US2375626A - Soap antioxidant - Google Patents

Soap antioxidant Download PDF

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Publication number
US2375626A
US2375626A US524780A US52478044A US2375626A US 2375626 A US2375626 A US 2375626A US 524780 A US524780 A US 524780A US 52478044 A US52478044 A US 52478044A US 2375626 A US2375626 A US 2375626A
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US
United States
Prior art keywords
soap
biguanide
tertiary
antioxidant
amylphenyl
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
Application number
US524780A
Inventor
Elmer W Cock
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Wyeth Holdings LLC
Original Assignee
American Cyanamid Co
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by American Cyanamid Co filed Critical American Cyanamid Co
Priority to US524780A priority Critical patent/US2375626A/en
Priority to GB5833/45A priority patent/GB591836A/en
Application granted granted Critical
Publication of US2375626A publication Critical patent/US2375626A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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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
    • C11D9/00—Compositions of detergents based essentially on soap
    • C11D9/04—Compositions of detergents based essentially on soap containing compounding ingredients other than soaps
    • C11D9/22—Organic compounds, e.g. vitamins
    • C11D9/30—Organic compounds, e.g. vitamins containing nitrogen
    • 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
    • C11D9/00—Compositions of detergents based essentially on soap
    • C11D9/04—Compositions of detergents based essentially on soap containing compounding ingredients other than soaps
    • C11D9/045—Compositions of detergents based essentially on soap containing compounding ingredients other than soaps containing substances which prevent the deterioration of soaps, e.g. light or heat stabilisers or antioxidants
    • 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
    • C11D9/00—Compositions of detergents based essentially on soap
    • C11D9/04—Compositions of detergents based essentially on soap containing compounding ingredients other than soaps
    • C11D9/22—Organic compounds, e.g. vitamins
    • C11D9/34—Organic compounds, e.g. vitamins containing phosphorus

Definitions

  • soap I mean ordinary commercial soap, which is an alkali metal salt of a fat acid such as is obtained by the saponiflcation of vegetable or animal fats of the type of tallow, coconut oil and the like.
  • my invention consists in the stabilization of soap against discoloration and rancidity by incorporating therein small but effective amounts of a biguanide p-tertiary 'amylphenyl phosphate. I have found'that a high degree of stabilization is obtained when amounts on the order' of 0.01-0.5% of my new stabilizer are used, based on the weight of the soap.
  • the p-tertiary'amylphenyl phosphoric acids are prepared by reacting p-tertiary amylphenol with mos. Either the monoor the diester may be prepared in this manner and used to form a biguanide or hydrocarbon-substituted biguan- 'ide salt.
  • I prepare a mixture of monoand diesters by heating 1 mole of phosphorous pentoxide with 3 moles of p-tertiary amylphenol with stirring for 1 hour.
  • the reaction product maythen be added to a biguanide such as bi-- guanide itself, mono-phenylbiguanide or monobiphenylbiguanide in alcohol solution, preferably with the application of heat to complete the salt formation.
  • any biguanide which in itself possesses soap stabilizing properties may be combined with p-tertiary amylphenyl phosphoric acid to form a salt, and in all cases it will be found that the stabilizing properties of the biguanide are improved. I prefer, however.
  • preferred compounds are preferably incorporated into the soap in amounts of about 0.01-0.2%, based on the weight of the soap, 0.1% being a suitable quantity.
  • My invention will be described in greater detail by reference to the following specific example.
  • Example Fine white milled soap' having a neutralization number of 0.29, was ground and 0.1% of stabilizer was incorporated by adding 0.015 gram of the stabilizer to 15 grams of the soap.
  • 150 cc. of hot, oxygen-free distilled water was then added and the mixture stirred with heating until the entire mass was dissolved.
  • the solution was poured into a flat dish and cooled to a gel, which was dried to 10% moisture content.
  • Three of the dried films were then united by pressure into a cylindrical cake about inches in thickness, using a hydraulic press and a pressure oi 2160 pounds per square inch for 15 minutes.
  • the resulting soap bar was placed in a jar fitted with a screw cap. A number of samples containing.

