KR100313665B1 - Stabilized isothiazolone composition - Google Patents

Stabilized isothiazolone composition Download PDF

Info

Publication number
KR100313665B1
KR100313665B1 KR1019940032167A KR19940032167A KR100313665B1 KR 100313665 B1 KR100313665 B1 KR 100313665B1 KR 1019940032167 A KR1019940032167 A KR 1019940032167A KR 19940032167 A KR19940032167 A KR 19940032167A KR 100313665 B1 KR100313665 B1 KR 100313665B1
Authority
KR
South Korea
Prior art keywords
isothiazolone
weight
substituted
diethyl
toluamide
Prior art date
Application number
KR1019940032167A
Other languages
Korean (ko)
Other versions
KR960016718A (en
Inventor
동은수
김진배
김진만
김승환
Original Assignee
에스케이케미칼주식회사
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by 에스케이케미칼주식회사 filed Critical 에스케이케미칼주식회사
Priority to KR1019940032167A priority Critical patent/KR100313665B1/en
Publication of KR960016718A publication Critical patent/KR960016718A/en
Application granted granted Critical
Publication of KR100313665B1 publication Critical patent/KR100313665B1/en

Links

Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/22—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing ingredients stabilising the active ingredients

Abstract

PURPOSE: A stabilized isothiazolone composition comprising a isothiazolone compound, N,N'-diethyl-toluamide and an organic solvent is provided. The stabilized isothiazolone composition is very stable in an atmosphere, maintains pharmacological efficacy even though long-term storage and is applied to any area where is contaminated by bacteria, fungi, yeast or algae. CONSTITUTION: An isothiazolone composition comprises a 3-isothiazolone compound represented by the formula(I), N,N'-diethyl-toluamide and organic solvent. In formula, R1 and R2 are the same or different, and represent H, halogen or a C1-4 alkyl group; R3 is H, halogen, or a hydroxy substituted or non-substituted C1-10 alkyl group, a halogen substituted or non-substituted C2-10 alkenyl group, a halogen substituted or non-substituted C2-10 alkinyl group and a halogen, C1-10 alkyl or C2-9 alkoxy substituted or non-substituted aralkyl group. The weight ratio of N,N'-diethyl-toluamide to 3-isothiazolone is 1:50 to 20:1. The organic solvent is alcohol, polyol and glycol ethers.

Description

안정화된 이소티아졸른 조성물Stabilized Isothiazoline Composition

본발명은 안정화된 이소티아졸론 조성물에 관한 것으로, 더욱 상세하게는 다음 구조식(I)로 표시되는 이소티아졸론 화합물,N,N'-디에틸-m-톨루아마이드 및 유기용매로 이루어진 안정화된 3-이소티아졸론 조성물에 관한 것이다.The present invention relates to a stabilized isothiazolone composition, and more particularly, to a stabilized 3 consisting of an isothiazolone compound represented by the following structural formula (I), N, N' -diethyl- m -toluamide and an organic solvent. It relates to an isothiazolone composition.

상기식에서,In the above formula,

R1및 R2는 각각 서로 같거나 다른 것으로서, 수소원자; 할로겐원자 ; 또는 C1~ C4의 알킬기 이고,R 1 and R 2 are the same as or different from each other, and are a hydrogen atom; Halogen atom; Or a C 1 to C 4 alkyl group,

R3는 수소원자 ; 할로겐원자 : 또는 히드록시기로 치환되거나 치환되지 않은 C2~ C10의 알킬기; 할로겐원자로 치환되거나 치환되지 않은 C2~ C10의 알케닐기; 할로겐원자로 치환되거나 치환되지 않은 C2~ C10의 알키닐기; 할로겐원자, C1~ C10의알킬기 또는 C2~ C9의 알콕시기로 치환되거나 치환되지 않은 아랄킬기이다.R 3 is a hydrogen atom; Halogen atom: or a C 2 to C 10 alkyl group unsubstituted or substituted with a hydroxy group; C 2 ~ C 10 alkenyl group unsubstituted or substituted with a halogen atom; C 2 ~ C 10 alkynyl group unsubstituted or substituted with a halogen atom; Or an aralkyl group which is unsubstituted or substituted with a halogen atom, a C 1 to C 10 alkyl group or a C 2 to C 9 alkoxy group.

이소티아졸론 화합물은 1965년 크라우 등에 의해 개발된 이후, 살균제를 비롯해 도료, 화장품, 섬유 또는 플라스틱 등의 항균 및 항미생물제로써 산업전반에 걸쳐 확대되어 사용되고 있다. 그러나, 이소티아졸론 화합물은 매우 불안정하여 대기중의 습기와 자외선에 의해 쉽게 분해되므로 이소티아졸론 화합물을 첨가시킨 제품의 보관시 그 효과가 감소될 수 있다. 따라서, 이소터아졸론 화합물의 안정성을 향상시키기 위한 다양한 방법들이 연구 개발되어 왔으며, 전형적인 방법은 금속염 안정화제를 사용하는 것이다.Since the isothiazolone compound was developed by Crow et al. In 1965, it has been widely used throughout the industry as an antimicrobial and antimicrobial agent such as disinfectants, paints, cosmetics, textiles or plastics. However, since the isothiazolone compound is very unstable and easily decomposed by moisture and ultraviolet light in the air, its effect may be reduced upon storage of the product to which the isothiazolone compound is added. Therefore, various methods for improving the stability of the isoterazolone compound have been researched and developed, and a typical method is to use a metal salt stabilizer.

