CA2578185C - Use of 2-mercapto-pyridine n-oxide - Google Patents
Use of 2-mercapto-pyridine n-oxide Download PDFInfo
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- CA2578185C CA2578185C CA002578185A CA2578185A CA2578185C CA 2578185 C CA2578185 C CA 2578185C CA 002578185 A CA002578185 A CA 002578185A CA 2578185 A CA2578185 A CA 2578185A CA 2578185 C CA2578185 C CA 2578185C
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- oxide
- pyridine
- mercapto
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- YBBJKCMMCRQZMA-UHFFFAOYSA-N pyrithione Chemical compound ON1C=CC=CC1=S YBBJKCMMCRQZMA-UHFFFAOYSA-N 0.000 title claims abstract description 18
- -1 alkaline earth metal salts Chemical class 0.000 claims abstract description 6
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 5
- 150000001340 alkali metals Chemical class 0.000 claims abstract description 5
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims abstract description 5
- 239000000203 mixture Substances 0.000 claims description 29
- 239000004480 active ingredient Substances 0.000 claims description 16
- YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 claims description 6
- NCKMMSIFQUPKCK-UHFFFAOYSA-N 2-benzyl-4-chlorophenol Chemical compound OC1=CC=C(Cl)C=C1CC1=CC=CC=C1 NCKMMSIFQUPKCK-UHFFFAOYSA-N 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- OSDLLIBGSJNGJE-UHFFFAOYSA-N 4-chloro-3,5-dimethylphenol Chemical compound CC1=CC(O)=CC(C)=C1Cl OSDLLIBGSJNGJE-UHFFFAOYSA-N 0.000 claims description 4
- TUBQDCKAWGHZPF-UHFFFAOYSA-N 1,3-benzothiazol-2-ylsulfanylmethyl thiocyanate Chemical compound C1=CC=C2SC(SCSC#N)=NC2=C1 TUBQDCKAWGHZPF-UHFFFAOYSA-N 0.000 claims description 3
- RULKYXXCCZZKDZ-UHFFFAOYSA-N 2,3,4,5-tetrachlorophenol Chemical compound OC1=CC(Cl)=C(Cl)C(Cl)=C1Cl RULKYXXCCZZKDZ-UHFFFAOYSA-N 0.000 claims description 3
- HSQFVBWFPBKHEB-UHFFFAOYSA-N 2,3,4-trichlorophenol Chemical compound OC1=CC=C(Cl)C(Cl)=C1Cl HSQFVBWFPBKHEB-UHFFFAOYSA-N 0.000 claims description 3
- BSWWXRFVMJHFBN-UHFFFAOYSA-N 2,4,6-tribromophenol Chemical compound OC1=C(Br)C=C(Br)C=C1Br BSWWXRFVMJHFBN-UHFFFAOYSA-N 0.000 claims description 3
- IYOLBFFHPZOQGW-UHFFFAOYSA-N 2,4-dichloro-3,5-dimethylphenol Chemical compound CC1=CC(O)=C(Cl)C(C)=C1Cl IYOLBFFHPZOQGW-UHFFFAOYSA-N 0.000 claims description 3
- IQUPABOKLQSFBK-UHFFFAOYSA-N 2-nitrophenol Chemical compound OC1=CC=CC=C1[N+]([O-])=O IQUPABOKLQSFBK-UHFFFAOYSA-N 0.000 claims description 3
- QCDWFXQBSFUVSP-UHFFFAOYSA-N 2-phenoxyethanol Chemical compound OCCOC1=CC=CC=C1 QCDWFXQBSFUVSP-UHFFFAOYSA-N 0.000 claims description 3
- KFZXVMNBUMVKLN-UHFFFAOYSA-N 4-chloro-5-methyl-2-propan-2-ylphenol Chemical compound CC(C)C1=CC(Cl)=C(C)C=C1O KFZXVMNBUMVKLN-UHFFFAOYSA-N 0.000 claims description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 3
- MDNWOSOZYLHTCG-UHFFFAOYSA-N Dichlorophen Chemical compound OC1=CC=C(Cl)C=C1CC1=CC(Cl)=CC=C1O MDNWOSOZYLHTCG-UHFFFAOYSA-N 0.000 claims description 3
- XEFQLINVKFYRCS-UHFFFAOYSA-N Triclosan Chemical compound OC1=CC(Cl)=CC=C1OC1=CC=C(Cl)C=C1Cl XEFQLINVKFYRCS-UHFFFAOYSA-N 0.000 claims description 3
- UBXYXCRCOKCZIT-UHFFFAOYSA-N biphenyl-3-ol Chemical compound OC1=CC=CC(C=2C=CC=CC=2)=C1 UBXYXCRCOKCZIT-UHFFFAOYSA-N 0.000 claims description 3
