CA1106277A - Microbiocidal agents on the basis of alkyl- diguanidinium salts - Google Patents
Microbiocidal agents on the basis of alkyl- diguanidinium saltsInfo
- Publication number
- CA1106277A CA1106277A CA322,554A CA322554A CA1106277A CA 1106277 A CA1106277 A CA 1106277A CA 322554 A CA322554 A CA 322554A CA 1106277 A CA1106277 A CA 1106277A
- Authority
- CA
- Canada
- Prior art keywords
- alkyl
- weight
- water
- parts
- range
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/48—Medical, disinfecting agents, disinfecting, antibacterial, germicidal or antimicrobial compositions
-
- 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/40—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having a double or triple bond to nitrogen, e.g. cyanates, cyanamides
- A01N47/42—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having a double or triple bond to nitrogen, e.g. cyanates, cyanamides containing —N=CX2 groups, e.g. isothiourea
- A01N47/44—Guanidine; Derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
Abstract
Abstract of the Disclosure:
A microbiocidal agent consisting of 10 to 40 parts by weight of the salt of an alkyl-diguanidine of the for-mula I
in which R is C8-C18 alkyl and m is an integer of from 2 to 6 and 10 to 40 parts by weight of a block polymer of the formula
A microbiocidal agent consisting of 10 to 40 parts by weight of the salt of an alkyl-diguanidine of the for-mula I
in which R is C8-C18 alkyl and m is an integer of from 2 to 6 and 10 to 40 parts by weight of a block polymer of the formula
Description
6Z7'7
- 2 - HOE 7~/F 042 It is known that alkyl-diguanidinium salts have a good bactericidal and fungicidal effect (DE-PS 1,249,457).
Owing to their partially unsatisfactory solubi~ity in water and their poor compatibility, especially with hard water or water containing sodium chloride, their possibi-lities of application are, however, limited.
To improve the solubility and stability in water containing sodium chloride or in hard water it has been proposed to combine the aforesaid salts witn quaternary ammonium compounds or phosphonium compounds or with long chain alkyl diamine salts. It is, however, disadvanta-geous that the said emulsifiers have a negative effect on the microbiocidal activity of the alkyl-diguanidinium salts.
It has now been found that combinations of the salts of alkyl-diguanidines with polyoxethylene-polyoxpropylene block polymers yield stable formulations with improved microbiocidal effect.
It is, therefore, the object of the present inven-tion to provide microbiocidal agents consisting of 10 to40, preferably 20 to 30, parts by weight of the salt of an alkyl-diguanidine of the formula I
R H
H2N-cl-N-(cH2)m-N-c-NH2 (I) NH NH
in which R is C&-C1~ alkyl and m is an integer of from 2 to ~ and 10 to 40 preferably 20 to 30, parts by weight of a block polymer of the formula HO-(CH2-ch2-) 2- ( Ch -c~;2 - ) b-(C~2-~;20)c-~
;27 ~
Owing to their partially unsatisfactory solubi~ity in water and their poor compatibility, especially with hard water or water containing sodium chloride, their possibi-lities of application are, however, limited.
To improve the solubility and stability in water containing sodium chloride or in hard water it has been proposed to combine the aforesaid salts witn quaternary ammonium compounds or phosphonium compounds or with long chain alkyl diamine salts. It is, however, disadvanta-geous that the said emulsifiers have a negative effect on the microbiocidal activity of the alkyl-diguanidinium salts.
It has now been found that combinations of the salts of alkyl-diguanidines with polyoxethylene-polyoxpropylene block polymers yield stable formulations with improved microbiocidal effect.
It is, therefore, the object of the present inven-tion to provide microbiocidal agents consisting of 10 to40, preferably 20 to 30, parts by weight of the salt of an alkyl-diguanidine of the formula I
R H
H2N-cl-N-(cH2)m-N-c-NH2 (I) NH NH
in which R is C&-C1~ alkyl and m is an integer of from 2 to ~ and 10 to 40 preferably 20 to 30, parts by weight of a block polymer of the formula HO-(CH2-ch2-) 2- ( Ch -c~;2 - ) b-(C~2-~;20)c-~
;27 ~
- 3 - HoE_78/F 042 in which a, b and c denote integers which are chosen in such a manner that the block polymer has a molecular weight in the range of from 1,000 to 16,000 and the proportion by weight of the polyoxethylene chains in the total molecule is in the range of from 10 to 90 %, the balance being water and/or a short chain, water-soluble a]cohol, preferably isopropanol.