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  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Biochemistry (AREA)
  • Detergent Compositions (AREA)

Description

Patented May 8, 1945 soar ANTIOXIDANT Elmer w. Cook, New York, N. Y., assignor to American Cyanamid Company,
New York,
N. Y., a corporation of Maine No Drawing. Application March 2, 1944, Serial No. 524,780
2 Claims.
This invention relates to an improvement in soap and soap products, and more particularly to the stabilization of. soap against discoloration and rancidity upon storage. By "soap I mean ordinary commercial soap, which is an alkali metal salt of a fat acid such as is obtained by the saponiflcation of vegetable or animal fats of the type of tallow, coconut oil and the like.
I have-found that the biguanide andhydrocarbon-substituted biguanide salts of p-tertiary amylphenyl phosphoric acids are improved soap stabilizers and will prevent discoloration and rancidity in soap to a markeddegree. Accordingly, my invention consists in the stabilization of soap against discoloration and rancidity by incorporating therein small but effective amounts of a biguanide p-tertiary 'amylphenyl phosphate. I have found'that a high degree of stabilization is obtained when amounts on the order' of 0.01-0.5% of my new stabilizer are used, based on the weight of the soap.
,Biguanide itself and such substituted biguanides as mono-orthotolyl biguanide, mono-phenyl biguanide, mono-xylyl biguanide and bi-phenyl biguanide have hitherto been used as soap stabilizers, either as such or in the form of salts with hydrochloric acid. However, the hydrochlorldes and other simple salts'of these biguanide compounds are no better stabilize'rsthan are the biguanides themselves. It is therefore quite surprising to mid that the p-tertiary amylphenyl phosphate salts of these biguanides improved soap st bilizing properties, for the alkali metal and other simple salts of p-tertiary amylphenyl phosphate possess little or no soap stabilizing properties.
The p-tertiary'amylphenyl phosphoric acids are prepared by reacting p-tertiary amylphenol with mos. Either the monoor the diester may be prepared in this manner and used to form a biguanide or hydrocarbon-substituted biguan- 'ide salt. Preferably I prepare a mixture of monoand diesters by heating 1 mole of phosphorous pentoxide with 3 moles of p-tertiary amylphenol with stirring for 1 hour. The reaction product maythen be added to a biguanide such as bi-- guanide itself, mono-phenylbiguanide or monobiphenylbiguanide in alcohol solution, preferably with the application of heat to complete the salt formation. 1
In practicing my invention any biguanide which in itself possesses soap stabilizing properties may be combined with p-tertiary amylphenyl phosphoric acid to form a salt, and in all cases it will be found that the stabilizing properties of the biguanide are improved. I prefer, however.
preferred compounds are preferably incorporated into the soap in amounts of about 0.01-0.2%, based on the weight of the soap, 0.1% being a suitable quantity. My invention will be described in greater detail by reference to the following specific example.
Example Fine white milled soap', having a neutralization number of 0.29, was ground and 0.1% of stabilizer was incorporated by adding 0.015 gram of the stabilizer to 15 grams of the soap. 150 cc. of hot, oxygen-free distilled water was then added and the mixture stirred with heating until the entire mass was dissolved. The solution was poured into a flat dish and cooled to a gel, which was dried to 10% moisture content. Three of the dried films were then united by pressure into a cylindrical cake about inches in thickness, using a hydraulic press and a pressure oi 2160 pounds per square inch for 15 minutes. The resulting soap bar was placed in a jar fitted with a screw cap. A number of samples containing.
'various soap antioxidants were prepared in, this .-tion before aging and T1 equals percent reflection after agin In all cases the results given were obtained after an aging time of seven days.
What I claim is:
rancidity by 'the presence therein of stabilizing amounts of a biguanide salt of a p-tertiary amylphenyl phosphoric acid, said soap being an alkali metal saltof a'fat acid.
2. Soap, stabilized against discoloration 0nd rancidity by the presence therein of stabilizing amounts of a mono-phenyi biguanide salt of a "p-tertiary amylphenyl phosphoric acid, said soap to use the p-tertiary amylphenyl phosphate salts oi the mono-aryl biguanides, and particularly the monophenyl and substituted monophenyl blguanm ides such as those enumerated above. These being an alkali metal salt oi a fat acid.
' mm w. 0001:.
US524780A 1944-03-02 1944-03-02 Soap antioxidant Expired - Lifetime US2375626A (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
US524780A US2375626A (en) 1944-03-02 1944-03-02 Soap antioxidant
GB5833/45A GB591836A (en) 1944-03-02 1945-03-08 Soap antioxidant

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US524780A US2375626A (en) 1944-03-02 1944-03-02 Soap antioxidant

Publications (1)

Publication Number Publication Date
US2375626A true US2375626A (en) 1945-05-08

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Family Applications (1)

Application Number Title Priority Date Filing Date
US524780A Expired - Lifetime US2375626A (en) 1944-03-02 1944-03-02 Soap antioxidant

Country Status (2)

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US (1) US2375626A (en)
GB (1) GB591836A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2903393A (en) * 1958-01-17 1959-09-08 Virginia Carolina Chem Corp Diethylamine addition products of acid phosphates

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2903393A (en) * 1958-01-17 1959-09-08 Virginia Carolina Chem Corp Diethylamine addition products of acid phosphates

Also Published As

Publication number Publication date
GB591836A (en) 1947-08-29

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