内に挿入・
留置している間に起きる感染症が合併症の一つとして問
題視されている。従来、医療用具の留置に伴う感染症を
防止するために、医療用具を使用直前にクロロヘキシジ
ンやポピドンヨードなどの抗菌剤や消毒剤を含む水溶液
に浸漬するなどして消毒するか、あるいは治療中に交換
可能な医療用具に関しては頻繁な交換が行われている。
しかしながら、抗菌剤・消毒剤は時間と共にカテーテル
表面から消失するため消毒の効果に持続性がなく、医療
用具を長期間にわたって使用する場合には徐々に効果が
低下していくことは明らかである。また、医療用具の頻
繁な交換も医療従事者にとっては大きな負担となる。そ
こで更なる感染防止の手段の一つとして、医療用具に種
々の抗菌加工が施されてきた。その代表的なものとして
は、クロロヘキシジンをはじめとする抗菌剤や、銀・銅
をはじめとする金属またはその化合物を含有する層で表
面を被覆したカテーテルがある。これらのカテーテルに
おいては、抗菌作用をもつ物質を体内で一定量ずつ徐放
するシステムが採用されており、カテーテルを使用直前
に消毒する場合に比べて良好な効果を示す。2. Description of the Related Art In the medical field, a medical device made of a polymer material such as polyurethane is inserted into a patient's body.
Infection that occurs during detention is regarded as one of the complications. Conventionally, in order to prevent infectious diseases associated with the placement of medical devices, they are disinfected by immersing them in an aqueous solution containing an antibacterial agent or disinfectant such as chlorohexidine or povidone iodine immediately before use, or replaced during treatment. Frequent replacements are made for possible medical devices.
However, since the antibacterial agent / disinfectant disappears from the catheter surface with time, the effect of disinfection is not persistent, and it is clear that the effect gradually decreases when the medical device is used for a long period of time. Frequent replacement of medical equipment also places a heavy burden on healthcare professionals. Therefore, various antibacterial treatments have been applied to medical devices as one of means for further preventing infection. Typical examples thereof include a catheter whose surface is coated with a layer containing an antibacterial agent such as chlorohexidine and a metal such as silver / copper or a compound thereof. In these catheters, a system is employed in which a substance having an antibacterial action is gradually released in the body by a fixed amount at a time, and shows a better effect as compared with a case where the catheter is disinfected immediately before use.
【０００３】[0003]
【発明が解決しようとする課題】しかしながら、抗菌物
質が徐放するシステムでは依然として使用期間に限りが
あり効力が次第に低下していくことは避けられない。銀
などの金属あるいはその化合物については徐放後の体内
動態が不明であり、人体への害も考えられる。また、使
用後の医療用具廃棄物に銀が残存している場合には、廃
棄に際して回収などの特別の処置が必要になる。However, in a system in which an antibacterial substance is gradually released, it is unavoidable that the period of use is still limited and the efficacy gradually decreases. The pharmacokinetics of metals such as silver and its compounds after sustained release are unknown, and they may be harmful to the human body. In addition, if silver remains in the medical device waste after use, special treatment such as recovery is required at the time of disposal.
【０００４】そのため、徐放型でなく、それ自身で抗菌
性のあるポリマーとして第四級アンモニウム基をもつポ
リマー（特公平７−２０８４６）が開発されているが、
これらはタンパク質や酸性の有用物質を吸着しやすい欠
点がり、また、抗菌スペクトルも狭い欠点がある。ま
た、抗菌スペクトルを改良したものとしてヨード化ポリ
スチレン繊維（特公平７−２０８４５）が開発され、こ
れ自体は優れた抗菌スペクトルがあるが、可溶性のポリ
マーではないので、いろんな形をした医療用具に適用で
きない欠点がある。Therefore, a polymer having a quaternary ammonium group (Japanese Patent Publication No. 7-20846) has been developed as a polymer having antibacterial properties by itself, instead of the sustained release type.
These have a drawback that they are likely to adsorb proteins and acidic useful substances, and have a narrow antibacterial spectrum. In addition, an iodinated polystyrene fiber (Japanese Patent Publication No. 7-20845) was developed as an improved antibacterial spectrum. It has an excellent antibacterial spectrum, but since it is not a soluble polymer, it can be applied to various types of medical devices. There is a drawback that cannot be done.
