JPH0559881B2 - - Google Patents
Info
- Publication number
- JPH0559881B2 JPH0559881B2 JP16700684A JP16700684A JPH0559881B2 JP H0559881 B2 JPH0559881 B2 JP H0559881B2 JP 16700684 A JP16700684 A JP 16700684A JP 16700684 A JP16700684 A JP 16700684A JP H0559881 B2 JPH0559881 B2 JP H0559881B2
- Authority
- JP
- Japan
- Prior art keywords
- parts
- ethylene glycol
- water
- metal
- dibromocyanoacetamide
- 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
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 45
- 239000000203 mixture Substances 0.000 claims description 35
- 229910052751 metal Inorganic materials 0.000 claims description 22
- 239000002184 metal Substances 0.000 claims description 22
- 150000001875 compounds Chemical class 0.000 claims description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 8
- 230000000844 anti-bacterial effect Effects 0.000 claims description 7
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- 241000894006 Bacteria Species 0.000 claims description 4
- 239000003619 algicide Substances 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 241000195493 Cryptophyta Species 0.000 claims 1
- 238000002156 mixing Methods 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 description 17
- UUIVKBHZENILKB-UHFFFAOYSA-N 2,2-dibromo-2-cyanoacetamide Chemical compound NC(=O)C(Br)(Br)C#N UUIVKBHZENILKB-UHFFFAOYSA-N 0.000 description 15
- 230000000052 comparative effect Effects 0.000 description 15
- 238000012360 testing method Methods 0.000 description 15
- 239000007788 liquid Substances 0.000 description 12
- 239000003814 drug Substances 0.000 description 9
- 229940079593 drug Drugs 0.000 description 9
- 238000004519 manufacturing process Methods 0.000 description 7
- 239000002173 cutting fluid Substances 0.000 description 6
- 150000002739 metals Chemical class 0.000 description 6
- 239000010935 stainless steel Substances 0.000 description 6
- 229910001220 stainless steel Inorganic materials 0.000 description 6
- NPBBKHBCJWFQRJ-UHFFFAOYSA-N 2,2-dibromo-2-cyano-n-methylacetamide Chemical compound CNC(=O)C(Br)(Br)C#N NPBBKHBCJWFQRJ-UHFFFAOYSA-N 0.000 description 5
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 5
- SIHKVAXULDBIIY-UPHRSURJSA-N [(z)-4-(2-bromoacetyl)oxybut-2-enyl] 2-bromoacetate Chemical compound BrCC(=O)OC\C=C/COC(=O)CBr SIHKVAXULDBIIY-UPHRSURJSA-N 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- DYTXHVPCRYAEEB-UHFFFAOYSA-N 2,2-dichloro-2-cyanoacetamide Chemical compound NC(=O)C(Cl)(Cl)C#N DYTXHVPCRYAEEB-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000000498 cooling water Substances 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 239000003973 paint Substances 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- -1 polyoxyethylene nonyl phenyl ether Polymers 0.000 description 3
- 238000012545 processing Methods 0.000 description 3
