NO841856L - AGENT FOR ANTIMICROBIAL TREATMENT OF FOODS, USE OF THE AGENT AND PROCEDURE FOR PREPARING IT - Google Patents

AGENT FOR ANTIMICROBIAL TREATMENT OF FOODS, USE OF THE AGENT AND PROCEDURE FOR PREPARING IT

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Publication number
NO841856L
NO841856L NO841856A NO841856A NO841856L NO 841856 L NO841856 L NO 841856L NO 841856 A NO841856 A NO 841856A NO 841856 A NO841856 A NO 841856A NO 841856 L NO841856 L NO 841856L
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agent
group
compound
specified
alkyl
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NO841856A
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Norwegian (no)
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Freimut Riemer
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Freimut Riemer
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Publication of NO841856L publication Critical patent/NO841856L/en

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Classifications

    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23B—PRESERVING, e.g. BY CANNING, MEAT, FISH, EGGS, FRUIT, VEGETABLES, EDIBLE SEEDS; CHEMICAL RIPENING OF FRUIT OR VEGETABLES; THE PRESERVED, RIPENED, OR CANNED PRODUCTS
    • A23B4/00—General methods for preserving meat, sausages, fish or fish products
    • A23B4/14—Preserving with chemicals not covered by groups A23B4/02 or A23B4/12
    • A23B4/18—Preserving with chemicals not covered by groups A23B4/02 or A23B4/12 in the form of liquids or solids
    • A23B4/20—Organic compounds; Microorganisms; Enzymes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D275/00—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23B—PRESERVING, e.g. BY CANNING, MEAT, FISH, EGGS, FRUIT, VEGETABLES, EDIBLE SEEDS; CHEMICAL RIPENING OF FRUIT OR VEGETABLES; THE PRESERVED, RIPENED, OR CANNED PRODUCTS
    • A23B4/00—General methods for preserving meat, sausages, fish or fish products
    • A23B4/06—Freezing; Subsequent thawing; Cooling
    • A23B4/08—Freezing; Subsequent thawing; Cooling with addition of chemicals or treatment with chemicals before or during cooling, e.g. in the form of an ice coating or frozen block
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23B—PRESERVING, e.g. BY CANNING, MEAT, FISH, EGGS, FRUIT, VEGETABLES, EDIBLE SEEDS; CHEMICAL RIPENING OF FRUIT OR VEGETABLES; THE PRESERVED, RIPENED, OR CANNED PRODUCTS
    • A23B4/00—General methods for preserving meat, sausages, fish or fish products
    • A23B4/10—Coating with a protective layer; Compositions or apparatus therefor
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23K—FODDER
    • A23K30/00—Processes specially adapted for preservation of materials in order to produce animal feeding-stuffs
    • 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
    • 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
    • A23L3/36—Freezing; Subsequent thawing; Cooling
    • A23L3/37—Freezing; Subsequent thawing; Cooling with addition of or treatment with chemicals

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  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Polymers & Plastics (AREA)
  • Food Science & Technology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Zoology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Wood Science & Technology (AREA)
  • Microbiology (AREA)
  • Health & Medical Sciences (AREA)
  • Nutrition Science (AREA)
  • Animal Husbandry (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Food Preservation Except Freezing, Refrigeration, And Drying (AREA)
  • Fodder In General (AREA)

Description

Oppfinnelsen vedrører et middel for antimikrobiell behandling av næringsmidler som skal dypfryses, f.eks. fisk, kjøtt, reker, fjærkre, såvel som f6rstoffer, særlig tørrf6r av fiske- The invention relates to an agent for antimicrobial treatment of foodstuffs to be deep-frozen, e.g. fish, meat, shrimp, poultry, as well as feed materials, especially dry fish feed

og hvalavfall, rekemel, dyreskrottmel, kjøttf6rmel og blodmel,and whale waste, shrimp meal, animal carcass meal, meat meal and blood meal,

ved hvilket en kvaternær oniumforbindelse, spesielt en kvater-wherein a quaternary onium compound, especially a quaternary

nær ammoniumforbindelse er blandet med minst én ytterligere bestanddel . near ammonium compound is mixed with at least one additional component.