The alkyl-diguanidines to be used according to the invention can be prepared by known processes, for example by reacting diamines of the formula ~ - NH - (CH2)m - NH2 in which R and m have the aforesaid meaning, with cyan-amide or S-alkyl-isothiourea.
For salt formation mono- and polybasic inorganic or organic acids can be used, for example sulfuric acid, nitric acid, phosphoric acid, hydrochloric acid, formic acid, acetic acid and, above all, high molecular weight aliphatic carboxylic acids such as lauric acid, stearic acid, oleic acid and the like, and mixtures of the said ; acids. Instead of uniform salts there can also be used mixtures thereof, optionally in admixture with other microbiocides.
The microbiocidal agents of the invention, which are prepared by simply mixing the specified components, are distinguished by a good solubility in water and are well compatible with hard water and water containing sodium chloride. Moreover, it is worth mentioning 'hat they have an improved microbiocidal effect compared with the hither-.
. '. - ,: ' ', ' ', ~ ' ' ,:: '' ' ' . ' ' ~ ' ~",' 11~6Z~7
The alkyl-diguanidines to be used according to the invention can be prepared by known processes, for example by reacting diamines of the formula ~ - NH - (CH2)m - NH2 in which R and m have the aforesaid meaning, with cyan-amide or S-alkyl-isothiourea.
For salt formation mono- and polybasic inorganic or organic acids can be used, for example sulfuric acid, nitric acid, phosphoric acid, hydrochloric acid, formic acid, acetic acid and, above all, high molecular weight aliphatic carboxylic acids such as lauric acid, stearic acid, oleic acid and the like, and mixtures of the said ; acids. Instead of uniform salts there can also be used mixtures thereof, optionally in admixture with other microbiocides.
The microbiocidal agents of the invention, which are prepared by simply mixing the specified components, are distinguished by a good solubility in water and are well compatible with hard water and water containing sodium chloride. Moreover, it is worth mentioning 'hat they have an improved microbiocidal effect compared with the hither-.
. '. - ,: ' ', ' ', ~ ' ' ,:: '' ' ' . ' ' ~ ' ~",' 11~6Z~7
- 4 - HOE 78/F 042 -to known formulations with quaternary ammoniur, compounds.
The following example illus,trates the-invention.
E X A M P L E
The following components are mixed:
25 parts of laurylpropylene-diaminoguanidinium mono-lactate 25 parts of polyoxethylene-polyoxpropylene block po-lymer having a total molecular weight of 8,000 and a molecular weight of the polyox-ethylene proportion of 6,300 30 parts of isopropanol 20 parts of water.
The formulation obtained is stable under the condi-tions of the rocking test. It can be further diluted wi~h water in any desired proportion to give a limpid solution.
The microbiocidal effect in ~ /ml was tested by the 555-test of Fytopharmacie at Wageningen/Netherlands. In this test the minimum concentration in ~/ml necessary to reduce 107 germs per milliliter by 105 germs per milliliter is ascertained, the time of contact being 5 minutes.
As comparative agent a commercial formulation consist-ing of the following components 25 parts of laurylpropylene-diamine guanidinium lac-tate 25 parts of soya trimethyl ammonium chloride 50 parts af sclvent and water was used.
.
' ~1~6277
The following example illus,trates the-invention.
E X A M P L E
The following components are mixed:
25 parts of laurylpropylene-diaminoguanidinium mono-lactate 25 parts of polyoxethylene-polyoxpropylene block po-lymer having a total molecular weight of 8,000 and a molecular weight of the polyox-ethylene proportion of 6,300 30 parts of isopropanol 20 parts of water.
