US2085318A - Germicidal preparation - Google Patents
Germicidal preparation Download PDFInfo
- Publication number
- US2085318A US2085318A US58141A US5814136A US2085318A US 2085318 A US2085318 A US 2085318A US 58141 A US58141 A US 58141A US 5814136 A US5814136 A US 5814136A US 2085318 A US2085318 A US 2085318A
- Authority
- US
- United States
- Prior art keywords
- germicidal
- phenol
- para
- butyl
- preparation
- 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
- 230000002070 germicidal effect Effects 0.000 title description 27
- 238000002360 preparation method Methods 0.000 title description 18
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 17
- QHPQWRBYOIRBIT-UHFFFAOYSA-N 4-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C=C1 QHPQWRBYOIRBIT-UHFFFAOYSA-N 0.000 description 15
- 230000000844 anti-bacterial effect Effects 0.000 description 10
- 239000000203 mixture Substances 0.000 description 9
- ASLNDVUAZOHADR-UHFFFAOYSA-N 2-butyl-3-methylphenol Chemical group CCCCC1=C(C)C=CC=C1O ASLNDVUAZOHADR-UHFFFAOYSA-N 0.000 description 8
- 125000000217 alkyl group Chemical group 0.000 description 8
- 150000002989 phenols Chemical class 0.000 description 7
- GJYCVCVHRSWLNY-UHFFFAOYSA-N 2-butylphenol Chemical compound CCCCC1=CC=CC=C1O GJYCVCVHRSWLNY-UHFFFAOYSA-N 0.000 description 6
- 239000003899 bactericide agent Substances 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- WJQOZHYUIDYNHM-UHFFFAOYSA-N 2-tert-Butylphenol Chemical compound CC(C)(C)C1=CC=CC=C1O WJQOZHYUIDYNHM-UHFFFAOYSA-N 0.000 description 5
- 239000008135 aqueous vehicle Substances 0.000 description 3
- 239000000470 constituent Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- KUFFULVDNCHOFZ-UHFFFAOYSA-N 2,4-xylenol Chemical compound CC1=CC=C(O)C(C)=C1 KUFFULVDNCHOFZ-UHFFFAOYSA-N 0.000 description 2
- WXNZTHHGJRFXKQ-UHFFFAOYSA-N 4-chlorophenol Chemical compound OC1=CC=C(Cl)C=C1 WXNZTHHGJRFXKQ-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 229930003836 cresol Natural products 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 230000002708 enhancing effect Effects 0.000 description 2
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 2
- 239000000344 soap Substances 0.000 description 2
- ISPYQTSUDJAMAB-UHFFFAOYSA-N 2-chlorophenol Chemical compound OC1=CC=CC=C1Cl ISPYQTSUDJAMAB-UHFFFAOYSA-N 0.000 description 1
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- LTUVMRCQZKTTOM-UHFFFAOYSA-N 3-butyl-2-ethylphenol Chemical group CCCCC1=CC=CC(O)=C1CC LTUVMRCQZKTTOM-UHFFFAOYSA-N 0.000 description 1
- OSDLLIBGSJNGJE-UHFFFAOYSA-N 4-chloro-3,5-dimethylphenol Chemical compound CC1=CC(O)=CC(C)=C1Cl OSDLLIBGSJNGJE-UHFFFAOYSA-N 0.000 description 1
- CFKMVGJGLGKFKI-UHFFFAOYSA-N 4-chloro-m-cresol Chemical compound CC1=CC(O)=CC=C1Cl CFKMVGJGLGKFKI-UHFFFAOYSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 230000003190 augmentative effect Effects 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- -1 butyl cresol Chemical compound 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229960005443 chloroxylenol Drugs 0.000 description 1
- 239000002285 corn oil Substances 0.000 description 1
- 235000005687 corn oil Nutrition 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- 229940100630 metacresol Drugs 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 229940070805 p-chloro-m-cresol Drugs 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- A01N31/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic oxygen or sulfur compounds
- A01N31/08—Oxygen or sulfur directly attached to an aromatic ring system
-
- 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
Definitions
- I may form a bactericidal preparation containing para-tertiary butyl phenol and/or the alkyl substituted derivatives and having uniform bactericidal effectiveness by incorporating the same in dispersed form in an aqueous vehicle.
- These compounds may be dispersed by diluting their alcoholic solutions with water and as these compounds show a germicidal effect at very low concentrations, the amount of alcohol used may be regarded as negligible for all intensive purposes.
- the dispersion of the germicidal agents may also be affected by other means, for example, by small proportions of castor oil soap, corn oil soap or the like.
- the concentration of the butyl-phenol or its alkyl substituted derivatives such as the butyl cresol in the preparation may be varied within wide limits. I have found a concentration of to be satisfactory for general use, although more or less concentrated products may, of course, be prepared.
