GB2240111A - Synergistic lime soap dispersant - Google Patents

Synergistic lime soap dispersant Download PDF

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Publication number
GB2240111A
GB2240111A GB9100968A GB9100968A GB2240111A GB 2240111 A GB2240111 A GB 2240111A GB 9100968 A GB9100968 A GB 9100968A GB 9100968 A GB9100968 A GB 9100968A GB 2240111 A GB2240111 A GB 2240111A
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GB
United Kingdom
Prior art keywords
soap
composition according
weight ratio
amine oxide
sodium cocoyl
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.)
Withdrawn
Application number
GB9100968A
Other versions
GB9100968D0 (en
Inventor
Kim Renae Smith
James Ellwood Borland
Joe Dean Sauer
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.)
Ethyl Corp
Original Assignee
Ethyl Corp
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
Priority claimed from US07/468,763 external-priority patent/US5024777A/en
Priority claimed from US07/542,308 external-priority patent/US5102572A/en
Application filed by Ethyl Corp filed Critical Ethyl Corp
Publication of GB9100968D0 publication Critical patent/GB9100968D0/en
Publication of GB2240111A publication Critical patent/GB2240111A/en
Withdrawn legal-status Critical Current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
    • C11D10/00Compositions of detergents, not provided for by one single preceding group
    • C11D10/04Compositions of detergents, not provided for by one single preceding group based on mixtures of surface-active non-soap compounds and soap
    • C11D10/042Compositions of detergents, not provided for by one single preceding group based on mixtures of surface-active non-soap compounds and soap based on anionic surface-active compounds and soap
    • 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
    • C11D10/00Compositions of detergents, not provided for by one single preceding group
    • C11D10/04Compositions of detergents, not provided for by one single preceding group based on mixtures of surface-active non-soap compounds and soap
    • C11D10/045Compositions of detergents, not provided for by one single preceding group based on mixtures of surface-active non-soap compounds and soap based on non-ionic surface-active compounds and soap
    • 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
    • C11D1/00Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/02Anionic compounds
    • C11D1/12Sulfonic acids or sulfuric acid esters; Salts thereof
    • C11D1/126Acylisethionates
    • 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
    • C11D1/00Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/02Anionic compounds
    • C11D1/12Sulfonic acids or sulfuric acid esters; Salts thereof
    • C11D1/16Sulfonic acids or sulfuric acid esters; Salts thereof derived from divalent or polyvalent alcohols
    • 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
    • C11D1/00Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/66Non-ionic compounds
    • C11D1/75Amino oxides

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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)
  • Detergent Compositions (AREA)

Abstract

A bar soap composition containing a fatty acid soap is provided with superior lime soap dispersing properties by the inclusion therein of a synergistic mixture of (1) an N-alkyl-N,N-dimethylamine oxide in which the alkyl group contains 8-20 carbons and either (2) sodium cocoyl isethionate or (3) sodium cocoyl glyceryl sulfonate in a weight ratio of 0.3-3/1 or 0.05-2.3/1, respectively.

