NO138615B - USE OF AN AMINE FOR THE PREPARATION OF AQUATIC, STABLE SOLUTIONS OF 1,2-BENZISOTIAZOLONE - Google Patents
USE OF AN AMINE FOR THE PREPARATION OF AQUATIC, STABLE SOLUTIONS OF 1,2-BENZISOTIAZOLONE Download PDFInfo
- Publication number
- NO138615B NO138615B NO1188/71A NO118871A NO138615B NO 138615 B NO138615 B NO 138615B NO 1188/71 A NO1188/71 A NO 1188/71A NO 118871 A NO118871 A NO 118871A NO 138615 B NO138615 B NO 138615B
- Authority
- NO
- Norway
- Prior art keywords
- benzisothiazolone
- amine
- solutions
- solution
- preparation
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title description 3
- DMSMPAJRVJJAGA-UHFFFAOYSA-N benzo[d]isothiazol-3-one Chemical compound C1=CC=C2C(=O)NSC2=C1 DMSMPAJRVJJAGA-UHFFFAOYSA-N 0.000 claims description 26
- 150000001412 amines Chemical class 0.000 claims description 15
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 9
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 239000000243 solution Substances 0.000 description 20
- 239000000203 mixture Substances 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- 230000002035 prolonged effect Effects 0.000 description 4
- -1 sodium and potassium Chemical class 0.000 description 4
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 3
- 239000012736 aqueous medium Substances 0.000 description 3
- 244000005700 microbiome Species 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- GUUVPOWQJOLRAS-UHFFFAOYSA-N Diphenyl disulfide Chemical compound C=1C=CC=CC=1SSC1=CC=CC=C1 GUUVPOWQJOLRAS-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000000356 contaminant Substances 0.000 description 2
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 208000015181 infectious disease Diseases 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 2
- KANAPVJGZDNSCZ-UHFFFAOYSA-N 1,2-benzothiazole 1-oxide Chemical group C1=CC=C2S(=O)N=CC2=C1 KANAPVJGZDNSCZ-UHFFFAOYSA-N 0.000 description 1
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 1
- LBEMXJWGHIEXRA-UHFFFAOYSA-N 2-[(2-carboxyphenyl)disulfanyl]benzoic acid Chemical compound OC(=O)C1=CC=CC=C1SSC1=CC=CC=C1C(O)=O LBEMXJWGHIEXRA-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- SLINHMUFWFWBMU-UHFFFAOYSA-N Triisopropanolamine Chemical compound CC(O)CN(CC(C)O)CC(C)O SLINHMUFWFWBMU-UHFFFAOYSA-N 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- LVTYICIALWPMFW-UHFFFAOYSA-N diisopropanolamine Chemical compound CC(O)CNCC(C)O LVTYICIALWPMFW-UHFFFAOYSA-N 0.000 description 1
- 229940043276 diisopropanolamine Drugs 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- AJQLEJAVGARHGQ-UHFFFAOYSA-N dithiosalicylic acid Chemical compound OC1=CC=CC=C1C(S)=S AJQLEJAVGARHGQ-UHFFFAOYSA-N 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 150000002169 ethanolamines Chemical class 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 230000000622 irritating effect Effects 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 235000015927 pasta Nutrition 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- NBOMNTLFRHMDEZ-UHFFFAOYSA-N thiosalicylic acid Chemical compound OC(=O)C1=CC=CC=C1S NBOMNTLFRHMDEZ-UHFFFAOYSA-N 0.000 description 1
- 229940103494 thiosalicylic acid Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F1/00—Treatment of water, waste water, or sewage
- C02F1/50—Treatment of water, waste water, or sewage by addition or application of a germicide or by oligodynamic treatment
-
- 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
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Plant Pathology (AREA)
- Environmental Sciences (AREA)
- Hydrology & Water Resources (AREA)
- Environmental & Geological Engineering (AREA)
- Water Supply & Treatment (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Thiazole And Isothizaole Compounds (AREA)
Description
Denne oppfinnelse angår anvendelse åy .visse aminer ved fremstilling av oppløsninger av 1,2-benzisotiazolon. This invention relates to the use of certain amines in the preparation of solutions of 1,2-benzisothiazolone.
