US2713036A - Antiseptic soap composition - Google Patents
Antiseptic soap composition Download PDFInfo
- Publication number
- US2713036A US2713036A US382831A US38283153A US2713036A US 2713036 A US2713036 A US 2713036A US 382831 A US382831 A US 382831A US 38283153 A US38283153 A US 38283153A US 2713036 A US2713036 A US 2713036A
- Authority
- US
- United States
- Prior art keywords
- detergent
- soap
- xylenol
- antiseptic
- bis
- 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 11
- 239000004599 antimicrobial Substances 0.000 title 1
- 239000003599 detergent Substances 0.000 claims description 14
- 239000000344 soap Substances 0.000 claims description 11
- 150000001875 compounds Chemical class 0.000 claims description 8
- 230000002421 anti-septic effect Effects 0.000 claims description 4
- -1 5-nitro- 2-hydroxy-phenyl Chemical group 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- WXNZTHHGJRFXKQ-UHFFFAOYSA-N 4-chlorophenol Chemical compound OC1=CC=C(Cl)C=C1 WXNZTHHGJRFXKQ-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 239000006916 nutrient agar Substances 0.000 description 2
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Inorganic materials [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- NXXYKOUNUYWIHA-UHFFFAOYSA-N 2,6-di-methyl phenol Natural products CC1=CC=CC(C)=C1O NXXYKOUNUYWIHA-UHFFFAOYSA-N 0.000 description 1
- PJNPZIYGODMAQE-UHFFFAOYSA-N 2-(chloromethyl)-4-nitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1CCl PJNPZIYGODMAQE-UHFFFAOYSA-N 0.000 description 1
- IQHSSYROJYPFDV-UHFFFAOYSA-N 2-bromo-1,3-dichloro-5-(trifluoromethyl)benzene Chemical group FC(F)(F)C1=CC(Cl)=C(Br)C(Cl)=C1 IQHSSYROJYPFDV-UHFFFAOYSA-N 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 241000295644 Staphylococcaceae Species 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 150000001339 alkali metal compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/13—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by hydroxy groups
- C07C205/26—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by hydroxy groups and being further substituted by halogen atoms
Definitions
- This invention relates to new and useful compositions of matter. More particularly this invention relates to tris-phenols of the general formula on 0H 0H CH OH NO: NO:
- the new compounds have been found to have antiseptic properties and to be particularly useful in detergent soap compositions.
- Example I Approximately 18.7 parts by weight of 2-hydroxy-5- nitrobenzyl chloride, approximately 6.4 parts by weight of p-chlorophenol, approximately 50 parts by weight of glacial acetic acid and approximately 5 parts by weight of cone. sulfuric acid are intimately mixed. The mixture so obtained is heated to about 90 C. and held at that temperature overnight with constant agitation. Upon cooling 2. grey-white crystalline mass separates. The cooled reaction mass is filtered. The filter cake is washed with water and then recrystallized from toluene. The recrystallized product is a grey-White crystalline solid having a melting point of 273-274 C. and identified as 4-chloro-a,a'-bis(5-nitro-2-hydroxy-phenyl)-2,6-xylenol.
- Example 11 Employing the procedure of Example I but replacing p-chlorophenol with an equimolecular proportion of pbromophenol there is obtained 4-bromo-a,a'-bis(5-nitro- 2-hydroxy-phenyl) -2,6-xylenol.
- the new compounds are readily incorporated in a detergent soap whether (the soap) be liquid or solid. They, also, remain permanently in the detergent composition and do not afliect the lathering, cleansing or physical properties of the detergent soap. Relatively small amounts of the tris-phenols of this invention in a detergent composition have been found to yield efiicient antiseptic detergent compositions. While amounts in the range of 13% by weight based upon the detergent soap are preferred amounts in the range of 05-10% by weight may be employed where desired.
- soap or detergent soap as employed herein is employed in its popular or ordinary meaning, i. e., cleansing compositions prepared from an alkali metal compound such as potassium or sodium hydroxide and a fat or fatty acid, both saturated and unsaturated.
- An antiseptic detergent composition comprising the combination of a detergent soap and 0.5 to 10% by weight based upon the detergent coap of a compound of claim 1.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
United States Patent ANTISEPTIC SOAP COMPOSITIDN David J. Beaver, Richmond Heights, Roland S. Shumard,
Brentwood, and Paul J. Stofiel, Florissant, Mo., assignors to Monsanto Chemical Company, St. Louis, Mo., a corporation of Delaware No Drawing. Application September 28, 1953, Serial No. 382,831
4 Claims. (Cl. 252-107) This invention relates to new and useful compositions of matter. More particularly this invention relates to tris-phenols of the general formula on 0H 0H CH OH NO: NO:
where X is a halogen atom.