BRD-patent 24 50 660 beskriver en fremgangsmåte for antimikrobiell behandling av bestemte f6rmidler, ved hvilken kvaternære oniumforbindelser blandes med polyalkylenglykoler i vandig løsning resp. dispersjon og ved forhøyet temperatur bringes dis- BRD patent 24 50 660 describes a method for antimicrobial treatment of specific agents, in which quaternary onium compounds are mixed with polyalkylene glycols in aqueous solution or dispersion and at an elevated temperature, dis-

se til anvendelse. Med denne fremgangsmåte kan spesielt tørr-férmel behandles antimikrobielt med tilfredsstillende suksess. see application. With this method, dry yeast flour in particular can be treated antimicrobially with satisfactory success.

Det middel som derved anvendes utmerker seg ved, i sammenligning med andre kjente kjemiske desinfeksjonsmidler og fysikal- The agent used thereby excels in, in comparison with other known chemical disinfectants and physical

ske metoder som dreper kimene, ved en relativ god deponeringsvirkning og lav toksisitet samtidig som de er rimelige i pris. methods that kill the germs, with a relatively good deposition effect and low toxicity, while being reasonable in price.

Riktignok har dets virkningsspektrum mot de forskjellige mikroorganismer vist seg å ikke være så bredt som det var øns-kelig i henblikk på en mest mulig universell anvendbarhet. Admittedly, its spectrum of action against the various microorganisms has proven not to be as broad as was desirable in view of the most possible universal applicability.

Heller ikke deponeringsvirkningen er hittil vært helt ut tilfredsstillende. Dette gjelder fremfor alt for den antimikrobielle behandling av férmidler som ikke er angitt i BRD-patentskrift 24 50 666, såvel som av næringsmidler, spesielt næringsmidler som skal dypfryses. Nettopp her består dog på grunn av det behov som oppstår over hele verden med hensyn til dypfryste næringsmidler såvel som transport av disse over svært lange strekninger, en svært stor fare for éalmonella-angrep. Et slikt angrep kan inntre allerede under forarbeidelsestrinnet eller ved kortvarig temperaturstigning over 0°C under transportfasen. Utvikling av patogene kim, spesielt av salmonella, vil da være innlysende. Daglig fastslås rundt omkring i verden tilfeller av salmonellose med døden til følge. Nor has the deposition effect been entirely satisfactory so far. This applies above all to the antimicrobial treatment of food products that are not specified in BRD patent 24 50 666, as well as of foodstuffs, especially foodstuffs that are to be deep-frozen. Precisely here, however, because of the need that arises all over the world with regard to deep-frozen foodstuffs as well as their transport over very long distances, there is a very great danger of éalmonella attack. Such an attack can already occur during the processing stage or when the temperature rises above 0°C for a short time during the transport phase. Development of pathogenic germs, especially salmonella, will then be obvious. Cases of salmonellosis resulting in death are confirmed daily around the world.

En antimikrobiell behandling av næringsmidler for dypfrysing er derfor foreslått, for å holde varene fri for patogene kim før innfrysingsprosessen. Videre burde det oppnås en viss deponeringsvirkning, slik at ingen patogene kim, særlig salmonella, kan opptre i produktet resp. i opptiningsvannet. Fysikalske An antimicrobial treatment of foodstuffs for deep freezing is therefore proposed, to keep the goods free of pathogenic germs before the freezing process. Furthermore, a certain deposition effect should be achieved, so that no pathogenic germs, especially salmonella, can appear in the product or in the thawing water. Physical

metoder for å drepe kim (varmesterilisering, UV-bestråling)methods to kill germs (heat sterilization, UV irradiation)

lar seg ikke, eller bare i begrenset omfang, anvende. Varmesterilisering er på grunn av produksjonens gang ved fremstillingen av dypfryste varer ikke mulig. De enorme energiomkost-ninger, som ville bringe med seg en hurtig avkjøling til de nød-vendige temperaturer, sammen med faren for at det i mellomtiden ville oppstå fornyet infeksjon av varene, er innlysende. cannot, or only to a limited extent, be used. Heat sterilization is not possible due to the production process in the manufacture of deep-frozen goods. The enormous energy costs, which would bring with it a rapid cooling to the necessary temperatures, together with the danger that renewed infection of the goods would occur in the meantime, are obvious.