- YXVFYQXJAXKLAK-UHFFFAOYSA-N biphenyl-4-ol Chemical compound C1=CC(O)=CC=C1C1=CC=CC=C1 YXVFYQXJAXKLAK-UHFFFAOYSA-N 0.000 claims description 3
- 150000004696 coordination complex Chemical class 0.000 claims description 3
- 229960003887 dichlorophen Drugs 0.000 claims description 3
- ANUSOIHIIPAHJV-UHFFFAOYSA-N fenticlor Chemical compound OC1=CC=C(Cl)C=C1SC1=CC(Cl)=CC=C1O ANUSOIHIIPAHJV-UHFFFAOYSA-N 0.000 claims description 3
- 229950005344 fenticlor Drugs 0.000 claims description 3
- JWZXKXIUSSIAMR-UHFFFAOYSA-N methylene bis(thiocyanate) Chemical compound N#CSCSC#N JWZXKXIUSSIAMR-UHFFFAOYSA-N 0.000 claims description 3
- 229960005323 phenoxyethanol Drugs 0.000 claims description 3
- 229960003500 triclosan Drugs 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 2
- VOZSTWKINVCUQY-UHFFFAOYSA-N n-cyclohexyl-1,1-dioxo-1-benzothiophene-2-carboxamide Chemical compound C=1C2=CC=CC=C2S(=O)(=O)C=1C(=O)NC1CCCCC1 VOZSTWKINVCUQY-UHFFFAOYSA-N 0.000 claims description 2
- 239000010985 leather Substances 0.000 abstract description 12
- 241001465754 Metazoa Species 0.000 abstract description 11
- 229910052751 metal Chemical class 0.000 abstract description 5
- 239000002184 metal Chemical class 0.000 abstract description 5
- 238000004321 preservation Methods 0.000 abstract description 3
- LLEMOWNGBBNAJR-UHFFFAOYSA-N biphenyl-2-ol Chemical compound OC1=CC=CC=C1C1=CC=CC=C1 LLEMOWNGBBNAJR-UHFFFAOYSA-N 0.000 description 18
- CFKMVGJGLGKFKI-UHFFFAOYSA-N 4-chloro-m-cresol Chemical compound CC1=CC(O)=CC=C1Cl CFKMVGJGLGKFKI-UHFFFAOYSA-N 0.000 description 12
- 229940070805 p-chloro-m-cresol Drugs 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 235000010292 orthophenyl phenol Nutrition 0.000 description 9
- RPACBEVZENYWOL-XFULWGLBSA-M sodium;(2r)-2-[6-(4-chlorophenoxy)hexyl]oxirane-2-carboxylate Chemical compound [Na+].C=1C=C(Cl)C=CC=1OCCCCCC[C@]1(C(=O)[O-])CO1 RPACBEVZENYWOL-XFULWGLBSA-M 0.000 description 6
- 238000009472 formulation Methods 0.000 description 5
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 4
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 4
- 235000013772 propylene glycol Nutrition 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 241001123663 Penicillium expansum Species 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 150000002989 phenols Chemical class 0.000 description 3
- 241000221832 Amorphotheca resinae Species 0.000 description 2
- 241000228245 Aspergillus niger Species 0.000 description 2
- 241000374462 Aspergillus pseudoglaucus Species 0.000 description 2
- 241000235527 Rhizopus Species 0.000 description 2
- 238000011534 incubation Methods 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 230000000813 microbial effect Effects 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 229920001817 Agar Polymers 0.000 description 1
- 241000079253 Byssochlamys spectabilis Species 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- 241000222290 Cladosporium Species 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-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
- 241000235395 Mucor Species 0.000 description 1
- 241001149951 Mucor mucedo Species 0.000 description 1
