JPH025956A - Antifungal and antimoulding method for plastic product - Google Patents
Antifungal and antimoulding method for plastic productInfo
- Publication number
- JPH025956A JPH025956A JP15484088A JP15484088A JPH025956A JP H025956 A JPH025956 A JP H025956A JP 15484088 A JP15484088 A JP 15484088A JP 15484088 A JP15484088 A JP 15484088A JP H025956 A JPH025956 A JP H025956A
- Authority
- JP
- Japan
- Prior art keywords
- resin
- bis
- plastic product
- antifungal
- compounds
- 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
- 229920003023 plastic Polymers 0.000 title claims abstract description 27
- 239000004033 plastic Substances 0.000 title claims abstract description 27
- 229940121375 antifungal agent Drugs 0.000 title claims abstract description 13
- 238000000034 method Methods 0.000 title claims abstract description 8
- 230000000843 anti-fungal effect Effects 0.000 title claims abstract description 6
- KDPAWGWELVVRCH-UHFFFAOYSA-N bromoacetic acid Chemical class OC(=O)CBr KDPAWGWELVVRCH-UHFFFAOYSA-N 0.000 claims abstract 3
- 230000000844 anti-bacterial effect Effects 0.000 claims description 18
- 239000000126 substance Substances 0.000 claims description 9
- SIHKVAXULDBIIY-UHFFFAOYSA-N 4-(2-bromoacetyl)oxybut-2-enyl 2-bromoacetate Chemical compound BrCC(=O)OCC=CCOC(=O)CBr SIHKVAXULDBIIY-UHFFFAOYSA-N 0.000 claims description 4
- 244000052616 bacterial pathogen Species 0.000 claims 1
- 241000894007 species Species 0.000 claims 1
- 229920005989 resin Polymers 0.000 abstract description 24
- 239000011347 resin Substances 0.000 abstract description 24
- 150000001875 compounds Chemical class 0.000 abstract description 12
- 238000004519 manufacturing process Methods 0.000 abstract description 9
- -1 polypropylene Polymers 0.000 abstract description 9
- 239000004014 plasticizer Substances 0.000 abstract description 7
- 244000005700 microbiome Species 0.000 abstract description 6
- 239000007788 liquid Substances 0.000 abstract description 5
- 238000011109 contamination Methods 0.000 abstract description 3
- 239000004743 Polypropylene Substances 0.000 abstract description 2
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 abstract description 2
- 229920002857 polybutadiene Polymers 0.000 abstract description 2
- 229920013716 polyethylene resin Polymers 0.000 abstract description 2
- 229920001155 polypropylene Polymers 0.000 abstract description 2
- 229920005990 polystyrene resin Polymers 0.000 abstract description 2
- 229920005749 polyurethane resin Polymers 0.000 abstract description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 abstract description 2
- 239000005062 Polybutadiene Substances 0.000 abstract 1
- 125000002573 ethenylidene group Chemical group [*]=C=C([H])[H] 0.000 abstract 1
- 238000012360 testing method Methods 0.000 description 22
- 241000894006 Bacteria Species 0.000 description 10
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 10
- 241000195493 Cryptophyta Species 0.000 description 8
- 229920001817 Agar Polymers 0.000 description 7
- 239000004698 Polyethylene Substances 0.000 description 7
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 7
- 239000008272 agar Substances 0.000 description 7
- 239000003242 anti bacterial agent Substances 0.000 description 7
- 239000003429 antifungal agent Substances 0.000 description 7
- 229920000573 polyethylene Polymers 0.000 description 7
- 229940079593 drug Drugs 0.000 description 6
- 239000003814 drug Substances 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 5
- 230000000813 microbial effect Effects 0.000 description 5
- NCDBYAPSWOPDRN-UHFFFAOYSA-N 2-[dichloro(fluoro)methyl]sulfanylisoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(SC(Cl)(Cl)F)C(=O)C2=C1 NCDBYAPSWOPDRN-UHFFFAOYSA-N 0.000 description 4
- 241000233866 Fungi Species 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 230000012010 growth Effects 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- MQIUGAXCHLFZKX-UHFFFAOYSA-N Di-n-octyl phthalate Natural products CCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC MQIUGAXCHLFZKX-UHFFFAOYSA-N 0.000 description 3
- YSMRWXYRXBRSND-UHFFFAOYSA-N TOTP Chemical compound CC1=CC=CC=C1OP(=O)(OC=1C(=CC=CC=1)C)OC1=CC=CC=C1C YSMRWXYRXBRSND-UHFFFAOYSA-N 0.000 description 3
- SIHKVAXULDBIIY-OWOJBTEDSA-N [(e)-4-(2-bromoacetyl)oxybut-2-enyl] 2-bromoacetate Chemical compound BrCC(=O)OC\C=C\COC(=O)CBr SIHKVAXULDBIIY-OWOJBTEDSA-N 0.000 description 3
- BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 description 3
- 230000006866 deterioration Effects 0.000 description 3
- 230000002538 fungal effect Effects 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 238000007711 solidification Methods 0.000 description 3
- 230000008023 solidification Effects 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- YEVQZPWSVWZAOB-UHFFFAOYSA-N 2-(bromomethyl)-1-iodo-4-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=C(I)C(CBr)=C1 YEVQZPWSVWZAOB-UHFFFAOYSA-N 0.000 description 2
- 240000009108 Chlorella vulgaris Species 0.000 description 2
- 235000007089 Chlorella vulgaris Nutrition 0.000 description 2
- 102100023991 E3 ubiquitin-protein ligase DTX3L Human genes 0.000 description 2
- 101000904542 Homo sapiens E3 ubiquitin-protein ligase DTX3L Proteins 0.000 description 2
- 244000061456 Solanum tuberosum Species 0.000 description 2
- 235000002595 Solanum tuberosum Nutrition 0.000 description 2
- 230000005791 algae growth Effects 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 230000006378 damage Effects 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 239000012770 industrial material Substances 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 230000002265 prevention Effects 0.000 description 2
- 238000013112 stability test Methods 0.000 description 2
- WJCNZQLZVWNLKY-UHFFFAOYSA-N thiabendazole Chemical compound S1C=NC(C=2NC3=CC=CC=C3N=2)=C1 WJCNZQLZVWNLKY-UHFFFAOYSA-N 0.000 description 2
- AFSROBHYIMWVTR-UHFFFAOYSA-N 1-(2-bromoacetyl)oxyethyl 2-bromoacetate Chemical compound BrCC(=O)OC(C)OC(=O)CBr AFSROBHYIMWVTR-UHFFFAOYSA-N 0.000 description 1
- 241001209435 Actus Species 0.000 description 1
- 241000588986 Alcaligenes Species 0.000 description 1
- 241000192542 Anabaena Species 0.000 description 1
- 241000228212 Aspergillus Species 0.000 description 1
- 241000193830 Bacillus <bacterium> Species 0.000 description 1
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical group C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 1
- 241000233732 Fusarium verticillioides Species 0.000 description 1
- 241000282412 Homo Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000228153 Penicillium citrinum Species 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 241000589516 Pseudomonas Species 0.000 description 1
- 229920000297 Rayon Polymers 0.000 description 1
- 241000223254 Rhodotorula mucilaginosa Species 0.000 description 1
- 241000195663 Scenedesmus Species 0.000 description 1
- 241001497549 Scenedesmus acutus Species 0.000 description 1
- 241000223261 Trichoderma viride Species 0.000 description 1
- 208000027418 Wounds and injury Diseases 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000004566 building material Substances 0.000 description 1
- 239000013043 chemical agent Substances 0.000 description 1
- 239000000498 cooling water Substances 0.000 description 1
- 238000012258 culturing Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- 230000009036 growth inhibition Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 208000014674 injury Diseases 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 230000009965 odorless effect Effects 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000005022 packaging material Substances 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000000088 plastic resin Substances 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Landscapes
- Apparatus For Disinfection Or Sterilisation (AREA)
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明はプラスチック製品の防菌病カビ方法および防菌
病カビされたプラスチック製品に関する。DETAILED DESCRIPTION OF THE INVENTION [Industrial Field of Application] The present invention relates to a method for preventing mold and mildew on plastic products and a plastic product treated with mold and mildew.
近年、プラスチックが建築材料、電子・電気関係部品、
家庭用製品等に多量に使用されるようになったが、これ
らのプラスチック製品に細菌類、カビ類、酵母類、藻類
の微生物が繁殖し、プラスチック樹脂の変形、分解など
の材料基質の劣化や、美観上の汚損など各種トラブルが
多発している。In recent years, plastics have been used as building materials, electronic and electrical parts,
These plastic products are now used in large quantities in household products, but microorganisms such as bacteria, mold, yeast, and algae can grow on these products, causing deterioration of the material matrix such as deformation and decomposition of the plastic resin. , various problems such as aesthetic deterioration are occurring frequently.
