US1852820A - Soap manufacture - Google Patents

Soap manufacture Download PDF

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Publication number
US1852820A
US1852820A US433177A US43317730A US1852820A US 1852820 A US1852820 A US 1852820A US 433177 A US433177 A US 433177A US 43317730 A US43317730 A US 43317730A US 1852820 A US1852820 A US 1852820A
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United States
Prior art keywords
soap
phenyl
phenolate
prepared
reacting
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
US433177A
Inventor
Paul I Murrill
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.)
Vanderbilt Chemicals LLC
Original Assignee
RT Vanderbilt Co Inc
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 RT Vanderbilt Co Inc filed Critical RT Vanderbilt Co Inc
Priority to US433177A priority Critical patent/US1852820A/en
Priority to FR694286D priority patent/FR694286A/en
Application granted granted Critical
Publication of US1852820A publication Critical patent/US1852820A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D9/00Compositions of detergents based essentially on soap
    • C11D9/04Compositions of detergents based essentially on soap containing compounding ingredients other than soaps
    • C11D9/045Compositions 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
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11BPRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B5/00Preserving by using additives, e.g. anti-oxidants
    • C11B5/0021Preserving by using additives, e.g. anti-oxidants containing oxygen
    • C11B5/0035Phenols; Their halogenated and aminated derivates, their salts, their esters with carboxylic acids
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D9/00Compositions of detergents based essentially on soap
    • C11D9/04Compositions of detergents based essentially on soap containing compounding ingredients other than soaps
    • C11D9/22Organic compounds, e.g. vitamins
    • C11D9/26Organic compounds, e.g. vitamins containing oxygen
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D9/00Compositions of detergents based essentially on soap
    • C11D9/04Compositions of detergents based essentially on soap containing compounding ingredients other than soaps
    • C11D9/22Organic compounds, e.g. vitamins
    • C11D9/30Organic compounds, e.g. vitamins containing nitrogen