그 예로서 미국특허 제3,870,795호 및 제4,067,878호에서는 금속아질산염 또는 금속질산염의 첨가에 의한 화학적 분해에 의해 이소티아졸론 화합물의 안정화를 시도한 바 있으나, 이와같은 금속염 및 안정화제들은 폴리머가 분산되어 있는 라텍스 에멀젼 수용액에서 에멀젼 성분과 반응하여 응집 현상이나 침전물을 발생시킬 수 있으며, 또한 어떤 시스템에서는 금속염에 결합된 염소이온에 의해 시스템의 부식을 유발시키기도 하므로 이와같은 시스템에서의 금속염 제거는 필수적이다.For example, US Pat. Nos. 3,870,795 and 4,067,878 have attempted stabilization of isothiazolone compounds by chemical decomposition by the addition of metal nitrites or metal nitrates. Removal of metal salts in these systems is essential because they can react with the emulsion components in aqueous emulsions, causing flocculation or sedimentation, and in some systems causing corrosion of the system by chlorine ions bound to the metal salts.

이에 본 발명의 발명자들은 상기 종래의 이소티아졸론의 안정화 방법에 따른 제반 문제점을 해결하고자 노력한 결과, 이소티아졸론 화합물을 함유한 조성물에N,N'-디에틸-m-톨루아마이드를 첨가하면 이소티아졸론의 분해를 막을 수 있으리라는 점에 착안하여 본 발명을 완성하였다.Therefore, the inventors of the present invention have tried to solve the problems associated with the stabilization method of the conventional isothiazolone, and as a result, when N, N' -diethyl- m -toluamide is added to the composition containing the isothiazolone compound, The present invention has been completed by focusing on preventing the decomposition of thiazolone.

본 발명은 항미생물제로서의 안정화된 3-이소티아졸론 조성물을 제공하는데그 목적이 있다.The present invention aims to provide a stabilized 3-isothiazolone composition as an antimicrobial agent.

이하, 본 발명을 상세히 설명하면 다음과 같다.Hereinafter, the present invention will be described in detail.

본발명은 다음 구조식(I)로 표시되는 3-이소티아졸론 화합물,N,N'-디에틸-m-톨루아마이드 및 용매로 이루어진 이소티아졸론 조성물을 그 특징으로 한다.The present invention is characterized by an isothiazolone composition composed of a 3-isothiazolone compound represented by the following structural formula (I), N, N' -diethyl- m -toluamide and a solvent.

상기 식에서 R1,R2및 R3는 상기에서 정의한 바와 같다.Wherein R 1 , R 2 and R 3 are as defined above.

이와같은 본 발명을 더욱 상세히 설명하면 다음과같다.The present invention will be described in more detail as follows.

본 발명은 대기중에 불안정한 3-이소티아졸론 화합물을 안정화시키기 위해 안정화제로서N,N'-디에틸-m-톨루아마이드를 혼합시킨 이소티아졸론 조성물에 관한 것이다.The present invention relates to an isothiazolone composition in which N, N' -diethyl- m -toluamide is mixed as a stabilizer to stabilize an unstable 3-isothiazolone compound in the atmosphere.

본 발명에서 사용될 수 있는 3-이소티아졸론 화합물은 상기 구조식(I)로 표시되는 화합물 중에서 선택된 단독 또는 2종 이상의 혼합물이며, 바람직하기로는 5-클로로-2-메틸-3-이소티아졸론, 2-메틸-3-이소티아즐론, 2-n-옥틸-3-이소티아졸론, 4,5-디클로로-2-시클로헥실-3-이소티아졸론 및 4,5-디클로로-2-n-옥틸-3-이소티아졸론중에서 선택된 단독 또는 2종이상의 혼합물이다· 이중 가장 바람직하기로는 5-클로로-2-메틸-3-이소티아졸론 또는 5-클로로-2-메틸-3-이소티아졸론과 2-메틸-3-이소티아졸론의 혼합물이다. 5-클로로-2-메틸-3-이소티아졸론과 2-메틸-3-이소티아졸론 혼합물의 경우, 바람직한 혼합비는 약 70 : 30 ~ 85 : 15 중량%이고, 더욱 바람직한 혼합비는 약 70 : 30 ~ 80 : 20 중량%이다. 한편, 2-메틸-3-이소티아졸론이 주성분이고 5-클로로-2-메틸-3-이소티아졸론이 소량 혼합된 혼합물도 매우 바람직한데, 이러한 경우 바람직한 혼합비는 약 98:2 ~ 96:4 중량%이고, 특히 바람직한 혼합비는 약 97 : 3 중량%이다.The 3-isothiazolone compound which can be used in the present invention is a single or a mixture of two or more selected from the compounds represented by the above formula (I), preferably 5-chloro-2-methyl-3-isothiazolone, 2 -Methyl-3-isothiazone, 2-n-octyl-3-isothiazolone, 4,5-dichloro-2-cyclohexyl-3-isothiazolone and 4,5-dichloro-2-n-octyl- Single or a mixture of two or more selected from 3-isothiazolones, most preferably 5-chloro-2-methyl-3-isothiazolone or 5-chloro-2-methyl-3-isothiazolone and 2- Mixture of methyl-3-isothiazolone. In the case of the 5-chloro-2-methyl-3-isothiazolone and 2-methyl-3-isothiazolone mixtures, the preferred mixing ratio is about 70:30 to 85:15 wt%, and more preferred mixing ratio is about 70:30 80: 20 weight%. On the other hand, a mixture of 2-methyl-3-isothiazolone as a main component and a small amount of 5-chloro-2-methyl-3-isothiazolone is also highly desirable. In this case, a preferred mixing ratio is about 98: 2 to 96: 4. % By weight, and a particularly preferred mixing ratio is about 97: 3% by weight.

