US3686405A - Biocidal preparation - Google Patents
Biocidal preparation Download PDFInfo
- Publication number
- US3686405A US3686405A US10280A US3686405DA US3686405A US 3686405 A US3686405 A US 3686405A US 10280 A US10280 A US 10280A US 3686405D A US3686405D A US 3686405DA US 3686405 A US3686405 A US 3686405A
- Authority
- US
- United States
- Prior art keywords
- formula
- compound
- compounds
- alkyl
- carbon atoms
- 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 - Lifetime
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
- C11D3/485—Halophors, e.g. iodophors
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
-
- 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
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/88—Ampholytes; Electroneutral compounds
- C11D1/90—Betaines
Definitions
- a biocidal preparation comprises a biocidally effective amount of a mixture of a compound of the general formula:
- R is alkyl with eight to 18 carbon atoms or benzyl which is chlorinated or brominated in 2- and/or 4-position and of a compound of the general formula:
- BIOCIDAL PREPARATION CROSS REFERENCE TO PRIOR DISCLOSURE This invention has been disclosed in Disclosure Document 000009 deposited on Apr. 23, 1969.
- the invention relates to biocidal preparations.
- Another object of the invention is to provide a biocidal preparation of the indicated kind which exerts superior biocidal characteristics.
- biocidal preparation of the indicated kind in the form of a clear aqueous solution which can be readily dispensed by automatic dosage devices and which has a biocidal activity which is the same as or even superior to that of the prior art aqueous dispersions.
- biocidal preparations of increased biocidal effect and excellent water solubility can be prepared by admixing the compounds of formula I with certain preselected surface active betaines which in themselves have a rather low bacteriological activity.
- R is alkyl with seven to 17 carbon atoms.
- the compounds of formula I should be admixed with the betaine compounds of formula II in a weight ratio of about2: l to l :5.
- R is alkyl with eight to 18 carbon atoms or benzyl which is chlorinated or brominated in 2- and/or 4-position and compounds of the formula:
- R is alkyl with seven to 17 carbon atoms, the compounds of formula I and formula I] being present in the weight ratio of about 2 l to 1 5.
- the compounds of formula I themselves may be mixtures or compounds with different chain lengths of the alkyl group.
- Such compound mixtures with different alkyl chain lengths are thus, for example, obtained by reacting 2,6-diaminopyridine with an alkylhalide or alkylsulphate derived from natu ral fats or products of the oxosynthesis. This has been elucidated in detail in the copending application referred to. The same applies to the compounds of formula II and the R group contained therein.
- biocidal activity of the compounds of formula I is increased by their admixture with compounds of formula II is certainly unexpected and surprising.
- surface active compounds which are chemically related with compounds of formula I, such as quaternary ammonium compounds and surface active amino acids which have a relatively pronounced bacteriological activity, are in respect to this bacteriological activity negatively affected by the addition of compounds of formula II.
- surface active amines are admixed with compounds of formula I]
- the bactericidal activity of the mixture is considerably less than that of the surface active amine alone.
- the compounds of formula I may be prepared in the manner disclosed in the copending application. Generally, it may be stated that 2,6-diaminopyridine may be reacted with alkylhalide or alkylsulphate or with correspondingly chlorinated or brominated benzylhalide, preferably in the presence of an acid acceptor.
- the compounds of formula ll may be prepared corresponding to the teachings of USA Pat. No. 3,225,074.
- the preparation of the inventive synergistic mixture is effected in simple manner by dissolving the compounds of formula I in aqueous solutions of the compounds of formula II while adding acids, such as HCl, H 80 H PO CH COOH, CH CHOHCOOH and the like so as to obtain a pH-value of 7 or smaller.
- the mixing ratio between the formulal and formula II compounds may vary within wide limits but is advantageously within the range of 2 l to 1 5.
- the inventive mixtures are then obtained in the form of clear weakly colored aqueous solutions whose odor is primarily determined by the acid used, since the odor of the compounds of formula I and II proper is hardly noticeable.
- inventive preparations may thus be in the form of aqueous solutions which, however, may be admixed with additional components such as inorganic compounds, dyestuffs, scenting agents, thickeners and the like.
- additional components such as inorganic compounds, dyestuffs, scenting agents, thickeners and the like.
- inventive preparations in the form of pastes, slurries or solids and to convert the preparations into aqueous solutions only just prior to or during use.
- omooo III pH-value of the 1 percent solution was 4.3.
- protein error indicates the loss of biocidal activity caused by the presence of protein.
- an aqueous solution corresponding to 1 a) above was used whose different dilution stages were admixed with percent of serum from cows or oxen.
- the bactericidal activity is hardly influenced by the addition of the serum:
- a 10 percent solution of the chloroxylenol in a mixture consisting of 1,2-propyleneglycol and an amount of formula II compound was prepared. Said amount was sufficient so that upon dilution with water to a concentration of the formulal compound corresponding to 0.1 percent, a clear aqueous solution was obtained. This aqueous solution was found to be completely ineffective in respect to all 4 test species after a testing period of 30 minutes.
- a bactericidal mixture comprising a compound of the formula:
- R is selected from the group consisting of alkyl of eight to 18 carbon atoms, 2-chlorobenzyl, 4- chlorobenzyl, 2,4-dichlorobenzyl, 2-bromobenzyl, 4- bromobenzyl and 2,4-dibromobenzyl and a compound of the formula 5 wherein R is alkyl of seven to 17 carbon atoms, the weight ratio of said formula I and formula II com pounds being between about 2 l and l 5.
