US2684946A - Washing and disinfecting composition - Google Patents
Washing and disinfecting composition Download PDFInfo
- Publication number
- US2684946A US2684946A US115565A US11556549A US2684946A US 2684946 A US2684946 A US 2684946A US 115565 A US115565 A US 115565A US 11556549 A US11556549 A US 11556549A US 2684946 A US2684946 A US 2684946A
- Authority
- US
- United States
- Prior art keywords
- washing
- disinfecting
- weight
- terminal amino
- cooh
- 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
- 239000000203 mixture Substances 0.000 title claims description 33
- 230000000249 desinfective effect Effects 0.000 title claims description 21
- 238000005406 washing Methods 0.000 title description 19
- 150000001875 compounds Chemical class 0.000 claims description 9
- -1 POLYETHYLENE Polymers 0.000 claims description 8
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 3
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 claims description 2
- 239000004698 Polyethylene Substances 0.000 claims description 2
- 229920000768 polyamine Polymers 0.000 claims description 2
- 229920000573 polyethylene Polymers 0.000 claims description 2
- 229960001124 trientine Drugs 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen(.) Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical compound O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 description 12
- 102000009027 Albumins Human genes 0.000 description 7
- 108010088751 Albumins Proteins 0.000 description 7
- 239000000243 solution Substances 0.000 description 6
- 239000000126 substance Substances 0.000 description 5
- 125000003277 amino group Chemical group 0.000 description 4
- 230000000844 anti-bacterial effect Effects 0.000 description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 description 4
- 150000001413 amino acids Chemical class 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 238000005187 foaming Methods 0.000 description 3
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000010411 cooking Methods 0.000 description 2
- 239000000645 desinfectant Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 239000012266 salt solution Substances 0.000 description 2
- 210000002966 serum Anatomy 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 1
- 206010016322 Feeling abnormal Diseases 0.000 description 1
- 102000011782 Keratins Human genes 0.000 description 1
- 108010076876 Keratins Proteins 0.000 description 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
- 235000011941 Tilia x europaea Nutrition 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000007788 roughening Methods 0.000 description 1
- 230000037307 sensitive skin Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
- A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
- A61Q17/005—Antimicrobial preparations
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
- A61Q19/10—Washing or bathing preparations
-
- 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
- C11D1/02—Anionic compounds
- C11D1/04—Carboxylic acids or salts thereof
- C11D1/10—Amino carboxylic acids; Imino carboxylic acids; Fatty acid condensates thereof
-
- 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
- C11D1/02—Anionic compounds
- C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
- C11D1/26—Sulfonic acids or sulfuric acid esters; Salts thereof derived from heterocyclic compounds
-
- 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
Definitions
- This invention relates to novel and particularly advantageous washing and disinfecting compositions.
- the washing and disinfecting compositions according to the invention consist of a mixture, preferably in a weight ratio of about 2:1 to 9:1, of a washing component composed of a salt of an organic or inorganic acid with an amino acid which, in addition to an aliphatic radical containing 10 to 18 carbon atoms, contains at least 2 and preferably 3 or more basic nitrogen atoms, and at least one carboxyl group, and of a disinfecting component composed of a salt of an organic or inorganic acid with an amino acid which in addition to at least 2 aliphatic radicals containing 6 to 10 carbon atoms contains at least 2 preferably 3 or more basic nitrogen atoms and at least one carboxyl group, preferably, octyl di(a1ninoethyl) -octylamino-acetic acid-hydrochloride or di(octyl-a
- washing and disinfecting compositions ac."- cording to the invention may also consist of mixtures containing more than two of the aforesaid components.
- the constituents on which the mixtures according to the invention are based can be produced by various processes, and advantageously, for example, by the process described in German patent application G. 110,055 I-Vc/ 12g of the same applicant dated October 24, 1944.
- Particularly suitable washing components are, for example, compounds of the following formula R.NH.CH2.CH2.NHCHaCI-IaNI-ICHz.COOH.HC1
- R C16H33. or the acetate or lactate of this amino acid.
- the substances which preferably come into consideration as disinfecting components are:
- composition according to the invention constitutes a particularly valuable advance in the development of the art of disinfection.
- Example 1 100 parts of a 30% aqueous solution of a compound corresponding to the formula Ciel-I33.NH.CH2.CH2.NH.CH2.CH2.NH.
- CHaCHaNI-LCI-IaCOOI-IZHCI are mixed with 50 parts of a 30% aqueous solution of a compound corresponding to the formula CBHi'l-NH.CHLCHZ-NELCHZ.CH!'N.CH2.COOH.HC1
- a washing and disinfecting medium which has a very strong bactericidal action and good foaming and cleansing properties.
- the solution produces no precipitate with albumin.