- 150000001204 N-oxides Chemical class 0.000 description 1
- 241000228143 Penicillium Species 0.000 description 1
- 241000228153 Penicillium citrinum Species 0.000 description 1
- 240000005384 Rhizopus oryzae Species 0.000 description 1
- 235000013752 Rhizopus oryzae Nutrition 0.000 description 1
- 241000223261 Trichoderma viride Species 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 235000019568 aromas Nutrition 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000003641 microbiacidal effect Effects 0.000 description 1
- 229940124561 microbicide Drugs 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- JPMIIZHYYWMHDT-UHFFFAOYSA-N octhilinone Chemical compound CCCCCCCCN1SC=CC1=O JPMIIZHYYWMHDT-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- FGVVTMRZYROCTH-UHFFFAOYSA-N pyridine-2-thiol N-oxide Chemical class [O-][N+]1=CC=CC=C1S FGVVTMRZYROCTH-UHFFFAOYSA-N 0.000 description 1
- 239000011833 salt mixture Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
Landscapes
- Pyridine Compounds (AREA)
Abstract
'I'he present application relates to the use of 2-mercapto-pyridine N-oxide and/or its alkali metal and alkaline earth metal salts and its metal complexes for the preservation of animal skins and leather.
Description
Use of 2-mercapto-pyridin2 N-oxide This application is a divisional application of copending application 2,293,555, filed June 2, 1998.
The present application relates to the use of 2-mercapto-pyridine N-oxide and/or a metal complex thereof for the preservation of animal skins and leather.
2-Mercapto-pyridine N-oxide and its use as a preservative for cosmetics are l:nown 1O (Microbicides for the Protecting of Materials, Baulens; 1993 Chepi-on &
Hall, pages .294-300).
lt has now surprisingly been found that 2-mercapto-pyridine N-oxide, its salt and metal coinplexes permit excellent and permanent protection of the animal skins and leather from microbial attack during production and storage thereof.
The application therefore relates to the use of 2-mercapto-pyridine N-oxide and/or its salts and/or metal complexes for the preservation of animal skins and leather.
2-Mercapto-pyridine N-oxide is preferably used in combination with at least one further active ingredient suitable for the protection of animal skins and leather. In particular, mercaptobenzothiazole, methylene bisthiocyanate, thiocyanatomethyl-thiobenzothiazole (TCMTB), octylisothiazolinone, N-cyclohexylberizoth.iophene-2-carboxamide s,s-dioxide and preferably phenolic compounds are suitable as further active ingredients for combination with 2-irlercapto-pyridine N-oxide.
These combinations have outstanding and synergistic properties and are likewise the subject of the application.
Suitable phenolic active ingredients are preferably phenol derivatives, suchi as tribromophenol, trichlorophenol, tetrachlorophenol, nitrophenol, 3-methyl-4-chlorophenol, 3,5-dimethyl-4-chlorophenol, phenoxyethanol, dichlorophene, o-phenylphenol, m-phenylphenol, p-phenylphenol, 2-benzyl-4-chlorophenol, 2,4-dichloro-3,5-dimethylphenol, 4-chlorothymol, chlorophene, triclosan, fentichlor and ammonium, alkali metal and alkaline earth metal salts thereof and mixtures thereof.
