KR970042527A - Process for preparing stabilized isothiazolone composition and isothiazolone mixture - Google Patents

Process for preparing stabilized isothiazolone composition and isothiazolone mixture Download PDF

Info

Publication number
KR970042527A
KR970042527A KR1019960038208A KR19960038208A KR970042527A KR 970042527 A KR970042527 A KR 970042527A KR 1019960038208 A KR1019960038208 A KR 1019960038208A KR 19960038208 A KR19960038208 A KR 19960038208A KR 970042527 A KR970042527 A KR 970042527A
Authority
KR
South Korea
Prior art keywords
methyl
isothiazolin
mixture
represented
ppm
Prior art date
Application number
KR1019960038208A
Other languages
Korean (ko)
Other versions
KR100212963B1 (en
Inventor
한순종
김진만
김승환
임진수
Original Assignee
김준웅
주식회사 선경인더스트리
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
Family has litigation
First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=19442354&utm_source=***_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=KR970042527(A) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Application filed by 김준웅, 주식회사 선경인더스트리 filed Critical 김준웅
Publication of KR970042527A publication Critical patent/KR970042527A/en
Application granted granted Critical
Publication of KR100212963B1 publication Critical patent/KR100212963B1/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D275/00—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings
    • C07D275/02—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings not condensed with other rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
    • A61Q17/005—Antimicrobial preparations
    • 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
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L3/00—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs
    • A23L3/34—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs by treatment with chemicals
    • A23L3/3454—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs by treatment with chemicals in the form of liquids or solids
    • A23L3/3463—Organic compounds; Microorganisms; Enzymes
    • A23L3/3526—Organic compounds containing nitrogen
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L3/00—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs
    • A23L3/34—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs by treatment with chemicals
    • A23L3/3454—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs by treatment with chemicals in the form of liquids or solids
    • A23L3/3463—Organic compounds; Microorganisms; Enzymes
    • A23L3/3544—Organic compounds containing hetero rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D275/00—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings
    • C07D275/02—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings not condensed with other rings
    • C07D275/03—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings not condensed with other rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/52—Stabilizers
    • A61K2800/524—Preservatives

Landscapes

  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Microbiology (AREA)
  • Food Science & Technology (AREA)
  • Polymers & Plastics (AREA)
  • Nutrition Science (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Public Health (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Epidemiology (AREA)
  • Birds (AREA)
  • Dermatology (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Dentistry (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Thiazole And Isothizaole Compounds (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Food Preservation Except Freezing, Refrigeration, And Drying (AREA)

Abstract

본 발명은 안정화된 이소티아졸론 조성물과 이소티아조론 혼합물의 제조방법에 관한 것으로서, 더욱 상세하게는 다음 구조식(A-1)로 표시되는 N-메틸-3-머캅토프로피온아미드 또는 다음 구조식(A-2)로 표시되는 N,N'-디메틸-3,3'-머캅토프로피온아미드를 출발물질로 하여 클로로화반응 및 고리화반응시키되, 반응계내의 온도를 5∼20℃로 유지시키는 조건에서 반응시켜서 피부자극물질로 알려진 4,5-디클로로-2-메틸-4-이소티아졸린-3-온의 생성을 극단적으로 최소화하여 실질적으로 이의 생성을 억제시키고, 또한 반응공정후 원심분리에 의한 정제 공정을 부가적으로 수행하여 N,N'-디메틸-3,3'-디티오디프로피온아미드를 출발물질로 사용함에 따라 필연적으로 생성되는 니트로소아민 전구체를 완벽하게 제거시킬 수 있게 하므로써 각종 살균제 또는 방부제로 널리 이용되고 있는 다음 구조식(Ⅰ)과 (Ⅱ)로 표시되는 2-메틸-4-이소티아졸린-3-온 혼합물을 고순도 및 고수율로 제조하는 방법과 4,5-디클로로-2-메틸-4-이소티아졸린-3-온을 함유하지 않는 이소티아졸론 혼합물, 그리고 이러한 이소티아졸론 혼합물을 유효성분으로 하는 안정화된 이소티아졸론 조성물과 안정화된 이소티아 졸론 수용액에 관한 것이다.The present invention relates to a method for preparing a stabilized isothiazolone composition and an isothiazolone mixture, more particularly N-methyl-3-mercaptopropionamide represented by the following structural formula (A-1) or the following structural formula (A Chlorination reaction and cyclization reaction using N, N'-dimethyl-3,3'-mercaptopropionamide represented by -2) as starting materials, and the reaction is carried out under the condition that the temperature in the reaction system is maintained at 5-20 ° C By minimizing the production of 4,5-dichloro-2-methyl-4-isothiazolin-3-one, known as a skin irritant, substantially inhibiting its production, and further purifying by centrifugation after the reaction process. In addition, by using N, N'-dimethyl-3,3'-dithiodipropionamide as a starting material, it is possible to completely remove the nitrosoamine precursor that is inevitably produced as various fungicides or preservatives.To prepare a 2-methyl-4-isothiazolin-3-one mixture represented by the following structural formula (I) and (II) in high purity and high yield and 4,5-dichloro-2-methyl- The isothiazolone mixture which does not contain 4-isothiazolin-3-one, and the stabilized isothiazolone composition and stabilized isothiazolone aqueous solution which make this isothiazolone mixture an active ingredient.