1,2-benzisotiazolon er kjent for å være. et meget effektivt middel for beskyttelse av vandige medier mot infeksjon av mikro-organismer. 1,2-benzisothiazolone is known to be a very effective agent for the protection of aqueous media against infection by micro-organisms.
Ved den -eneste kjente, praktisk anvendbare fremstillings-måte erholdes 1,.2-^benzisotiazolon i en urenset form som imidlertid er helt tilfredsstillende for det ovenfor angitte formål, og som hittil er anvendt i form av en vandig dispersjon. eller pasta. In the -only known, practically applicable production method, 1,2-benzisothiazolone is obtained in an impure form which, however, is completely satisfactory for the purpose stated above, and which has hitherto been used in the form of an aqueous dispersion. or pasta.
Slike pastaer er beheftet med den ulempe at de har en tendens til Such pastes suffer from the disadvantage that they tend to
å bli utfelt ved henstand, og de har .også en tendens til å- til-stoppe pumper som anvendes for tilsetning av avpassede mengder av to be precipitated by respite, and they also tend to stop pumps used for adding appropriate amounts of
dispersjonen eller pastaen til vannet som skal behandles. the dispersion or paste to the water to be treated.
Det er derfor ønskelig å tilveiebringe 1,2-benzisotiazolon i form av sterk, stabil oppløsning. It is therefore desirable to provide 1,2-benzisothiazolone in the form of a strong, stable solution.
Det er kjent at 1,2-benzisotiazolon danner salter med alkalimetaller, f.eks. natrium og kalium, og med ammoniakk eller aminer så som trietanolamin, og disse salter er vannoppløselige. Oppløsninger av 1,2-benzisotiazolon i et organisk oppløsningsmiddel, f.eks. etylenglykol eUer dietylenglykol, kan også fremstilles og settes til vann for å danne vandige oppløsninger. Urenset 1,2-benzisotiazolon gir imidlertid ikke stabile vandige oppløsninger med tilstrekkelig styrke ved anvendelse av de ovennevnte metoder. It is known that 1,2-benzisothiazolone forms salts with alkali metals, e.g. sodium and potassium, and with ammonia or amines such as triethanolamine, and these salts are water soluble. Solutions of 1,2-benzisothiazolone in an organic solvent, e.g. ethylene glycol or diethylene glycol can also be prepared and added to water to form aqueous solutions. However, impure 1,2-benzisothiazolone does not give stable aqueous solutions of sufficient strength when using the above methods.
Det er f.eks. ikke mulig å fremstille en vandig opp-løsning av kaliumsaltet av urenset 1,2-benzisotiazolon, med eller uten tilsetning av etylenglykol eller dietylenglykol, med tilstrekkelig styrke til å være kommersielt tilfredsstillende. Monoetanolaminsaltet av 1,2-benzisotiazolon har liten oppløselig-het i vann. Ved anvendelse av dietanolamin er det mulig å fremstille sterke, vandige oppløsninger fra urenset 1,2-benzisotiazolon ved normal temperatur, men når de avkjøles under ca. 10°C gir slike oppløsninger et fast bunnfall. Trietanolamin.er noe bedre i denne henseende, men man får også her et fast bunnfall hvis den.. vandige oppløsning avkjøles under 0°C. Dannelse av faste bunnfall ved lave temperaturer er ufordelaktig, eftersom oppløsningene ofte lagres i friluft i perioder med langvarig kulde. It is e.g. not possible to prepare an aqueous solution of the potassium salt of impure 1,2-benzisothiazolone, with or without the addition of ethylene glycol or diethylene glycol, of sufficient strength to be commercially satisfactory. The monoethanolamine salt of 1,2-benzisothiazolone has little solubility in water. By using diethanolamine, it is possible to prepare strong, aqueous solutions from impure 1,2-benzisothiazolone at normal temperature, but when they are cooled below approx. At 10°C, such solutions give a solid precipitate. Triethanolamine is somewhat better in this respect, but a solid precipitate is also obtained here if the aqueous solution is cooled below 0°C. The formation of solid precipitates at low temperatures is disadvantageous, since the solutions are often stored in the open air during periods of prolonged cold.