- Example 2 100 parts of the first solution mentioned in Example 1 are mixed with 50 parts of a 30% solution of a compound corresponding to the formula (CaH17.NI-I.CH2.CH2) 2.N.CH2.COOH.CH3.COOH
- Example 3 An aqueous solution is prepared which contains of a compound of the formula 4% of a compound of the formula C1sH33.NI-I.CH2.CH2.NH.CH2.CH2.
- a Washing and disinfecting composition comprising a mixture of 2 to 9 parts by weight of an acid addition salt of a polyethylene polyamine compound selected from the group consisting of diethylene triamine and triethylene tetramine carrying one alkyl substituent containing 12 to 16 carbon atoms on one of the terminal amino groups and 1 to 2 -CH2COOH substituents on the other terminal amino group as a washing component and 1 part by weight of the hydrochloride of diethylene triamine carrying an octyl substituent on each terminal amino group and 1 -CH2COOH substituent on one of the nitrogen atoms thereof as a disinfecting component.
- a polyethylene polyamine compound selected from the group consisting of diethylene triamine and triethylene tetramine carrying one alkyl substituent containing 12 to 16 carbon atoms on one of the terminal amino groups and 1 to 2 -CH2COOH substituents on the other terminal amino group as a washing component and 1 part by weight of the hydrochloride of diethylene triamine carrying an octyl
- a washing and disinfecting composition comprising a mixture of 2 to 9 parts by weight of an acid addition salt of C15H33. (NI-ICHzCI-Iz) 3.NH.CH2COOH and 1 part by weight of the hydrochloride of diethylene triamine carrying an octyl substituent on each terminal amino group and 1 --CH2COOH substituent on one of the nitrogen atoms thereof as a disinfecting component.
- a washing and disinfecting composition comprising a mixture of 2 to 9 parts by weight of C16H33.NH.CH2.CH2.NH.CH2.CH2.
- a washing and disinfecting composition comprising a mixture of 2 to 9 parts by weight of C1sH33 NH.CH2.CH2.NH.CH2.CH2.
- a washing and disinfecting composition comprising a mixture of C12H25.NH.CH2.CH2.NH.CH2.
Description
Patented July 27, 1954 OFFICE WASHING AN D DISINFECTING COMPOSITION Adolf Schmitz, Essen, Germany, assignor to Th. Goldschrnidt, A. G., Essen, Germany No Drawing. Application September 13, 1949, Serial No. 115,565
Claims priority, application Germany October 1, 1948 Claims.
This invention relates to novel and particularly advantageous washing and disinfecting compositions.
All hitherto known and usual compositions employed to disinfect the human skin are attended by a great disadvantage in that their action is greatly impaired by the presence of a1 bumin, a phenomenon which is manifested by precipitation of dissolved albumin.
Since the exciters of disease are generally surrounded by albumin vessels which bind the greater part of the disinfectant employed, the action of such compositions on the exciters is often very questionable. Moreover, the property of the said compositions of becoming bound to albumin has a disadvantageous effect on the human skin since the keratin of the skin also reacts with the disinfecting composition and is thus modified. .reatment of the skin with such compositions therefore, results in the most favourable cases in roughening and cracking of the skin.
The surprising discovery has now been made that it is possible so to influence disinfecting compositions having very great bactericidal activity, by adding other substances, that the reaction with albumin is suppressed while the anti-bacterial activity is maintained. At the same time a further fact was established, which can also be turned to advantage, namely that the substances which must be added for the aforesaid purpose and which achieves the aforesaid effect, are substances having good washing and foaming properties.
According to the invention, it has thus been possible to provide new compositions which constitute both washing and disinfecting agents and are substantially superior to known composi tions of this type. The washing and disinfecting compositions according to the invention consist of a mixture, preferably in a weight ratio of about 2:1 to 9:1, of a washing component composed of a salt of an organic or inorganic acid with an amino acid which, in addition to an aliphatic radical containing 10 to 18 carbon atoms, contains at least 2 and preferably 3 or more basic nitrogen atoms, and at least one carboxyl group, and of a disinfecting component composed of a salt of an organic or inorganic acid with an amino acid which in addition to at least 2 aliphatic radicals containing 6 to 10 carbon atoms contains at least 2 preferably 3 or more basic nitrogen atoms and at least one carboxyl group, preferably, octyl di(a1ninoethyl) -octylamino-acetic acid-hydrochloride or di(octyl-aminoetliyl)-amino-acetic acid-hydrochloride.
The washing and disinfecting compositions ac."- cording to the invention may also consist of mixtures containing more than two of the aforesaid components.