Preferred 2-mercapto-pyridine N-oxide salts and metal complexes are the sodium aiid potassium salts and copper and zinc complexes.
Le A 32 462-Foreign Coutitries Combinations of 3,5-dimethyl-4-chlorophenol, 2-benzyl-4-chlorophenol; p-chloro-m-cresol (CMC) and/or o-phenylphenol (OPP) as phenolic cotnponents and 2-mercapto-pyridine N-oxide and/or its alkali metal and alkaline earth metal salts and its metal complexes are preferred.
Particularly preferred combinations are the combinations of OPP and/or CMC
with 2-mercapto-pyridine N-oxide and/or with its abovementioned salts and complexes.
In particular, mixtures containing CMC and 2-mercapto-pyridine N-oxide Na salt and optionally OPP and their use according to the invention are preferred.
The mixing ratios of 2-mercapto-pyridine N-oxide are in general 1 part by weight to 5 to 200, preferably 10 to 100, in particular 12 to 50, parts by weight of the further active ingredients or active ingredient mixtures.
The ratio of the further active ingredients, in particular of the phenolic compounds, with one another may be widely varied and can be readily determined by customary experiments. In the case of a mixture of, for example, OPP and CMC, the ratio is preferably 1:1 to 1:5.
The abovenientioned active ingredient and the mixtures of the active ingredients are generally used in the form of formulations. The concentration for use is preferably 0.1 to 1% of active ingredient or active ingredient inixture, relative to the skins or leather to be protected.
The compositions formed during formulation preferably contain 10 to 50% of the active ingredient or of the active ingredient mixture. In general, the compositions contain, as further components, 10 to 30% of alkali metal hydroxides and/or alkaline earth metal hydroxides; I to 20% of ionic and/or nonionic emulsifiers; 5 to 30% of organic solvents, such as, in particular, glycols, ketones, glycol ethers and alcohols, such as ethanol, methanol, 1,2-propanediol, n-propanol or 2-propanol, and 0-0.5% of aromas and fragrances. The remainder to 100% is water.
According to the invention, the active ingredient and the active ingredient mixtures and the compositions which can be prepared therefrom are used according to generally customary methods of use in leather production, for protecting animal skins from attack and damage by microorganisms. Of particular interest is the fact that members of the species Aspergillus niger, Aspergillus repens, Hormoconis resinae, Penicillium glaucum and Trichloderma viride, Penicillium species, such as P.
citrinum or P. glaucum, Paecilomyces variotii, Cladosporium species, such as Mucor species, such as Mucor mucedo, Rhizopus species, such as Rhizopus oryzae, Rhizopus rouxii, are completely and permanently suppressed.
The invention also provides a process for the protection of animal skins and leather from microbial attack, wherein a composition of the invention is added to the animal skins or leather or allowed to act on the animal skins or leather.
The invention also provides use of a composition of the invention for the processing of animal skins.
The invention also provides animal skins, leather and products which are obtained or used in leather production, containing 2-mercapto-pyridine-N-oxide.
In one aspect this divisional application provides a composition comprising 2-mercapto-pyridine N-oxide, a salt thereof, a metal complex thereof or a mixture thereof and at least one further active ingredient selected from the group consisting of the compounds mercaptobenzothiazole, methylene bisthiocyanate, thiocyanatomethylthiobenzothiazole, N-cyclohexylbenzothiophene-2-carboxamide S,S-dioxide, tribromophenol, trichlorophenol, tetrachlorophenol, nitrophenol, 3,5-dimethyl-4-chlorophenol, phenoxyethanol, dichlorophene, m-phenylphenol, p-phenylphenol, 2,4-dichloro-3,5-dimethylphenol, 4-chlorothymol, chlorophene, triclosan, fentichlor and ammonium, an alkali metal or alkaline earth metal salt thereof and a mixture thereof.