対象となる樹脂製品の例としては２例えばポリスチレン
製の電気部品、家紅用品、ポリエチレン製のフィルム、
パイプ、家庭用品、各種工業用材料・部品、ポリウレタ
ン製の自動車用品、フオーム、ｊ！工化ビニル製の７ｔ
ｌｆ線被覆材料、パイプ、農業用フィルム、レザー、シ
ートなどであり、各種プラスチック製の工業用材料・部
品、家庭用品、本務用品、電気用材料・部品、各種包装
材料等である。Examples of applicable resin products include polystyrene electrical parts, household appliances, polyethylene films,
Pipes, household goods, various industrial materials and parts, polyurethane automotive goods, foam, j! 7 tons made of engineered vinyl
These include LF ray covering materials, pipes, agricultural films, leather, sheets, etc., as well as various plastic industrial materials and parts, household goods, household goods, electrical materials and parts, and various packaging materials.
これらプラスチック製品の微生物による変質防止のため
に、各種の防菌防カビ剤が研究され、２−（４′−チア
ゾリル）−ベンツイミダゾール、 Ｎ−（フルオロジク
ロロメチルチオ）−フタルイミド、Ｎ、Ｎ−ジメチル−
Ｎ′＝（フルオロジクロルメチルチオ）−Ｎ’−フェニ
ルスルファミド等の化合物が開発され、使用されるよう
になった。In order to prevent deterioration of these plastic products by microorganisms, various antibacterial and antifungal agents have been researched, including 2-(4'-thiazolyl)-benzimidazole, N-(fluorodichloromethylthio)-phthalimide, N,N-dimethyl −
Compounds such as N'=(fluorodichloromethylthio)-N'-phenylsulfamide have been developed and come into use.
プラスチック製品の防菌防カビ剤の使用方法としては、
該製品の製造工程において防菌防カビ剤を練り込んで使
用するのが一般的であるが、前記２−（４’−チアゾリ
ル）−ベンツイミダゾール、Ｎ−（フルオロジクロロメ
チルチオ）−フタルイミド、Ｎ、Ｎ−ジメチル−Ｎ’−
（フルオロジクロルメチルチオ）−Ｎ゛−フェニルスル
ファミド等は粉末であり、使用時においては取り扱いに
くさあるいは微粉末による眼、皮膚等人体への刺激ある
いは作業項境の汚染などの問題があった。また樹脂ある
いは可塑剤への相溶性においても満足できる結果ではな
かった。How to use antibacterial and antifungal agents for plastic products:
It is common to use an antibacterial and antifungal agent in the manufacturing process of the product, but the above-mentioned 2-(4'-thiazolyl)-benzimidazole, N-(fluorodichloromethylthio)-phthalimide, N, N-dimethyl-N'-
(Fluorodichloromethylthio)-N-phenylsulfamide is a powder, and when used, there are problems such as difficulty in handling, irritation to the human body such as the eyes and skin due to the fine powder, and contamination of the work environment. Ta. Furthermore, the results were not satisfactory in terms of compatibility with resins or plasticizers.
プラスチック製品へ添加する防菌防カビ剤の必要条件と
しては、実用範囲で人畜無害であり、製造過程の１５０
−２４０℃での加熱工程で安定であること、雨水により
添加した薬剤が流出しないこと、薬剤添加した樹脂の物
理化学的特性を損わないこと、金属を腐食しないこと、
無臭であることなどである。The requirements for antibacterial and antifungal agents to be added to plastic products are that they are harmless to humans and animals within a practical range, and that
Stable in the heating process at -240℃, added chemicals will not be washed away by rainwater, will not impair the physicochemical properties of the resin to which the chemicals have been added, will not corrode metals,
For example, it is odorless.
本発明の防菌防カビ方法は全ての点でプラスチック製品
の防菌防カビ剤としての条件を満足しており、しかも少
量の添加で細菌類、カビ類、酵母類、藻類に有効に作用
する点で優れた殺菌作用を有する。The antibacterial and antifungal method of the present invention satisfies the requirements as an antibacterial and antifungal agent for plastic products in all respects, and is effective against bacteria, mold, yeast, and algae even when added in small amounts. It has an excellent bactericidal effect.