I norsk patent 127.845 er beskrevet vandige oppløs-ninger av urenset 1,2-benzisotiazolon i form av en blanding av Norwegian patent 127,845 describes aqueous solutions of impure 1,2-benzisothiazolone in the form of a mixture of
to eller flere forskjellige aminsalter derav, idet aminene velges fra dietanolamin, trietanolamin, diisopropanolamin, triisopropanol-amin bg morfolin. two or more different amine salts thereof, the amines being selected from diethanolamine, triethanolamine, diisopropanolamine, triisopropanolamine bg morpholine.
På denne måte kan man fremstille oppløsninger av 1,2-benzisotiazolon med tilstrekkelig styrke og stabilitet ved temperaturer ned til 0°C eller noe lavere. Disse oppløsninger har imidlertid en tendens til å krystallisere ved lagring ved lave temperaturer og er utilstrekkelig stabile overfor fryse-tine-cykluser ved temperaturer i området rundt -10°C. In this way, solutions of 1,2-benzisothiazolone with sufficient strength and stability can be prepared at temperatures down to 0°C or somewhat lower. However, these solutions tend to crystallize when stored at low temperatures and are insufficiently stable to freeze-thaw cycles at temperatures in the region of -10°C.
Vi har nu funnet at disse vanskeligheter kan unngåes We have now found that these difficulties can be avoided
ved anvendelse av oppløsninger av 1,2-benzisotiazolon i visse aminer. 1,2-benzisotiazolon vil være tilstede i oppløsningen i form av sitt aminsalt. using solutions of 1,2-benzisothiazolone in certain amines. 1,2-Benzisothiazolone will be present in the solution in the form of its amine salt.
I henhold til foreliggende oppfinnelse anvendes et amin med den generelle formel According to the present invention, an amine with the general formula is used
hvor enten n = 2 og m = 1-3 where either n = 2 and m = 1-3
eller n = 3 og m = 1-2, or n = 3 and m = 1-2,
eller et amin med den generelle formel or an amine of the general formula
hvor x = 1-3, where x = 1-3,
eller pyrrolidin, or pyrrolidine,
fortrinnsvis etylendiamin, for fremstilling av vandige, stabile oppløsninger av 1,2-benzisotiazolon. preferably ethylenediamine, for the preparation of aqueous, stable solutions of 1,2-benzisothiazolone.
1,2-benzisotiazolon som fremstilles fra difenyldisulfid-2,2'-dikarboksylsyre (ditiosalicylsyre) ved klorering, f.eks, med klor selv eller med en blanding av tionylklorid og sulfurylklorid, for å danne det såkalte tiosalicylsyre-diklorid, 1,2-CD ,H4.(SCI)C0C1. Dette mellomprodukt gir ved behandling med ammoniakk ammoniumsaltet av 1,2-benzisotiazolon, fra hvilket den frie forbindelse lett kan isoleres. 1,2-benzisothiazolone which is prepared from diphenyldisulfide-2,2'-dicarboxylic acid (dithiosalicylic acid) by chlorination, e.g., with chlorine itself or with a mixture of thionyl chloride and sulfuryl chloride, to form the so-called thiosalicylic acid dichloride, 1,2 -CD ,H4.(SCI)COC1. This intermediate product gives, on treatment with ammonia, the ammonium salt of 1,2-benzisothiazolone, from which the free compound can easily be isolated.