The new compounds have been found to have antiseptic properties and to be particularly useful in detergent soap compositions.
As illustrative of the preparation of the new compounds of this invention is the following:
Example I Approximately 18.7 parts by weight of 2-hydroxy-5- nitrobenzyl chloride, approximately 6.4 parts by weight of p-chlorophenol, approximately 50 parts by weight of glacial acetic acid and approximately 5 parts by weight of cone. sulfuric acid are intimately mixed. The mixture so obtained is heated to about 90 C. and held at that temperature overnight with constant agitation. Upon cooling 2. grey-white crystalline mass separates. The cooled reaction mass is filtered. The filter cake is washed with water and then recrystallized from toluene. The recrystallized product is a grey-White crystalline solid having a melting point of 273-274 C. and identified as 4-chloro-a,a'-bis(5-nitro-2-hydroxy-phenyl)-2,6-xylenol.
Example 11 Employing the procedure of Example I but replacing p-chlorophenol with an equimolecular proportion of pbromophenol there is obtained 4-bromo-a,a'-bis(5-nitro- 2-hydroxy-phenyl) -2,6-xylenol.
As illustrative of the utility of the new compounds of this invention 4 chloro 01,0! bis(5-nitro-2-hydroxyphenyl) -2,6-Xylenol was compounded in an Ivory brand neutral white high grade tallow soap to form a 2% by weight composition. Aliquots were added to a nutrient agar medium so as to give concentrations of 1.25 p. p. m., 2.5 p. p. m., 5 p. p. m. and 10 p. p. III. of 4- chloro-a,a-bis (5-nitro-2-hydroxy-phenyl) -2,6-xylenol in the nutrient agar. The agar in each case was then streaked with a 24 hour culture of Staphylococci aureus of standard resistance. After an incubation period of 72 hours at 37 C. in each case no growth was observed.
The new compounds are readily incorporated in a detergent soap whether (the soap) be liquid or solid. They, also, remain permanently in the detergent composition and do not afliect the lathering, cleansing or physical properties of the detergent soap. Relatively small amounts of the tris-phenols of this invention in a detergent composition have been found to yield efiicient antiseptic detergent compositions. While amounts in the range of 13% by weight based upon the detergent soap are preferred amounts in the range of 05-10% by weight may be employed where desired.
The term soap or detergent soap as employed herein is employed in its popular or ordinary meaning, i. e., cleansing compositions prepared from an alkali metal compound such as potassium or sodium hydroxide and a fat or fatty acid, both saturated and unsaturated.
While the invention has been described in detail with respect to certain embodiments it is not so limited and it is to be understood that modifications and variations obvious to those skilled in the art may be made without departing from the spirit or scope of this invention.
What is claimed is:
1. As a new compound a 4-ha10-a,u.'-biS(S-IfilI'O-Z- hydroxy-phenyl) -2,6-xylenol.
2. 4 chloro (2,11 bis(5 nitro 2 hydroxyphenyl) -2,6-xylenol.
3. 4 bromo 0:,a' bis(5 nitro 2 hydroXy-phenyD- 2,6-xylenol.
4. An antiseptic detergent composition comprising the combination of a detergent soap and 0.5 to 10% by weight based upon the detergent coap of a compound of claim 1.
OTHER REFERENCES Jour. Amer. Chem. soc. vol. 75 (Nov. 20, 1953), pages 5579-81.
Claims (2)
1. AS A NEW COMPOUND A 4-HALO-A,A''-BIS(5-NITRO-2HYDROXY-PHENYL)-2,6-XYLENOL.
4. AN ANTISEPTIC DETERGENT COMPOSITION COMPRISING THE COMBINATION OF A DETERGENT SOAP AND 0.5 TO 10% BY WEIGHT BASED UPON THE DETERGENT SOAP OF A COMPOUND OF CLAIM 1.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US382831A US2713036A (en) | 1953-09-28 | 1953-09-28 | Antiseptic soap composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US382831A US2713036A (en) | 1953-09-28 | 1953-09-28 | Antiseptic soap composition |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2713036A true US2713036A (en) | 1955-07-12 |
Family
ID=23510574
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US382831A Expired - Lifetime US2713036A (en) | 1953-09-28 | 1953-09-28 | Antiseptic soap composition |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2713036A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4282390A (en) * | 1976-07-07 | 1981-08-04 | Ici Australia Limited | 2,6-Benzyl substituted phenols |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2560939A (en) * | 1951-07-17 | - methylenebis |
-
1953
- 1953-09-28 US US382831A patent/US2713036A/en not_active Expired - Lifetime
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2560939A (en) * | 1951-07-17 | - methylenebis |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4282390A (en) * | 1976-07-07 | 1981-08-04 | Ici Australia Limited | 2,6-Benzyl substituted phenols |
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