- a substantially clear aqueous bactericidal preparation having a Ph valve of at the most 7 and comprising:
- R is selected from the group consisting of alkyl of 8m 18 carbon atoms, 2-ch1orobenzyl, 4- chlorobenzyl, 2,4-dichlorobenzyl, 2-bromobenzyl, 4- bromobenzyl and 2,4-dibromobenzyl,
- R is selected from the group consisting of alkyl of 8 to 18 carbon atoms, 2-chlorobenzyl, 4- chlorobenzyl, 2,4-dichlorobenzyl, 2-bromobenzyl, 4-
- bromobenzyl and 2,4-dibromo-benzyl and further comprising an amount of a compound of formula:
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Chemistry (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Tyre Moulding (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19691908078 DE1908078B1 (de) | 1969-02-18 | 1969-02-18 | Biocide Zubereitung |
Publications (1)
Publication Number | Publication Date |
---|---|
US3686405A true US3686405A (en) | 1972-08-22 |
Family
ID=5725602
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US10280A Expired - Lifetime US3686405A (en) | 1969-02-18 | 1970-02-10 | Biocidal preparation |
Country Status (12)
Country | Link |
---|---|
US (1) | US3686405A (de) |
AT (1) | AT301035B (de) |
BE (1) | BE746091A (de) |
CH (1) | CH528859A (de) |
DE (1) | DE1908078B1 (de) |
DK (1) | DK122155B (de) |
ES (1) | ES376951A1 (de) |
FR (1) | FR2037098A1 (de) |
GB (1) | GB1256984A (de) |
NL (1) | NL7001829A (de) |
NO (1) | NO129886B (de) |
SE (1) | SE357293B (de) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6054139A (en) * | 1996-05-10 | 2000-04-25 | Diversey Lever Inc. | Cleaning and/or disinfecting composition |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2004077954A1 (en) | 2003-03-05 | 2004-09-16 | Byocoat Enterprises, Inc., | Antimicrobial solution and process |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2080517A (en) * | 1931-11-05 | 1937-05-18 | Pyridium Corp | Medicinal preparations including aminopyridine salts and methods of preparing and utilizing the same |
US2461119A (en) * | 1943-07-31 | 1949-02-08 | Squibb & Sons Inc | Bis-glycolic acid amides of 2, 6-diamino-pyridines and method of preparing them |
DE1062392B (de) * | 1958-05-31 | 1959-07-30 | Goldschmidt Ag Th | Keimtoetende Haarwaschmittel |
US3225074A (en) * | 1959-12-28 | 1965-12-21 | American Cyanamid Co | Betaines |
US3328307A (en) * | 1962-12-14 | 1967-06-27 | Goldschmidt Ag Th | Bubble bath preparation |
-
1969
- 1969-02-18 DE DE19691908078 patent/DE1908078B1/de active Pending
-
1970
- 1970-02-10 US US10280A patent/US3686405A/en not_active Expired - Lifetime
- 1970-02-10 NL NL7001829A patent/NL7001829A/xx unknown
- 1970-02-13 SE SE01854/70A patent/SE357293B/xx unknown
- 1970-02-16 CH CH216970A patent/CH528859A/de not_active IP Right Cessation
- 1970-02-17 NO NO00559/70A patent/NO129886B/no unknown
- 1970-02-17 ES ES376951A patent/ES376951A1/es not_active Expired
- 1970-02-17 FR FR7005534A patent/FR2037098A1/fr not_active Withdrawn
- 1970-02-17 GB GB1256984D patent/GB1256984A/en not_active Expired
- 1970-02-17 DK DK75670AA patent/DK122155B/da unknown
- 1970-02-17 BE BE746091D patent/BE746091A/xx unknown
- 1970-02-18 AT AT146670A patent/AT301035B/de not_active IP Right Cessation
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2080517A (en) * | 1931-11-05 | 1937-05-18 | Pyridium Corp | Medicinal preparations including aminopyridine salts and methods of preparing and utilizing the same |
US2461119A (en) * | 1943-07-31 | 1949-02-08 | Squibb & Sons Inc | Bis-glycolic acid amides of 2, 6-diamino-pyridines and method of preparing them |
DE1062392B (de) * | 1958-05-31 | 1959-07-30 | Goldschmidt Ag Th | Keimtoetende Haarwaschmittel |
US3225074A (en) * | 1959-12-28 | 1965-12-21 | American Cyanamid Co | Betaines |
US3328307A (en) * | 1962-12-14 | 1967-06-27 | Goldschmidt Ag Th | Bubble bath preparation |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6054139A (en) * | 1996-05-10 | 2000-04-25 | Diversey Lever Inc. | Cleaning and/or disinfecting composition |
Also Published As
Publication number | Publication date |
---|---|
FR2037098A1 (de) | 1970-12-31 |
SE357293B (de) | 1973-06-25 |
CH528859A (de) | 1972-10-15 |
BE746091A (fr) | 1970-07-31 |
DE1908078B1 (de) | 1970-08-20 |
GB1256984A (de) | 1971-12-15 |
NL7001829A (de) | 1970-08-20 |
AT301035B (de) | 1972-08-25 |
ES376951A1 (es) | 1972-05-01 |
DK122155B (da) | 1972-01-31 |
NO129886B (de) | 1974-06-10 |
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