Fremstilt på denne måte inneholder.1,2-benzisotiazolon Produced in this way contains.1,2-benzisothiazolone
som hovedforurensning noe 2,2<1->bis(aminokarbonyl)difenyl-disulfid, men dette er ikke ufordelaktig eftersom forurensningen også er effektiv til å beskytte vandige medier mot infeksjon av mikro-organismer.. as the main contaminant some 2,2<1->bis(aminocarbonyl)diphenyl-disulfide, but this is not disadvantageous since the contaminant is also effective in protecting aqueous media against infection by micro-organisms..
Urenset 1,2-benzisotiazolon erholdes direkte fra frem-stillingsprosessen som en vandig pasta som kan tørres„ Dette tørre materialet kan oppløses direkte i ett eller flere av aminene angitt ovenfor, men det foretrekkes å anvende det urensede 1,2-benzisotiazolon i form av en vandig pasta, fordi det tørre produkt inneholder noe støvmateriale som kan ha en noe irriterende virkning, og fordi vann i alle tilfeller tilsettes senere. Unpurified 1,2-benzisothiazolone is obtained directly from the manufacturing process as an aqueous paste which can be dried. This dry material can be dissolved directly in one or more of the amines indicated above, but it is preferred to use the unpurified 1,2-benzisothiazolone in the form of an aqueous paste, because the dry product contains some dust material which can have a somewhat irritating effect, and because water is in all cases added later.
Som eksempler på aminer som kan anvendes, kan nevnes dietylentriamin, trietylentetramin, pyrrolidin, dietylamin og propan-1,3-diamin, men den foretrukne forbindelse er etylendiamin. As examples of amines which can be used, mention may be made of diethylenetriamine, triethylenetetramine, pyrrolidine, diethylamine and propane-1,3-diamine, but the preferred compound is ethylenediamine.
Blandinger av aminer kan anvendes. Mixtures of amines can be used.
Det urensede 1,2-benzisotiazolon, enten tørt elier i form av en vandig pasta, røres sammen med aminet inntil man får en klar oppløsning. Oppløsningsprosessen kan fremmes ved moderat oppvarmning av blandingen. The impure 1,2-benzisothiazolone, either dry or in the form of an aqueous paste, is stirred together with the amine until a clear solution is obtained. The dissolution process can be promoted by moderate heating of the mixture.
Mengden av 1,2-benzisotiazolon og amin som anvendes i henhold til oppfinnelsen kan variere i stor utstrekning, men er generelt i området fra henholdsvis 30 til 38 vekt%, og fra 20 til 30 vekt%, basert på den totale vekt. Det foretrekkes å anvende fra 31,5 til 35,5 vekt% 1,2-benzisotiazolon og fra 20 til 25 The amount of 1,2-benzisothiazolone and amine used according to the invention can vary widely, but is generally in the range from 30 to 38% by weight, and from 20 to 30% by weight, based on the total weight. It is preferred to use from 31.5 to 35.5% by weight of 1,2-benzisothiazolone and from 20 to 25
vekt% amin, og særlig 33,3% 1,2-benzisotiazolon, 24,0% etylendiamin og 4 2,7% vann. % by weight amine, and in particular 33.3% 1,2-benzisothiazolone, 24.0% ethylenediamine and 4 2.7% water.
Den resulterende oppløsning settes normalt til The resulting solution is normally added to
vandige medier i slike mengder at man får 30 til 300 deler 1,2-benzisotiazolon pr. million, alt efter mediets natur og de skadelige mikro-organismer, selv om mengder utenfor dette området også kan anvendes. aqueous media in such quantities that 30 to 300 parts of 1,2-benzisothiazolone are obtained per million, depending on the nature of the medium and the harmful micro-organisms, although amounts outside this range can also be used.