- 238000011160 research Methods 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- 230000002421 anti-septic effect Effects 0.000 description 2
- OOCMUZJPDXYRFD-UHFFFAOYSA-L calcium;2-dodecylbenzenesulfonate Chemical compound [Ca+2].CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O.CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O OOCMUZJPDXYRFD-UHFFFAOYSA-L 0.000 description 2
- DGJMPUGMZIKDRO-UHFFFAOYSA-N cyanoacetamide Chemical compound NC(=O)CC#N DGJMPUGMZIKDRO-UHFFFAOYSA-N 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 239000003755 preservative agent Substances 0.000 description 2
- 230000002335 preservative effect Effects 0.000 description 2
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 230000006641 stabilisation Effects 0.000 description 2
- 238000013112 stability test Methods 0.000 description 2
- 238000011105 stabilization Methods 0.000 description 2
- 230000000087 stabilizing effect Effects 0.000 description 2
- 230000000007 visual effect Effects 0.000 description 2
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- ABBGMXMPOCXVNL-UHFFFAOYSA-N 2-bromo-2-cyanoacetamide Chemical compound NC(=O)C(Br)C#N ABBGMXMPOCXVNL-UHFFFAOYSA-N 0.000 description 1
- QGAYKQRDYFAQFT-UHFFFAOYSA-N 2-chloro-2-cyanoacetamide Chemical compound NC(=O)C(Cl)C#N QGAYKQRDYFAQFT-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- LIMFPAAAIVQRRD-BCGVJQADSA-N N-[2-[(3S,4R)-3-fluoro-4-methoxypiperidin-1-yl]pyrimidin-4-yl]-8-[(2R,3S)-2-methyl-3-(methylsulfonylmethyl)azetidin-1-yl]-5-propan-2-ylisoquinolin-3-amine Chemical compound F[C@H]1CN(CC[C@H]1OC)C1=NC=CC(=N1)NC=1N=CC2=C(C=CC(=C2C=1)C(C)C)N1[C@@H]([C@H](C1)CS(=O)(=O)C)C LIMFPAAAIVQRRD-BCGVJQADSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 230000001098 anti-algal effect Effects 0.000 description 1
- 239000004599 antimicrobial Substances 0.000 description 1
- 239000005018 casein Substances 0.000 description 1
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 1
- 235000021240 caseins Nutrition 0.000 description 1
- 239000012459 cleaning agent Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 239000010730 cutting oil Substances 0.000 description 1
- 239000000645 desinfectant Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000007721 medicinal effect Effects 0.000 description 1
- 239000007769 metal material Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 230000001953 sensory effect Effects 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Landscapes
- Agricultural Chemicals And Associated Chemicals (AREA)
Description
（産業上の利用分野）
本発明はハロシアノアセトアミド化合物をエチ
レングリコールと水の溶液中に配合した金属存在
下の条件下でも安定していることを特徴とする防
菌防藻剤組成物及びその使用方法に関するもので
ある。
（従来の技術）
本発明の一般式
（ここに、Ｘはハロゲン原子、Ｙはハロゲン原子
又は水素原子、Ｒは水素原子又は低級アルキル基
を示す。）で示されるハロシアノアセトアミド化
合物は既に特公昭42−10386号公報明細書で抗微
生物剤として有効であることが知られている。上
記化合物は製紙パルプ工場、冷却水循環工程のス
ライムコントロール剤、殺藻剤、殺菌洗浄剤とし
て、また金属加工油剤、カゼイン、澱粉塗工液、
水性塗料の防腐剤等として適用性が広く、いずれ
の適用面においても優れた薬効が期待される。こ
のように適用範囲の広い薬剤である。
（発明が解決しようとする問題点）
しかしながら、これらを防菌防藻剤として用い
るには製造時、貯蔵保管時、使用時において安定
な薬剤であることが要求される。