Description

안정화된 이소티아졸론 조성물과 이소티아졸론 혼합물의 제조방법Process for preparing stabilized isothiazolone composition and isothiazolone mixture

본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음Since this is an open matter, no full text was included.

Claims (18)

a) 다음 구조식(Ⅰ)과 (Ⅱ)로 표시되는 2-메틸-4-이소티아졸린-3-온 혼합물 생물학적 유효량; b) 질산금속 안정화량; 그리고 c) 상기 a)와 b)를 녹이기에 충분한 양의 물이 함유되어 있고, 상기 이소티아졸론 혼합물 1500 ppm에 대하여 4,5-디클로로-2-메틸-4-이소티아졸린-3-온이 100ppm 미만으로 함유된 것임을 특징으로 하는 안정화된 이소티아졸론 조성물.a) a biologically effective amount of the 2-methyl-4-isothiazolin-3-one mixture represented by the following structural formulas (I) and (II); b) metal nitrate stabilization amount; And c) a sufficient amount of water to dissolve the a) and b) and 4,5-dichloro-2-methyl-4-isothiazolin-3-one per 1500 ppm of the isothiazolone mixture. Stabilized isothiazolone composition, characterized in that it is contained less than 100ppm. 제 1 항에 있어서, 상기 이소티아졸론 혼합물 15000ppm에 대하여 4,5-디클로로-2-메틸-4-이소티아졸린-3-온이 20ppm 미만으로 함유된 것임을 특징으로 하는 안정화된 이소티아졸론 조성물.The stabilized isothiazolone composition according to claim 1, wherein 4,5-dichloro-2-methyl-4-isothiazolin-3-one is contained in an amount of less than 20 ppm relative to 15000 ppm of the isothiazolone mixture. 제 1 항에 있어서, 상기 이소티아졸론 조성물의 색도(APHA Color)가 50 이하인 것을 특징으로 하는 안정화된 이소티아졸론 용액.2. The stabilized isothiazolone solution of claim 1 wherein the isothiazolone composition has an APHA Color of 50 or less. 다음 구조식(Ⅰ)과 (Ⅱ)로 표시되는 2-메틸-4-이소티아졸린-3-온 혼합물 생물학적 유효량; b) 질산금속 안정화량; 그리고 c) 상기 a)와 b)를 녹이기에 충분한 양의 물이 함유되어 있고, 상기 이소티아졸론 혼합물 1500 ppm에 대하여 4,5-디클로로-2-메틸-4-이소티아졸린-3-온이 100ppm 미만으로 함유됨과 동시에 니트로소아민 또는 이드르이 전구체가 50ppm 미만으로 함유된 것임을 특징으로 하는 안정화된 이소티아졸론 조성물.A biologically effective amount of the 2-methyl-4-isothiazolin-3-one mixture represented by the following structural formulas (I) and (II); b) metal nitrate stabilization amount; And c) a sufficient amount of water to dissolve the a) and b) and 4,5-dichloro-2-methyl-4-isothiazolin-3-one per 1500 ppm of the isothiazolone mixture. A stabilized isothiazolone composition characterized by containing less than 100 ppm and simultaneously containing less than 50 ppm of nitrosoamine or idru precursor. 제 4 항에 있어서, 상기 이소티아졸론 혼합물 15000ppm에 대하여 4,5-디클로로-2-메틸-4-이소티아졸린-3-온이 20ppm 미만으로 함유된 것임을 특징으로 하는 안정화된 이소티아졸론 조성물.5. The stabilized isothiazolone composition according to claim 4, wherein less than 20 ppm of 4,5-dichloro-2-methyl-4-isothiazolin-3-one is contained relative to 15000 ppm of the isothiazolone mixture. 제 4 항에 있어서, 상기 이소티아졸론 조성물의 색도(APHA Color)가 50 이하인 것을 특징으로 하는 안정화된 이소티아졸론 조성물.The stabilized isothiazolone composition according to claim 4, wherein the isothiazolone composition has a chromaticity (APHA Color) of 50 or less. 