Description

SYNERGISTIC LIME SOAP DISPERSANTS This invention relates to soap compositions and more particularly to fatty acid soap compositions having superior lime soap dispersing properties.
It is known that the use of fatty acid soap compositions in water containing calcium and/or magnesium ions leads to the deposition of insoluble lime soap and that this deposition is conducive to the scum frequently seen in sinks and bathtubs. The use of a detergent as a lime soap dispersant can prevent this deposition, but lime soap dispersants that have previously been used in soap compositions have not been sufficiently efficient.
Sodium cocoyl isethionate, sodium cocoyl glyceryl sulfonate, and N-alkyl-N,N-dimethylamine oxides having 8-20 carbons in the alkyl group are known surfactants.
However, the amine oxides have not found wide application in the formulation of toilet soap bars because of having been available only as dilute aqueous solutions which lead to a decomposition problem when the excess water is removed at normal evaporation temperatures and which lead to a frothing problem when the excess water is removed at lower temperatures under vacuum.
As taught in European Patent Application 0401503 (Smith et al.), it has now been found possible to prepare solid N-alkyl-N,N-dimethylamine oxides in a practical manner. Thus, the use of the amine oxides in the formulation of soap bars has become more attractive.
It has now been found that soap compositions containing both an N-alkyl-N,N-dimethylamine oxide in which the alkyl group contains 8-20 carbons and either sodium cocoyl isethionate or sodium cocoyl glyceryl sulfonate exhibit a synergistic suppression of the amount of lime soap deposits formed in hard water when the amine oxide and isethionate are used in a weight ratio of 0.3-3/1 and the amine oxide and sulfonate are used in a weight ratio of 0.05-2.3/1.
The N-alkyl-N,N-dimethylamine oxides which may be used in the practice of the invention are those in which the alkyl group contains 8-20 carbons, preferably 12-18 carbons. Exemplary of such compounds are those in which the alkyl group is octyl, 2-ethylhexyl, 2-ethyloctyl, decyl, dodecyl, 2-ethyldecyl, tetradecyl, hexadecyl, octadecyl, or eicosyl; and the preferred amine oxides are those in which the alkyl groups are mainly linear primary alkyl groups which are at least 75%, preferably at least 90% straight chain. N-tetradecyl-N,N-dimethylamine oxide and N-hexadecyl-N,N-dimethylamine oxide are especially preferred.
Although the amine oxide may be introduced into the soap composition as a conventional dilute aqueous solution, it is ordinarily preferred to avoid the consequences of using a dilute solution by utilizing a solid or liquid amine oxide which does not contain excess water. This amine oxide may be anhydrous, or it may be a monohydrate or dihydrate; and mixtures of anhydrous amine oxide, amine oxide monohydrate, and amine oxide dihydrate are also utilizable.
In a preferred embodiment of the invention, the amine oxide is a product prepared by the process of Smith et al. More specifically, it is an amine oxide prepared by (1) oxidizing the corresponding N-alkyl-N,N-dimethylamine with aqueous hydrogen peroxide in an organic solvent, such as ethyl acetate or other such ester, in which the amine and product amine oxide are soluble at the reaction temperatures but in which the product is insoluble at an ambient or lower temperature and (2) adjusting the water content of the product, if necessary, to achieve a water/amine oxide mol ratio of 1.9-2.1/1.
The product of such a reaction is an amine oxide dihydrate or a mixture thereof with the corresponding anhydrous amine oxide and/or the corresponding amine oxide monohydrate: and it may be a liquid or solid, depending on its molecular weight. When the amine oxide is a dihydrate, it melts at about 15-C when the alkyl group is octyl, 22-230C when the alkyl group is decyl, 30-31C when the alkyl group is dodecyl, and still higher temperatures as the alkyl group is further lengthened.
As already indicated, the N-alkyl-N,N-dimethylamine oxide/sodium cocoyl glyceryl sulfonate weight ratio in the soap composition should be in the range of 0.05-2.3/1 in order to achieve synergism in suppressing lime soap deposits; and this ratio is preferably 0.25-1.5/1, more preferably 0.3-1.2/1. The N-alkyl-N,Ndimethylamine oxide/sodium cocoyl isethionate weight ratio in the composition should be in the range of 0.3-3/1, preferably 0.7-1.5/1, more preferably 1/1.
The amount of each component of the synergistic mixture used in the soap composition generally varies from 1-40%, preferably 5-25%, based on the total weight of the composition; and it is a surprising feature of the invention that the synergism between the components of the mixture makes it possible for the lime soap dispersant to be effective when used in amounts that are less than 15%, and sometimes even less than 10% by weight, based on the weight of the fatty acid soap component of the composition.
Except for the inclusion of the lime soap dispersant of the invention, the soap composition is a conventional one. Thus, it generally contains 5-95%, preferably 10-90%, and most preferably 25-75% by weight of a fatty acid soap and may contain other components, such as titanium dioxide, glycerol or other polyol moisturizer, fragrances, bactericides, fungicides, dyes, fatty acids, polyglycols, alkanolamines, witch hazel, citric acid, opalescent agents, opacity agents, water, and additional synthetic detergents.
Synthetic detergents which may be used in combination with the lime soap dispersant include sodium cocoyl N-methyltauride, sodium oleylsulfate, sodium monolauryl sulfosuccinate, the sodium salt of a mono-oleic acid ester of glycerol sulfate, sodium lauryl sulfoacetate, sodium isostearoyl-2-lactylate, lauryl diethanolamide, and the like. When used, the optional detergent may be employed in an amount such as to constitute up to about 80% of the weight of the soap composition, e.g., 10-75% of that weight.
The fatty acid soap which is an essential component of the soap composition may be any conventional soap, such as an alkali metal or ammonium salt obtained by reacting a neutralizing agent, such as an alkali metal hydroxide, triethanolamine, or coco diethanolamine, preferably sodium hydroxide, with one or more fatty acids, such as tallow acid, oleic acid, stearic acid, or coco acid, very usefully an 80/20 mixture of tallow and coco fatty acids.
The soap composition of the invention may be prepared by conventional procedures as long as any heating that could decompose the amine oxide is accomplished before the amine oxide is incorporated. Since the amine oxides decompose at elevated temperatures, heating above 1000C is preferably avoided, and heating above 120C should certainly be avoided after the amine oxide has been incorporated.
A particularly useful method of preparing the formulation is to pre-mix all ingredients that require drying, heat this pre-mixture to drive off water until the desired water content (usually about 10%) is achieved, feed the dehydrated mixture to a three-roll mill together with the amine oxide and any other ingredients, thoroughly blend the mixture, extrude it into an elongated log, cut the log into soap bar-size segments, and place each segment in a two-piece mold in which it is compressed to form the final soap bar.
The following examples are given to illustrate the invention and are not intended as a limitation thereof.
Unless otherwise specified, quantities mentioned in the examples are quantities by weight.
EXAMPLE I Preparation of Amine Oxide Charge a suitable reaction vessel with 100g of N-tetra- decyl-N,N-dimethylamine and 0.5g of diethylenetriaminepentaacetic acid. Heat with stirring to 65it, add 23g of 70% aqueous hydrogen peroxide dropwise over a period of 15 minutes, heat the mixture to 76so, and stir at that temperature for seven hours. Add 34 mL of ethyl acetate dropwise as needed to maintain a clear, gel-free liquid. Add an additional 400mL of ethyl acetate to the crude reaction mass, which NMR shows to have reached 99% amine conversion. Cool the resultant solution to 150C to form a non- hygroscopic, white, crystalline, solid N-tetradecyl-N, N-di-methylamine oxide dihydrate melting at about 41C in 86% recovered yield.
EXAMPLE II Test of Lime Soap DisDersanev Test the lime soap dispersancy of N-+atradecyl- N,N-dimethylamine oxide dihydrate, sodium cocoyl glyceryl sulfonate, and mixtures thereof by (1) adding a measured amount of the dispersing agent to 10 mL of a 1% calcium stearate slurry, (2) shaking the resultant sample in a test tube while also shaking a control containing no dispersant in another test tube, (3) comparing the test tubes for complete dispersion of the calcium stearate after allowing them to stand for two minutes, and (4) varying the amount of dispersant added to the slurry to determine the minimum amount of dispersant required to attain complete dispersion of 100g of calcium stearate.
The dispersants used and the minimum amounts required are shown below.
Dispersant Amount Amine oxide 15g Amine oxide/sulfonate (1/3) 9g Amine oxide/sulfonate (1/1) 6g Amine oxide/sulfonate (3/1) 15g Sul fonate 16g EXAMPLE III Test of Lime Soap Dispersancs Repeat Example II except for using sodium cocoyl isethionate instead of sodium cocoyl glyceryl sulfonate.
The dispersants used and the minimum amounts required are shown below.
Dispersant Amount Amine oxide 16g Amine oxide/isethionate (3/1) 13g Amine oxide/isethionate (1/1) 8g Amine oxide/isethionate (1/3) 11.5g Isethionate 41g

