US2221333A - Stabilized soap - Google Patents
Stabilized soap Download PDFInfo
- Publication number
- US2221333A US2221333A US102332A US10233236A US2221333A US 2221333 A US2221333 A US 2221333A US 102332 A US102332 A US 102332A US 10233236 A US10233236 A US 10233236A US 2221333 A US2221333 A US 2221333A
- Authority
- US
- United States
- Prior art keywords
- soap
- biguanide
- mono
- ortho
- rancidity
- 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
- 239000000344 soap Substances 0.000 title description 33
- 229940123208 Biguanide Drugs 0.000 description 12
- -1 biguanide compound Chemical class 0.000 description 9
- 239000003381 stabilizer Substances 0.000 description 9
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 7
- 150000003839 salts Chemical class 0.000 description 6
- XNCOSPRUTUOJCJ-UHFFFAOYSA-N Biguanide Chemical compound NC(N)=NC(N)=N XNCOSPRUTUOJCJ-UHFFFAOYSA-N 0.000 description 5
- 230000006866 deterioration Effects 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 150000004283 biguanides Chemical class 0.000 description 4
- 235000010290 biphenyl Nutrition 0.000 description 4
- 239000004305 biphenyl Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 150000004665 fatty acids Chemical class 0.000 description 3
- CUQCMXFWIMOWRP-UHFFFAOYSA-N phenyl biguanide Chemical compound NC(N)=NC(N)=NC1=CC=CC=C1 CUQCMXFWIMOWRP-UHFFFAOYSA-N 0.000 description 3
- 230000000087 stabilizing effect Effects 0.000 description 3
- FKPUYTAEIPNGRM-UHFFFAOYSA-N 1-(diaminomethylidene)guanidine;hydron;chloride Chemical compound [Cl-].N\C([NH3+])=N/C(N)=N FKPUYTAEIPNGRM-UHFFFAOYSA-N 0.000 description 2
- 235000013162 Cocos nucifera Nutrition 0.000 description 2
- 244000060011 Cocos nucifera Species 0.000 description 2
- FHUDRDSKZQDCBC-UHFFFAOYSA-N [(e)-n'-(n'-phenylcarbamimidoyl)carbamimidoyl]azanium;chloride Chemical compound Cl.NC(N)=NC(N)=NC1=CC=CC=C1 FHUDRDSKZQDCBC-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical group C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
- 238000002845 discoloration Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical class O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000002542 deteriorative effect Effects 0.000 description 1
- 229940035422 diphenylamine Drugs 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, 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
- C11B5/00—Preserving by using additives, e.g. anti-oxidants
- C11B5/0042—Preserving by using additives, e.g. anti-oxidants containing nitrogen
- C11B5/005—Amines or imines
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, 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
- C11B5/00—Preserving by using additives, e.g. anti-oxidants
- C11B5/0042—Preserving by using additives, e.g. anti-oxidants 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
- C11D9/30—Organic compounds, e.g. vitamins containing nitrogen
Definitions
- Patented Nov. '12, 1940 1 UNITED STATES PATENT OFFICE g STABILIZED SOAP Robert L. Sibley, Nitro, W. Va. assignor to Monsanto poration of Delaware No Drawing. a Application September 24, 1936,
- the present invention relates to the manuiacture of soap and soap products, and more par- Chemical Company, St. Louis, Mo., a cor- 5 Olaims. (C1. 23-250) short time.
- One of the objects of the greatest invention is to inhibit or retard this deteriorating
- the present invention comprises the use in the stabilization of soap and soap products of biguanides possessing the gen-v eral formula of wherein R is hydrogen or an organic radical, as for example an alkyl, aryl, aralkyl and alicyclic radical.
- the preferred stabilizing agent may be introduced at any the stabilizing agent may be incorporated into the dry soap in the well-known crutching process.
- a soap comprising a water soluble salt of a higher fatty acid stabilized against deterioration'and development of rancidity by having in- ,corporated therein more than 0.01% of a mono aryl substituted bizuanide.
- a soap comprising a water soluble salt of a higher fatty acid stabilized ag nst deterioration and development of rancidity y having incurporated therein more than 0.01% of an aryl hydrocarbon substituted biguanide said aryl substituent being selected from the benzene, biphenyl and naphthalene series.
- a soap comprising a watersoluble salt of a higher fatty acid stabilized against deterioration and development of rancidity by having incorporated therein more than 0.01% of mono ortho tolyl blguanide.
- a soap comprising a water soluble salt of a higher acid stabilized against deterioration and development of rancidity by having incorporat-' ed therein more than 0.01% of mono xylyi biguanide.