即ち、ハロシアノアセトアミド化合物を配合し
てなる組成物は品質変化、特に有効成分の分解が
大きく、時に目的とする防菌、防藻剤としての効
能が発揮しない場合がある。このように適用性の
広い、しかも高い薬効を有した薬剤であるが、安
定性面においては種々の問題を持つた薬剤であ
り、長年安定化に関する研究が続けられてきた。
例えば、ポリエチレングリコール及びそれらのモ
ノ及びジメチル、エチル、ｎ−プロピル又はｎ−
ブチルエーテル類等の有機物液体にハロシアノア
セトアミド化合物を含有させ安定化させる方法が
明らかにされている（特公昭53−5375号）。
しかし、このように安定化についての研究が行
なわれてきたが、十分に満足出来る結果は得られ
ていないのが現状である。特に金属、例えば、
鉄、ステンレス、錫、亜鉛、銅又はこれらの合金
等の存在下で液体組成物中の本化合物の分解が著
しく大きい問題となつている。
例えば、ハロシアノアセトアミド化合物を含む
組成物を製造する場合金属との接触は避けられな
く、製造工程中にステンレス性の濾過機を使用し
た場合、製造時に有効成分は著しく分解し、目的
とした品質の液体組成物を得ることができない。
また、本組成物が実際に使用される場面である冷
却水循環工程や金属加工油剤、金属缶入水性塗料
など低濃度であつても金属との接触が生じる場合
には、ハロシアノアセトアミド化合物の分解によ
る効力持続力の低下やそれと共に工程等の金属面
への腐蝕がみられ改善が必要となつている。
以上のようにハロシアノアセトアミド化合物を
有効成分とする組成物は金属存在下でも有効成分
の分解がなく、組成物そのものの製剤安定化に加
え、また金属存在下での使用場面においても安心
して使用できる安定した薬剤を完成する必要があ
る。
（問題点を解決するための手段）
以上のような問題点を解決するため鋭意研究を
行つた結果、ハロシアノアセトアミド化合物をエ
チレングリコールと水を混合した液体中に溶解さ
せた液体組成物の安定性が著しく向上し、特に金
属の存在下であつても、有効成分が損なわれるこ
とがなく、製造時、貯蔵保管時、使用時における
安定性等の種々の問題を全て解決することができ
た。
本発明の安定なる液体組成物は前記一般式で示
されるハロシアノアセトアミド化合物５〜25重量
％をエチレングリコールと水の混合液体中に95〜
75重量％溶解してなる。ここで、エチレングリコ
ールと水との配合は１：１／７〜５である。
本願発明の組成物はハロシアノアセトアミド化
合物をエチレングリコールと水の混合液体中に溶
解して製造することができる。
本発明の前記一般式で示されるハロシアノアセ
トアミド化合物として、具体的にはモノクロロシ
アノアセトアミド、モノブロムシアノアセトアミ
ド、ジクロロシアノアセトアミド、ジブロモシア
ノアセトアミド、Ｎ−メチルジブロムシアノアセ
トアミド等が挙げられる。
本発明の安定化した組成物は無色透明から僅か
に淡黄色を呈する微粘稠の液体であり、使用に際
しては通常の定量ポンプにて工程等に容易に添加
できる。
次に、実施例、比較例を述べる。但し部は重量
部を示す。
（実施例）
実施例 １
ジクロルシアノアセトアミド20部、エチレング
リコール70部と水10部を混合溶解して、ジクロル
シアノアセトアミドを有効成分とする安定な組成
物を得る。
実施例 ２
ジグロモシアノアセトアミド20部、エチレング
リコール70部と水10部を混合溶解して、ジブロモ
シアノアセトアミドを有効成分とする安定な組成
物を得る。
比較例 １
モノブロムシアノアセトアミド20部とポリエチ
レングリコール（＃200）80部を混合溶解して、
モノブロムシアノアセトアミドを有効成分とする
組成物を得る。
比較例 ２
ジブロモシアノアセトアミド20部とジエチレン
グリコール80部を混合溶解して、ジブロモシアノ
アセトアミドを有効成分とする組成物を得る。
比較例 ３
ジブロモシアノアセトアミド20部とポリプロピ
レングリコール（＃400）80部を混合溶解してジ
ブロモシアノアセトアミドを有効成分とする組成
物を得る。
比較例 ４
ジブロモシアノアセトアミド20部とポリエチレ
ングリコール（＃200）80部を混合溶解して、ジ
ブロモシアノアセトアミドを有効成分とする組成
物を得る。
比較例 ５
Ｎ−メチルジブロモシアノアセトアミド20部と
ジメチルスルホキシド80部を混合溶解してＮ−メ
チルジブロモシアノアセトアミドを有効成分とす
る組成物を得る。
比較例 ６
Ｎ−メチルジブロモシアノアセトアミド20部と
トリメチレングリコール80部を混合溶解してＮ−
メチルジブロモシアノアセトアミドを有効成分と
する組成物を得る。
比較例 ７
ジブロモシアノアセトアミド20部、１，４−ビ
ス（ブロモアセトキシ）−２−ブテン15部、エチ
レングリコール43.5部、１，１，１−トリクロル
エタン20部、ポリオキシエチレンノニルフエニル
エーテル0.7部、ドデシルベンゼンスルホン酸カ
ルシウム0.3部、安定剤乳酸0.5部を混合溶解し
て、ジブロモシアノアセトアミド及び１，４−ビ
ス（ブロモアセトキシ）−２−ブテンを有効成分
とする組成物を得る。
比較例 ８
ジブロモシアノアセトアミド20部、１，４−ビ
ス（ブロモアセトキシ）−２−ブテン15部、エチ
レングリコール43.5部、１，１，１−トリクロル
エタン20部、ポリオキシエチレンノニルフエニル
エーテル0.7部、ドデシルベンゼンスルホン酸カ
ルシウム0.3部を混合溶解して、ジブロモシアノ
アセトアミド及び１，４−ビス（ブロモアセトキ
シ）−２−ブテンを有効成分とする組成物を得る。
比較例 ９
ジブロモシアノアセトアミド５部、エチレング
リコール15部と水80部を混合溶解して、ジブロモ
シアノアセトアミドを有効成分とする組成物を得
る。
（発明の効果）
製造工場において本発明による組成物を製造
し、その薬剤安定性について検討したが、比較薬
剤に比べ満足する結果が得られた。
また、金属切削油剤希釈液の防腐試験に於い
て、薬剤使用14日後の防腐効果、腐敗臭の官能試
験、テストピースの減量率及び肉眼観察より求め
た金属腐蝕性の結果から、本発明の薬剤が安定で
あることが確認された。
本発明の組成物はハロシアノアセトアミド化合
物の安定性が著しく向上し、特に金属の存在下で
ある金属性系列で使用した場合に於いても安定性
が著しく向上し、有効成分が損なわれることがな
く、製造時、貯蔵保管時、使用時における安定性
等の種々の問題を解決することがでる。
従つて、本発明の組成物は冷却水循環工程、金
属加工油剤あるいは金属製缶に封入した水性塗料
等金属との接触が生じる使用場面において、有効
成分の分解がなく使用できるものである。
次に本発明の効果について具体的に試験例によ
つて説明する。