본 발명의 이소티아졸론 조성물 제조시 안정화제로서 사용되는N,N'-디에틸-m-톨루아마이드의 양은 사용조건 및 혼합물내의 이소티아졸론 농도에 따라 변화될 수 있는 바, 효과적인 양은N,N'-디에틸-m-톨루아마이드 : 이소티아졸론의 혼합비가 1:100~1000:1 중량비인 경우이고, 농축용액에서는 1 : 50 ~ 50 : 1 중량비가 일반적이며, 그 이상의N,N'-디에틸-m-톨루아마이드가 사용될 수도 있으나 이는 비경제적이다. 상당히 희석되어진 3-이소티아졸론용액(용매내 약 1 ~ 10000ppm 이소티아졸론과 같은 경우)에서는N,N'-디에틸-m-톨루아마이드 : 이소티아즐론의 비가 약 1 : 10 - 20 : 1 중량비이고, 바람직하게는 1 : 5 ~ 20 : 1 중량비이다.Isothiazolone composition N, N 'is used as a stabilizer in the production of the invention-diethyl-m-bars, which may be changed according to the isothiazolone concentration in the amount of use conditions, and mixtures of Tolu amide, an effective amount of N, N ' -Diethyl- m -toluamide: isothiazolone mixing ratio is 1: 100 ~ 1000: 1 weight ratio, and in concentrated solution, 1: 50 ~ 50: 1 weight ratio is common, more than N, N'- Diethyl- m -toluamide may be used but this is uneconomical. In a highly diluted 3-isothiazolone solution (such as about 1 to 10000 ppm isothiazolone in a solvent), the ratio N, N' -diethyl- m -toluamide to isothiazolone is about 1: 10-20: 1 It is weight ratio, Preferably it is 1: 5-20: 1 weight ratio.

본 발명에 따른 3-이소티아졸론 조성물은 용액의 형태로 제조되는 바, 그 조성비는 상기 구조식(I)로 표시되는 3-이소티아졸론 화합물 중에서 선택된 단독 또는 2종 이상의 혼합물 약 0,01 ~ 99 중량%,N,N'-디에틸-m-톨루아마이드 0.01 ~ 99 중량% 및 용매 99.98 중량% 이하이고 ; 바람직하기로는 상기 구조식(I)로 표시되는 3-이소티아졸론 화합물 중에서 선택된 단독 또는 2종 이상의 혼합물 0.01~ 15 중량%,N,N'-디에틸-m-톨루아마이드 0.01 ~ 15 중량% 및 용매 90 ~ 99.98중량% 이고 ; 가장 바람직하기로는 상기 구조식(I)로 표시되는 3-이소티아졸론 화합물 중에서 선택된 단독 또는 2종 이상의 혼합물 0.01 ~ 1 중량%,N,N'-디에틸-m-톨루아마이드 0.01 ~ 1 중량% 및 용매 98 ~ 99.98 중량%이다.3-isothiazolone composition according to the present invention is prepared in the form of a solution, the composition ratio is about 0,01 to 99 alone or a mixture of two or more selected from the 3-isothiazolone compound represented by the formula (I) Weight%, N, N' -diethyl- m -toluamide 0.01-99 weight% and a solvent 99.98 weight% or less; Preferably, 0.01 to 15% by weight of a single or two or more mixtures selected from 3-isothiazolone compounds represented by the above formula (I), 0.01 to 15% by weight of N, N' -diethyl- m -toluamide and a solvent 90 to 99.98% by weight; Most preferably, 0.01 to 1% by weight of a single or two or more mixtures selected from 3-isothiazolone compounds represented by the above formula (I), 0.01 to 1% by weight of N, N' -diethyl -m -toluamide and Solvent 98-99.98% by weight.

상기와 같은 본 발명의 조성물은 용액의 형태로 제조되며, 그 용도에 따라 농축용액 또는 희석용액으로 제조되고, 대량 선적과 같은 특정 사용의 경우에는 더욱 농축된 용액이 사용될 수 있다.The composition of the present invention as described above is prepared in the form of a solution, depending on the use of the solution is prepared in concentrated or dilute solution, in the case of specific use, such as bulk shipping, a more concentrated solution can be used.