The formulation obtained is stable under the condi-tions of the rocking test. It can be further diluted wi~h water in any desired proportion to give a limpid solution.
The microbiocidal effect in ~ /ml was tested by the 555-test of Fytopharmacie at Wageningen/Netherlands. In this test the minimum concentration in ~/ml necessary to reduce 107 germs per milliliter by 105 germs per milliliter is ascertained, the time of contact being 5 minutes.
As comparative agent a commercial formulation consist-ing of the following components 25 parts of laurylpropylene-diamine guanidinium lac-tate 25 parts of soya trimethyl ammonium chloride 50 parts af sclvent and water was used.
.
' ~1~6277
- 5 - HOE 'j8/F 042 Determination of the bactericidial and fungicidial effect time of contact 5 minutes minimum concentration for the reduction by 105 germs/ml type of germ comparative product according to Example of invention Salm. Typh. 2500 ~/ml 250 ~/ml Ps. aerug. about 3000 ~/ml 250 ~ /ml Strept. Faec. 1500 ~/ml 500 ~ /ml 10 5taph. aureus. 2000 ~ /ml 500 ~ /ml Cand. alb. 3000 ~ /ml 250 ~ /ml The table reveals that the mixture according to the invention has an improved microbiocidal effect as compared to the commercial product.
15 In order to reduce the number of germs by 105 germs per milliliter with a time of contact of 5 minutes a much lower concentration of the formulation of the invention is required.
-' " ' ~ :'
15 In order to reduce the number of germs by 105 germs per milliliter with a time of contact of 5 minutes a much lower concentration of the formulation of the invention is required.
-' " ' ~ :'
Claims
What is claimed is:
A microbiocidal agent consisting of 10 to 40 parts by weight of the salt of an alkyl-diguanidinium of the for-mula I
(I) in which R is C8-C18 alkyl and m is an integer of from 2 to 6 and 10 to 40 parts by weight of a block polymer of the formula (II) in which a, b and c denote integers which are chosen in such a manner that the block polymer has a molecular weight in the range of from 1,000 to 16,000 and the proportion by weight of the polyoxethylene chains in the total molecule is in the range of from 10 to 90 %, the balance being water and/or a short chain, water-soluble alcohol.
A microbiocidal agent consisting of 10 to 40 parts by weight of the salt of an alkyl-diguanidinium of the for-mula I
(I) in which R is C8-C18 alkyl and m is an integer of from 2 to 6 and 10 to 40 parts by weight of a block polymer of the formula (II) in which a, b and c denote integers which are chosen in such a manner that the block polymer has a molecular weight in the range of from 1,000 to 16,000 and the proportion by weight of the polyoxethylene chains in the total molecule is in the range of from 10 to 90 %, the balance being water and/or a short chain, water-soluble alcohol.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP2808865.5 | 1978-03-02 | ||
| DE2808865A DE2808865A1 (en) | 1978-03-02 | 1978-03-02 | MICROBIOCIDES BASED ON ALKYL DI GUANIDINIUM SALT |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1106277A true CA1106277A (en) | 1981-08-04 |
Family
ID=6033281
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA322,554A Expired CA1106277A (en) | 1978-03-02 | 1979-03-01 | Microbiocidal agents on the basis of alkyl- diguanidinium salts |
Country Status (6)
| Country | Link |
|---|---|
| EP (1) | EP0003999A3 (en) |
| JP (1) | JPS54132222A (en) |
| AT (1) | AT360180B (en) |
| BR (1) | BR7901266A (en) |
| CA (1) | CA1106277A (en) |
| DE (1) | DE2808865A1 (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4920151A (en) * | 1985-09-03 | 1990-04-24 | Hoechst Aktiengesellschaft | Microbicidal agents based on alkyl-di-guanidinium salts |