- a soap comprising a water soluble salt of a higher fatty. acid stabilized against deterioration and development of rancidity by having incorporatedtherein more than 0.01% of mono phenyl biguanide.
Landscapes
- 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 Nov. '12, 1940 1 UNITED STATES PATENT OFFICE g STABILIZED SOAP Robert L. Sibley, Nitro, W. Va. assignor to Monsanto poration of Delaware No Drawing. a Application September 24, 1936,
Serial No. 102,332
The present invention relates to the manuiacture of soap and soap products, and more par- Chemical Company, St. Louis, Mo., a cor- 5 Olaims. (C1. 23-250) short time.
One of the objects of the greatest inventionis to inhibit or retard this deteriorating,
action by incorporating in the soap stock, or soap, or in one or more of the ingredients used in the manufacture ther eof, a small quantity of one or more of the preferred class of substances herein disclosed.
In accordance with the present invention it has been found that on incorporating in an unstable soap a relatively small proportion of a biguanide compound, as for example biguanide and its substitution products, salts and derivatives thereof, its tendency to develop rancidlty is markedly lessened and the treated soap rendered substantially stable.
More particularly the present invention comprises the use in the stabilization of soap and soap products of biguanides possessing the gen-v eral formula of wherein R is hydrogen or an organic radical, as for example an alkyl, aryl, aralkyl and alicyclic radical.
In practicing the present invention, the preferred stabilizing agent may be introduced at any the stabilizing agent may be incorporated into the dry soap in the well-known crutching process.
As one method of testing the stabilizing properties of the preferred class of materials, the following procedure was employed:
A substantially neutral soap w as prepared by saponifying a. mixture of substantially three parts of an edibletallow and substantially one part of cocoanut oil with sodium hydroxide. Substantially 0.1% based on the weight of the soap (0.005 gram) ,of one of thepreferred stabilizers 6 was incorporated therein by a suitable means. Five grams of the treated soap were placed in a 250 c. c. iodineflask, a piece of filter paper saturated with water was torn to small pieces and placed in the flask. The flask was then tightly 10 stoppered and placed in an oven maintained at a constanttemperature of 50 C. At the end ofeach day the stopper was removed and any odor indicative of rancidlty noted. Similar tests were carried out with the same soap but to which no 15 stabilizer was added, and the period of stability compared as hereinafter set iorth.
As specific examples andjas specific embodiments of the present invention, but in no sense to be understood as limitative of the scope of the 20 invention, the ,following biguanide compounds were incorporated in a soap of the above composition and tested in the manner described. At the end of the test period indicated in the table below, the soaps containing the preferred ma-% terials had remained stable, having failed to develop rancidlty, and undoubtedly'would have reu mained stable for much longer periods of time.
Table I v Stabilizing en Stabilizing agent la ed 6n g? the weight or the soap Per cent Days Mono ortho tollyl biguanide..- 0. 1 20 Alpha dipheny biguanidem" 0. 1 16 Mono p-phenetidyl bi 0. 1 16- Mono ortho biphenyl do 0. 1 l3 Mono phenyl biguanide hydrochloride 0. 1 l2 Mono phenyl biguanide 0. 1 12 0 Mono xylyl biguanide 0. 1 l8 Mono xylyl biguanide hydrochloride 0. 1 18 Mono ortho anisidyibi anidehydrochlorid 0. l 18 Mono ortho anisidyl b guanid 0. l 18 Mono para biphenyl biguanide-. 0. 1 18 Blank None 4 Another important advantage in the use of the preferred stabilizers isthe fact that, while they are exceptionally strong stabilizers against rancidity formation, they do not generally discolor the soap on exposure to sunlight. Many of the 50 stabilizers heretofore employed in the soap industry were exceptionally bad discolorers of soap. One specific example is diphenyl amine. The preferred materials of the present inventionfor the most part not only do not discolor the soap 55 on vent its butverymarksdlym to sunlight. discoloration when so exposed. Thus,
soaps prepared from-edible tallow and cocoanut oil as described above and containing 0.1%, based on the weight'of, the soap, of mono'ortho tolyl biguanide, alpha diphenyl biguahide, mono phenyl biguanide hydrochloride, mono phenyl biguanide, mono .xylyl biguanide. mono xylyl biguanide hydrochloride, mono ortho anisidyl biguanide hydrochloride, mono ortho anisidyl biguanide and mono ortho phenetidyl biguanide respectively showed no discoloration when exposed to direct sunlight for one hundred hours.