본 발명에서 사용될 수 있는 용매는 이소티아졸론 화합물을 용해시키고, 또한 이를 안정화시킬 수 있는 유기용매라면 어느 것이든 사용 가능하다. 예를들면 글리콜 또는 알콜과 같은 수산기 용매도 사용될 수 있으며,N,N'-디에틸-m-톨루아마이드에 대한 이소티아졸론의 사용량의 비가 클수록, 그리고 높은 희석조건에서는 글리콜을 사용하면 더욱 효과적이다. 또한, 일련의 조성물에서는 지방족 또는 방향족 탄화수소류가 유용하다. 이외에도 바람직한 용매로는 자유 수산기(free hydroxy)가 에테르 또는 에스테르 작용기로 치환된 폴리올류이며, 이중 특히 바람직하기로는 에틸렌 글리콜 메틸 에테르 또는 에틸렌 글리콜 디메틸 에테르이다.The solvent that can be used in the present invention can be used as long as it is an organic solvent that can dissolve and stabilize the isothiazolone compound. Hydroxyl solvents such as, for example, glycols or alcohols may also be used, and the greater the ratio of isothiazolone to N, N' -diethyl- m -toluamide, and the more effective the use of glycol at high dilution conditions . In addition, aliphatic or aromatic hydrocarbons are useful in a series of compositions. In addition, preferred solvents are polyols in which free hydroxy is substituted with an ether or ester functional group, particularly preferably ethylene glycol methyl ether or ethylene glycol dimethyl ether.

본 발명에 따른 이소티아졸론 조성물은 이소티아졸론류의 안정화를 이루는데 단지 소량의N,N'-디에틸-m-톨루아마이드가 사용될 수 있으며, 이로써 처리될 시스템 내에서의N,N'-디에틸-m-톨루아마이드의 양은 매우 소량이며, 보호가 요구되는 시스템 내의 다른 성분들 또는 보호시스템이 적용되는 시스템을 방해하지 않는다.In the isothiazolone composition according to the present invention, only a small amount of N, N' -diethyl- m -toluamide can be used to achieve stabilization of isothiazolones, whereby N, N ' -in the system to be treated. diethyl - m - and the amount of the amide Tolu very small amount, does not interfere with the system to which the other components in the system or the protection system that protects the application requirements.

상기와 같은 본 발명에 따른 이소티아졸론 조성물은 대기중에 매우 안정하여 비교적 장시간 보관하여도 그 약효는 지속되고, 박테리아, 곰팡이, 효모 또는 조류에 의하여 오염되는 어떠한 영역에도 사용이 가능하다.The isothiazolone composition according to the present invention as described above is very stable in the air, and even after being stored for a relatively long time, its medicinal effect persists and can be used in any area contaminated by bacteria, fungi, yeast or algae.

즉, 살균제, 위생제, 청정제, 탈취제, 액체 및 가루비누, 오일 및 그리이스제거제, 음식처리용 화학제품, 일용화학제품, 음식보존제, 동물사료보존제, 목제보존제, 도료, 래주어(lazures),염색액, 방미제, 병원 및 의료방부제, 금속작업제, 냉각수, 공기청정제, 석유제조시, 종이처리시, 제지공장슬라임방지제, 석유산물, 접착제, 섬유, 안료슬러리, 라텍스, 가죽 및 피혁처리, 석유연료, 세탁소독제, 농경배합사료, 잉크, 채광, 부직포, 석유저장소, 호재, 고무, 제당, 담배, 수영장, 화장품, 화장실용품, 풀, 플라스틱, 카드보오드, 의약품, 화학적화장지, 가정세탁물, 디젤연료첨가제, 왁스, 코오크, 윤활제, 건축용품, 콘크리이트배합제 또는 광택제와 기타 바람직하지 않은 미생물이 성장할 수 있는 환경과 접촉하는 유기물 및 수분이 있는 영역 어디에나 사용이 가능하다.Ie disinfectants, sanitizers, detergents, deodorants, liquid and powdered soaps, oil and grease removers, food processing chemicals, daily chemicals, food preservatives, animal feed preservatives, wood preservatives, paints, lazures, dyeing Liquid, antiseptic, hospital and medical preservative, metal working agent, cooling water, air cleaner, petroleum manufacturing, paper processing, paper mill slime inhibitor, petroleum products, adhesive, fiber, pigment slurry, latex, leather and leather treatment, petroleum Fuel, laundry detergent, agricultural compound feed, ink, mining, non-woven fabric, oil storage, good materials, rubber, sugar, tobacco, swimming pool, cosmetics, toiletries, glue, plastic, card board, pharmaceuticals, chemical toilet paper, household laundry, diesel fuel Use anywhere in areas of organic matter and moisture that are in contact with the environment where additives, waxes, cokes, lubricants, building supplies, concrete blends or polishes and other undesirable microorganisms may grow. Neunghada.

이하, 본 발명을 실시예에 의거하여 상세히 설명하면 다음과 같은 바, 본 발명이 실시예에 의해 한정되는 것은 아니다.Hereinafter, the present invention will be described in detail with reference to the following Examples, but the present invention is not limited by the Examples.

모든 퍼센트는 중량%이고 사용되는 모든 시약은 양호한 상태의 공업용 등급의 시 약들이다.All percentages are by weight and all reagents used are industrial grade reagents in good condition.

또한, 다음 실시예 1 내지 13 및 비교예 1 내지 9에서 제조된 이소티아졸론 용액은 각각 65℃ 항온조에 방치한 후 열안정성을 측정하였으며, 열안정성 측정에 의한 분해정도는 고성능 액체크로마토그래피(HPLC, High Performance Liquid Chromatography)로 측정하였다. 잔류함량(%) 측정결과는 다음 표 1, 2 및 3에 나타내었다.In addition, the isothiazolone solutions prepared in Examples 1 to 13 and Comparative Examples 1 to 9, respectively, were then placed in a 65 ° C. thermostatic chamber, and then thermal stability was measured. The decomposition degree by thermal stability measurement was high performance liquid chromatography (HPLC). , High Performance Liquid Chromatography). Residual content (%) measurement results are shown in the following Tables 1, 2 and 3.

실시예 1Example 1

5-클로로-2-메틸-3-이소티아졸론과 2-메틸-3-이소티아졸론이 3 : 1 중량비로 혼합된 이소티아졸론 혼합물 4.5 중량%,N,N'-디에틸-m-톨루아마이드 9 중량% 및 디에틸렌 글리콜 85.5 중량%를 혼합하여 이소티아졸론 용액을 제조하였다.4.5 wt% of an isothiazolone mixture of 5-chloro-2-methyl-3-isothiazolone and 2-methyl-3-isothiazolone in a 3: 1 weight ratio, N, N' -diethyl- m -tolu An isothiazolone solution was prepared by mixing 9% by weight amide and 85.5% by weight diethylene glycol.

실시예 2Example 2

상기 실시예 1과 같은 조성으로 이소티아졸론 용액을 제조하되, 다만 용매로서 디에틸렌 글리콜 86.5 중량% 대신에 디에틸렌 글리콜 메틸 에테르 86.5 중량%를 사용하였다.An isothiazolone solution was prepared in the same composition as in Example 1, except that 86.5 wt% of diethylene glycol methyl ether was used instead of 86.5 wt% of diethylene glycol as a solvent.

실시예 3Example 3

상기 실시예 1과 같은 조성으로 이소티아졸론 용액을 제조하되, 다만 용매로서 디에틸렌 글리콜 86.5 중량% 대신에 디에틸렌 글리콜 디메틸 에테르 86.5중량%를 사용하였다.An isothiazolone solution was prepared in the same composition as in Example 1, except that 86.5 wt% of diethylene glycol dimethyl ether was used instead of 86.5 wt% of diethylene glycol as a solvent.

비교예 1Comparative Example 1

5-클로로-2-메틸-3-이소티아졸론과 2-메틸-3-이소티아졸론이 3 : 1 중량비로 혼합된 이소티아졸론 혼합물 4.5 중량% 와 디에틸렌 글리콜 95.5 중량%를 혼합하여 이소티아졸론 용액을 제조하였다.Isothia by mixing 4.5% by weight of an isothiazolone mixture containing 5-chloro-2-methyl-3-isothiazolone and 2-methyl-3-isothiazolone in a 3: 1 weight ratio and 95.5% by weight of diethylene glycol. A jolon solution was prepared.

비교예 2Comparative Example 2

상기 비교예 1과 같은 조성으로 이소티아졸론 용액을 제조하되, 다만 용매로서 디에틸렌 글리콜 95.5 중량% 대신에 에틸렌 글리콜 메틸 에테르 95.5 중량%를 사용하였다.An isothiazolone solution was prepared in the same composition as Comparative Example 1, except that 95.5% by weight of ethylene glycol methyl ether was used instead of 95.5% by weight of diethylene glycol.

비교예 3Comparative Example 3

상기 비교예 1과 같은 조성으로 이소티아졸론 용액을 제조하되, 다만 용매로서 디에틸렌 글리콜 95.5 중량% 대신에 에틸렌 글리콜 디메틸 에테르 95.5 중량%를 사용하였다.An isothiazolone solution was prepared in the same composition as Comparative Example 1, except that 95.5% by weight of ethylene glycol dimethyl ether was used instead of 95.5% by weight of diethylene glycol.

실시예 4Example 4

5-클로로-2-메틸-3-이소티아졸론과 2-메틸-3-이소티아졸론이 1 : 5 중량비로 혼합된 이소티아졸론 혼합물 2.5 중량%,N,N'-디에틸-m-톨루아마이드 10 중량% 및 디에틸렌 글리콜 87.5 중량%를 혼합하여 이소티아졸론 용액을 제조하였다.2.5% by weight of an isothiazolone mixture of 5-chloro-2-methyl-3-isothiazolone and 2-methyl-3-isothiazolone in a 1: 5 weight ratio, N, N' -diethyl- m -tolu An isothiazolone solution was prepared by mixing 10 wt% amide and 87.5 wt% diethylene glycol.

실시예 5Example 5

상기 실시예 4와 같은 조성으로 이소티아졸론 용액을 제조하되, 다만 용매로서 디에틸렌 글리콜 87,5 중량% 대신에 디에틸렌 글리콜 메틸 에테르 87.5 중량%를사용하였다.An isothiazolone solution was prepared in the same composition as in Example 4, except that 87.5 wt% of diethylene glycol methyl ether was used instead of 87,5 wt% of diethylene glycol as a solvent.

실시예 6Example 6

상기 실시예 4와 같은 조성으로 이소티아졸론 용액을 제조하되, 다만 용매로서 디에틸렌 글리콜 87.5 중량% 대신에 디에틸렌 글리콜 디메틸 에테르 87.5중량%를 사용하였다.An isothiazolone solution was prepared in the same composition as in Example 4, except that 87.5 wt% of diethylene glycol dimethyl ether was used instead of 87.5 wt% of diethylene glycol as a solvent.

실시예 7Example 7

상기 실시예 4와 같은 조성으로 이소티아졸론 용액을 제조하되, 다만 용매로서 디에틸렌 글리콜 87.5 중량% 대신에 디에틸렌 글리콜 메틸 에테르 45 중량% 와 디프로필렌 글리콜 42.5 중량%를 사용하였다.An isothiazolone solution was prepared in the same composition as in Example 4, except that 45% by weight of diethylene glycol methyl ether and 42.5% by weight of dipropylene glycol were used instead of 87.5% by weight of diethylene glycol.

실시예 8Example 8

상기 실시예 4와 같은 조성으로 이소티아졸론 용액을 제조하되, 다만 용매로서 디에틸렌 글리콜 87.5 중량% 대신에 디에틸렌 글리콜 디메틸 에테르 45 중량% 와 디프로필렌 글리콜 42.5 중량%를 사용하였다.An isothiazolone solution was prepared in the same composition as Example 4 except using 45% by weight of diethylene glycol dimethyl ether and 42.5% by weight of dipropylene glycol instead of 87.5% by weight of diethylene glycol.

비교예 4Comparative Example 4

5-클로로-2-메틸-3-이소티아졸론과 2-메틸-3-이소티아졸론이 1 : 5 중량비로 혼합된 이소티아졸론 혼합물 2.5 중량%와 디에틸렌 글리콜 97.5 중량%를 혼합하여 이소티아졸론 용액을 제조하였다.Isothia by mixing 2.5% by weight of an isothiazolone mixture containing 5-chloro-2-methyl-3-isothiazolone and 2-methyl-3-isothiazolone in a 1: 5 weight ratio and 97.5% by weight of diethylene glycol. A jolon solution was prepared.

비교예 5Comparative Example 5

상기 비교예 4와 같은 조성으로 이소티아졸론 용액을 제조하되, 다만 용매로서 디에틸렌 글리콜 97.5 중량% 대신에 에틸렌 글리콜 메틸 에테르 97.5 중량%를사용하였다.An isothiazolone solution was prepared in the same composition as Comparative Example 4, except that 97.5 wt% of ethylene glycol methyl ether was used instead of 97.5 wt% of diethylene glycol as a solvent.

비교예 6Comparative Example 6

상기 비교예 4와 같은 조성으로 이소티아졸론 용액을 제조하되, 다만 용매로서 디에틸렌 글리콜 97.5 중량% 대신에 에틸렌 글리콜 디메틸 에테르 97.5 중량%를 사용하였다.An isothiazolone solution was prepared in the same composition as Comparative Example 4, except that 97.5 wt% of ethylene glycol dimethyl ether was used instead of 97.5 wt% of diethylene glycol as a solvent.

실시예 9Example 9

5-클로로-2-메틸-3-이소티아졸론과 2-메틸-3-이소티아졸론이 3:1 중량비로 혼합된 이소티아졸론 혼합물 14.5 중량%,N,N'-디에틸-m-톨루아마이드 15 중량% 및 디에틸렌 글리콜 70.5 중량%를 혼합하여 이소티아졸론 용액을 제조하였다.14.5% by weight of an isothiazolone mixture of 5-chloro-2-methyl-3-isothiazolone and 2-methyl-3-isothiazolone in a 3: 1 weight ratio, N, N' -diethyl- m -tolu An isothiazolone solution was prepared by mixing 15% by weight amide and 70.5% by weight diethylene glycol.

실시예 10Example 10

상기 실시예 9와 같은 조성으로 이소티아졸론 용액을 제조하되, 다만 용매로서 디에틸렌 글리콜 70.5 중량% 대신에 디에틸렌 글리콜 메틸 에테르 70.5 중량%를 사용하였다.An isothiazolone solution was prepared in the same composition as Example 9, except that 70.5 wt% of diethylene glycol methyl ether was used instead of 70.5 wt% of diethylene glycol as a solvent.

실시예 11Example 11

상기 실시예 9와 같은 조성으로 이소티아졸론 용액을 제조하되, 다만 용매로서 디에틸렌 글리콜 70.5 중량% 대신에 디에틸렌 글리콜 디메틸 에테르 70.5중량%를 사용하였다.An isothiazolone solution was prepared in the same composition as Example 9, except that 70.5% by weight of diethylene glycol dimethyl ether was used instead of 70.5% by weight of diethylene glycol.

실시예 12Example 12

상기 실시예 9와 같은 조성으로 이소티아졸론 용액을 제조하되, 다만 용매로서 디에틸렌 글리콜 70.5 중량% 대신에 디에틸렌 글리콜 디메틸 에테르 35 중량% 와 디프로필렌 글리콜 35.5 중량%를 사용하였다.An isothiazolone solution was prepared in the same composition as Example 9, except that 35 wt% diethylene glycol dimethyl ether and 35.5 wt% dipropylene glycol were used instead of 70.5 wt% of diethylene glycol as a solvent.