| US5811088A (en) * | 1987-02-20 | 1998-09-22 | Emory University | Antiinfective compounds and methods of use |
| CN108689888A (en) * | 2018-05-16 | 2018-10-23 | 中国日用化学研究院有限公司 | A kind of two guanidine salt of alkyl and preparation method thereof |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4456543A (en) * | 1982-06-17 | 1984-06-26 | The Buckeye Cellulose Corporation | Bisbiguanide based antibacterial cleansing products |
| JPS60178801A (en) * | 1984-02-24 | 1985-09-12 | Dainippon Ink & Chem Inc | Guanidine fungicide for agriculture and horticulture |
| US5648071A (en) * | 1986-05-15 | 1997-07-15 | Emory University | Method of treating tumors |
| AT386777B (en) * | 1986-06-03 | 1988-10-10 | Stangl Kurt Dipl Ing | Manipulator for attaching a pouring pipe to the pouring spout of a pouring ladle |
| US5674911A (en) * | 1987-02-20 | 1997-10-07 | Cytrx Corporation | Antiinfective polyoxypropylene/polyoxyethylene copolymers and methods of use |
| HUT67762A (en) | 1991-03-19 | 1995-04-28 | Cytrx Corp | Polyoxypropylene/polyoxiethylene copolymers with improved biological activity and process for producing thereof |
| US6933286B2 (en) | 1991-03-19 | 2005-08-23 | R. Martin Emanuele | Therapeutic delivery compositions and methods of use thereof |
| US7202225B1 (en) | 1993-10-15 | 2007-04-10 | Emanuele R Martin | Therapeutic delivery compositions and methods of use thereof |
| US5622649A (en) | 1991-06-27 | 1997-04-22 | Emory University | Multiple emulsions and methods of preparation |
| WO1995015182A1 (en) * | 1993-12-02 | 1995-06-08 | Emory University | Antiinfective compositions and methods of use |
| AT404087B (en) * | 1997-03-21 | 1998-08-25 | P O C Oil Industry Technology | ADDITIVE AND METHOD FOR STABILIZING LIQUID HYDROCARBON FUELS AGAINST BIODEGRADATION |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL6709022A (en) * | 1966-07-01 | 1968-01-02 | ||
| USB724600I5 (en) * | 1968-04-26 | |||
| GB1338003A (en) * | 1971-06-18 | 1973-11-21 | Ici Ltd | Cleaning compositions |
| DE2330481A1 (en) * | 1973-06-15 | 1975-01-09 | Benckiser Gmbh Joh A | DISH AND RINSE AGENT FOR DISHES AND THE LIKE |
| JPS52136916A (en) * | 1976-05-10 | 1977-11-16 | Dainippon Ink & Chem Inc | Stable mixing of pesticide preparations |
-
1978
- 1978-03-02 DE DE2808865A patent/DE2808865A1/en not_active Withdrawn
-
1979
- 1979-02-22 EP EP79100525A patent/EP0003999A3/en not_active Withdrawn
- 1979-02-27 AT AT148579A patent/AT360180B/en not_active IP Right Cessation
- 1979-03-01 CA CA322,554A patent/CA1106277A/en not_active Expired
- 1979-03-01 JP JP2261679A patent/JPS54132222A/en active Pending
- 1979-03-01 BR BR7901266A patent/BR7901266A/en unknown
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4920151A (en) * | 1985-09-03 | 1990-04-24 | Hoechst Aktiengesellschaft | Microbicidal agents based on alkyl-di-guanidinium salts |
| US5811088A (en) * | 1987-02-20 | 1998-09-22 | Emory University | Antiinfective compounds and methods of use |
| CN108689888A (en) * | 2018-05-16 | 2018-10-23 | 中国日用化学研究院有限公司 | A kind of two guanidine salt of alkyl and preparation method thereof |
| CN108689888B (en) * | 2018-05-16 | 2021-06-04 | 中国日用化学研究院有限公司 | Alkyl biguanide salt and preparation method thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS54132222A (en) | 1979-10-15 |
| EP0003999A2 (en) | 1979-09-19 |
| BR7901266A (en) | 1979-10-09 |
| ATA148579A (en) | 1980-05-15 |
| DE2808865A1 (en) | 1979-09-13 |
| AT360180B (en) | 1980-12-29 |
| EP0003999A3 (en) | 1979-10-17 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |