JPH0376343B2 - - Google Patents
Info
- Publication number
- JPH0376343B2 JPH0376343B2 JP58148453A JP14845383A JPH0376343B2 JP H0376343 B2 JPH0376343 B2 JP H0376343B2 JP 58148453 A JP58148453 A JP 58148453A JP 14845383 A JP14845383 A JP 14845383A JP H0376343 B2 JPH0376343 B2 JP H0376343B2
- Authority
- JP
- Japan
- Prior art keywords
- latex
- antibacterial
- parts
- composition
- acridine
- 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.)
- Expired - Lifetime
Links
- 229920000126 latex Polymers 0.000 claims description 46
- 239000004816 latex Substances 0.000 claims description 46
- 230000000844 anti-bacterial effect Effects 0.000 claims description 28
- 239000000203 mixture Substances 0.000 claims description 22
- DZBUGLKDJFMEHC-UHFFFAOYSA-N benzoquinolinylidene Natural products C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 claims description 13
- -1 acridine compound Chemical class 0.000 claims description 11
- 229920006173 natural rubber latex Polymers 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
- 229920001059 synthetic polymer Polymers 0.000 claims description 6
- NIMNIJHOINCSAH-UHFFFAOYSA-N 1-ethoxyacridine Chemical compound C1=CC=C2C=C3C(OCC)=CC=CC3=NC2=C1 NIMNIJHOINCSAH-UHFFFAOYSA-N 0.000 claims description 2
- XJGFWWJLMVZSIG-UHFFFAOYSA-N 9-aminoacridine Chemical compound C1=CC=C2C(N)=C(C=CC=C3)C3=NC2=C1 XJGFWWJLMVZSIG-UHFFFAOYSA-N 0.000 claims description 2
- WDVSHHCDHLJJJR-UHFFFAOYSA-N Proflavine Chemical compound C1=CC(N)=CC2=NC3=CC(N)=CC=C3C=C21 WDVSHHCDHLJJJR-UHFFFAOYSA-N 0.000 claims description 2
- 229960001441 aminoacridine Drugs 0.000 claims description 2
- 239000003242 anti bacterial agent Substances 0.000 description 11
- 238000000034 method Methods 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 239000007864 aqueous solution Substances 0.000 description 6
- 229920001577 copolymer Polymers 0.000 description 6
- 239000012153 distilled water Substances 0.000 description 6
- 239000000178 monomer Substances 0.000 description 6
- 239000002245 particle Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- 241000894006 Bacteria Species 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 235000013305 food Nutrition 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 230000002459 sustained effect Effects 0.000 description 4
- IYLLULUTZPKQBW-UHFFFAOYSA-N Acrinol Chemical compound CC(O)C(O)=O.C1=C(N)C=CC2=C(N)C3=CC(OCC)=CC=C3N=C21 IYLLULUTZPKQBW-UHFFFAOYSA-N 0.000 description 3
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 3
- 150000001251 acridines Chemical class 0.000 description 3
- 238000005054 agglomeration Methods 0.000 description 3
- 230000002776 aggregation Effects 0.000 description 3
- 125000000129 anionic group Chemical group 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 229920001971 elastomer Polymers 0.000 description 3
- 230000002485 urinary effect Effects 0.000 description 3
- 210000002700 urine Anatomy 0.000 description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- 229920002554 vinyl polymer Polymers 0.000 description 3
- SYUWDSSYDVWBGD-UHFFFAOYSA-N 7-ethoxyacridine-3,9-diamine;hydrochloride Chemical compound Cl.C1=C(N)C=CC2=C(N)C3=CC(OCC)=CC=C3N=C21 SYUWDSSYDVWBGD-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 244000043261 Hevea brasiliensis Species 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 2
- WSFHCKWLECYVBS-UHFFFAOYSA-N acridine-3,6-diamine;sulfuric acid Chemical compound OS(O)(=O)=O.C1=CC(N)=CC2=NC3=CC(N)=CC=C3C=C21 WSFHCKWLECYVBS-UHFFFAOYSA-N 0.000 description 2
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 2
- 239000003945 anionic surfactant Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000000084 colloidal system Substances 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 150000001993 dienes Chemical class 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 238000001879 gelation Methods 0.000 description 2
- 229920001519 homopolymer Polymers 0.000 description 2
- 230000002209 hydrophobic effect Effects 0.000 description 2
- 208000015181 infectious disease Diseases 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 229920003052 natural elastomer Polymers 0.000 description 2
- 229920001194 natural rubber Polymers 0.000 description 2
- 230000001681 protective effect Effects 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- PRBHEGAFLDMLAL-UHFFFAOYSA-N 1,5-Hexadiene Natural products CC=CCC=C PRBHEGAFLDMLAL-UHFFFAOYSA-N 0.000 description 1
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 1
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical compound C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 description 1
- FTGPOQQGJVJDCT-UHFFFAOYSA-N 9-aminoacridine hydrochloride Chemical compound Cl.C1=CC=C2C(N)=C(C=CC=C3)C3=NC2=C1 FTGPOQQGJVJDCT-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- 241001156739 Actinobacteria <phylum> Species 0.000 description 1
- 244000063299 Bacillus subtilis Species 0.000 description 1
- 235000014469 Bacillus subtilis Nutrition 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 244000286663 Ficus elastica Species 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical class CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- 241001467460 Myxogastria Species 0.000 description 1
- 206010037596 Pyelonephritis Diseases 0.000 description 1
- 239000004902 Softening Agent Substances 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- 241000700605 Viruses Species 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000004018 acid anhydride group Chemical group 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 230000003712 anti-aging effect Effects 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 210000001124 body fluid Anatomy 0.000 description 1
- 239000010839 body fluid Substances 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000003093 cationic surfactant Substances 0.000 description 1
- YACLQRRMGMJLJV-UHFFFAOYSA-N chloroprene Chemical compound ClC(=C)C=C YACLQRRMGMJLJV-UHFFFAOYSA-N 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 201000003146 cystitis Diseases 0.000 description 1
- 239000000645 desinfectant Substances 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 239000002612 dispersion medium Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000004070 electrodeposition Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- CIKWKGFPFXJVGW-UHFFFAOYSA-N ethacridine Chemical compound C1=C(N)C=CC2=C(N)C3=CC(OCC)=CC=C3N=C21 CIKWKGFPFXJVGW-UHFFFAOYSA-N 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 238000007667 floating Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- GEAWFZNTIFJMHR-UHFFFAOYSA-N hepta-1,6-diene Chemical compound C=CCCCC=C GEAWFZNTIFJMHR-UHFFFAOYSA-N 0.000 description 1
- PYGSKMBEVAICCR-UHFFFAOYSA-N hexa-1,5-diene Chemical compound C=CCCC=C PYGSKMBEVAICCR-UHFFFAOYSA-N 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 230000002427 irreversible effect Effects 0.000 description 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 239000002075 main ingredient Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- XMYQHJDBLRZMLW-UHFFFAOYSA-N methanolamine Chemical group NCO XMYQHJDBLRZMLW-UHFFFAOYSA-N 0.000 description 1
- XJRBAMWJDBPFIM-UHFFFAOYSA-N methyl vinyl ether Chemical compound COC=C XJRBAMWJDBPFIM-UHFFFAOYSA-N 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 239000004745 nonwoven fabric Substances 0.000 description 1
- 239000006916 nutrient agar Substances 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 229920002432 poly(vinyl methyl ether) polymer Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 201000004537 pyelitis Diseases 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 238000004513 sizing Methods 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 208000000143 urethritis Diseases 0.000 description 1
- 210000001635 urinary tract Anatomy 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 235000014692 zinc oxide Nutrition 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Landscapes
- Materials For Medical Uses (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Description
【発明の詳細な説明】
本発明は、抗菌性ラテツクス組成物に関するも
のであり、その目的とするところは持続的な抗菌
活性を有する医療器具、衛生用品、食品製造用機
器又は備品等のラテツクス成型品を製造するに好
適な抗菌性ラテツクス組成物を提案するところに
ある。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to an antibacterial latex composition, and its purpose is to mold latex for medical instruments, sanitary products, food manufacturing equipment, supplies, etc., which have sustained antibacterial activity. The purpose of this invention is to propose an antibacterial latex composition suitable for manufacturing products.
従来から医療、衛生、検査あるいは食品分野に
おいては、種々雑多な細菌、放射菌、真菌、粘菌
あるいはウイルス等からの汚染や感染を防止する
ために、種々の殺菌消毒剤が用いられている。な
かでも、6,9−ジアミノ−2−エトキシアルク
リジンの乳酸塩(別名アクリノールともいう。)
に代表されるアクリジン化合物は、広い範囲の微
生物に強力な殺菌力を有し、かつ人体に対する毒
性も低いところから、今日、数ある抗菌剤の中で
も最も広く使用されている殺菌消毒剤の一つであ
る。現在、これらは通常、水溶液として提供され
るため、医療器具等は使用に先立ちこ水溶液に浸
漬するか又波あはこの水溶液を噴霧することによ
り、一応所期の目的を達せられている。 Conventionally, various sterilizing disinfectants have been used in the fields of medicine, hygiene, testing, and food to prevent contamination and infection from various types of bacteria, actinobacteria, fungi, slime molds, viruses, and the like. Among them, 6,9-diamino-2-ethoxyalklidine lactate (also called acrinol)
Acridine compounds are one of the most widely used antibacterial agents today, as they have strong bactericidal activity against a wide range of microorganisms and have low toxicity to the human body. It is. Currently, these are usually provided as an aqueous solution, and the desired purpose can be achieved by immersing medical instruments in the aqueous solution or spraying the aqueous solution on them before use.
しかし、医療器具等を長期間にわたり使用する
場合には、初期の消毒のみでは抗菌剤としての効
力が次第に低下ないし消失することは、我々が日
常しばしば経験するところであり、その改善が強
く望まれている。 However, when medical instruments are used for a long period of time, we often experience in our daily lives that the effectiveness of antibacterial agents gradually decreases or disappears if only the initial disinfection is carried out, and there is a strong desire to improve this situation. There is.
その最も有応な対策としてその使用過程におい
て、上記器具中より最小(発育)阻止濃度以上の
抗菌剤が一定量ずつ徐放されるシステムが考えら
れる。このようなシステムの実現のためには、抗
菌剤が均一かつ安定に分散したラテツクスを得、
このものを、例えば医療器具等に成型することが
必要であるが、アクリジン化合物が均一かつ安定
に分散したラテツクスは、以下に述べるように、
これまで得られていない。 The most appropriate countermeasure would be a system in which a constant amount of antibacterial agent at a minimum (growth) inhibitory concentration or higher is slowly released from the device during the course of its use. In order to realize such a system, it is necessary to obtain latex in which antibacterial agents are uniformly and stably dispersed.
It is necessary to mold this material into, for example, a medical device, etc., but the latex in which the acridine compound is uniformly and stably dispersed can be
It has not been obtained so far.
まず、疎水性いの天然ゴム又は合成高分子化合
物を水媒体中に分散させた高分子ラテツクスは、
今日、種々の有用な用地に用いられているが、通
常、これらのラテツクス中にはラテツクス粒子の
安定な浮遊分散を助けるために各種界面活性剤や
保護コロイド等が含まれている。例えば天然ゴム
ラテツクスにおいては、その成分中に含まれる両
性電解質であるタンパク質がゴム粒子の表面に吸
着することにより一種の保護コロイド的な役割を
果たし、ラテツクス粒子の安定な分散を助けてい
る。また、天然ゴムラテツクスは、その中に含ま
れている酵素や細菌の作用で酸を生じて凝固しや
すいので、通常、これを防ぐため0.5〜1.0%のア
ンモニアが添加され、益はアルカリ性を保つてい
る。したがつてゴム粒子は基本的には負に帯電す
ることにより、粒子間相互の静電気的な反撥力に
より凝集することなく安定に浮遊分散しているこ
とになる。また、合成高分子系ラテツクスにおい
ても重合前又は重合後にアニオン系あるいは/及
びノニオン系界面活性剤が添加れており、実用的
には特別な事情がない限りカチオン系界面活性剤
が用いられている例ば極めて少ない。一方、抗菌
剤としてのアクリジン化合物は、その化学構造か
らもわかるように、一分子内に正電荷と疎水性環
状構造をもつカチオン型殺菌剤に属し、したがつ
て、例えば市販品である6,9−ジアミノ−2−
エトキシアクリジンの易水溶性の塩である乳酸塩
の水溶液にアニオン系界面活性剤である石鹸等を
加えることは、乳酸の脱離又は置換をもたらし、
難水溶性の塩を形成し、その結果、殺菌力の低下
をもたらすため従来より配合禁忌とされている。 First, polymer latex, which is made by dispersing hydrophobic natural rubber or synthetic polymer compounds in an aqueous medium, is
These latexes are used in a variety of useful applications today, and these latexes usually contain various surfactants, protective colloids, etc. to help stabilize the floating and dispersion of latex particles. For example, in natural rubber latex, protein, which is an ampholyte contained in its components, is adsorbed onto the surface of rubber particles, thereby acting as a kind of protective colloid and helping to stabilize the dispersion of latex particles. In addition, natural rubber latex tends to generate acid and coagulate due to the action of enzymes and bacteria contained in it, so to prevent this, 0.5 to 1.0% ammonia is usually added, and the benefit is to maintain alkalinity. There is. Therefore, since the rubber particles are basically negatively charged, they are stably suspended and dispersed without agglomerating due to the mutual electrostatic repulsion between the particles. In addition, anionic and/or nonionic surfactants are added to synthetic polymer latexes before or after polymerization, and in practice, cationic surfactants are used unless there are special circumstances. For example, very few. On the other hand, as can be seen from its chemical structure, acridine compounds as antibacterial agents belong to cationic fungicides that have a positive charge and a hydrophobic ring structure in one molecule, and therefore, for example, commercially available products such as 6, 9-diamino-2-
Adding an anionic surfactant such as soap to an aqueous solution of lactate, which is a readily water-soluble salt of ethoxyacridine, causes the elimination or replacement of lactic acid.
It has been considered contraindicated in the past because it forms poorly water-soluble salts, resulting in a decrease in bactericidal activity.
以上のような技術的背景の下においては、例え
ばアクリノール水溶液を天然ゴムラエツクスに加
えると、ラテツクス粒子の負荷電が中和され、か
つ不安定化される結果、ラテツクスは直ちに不可
逆的なゲル化を起こすため、これらアクリジン系
抗菌剤をラテツクスに添加することあ、従来、非
常識とされ、それ以上真剣に検討が加えられるこ
とはななつた。 Under the above technical background, for example, when an aqueous acrinol solution is added to natural rubber latex, the negative charge of the latex particles is neutralized and destabilized, resulting in immediate irreversible gelation of the latex. Therefore, the addition of these acridine-based antibacterial agents to latex was considered to be nonsense, and no further serious consideration was given.
本発明者らは、持続的な抗菌活性を有するラテ
ツクスから成る医療器具、衛生用品、食品製造用
備品等を製造するに好適な抗菌性ラテツクス組成
物について鋭意検討を進めた結果、驚くべきこと
に難水溶性かつ抗菌性のアクリジン化合物又はそ
の塩を上記ラテツクス中に加えてもゲル化を起こ
すことなく安定した抗菌性ラテツクス組成物が得
らえることを見い出し、本発明に到達したもので
ある。 The present inventors have conducted intensive studies on antibacterial latex compositions suitable for manufacturing medical devices, sanitary products, food manufacturing equipment, etc. made of latex with sustained antibacterial activity, and have surprisingly found that The present invention has been achieved based on the discovery that a stable antibacterial latex composition can be obtained without causing gelation even if a poorly water-soluble and antibacterial acridine compound or its salt is added to the latex.
すなわち本発明は、天然ゴムラテツクス又は合
成高分子ラテツクスと、難水溶性かつ抗菌性のア
クリジン化合物又はその塩とを配合してなる抗菌
性ラテツクス組成物である。 That is, the present invention is an antibacterial latex composition comprising natural rubber latex or synthetic polymer latex and a poorly water-soluble and antibacterial acridine compound or its salt.
本発明におけるアクリジン化合物とは、下記の
アクリジン骨格を有する化合物であり、「大有機
化学」第16巻
286〜326頁(朝倉書店、昭和34年)に種々の誘導
体が記載されている。かかるアクリジン化合物の
好適な具体例として9−アミノアクリジン、3,
6−ジアミノアクリジン、6,9−ジアミノ−2
−エトキシアクリジン等があげられる。 The acridine compound in the present invention is a compound having the following acridine skeleton, and is a compound having the following acridine skeleton. Various derivatives are described on pages 286-326 (Asakura Shoten, 1960). Preferred specific examples of such acridine compounds include 9-aminoacridine, 3,
6-diaminoacridine, 6,9-diamino-2
-Ethoxyacridine and the like.
本発明におけるアクリジン化合物の塩とは、ア
クリジン化合物と、無機酸もしくは有機酸とから
形成される塩をいう。 The salt of an acridine compound in the present invention refers to a salt formed from an acridine compound and an inorganic acid or an organic acid.
本発明にいう難水溶性とは、20℃における100
gの蒸溜水に対する溶解度が0.001〜1.0g、好ま
しくは0.005〜0.7gの範囲のものを指す。水に対
する溶解度が0.001g未満では殺菌剤としての効
力が減退し、一方1.0gをこえるとラテツクス中
に加えた時ラテツクスの不可逆的なゲル化を起こ
し好ましくない。 Poor water solubility in the present invention means 100%
The solubility in distilled water is 0.001 to 1.0 g, preferably 0.005 to 0.7 g. If the solubility in water is less than 0.001 g, the efficacy as a bactericidal agent will be reduced, while if it exceeds 1.0 g, the latex will irreversibly gel when added to the latex, which is undesirable.
本発明における抗菌性ラテツクス組成物におけ
る難水溶性かつ抗菌性のアクリジン化合物又はそ
の塩の含有量は、その目的とするところにより異
なるが、通常、ラテツクスの固形分に対して好ま
しくは0.01〜30wt%、より好ましくは0.1〜10wt
%である。含有量が30wt%をこえる場合は、こ
のラテツクス組成物より得られた成型品の皮膜の
物理的強度が劣る傾向があり、一方、0.01wt%未
満では抗菌剤としての効力を発揮しにくくなるの
で好ましくない。 The content of the poorly water-soluble and antibacterial acridine compound or its salt in the antibacterial latex composition of the present invention varies depending on the purpose, but is usually preferably 0.01 to 30 wt% based on the solid content of the latex. , more preferably 0.1~10wt
%. If the content exceeds 30wt%, the physical strength of the film of the molded product obtained from this latex composition tends to be poor, while if it is less than 0.01wt%, it becomes difficult to exert its effectiveness as an antibacterial agent. Undesirable.
本発明に用いられる天然ゴムラテツクスとは、
ゴム植物の樹皮に切付を行つた時に流れ出る種々
の有機物及び無機物を含有した水溶液を分散媒体
とし、ゴム分を分散質とし、必要に応じてPH調整
剤、加硫剤、加硫促進剤、軟化剤、充填剤、老化
防止剤、着色剤等を配合したものをいう。また、
合成高分子系ラテツクスとしては、例えばエチレ
ン、スチレン、酢酸ビニル、塩化ビニル、塩化ビ
ニリデン、アクリロニトリル、(メタ)アクリル
酸エステル、ビニルピリジン、メチルビニルエー
テル等のビニル系モノマーの単一重合体又はその
共重合体、ブタジエン、イソプレン、1,3−ペ
ンタエシ、1,5−ヘキサジエン、1,6−ヘプ
タジエン、クロロプレン等のジエン系モノマーの
単一重合体あるいはその共重合体、上記ビニル系
モノマーとジエン系モノマーの共重合体、その他
官能基としてエポキシド基、アミノ基、カルボキ
シル基、酸無水物基、水酸基、アミド基、N−メ
チロールアミド基、イソシアネート基等を有する
ビニル系モノマーと上記各種モノマーとの共重合
体等を主成分とし、必要に応じて界面活性剤、架
橋剤、充填剤、軟化剤等を配合したものがあげら
れる。 The natural rubber latex used in the present invention is
The dispersion medium is an aqueous solution containing various organic and inorganic substances that flows out when the bark of a rubber plant is cut, and the rubber component is used as the dispersoid. This refers to products that contain softeners, fillers, anti-aging agents, colorants, etc. Also,
Examples of synthetic polymer latexes include homopolymers of vinyl monomers such as ethylene, styrene, vinyl acetate, vinyl chloride, vinylidene chloride, acrylonitrile, (meth)acrylic acid esters, vinyl pyridine, and methyl vinyl ether, or copolymers thereof. , homopolymers of diene monomers such as butadiene, isoprene, 1,3-pentaethyl, 1,5-hexadiene, 1,6-heptadiene, chloroprene, etc., or copolymers thereof, copolymers of the above vinyl monomers and diene monomers. Copolymers, etc. of vinyl monomers having other functional groups such as epoxide groups, amino groups, carboxyl groups, acid anhydride groups, hydroxyl groups, amide groups, N-methylolamide groups, isocyanate groups, and the above various monomers. Examples include those containing a surfactant, a crosslinking agent, a filler, a softening agent, etc. as the main ingredient.
本発明の抗菌性ラテツクス組成物を調整する方
法は、各成分が均一に混合される方法であれば特
に限定されず、公知の種々の方法を利用すること
ができるが、例えば抗菌剤をボールミウ内で摩砕
しながら均一なペースト状水分散物とし、これに
天然ゴムラテツクス又は合成高分子ラテツクスを
加えて撹拌混合するなどの方法が好ましく採用さ
れる。 The method for preparing the antibacterial latex composition of the present invention is not particularly limited as long as each component is mixed uniformly, and various known methods can be used. Preferably, a method is employed in which a homogeneous paste-like aqueous dispersion is obtained by grinding with a grinder, and natural rubber latex or synthetic polymer latex is added thereto and mixed by stirring.
本発明の抗菌性ラテツクス組成物は、長期の使
用過程においても持続的な抗菌性を有する医療器
具、衛生器具、食品製造用機器又は備品等の成型
加工に好適に用いられる。具体的な成型品の例と
しては、導尿カテーテルをはじめとする各種カテ
ーテル類、蓄尿バツク等のバツク類、給排液チユ
ーブ、スポンジ、ゴム引布、紙のサイジング剤、
不織布のバインダー、塗料、接着剤等があげられ
る。これらは従来公知の浸漬法、キヤステイング
法又は電着法等により成型される。さらに具体的
な応用例をあげるならば、長期間における体内留
置においてカテーテルを通じて侵入する細菌によ
り尿道炎、膀胱炎、腎う炎等が頻発する導尿カテ
ーテルについて、本発明の抗菌性ラテツクス組成
物を用いて成型された導尿カテーテルや蓄尿バツ
クは抗菌剤を徐放する性能を有し、その使用過程
において尿又は体液により抗菌剤が持続的に徐放
されるので、種々の細菌からの尿路感染を防止す
る上で極めて効果的である。 The antibacterial latex composition of the present invention can be suitably used for molding medical instruments, sanitary instruments, food manufacturing equipment or fixtures, etc., which have sustained antibacterial properties even during long-term use. Examples of specific molded products include various catheters including urinary catheters, bags such as urine storage bags, fluid supply and drainage tubes, sponges, rubberized cloth, paper sizing agents,
Examples include non-woven fabric binders, paints, adhesives, etc. These are molded by a conventionally known dipping method, casting method, electrodeposition method, or the like. To give a more specific application example, the antibacterial latex composition of the present invention can be used for urinary catheters, which frequently cause urethritis, cystitis, pyelitis, etc. due to bacteria that enter through the catheter when left in the body for a long period of time. The molded urinary catheter and urine storage bag have the ability to release antibacterial agents in a sustained manner, and during the process of use, the antibacterial agents are continuously released in urine or body fluids, so they can be used to protect the urinary tract from various bacteria. Extremely effective in preventing infection.
以下に具体的な実施例を記し本発明を詳述す
る。 The present invention will be described in detail with reference to specific examples below.
なお、例中の「部」は「重量部」を意味する。 Note that "parts" in the examples mean "parts by weight."
実施例 1
固形分濃度が約50wt%の天然ゴムラテツクス
溶液(PH10.7)100部に、ジメチルジチオカルバ
ミンサ酸亜鉛0.3部、硫黄1.5部、亜鉛華3部及び
ステアリン酸1.2部を加え、均一に分散させて天
然ゴムを主成分とする配合ラテツクスを得た。こ
の配合ラテツクスに、抗菌剤として6,9−ジア
ミノ−2−エトキシアクリジンの塩酸塩10部をあ
らかじめ蒸溜水12部にペースト状に均一に分散さ
せたものを撹拌しながら加えたところ、ラテツク
スは凝集することなく、抗菌剤が均一に分散した
ラテツクス組成物を得ることができた。Example 1 0.3 parts of zinc dimethyldithiocarbaminsate, 1.5 parts of sulfur, 3 parts of zinc white, and 1.2 parts of stearic acid were added to 100 parts of a natural rubber latex solution (PH10.7) with a solid content concentration of approximately 50 wt%, and uniformly dispersed. A compounded latex containing natural rubber as the main component was obtained. When 10 parts of 6,9-diamino-2-ethoxyacridine hydrochloride as an antibacterial agent was uniformly dispersed into a paste in 12 parts of distilled water to this mixed latex while stirring, the latex coagulated. It was possible to obtain a latex composition in which the antibacterial agent was uniformly dispersed without having to do so.
得られた組成物からはフイルムを成型すること
ができ、このフイルムについてBacillus Subtilis
ATCC6633(培地NUTRIENT AGAR)を検定
菌として円筒平板法(デイスク法)により抗菌活
性テストを行つたところ阻止円を生じ、の組成物
が抗菌性を有することが認められた。 A film can be formed from the obtained composition, and about this film, Bacillus subtilis
When an antibacterial activity test was conducted using ATCC6633 (medium NUTRIENT AGAR) as a test bacterium by the cylindrical plate method (disk method), an inhibition circle was produced, and the composition was confirmed to have antibacterial properties.
比較例 1
実施例1で用いたと同じ配合ラテツクス100部
に、6,9−ジアミノ−2−エトキシアクリジン
乳酸塩の1.5wt%水溶液を撹拌しながら少しずつ
加えたところ、ラテツクスは徐々に粘性を増し、
およそ5ml加えたところで完全にゲル化した。Comparative Example 1 When a 1.5 wt% aqueous solution of 6,9-diamino-2-ethoxyacridine lactate was added little by little to 100 parts of the same compounded latex used in Example 1 while stirring, the latex gradually increased in viscosity. ,
After approximately 5 ml was added, the mixture completely gelled.
実施例 2
実施例1で用いたと同じ配合ラテツクス100部
に、9−アミノアクリジンの塩酸塩10部をあらか
じめ蒸溜水12部にペースト状に分散させたものを
撹拌しながら加えたところ、ラテツクスは凝集す
ることなく均一に分散した。Example 2 To 100 parts of the same mixed latex used in Example 1, 10 parts of 9-aminoacridine hydrochloride was dispersed in paste form in 12 parts of distilled water, and this was added with stirring, and the latex agglomerated. It was evenly dispersed without any smudging.
得られた組成物について実施例1と同様の試験
を行つたところ、フイルムは抗菌性を示した。 When the obtained composition was subjected to the same test as in Example 1, the film showed antibacterial properties.
実施例 3
実施例1で用いたと同じ配合ラテツクス100部
に、3,6−ジアミノアクリジンの硫酸塩10部を
あらかじ蒸溜水12部にペースト状に均一に分散さ
せたものを撹拌しながら加えたところ、ラテツス
クは凝集することなく均一に分散した。Example 3 To 100 parts of the same mixed latex used in Example 1, 10 parts of 3,6-diaminoacridine sulfate was uniformly dispersed in a paste form in 12 parts of distilled water, and this was added with stirring. However, the latex was uniformly dispersed without agglomeration.
得られた組成物について実施施例1と同様の試
験を行つたところフイルムは抗菌性を示した。 When the obtained composition was subjected to the same test as in Example 1, the film showed antibacterial properties.