En ytterligere ulempe ved det middel som er kjent fra BRD-patent 24 50 666 består i at løsningen resp. dispersjonen for forbedring av løseligheten og effektiviteten ved anvendelsen må oppvarmes. Også dette innskrenker anvendelsesområdet - bort-sett fra det apparative og energinyttige oppbud. A further disadvantage of the agent which is known from BRD patent 24 50 666 is that the solution resp. the dispersion to improve the solubility and efficiency of the application must be heated. This also narrows the area of application - apart from the apparatus and energy-efficient bidding.

Formålet med foreliggende oppfinnelse er derfor å tilveie-bringe et middel hvormed et flertall av f6r- og næringsmidler, spesielt næringsmidler for dypfrysing, kan behandles antimikrobielt og som dessuten utmerker seg ved et svært bredt virkningsspektrum og en forbedret deponeringsvirkning. The purpose of the present invention is therefore to provide an agent with which a majority of food and foodstuffs, especially foodstuffs for deep freezing, can be treated antimicrobially and which is also distinguished by a very broad spectrum of action and an improved deposition effect.

Denne oppgave løses i henhold til oppfinnelsen ved at den ytterligere bestanddel, som skal blandes med den kvaternære oni-umf orbindelse , minst er en isotiazolinon-forbindelse. Slike isotiazolinonforbindelser er i og for seg beskrevet f .eks. i US-patentskrift 3 761 488, men ikke i kombinasjon med kvaternære oniumforbindelser og ikke i sammenheng med det her påtenkte anvendelsesområde. This task is solved according to the invention in that the additional component, which is to be mixed with the quaternary oni-um compound, is at least an isothiazolinone compound. Such isothiazolinone compounds are in and of themselves described, e.g. in US patent 3 761 488, but not in combination with quaternary onium compounds and not in connection with the area of application envisaged here.

Blandingen i henhold til oppfinnelsen utmerker seg ved egenskaper som på grunn av de kjente egenskaper ved enkeltbe-standdelene ikke var å vente og derfor beror på en synergistisk virkning. Således er den antimikrobielle virkning og også virk-ningsspektrumet vesentlig forbedret. Midlet kan derfor anvendes for antimikrobiell behandling av en rekke f6rmidler og fremfor alt for næringsmidler, hvorved det egner seg særlig godt for dypfryste næringsmidler. Ved dette har det vist seg at det med midlet kan oppnås en utmerket deponeringsvirkning over svært lange tidsrom. Dessuten er dets enkle håndtering selv under ugunstige tekniske betingelser fremragende, da dets virksomhet og løselighet allerede er gitt ved normale romtemperaturer, og også allerede noen få grader over 0°C. Det kan her gis avkall på en oppvarmning, slik det var nødvendig med midlet i henhold til BRD-patent 24 50 666. The mixture according to the invention is distinguished by properties which, due to the known properties of the individual components, were not to be expected and are therefore due to a synergistic effect. Thus, the antimicrobial action and also the spectrum of action is significantly improved. The agent can therefore be used for antimicrobial treatment of a number of foodstuffs and above all for foodstuffs, whereby it is particularly suitable for deep-frozen foodstuffs. In this way, it has been shown that an excellent deposition effect can be achieved with the agent over very long periods of time. Moreover, its ease of handling even under adverse technical conditions is outstanding, as its activity and solubility are already given at normal room temperatures, and also already a few degrees above 0°C. Heating can be waived here, as was necessary with the product according to BRD patent 24 50 666.

Intet av de kjemiske desinfeksjonsmidler som befinner segNone of the chemical disinfectants found

på markedet eller de kjente fysikalske metoder for å drepe kim kan fremvise lignende gunstige egenskaper. Enten er de midlet i henhold til oppfinnelsen vesentlig underlegne i toksikologisk eller i prosessteknisk henseende eller sogar hva pris og virk- on the market or the known physical methods of killing germs may exhibit similar beneficial properties. Either the means according to the invention are substantially inferior in toxicological or process engineering terms, or even what the price and effect

ning angår, spesielt deponeringsvirkningen.ning concerns, especially the deposition effect.