실시예 13Example 13

상기 실시예 9와 같은 조성으로 이소티아졸론 용액을 제조하되, 다만 용매로서 디에틸렌 글리콜 70.5 중량% 대신에 디에틸렌 글리콜 디메틸 에테르 중량% 와 디프로필렌 글러콜 35.5 중량%를 사용하였다.An isothiazolone solution was prepared in the same composition as Example 9, except that diethylene glycol dimethyl ether and 35.5 wt% of dipropylene glycol were used instead of 70.5 wt% of diethylene glycol as a solvent.

비교예 7Comparative Example 7

5-클로로-2-메틸-3-이소티아졸론과 2-메틸-3-이소티아졸론이 3 : 1 중량비로 혼합된 이소티아졸론 혼합물 14.5 중량%와 디에틸렌 글리콜 85.5 중량%를 혼합하여 이소티아졸론 용액을 제조하였다.Isothia by mixing 14.5 wt% of an isothiazolone mixture containing 5-chloro-2-methyl-3-isothiazolone and 2-methyl-3-isothiazolone in a 3: 1 weight ratio and 85.5 wt% of diethylene glycol A jolon solution was prepared.

비교예 8Comparative Example 8

상기 비교예 7과 같은 조성으로 이소티아졸론 용액을 제조하되, 다만 용매로서 디에틸렌 글리콜 85.5 중량% 대신에 에틸렌 글리콜 메틸 에테르 85.5 중량%를 사용하였다.An isothiazolone solution was prepared in the same composition as Comparative Example 7, except that 85.5% by weight of ethylene glycol methyl ether was used instead of 85.5% by weight of diethylene glycol.

비교예 9Comparative Example 9

상기 비교예 7과 같은 조성으로 이소티아졸론 용액을 제조하되, 다만 용매로서 디에틸렌 글리콜 85.5 중량% 대신에 에틸렌 글리콜 디메틸 에테르 85.5 중량%를 사용하였다.An isothiazolone solution was prepared in the same composition as Comparative Example 7, except that 85.5% by weight of ethylene glycol dimethyl ether was used instead of 85.5% by weight of diethylene glycol.

Claims (8)

다음 구조식(I)로 표시되는 3-이소티아졸론 화합물과N,N'-디에틸-m-톨루아마이드 및 용매로 이루어진 것임을 특징으로 하는 이소티아졸론 조성물.An isothiazolone composition comprising a 3-isothiazolone compound represented by the following formula (I), N, N' -diethyl-m-toluamide and a solvent. 상기식 에서,In the above formula, R1및 R2는 각각 서로 같거나 다른 것으로서, 수소원자 ; 할로겐원자, 또는 C1~ C4의 알킬기 이고,R 1 and R 2 are the same as or different from each other, and a hydrogen atom; A halogen atom or an alkyl group of C 1 to C 4 , R3는 수소원자 ; 할로겐원자 ; 또는 히드록시기로 치환되거나 치환되지 않은 C1~C10의 알킬기 ; 할로겐원자로 치환되거나 치환되지 않은 C2~C10의 알케닐기 ; 할로겐윈자로 치환되거나 치환되지 않은 C2~C10의 알키닐기 ; 할로겐원자, C1~C10의 알킬기 또는 C2~C9의 알콕시기로 치환되거나 치환되지 않은 아랄킬기이다.R 3 is a hydrogen atom; Halogen atom; Or a C 1 to C 10 alkyl group unsubstituted or substituted with a hydroxy group; C 2 -C 10 alkenyl group unsubstituted or substituted with a halogen atom; An alkynyl group of C 2 to C 10 unsubstituted or substituted with a halogen atom; Or an aralkyl group which is unsubstituted or substituted with a halogen atom, a C 1 to C 10 alkyl group or a C 2 to C 9 alkoxy group. 제 1 항에 있어서, 상기 3-이소티아졸론 화합물은 5-클로로-2-메틸-3-이소티아졸론, 2-메틸-3-이소티아졸론, 2-n-옥틸-3-이소티아졸론, 4,5-디클로로-2-시클로헥실-3-이소티아졸론 및 4,5-디클로로-2-n-옥틸-3-이소티아졸론 중에서 선택된 단독 화합물 또는 2종 이상의 혼합물임을 특징으로 하는 이소티아졸론 조성물.The method of claim 1, wherein the 3-isothiazolone compound is 5-chloro-2-methyl-3-isothiazolone, 2-methyl-3-isothiazolone, 2-n-octyl-3-isothiazolone, Isothiazolone, characterized in that it is a single compound or a mixture of two or more selected from 4,5-dichloro-2-cyclohexyl-3-isothiazolone and 4,5-dichloro-2-n-octyl-3-isothiazolone Composition. 제 1 항에 있어서, 상기N,N'-디에틸-m-톨루아마이드와 3-이소티아졸론의 혼합비는 1 : 50 ~ 20 : 1 중량비임을 특징으로 하는 이소티아졸론 조성물.The isothiazolone composition according to claim 1, wherein the mixing ratio of N, N' -diethyl-m-toluamide and 3-isothiazolone is 1:50 to 20: 1 by weight. 제 1 항에 있어서, 상기 용매는 알코올, 폴리올, 글리콜 에테르류임을 특징으로 하는 이소티아졸론 조성물.The isothiazolone composition according to claim 1, wherein the solvent is alcohol, polyol, glycol ethers. 제 1 항에 있어서, 상기 조성물은 상기 구조식(I)로 표시되는 3-이소티아졸론 화합물 0.01 ~ 99 중량%,N,N'-디에틸-m-톨루아마이드 0.01 ~ 99 중량% 및 용매 중량% 이하로 이루어진 것임을 특징으로 하는 이소티아졸론 조성물.According to claim 1, wherein the composition is 0.01 to 99% by weight of the 3-isothiazolone compound represented by the formula (I), 0.01 to 99% by weight of N, N' -diethyl-m- toluamide and solvent weight% Isothiazolone composition characterized by consisting of the following. 안정화 유효량의 N,N'-디에틸-m-톨루아마이드를 다음 구조식(I)로 표시되는 3-이소티아졸론 화합물에 혼합시키는 것을 특징으로 하는 이소터아졸론의 안정화방법.A method for stabilizing isoterazolone, characterized in that a stabilizing effective amount of N, N'-diethyl-m-toluamide is mixed with a 3-isothiazolone compound represented by the following structural formula (I). 상기식에서, R1, R2및 R3는 상기 1항에서 정의한 바와 같다.Wherein R 1 , R 2 and R 3 are as defined in claim 1 above. 제 6 항에 있어서, 상기N,N'-디에틸-m-톨루아마이드와 3-이소티아졸론의 혼합비가 1:100 내지 1000:1 중량비임을 특징으로 하는 안정화방법.7. The stabilization method according to claim 6, wherein the mixing ratio of N, N' -diethyl-m-toluamide and 3-isothiazolone is 1: 100 to 1000: 1 by weight. 다음 구조식(I)로 표시되는 3-이소티아졸론 화합물과N,N'-디에틸-m-톨루아마이드 및 용매로 이루어진 것임을 특징으로 하는 항미생물제.An antimicrobial agent characterized by consisting of a 3-isothiazolone compound represented by the following formula (I), N, N' -diethyl-m-toluamide and a solvent. 상기식에서, R1, R2및 R3는 상기 1항에서 정의한 바와 같다.Wherein R 1 , R 2 and R 3 are as defined in claim 1 above.
KR1019940032167A 1994-11-30 1994-11-30 Stabilized isothiazolone composition KR100313665B1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
KR1019940032167A KR100313665B1 (en) 1994-11-30 1994-11-30 Stabilized isothiazolone composition