試験例 １
ハロシアノアセトアミド化合物の安定性試験
実施例、比較例の各組成物を200ml容量の透明
ガラス瓶に150mlずつ量り取る。
ガラス瓶には日本テストパネル工業(株)製のステ
ンレステストピース（SOS304、1.0×2.0×120
mm）を２つ折りにして浸漬した。10日後に取り出
し、成分の分析及び外観の変化について観察を行
ない、液体組成物の安定性について判定した。な
お、比較例７については２個のガラス瓶を用意
し、ステレステストピース浸漬したものとしない
ものについて試験を行なゆた。未浸漬試験は比較
例７＊で示した。
結果を第１表に示す。
(Industrial Application Field) The present invention provides a bactericidal and algae-preventing composition comprising a halocyanoacetamide compound in a solution of ethylene glycol and water, which is stable even in the presence of a metal. It concerns how to use it. (Prior art) General formula of the present invention (Here, X is a halogen atom, Y is a halogen atom or a hydrogen atom, and R is a hydrogen atom or a lower alkyl group.) The halocyanoacetamide compound represented by the formula has already been described in Japanese Patent Publication No. 10386/1986 as an antimicrobial compound. It is known to be effective as a drug. The above compounds are used as slime control agents, algaecides, and disinfectant cleaning agents in paper and pulp mills, cooling water circulation processes, metal processing oils, casein, starch coating fluids,
It has wide applicability as a preservative for water-based paints, and is expected to have excellent medicinal effects in all applications. As such, it is a drug with a wide range of applications. (Problems to be Solved by the Invention) However, in order to use these as antibacterial and antialgal agents, it is required that the agents be stable during production, storage, and use. That is, compositions containing halocyanoacetamide compounds exhibit significant quality changes, particularly significant decomposition of the active ingredients, and may sometimes fail to exhibit their intended antibacterial and algae-proofing effects. Although it is a drug with wide applicability and high efficacy, it is a drug with various problems in terms of stability, and research on stabilization has been continued for many years.
For example, polyethylene glycols and their mono- and dimethyl, ethyl, n-propyl or n-
A method has been disclosed for stabilizing an organic liquid such as butyl ether by incorporating a halocyanoacetamide compound (Japanese Patent Publication No. 5375/1983). However, although research on stabilization has been conducted in this way, the current situation is that fully satisfactory results have not been obtained. Especially metals, e.g.
Decomposition of this compound in liquid compositions in the presence of iron, stainless steel, tin, zinc, copper, or alloys thereof has become a significant problem. For example, when manufacturing a composition containing a halocyanacetamide compound, contact with metal is unavoidable, and if a stainless steel filter is used during the manufacturing process, the active ingredient will be significantly decomposed during manufacturing, resulting in the desired quality. liquid composition cannot be obtained.