すなわち本発明は、下記（＋）〜（３）に示す化合物の
中から選ばれた１種又は２種以上をプラスチック製品の
製造工程において添加することにより、該プラスチック
製品の微生物による障害を防止することを特徴とするプ
ラスチ−２り製品の防菌防カビ方法およびその製品であ
る。That is, the present invention prevents damage caused by microorganisms to plastic products by adding one or more selected from the following compounds (+) to (3) in the manufacturing process of the plastic products. The present invention provides a method for preventing bacteria and mildew of Plasti-2 products, and a product thereof.
（１） １．４−ビス−ブロムアセトキシ−２−ブテン
Ｂ ｒｌｌｌ：Ｈ２ＣＯＯＣＨ２ＣＨ＝ＣＨＣＨｚ ０
ＣＯＣＨ２Ｂ ｒ（２） １．２−ビス−ブロムアセト
キシエタンＢ ｒＣＨ２ＣＯＯＣＨ２０Ｈ２０Ｃ０ＣＨ
２Ｂ ｒ（３） １．２−ビス−ブロムアセトキシプロ
パンＢ ｒｃＨｚ ＣＯＯＣＨ２ＣＯＯＣＨ２Ｂ ｒＣ
Ｈ。(1) 1.4-bis-bromoacetoxy-2-buteneB rllll:H2COOCH2CH=CHCHz 0
COCH2B r(2) 1.2-bis-bromoacetoxyethane B rCH2COOCH20H20C0CH
2B r(3) 1.2-Bis-bromoacetoxypropane B rcHz COOCH2COOCH2B rC
H.
本発明の化合物の特徴は、プラスチック製造で使用され
る可塑剤であるフタル酸ジオクチル、トリオクチルホス
フェート、リン酸トリクレジル。The compounds of the present invention are characterized by dioctyl phthalate, trioctyl phosphate, and tricresyl phosphate, which are plasticizers used in plastic manufacturing.
リン酸（トリスイソプロピルフェニル）などに２０％以
上の濃度で溶解するので、プラスチック製品の製造工程
での添加作業性が容易であり、また本発明の薬剤は液体
であるため従来の２−（４°−チアグリル）−ベンツイ
ミダゾール、Ｎ−（フルオロジクロロメチルチオ）−フ
タルイミド等の粉末の形態で練り込む際の、薬剤の飛散
による各種の人的被害の発生もない、さらに特徴として
は熱に安定であることである０例えばリン酸トリクレジ
ルに溶解し、 ２２０℃で２０分間保持しても、化合物
の分解はほとんど認められず、熱安定性の良好な薬剤で
ある。Since it dissolves in phosphoric acid (trisisopropylphenyl) at a concentration of 20% or more, it is easy to add it in the manufacturing process of plastic products, and since it is a liquid, it can be easily added to phosphoric acid (trisisopropylphenyl), etc. When kneading powdered substances such as °-thiagrily)-benzimidazole and N-(fluorodichloromethylthio)-phthalimide, there is no risk of human injury due to the scattering of the chemicals, and furthermore, they are stable to heat. For example, even when the compound is dissolved in tricresyl phosphate and kept at 220°C for 20 minutes, almost no decomposition of the compound is observed, making it a drug with good thermal stability.
また従来の２−（４°−チアゾリル）−ベンツイミダゾ
ール、 Ｎ−（フルオロジクロロメチルチオ）−フタル
イミド等に比較し、安価であるため経済的である。It is also economical because it is cheaper than conventional 2-(4°-thiazolyl)-benzimidazole, N-(fluorodichloromethylthio)-phthalimide, etc.
本発明の化合物（１）〜（３）は従来、製紙工程におけ
る白水や工業用冷却水のスライムコントロール剤として
、また水性エマルジョン、金属加工油、塗料、糊等の防
腐剤として使用されているが、樹脂に練り込んで樹脂製
品の防菌防カビ剤として使用されるということはなく、
またそのような用途に使用するという特許も存在しなか
った。The compounds (1) to (3) of the present invention have conventionally been used as slime control agents for white water in paper manufacturing processes and industrial cooling water, and as preservatives for aqueous emulsions, metal processing oils, paints, glues, etc. , it is not kneaded into resin and used as an antibacterial and antifungal agent for resin products.
There were also no patents for its use in such applications.
本発明の防菌防カビ方法はｆｉｌ化ビエビニル樹脂化ヒ
ニリデン樹脂、ポリエチレン樹脂、ポリプロピレン樹脂
、ポリスチレン樹脂、ブタジェン樹脂、ＡＢＳ樹脂、ポ
リウレタン樹脂など各種樹脂製品に適用できる。The antibacterial and antifungal method of the present invention can be applied to various resin products such as filtrated bivinyl resinized hnylidene resin, polyethylene resin, polypropylene resin, polystyrene resin, butadiene resin, ABS resin, and polyurethane resin.