【０００５】そこで、本発明者らはかかる従来技術の問
題点に鑑み、複雑な形をした医療用具にも適用できるよ
うな可溶性で柔軟な膜を形成し、かつ、種々のポリマー
との相溶性・接着性に優れ、かつ優れた抗菌性能を有す
る抗菌性材料およびそれを用いた成型品を提供すること
を目的とする。In view of the problems of the prior art, the present inventors have formed a soluble and flexible film which can be applied to a medical device having a complicated shape, and have compatibility with various polymers. -An object of the present invention is to provide an antibacterial material having excellent adhesiveness and excellent antibacterial performance, and a molded article using the same.
【０００６】[0006]
【課題を解決するための手段】かかる課題を達成するた
めに、本発明は、下記の構成を有する。In order to achieve the above object, the present invention has the following constitution.
【０００７】「水酸基の少なくとも一部が、下記一般式
（但し、式中、Ａは、エーテル基またはエステル基を含
む結合基を示す。Ｒはアルキレン基を示す。）で表され
る官能基で置換されてなるフェノキシ樹脂からなること
を特徴とする抗菌性材料。"At least a part of the hydroxyl groups is a functional group represented by the following general formula (wherein A represents a bonding group containing an ether group or an ester group, and R represents an alkylene group). An antibacterial material characterized by comprising a substituted phenoxy resin.
【０００８】 −Ａ−Ｒ−Ｉ （１） 」-A-R-I (1) "
【０００９】[0009]
【発明の実施の形態】続いて、本発明についてさらに詳
細に説明する。Next, the present invention will be described in more detail.
【００１０】本発明でいうフェノキシ樹脂とは、二価フ
ェノールとエピクロルヒドリンの反応によって得られる
実質上エポキシド官能性をもたない一般式： ［−Ｄ−Ｏ−ＣＨ2 −ＣＨ（ＯＨ）−ＣＨ2 −］n （式中、Ｄは二価フェノールの残基であり、ｎは３０〜
２００の整数である）で表される重合体で、かつ、ジメ
チルホルムアミド又はテトラヒドロフランに５％以上溶
解するものを意味する。ここで二価フェノールとしては
２，２−ビス（４−ヒドロキシフェノール）プロパン、
ビス（４−ヒドロキシフェニルメタン）などで代表され
るビス（ヒドロキシフェニル）アルカン類、ビス（４−
ヒドロキシフェニル）エーテルで代表されるジ（ヒドロ
キシフェニル）エーテル類、ビス（４−ヒドロキシフェ
ニル）スルホンで代表されるジ（ヒドロキシフェニル）
スルホン類などが包含される。この中でビスフェノール
Ａを用いたフェノキシ樹脂が工業的に大量生産されてい
るので、汎用性が高い。[0010] The phenoxy resin in the present invention, no substantial epoxide functionality obtained by reacting a dihydric phenol with epichlorohydrin general formula: [-D-O-CH 2 -CH (OH) -CH 2 -] N (In the formula, D is a residue of a dihydric phenol, and n is 30 to
(An integer of 200) and is soluble in dimethylformamide or tetrahydrofuran by 5% or more. Here, as the dihydric phenol, 2,2-bis (4-hydroxyphenol) propane,
Bis (hydroxyphenyl) alkanes represented by bis (4-hydroxyphenylmethane), bis (4-)
Di (hydroxyphenyl) ethers represented by hydroxyphenyl) ether, di (hydroxyphenyl) represented by bis (4-hydroxyphenyl) sulfone
Sulfones and the like are included. Among them, a phenoxy resin using bisphenol A is industrially mass-produced, and thus has high versatility.
【００１１】本発明における式（１）で示される官能基
において、Ｒはメチレン基であるが、抗菌性の点で炭素
数１〜１７のものが好ましく、さらには、炭素数１〜１
１のものが抗菌性が特に強く好ましい。フェノキシ樹脂
と抗菌性官能基の結合はエーテル結合またはエステル結
合でなされる。具体的には、例えば、Ｏ−ＣＯ，Ｏ−Ｃ
Ｏ−ＮＨ，Ｏ−ＣＳ−ＮＨなどを含む結合基が好ましく
用いられる。In the functional group represented by the formula (1) in the present invention, R is a methylene group, but preferably has 1 to 17 carbon atoms in view of antibacterial property, and further has 1 to 1 carbon atoms.
No. 1 has a particularly strong antibacterial property and is preferable. The bond between the phenoxy resin and the antibacterial functional group is formed by an ether bond or an ester bond. Specifically, for example, O-CO, OC
A linking group containing O-NH, O-CS-NH and the like is preferably used.
【００１２】本発明における式（１）の抗菌性官能基
は、フェノキシ樹脂に共有結合で固定されていることが
重要である。官能基の含有量は、通常繰り返し単位 1モ
ルあたり０．１モルだが、抗菌性能に優れる点から、特
に０．３モル以上、１．０モルが好ましい。It is important that the antibacterial functional group of the formula (1) in the present invention is fixed to the phenoxy resin by a covalent bond. The content of the functional group is usually 0.1 mol per 1 mol of the repeating unit, but from the viewpoint of excellent antibacterial performance, it is particularly preferably 0.3 mol or more and 1.0 mol.
【００１３】本発明の抗菌性能を有する材料の製造方法
は任意であるが、以下に例をあげて説明する。The method for producing the material having antibacterial properties according to the present invention is arbitrary, but will be described below with reference to examples.
【００１４】ビスフェノールＡ−エピクロルヒドリン重
合体であるフェノキシ樹脂に、ハロアシル基を導入す
る。さらにハロアシル化フェノキシ樹脂をヨウ化カリウ
ムと反応処理することによって本発明の抗菌性能を有す
る材料が製造される。また、フェノキシ樹脂に、ハロア
ルキルアミノカルボキシル基を導入し、ハロアルキルア
ミノカルボキシル化フェノキシ樹脂をヨウ化カリウムと
反応処理することによって製造する方法も挙げられる。A haloacyl group is introduced into a phenoxy resin which is a bisphenol A-epichlorohydrin polymer. Further, by reacting the haloacylated phenoxy resin with potassium iodide, the material having antibacterial properties of the present invention is produced. In addition, a method in which a haloalkylaminocarboxyl group is introduced into a phenoxy resin and the haloalkylaminocarboxylated phenoxy resin is subjected to a reaction treatment with potassium iodide can be used.
【００１５】本発明の抗菌性材料は、表面に塗布するこ
とによって、細菌感染の防止が必要な任意の成型品、例
えば、医療用具などに好適に適用することができる。特
に、長期間にわたり体内に留置される血管カテーテル、
ドレナージチューブ、コネクター、排液バックなどに好
適に適用することができる。徐放システムの材料に比べ
て、抗菌官能基がフェノキシ樹脂に共有結合で固定化さ
れているため人体にとって安全で、効果が持続する。ま
た、かかる成型品としては、ポリウレタン成型品、天然
ゴム、シリコン樹脂成型品、ポリ塩化ビニル成型品など
が好適に用いられる。By applying the antibacterial material of the present invention to the surface, it can be suitably applied to any molded article required to prevent bacterial infection, such as medical equipment. In particular, a blood vessel catheter left in the body for a long period of time,
It can be suitably applied to drainage tubes, connectors, drainage bags, and the like. Compared with the material of the sustained release system, the antibacterial functional group is covalently immobilized on the phenoxy resin, so it is safe for the human body and the effect lasts. Further, as such molded products, polyurethane molded products, natural rubber, silicone resin molded products, polyvinyl chloride molded products and the like are preferably used.
【００１６】以下、実施例により本発明をさらに具体的
に説明するが、本発明は当該実施例に限定されるもので
はない。Hereinafter, the present invention will be described in more detail with reference to examples, but the present invention is not limited to the examples.
【００１７】[0017]
実施例１ 市販のフェノキシレジン （ユニオンカーバイト社製、
Ｐｈｅｎｏｘｙ）6.8gをテトラヒドロフラン（以下、Ｔ
ＨＦと略す）80mlに溶解後、クロロアセチルクロリド
4.8mlを加えて室温で15時間反応させた。この溶液をメ
タノールに投入しポリマーを沈殿させた後、メタノール
および水で洗浄して乾燥した。次に、このクロロアセチ
ル化フェノキシ樹脂9.32g をジメチルホルムアミド 180
mlに溶解後、26％ヨウ化カリウム（ジメチルホルムアミ
ド溶液） 120mlを加えて60℃で 2時間反応させた。水に
投入しポリマーを沈殿させた後、水で洗浄・乾燥してヨ
ード基を有する抗菌性材料を得た。ヨード基の導入量は
フェノキシ樹脂の繰り返し単位 1モルあたり 0.7モルで
あった。Example 1 Commercially available phenoxy resin (manufactured by Union Carbide,
6.8 g of Phenoxy) is added to tetrahydrofuran (hereinafter referred to as T
Abbreviated as HF) After dissolving in 80 ml, chloroacetyl chloride
4.8 ml was added and reacted at room temperature for 15 hours. This solution was poured into methanol to precipitate a polymer, which was then washed with methanol and water and dried. Next, 9.32 g of this chloroacetylated phenoxy resin was added to dimethylformamide 180
After dissolving in ml, 120 ml of 26% potassium iodide (dimethylformamide solution) was added and reacted at 60 ° C for 2 hours. After pouring into water to precipitate the polymer, the polymer was washed with water and dried to obtain an antibacterial material having an iodine group. The amount of iodo group introduced was 0.7 mol per 1 mol of the repeating unit of the phenoxy resin.
【００１８】実施例２ 抗菌性材料の12.5wt％ＴＨＦ溶液を、ポリスチレン製の
シャーレの内壁に塗布して乾燥した。材料を塗布したシ
ャーレをアルコールで消毒した後、大腸菌（MC1061株）
あるいは黄色ブドウ球菌（FRI1169 株）を懸濁した生理
食塩水を添加し、菌懸濁液の生菌数を時間を追って測定
した。対照として抗菌性材料を塗布していないポリスチ
レンシャーレについても同様に操作した。その結果を下
表に示した。Example 2 A 12.5 wt% THF solution of an antibacterial material was applied to the inner wall of a polystyrene petri dish and dried. Escherichia coli (MC1061 strain) after disinfecting the petri dish coated with the material with alcohol
Alternatively, physiological saline in which Staphylococcus aureus (FRI1169 strain) was suspended was added, and the viable cell count of the bacterial suspension was measured over time. As a control, a polystyrene petri dish not coated with the antibacterial material was also operated in the same manner. The results are shown in the table below.
【００１９】[0019]
【表１】 実施例３ 実施例１に示した抗菌性材料の10wt％ＴＨＦ溶液にポリ
ウレタンのチューブを軸方向に浸し、浸漬・乾燥を 7回
繰り返すことにより、チューブに抗菌性材料を塗布し
た。チューブ表面の抗菌性材料の厚みは平均 145nmであ
った。材料を塗布したチューブをアルコールで消毒した
後、大腸菌（MC1061株）または黄色ブドウ球菌（FRI116
9 株）を菌濃度106 個／ｍｌになるように懸濁した生理
食塩水に浸漬し、10時間静置した。10時間後にチューブ
に付着した菌数を測定した。対照として抗菌性材料を塗
布していないポリウレタンチューブについても同様に操
作した。その結果、大腸菌の場合には抗菌性材料を塗布
していないポリウレタンチューブでは1269個、抗菌性材
料を塗布したチューブでは15個であった。また黄色ブド
ウ球菌の場合には、材料を塗布していないチューブでは
3312個、材料を塗布したチューブでは 0個であった。[Table 1] Example 3 The antibacterial material was applied to the tube by immersing the polyurethane tube in the axial direction of the 10 wt% THF solution of the antibacterial material shown in Example 1 and repeating the immersion and drying 7 times. The average thickness of the antibacterial material on the surface of the tube was 145 nm. After disinfecting the tube coated with the material with alcohol, E. coli (MC1061 strain) or Staphylococcus aureus (FRI116)
9 strains) were immersed in a physiological saline solution having a bacterial concentration of 10 6 cells / ml and allowed to stand for 10 hours. After 10 hours, the number of bacteria attached to the tube was measured. As a control, the same operation was performed on a polyurethane tube to which the antibacterial material was not applied. As a result, in the case of Escherichia coli, the number of polyurethane tubes to which the antibacterial material was not applied was 1269 and that of the tube to which the antibacterial material was applied was 15. In the case of Staphylococcus aureus, use a tube not coated with the material.
There were 3312 and 0 in the tube coated with the material.
【００２０】実施例４ 実施例１と同様の市販のフェノキシレジン 20.0gをジメ
チルホルムアミド 140mlに溶解後、ブロモウンデカノイ
ルクロリド13.0mlを加えて80℃で 5時間反応させた。こ
の溶液をメタノールに投入しポリマーを沈殿させた後、
メタノールおよび水で洗浄して乾燥した。次に、このブ
ロモウンデカノイル化フェノキシ樹脂3gをジメチルホル
ムアミド72mlに溶解後、24％ヨウ化カリウム（ジメチル
ホルムアミド溶液）50mlを加えて60℃で 3時間反応させ
た。水に投入しポリマーを沈殿させた後、水で洗浄・乾
燥してヨード基を有する抗菌性材料を得た。Example 4 20.0 g of a commercially available phenoxy resin similar to that used in Example 1 was dissolved in 140 ml of dimethylformamide, 13.0 ml of bromoundecanoyl chloride was added, and the mixture was reacted at 80 ° C. for 5 hours. After pouring the solution into methanol to precipitate the polymer,
It was washed with methanol and water and dried. Next, 3 g of this bromoundecanoylated phenoxy resin was dissolved in 72 ml of dimethylformamide, 50 ml of 24% potassium iodide (dimethylformamide solution) was added, and the mixture was reacted at 60 ° C. for 3 hours. After pouring into water to precipitate the polymer, the polymer was washed with water and dried to obtain an antibacterial material having an iodine group.
【００２１】実施例５ 実施例４に示した抗菌性材料の10wt％ＴＨＦ溶液にポリ
ウレタンのチューブを軸方向に浸し、浸漬・乾燥を 7回
繰り返すことにより、チューブに抗菌性材料を塗布し
た。材料を塗布したチューブをアルコールで消毒した
後、大腸菌（MC1061株）または黄色ブドウ球菌（FRI116
9 株）を菌濃度106 個／ｍｌになるように懸濁した生
理食塩水に浸漬し、24時間静置した。24時間後にチュー
ブに付着した菌数を測定した。対照として抗菌性材料を
塗布していないポリウレタンチューブについても同様に
操作した。その結果、大腸菌の場合には抗菌性材料を塗
布していないポリウレタンチューブでは1269個、抗菌性
材料を塗布したチューブでは83個であった。また黄色ブ
ドウ球菌の場合には、材料を塗布していないチューブで
は3312個、材料を塗布したチューブでは 0個であった。Example 5 A polyurethane tube was axially immersed in a 10 wt% THF solution of the antibacterial material shown in Example 4, and the immersion and drying were repeated 7 times to apply the antibacterial material to the tube. After disinfecting the tube coated with the material with alcohol, E. coli (MC1061 strain) or Staphylococcus aureus (FRI116)
9 strains) were immersed in a physiological saline solution having a bacterial concentration of 10 6 cells / ml and allowed to stand for 24 hours. Twenty-four hours later, the number of bacteria adhered to the tube was measured. As a control, the same operation was performed on a polyurethane tube to which the antibacterial material was not applied. As a result, in the case of E. coli, the number of polyurethane tubes to which the antibacterial material was not applied was 1269 and that of the tube to which the antibacterial material was applied was 83. In the case of Staphylococcus aureus, it was 3312 in the tube not coated with the material and 0 in the tube coated with the material.
【００２２】[0022]
【発明の効果】本発明の抗菌性材料は、プラスチック製
品、特に医療用具などに容易に塗布でき、細菌が高濃度
であっても良好な抗菌能を示し、その効果は長期間持続
する。本発明品には抗菌官能基が共有結合されており、
抗菌官能基が溶離することがないため、抗菌性能が長期
間持続し人体にも無害である。INDUSTRIAL APPLICABILITY The antibacterial material of the present invention can be easily applied to plastic products, especially medical devices, etc., and exhibits a good antibacterial activity even at a high concentration of bacteria, and its effect lasts for a long time. An antibacterial functional group is covalently bonded to the product of the present invention,
Since the antibacterial functional group does not elute, the antibacterial performance continues for a long time and is harmless to the human body.
Claims (5)
（但し、式中、Ａは、エーテル基またはエステル基を含
む結合基を示す。Ｒはアルキレン基を示す。）で表され
る官能基で置換されてなるフェノキシ樹脂からなること
を特徴とする抗菌性材料。 −Ａ−Ｒ−Ｉ （１）1. A functional group in which at least a part of the hydroxyl groups is represented by the following general formula (wherein A represents a bonding group containing an ether group or an ester group, and R represents an alkylene group). An antibacterial material comprising a phenoxy resin substituted with. -A-R-I (1)
ジ（ヒドロキシフェニル）エーテル類およびジ（ヒドロ
キシフェニル）スルホン類から選ばれることを特徴とす
る請求項１記載の抗菌性材利用。2. A bis (hydroxyphenyl) alkane,
The use of the antibacterial material according to claim 1, which is selected from di (hydroxyphenyl) ethers and di (hydroxyphenyl) sulfones.
分としてなる組成物を被覆してなることを特徴とする抗
菌性成型品。3. An antibacterial molded article comprising a base material coated with the composition containing the antibacterial material according to claim 1 as a main component.
成型品、シリコン樹脂成型品、ポリ塩化ビニル成型品か
ら選ばれることを特徴とする請求項３記載の抗菌性成型
品。4. The antibacterial molded product according to claim 3, wherein the base material is selected from polyurethane molded products, natural rubber molded products, silicone resin molded products and polyvinyl chloride molded products.
ター、アクセスポート、排液バックおよび血液回路から
選ばれることを特徴とする請求項３記載の抗菌性成型
品。5. The antibacterial molded article according to claim 3, wherein the base material is selected from a catheter, a tube, a connector, an access port, a drain bag and a blood circuit.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP30011895A JP3440659B2 (en) | 1995-11-17 | 1995-11-17 | Antibacterial material and antibacterial molded product using the same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP30011895A JP3440659B2 (en) | 1995-11-17 | 1995-11-17 | Antibacterial material and antibacterial molded product using the same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH09135893A true JPH09135893A (en) | 1997-05-27 |
| JP3440659B2 JP3440659B2 (en) | 2003-08-25 |
Family
ID=17880945
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP30011895A Expired - Fee Related JP3440659B2 (en) | 1995-11-17 | 1995-11-17 | Antibacterial material and antibacterial molded product using the same |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP3440659B2 (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2001024868A1 (en) * | 1999-10-06 | 2001-04-12 | Kazuhiro Imai | Suppository-carrying instruments for inserting suppositories into human or animal body |
| US7105577B2 (en) | 1999-05-20 | 2006-09-12 | Ciba Specialty Chemicals Corporation | Antimicrobial method using a hydroxydiphenyl ether compound |
| JP2011521753A (en) * | 2008-06-04 | 2011-07-28 | エドワーズ ライフサイエンシーズ アイピーアールエム アーゲー | Apparatus for determining blood volume and / or blood volume flow and method of operating the same |
-
1995
- 1995-11-17 JP JP30011895A patent/JP3440659B2/en not_active Expired - Fee Related
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7105577B2 (en) | 1999-05-20 | 2006-09-12 | Ciba Specialty Chemicals Corporation | Antimicrobial method using a hydroxydiphenyl ether compound |
| WO2001024868A1 (en) * | 1999-10-06 | 2001-04-12 | Kazuhiro Imai | Suppository-carrying instruments for inserting suppositories into human or animal body |
| JP2011521753A (en) * | 2008-06-04 | 2011-07-28 | エドワーズ ライフサイエンシーズ アイピーアールエム アーゲー | Apparatus for determining blood volume and / or blood volume flow and method of operating the same |
Also Published As
| Publication number | Publication date |
|---|---|
| JP3440659B2 (en) | 2003-08-25 |
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