The following Examples serve for illustrating the invention and are not limited to this.
Le A 32 462-Foreign Countries Example 1 Agar plates are contaminated with conidia of the species Aspergillus niger, Aspergillus repens, Penicillium glaucum, Trichoderma viride and Hormoconis resinae. Wet chrome leathers treated with mixture I, II and mixture III (wet blue) are then placed on top and incubated for 28 days at 95% relative humidity and to 30 C.
Mixture I Mixture II
30 parts by weight of p-chloro-m-cresol 30 parts by weight of p-chloro-in-cresol 13 parts by weight of o-phenylphenol 13 parts by weight of o-phenylphenol 1.2 parts by weight of 2-mercapto-pyridine N-oxide Na salt Mixture III
37 parts by weight of p-chloro-m-cresol 1.2 parts by weight of 2-mercapto-pyridine N-oxide Na salt The wet blues preserved with the mixture I exhibit growth of mould on the test specimens after an incubation time of only 10 days. In the case of mixture II
and III, no attack is found after an incubation time of 28 days.
Le A 32 462-Foreign Countries Example 2 Formulation I
27 parts by weiglit of p-chloro-m-cresol 12 parts by weight of o-phenylphenol 1.2 parts by weight of 2-inercapto-pyridine N-oxide Na salt 12 parts by weight of NaOH
14.2 parts by weight of 1,2-propanediol Remainder to 100 parts by weight water Formulation II
37 parts by weight of p-chloro-m-cresol 1.2 parts by weight of 2-mercapto-pyridine N-oxide Na salt 10.5 parts by weight of NaOH
14 parts by weight of 1,2-propanediol Remainder to 100 parts by weight water Formulation III
30 parts by weight of p-chloro-m-cresol 1.2 parts by weight of 2-mercapto-pyridine N-oxide Na salt 8.5 parts by weight of NaOH
14 parts by weight of 1,2-propanediol Remainder to 100 parts by weight water
The present application relates to the use of 2-mercapto-pyridine N-oxide and/or a metal complex thereof for the preservation of animal skins and leather.
2-Mercapto-pyridine N-oxide and its use as a preservative for cosmetics are l:nown 1O (Microbicides for the Protecting of Materials, Baulens; 1993 Chepi-on &
Hall, pages .294-300).
lt has now surprisingly been found that 2-mercapto-pyridine N-oxide, its salt and metal coinplexes permit excellent and permanent protection of the animal skins and leather from microbial attack during production and storage thereof.
The application therefore relates to the use of 2-mercapto-pyridine N-oxide and/or its salts and/or metal complexes for the preservation of animal skins and leather.
2-Mercapto-pyridine N-oxide is preferably used in combination with at least one further active ingredient suitable for the protection of animal skins and leather. In particular, mercaptobenzothiazole, methylene bisthiocyanate, thiocyanatomethyl-thiobenzothiazole (TCMTB), octylisothiazolinone, N-cyclohexylberizoth.iophene-2-carboxamide s,s-dioxide and preferably phenolic compounds are suitable as further active ingredients for combination with 2-irlercapto-pyridine N-oxide.
These combinations have outstanding and synergistic properties and are likewise the subject of the application.
Suitable phenolic active ingredients are preferably phenol derivatives, suchi as tribromophenol, trichlorophenol, tetrachlorophenol, nitrophenol, 3-methyl-4-chlorophenol, 3,5-dimethyl-4-chlorophenol, phenoxyethanol, dichlorophene, o-phenylphenol, m-phenylphenol, p-phenylphenol, 2-benzyl-4-chlorophenol, 2,4-dichloro-3,5-dimethylphenol, 4-chlorothymol, chlorophene, triclosan, fentichlor and ammonium, alkali metal and alkaline earth metal salts thereof and mixtures thereof.
Preferred 2-mercapto-pyridine N-oxide salts and metal complexes are the sodium aiid potassium salts and copper and zinc complexes.