From the above data it is shown that the preferred class of compounds exceptional stabilizing properties when incorporated in soap and soap products. s 7
Other biguanide' compounds which have been employed to good advantage in the. practice of this invention include alpha naphthyl biguanide, alpha naphthyl biguanide hydrochloride and biguanide hydrochloride. Included within the scope of this invention is the use of the analogues in the manufacture thereof, for effecting the desired result, may be varied, but in general it will be found that good results may be obtained by adding on a weight from 0.01% 1.0%
. specification.
of the stabilizing agent to the soap or soap stock.
The present invention is limited solely by the following claims attached hereto as part of the What is claimed is: a t
1. A soap comprising a water soluble salt of a higher fatty acid stabilized against deterioration'and development of rancidity by having in- ,corporated therein more than 0.01% of a mono aryl substituted bizuanide.
2. A soap comprising a water soluble salt of a higher fatty acid stabilized ag nst deterioration and development of rancidity y having incurporated therein more than 0.01% of an aryl hydrocarbon substituted biguanide said aryl substituent being selected from the benzene, biphenyl and naphthalene series.
s. a soap comprising a watersoluble salt of a higher fatty acid stabilized against deterioration and development of rancidity by having incorporated therein more than 0.01% of mono ortho tolyl blguanide.
4. A soap comprisinga water soluble salt of a higher acid stabilized against deterioration and development of rancidity by having incorporat-' ed therein more than 0.01% of mono xylyi biguanide.
5. A soap comprising a water soluble salt of a higher fatty. acid stabilized against deterioration and development of rancidity by having incorporatedtherein more than 0.01% of mono phenyl biguanide.
aonn'm' 1;. BIBLEY.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US102332A US2221333A (en) | 1936-09-24 | 1936-09-24 | Stabilized soap |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US102332A US2221333A (en) | 1936-09-24 | 1936-09-24 | Stabilized soap |
| GB3463938A GB521863A (en) | 1938-11-28 | 1938-11-28 | Improvements in and relating to soap |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2221333A true US2221333A (en) | 1940-11-12 |
Family
ID=26262375
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US102332A Expired - Lifetime US2221333A (en) | 1936-09-24 | 1936-09-24 | Stabilized soap |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2221333A (en) |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2446421A (en) * | 1944-11-03 | 1948-08-03 | Ici Ltd | Manufacture of arylbiguanide hydrochlorides |
| US2463478A (en) * | 1946-11-14 | 1949-03-01 | Socony Vacuum Oil Co Inc | Stabilization of pyrrole with a biguanide |
| US2467295A (en) * | 1945-02-01 | 1949-04-12 | American Cyanamid Co | Stabilization of soap |
| US2469745A (en) * | 1946-06-21 | 1949-05-10 | Standard Oil Dev Co | Stabilizing aromatic amines |
| US2474182A (en) * | 1947-02-26 | 1949-06-21 | Nat Alfalfa Dehydrating And Mi | Preservation of pigments in alfalfa |
| US2577593A (en) * | 1946-12-21 | 1951-12-04 | Du Pont | Stabilizing cellulose yarns |
| US2680122A (en) * | 1951-09-14 | 1954-06-01 | Swift & Co | Stabilization of fats for soap |
| US2961377A (en) * | 1957-08-05 | 1960-11-22 | Us Vitamin Pharm Corp | Oral anti-diabetic compositions and methods |
| US3349099A (en) * | 1959-07-22 | 1967-10-24 | Ciba Geigy Corp | Aminoaryl-guanylhydrazones |
-
1936
- 1936-09-24 US US102332A patent/US2221333A/en not_active Expired - Lifetime
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2446421A (en) * | 1944-11-03 | 1948-08-03 | Ici Ltd | Manufacture of arylbiguanide hydrochlorides |
| US2467295A (en) * | 1945-02-01 | 1949-04-12 | American Cyanamid Co | Stabilization of soap |
| US2469745A (en) * | 1946-06-21 | 1949-05-10 | Standard Oil Dev Co | Stabilizing aromatic amines |
| US2463478A (en) * | 1946-11-14 | 1949-03-01 | Socony Vacuum Oil Co Inc | Stabilization of pyrrole with a biguanide |
| US2577593A (en) * | 1946-12-21 | 1951-12-04 | Du Pont | Stabilizing cellulose yarns |
| US2474182A (en) * | 1947-02-26 | 1949-06-21 | Nat Alfalfa Dehydrating And Mi | Preservation of pigments in alfalfa |
| US2680122A (en) * | 1951-09-14 | 1954-06-01 | Swift & Co | Stabilization of fats for soap |
| US2961377A (en) * | 1957-08-05 | 1960-11-22 | Us Vitamin Pharm Corp | Oral anti-diabetic compositions and methods |
| US3349099A (en) * | 1959-07-22 | 1967-10-24 | Ciba Geigy Corp | Aminoaryl-guanylhydrazones |
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