Disse fremragende fordeler kunne ikke forventes, da de kvaternære oniumforbindelser ikke har et så bredt antimikrobi- These outstanding advantages could not be expected, as the quaternary onium compounds do not have such a broad antimicrobial

elt virkningsspektrum og en sammenligningsvis så kort deponeringsvirkning. Videre taper de ved nærvær av anionaktive substanser og eggehviteholdige ledsagende stoffer sin kimdrepende virkning. Isotiazolinonforbindelsene mangler hurtig drepevirkning overfor mikroorganismer såsom sopper, bakterier, gjærsopper og alger, elt spectrum of action and a comparatively short deposition effect. Furthermore, in the presence of anionic active substances and accompanying substances containing egg white, they lose their germicidal effect. The isothiazolinone compounds lack rapid killing action against microorganisms such as fungi, bacteria, yeasts and algae,

noe som dog er et vesentlig krav for behandling i vaske-, spyle-, dyppe-, dusje- eller bløteprosesser. which is, however, an essential requirement for treatment in washing, rinsing, dipping, showering or soaking processes.

Særlig egnet har isotiazolinonforbindelser av den i krav 2 angitte generelle formel vist seg å være. Der kan såvel R og R^bety hydrogenatomer, kloratomer, bromatomer eller metylgrupper. Isothiazolinone compounds of the general formula specified in claim 2 have proven to be particularly suitable. There, both R and R^ can mean hydrogen atoms, chlorine atoms, bromine atoms or methyl groups.

Y kan være en alkylgruppe med 3-18 karbonatomer, en cykloheksylgruppe, en eventuelt med en laveremolekylær alkylgruppe eller laveremolekylær alkoksygruppe substituert aralkylgruppe med opp til 10 karbonatomer, en 2- eller 4-klorbenzylgruppe, en 2,4- Y can be an alkyl group with 3-18 carbon atoms, a cyclohexyl group, an aralkyl group with up to 10 carbon atoms optionally substituted with a lower molecular weight alkyl group or lower molecular weight alkoxy group, a 2- or 4-chlorobenzyl group, a 2,4-

eller 3,4-diklorbenzylgruppe, en hydroksymetylgruppe, en eventuelt med klor, laveremolekylære alkylgrupper, en nitrogruppe el- or 3,4-dichlorobenzyl group, a hydroxymethyl group, an optionally with chlorine, lower molecular alkyl groups, a nitro group or

ler karbetoksygruppe substituert fenylrest eller en karbamoksy-alkylgruppe av den generelle formel ler carbethoxy group substituted phenyl radical or a carbamoxy-alkyl group of the general formula

X kan være et oksygenatom eller svovelatom og R2en alkylgruppe med 1-18 karbonatomer, en karbetoksymetylgruppe, en klorfenyl-gruppe, en 2,5- eller 3,4-diklorfenylgruppe eller en 4-nitro-fenylgruppe. X can be an oxygen atom or a sulfur atom and R2 an alkyl group with 1-18 carbon atoms, a carbethoxymethyl group, a chlorophenyl group, a 2,5- or 3,4-dichlorophenyl group or a 4-nitro-phenyl group.

Svært gunstige verdier oppnås med isotiazolinonforbindelser som er isotiazolinforbindelser med sammensetningen 5-klor-2-metyl-4-isotiazolin-3-on og 2-metyl-4-isotiazolin-3-on i vektforholdet 3:1. Den tilhørende grafiske fremstilling av forme-len finnes i krav 4. Molekylvektene til disse isotiazolinforbindelser utgjør ca. 14 8,5 resp. 114. Very favorable values are obtained with isothiazolinone compounds which are isothiazoline compounds with the composition 5-chloro-2-methyl-4-isothiazolin-3-one and 2-methyl-4-isothiazolin-3-one in the weight ratio 3:1. The corresponding graphical representation of the formula can be found in claim 4. The molecular weights of these isothiazoline compounds are approx. 14 8.5 or 114.

Som kvaternære oniumforbindelser kommer slike som har denAs quaternary onium compounds come those that have it

i krav 5 angitte generelle formel på tale, hvorved den kvaternære ammoniumforbindelse med den i krav 6 angitte formel har vist seg å være gunstig, i hvilken substituenten R er n-alkyl med fordelingen 40% C12, 50% C14 og 10% C16. in claim 5 stated general formula in speech, whereby the quaternary ammonium compound with the formula stated in claim 6 has proven to be beneficial, in which the substituent R is n-alkyl with the distribution 40% C12, 50% C14 and 10% C16.