Le A 32 462-Foreign Coutitries Combinations of 3,5-dimethyl-4-chlorophenol, 2-benzyl-4-chlorophenol; p-chloro-m-cresol (CMC) and/or o-phenylphenol (OPP) as phenolic cotnponents and 2-mercapto-pyridine N-oxide and/or its alkali metal and alkaline earth metal salts and its metal complexes are preferred.
Particularly preferred combinations are the combinations of OPP and/or CMC
with 2-mercapto-pyridine N-oxide and/or with its abovementioned salts and complexes.
In particular, mixtures containing CMC and 2-mercapto-pyridine N-oxide Na salt and optionally OPP and their use according to the invention are preferred.
The mixing ratios of 2-mercapto-pyridine N-oxide are in general 1 part by weight to 5 to 200, preferably 10 to 100, in particular 12 to 50, parts by weight of the further active ingredients or active ingredient mixtures.
The ratio of the further active ingredients, in particular of the phenolic compounds, with one another may be widely varied and can be readily determined by customary experiments. In the case of a mixture of, for example, OPP and CMC, the ratio is preferably 1:1 to 1:5.
The abovenientioned active ingredient and the mixtures of the active ingredients are generally used in the form of formulations. The concentration for use is preferably 0.1 to 1% of active ingredient or active ingredient inixture, relative to the skins or leather to be protected.
The compositions formed during formulation preferably contain 10 to 50% of the active ingredient or of the active ingredient mixture. In general, the compositions contain, as further components, 10 to 30% of alkali metal hydroxides and/or alkaline earth metal hydroxides; I to 20% of ionic and/or nonionic emulsifiers; 5 to 30% of organic solvents, such as, in particular, glycols, ketones, glycol ethers and alcohols, such as ethanol, methanol, 1,2-propanediol, n-propanol or 2-propanol, and 0-0.5% of aromas and fragrances. The remainder to 100% is water.
According to the invention, the active ingredient and the active ingredient mixtures and the compositions which can be prepared therefrom are used according to generally customary methods of use in leather production, for protecting animal skins from attack and damage by microorganisms. Of particular interest is the fact that members of the species Aspergillus niger, Aspergillus repens, Hormoconis resinae, Penicillium glaucum and Trichloderma viride, Penicillium species, such as P.
citrinum or P. glaucum, Paecilomyces variotii, Cladosporium species, such as Mucor species, such as Mucor mucedo, Rhizopus species, such as Rhizopus oryzae, Rhizopus rouxii, are completely and permanently suppressed.
The invention also provides a process for the protection of animal skins and leather from microbial attack, wherein a composition of the invention is added to the animal skins or leather or allowed to act on the animal skins or leather.
The invention also provides use of a composition of the invention for the processing of animal skins.
The invention also provides animal skins, leather and products which are obtained or used in leather production, containing 2-mercapto-pyridine-N-oxide.
In one aspect this divisional application provides a composition comprising 2-mercapto-pyridine N-oxide, a salt thereof, a metal complex thereof or a mixture thereof and at least one further active ingredient selected from the group consisting of the compounds mercaptobenzothiazole, methylene bisthiocyanate, thiocyanatomethylthiobenzothiazole, N-cyclohexylbenzothiophene-2-carboxamide S,S-dioxide, tribromophenol, trichlorophenol, tetrachlorophenol, nitrophenol, 3,5-dimethyl-4-chlorophenol, phenoxyethanol, dichlorophene, m-phenylphenol, p-phenylphenol, 2,4-dichloro-3,5-dimethylphenol, 4-chlorothymol, chlorophene, triclosan, fentichlor and ammonium, an alkali metal or alkaline earth metal salt thereof and a mixture thereof.
The following Examples serve for illustrating the invention and are not limited to this.
Le A 32 462-Foreign Countries Example 1 Agar plates are contaminated with conidia of the species Aspergillus niger, Aspergillus repens, Penicillium glaucum, Trichoderma viride and Hormoconis resinae. Wet chrome leathers treated with mixture I, II and mixture III (wet blue) are then placed on top and incubated for 28 days at 95% relative humidity and to 30 C.
Mixture I Mixture II
30 parts by weight of p-chloro-m-cresol 30 parts by weight of p-chloro-in-cresol 13 parts by weight of o-phenylphenol 13 parts by weight of o-phenylphenol 1.2 parts by weight of 2-mercapto-pyridine N-oxide Na salt Mixture III
37 parts by weight of p-chloro-m-cresol 1.2 parts by weight of 2-mercapto-pyridine N-oxide Na salt The wet blues preserved with the mixture I exhibit growth of mould on the test specimens after an incubation time of only 10 days. In the case of mixture II
and III, no attack is found after an incubation time of 28 days.
Le A 32 462-Foreign Countries Example 2 Formulation I
27 parts by weiglit of p-chloro-m-cresol 12 parts by weight of o-phenylphenol 1.2 parts by weight of 2-inercapto-pyridine N-oxide Na salt 12 parts by weight of NaOH
14.2 parts by weight of 1,2-propanediol Remainder to 100 parts by weight water Formulation II
37 parts by weight of p-chloro-m-cresol 1.2 parts by weight of 2-mercapto-pyridine N-oxide Na salt 10.5 parts by weight of NaOH
14 parts by weight of 1,2-propanediol Remainder to 100 parts by weight water Formulation III
30 parts by weight of p-chloro-m-cresol 1.2 parts by weight of 2-mercapto-pyridine N-oxide Na salt 8.5 parts by weight of NaOH
14 parts by weight of 1,2-propanediol Remainder to 100 parts by weight water
Claims
1. A composition comprising 2-mercapto-pyridine N-oxide, a salt thereof, a metal complex thereof or a mixture thereof and at least one further active ingredient selected from the group\consisting of the compounds mercaptobenzothiazole, methylene bisthiocyanate, thiocyanatomethylthiobenzothiazole, N-cyclohexylbenzothiophene-2-carboxamide S,S-dioxide, tribromophenol, trichlorophenol, tetrachlorophenol, nitrophenol, 3,5-dimethyl-4-chlorophenol, phenoxyethanol, dichlorophene, m-phenylphenol, p-phenylphenol, 2,4-dichloro-3,5-dimethylphenol, 4-chlorothymol, chlorophene, triclosan, fentichlor and ammonium, an alkali metal or alkaline earth metal salt thereof and a mixture thereof.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA2661724A CA2661724C (en) | 1997-06-13 | 1998-06-02 | Use of 2-mercapto-pyridine n-oxide |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19725017A DE19725017A1 (en) | 1997-06-13 | 1997-06-13 | Use of 2-mercapto-pyridine-N-oxide |
| DE19725017.3 | 1997-06-13 | ||
| CA002293555A CA2293555C (en) | 1997-06-13 | 1998-06-02 | Use of 2-mercapto-pyridine-n-oxide |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002293555A Division CA2293555C (en) | 1997-06-13 | 1998-06-02 | Use of 2-mercapto-pyridine-n-oxide |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2661724A Division CA2661724C (en) | 1997-06-13 | 1998-06-02 | Use of 2-mercapto-pyridine n-oxide |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2578185A1 CA2578185A1 (en) | 1998-12-17 |
| CA2578185C true CA2578185C (en) | 2009-07-28 |
Family
ID=38051277
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002578185A Expired - Fee Related CA2578185C (en) | 1997-06-13 | 1998-06-02 | Use of 2-mercapto-pyridine n-oxide |
Country Status (1)
| Country | Link |
|---|---|
| CA (1) | CA2578185C (en) |
-
1998
- 1998-06-02 CA CA002578185A patent/CA2578185C/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| CA2578185A1 (en) | 1998-12-17 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |
Effective date: 20150602 |