In addition, when contact with metal occurs even at low concentrations, such as in cooling water circulation processes, metal processing oils, and water-based paints in metal cans, where this composition is actually used, the decomposition of the halocyanacetamide compound may occur. As a result, there is a decrease in the durability of the potency and corrosion of metal surfaces during the process, etc., and improvements are needed. As mentioned above, compositions containing halocyanacetamide compounds as active ingredients do not decompose even in the presence of metals, and in addition to stabilizing the formulation itself, they can also be used with confidence in the presence of metals. It is necessary to develop a stable drug that can be used. (Means for solving the problem) As a result of intensive research to solve the above problems, we have found that a liquid composition in which a halocyanacetamide compound is dissolved in a liquid mixture of ethylene glycol and water has been stabilized. The properties of the product were significantly improved, and the active ingredients remained intact even in the presence of metals, and various problems such as stability during production, storage, and use were solved. . The stable liquid composition of the present invention contains 5 to 25% by weight of a halocyanoacetamide compound represented by the above general formula in a mixed liquid of ethylene glycol and water.
75% by weight dissolved. Here, the ratio of ethylene glycol and water is 1:1/7 to 5. The composition of the present invention can be produced by dissolving a halocyanoacetamide compound in a liquid mixture of ethylene glycol and water. Specific examples of the halocyanoacetamide compound represented by the above general formula of the present invention include monochlorocyanoacetamide, monobromocyanoacetamide, dichlorocyanoacetamide, dibromocyanoacetamide, N-methyldibromocyanoacetamide, and the like. The stabilized composition of the present invention is a slightly viscous liquid that is colorless and transparent to slightly pale yellow in color, and can be easily added to a process using an ordinary metering pump. Next, examples and comparative examples will be described. However, parts indicate parts by weight. (Examples) Example 1 20 parts of dichlorocyanoacetamide, 70 parts of ethylene glycol, and 10 parts of water are mixed and dissolved to obtain a stable composition containing dichlorocyanoacetamide as an active ingredient. Example 2 20 parts of dibromocyanoacetamide, 70 parts of ethylene glycol, and 10 parts of water are mixed and dissolved to obtain a stable composition containing dibromocyanoacetamide as an active ingredient. Comparative Example 1 20 parts of monobromic cyanoacetamide and 80 parts of polyethylene glycol (#200) were mixed and dissolved.
A composition containing monobromic cyanoacetamide as an active ingredient is obtained. Comparative Example 2 20 parts of dibromocyanoacetamide and 80 parts of diethylene glycol are mixed and dissolved to obtain a composition containing dibromocyanoacetamide as an active ingredient. Comparative Example 3 20 parts of dibromocyanoacetamide and 80 parts of polypropylene glycol (#400) are mixed and dissolved to obtain a composition containing dibromocyanoacetamide as an active ingredient. Comparative Example 4 20 parts of dibromocyanoacetamide and 80 parts of polyethylene glycol (#200) are mixed and dissolved to obtain a composition containing dibromocyanoacetamide as an active ingredient. Comparative Example 5 20 parts of N-methyldibromocyanoacetamide and 80 parts of dimethyl sulfoxide are mixed and dissolved to obtain a composition containing N-methyldibromocyanoacetamide as an active ingredient. Comparative Example 6 20 parts of N-methyldibromocyanoacetamide and 80 parts of trimethylene glycol were mixed and dissolved to obtain N-
A composition containing methyldibromocyanoacetamide as an active ingredient is obtained. Comparative Example 7 20 parts of dibromocyanoacetamide, 15 parts of 1,4-bis(bromoacetoxy)-2-butene, 43.5 parts of ethylene glycol, 20 parts of 1,1,1-trichloroethane, 0.7 part of polyoxyethylene nonyl phenyl ether , 0.3 part of calcium dodecylbenzenesulfonate, and 0.5 part of lactic acid stabilizer are mixed and dissolved to obtain a composition containing dibromocyanoacetamide and 1,4-bis(bromoacetoxy)-2-butene as active ingredients. Comparative Example 8 20 parts of dibromocyanoacetamide, 15 parts of 1,4-bis(bromoacetoxy)-2-butene, 43.5 parts of ethylene glycol, 20 parts of 1,1,1-trichloroethane, 0.7 parts of polyoxyethylene nonyl phenyl ether , and 0.3 part of calcium dodecylbenzenesulfonate are mixed and dissolved to obtain a composition containing dibromocyanoacetamide and 1,4-bis(bromoacetoxy)-2-butene as active ingredients. Comparative Example 9 5 parts of dibromocyanoacetamide, 15 parts of ethylene glycol, and 80 parts of water are mixed and dissolved to obtain a composition containing dibromocyanoacetamide as an active ingredient. (Effects of the Invention) A composition according to the present invention was manufactured at a manufacturing factory and its drug stability was examined, and results were obtained that were satisfactory compared to comparative drugs. In addition, in a preservative test of a diluted metal cutting fluid, the antiseptic effect after 14 days of use, a sensory test of putrid odor, the weight loss rate of the test piece, and the metal corrosivity determined by visual observation revealed that the drug of the present invention was confirmed to be stable. The composition of the present invention significantly improves the stability of the halocyanoacetamide compound, and particularly when used in the presence of metals in the metallic series, the stability is significantly improved and the active ingredient is not impaired. This makes it possible to solve various problems such as stability during manufacturing, storage, and use. Therefore, the composition of the present invention can be used without decomposition of its active ingredients in situations where it comes into contact with metal, such as in cooling water circulation processes, metal processing oils, or water-based paints sealed in metal cans. Next, the effects of the present invention will be specifically explained using test examples. Test Example 1 Stability test of halocyanacetamide compound 150 ml of each of the compositions of Examples and Comparative Examples was weighed into a 200 ml transparent glass bottle. A stainless steel test piece (SOS304, 1.0 x 2.0 x 120 manufactured by Nippon Test Panel Industry Co., Ltd.) was placed in the glass bottle.
