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
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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 |
|---|---|---|---|
| DE19725017.3 | 1997-06-13 | ||
| DE19725017A DE19725017A1 (en) | 1997-06-13 | 1997-06-13 | Use of 2-mercapto-pyridine-N-oxide |
| 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) |
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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 |