使用方法は可塑剤に溶解して樹脂に添加するか、あるい
はこれら液体の薬剤をそのまま樹脂類に添加することも
可能である。使用濃度は樹脂量に対して０．Ｏ１〜２．
０％の量を添加することにより、プラスチック製品の微
生物汚損を長期間にわたり防止することができる。They can be used by dissolving them in plasticizers and adding them to resins, or by adding these liquid chemicals to resins as they are. The concentration used is 0.0% based on the amount of resin. O1-2.
By adding 0% of the amount, microbial contamination of plastic products can be prevented for a long period of time.
次に本発明の防菌防カビ剤の抗菌試験及び熱安定性試験
を以下の試験例に示すが、本発明はこれらに限定される
ものではない。Next, the antibacterial test and thermal stability test of the antibacterial and antifungal agent of the present invention are shown in the following test examples, but the present invention is not limited to these.
試験例１
標準画に対する抗菌試験
（１）供試菌
細菌類
Ａ、シ、−ドモナス−エルギノサ
（Ｐｓｅｕｄｏｍｏｎａｓ ａｅｒｇｉｎｏｓａ）Ｂ、
工・ンエリヒア舎コリ
（ＥＳｃｈｅｒｉｃｈｉａ ｃｏｌｉ）Ｃ，バチルス−
ズブチリス
（Ｂａｃｉｌｌｕｓ ５ｕｂｔｉｌｉｓ）Ｄ、スタフィ
ロコッカス・オウリウス
（Ｓｔａｐｈｙｌａｃｏｃｅｕｇ ａｕｒｅｕｓ）Ｅ、
アルカリゲネス会ビスコセス
（Ａｌｃａｌｉｇｅｎｅｓ ｖｉｓｃｏｓｅｓ）カビ類
Ｆ、 トリコデルマ舎ビリデ−
（Ｔｒｉｃｈｏｄｅｒｍａ ｖｉｒｉｄｅ）Ｇ、ペニ
シリウムーシトリヌム
（Ｐｅｎｉｃｉｌｌｉｕｍ ｃｉｔｒｉｎｕｍ）Ｈ，ア
スペルギルスｅニゲル
（＾ｓｐｅｒｇｉｌｌｕｓ ｎｉｇｅｒ）■、フザリウ
ム・モこリホルム
（Ｆｕｓａｒｉｕｍ ｍｏｎｉｌｉｆｏｒｍｅ）Ｊ、タ
ラトスボリウム争へルバフルム
（ＣＩａｄａｓｐａｒＩｕｒｉ ｈｅｒｂａｒｕａ）Ｋ
、ゲオトリカムφカンデタ′ム
（ＧｅｏｔｒｉｃｈｕＩＩｌｃａｎｄｉｄｕｍ）酵母類
り一 ロドトルラ・ルブラ
（Ｒｈｏｄｏｔｏｒｕｌａ ｒｕｂｒａ）藻類
Ｍ、クロレラ番ブルガリス
（Ｃｈｌｏｒｅｌ！ａ ｖｕｌｇａｒｉｓ）Ｎ、アナベ
ナφパリアビリス
（Ａｎａｂｅｎａ ｖａｒｉａｂｉｌｉｓ）０、セネデ
スムス・アクタス
（Ｓｃｅｎｅｄｅｓｍｕｓ ａｃｕｔｕｓ）（２）試験
方法
１．２−ビス−ブロムアセトキシ−２−ブテン、１．２
−ビス−ブロムアセトキシエタン及び１．２−ビス−ブ
ロムアセトキシプロパンをそれぞれ単独で所定濃度を含
むブイヨン寒天培地（細菌）、ジャガイモ寒天培地（カ
ビ、酵母）をベトリ皿に ｌｏｍ見ｒ！し、固化１７た
後、あらかじめ面培養した供試菌のｊ保温液を１白金耳
ずつ画線状に接種し、カビ類及び酵母類は２８℃の恒温
器で７日間、ＭＩＩ菌類は３７℃で３日間保持後、微生
物の発育状態を観察した。Test Example 1 Antibacterial test on standard drawings (1) Test bacteria Bacteria A, Pseudomonas aerginosa B,
E.Scherichia coli C, Bacillus
Bacillus 5ubtilis D, Staphylacocceug aureus E,
Alcaligenes viscoses mold F, Trichoderma viride G, Penicillium citrinum H, Aspergillus enigel (＾spergillus n) iger) ■, Fusarium moniliforme J, CIadaspar Iuri herbarua K
, GeotrichuIIlcandidum, yeast species Rhodotorula rubra, algae M, Chlorella vulgaris N, Anabena variabilis s) 0, Scenedesmus acutus ) (2) Test method 1.2-bis-bromoacetoxy-2-butene, 1.2
- Bromo agar medium (bacteria) and potato agar medium (mold, yeast) containing bis-bromoacetoxyethane and 1,2-bis-bromoacetoxypropane at predetermined concentrations in a vetri dish. After solidification, the insulating solution of the test bacteria that had been surface-cultured in advance was inoculated in a striped loop, and molds and yeasts were incubated in a thermostat at 28°C for 7 days, and MII fungi were incubated at 37°C. After holding for 3 days, the growth state of microorganisms was observed.