Definitions

  • This invention relates to an improved soap composition and to the method of preparing the same.
  • the composition comprises in ad dition to soap a stabilizer which retards, prevents or inhibits the ageing of the soap or certain of the results which ordinarily aecompany the ageing of soap.
  • soap is stabilized by the addition of a small amount of phenolate prepared from a phenyl phenol and a base, the baseitself being a stabilizer for soap.
  • the stabilizers include the phenolates resulting from the interaction of a phenyl phenol such as 2-hydroxy-diphenyl or 4-hydroxy-diphenyl with diphenyl-guanidine or triethanol amine or an alkylene diaryl diamine such as ethylene diphenyl diamine. Mixtures of such phenolates may be employed as stabilizers.
  • soap by adding to soap a small amount of a phenolate of this type, for example, a few tenths of a percent, the soap will be stabilized against oxidation to some extent or rancidity will be prevented or retarded or the formation of free fatty acids within the soap will be prevented or retarded when the soap is subjected to the action of air or sunlight, or more particularly that by adding such a phenolate to soap, the soap may be prevented from becoming dark on ageing or the change in color will be retarded.
  • the stabilizers contemplated by this invention prepared by the interaction of a phenyl phenol with a base, exert a difierent stabilizing effect from a mixture of the phenyl phenol and the base, and theyhave melting points, etc. distinct from both the phenyl phenol and the base. These identify the stabilizers as distinct chemical compounds and theylare referred to herein as phenolates.
  • the phenolates can be prepared either 2-hydroxy-diphenyl or 4- hydroxyiphenyl to react with diphenyl- 1930. Serial No. 433,177.
  • guanidine or triethanol amine or an alkylene diaryl diamine such as ethylene, propylene, trimethylene, tetramethylene or pentamethylene diaryl diamineof which the aryl groups may be phenyl or substitute phenyl such as tolyl or na hthyl, etc.
  • a soap stabilized by a small amount of the phenolate prepared by the interaction of l-hydroxy-diphenyl and an alkylene diaryl diamine such as ethylene diphenyl diamine discolors to a less extent on ageing than a soap stabilized by the addition of a small amount of the phenolate prepared from 2-hydroxy-diphenyl and ethylene diphenyl diamine.
  • the stabilizer may be incorporated in the soap in various ways. It may be added to the soap stock during saponification in an amount equivalent to about 2/10 of a percent calculated on the weight of the soap stock. The desired amount of the phenolate is dissolved in the soap and the saponification is carried on in the usual manner. This method may be employed with stabilizers which are sufliciently insoluble in water and caustic so that they do not go into solution in the spent lyes, but will be present in the finished soap.
  • a solution of the desired amount of phenolate for example, two tenths of .a percent of the phenolate rev pared from 4-hydroxy-dipheny1 and ethylene diphenyl diamine, dissolved in some volatile organic solvent, such as alcohol or benzol, etc., is added to the soap while it is being milled and the stabilizer is thus incorporated into the soap. On milling the heat of the rolls volatilizes the solvent and leaves the stabilizer dispersed throughout the soap.
  • Stabilized soap comprising phenyl phenolate prepared by reactin a phenyl phenolate prepared by reacting l-hydroxy- .phenol with an organic chemical ase aving diphenyl with ethylene diphenyl diamine.
  • T8 2. Stabilized soap comprising a phenyl phenolate prepared by reacting an hydroxydiphenyl with an alkylene diaryl diamine.
  • Stabilized soap comprising a fraction of a percent of a phenyl phenolate prepared from an ortho phenyl phenol and an organic chemical base having alkaline properties whichof itself stabilizes soap.
  • the step which comprises adding to the soap stock a fraction of a percent of a phenylphenolate prepared by reacting a phenyl phenol with an organic chemical base having alkaline properties, which itself serves to stabilize soap.
  • step 7 which comprise dissolving in an organic solvent phenyl phenolate prepared by reacting any hydroXy-diphenyl with an alkylene diaryl diamine, adding the solution to the soap during the milling process and volatilizing the solvent during the milling operation by the heat of the rolls.
  • Stabilized soap comprising a phenyl phenolate prepared by reacting a phenyl phenol with diphenylguanidine.
  • Stabilized soap comprising phenolate prepared by reacting phenol with triethanolamine.
  • Stabilized soap comprising a fraction of a percent of a phenylphenolate prepared from'a para phenyl phenol and an organic chemical. base having alkaline properties which of itself stabilizes soap.
  • Stabilized soap c'omprising the phenyl phenolate of para phenyl phenol and an alkylene diaryldiamine.
  • Stabilized soap comprising phenyl phe-' nolate prepared by reacting a.phenyl phenol f abase which is a member of the group comprising diphenylguanidine, triethanol amine and the alkylene diaryl diamines.
  • the step which comprises adding to the soap stock a fraction of a percent of a-phenyl phenolate prepared by reacting a phenyl phenol with an alkylol amine.
  • the step which comprises adding to the soap stock a fraction of a percent of a phenyl phenolate prepared by reacting a phenyl phenol with ethylene diphenyl diamine.
  • the step which comprises adding to the soap stock a fraction of a percent of a phenyl phenolate prepared by reacting a phenyl phenol with triethanol amine.
  • step Y which comprises adding to the soap during the milling process a small amount of a phenyl phenolate prepared by reacting a phenyl phenol with an alkylene diaryl diamine.
  • the step which comprises addingto the soap during the milling process a small amount of a phenyl phenolate prepared by reacting a phenyl phenol with an alkylol amine.
  • the step which comprises adding to the soap during the milling process a small amount of a phenyl phenolate prepared by reacting a phenyl phenol with ethylene diphenyl diamine.
  • the step which comprises adding to the soap during the milling process a small amount of a phenyl phenolate prepared by reacting a phenyl phenol with dipheny'lguanidine.
  • Stabilized soap comprising a phenyl' CERTIFICATE OF CORRECTION.
  • Patent No. l, 852, 820 Granted April 5, 932, to

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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)
  • Health & Medical Sciences (AREA)
  • Emergency Medicine (AREA)
  • Biochemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Detergent Compositions (AREA)