다음 구조식(A-1)로 표시되는 N-메틸-3-머캅토프로피온아미드 또는 다음 구조식(A-2)로 표시되는 N,N'-디메틸-3,3'-디티오디프로피온아미드를 출발물질로 하여 클로로화제와 반응시켜 다음 구조식(Ⅰ)과(Ⅱ)로로 표시되는 2-메틸-4-이소티아졸린-3-온 혼합물을 제조하는 방법에 있어서, 상기 출발물질과 클로로화제를 반응기의 온도가 5∼20℃로 유지되는 조건에서 반응시켜서 본질적으로 4,5-디클로로-2-메틸-4-이소티아졸린-3-온이 100 ppm 미만으로 함유되는 것을 특징으로 하는 2-메틸-4-이소티아졸린-3-온 혼합물의 제조방법.N-methyl-3-mercaptopropionamide represented by the following structural formula (A-1) or N, N'-dimethyl-3,3'-dithiodipropionamide represented by the following structural formula (A-2) In the method for producing a 2-methyl-4-isothiazolin-3-one mixture represented by the following structural formula (I) and (II) by reacting with a chloroating agent, the starting material and the chloroating agent Is reacted under the condition that is maintained at 5 to 20 ° C., thereby essentially containing 4,5-dichloro-2-methyl-4-isothiazolin-3-one containing less than 100 ppm of 2-methyl-4- Process for the preparation of isothiazolin-3-one mixtures. 제 7 항에 있어서, 상기 구조식(Ⅰ)과 (Ⅱ)로 표시되는 2-메틸-4-이소티아졸린-3-온 혼합물중에는 4,5-디클로로-2-메틸-4-이소티아졸린-3-온이 20 ppm 미만으로 함유되는 것을 특징으로 하는 2-메틸-4-이소티아졸린-3-온 혼합물의 제조방법.8. The 2-methyl-4-isothiazolin-3-one mixtures represented by the above formulas (I) and (II) include 4,5-dichloro-2-methyl-4-isothiazoline-3. A process for preparing a 2-methyl-4-isothiazolin-3-one mixture, characterized in that it contains less than 20 ppm. 제 7 항에 있어서, 상기 구조식(Ⅰ)과 (Ⅱ)로 표시되는 2-메틸-4-이소티아졸린-3-온 혼합물이 1 : 3 ∼ 10몰비로 제조되는 것을 특징으로 하는 2-메틸-4-이소티아졸린-3-온 혼합물의 제조방법.The 2-methyl-4- isomethyl-isothiazolin-3-one mixture represented by the structural formulas (I) and (II) is prepared in a 1: 3 to 10 molar ratio. Method for preparing a 4-isothiazolin-3-one mixture. 제 7 항, 제 8 항 또는 제 9 항에 있어서, 상기 구조식(Ⅰ)과 (Ⅱ)로 표시되는 2-메틸-4-이소티아졸린-3-온 혼합물을 원심분리하여 니트로소아민 전구체가 50 ppm 미만으로 함유되는 것을 특징으로 하는 2-메틸-4-이소티아졸린-3-온 혼합물의 제조방법.The method of claim 7, 8 or 9, wherein the 2-methyl-4-isothiazolin-3-one mixture represented by the above structural formulas (I) and (II) is centrifuged to obtain a nitrosoamine precursor. A method for producing a 2-methyl-4-isothiazolin-3-one mixture, characterized by containing less than ppm. 다음 구조식(A-1)로 표시되는 N-메틸-3-머캅토프로피온아미드 또는 다음 구조식(A-2)로 표시되는 N,N'-디메틸-3,3'-머캅토프로피온아미드를 출발물질로 하고 이를 클로로화제와 반응시켜 다음 구조식(Ⅰ)과 (Ⅱ)로 표시되는 2-메틸-4-이소티아졸린-3-온 혼합물을 제조하는 방법에 있어서, 상기 출발물질과 클로로화제 각각을 서로 다른 유기용매에 녹여 반응시켜서 4,5-디클로로-2-메틸-4-이소티아졸린-3-온이 100 ppm 미만으로 함유되는 것을 특징으로 하는 2-메틸-4-이소티아졸린-3-온 혼합물의 제조방법.N-methyl-3-mercaptopropionamide represented by the following structural formula (A-1) or N, N'-dimethyl-3,3'-mercaptopropionamide represented by the following structural formula (A-2) In the method for preparing a 2-methyl-4-isothiazolin-3-one mixture represented by the following structural formula (I) and (II) by reacting it with a chloroating agent, the starting material and the chloroating agent are each 2-methyl-4-isothiazolin-3-one characterized by containing less than 100 ppm of 4,5-dichloro-2-methyl-4-isothiazolin-3-one by dissolving in another organic solvent. Method for preparing the mixture. 제 11 항에 있어서, 상기 구조식(Ⅰ)과 (Ⅱ)로 표시되는 2-메틸-4-이소티아졸린-3-온 혼합물중에는 4,5-디클로로-2-메틸-4-이소티아졸린-3-온이 20 ppm 미만으로 함유되는 것을 특징으로 하는 2-메틸-4-이소티아졸린-3-온 혼합물의 제조방법.12. The 4,5-dichloro-2-methyl-4-isothiazoline-3 according to claim 11, wherein in the 2-methyl-4-isothiazolin-3-one mixture represented by structural formulas (I) and (II), A process for preparing a 2-methyl-4-isothiazolin-3-one mixture, characterized in that it contains less than 20 ppm. 제 11 항에 있어서, 상기 구조식(Ⅰ)과 (Ⅱ)로 표시되는 2-메틸-4-이소티아졸린-3-온 혼합물이 1 : 3 ∼ 10몰비로 제조되는 것을 특징으로 하는 2-메틸-4-이소티아졸린-3-온 혼합물의 제조방법.The 2-methyl-4- isomethyl-isothiazolin-3-one mixture represented by the structural formulas (I) and (II) is prepared in a 1: 3 to 10 molar ratio. Method for preparing a 4-isothiazolin-3-one mixture. 제 11 항, 제 12 항 또는 제 13 항에 있어서, 상기 구조식(Ⅰ)과 (Ⅱ)로 표시되는 2-메틸-4-이소티아졸린-3-온 혼합물을 원심분리하여 니트로소아민 전구체가 50 ppm 미만으로 함유되는 것을 특징으로 하는 2-메틸-4-이소티아졸린-3-온 혼합물의 제조방법.The method of claim 11, 12 or 13, wherein the 2-methyl-4-isothiazolin-3-one mixture represented by the above formulas (I) and (II) is centrifuged to give a nitrosoamine precursor. A method for producing a 2-methyl-4-isothiazolin-3-one mixture, characterized by containing less than ppm. 제 11 항에 있어서, 상기 구조식(A-1) 또는 (A-2)로 표시되는 출발물질을 녹이는 유기용매로는 C4∼ C12알킬에스테르, C7∼ C14불포화 또는 포화탄화수소, XCH=CHX, CH2=CX2, CX2=CX2, C8∼C12방향족 탄화수소 C6H(6-n)Xn(이때, n은 1 내지 5의 정수중에서 선택된 것이고, X는 할로겐원자임)중에서 선택하여 사용하는 것을 특징으로 하는 2-메틸-4-이소티아졸린-3-온 혼합물의 제조방법.The method of claim 11, wherein the organic solvent for dissolving the starting material represented by the formula (A-1) or (A-2) is C 4 ~ C 12 alkyl ester, C 7 ~ C 14 unsaturated or saturated hydrocarbon, XCH = CHX, CH 2 = CX 2 , CX 2 = CX 2 , C 8 -C 12 aromatic hydrocarbons C 6 H ( 6- n) Xn, where n is selected from integers of 1 to 5 and X is a halogen atom Method for producing a 2-methyl-4-isothiazolin-3-one mixture, characterized in that it is selected from and used. 제 11 항 또는 제 15 항에 있어서, 상기 구조식 (A-1) 또는 (A-2)로 표시되는 출발물질과 출발물질을 녹이는 유기용매는 1 : 0.2 ∼ 1 : 20 무게비로 사용하는 것을 특징으로 하는 2-메틸-4-이소티아졸린-3-온 혼합물의 제조방법.The organic solvent dissolving the starting material and the starting material represented by Structural Formulas (A-1) or (A-2) is used in a weight ratio of 1: 0.2 to 1:20. Method for preparing a 2-methyl-4-isothiazolin-3-one mixture. 제 11 항에 있어서, 상기 클로로화제를 녹이는 유기용매로는 C2∼ C10알킬에테르, C2∼ C8알킬에스테르, C5∼ C12불포화 포환탄화수소, CH2X2, CHCX3, CX4, CH3CX3, CH2XCH2X(이때, X는 할로겐원자임) 및 C6∼ C10방향족 탄화수소 중에서 선택하여 사용하는 것을 특징으로 하는 2-메틸-4-이소티아졸린-3-온 혼합물의 제조방법.The method of claim 11, wherein the organic solvent for dissolving the chloroating agent is C 2 ~ C 10 alkyl ether, C 2 ~ C 8 alkyl ester, C 5 ~ C 12 unsaturated cyclic hydrocarbon, CH 2 X 2 , CHCX 3 , CX 4 , CH 3 CX 3 , CH 2 XCH 2 X (where X is a halogen atom) and C 6 to C 10 aromatic hydrocarbons are used for use, and 2-methyl-4-isothiazolin-3-one Method for preparing the mixture. 제 11 항 또는 제 17 항에 있어서, 상기 클로로화제와 클로로화제를 녹이는 유기용매는 1 : 1 ∼ 1 : 20 무게비로 사용하는 것을 특징으로 하는 2-메틸-4-이소티아졸린-3-온 혼합물의 제조방법.18. The 2-methyl-4-isothiazolin-3-one mixture according to claim 11 or 17, wherein the organic solvent for dissolving the chloroating agent and the chloroating agent is used in a weight ratio of 1: 1 to 1:20. Manufacturing method.
KR1019960038208A 1995-12-21 1996-09-04 A stabilized isothiazolone composition and process for preparing isothiazolones KR100212963B1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
KR19950053412 1995-12-21
KR101995053412 1995-12-21

Publications (2)

Publication Number Publication Date
KR970042527A true KR970042527A (en) 1997-07-24
KR100212963B1 KR100212963B1 (en) 1999-08-02

Family

ID=19442354

Family Applications (1)

Application Number Title Priority Date Filing Date
KR1019960038208A KR100212963B1 (en) 1995-12-21 1996-09-04 A stabilized isothiazolone composition and process for preparing isothiazolones

Country Status (4)

Country Link
JP (1) JP3022365B2 (en)
KR (1) KR100212963B1 (en)
DE (1) DE19652531C2 (en)
GB (1) GB2308364B (en)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP3732061B2 (en) * 1999-12-27 2006-01-05 株式会社ケミクレア Process for producing 2-alkyl-4-isothiazolin-3-ones
KR100450692B1 (en) * 2002-04-03 2004-10-01 (주)대지화학 Process for isothiazolone compositions
KR100493934B1 (en) * 2002-11-05 2005-06-10 주식회사 한서켐 The manufacturing process for a salt of 2-methyl-4-isothiazoline-3-one
JP5101826B2 (en) * 2006-02-28 2012-12-19 日本曹達株式会社 Water-soluble preparation containing isothiazolone compound and method for stabilizing isothiazolone compound
CN101081031B (en) * 2006-06-02 2011-03-30 罗门哈斯公司 Microbicidal composition
KR101569556B1 (en) * 2009-03-31 2015-11-16 나가세케무텍쿠스가부시키가이샤 Microbicide

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA1189514A (en) * 1982-06-01 1985-06-25 Horst O. Bayer Nitrosamine-free 3-isothiazolones and process
DE3643183A1 (en) * 1986-12-18 1988-06-30 Riedel De Haen Ag METHOD FOR ISOLATING ISOTHIAZOLINE DERIVATIVES
IL97166A (en) * 1991-02-06 1995-10-31 Bromine Compounds Ltd Process for the preparation of 2-methyl-isothiazolin-3-one compounds
GB2274283B (en) * 1991-05-10 1996-01-31 Sunkyong Ind Ltd A process for preparing 4-isothiazolin-3-one

Also Published As

Publication number Publication date
GB2308364B (en) 1998-03-25
KR100212963B1 (en) 1999-08-02
JPH09309807A (en) 1997-12-02
DE19652531C2 (en) 1998-07-02
DE19652531A1 (en) 1997-06-26
GB9621610D0 (en) 1996-12-04
JP3022365B2 (en) 2000-03-21
GB2308364A (en) 1997-06-25