Claims (10)

  1. CLAIMS 1. A bar soap composition containing a fatty acid soap and, as a lime soap dispersant, a synergistic mixture of (1) an N-alkyl-N,N-dimethylamine oxide in which the alkyl group contains 8 to 20 carbons and either (2) sodium cocoyl isethionate or (3) sodium cocoyl glyceryl sulfonate in a weight ratio of 0.3-3/1 or 0.05-2.3/1, respectively.
  2. 2. A composition according to claim 1 wherein the lime soap dispersant is a synergistic mixture of an N-alkyl-N,Ndimethylamine oxide and sodium cocoyl isethionate in a weight ratio of 0.3-3/1.
  3. 3. A composition according to claim 2 wherein the weight ratio is 0.7-1.5/1.
  4. 4. A composition according to claim 3 wherein the weight ratio is 1/1.
  5. 5. A composition according to claim 1 wherein the lime soap dispersant is a synergistic mixture of an N-alkyl-N,Ndimethyl-amine oxide and sodium cocoyl glyceryl sulfonate in a weight ratio of 0.05-2.3/1.
  6. 6. A composition according to claim 5 wherein the weight ratio is 0.25-1.5/1.
  7. 7. A composition according to claim 6 wherein the weight ratio is 0.3-1.2/1.
  8. 8. A composition according to any one of the preceding claims wherein the alkyl group of 8 to 20 carbons is a mainly linear primary alkyl group.
  9. 9. A composition according to claim 8 wherein the alkyl group contains 12 to 18 carbons.
  10. 10. A composition according to any one of the preceding claims which contains less than 10% by weight of the lime soap dispersant, based on the weight of the fatty acid soap.
GB9100968A 1990-01-23 1991-01-16 Synergistic lime soap dispersant Withdrawn GB2240111A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US07/468,763 US5024777A (en) 1990-01-23 1990-01-23 Synergistic lime soap dispersing composition
US07/542,308 US5102572A (en) 1990-06-22 1990-06-22 Lime soap dispersant comprising sodium cocoyl glyceryl sulfonate and N-alkyl-N,N-dimethylamine oxide

Publications (2)

Publication Number Publication Date
GB9100968D0 GB9100968D0 (en) 1991-02-27
GB2240111A true GB2240111A (en) 1991-07-24

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5310508A (en) * 1992-07-15 1994-05-10 Colgate-Palmolive Company Mild personal cleansing compositions containing sodium alcohol ethoxy glyceryl sulfonate
WO1998055584A1 (en) * 1997-06-03 1998-12-10 The Procter & Gamble Company A laundry bar comprising soap, linear alkyl benzene sulfonate and amine oxide

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1227959A (en) * 1967-07-20 1971-04-15

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1227959A (en) * 1967-07-20 1971-04-15

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5310508A (en) * 1992-07-15 1994-05-10 Colgate-Palmolive Company Mild personal cleansing compositions containing sodium alcohol ethoxy glyceryl sulfonate
WO1998055584A1 (en) * 1997-06-03 1998-12-10 The Procter & Gamble Company A laundry bar comprising soap, linear alkyl benzene sulfonate and amine oxide

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Publication number Publication date
GB9100968D0 (en) 1991-02-27

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