Description

.by causin atented Apr. 5, 1932 PAUL I. MURRILL, OF EAST NORWALK, CONNECTICUT, ASSIGNOR TO K. T. VANDERBILT COMPANY, INCORPORATED, OF NEW YORK, N. Y., A CORPORATION OF NEW YORK SOAP MANUFACTURE No Drawing. Application filed March 4,
This invention relates to an improved soap composition and to the method of preparing the same. The composition comprises in ad dition to soap a stabilizer which retards, prevents or inhibits the ageing of the soap or certain of the results which ordinarily aecompany the ageing of soap.
According to this invention, soap is stabilized by the addition of a small amount of phenolate prepared from a phenyl phenol and a base, the baseitself being a stabilizer for soap. The stabilizers include the phenolates resulting from the interaction of a phenyl phenol such as 2-hydroxy-diphenyl or 4-hydroxy-diphenyl with diphenyl-guanidine or triethanol amine or an alkylene diaryl diamine such as ethylene diphenyl diamine. Mixtures of such phenolates may be employed as stabilizers.
I do not claim as my invention the stabilization of soap by the addition of either a phenyl phenol or a base such as those mentioned. Iclaim as my invention the stabilization of soap by the addition of a phenolate prepared by interacting a phenyl phenol with such a base. I have found that by adding to soap a small amount of a phenolate of this type, for example, a few tenths of a percent, the soap will be stabilized against oxidation to some extent or rancidity will be prevented or retarded or the formation of free fatty acids within the soap will be prevented or retarded when the soap is subjected to the action of air or sunlight, or more particularly that by adding such a phenolate to soap, the soap may be prevented from becoming dark on ageing or the change in color will be retarded.
The stabilizers contemplated by this invention prepared by the interaction of a phenyl phenol with a base, exert a difierent stabilizing effect from a mixture of the phenyl phenol and the base, and theyhave melting points, etc. distinct from both the phenyl phenol and the base. These identify the stabilizers as distinct chemical compounds and theylare referred to herein as phenolates. The phenolates can be prepared either 2-hydroxy-diphenyl or 4- hydroxyiphenyl to react with diphenyl- 1930. Serial No. 433,177.
guanidine or triethanol amine or an alkylene diaryl diamine such as ethylene, propylene, trimethylene, tetramethylene or pentamethylene diaryl diamineof which the aryl groups may be phenyl or substitute phenyl such as tolyl or na hthyl, etc.
I have ound that a soap stabilized by a small amount of the phenolate prepared by the interaction of l-hydroxy-diphenyl and an alkylene diaryl diamine such as ethylene diphenyl diamine discolors to a less extent on ageing than a soap stabilized by the addition of a small amount of the phenolate prepared from 2-hydroxy-diphenyl and ethylene diphenyl diamine.
The stabilizer may be incorporated in the soap in various ways. It may be added to the soap stock during saponification in an amount equivalent to about 2/10 of a percent calculated on the weight of the soap stock. The desired amount of the phenolate is dissolved in the soap and the saponification is carried on in the usual manner. This method may be employed with stabilizers which are sufliciently insoluble in water and caustic so that they do not go into solution in the spent lyes, but will be present in the finished soap.
As an alternative method, a solution of the desired amount of phenolate, for example, two tenths of .a percent of the phenolate rev pared from 4-hydroxy-dipheny1 and ethylene diphenyl diamine, dissolved in some volatile organic solvent, such as alcohol or benzol, etc., is added to the soap while it is being milled and the stabilizer is thus incorporated into the soap. On milling the heat of the rolls volatilizes the solvent and leaves the stabilizer dispersed throughout the soap.
Soap prepared from cotton seed oil to which a small amount of a phenolate such as that described has been added, has been found to discolor less readily than soa s not so treated. Soaps stabilized with the p leIlOlates also remain sweet longer and have less tendency to become rancid and to decompose with the formation of free fatty acids than soap not so treated. I claim 1. Stabilized soap comprising phenyl phenolate prepared by reactin a phenyl phenolate prepared by reacting l-hydroxy- .phenol with an organic chemical ase aving diphenyl with ethylene diphenyl diamine.
alkaline properties which itself stabilizes soap.
T8: 2. Stabilized soap comprising a phenyl phenolate prepared by reacting an hydroxydiphenyl with an alkylene diaryl diamine.
3. Stabilized soap comprising a fraction of a percent of a phenyl phenolate prepared from an ortho phenyl phenol and an organic chemical base having alkaline properties whichof itself stabilizes soap.
4. In the process of making soap, the step which comprises adding to the soap stock a fraction of a percent of a phenylphenolate prepared by reacting a phenyl phenol with an organic chemical base having alkaline properties, which itself serves to stabilize soap.