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
KR1019940032167A KR100313665B1 (en) 1994-11-30 1994-11-30 Stabilized isothiazolone composition

Publications (2)

Publication Number Publication Date
KR960016718A KR960016718A (en) 1996-06-17
KR100313665B1 true KR100313665B1 (en) 2002-11-29

Family

ID=37531325

Family Applications (1)

Application Number Title Priority Date Filing Date
KR1019940032167A KR100313665B1 (en) 1994-11-30 1994-11-30 Stabilized isothiazolone composition

Country Status (1)

Country Link
KR (1) KR100313665B1 (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR100334554B1 (en) * 1998-03-13 2002-08-21 에스케이씨 주식회사 Magnetic recording medium

Also Published As

Publication number Publication date
KR960016718A (en) 1996-06-17

Similar Documents

Publication Publication Date Title
US5142058A (en) Halogen-containing organic stabilizers for 3-isothiazolones
JPH0818932B2 (en) Stabilized isothiazolone composition
US6403533B2 (en) Stabilized microbicide formulation
KR0171601B1 (en) Method of stabilizing 3-isothiazolones and stabilized 3-isothiazolones compositions
US5049677A (en) Bismuth salt stabilizers for 3-isothiazolones
KR100751003B1 (en) Stable biocidal compositions
US5424324A (en) Use of carbonyl stabilizers for 3-isothiazolones
US5242893A (en) Use of hexamethylenetetramine as a stabilizer for 3-isothiazolones
JP2923129B2 (en) Bromate stabilizers for 3-isothiazolones
IL96354A (en) Stabilized 3-isothiazolone compositions containing carbonyl compounds
KR0179359B1 (en) The use of hexamethylenetetramine as a stabilizer for 3-isothiazolones
KR100313665B1 (en) Stabilized isothiazolone composition
US5145981A (en) Use of antimony salt stabilizers for 3-isothiazolones
KR100324907B1 (en) Stabilized isothiazolone composition from water and ultraviolet rays and method for stabilizing isothiazolone
US5118699A (en) Use of hydrazide stabilizers for 3-isothiazolones
KR100217309B1 (en) Stabilized isothiazolone solution
JP2981865B2 (en) Stabilized isothiazolone solution
KR100324908B1 (en) Stabilized 3-isothiazolone solution from water and ultraviolet rays and method for stabilizing isothiazolone
KR100383098B1 (en) A method inhibiting precipitation of isothiazolone solution and a composition the same

Legal Events

Date Code Title Description
A201 Request for examination
E902 Notification of reason for refusal
E701 Decision to grant or registration of patent right
GRNT Written decision to grant
FPAY Annual fee payment

Payment date: 20120920

Year of fee payment: 12

FPAY Annual fee payment

Payment date: 20130923

Year of fee payment: 13

EXPY Expiration of term