I de følgende eksempler som skal tjene til å illustrere oppfinnelser ytterligere, er alle deler og prosentdeler efter vekt. In the following examples which will serve to further illustrate inventions, all parts and percentages are by weight.
EKSEMPEL 1 EXAMPLE 1
Den følgende komposisjon ble fremstilt: The following composition was produced:
Den således erholdte oppløsning var stabil ved langvarig henstand ved så lave temperaturer som -10°C. The solution thus obtained was stable on prolonged standing at temperatures as low as -10°C.
EKSEMPEL 2 EXAMPLE 2
Den følgende komposisjon ble fremstilt: The following composition was produced:
Den således erholdte oppløsning har et krystallisasjons-punkt under -10°C. The solution thus obtained has a crystallization point below -10°C.
EKSEMPEL 3 EXAMPLE 3
Den "følgende komposisjon ble fremstilt: The "following composition was produced:
Den således erholdte oppløsning har et krystallisasjons-punkt under -10°C. The solution thus obtained has a crystallization point below -10°C.
EKSEMPEL 4 EXAMPLE 4
Den følgende komposisjon ble fremstilt: The following composition was produced:
Den således erholdte oppløsning har et krystallisasjons-punkt under ~10°C. The solution thus obtained has a crystallization point below ~10°C.
EKSEMPEL 5 EXAMPLE 5
Den følgende komposisjon ble fremstilt: The following composition was produced:
Den således erholdte oppløsning har et krystallisasjons-punkt under -10°C. The solution thus obtained has a crystallization point below -10°C.
EKSEMPEL 6 EXAMPLE 6
Den følgende komposisjon ble fremstilt: The following composition was produced:
Den således erholdte oppløsning er stabil ved langvarig henstand ved så lave temperaturer som -10°C. The solution thus obtained is stable during prolonged standing at temperatures as low as -10°C.
EKSEMPEL 7 EXAMPLE 7
Den følgende komposisjon ble fremstilt: The following composition was produced:
Den således erholdte oppløsning er stabil ved langvarig henstand ved så lave temperaturer som -10°C. The solution thus obtained is stable during prolonged standing at temperatures as low as -10°C.
Alle de ovenfor beskrevne komposisjoner ble fremstilt All the compositions described above were prepared
ved å blande aminet og vannet, oppvarme blandingen til en temperatur på 50-60°C, tilsette den urensede 1,2-benzisotiazolonpasta og omrøre blandingen inntil man fikk en klar oppløsning. by mixing the amine and the water, heating the mixture to a temperature of 50-60°C, adding the crude 1,2-benzisothiazolone paste and stirring the mixture until a clear solution was obtained.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1508670 | 1970-03-31 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO138615B true NO138615B (en) | 1978-07-03 |
| NO138615C NO138615C (en) | 1978-10-11 |
Family
ID=10052780
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO1188/71A NO138615C (en) | 1970-03-31 | 1971-03-30 | USE OF AN AMINE FOR THE PREPARATION OF AQUATIC, STABLE SOLUTIONS OF 1,2-BENZISOTIAZOLONE |
Country Status (9)
| Country | Link |
|---|---|
| JP (1) | JPS5410612B1 (en) |
| BE (1) | BE765108A (en) |
| CA (1) | CA970683A (en) |
| FI (1) | FI56118C (en) |
| FR (1) | FR2087938A5 (en) |
| GB (1) | GB1330531A (en) |
| IT (1) | IT1044213B (en) |
| NO (1) | NO138615C (en) |
| ZA (1) | ZA711691B (en) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4291045A (en) | 1976-05-04 | 1981-09-22 | Life Savers, Inc. | Method of reducing dental caries |
| ZA784934B (en) * | 1977-09-30 | 1979-10-31 | Ici Ltd | Solutions of benzisothiazolinones |
| GB8517478D0 (en) * | 1985-07-10 | 1985-08-14 | Ici Plc | Isothiazolone solutions |
| DE3600271A1 (en) * | 1986-01-08 | 1987-07-09 | Cassella Ag | AQUEOUS PREPARATION OF 1,2-BENZISOTHIAZOLIN-3-ON |
| DE3609939A1 (en) * | 1986-03-24 | 1987-10-01 | Cassella Ag | LIQUID PREPARATION OF 1,2-BENZISOTHIAZOLIN-3-ON, ITS PRODUCTION AND USE |
| GB8907298D0 (en) * | 1989-03-31 | 1989-05-17 | Ici Plc | Composition and use |
| DE4033272C1 (en) * | 1990-10-19 | 1991-10-10 | Schuelke & Mayr Gmbh, 2000 Norderstedt, De | |
| US5276047A (en) * | 1991-10-18 | 1994-01-04 | Sterling Winthrop, Inc. | Liquid 1,2-benzoisothiazoline-3-one preparation |
| GB9300936D0 (en) * | 1993-01-19 | 1993-03-10 | Zeneca Ltd | Stable liquid compositions and their use |
| US5585033A (en) | 1995-07-21 | 1996-12-17 | Huls America Inc. | Liquid formulations of 1,2-benzisothiazolin-3-one |
| EP1772055A1 (en) * | 2005-10-04 | 2007-04-11 | Rohm and Haas France SAS | Synergistic microbicidal compositions comprising a N-alkyl-1,2-benzoisothiazolin-3-one |
| DE102007037013A1 (en) | 2007-08-06 | 2009-02-19 | Clariant International Ltd. | Biocidal compositions |
| EP2042489A1 (en) * | 2007-09-26 | 2009-04-01 | Straetmans high TAC GmbH | Removal and prevention of discolouration of pyrithione-containing materials |
| WO2012158425A1 (en) * | 2011-05-13 | 2012-11-22 | Isp Investments Inc. | Aqueous solutions of 1,2-benzisothiazolin-3-one |
| EP2596702B1 (en) * | 2011-11-25 | 2015-05-27 | Omya International AG | Process for stabilizing bacterial content of aqueous ground natural calcium carbonate and/or precipitated calcium carbonate and/or dolomite and/or surface-reacted calcium carbonate-comprising mineral preparations |
| ES2928076T3 (en) | 2015-12-23 | 2022-11-15 | Henkel Ag & Co Kgaa | metal working fluid |
| WO2017140412A1 (en) | 2016-02-15 | 2017-08-24 | Thor Gmbh | Temperature-stable biocide composition for metal-working liquids |
-
1970
- 1970-03-31 GB GB1508670A patent/GB1330531A/en not_active Expired
-
1971
- 1971-03-15 ZA ZA711691A patent/ZA711691B/en unknown
- 1971-03-17 FI FI764/71A patent/FI56118C/en active
- 1971-03-30 FR FR7111177A patent/FR2087938A5/fr not_active Expired
- 1971-03-30 NO NO1188/71A patent/NO138615C/en unknown
- 1971-03-31 BE BE765108A patent/BE765108A/en not_active IP Right Cessation
- 1971-03-31 CA CA109,273A patent/CA970683A/en not_active Expired
- 1971-03-31 JP JP1959171A patent/JPS5410612B1/ja active Pending
- 1971-03-31 IT IT22581/71A patent/IT1044213B/en active
Also Published As
| Publication number | Publication date |
|---|---|
| CA970683A (en) | 1975-07-08 |
| IT1044213B (en) | 1980-03-20 |
| BE765108A (en) | 1971-09-30 |
| FI56118C (en) | 1979-12-10 |
| JPS5410612B1 (en) | 1979-05-08 |
| FI56118B (en) | 1979-08-31 |
| FR2087938A5 (en) | 1971-12-31 |
| GB1330531A (en) | 1973-09-19 |
| NO138615C (en) | 1978-10-11 |
| ZA711691B (en) | 1972-01-26 |
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