藻類は薬剤を所定濃度含むブトマー液体培地に藻類を植
え、明所で３週間数首後、藻類の繁殖用１１二濃度を求
めた。The algae were planted in a Butmer liquid medium containing the drug at a predetermined concentration, and after several weeks in the light, the 112 concentration for algae reproduction was determined.
（３）試験結果 最低発育防止濃度を表１に示す。(3) Test results The minimum growth-inhibiting concentrations are shown in Table 1.
表１＠低発育阻止濃度（ｐｐｍ）
ＢＢＡＢ：１．４−ビス−ブロムアセトキシ−２−ブテ
ン
ＢＢＡＥ：１．２−ビスーブロムアセトキシエタン
ＢＢＡＰ：１，２−ビス−ブロムアセトキシプロパン
細菌類、カビ類、酵母類、藻類に対し各化合物とも５０
ｐｐｍ以下で発育阻止が認められた。Table 1 @ Low inhibitory concentration (ppm) BBAB: 1,4-bis-bromoacetoxy-2-butene BBAE: 1,2-bis-bromoacetoxyethane BBAP: 1,2-bis-bromoacetoxypropane Bacteria, fungi 50 for each compound against yeast, algae, etc.
Growth inhibition was observed below ppm.
試験例２
塩化ビニル樹脂の微生物発生防止試験
塩化ビニル樹脂１００重量部、フタル酸ジオクチル６０
重量部及びトリクレン５重量部に、塩化ビニル樹脂に対
して０．０２−０．３％の各薬剤を加えて５０Ｘ ５０
ｍｍの塩化ビニル試験片を作成する。減菌ペトリ皿にジ
ャガイモ寒天培地を分注して平板培地を作る。寒天が・
固化した後に寒天の表面に前記の薬剤を添加した塩化ビ
ニル板を置き、これに試験例２に記ＪｌＬだ細菌類５種
の混合懸濁液ならびにカビ５種の胞子懸濁液を滅菌アト
マイザを用いて、塩化ビニル板を含めて培地表面に接種
する。Test Example 2 Microbial generation prevention test on vinyl chloride resin 100 parts by weight of vinyl chloride resin, 60 parts by weight of dioctyl phthalate
Add 0.02-0.3% of each chemical agent to vinyl chloride resin to 5 parts by weight of Trichloride and 50X 50 parts by weight.
Prepare a vinyl chloride test piece of mm. Prepare a plate medium by dispensing potato agar medium into a sterile Petri dish. Agar is...
After solidification, a vinyl chloride plate containing the above-mentioned chemicals was placed on the surface of the agar, and a mixed suspension of 5 types of bacteria and a spore suspension of 5 types of fungi described in Test Example 2 were placed on this plate using a sterilized atomizer. to inoculate the surface of the medium, including the vinyl chloride plate.
相対湿度８５％条件で、２８°Ｃにおいて２８日間培養
後、塩化ビニル板を取り出し、微生物の発生状態を肉眼
的に判定した。その結果を表２に示す。After culturing at 28° C. for 28 days at a relative humidity of 85%, the vinyl chloride plate was removed and the state of microbial growth was visually determined. The results are shown in Table 2.