Vektblandingsforholdet mellom den kvaternære oniumforbindelse og isotiazolinonforbindelsen bør ligge i området fra 1:1 til 20:1, fortrinnsvis i området 9:1. The weight mixing ratio between the quaternary onium compound and the isothiazolinone compound should be in the range of 1:1 to 20:1, preferably in the range of 9:1.

Midlet i henhold til oppfinnelsen kan på enkel måte anvendes ved den antimikrobielle behandling. Ved anvendelse for f6r-midler bør det holdes et vektforhold av én del av midlet i henhold til oppfinnelsen til 50-250 deler av f6rmidlet. Når midlet anvendes for næringsmidler, anbefales en vandig løsning i en konsentrasjon av 1:500 til 1:2500, som eksempelvis kan anvendes som vaske-, spyle-, dusje- eller bløtevann i siste produksjonstrinn før dypfrysingsfasen. The agent according to the invention can be used in a simple way in the antimicrobial treatment. When used for feed agents, a weight ratio of one part of the agent according to the invention to 50-250 parts of the feed agent should be maintained. When the agent is used for foodstuffs, an aqueous solution in a concentration of 1:500 to 1:2500 is recommended, which can, for example, be used as washing, rinsing, showering or soaking water in the last production step before the deep-freezing phase.

Fremstillingen av det beskrevne middel foregår ved blanding av den aktuelle isotiazolinonforbindelse med den aktuelle kvaternære ammoniumforbindelse, hvorved førstnevnte hensiktsmessig blandes i sistnevnte. Blandingen skal fortrinnsvis finne sted ved temperaturer mellom 25 og 45°C, forøvrig ved omgivelses-trykk. The preparation of the described agent takes place by mixing the relevant isothiazolinone compound with the relevant quaternary ammonium compound, whereby the former is appropriately mixed with the latter. The mixing should preferably take place at temperatures between 25 and 45°C, otherwise at ambient pressure.

Oppfinnelsen skal beskrives ved følgende eksempler. The invention shall be described by the following examples.

Eksempel 1Example 1

Det ble dannet en blanding med 9 vektdeler av et kvaternært ammoniumsalt med substituentene dimetyl, benzyl og n-alkyl, sistnevnte i fordelingen 40% C12, 50% C14 og 10% C16, og 1 vektdel av en isotiazolinforbindelse i sammensetningen 5-klor-2-metyl-4-isotiazolin-3-on (3) + 2-metyl-4-isotiazolin-3-on (1). Denne blanding ble i forholdet 1:100 satt til en fiskemel- resp. dyremel-råmengde. Råmengdene ble podet med forskjellige salmo-nellastammer (Salmonella Eimsbuttel, S. Livingstone, S. Monte-video) , overhelt med "Tetrathionate enrichment Medium" og inkubert ved 40°C. 24 timer senere ble det over-podet på selektivt medium (S.S. Agar, Wilson&Blair, McConckey) og undersøkt angåen-de salmonellavekst. Noen av forsøksmønstrene ble reinfisert under forsøkets varighet, for å fastslå resistens overfor fornyet salmonellaangrep. A mixture was formed with 9 parts by weight of a quaternary ammonium salt with the substituents dimethyl, benzyl and n-alkyl, the latter in the distribution 40% C12, 50% C14 and 10% C16, and 1 part by weight of an isothiazoline compound in the composition 5-chloro-2 -methyl-4-isothiazolin-3-one (3) + 2-methyl-4-isothiazolin-3-one (1). This mixture was added in a ratio of 1:100 to a fishmeal or animal meal raw quantity. The raw quantities were inoculated with different salmonella strains (Salmonella Eimsbuttel, S. Livingstone, S. Monte video), overwashed with "Tetrathionate enrichment medium" and incubated at 40°C. 24 hours later, it was inoculated onto selective medium (S.S. Agar, Wilson&Blair, McConckey) and examined for salmonella growth. Some of the trial patterns were reinfected during the duration of the trial, to determine resistance to renewed salmonella attack.