- the product may be diluted to any desired concentration, for use say to 5% or more and even to as low as about 0.017%.
- the para-tertiary-butyl-phenol is found to have a phenol coefficient of 33.3 with respect to B. typhosus (20 C.), using the F. D. A. technique; and the para-tertiary-butyl-meta-cresol is found to have a phenol coefficient of 38.9 with respect to B.
- the bactericidal efiectiveness of mixtures of bactericides is found to closely approximate the arithmetical means of the substances contained in the mixture, when figured on the basis of the total amount of bactericidal agents present.
- para-tertiary butyl phenol and the alkyl substituted derivatives thereof have a marked effect in augmenting the germicidal effectiveness of other germicidal compounds in admixture therewith.
- a germicidal preparation comprising a tertiary butyl phenol and a phenolic body having germicidal properties.
- a germicidal preparation comprising a bactericide of the class consisting of para-tertiary butyl phenol and its alkyl substituted derivatives, and a phenolic body having germicidal properties.
- a germicidal preparation comprising a bactericide of the class consisting of para-tertiary butyl phenol and its alkyl substituted derivatives, and a phenolic body having germicidal properties in an aqueous vehicle.
- a germicidal preparation comprising paraterti'ary butyl phenol and a halogenated phenol.
- a germicidal preparation comprising para- 1 tertiary butyl phenol and a chloro-phenol.
- a germicidal preparation comprising paratertiary butyl phenol and chloro-cres ol. v 1
- a germicidal preparation comprising paratertiary butyl phenol and chloro-xylenol.
- a germicidal preparation comprising para-
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Wood Science & Technology (AREA)
- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Plant Pathology (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Description
Patented June 29, 1937 UNITED STATES PATENT OFFICE GERMICIDAL PREPARATION Emil Klarmann, Bloomfield, N. 5., assignor to Lehn & Fink Products Corporation, Bloomfield, N. J., a corporation of Delaware No Drawing. Application January 8, 1936, Serial No. 58,141
11 Claims.
employed as constituents of mixed germicidal preparations, in which they are found to be capable of decidedly enhancing the germicidal efficiency thereof.
By operating in accordance with the present invention, I am able to secure a product of enhanced and uniform bactericidal or germicidal activity, readily and uniformly soluble and dispersible in aqueous media in all proportions. Furthermore, I have found that, by combining, in products in accordance with the present invention, tertiary butyl phenol or the alkyl substituted derivatives thereof, particularly phenols and halogenated or alkylated halogenated phenolic compounds, their combined effectiveness is greatly increased beyond that to be expected or normally found in mixtures of bactericidal compounds.
In accordance with the present invention I may form a bactericidal preparation containing para-tertiary butyl phenol and/or the alkyl substituted derivatives and having uniform bactericidal effectiveness by incorporating the same in dispersed form in an aqueous vehicle. These compounds may be dispersed by diluting their alcoholic solutions with water and as these compounds show a germicidal effect at very low concentrations, the amount of alcohol used may be regarded as negligible for all intensive purposes. The dispersion of the germicidal agents may also be affected by other means, for example, by small proportions of castor oil soap, corn oil soap or the like.
The concentration of the butyl-phenol or its alkyl substituted derivatives such as the butyl cresol in the preparation may be varied within wide limits. I have found a concentration of to be satisfactory for general use, although more or less concentrated products may, of course, be prepared. The product may be diluted to any desired concentration, for use say to 5% or more and even to as low as about 0.017%. In such preparations, containing negligible quantities of alcohol, the para-tertiary-butyl-phenol is found to have a phenol coefficient of 33.3 with respect to B. typhosus (20 C.), using the F. D. A. technique; and the para-tertiary-butyl-meta-cresol is found to have a phenol coefficient of 38.9 with respect to B. typhosus under the same conditions. 5 I have also found that in such preparations, para-tertiary butyl phenol or its alkyl-substituted derivatives, in combination with other bactericidal agents of similar character and particularly phenols and alkyl and halogenated phenols. 7
have the peculiar property of enhancing the bactericidal effect of the mixtures. In general and in contradistinction to my discovery, the bactericidal efiectiveness of mixtures of bactericides is found to closely approximate the arithmetical means of the substances contained in the mixture, when figured on the basis of the total amount of bactericidal agents present.
For example, in aqueous dispersions of the germicide made as above described, and in concentrations as indicated below, the following phenol coefficients with respect to B. typhosus are found:
Mixtures of equal parts of bactericides (not including p. tertiary butylphenol or p. tertiary butyl-m-cresol) are in general found to have an effectiveness which closely approaches the calculated arithmetical means of the phenol 00- efficients of these compounds, as disclosed in my prior Patents No. 1,953,413, dated April 3, 1934; and No. 1,984,646, dated December 18, 1934.
However, when these substances are combined in a germicidal preparation with para-tertiary butyl phenol and/or alkyl-substituted para-tertiary butyl phenols, their combined effectiveness is much higher than the arithmetical means of the constituents. Thus, in a series of preparations containing para-tertiary butyl phenol or para-tertiary butyl-meta-cresol and another germicidal compound in an aqueous emulsion as hereinbefore described; that is with equal proportions of the germicides included in the mixture, the following results were secured (with respect to B. typhosus) 2 Phenol coelficieut M111. germ. cone. in percent Gerrnicides in mixture Cab 5 10 15min. Found cu- Inc.
leted p-tert. butyl phenol and p-chloro-m-cresol 122250 1:2500 122750 27.8 21.4 30 p-tert. butyl phenol and p-chlorophenol. 122250 122500 122500 27.8 18.8 48 p-tert. butyl phenol and p-chloro-mxylenol 123500 124000 124000 44.4 33.3 33 p-tert. butyl phenol and m-xylenol 122000 122250 122250 25.0 1.9.2 30 p-tert. butyl-m-cresol and p-chloro-mcresol 1:4500 125000 125000 55.5 24.2 129 p tert. butyl-m-cre- 501 and p-chlorophenol 123500 1:4000 124000 44.4 21.6 106 p-tert. butyl-m-cresol and p-chloro-mxylenol 1:5000 1:6000 126000 66.7 3 6.1 84 p-tert. butyl-m-cresol and m-xylenol 123000 123250 123250 36.1 22.0 63 p-tert. butylm-cresol and p-cresol 122500 122500 122500 27.8 20.7 34 p-tert. butyl-m-cresol andU.S.P.cresol .1:2500 122500 1:2500 27.8 20.8 34
A similar increased effectiveness is found in mixtures of phenol (carbolic acid) and para-tertiary butyl phenol or para-tertiary butyl-m-cresol or other alkyl substituted derivatives of the tertiary butyl phenol.
It is thus apparent that para-tertiary butyl phenol and the alkyl substituted derivatives: thereof have a marked effect in augmenting the germicidal effectiveness of other germicidal compounds in admixture therewith.
A similar enhancement of eiiectiveness is found with other bacteria, such as B. 0012. Mixtures of para-tertiary-butyl-xylenol, para-tertiary butyl ethyl phenol and other alkyl-substituted para-tertiary butyl phenols with other germicides similarly show an enhanced germicidal effectivness. .A similar action may be found in this admixture with otherhalogenated phenols than thosehereinbefore referred to, such as the corresponding bromo and iodo compounds and other halogenated phenol derivatives.
It is readily apparent that various flavoring or perfuming constituents, soluble substances capable of modifying surface tension, bland oils or the like may be introduced into the aqueous vehicle of the germicidal preparation made in accordance with the present invention, in producing commercial products.
Although the present invention has been described in connection with details of specific examples embodying the same, it is not intended that it shall be regarded as limited thereto, except in so far as included in the accompanying claims.
I claim:
1. A germicidal preparation comprising a tertiary butyl phenol and a phenolic body having germicidal properties.
2. A germicidal preparation comprising a bactericide of the class consisting of para-tertiary butyl phenol and its alkyl substituted derivatives, and a phenolic body having germicidal properties.
3. A germicidal preparation comprising a bactericide of the class consisting of para-tertiary butyl phenol and its alkyl substituted derivatives, and a phenolic body having germicidal properties in an aqueous vehicle.
4. A germicidal preparation comprising paraterti'ary butyl phenol and a halogenated phenol.
5. A germicidal preparation comprising para- 1 tertiary butyl phenol and a chloro-phenol.
6. A germicidal preparation comprising paratertiary butyl phenol and chloro-cres ol. v 1
7. A germicidal preparation comprising paratertiary butyl phenol and chloro-xylenol.
8. A germicidal preparation comprising para-
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US58141A US2085318A (en) | 1936-01-08 | 1936-01-08 | Germicidal preparation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US58141A US2085318A (en) | 1936-01-08 | 1936-01-08 | Germicidal preparation |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2085318A true US2085318A (en) | 1937-06-29 |
Family
ID=22014956
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US58141A Expired - Lifetime US2085318A (en) | 1936-01-08 | 1936-01-08 | Germicidal preparation |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2085318A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2572855A (en) * | 1947-11-19 | 1951-10-30 | Koppers Co Inc | Bactericidal compositions |
| US3046190A (en) * | 1956-09-28 | 1962-07-24 | Monsanto Chemicals | Germicides |
-
1936
- 1936-01-08 US US58141A patent/US2085318A/en not_active Expired - Lifetime
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2572855A (en) * | 1947-11-19 | 1951-10-30 | Koppers Co Inc | Bactericidal compositions |
| US3046190A (en) * | 1956-09-28 | 1962-07-24 | Monsanto Chemicals | Germicides |
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