The constituents on which the mixtures according to the invention are based can be produced by various processes, and advantageously, for example, by the process described in German patent application G. 110,055 I-Vc/ 12g of the same applicant dated October 24, 1944. Particularly suitable washing components are, for example, compounds of the following formula R.NH.CH2.CH2.NHCHaCI-IaNI-ICHz.COOH.HC1
wherein R=C16H33. or the acetate or lactate of this amino acid.
The substances which preferably come into consideration as disinfecting components are:
Octyl-di(aminoethyl) -octy1amino-acetic acid-hydrochloride:
CsHmNH. CH2. CH2.NH. CH2. CH2. CH2. 0 0 011.1101
CaHn
Di (octylaminoethyl) -amino-acetic chloride:
( CsHrLNHCHaCHz) 2.N.CH2.COOH.HC1
The said two substances when used alone, are detrimentally effected in their anti-bacterial ac tivity owing to the presence of albumin, but when used in admixture with the above-mentioned washing components, neither precipitation nor deterioration ccurs with albumin. A solution of the two components in a physiological cooking salt solution in such concentration that both gram-positive and gram-negative bacteria are destroyed within 5 minutes by this solution, has exactly the same action as an equivalent solution prepared with undiluted blood serum instead of physiological cooking salt solution. A comparative experiment carried out under the same conditions with known usual disinfecting compositions showed considerable reductions in value in the presence of serum, for
acid-hydrochloride Even persons having a particularly sensitive skin can withstand, without any irritation whatever, washing of the hands several times daily over a period of weeks with the washing and disinfecting compositions according to the invention. The cleansing and foaming action can be regarded as very good, so that even firmly adhering dirt can readily be removed so as to leave all crevices clean. After washing with the compositions according to the invention, a pleasant soft feeling remains on the skin. Finally, the neutral to weakly acid reaction and the complete stability against lime of the compositions according to the invention may also be mentioned as a further advantage.
By reason of the combination of all these favourable properties, the composition according to the invention constitutes a particularly valuable advance in the development of the art of disinfection.
Example 1 100 parts of a 30% aqueous solution of a compound corresponding to the formula Ciel-I33.NH.CH2.CH2.NH.CH2.CH2.NH.
CHaCHaNI-LCI-IaCOOI-IZHCI are mixed with 50 parts of a 30% aqueous solution of a compound corresponding to the formula CBHi'l-NH.CHLCHZ-NELCHZ.CH!'N.CH2.COOH.HC1
Ca u
and diluted with 150 parts of Water.
A washing and disinfecting medium is obtained which has a very strong bactericidal action and good foaming and cleansing properties. The solution produces no precipitate with albumin.
Example 2 100 parts of the first solution mentioned in Example 1 are mixed with 50 parts of a 30% solution of a compound corresponding to the formula (CaH17.NI-I.CH2.CH2) 2.N.CH2.COOH.CH3.COOH
and diluted with water.
Example 3 An aqueous solution is prepared which contains of a compound of the formula 4% of a compound of the formula C1sH33.NI-I.CH2.CH2.NH.CH2.CH2.
N. (CI-IaCOOH) 21-101 1% of a compound of the formula (CaHnNHCHzCI-Iz) 2.N.CH2.COOH.HC1
I claim: 1. A Washing and disinfecting composition comprising a mixture of 2 to 9 parts by weight of an acid addition salt of a polyethylene polyamine compound selected from the group consisting of diethylene triamine and triethylene tetramine carrying one alkyl substituent containing 12 to 16 carbon atoms on one of the terminal amino groups and 1 to 2 -CH2COOH substituents on the other terminal amino group as a washing component and 1 part by weight of the hydrochloride of diethylene triamine carrying an octyl substituent on each terminal amino group and 1 -CH2COOH substituent on one of the nitrogen atoms thereof as a disinfecting component.
2. A washing and disinfecting composition comprising a mixture of 2 to 9 parts by weight of an acid addition salt of C15H33. (NI-ICHzCI-Iz) 3.NH.CH2COOH and 1 part by weight of the hydrochloride of diethylene triamine carrying an octyl substituent on each terminal amino group and 1 --CH2COOH substituent on one of the nitrogen atoms thereof as a disinfecting component.
3. A washing and disinfecting composition comprising a mixture of 2 to 9 parts by weight of C16H33.NH.CH2.CH2.NH.CH2.CH2.
NH.CH2.CH2.NH.CH2.COOH.2HC1
and 1 part by Weight of OBHXLNH.CH2.CH2.NH.CH2.CHZ-N-CH2-COOH-HC] C5511 4. A washing and disinfecting composition comprising a mixture of 2 to 9 parts by weight of C1sH33 NH.CH2.CH2.NH.CH2.CH2.
NI-I.CH2.CH2.NH.CH2.COOH.2HC1
and 1 part by Weight of (CaI-I17.NH.CH2.CH2) 2-N.CHZ.COOH.CI'I3.COOH
5. A washing and disinfecting composition comprising a mixture of C12H25.NH.CH2.CH2.NH.CH2.
CH2.NH.CH2.COOI-I.HC1
CisHss.NH.CH2.CH2.NH.CH2.