Under det første forsøkstidsrom som gikk over 3 måneder, ble det fastslått såvel med som uten reinfeksjon, at det ikke var noe nytt salmonella-angrep, hverken i fiskemelet eller i dyremelet. Mønstrene ble på nytt undersøkt etter 6, 8 og 12 måneder for at man skulle fastslå om det etter denne lagrings-tid igjen kunne isoleres salmonella-stammer som var podet ved begynnelsen. Resultatet var negativt hos alle mønstre. Derved fremkommer at den i dette eksempel anvendte blanding gir en umiddelbar beskyttelse mot salmonella-angrep med en deponeringsvirkning på minst 12 måneder ved handelsvanlig lagring. During the first trial period, which lasted over 3 months, it was determined, both with and without reinfection, that there was no new salmonella attack, neither in the fish meal nor in the animal meal. The samples were re-examined after 6, 8 and 12 months in order to determine whether, after this storage time, salmonella strains that had been inoculated at the beginning could be isolated again. The result was negative for all samples. Thereby it appears that the mixture used in this example provides immediate protection against salmonella attack with a deposition effect of at least 12 months when stored commercially.

Eksempel 2Example 2

Samme blanding som i eksempel 1, i forholdet 1:1000/ble tilsatt vaske-, spyle-, dusje- eller bløtevannet for behandling av næringsmidlet som var beregnet på dypfrysing, hvert tilfelle i det siste produksjonstrinn før dypfrysingsfasen. De deretter sjokkfryste produkter ble lagret i henhold til produsentens for-skrifter og etter opptining underkastet en bakteriologisk test på salmonella-angrep. Hverken etter korte eller etter lengre dypfrysingslagringstider ble det i produktet eller i opptiningsvannet påvist salmonella eller andre patogene kim. Et forsøk, hvor det etter en kortvarig opptiningsperiode til +5°C fulgte en fornyet dypkjølingsperiode, viste etter den endelige opptining av produktet likeledes negativt resultat. The same mixture as in example 1, in a ratio of 1:1000/was added to the washing, rinsing, showering or soaking water for treating the food intended for deep freezing, in each case in the last production step before the deep freezing phase. The then shock-frozen products were stored in accordance with the manufacturer's regulations and, after thawing, submitted to a bacteriological test for salmonella attack. Salmonella or other pathogenic germs were not detected in the product or in the thawing water either after short or longer deep-freeze storage times. An experiment, where after a short thawing period to +5°C followed by a renewed deep cooling period, after the final thawing of the product also showed a negative result.

Eksempel 3Example 3

For å vise den baktericide og fungicide virkning ble det utført en vanlig test ved hvilken effektiviteten til to test-komponenter ble undersøkt. Den ene testkomponent var den blanding som er kjent fra eksemplene 1 og 2, mens den annen, her kalt sammenligningskomponent, var den i BRD-patentskrift 24 50 666 eksempelvis nevnte blanding. Denne blanding ble tilsatt én vektdel av et kvaternært ammoniumsalt med substituentene dimetyl, etyl, benzyl og n-alkyl, sistnevnte i fordelingen 50% C12, 30% C14, 17% C16 og 3% C18, med to vektdeler av en vandig poly-etylenglykoldispersjon, hvorved man fikk et faststoffinnhold på 20 % og en molekylvekt på ca. 600. In order to demonstrate the bactericidal and fungicidal effect, a standard test was carried out in which the effectiveness of two test components was investigated. One test component was the mixture known from examples 1 and 2, while the other, here called the comparison component, was the mixture mentioned in BRD patent 24 50 666, for example. To this mixture was added one part by weight of a quaternary ammonium salt with the substituents dimethyl, ethyl, benzyl and n-alkyl, the latter in the distribution 50% C12, 30% C14, 17% C16 and 3% C18, with two parts by weight of an aqueous polyethylene glycol dispersion , whereby a solids content of 20% and a molecular weight of approx. 600.