mm) was folded in half and immersed. After 10 days, the liquid composition was taken out, and the stability of the liquid composition was determined by analyzing the components and observing changes in appearance. For Comparative Example 7, two glass bottles were prepared, and the test was conducted with and without the stainless steel test piece immersed. The non-immersion test was shown in Comparative Example 7*. The results are shown in Table 1.
【表】
試験例 ２
工場にて製造したハロシアノアセトアミド化合
物の安定性試験
実施例２、比較例４の薬剤を実際の工場内のエ
タナールライニングした配合釜にてそれぞれ1000
Kgを製造した。製品はステンレス製のウルトラホ
ーマー濾過装置を用い、30分を要して濾過しステ
ンレス製の製品タンクに約１時間保管した。製品
タンクに貯槽された製品は、１時間後ポリエチレ
ン製容器に充填した。次いで、充填された製品１
缶を40℃の恒温室内に保管し、30日、60日後に、
成分分析と外観の変化の観察を行ない安定性を追
跡した。
結果を第２表に示す。[Table] Test Example 2 Stability test of halocyanoacetamide compound manufactured in a factory The drugs of Example 2 and Comparative Example 4 were each tested at 1,000 ml in an ethanal-lined compounding pot in an actual factory.
Kg was produced. The product was filtered for 30 minutes using a stainless steel Ultraformer filtration device and stored in a stainless steel product tank for about 1 hour. The product stored in the product tank was filled into a polyethylene container after 1 hour. Then the filled product 1
Store the can in a constant temperature room at 40℃, and after 30 and 60 days,
Stability was tracked through component analysis and observation of changes in appearance. The results are shown in Table 2.
【表】
試験例 ３
金属切削油剤希釈液の防腐試験
精密機械部品を製造する工場のトランスフアー
マシンより微生物汚染の進行した切削油剤希釈液
を入手する。入手した切削油剤希釈液の内容は次
の通りである。
タイプ：エマルジヨンタイプ
希釈倍数：35倍
希釈液のPH：8.1
生産菌：細菌：4.1×107／ml
糸状菌・酵母：2.0×104／ml
予め、室内に設置した小型の切削油剤希釈液循
環工程に、微生物汚染の進行した切削油剤希釈液
と供試剤を加え運転を開始する。一定時間後にお
ける生菌数の測定、切削油剤希釈液の腐敗臭及び
金属の腐蝕性観察試験より、薬剤のもつ殺菌力、
防腐効力、金属材質への影響を確認した。
結果を第３表に示す。[Table] Test Example 3 Preservation test of diluted metal cutting fluid A diluted cutting fluid with advanced microbial contamination was obtained from a transfer machine in a factory that manufactures precision machine parts. The contents of the diluted cutting fluid obtained are as follows. Type: Emulsion type Dilution ratio: 35 times PH of diluted liquid: 8.1 Producing bacteria: Bacteria: 4.1×10 7 /ml Filamentous fungi/yeast: 2.0×10 4 /ml Small cutting oil diluted solution installed indoors in advance Add the microbial-contaminated diluted cutting fluid and the test material to the circulation process and start operation. The bactericidal power of the agent was determined by measuring the number of viable bacteria after a certain period of time, observing the putrid odor of the diluted cutting fluid, and observing the corrosivity of metals.