CH2.N.(CH2.COOH) 2.HC1
and
(C8Hl7.NH.CH2.CH2) 2N.CH2.COOH.HC1 in a proportion of about 10:4:1 by Weight.
References Cited in the file of this patent UNITED STATES PA.' a NTS Number Name Date 2,246,524 Kyrides June 24, 1941 2,406,902 Rawlins Sept. 3, 1946
Claims (1)
1. A WASHING AND DISINFECTING COMPOSITION COMPRISING A MIXTURE OF 2 TO 9 PARTS BY WEIGHT OF AN ACID ADDITION SALT OF A POLYETHYLENE POLYAMINE COMPOUND SELECTED FROM THE GROUP CONSISTING OF DIETHYLENE TRIAMINE AND TRIETHYLENE TETRAMINE CARRYING ONE ALKYL SUBSTITUENT CONTAINING 12 TO 16 CARBON ATOMS ON ONE OF THE TERMINAL AMINO GROUPS AND 1 TO 2 -CH2COOH SUBSTITUENTS ON THE OTHER TERMINAL AMINO GROUP AS A WASHING COMPONENT AND 1 PART BY WEIGHT OF THE HYDROCHLORIDE OF DIETHYLENE TRIAMINE CARRYING AN OCTYL SUBSTITUENT ON EACH TERMINAL AMINO GROUP AND 1-CH2COOH SUBSTITUENT ON ONE OF THE NITROGEN ATOMS THEREOF AS A DISINFECTING COMPONENT.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE279778X | 1948-10-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2684946A true US2684946A (en) | 1954-07-27 |
Family
ID=6028764
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US115565A Expired - Lifetime US2684946A (en) | 1948-10-01 | 1949-09-13 | Washing and disinfecting composition |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US2684946A (en) |
| BE (1) | BE491172A (en) |
| CH (1) | CH279778A (en) |
| GB (1) | GB684672A (en) |
| NL (1) | NL70378C (en) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2989437A (en) * | 1955-06-08 | 1961-06-20 | Upjohn Co | Anti-inflammatory and anti-bacterial decongestant nasal spray compositions |
| US3039917A (en) * | 1957-08-06 | 1962-06-19 | Schmitz Adolf | Disinfecting and cleansing method |
| US3125486A (en) * | 1964-03-17 | Method for preventing the growth of | ||
| US3235457A (en) * | 1962-12-07 | 1966-02-15 | Gillette Co | Humectant |
| US3431676A (en) * | 1966-04-11 | 1969-03-11 | Leo Addin | Method and composition for the treatment of fruit trees |
| US4224319A (en) * | 1979-07-31 | 1980-09-23 | Ernest Marcadet | Antiseptic composition for topical application to the skin |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2246524A (en) * | 1938-08-10 | 1941-06-24 | Monsanto Chemicals | Germicide |
| US2406902A (en) * | 1942-11-23 | 1946-09-03 | Parke Davis & Co | Soap-like preparations |
-
0
- NL NL70378D patent/NL70378C/xx active
- BE BE491172D patent/BE491172A/xx unknown
-
1949
- 1949-03-29 GB GB8544/49A patent/GB684672A/en not_active Expired
- 1949-07-29 CH CH279778D patent/CH279778A/en unknown
- 1949-09-13 US US115565A patent/US2684946A/en not_active Expired - Lifetime
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2246524A (en) * | 1938-08-10 | 1941-06-24 | Monsanto Chemicals | Germicide |
| US2406902A (en) * | 1942-11-23 | 1946-09-03 | Parke Davis & Co | Soap-like preparations |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3125486A (en) * | 1964-03-17 | Method for preventing the growth of | ||
| US2989437A (en) * | 1955-06-08 | 1961-06-20 | Upjohn Co | Anti-inflammatory and anti-bacterial decongestant nasal spray compositions |
| US3039917A (en) * | 1957-08-06 | 1962-06-19 | Schmitz Adolf | Disinfecting and cleansing method |
| US3235457A (en) * | 1962-12-07 | 1966-02-15 | Gillette Co | Humectant |
| US3431676A (en) * | 1966-04-11 | 1969-03-11 | Leo Addin | Method and composition for the treatment of fruit trees |
| US4224319A (en) * | 1979-07-31 | 1980-09-23 | Ernest Marcadet | Antiseptic composition for topical application to the skin |
Also Published As
| Publication number | Publication date |
|---|---|
| BE491172A (en) | |
| NL70378C (en) | |
| CH279778A (en) | 1951-12-15 |
| GB684672A (en) | 1952-12-24 |
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