Test- og sammenligningskomponenter ble seriefortynnet i "Tripticase" soyabønneekstrakt. De ble så underkastet en 1:100 poding med testbakterier, nemlig 24 timer gamle bakterie-kulturer, og med en soppsporesuspensjon, nemlig 7-14 dager gamle og i 7 ml avionisert vann vaskede soppkulturer. Den baktericide resp. fungicide virkningsverdi ble bestemt visuelt hos bakterier etter 24 timers inkuberingstid ved 37°C og hos sopper etter 48 timers inkuberingstid ved 28-30°C. Det frem-kom verdier, i ppm av de aktive substanser, som er angitt i den etterfølgende tabell. Test and comparison components were serially diluted in "Tripticase" soybean extract. They were then subjected to a 1:100 inoculation with test bacteria, namely 24 hour old bacterial cultures, and with a fungal spore suspension, namely 7-14 day old and in 7 ml deionized water washed fungal cultures. The bactericidal or fungicidal effectiveness value was determined visually in bacteria after 24 hours of incubation at 37°C and in fungi after 48 hours of incubation at 28-30°C. Values emerged, in ppm of the active substances, which are indicated in the following table.

Tabellen viser at virkningsverdiene for testkomponentene i henhold til oppfinnelsen i sammenligning med den fra BRD-patent 24 50 666 kjente sammenligningskomponent, regnet på aktivsubstans, er vesentlig forbedret med hensyn til alle de her nevnte mikroorganismer. The table shows that the effectiveness values for the test components according to the invention in comparison with the comparison component known from BRD patent 24 50 666, calculated on active substance, are significantly improved with regard to all the microorganisms mentioned here.

Claims (13)