実施例 4
固形分濃度約50wt%のアニオン性スチレン−
ブタジエン共重合体ラテツクス(PH=9.5)100部
に、6,9−ジアミノ−2−エトキシアクリジン
の塩酸塩10部をあらかじめ蒸溜水12部に均一に分
散させものを撹拌しながら加えたところ、ラテツ
クスは凝集することなく均一に分散した。Example 4 Anionic styrene with a solid content concentration of approximately 50 wt%
When 10 parts of 6,9-diamino-2-ethoxyacridine hydrochloride was uniformly dispersed in 12 parts of distilled water and added to 100 parts of butadiene copolymer latex (PH=9.5) while stirring, the latex was uniformly dispersed without agglomeration.
得られた組成物について実施例1と同様の試験
を行つたところフイルムは抗菌性を示した。 When the obtained composition was subjected to the same test as in Example 1, the film showed antibacterial properties.
実施例 5
固形分濃度約45wt%のアニオン性塩化ビニル
−塩化ビニリデン共重合体ラテツクス(PH=9.0)
100部に、3,6−ジアミノアクリジンの硫酸塩
10部をあらかじめ蒸溜水12部に均一に分散したも
のを加えたところ、上記ラテツクス溶液は凝集す
ることなく均一に分散した。Example 5 Anionic vinyl chloride-vinylidene chloride copolymer latex with a solid content concentration of approximately 45 wt% (PH = 9.0)
100 parts of 3,6-diaminoacridine sulfate
When 10 parts of the latex solution was uniformly dispersed in 12 parts of distilled water, the latex solution was uniformly dispersed without agglomeration.
得られた組成物につて実施例1と同様に試験を
行なつたところフイルムは抗菌性を示した。 When the resulting composition was tested in the same manner as in Example 1, the film showed antibacterial properties.
Claims (1)
スと、難水溶性かつ抗菌性のアクリジン化合物又
はその塩とを配合してなる抗菌性ラテツクス組成
物。 2 アクリジン化合物が9−アミノアクリジンで
ある特許請求の範囲第1項記載の抗菌性ラテツク
ス組成物。 3 アクリジン化合物が、3,6−ジアミノアク
リジンである特許請求の範囲第1項記載の抗菌性
ラテツクス組成物。 4 アクリジン化合物が6,9−ジアミノ−2−
エトキシアクリジンである特許請求の範囲第1項
記載の抗菌性ラテツクス組成物。[Scope of Claims] 1. An antibacterial latex composition comprising natural rubber latex or synthetic polymer latex and a sparingly water-soluble and antibacterial acridine compound or its salt. 2. The antibacterial latex composition according to claim 1, wherein the acridine compound is 9-aminoacridine. 3. The antibacterial latex composition according to claim 1, wherein the acridine compound is 3,6-diaminoacridine. 4 The acridine compound is 6,9-diamino-2-
The antibacterial latex composition according to claim 1, which is ethoxyacridine.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP58148453A JPS6040139A (en) | 1983-08-12 | 1983-08-12 | Antimicrobial latex composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP58148453A JPS6040139A (en) | 1983-08-12 | 1983-08-12 | Antimicrobial latex composition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6040139A JPS6040139A (en) | 1985-03-02 |
| JPH0376343B2 true JPH0376343B2 (en) | 1991-12-05 |
Family
ID=15453108
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP58148453A Granted JPS6040139A (en) | 1983-08-12 | 1983-08-12 | Antimicrobial latex composition |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6040139A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0781566A2 (en) | 1995-12-26 | 1997-07-02 | Toyo Boseki Kabushiki Kaisha | Organic solvent-soluble mucopolysaccharide, antibacterial antithrombogenic composition and medical material |
-
1983
- 1983-08-12 JP JP58148453A patent/JPS6040139A/en active Granted
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0781566A2 (en) | 1995-12-26 | 1997-07-02 | Toyo Boseki Kabushiki Kaisha | Organic solvent-soluble mucopolysaccharide, antibacterial antithrombogenic composition and medical material |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6040139A (en) | 1985-03-02 |
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