5. In the process ofmaking soap, the step which comprises adding to the soap stock a fraction of a percent of a phenyl phenolate prepared by reacting an hydroXy-diphenyl with an organic chemical base having alkaline properties which itself serves to stabilize soa 6? In the process of making soap, the step which comprises adding to the soap during the milling process a small amount of a phenol phenolate prepared by reacting a phenyl phenol with an organic .chemical base having alkaline properties, which itself serves to stabilize soap.
7. In the process of making soap, thesteps which comprise dissolving in an organic solvent phenyl phenolate prepared by reacting any hydroXy-diphenyl with an alkylene diaryl diamine, adding the solution to the soap during the milling process and volatilizing the solvent during the milling operation by the heat of the rolls. I
8. Stabilized soap comprising a phenyl phenolate prepared by reacting a phenyl phenol with diphenylguanidine.
9'. Stabilized soap comprising phenolate prepared by reacting phenol with triethanolamine.
10. Stabilized soap comprising a fraction of a percent of a phenylphenolate prepared from'a para phenyl phenol and an organic chemical. base having alkaline properties which of itself stabilizes soap. I
11. Stabilized soap c'omprising the phenyl phenolate of para phenyl phenol and an alkylene diaryldiamine.
a phenyl a phenyl 12. Stabilized soap comprising phenyl phe-' nolate prepared by reacting a.phenyl phenol f abase which is a member of the group comprising diphenylguanidine, triethanol amine and the alkylene diaryl diamines.
' 13..Stabilized soap comprising a phenyl 15. In the process of making soap, the step which comprises adding to the soap stock a fraction of a percent of a phenyl phenolate prepared by reacting a phenyl phenol with an alkylene diaryl diamine.
16. In the process of making soap, the step which comprises adding to the soap stock a fraction of a percent of a-phenyl phenolate prepared by reacting a phenyl phenol with an alkylol amine. I
17 In the process of making soap, the step which comprises adding to the soap stock a fraction of a percent of a phenyl phenolate prepared by reacting a phenyl phenol with ethylene diphenyl diamine.
18. In the process of making soap, the step which comprises adding to the soap stock a fraction of a percent of a phenyl phenolate prepared by reacting a phenyl phenol with triethanol amine.
19., In the process of making soap, the step Y which comprises adding to the soap during the milling process a small amount of a phenyl phenolate prepared by reacting a phenyl phenol with an alkylene diaryl diamine.
20. In the process of making soap, the step which comprises addingto the soap during the milling process a small amount of a phenyl phenolate prepared by reacting a phenyl phenol with an alkylol amine.
21. In the process of making soap, the step which comprises adding to the soap during the milling process a small amount of a phenyl phenolate prepared by reacting a phenyl phenol with ethylene diphenyl diamine.
22. In the process of making soap, the step which comprises adding to the soap during the milling process a small amount of a phenyl phenolate prepared by reacting a phenyl phenol with dipheny'lguanidine.
23. Inthe process of making soap, the step which comprises addingto the soap during the milling process a small of amount of a phenyl phenolate prepared by reacting a phenyl phenolwith triethanol amine.
In testimony whereof-I affix my signature.
' PAUL' I. MURRILL.
phenolate prepared by reacting an hydroxy diphenyl with an alkylol amine.
14. Stabilized soap comprising a phenyl' CERTIFICATE OF CORRECTION.
Patent No. l, 852, 820. Granted April 5, 932, to
PAUL I. MU RRILL.
It is hereby certified that error appears in the printed specification of the above numbered patent requiring correction as follows: Page 2, lines 29 and 39,
claim 6, for "phenol" read phenyl, and line 37, claim 7, for "any" read an; d-
that' the said Letters Patent should he read with these corrections therein that the same may conform to the record of the case in the Patent Ofiice.
Signed and sealed this 17th day of May, A. D. 1932.
M. J. Moore, acting Coissioner oi ?atento;
(Seal)
US433177A 1930-03-04 1930-03-04 Soap manufacture Expired - Lifetime US1852820A (en)

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US433177A US1852820A (en) 1930-03-04 1930-03-04 Soap manufacture
FR694286D FR694286A (en) 1930-03-04 1930-04-22 Stabilization process for fatty substances and soaps

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2417809A (en) * 1941-10-24 1947-03-25 Dow Chemical Co Amine salts of polychloro-2-hydroxy-diphenyl
US2441665A (en) * 1942-08-07 1948-05-18 Parke Davis & Co Diamines
US2508429A (en) * 1949-02-17 1950-05-23 California Research Corp Compounded bitumen

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2417809A (en) * 1941-10-24 1947-03-25 Dow Chemical Co Amine salts of polychloro-2-hydroxy-diphenyl
US2441665A (en) * 1942-08-07 1948-05-18 Parke Davis & Co Diamines
US2508429A (en) * 1949-02-17 1950-05-23 California Research Corp Compounded bitumen

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Publication number Publication date
FR694286A (en) 1930-12-02

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