表２
ＢＢＡＢ：１．４−ビス−ブロムアセトキシ−２−ブテ
ン
ＢＢＡＥ：１，２−ビス−ブロムアセトキシエタン
ＢＢＡＰ：１，２−ビス−ブロムアセトキシプロパン
本発明の化合物３種とも塩化ビニル樹脂に対して０．３
％添加群でも細菌類及びカビ類の発生を完全に防１１：
できた。Table 2 BBAB: 1,4-bis-bromoacetoxy-2-butene BBAE: 1,2-bis-bromoacetoxyethane BBAP: 1,2-bis-bromoacetoxypropane All three compounds of the present invention showed resistance to vinyl chloride resin. Te 0.3
Completely prevents the growth of bacteria and mold even in the % added group11:
did it.
試験例３
水に浸漬後の塩化ビニル樹脂の微生物発生防止試験
試験例２と同様にして塩化ビニル試験片を作成し、２週
間水に完全に浸漬した後、取り出した。Test Example 3 Test for preventing microbial generation of vinyl chloride resin after immersion in water A vinyl chloride test piece was prepared in the same manner as in Test Example 2, completely immersed in water for two weeks, and then taken out.
以下試験例２と全く同じ操作にて微生物発生防止試験を
行なった。A microbial generation prevention test was conducted in exactly the same manner as in Test Example 2 below.
結果は試験例２の結果と同一であり１本発明の薬剤が水
に流出しないことが明らかとなった。The results were the same as those of Test Example 2, and it was revealed that the drug of the present invention did not leak into water.
試験例４
ポリエチレンフィルムでの藻類発生阻止試験ポリエチレ
ン１００重量部に可塑剤４０重量部を加え、これに各薬
剤をポリエチレンに対してＱ、Ｑ３−０．５％の割合で
添加して、５０Ｘ ２５＋ａｍの薬剤入りフィルムを作
成する。減菌ペトリ皿にブトマー寒天培地を注入して平
板培地を作り、固化後にポリエチレンフィルムを培地の
表面に置く。Test Example 4 Algae Growth Inhibition Test on Polyethylene Film 40 parts by weight of plasticizer was added to 100 parts by weight of polyethylene, each agent was added to this at a ratio of Q, Q3-0.5% to polyethylene, and 50X 25+am Create a drug-containing film. Pour Butomer agar medium into a sterile Petri dish to make a plate medium, and after solidification, place a polyethylene film on the surface of the medium.
クロレラ０ブルガリス、アナベナ・パリアビリス及びセ
ネデスムス・アクタスをあらかじめ液体培地で培養した
藻類の懸濁液を寒天培地およびポリエチレンフィルム上
に均一に散布する。A suspension of algae in which Chlorella vulgaris, Anabaena parabilis, and Scenedesmus actus have been previously cultured in a liquid medium is uniformly spread on an agar medium and a polyethylene film.
これを２０℃、蛍光灯照射の下で７週間保持し、ポリエ
チレンフィルム上での藻類の繁殖の有無を肉眼にて判定
した。その結果を表３に示す。This was maintained at 20° C. under fluorescent lamp irradiation for 7 weeks, and the presence or absence of algae growth on the polyethylene film was visually determined. The results are shown in Table 3.
表３
ＢＢＡＢ：１，４−ビス−ブロムアセ
ブテン
ＢＢＡＥ：１．２−ビス−ブロムアセ
ン
Ｂ Ｂ Ａ Ｐ ： １，２−ビス−ブロムアセパン
ｌ−キシ−２−
トキシエタ
ト午シブロ
表４
試験例５
防菌病カビ剤としての熱安定性試験
本発明の化合物３種を可塑剤のフタル酸ジオクチル、リ
ン酸トリクレジル、トリオクチルホスフェートにそれぞ
れ２０％になるように溶解し、２２０℃で２０分間保持
後 各薬剤の残存率をガスクロマトグラフで分析した。Table 3 BBAB: 1,4-bis-bromoacebutene BBAE: 1,2-bis-bromoacepane B B A P: 1,2-bis-bromoacepane l-xy-2-toxyethate Table 4 Test Example 5 Antibacterial fungi Thermal stability test as a drug The three compounds of the present invention were dissolved in plasticizers dioctyl phthalate, tricresyl phosphate, and trioctyl phosphate to a concentration of 20% each, and after holding at 220°C for 20 minutes, the remaining amount of each drug was determined. The rate was analyzed by gas chromatography.
その結果は表４の通りである。The results are shown in Table 4.
ガスクロマトグラフ分析条件
３種の薬剤とも、プラスチック製品の製造工程で使用さ
れる可塑剤によく溶解し、熱安定性も良好であるのでプ
ラスチック製品の製造時に添加する防菌病カビ剤として
有効である。Gas chromatography analysis conditions All three types of chemicals dissolve well in plasticizers used in the manufacturing process of plastic products and have good thermal stability, so they are effective as antibacterial and fungal agents added during the manufacturing of plastic products. .