The antiseptic effect and effect on metal materials were confirmed. The results are shown in Table 3.
【表】
腐敗臭判定基準 −：油剤のみの臭気
：腐敗臭強
テストピースの表面に於けるサビ発生量判定基準(肉
眼観察)
−：サビの発生なし
＋：僅かなサビの発生がある
：1〓3の面積にサビの発生がある
：2〓3の 〃
＋＋＋＋：2〓3以上の面積にサビの発生がある
[Table] Putrid odor judgment criteria −: Odor from oil only
: Strong rotten odor Criteria for determining the amount of rust on the surface of the test piece (visual observation)
-: No rust formation +: Slight rust formation: Rust formation on area of 1〓3: 〃 of 2〓3
＋＋＋＋: Rust occurs in an area of 2〓3 or more
Claims (1)
又は水素原子、Ｒは水素原子又は低級アルキル基
を示す。）で表されるハロシアノアセトアミド化
合物５〜25重量％をエチレングリコールと水95〜
75重量％の溶液中に配合し、エチレングリコール
と水の割合が１：１／７〜５であることを特徴と
する金属の存在下で安定化した防菌防藻剤組成
物。 ２ ハロシアノアセトアミド化合物、エチレング
リコール及び水よりなる配合物を金属製缶に封入
した特許請求の範囲第１項記載の防菌防藻剤組成
物。 ３ ハロシアノアセトアミド化合物、エチレング
リコール及び水よりなる配合物を金属製系列で使
用する特許請求の範囲第１項記載の防菌防藻剤組
成物。 ４ 一般式 （ここに、Ｘはハロゲン原子、Ｙはハロゲン原子
又は水素原子、Ｒは水素原子又は低級アルキル基
を示す。）で表されるハロシアノアセトアミド化
合物５〜25重量％をエチレングリコールと水の割
合が１：１／７〜５である溶液95〜75重量％に配
合し金属の存在下で安定化した組成物を用いる防
菌防藻方法。[Claims] 1. General formula (Here, X is a halogen atom, Y is a halogen atom or a hydrogen atom, and R is a hydrogen atom or a lower alkyl group.) 5 to 25% by weight of a halocyanoacetamide compound represented by ethylene glycol and 95 to 95% of water are mixed with ethylene glycol and water.
A bactericidal and algaecide composition stabilized in the presence of a metal, which is formulated in a 75% by weight solution and is characterized in that the ratio of ethylene glycol to water is 1:1/7 to 5. 2. The antibacterial and algae-preventing agent composition according to claim 1, wherein a compound consisting of a halocyanoacetamide compound, ethylene glycol, and water is enclosed in a metal can. 3. The antibacterial and algaecide composition according to claim 1, which uses a combination of a halocyanoacetamide compound, ethylene glycol, and water in a metallic series. 4 General formula (Here, X is a halogen atom, Y is a halogen atom or a hydrogen atom, and R is a hydrogen atom or a lower alkyl group). A method for preventing bacteria and algae using a composition stabilized in the presence of a metal by blending the solution with a ratio of 1:1/7 to 5 at 95 to 75% by weight.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP16700684A JPS6144804A (en) | 1984-08-09 | 1984-08-09 | Stabilized antimicrobial and algicidal composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP16700684A JPS6144804A (en) | 1984-08-09 | 1984-08-09 | Stabilized antimicrobial and algicidal composition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6144804A JPS6144804A (en) | 1986-03-04 |
| JPH0559881B2 true JPH0559881B2 (en) | 1993-09-01 |
Family
ID=15841629
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP16700684A Granted JPS6144804A (en) | 1984-08-09 | 1984-08-09 | Stabilized antimicrobial and algicidal composition |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6144804A (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2000026216A (en) * | 1999-06-02 | 2000-01-25 | Somar Corp | Industrial microbicide |
| JP2008091477A (en) * | 2006-09-29 | 2008-04-17 | Brother Ind Ltd | Device for adjusting quantity of light and device for forming image |
| JP5900976B2 (en) * | 2012-09-18 | 2016-04-06 | フジ産業株式会社 | Industrial disinfectant composition with improved safety |
-
1984
- 1984-08-09 JP JP16700684A patent/JPS6144804A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6144804A (en) | 1986-03-04 |
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