1. Middel for antimikrobiell behandling av næringsmidler som spesielt er ment for dypfrysing, f.eks. fisk, kjøtt, reker, fjærkre, såvel som av f6rmidler, særlig tø rrf6r av fiske- og hvalavfall, rekemel, dyreskrottmel, kjøttférmel og blodmel, som er tilblandet en kvaternær. oniumforbindelse, spesielt en kvaternær ammoniumforbindelse, med minst en ytterligere bestanddel, karakterisert ved at den ytterligere bestanddel i det minste er en isotiazolinonforbindelse.1. Means for antimicrobial treatment of foodstuffs which are specially intended for deep freezing, e.g. fish, meat, prawns, poultry, as well as of feedstuffs, especially dried fish and whale waste, prawn meal, animal carcass meal, meat fat meal and blood meal, which has been mixed with a quaternary. onium compound, especially a quaternary ammonium compound, with at least one further component, characterized in that the further component is at least an isothiazolinone compound. 2. Middel som angitt i krav 1, karakterisert ved at isotiazolinonforbindelsen(e) har følgende generelle formel: 2. Agent as specified in claim 1, characterized in that the isothiazolinone compound(s) has the following general formula: 3. Middel som angitt i krav 2, karakterisert ved at såvel R som R^ betyr hydrogenatomer, kloratomer, bromatomer eller metylgrupper, og at Y er en alkylgruppe med 3-18 karbonatomer, en cykloheksylgruppe, en eventuelt med en laveremolekylær alkylgruppe eller laveremolekylær alkoksygruppe substituert aralkylgruppe med opp til 10 karbonatomer, en 2- eller 4-klorbenzylgruppe, en 2,4- eller 3,4-diklorbenzylgruppe, en hydroksymetylgruppe, en eventuelt med klor, laveremolekylære alkylgrup--per, en nitrogruppe eller karbetoksygruppe substituert fenylrest eller en karbamoxyalkylgruppe av den generelle formel 3. Agent as stated in claim 2, characterized in that both R and R^ mean hydrogen atoms, chlorine atoms, bromine atoms or methyl groups, and that Y is an alkyl group with 3-18 carbon atoms, a cyclohexyl group, one optionally with a lower molecular weight alkyl group or lower molecular weight alkoxy group substituted aralkyl group with up to 10 carbon atoms, a 2- or 4-chlorobenzyl group, a 2,4- or 3,4-dichlorobenzyl group, a hydroxymethyl group, an optionally with chlorine, lower molecular alkyl groups, a nitro group or carbethoxy group substituted phenyl residue or a carbamoxyalkyl group of the general formula hvor X er et oksygenatom eller svovelatom og R2 er en alkylgruppe med 1-8 karbonatomer, en karbetoksymetylgruppe, en klor-fenylgruppe, en 2,5- eller 3,4-diklorfenylgruppe eller en 4-nitrofenylgruppe.where X is an oxygen atom or sulfur atom and R 2 is an alkyl group with 1-8 carbon atoms, a carbethoxymethyl group, a chlorophenyl group, a 2,5- or 3,4-dichlorophenyl group or a 4-nitrophenyl group. 4. Middel som angitt i et av kravene 1 til 3, karakterisert ved at isotiazolinonforbindelsen(e) er en isotiazolinforbindelse med sammensetningen 5-klor-2-metyl-4-isotiazolin-4-on og 2-metyl-4-isotiazolin-3-on i vektforholdet 3:1 og har følgende formel: 4. Agent as specified in one of claims 1 to 3, characterized in that the isothiazolinone compound(s) is an isothiazoline compound with the composition 5-chloro-2-methyl-4-isothiazolin-4-one and 2-methyl-4-isothiazolin-3-one in a weight ratio of 3:1 and has the following formula: 5. Middel som angitt i krav 4, karakterisert ved at molekylvekten til isotiazolinforbindelsen(e) er ca. 148,5 resp. 114. 5. Agent as stated in claim 4, characterized in that the molecular weight of the isothiazoline compound(s) is approx. 148.5 or 114. 6. Middel som angitt i et av kravene 1 til 5, karakterisert ved at den kvaternære ammoniumforbindelse har den generelle formel 6. Agent as specified in one of claims 1 to 5, characterized in that the quaternary ammonium compound has the general formula hvor minst én av substituentene R^ til R^ er av høyeremolekylær natur.where at least one of the substituents R^ to R^ is of a higher molecular nature. 7. Middel som angitt i et av kravene 1 til 6, karakterisert ved at den kvaternære oniumforbindelse er en kvaternær ammoniumforbindelse av følgende formel: 7. Agent as specified in one of claims 1 to 6, characterized in that the quaternary onium compound is a quaternary ammonium compound of the following formula: hvor substituenten R er høyeremolekylært n-alkyl.where the substituent R is higher molecular weight n-alkyl. 8. Middel som angitt i krav 7, karakterisert ved at n-alkyl har fordelingen 40% C12, 50% C14 og 10% C16.8. Agent as stated in claim 7, characterized in that n-alkyl has the distribution 40% C12, 50% C14 and 10% C16. 9. Middel som angitt i et av kravene 1 til 8. karakterisert ved at vektblandingsforholdet mellom den kvaternære oniumforbindelse og isotiazolinonforbindelsen 1:1 til 20:1.9. Means as specified in one of claims 1 to 8. characterized in that the weight mixing ratio between the quaternary onium compound and the isothiazolinone compound is 1:1 to 20:1. 10. Middel som angitt i krav 9, karakterisert ved at vektblandingsforholdet ligger i området 9:1.10. Agent as specified in claim 9, characterized in that the weight mixing ratio is in the range of 9:1. 11. Anvendelse av midlet i henhold til et av kravene 1 til 10 for f6rmidler i et vektforhold av 1 del av midlet til 50-250 deler av f6rmidlet.11. Use of the agent according to one of claims 1 to 10 for carriers in a weight ratio of 1 part of the agent to 50-250 parts of the carrier. 12. Anvendelse av midlet i henhold til et av kravene 1 til 10 for næringsmidler i en vandig løsning i en konsentrasjon av 1:500 til 1:2500.12. Use of the agent according to one of claims 1 to 10 for foodstuffs in an aqueous solution in a concentration of 1:500 to 1:2500. 13. Fremgangsmåte for fremstilling av midlet i henhold til et av kravene 1 til 12, karakterisert ved at isotiazolinonforbindelsen blandes med den kvaternære ammo-niumf orbindelse ved temperaturer som ikke overstiger 50°C, fortrinnsvis ligger på 25-45°C, samt ved omgivelsenes trykk.13. Method for producing the agent according to one of claims 1 to 12, characterized in that the isothiazolinone compound is mixed with the quaternary ammonium compound at temperatures that do not exceed 50°C, preferably at 25-45°C, as well as at the ambient Print.
NO841856A 1982-09-10 1984-05-09 AGENT FOR ANTIMICROBIAL TREATMENT OF FOODS, USE OF THE AGENT AND PROCEDURE FOR PREPARING IT NO841856L (en)

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