以上の試験例から認められるように、本発明の防菌病カ
ビ剤はプラスチック製品の製造工程において製品に添加
することにより、細菌類、カビ類、酵母類、藻類に対し
て抗菌活性を有するプラスチック製品の防菌病カビ剤で
あり、産業上の利用性は極めて大きい。As can be seen from the above test examples, the antibacterial and fungal agent of the present invention can be applied to plastic products that have antibacterial activity against bacteria, mold, yeast, and algae by adding it to products during the manufacturing process of plastic products. It is an antibacterial and fungal agent for products, and has extremely large industrial applicability.
特許出願人 市川合成化学株式会社 代 理 人 弁理士 若 林 忠Patent applicant: Ichikawa Synthetic Chemical Co., Ltd. Representative Patent Attorney Tadashi Wakabayashi
Claims (2)
テンＢｒＣＨ＿２ＣＯＯＣＨ＿２ＣＨ＝ＣＨＣＨ＿２Ｏ
ＣＯＣＨ＿２Ｂｒ（２）１，２−ビス−ブロムアセトキ
シエタンＢｒＣＨ＿２ＣＯＯＣＨ＿２ＣＨ＿２ＯＣＯＣ
Ｈ＿２Ｂｒ（３）１，２−ビス−ブロムアセトキシプロ
パン▲数式、化学式、表等があります▼ よりなるブロム酢酸誘導体の群から選ばれた１種又は２
種以上をプラスチック製品に含有させることを特徴とす
るプラスチック製品の防菌防カビ方法。(1) (1) 1,4-bis-bromoacetoxy-2-butene BrCH_2COOCH_2CH=CHCH_2O
COCH_2Br(2) 1,2-bis-bromoacetoxyethane BrCH_2COOCH_2CH_2OCOC
H_2Br(3) 1,2-bis-bromoacetoxypropane ▲ Numerical formulas, chemical formulas, tables, etc. are available ▼ One or two selected from the group of bromoacetic acid derivatives consisting of
A method for preventing germs and mildew of plastic products, characterized by containing seeds or more in the plastic product.
テンＢｒＣＨ＿２ＣＯＯＣＨ＿２ＣＨ＝ＣＨＣＨ＿２Ｏ
ＣＯＣＨ＿２Ｂｒ（２）１，２−ビス−ブロムアセトキ
シエタンＢｒＣＨ＿２ＣＯＯＣＨ＿２ＣＨ＿２ＯＣＯＣ
Ｈ＿２Ｂｒ（３）１，２−ビス−ブロムアセトキシプロ
パン▲数式、化学式、表等があります▼ よりなるブロム酢酸誘導体の群から選ばれた１種又は２
種以上をプラスチック製品に含有させたことを特徴とす
る防菌防カビ性プラスチック製品。(2) (1) 1,4-bis-bromoacetoxy-2-butene BrCH_2COOCH_2CH=CHCH_2O
COCH_2Br(2) 1,2-bis-bromoacetoxyethane BrCH_2COOCH_2CH_2OCOC
H_2Br(3) 1,2-bis-bromoacetoxypropane ▲ Numerical formulas, chemical formulas, tables, etc. are available ▼ One or two selected from the group of bromoacetic acid derivatives consisting of
An antibacterial and antifungal plastic product characterized by containing at least one species.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP15484088A JPH025956A (en) | 1988-06-24 | 1988-06-24 | Antifungal and antimoulding method for plastic product |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP15484088A JPH025956A (en) | 1988-06-24 | 1988-06-24 | Antifungal and antimoulding method for plastic product |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH025956A true JPH025956A (en) | 1990-01-10 |
Family
ID=15593036
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP15484088A Pending JPH025956A (en) | 1988-06-24 | 1988-06-24 | Antifungal and antimoulding method for plastic product |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH025956A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2003035756A1 (en) * | 2000-07-24 | 2003-05-01 | Mi Rae Tech Co., Ltd. | Resin composition of polyurethane-styrene-butadiene and method of manufacturing the same |
-
1988
- 1988-06-24 JP JP15484088A patent/JPH025956A/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2003035756A1 (en) * | 2000-07-24 | 2003-05-01 | Mi Rae Tech Co., Ltd. | Resin composition of polyurethane-styrene-butadiene and method of manufacturing the same |
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