Similar Documents

Publication Publication Date Title
EP0095907B1 (en) Biocidal or biostatic compositions containing 3-isothiazolones, their method of preparation and their uses
KR840002428B1 (en) Process for preparing morpholine derivatives
BG65483B1 (en) Process for preparing 4-trifluoromethylsulphinylpyrazole derivatives
KR970042527A (en) Process for preparing stabilized isothiazolone composition and isothiazolone mixture
CA2145478A1 (en) 3-isothiazolone biocide process
US5453507A (en) Process for preparing 4-isothiazolin-3-one
Jaeger et al. Destructible surfactants based on a silicon-oxygen bond
US5120863A (en) Process for preparation of diacetal compounds
JP2002535381A (en) Preparation of methyl carbazate
US6376680B1 (en) Process for the preparation of 3-isothiazolone mixture and composition comprising the mixture
NZ207592A (en) Method for the production of 1,8-dihydroxy-10-acyl-9-anthrone,and pharmaceutical compositions
DE2804263C3 (en) Process for the preparation of indoline derivatives
KR860009035A (en) Preparation of 11-beta substituted steroids
WO2002000625A3 (en) Process for the preparation of quinoline derivatives
US5904814A (en) Removal of water and ammonia from benzophenone imine reactor effluents
US5068272A (en) Novel polystyrenesulfonate, useful against cardiac arrhythmias
US4010160A (en) Process for the manufacture of 1,3-bis-(β-ethylhexyl)-5-amino-5-methyl-hexahydropyrimidine
KR20040018373A (en) Chloromethylation of thiophene
DE1292664B (en) 1, 2, 3, 5, 6-pentathiacycloheptane, process for its preparation and use
KR0180562B1 (en) Preparation process of 2-methyl-4-isothiazoline-3-on salt
JP3964544B2 (en) Method for producing isothiazolone anhydride
US3222392A (en) N-methyl 2,2-diphenyl-3-hydroxypropyl carbamate
DE2122070A1 (en) 1 Veratryl 4 methyl 5 ethyl 7,8 dimethoxy 2,3 diazabicyclo square brackets to 5,4,0 square brackets to undeca pentaen (1,3,6,8,10) and its use
KR920017995A (en) Aromatic compound, preparation method thereof and composition for inhibiting pests
DE19853863C1 (en) Production of oxadiazolone derivatives useful as herbicide intermediates comprises simultaneously adding a carboxylic acid hydrazide solution and phosgene to a solvent

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
J206 Request for trial to confirm the scope of a patent right
J301 Trial decision

Free format text: TRIAL DECISION FOR CONFIRMATION OF THE SCOPE OF RIGHT REQUESTED 20020403

Effective date: 20040628

J204 Request for invalidation trial [patent]
J301 Trial decision

Free format text: TRIAL DECISION FOR INVALIDATION REQUESTED 20050526

Effective date: 20060131

J2X1 Appeal (before the patent court)

Free format text: INVALIDATION

J2X1 Appeal (before the patent court)

Free format text: INVALIDATION

J2X2 Appeal (before the supreme court)

Free format text: APPEAL BEFORE THE SUPREME COURT FOR INVALIDATION

J202 Request for trial for correction [limitation]
J302 Written judgement (patent court)

Free format text: JUDGMENT (PATENT COURT) FOR INVALIDATION REQUESTED 20060218

Effective date: 20070112

J303 Written judgement (supreme court)

Free format text: JUDGMENT (SUPREME COURT) FOR INVALIDATION REQUESTED 20070131

Effective date: 20070601

J301 Trial decision

Free format text: TRIAL DECISION FOR CORRECTION REQUESTED 20070312

Effective date: 20080424

J302 Written judgement (patent court)

Free format text: JUDGMENT (PATENT COURT) FOR INVALIDATION REQUESTED 20060307

Effective date: 20070112

J303 Written judgement (supreme court)

Free format text: JUDGMENT (SUPREME COURT) FOR INVALIDATION REQUESTED 20070131

Effective date: 20080724

J222 Remand (patent court)

Free format text: REMAND (PATENT COURT) FOR INVALIDATION

J122 Written withdrawal of action (patent court)
FPAY Annual fee payment

Payment date: 20130422

Year of fee payment: 15

FPAY Annual fee payment

Payment date: 20140421

Year of fee payment: 16

FPAY Annual fee payment

Payment date: 20150423

Year of fee payment: 17

FPAY Annual fee payment

Payment date: 20160420

Year of fee payment: 18

EXPY Expiration of term