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Fatty acids, soaps, surfactant systems and consumer products based thereon

A methyl and ethyl technology, applied in surface active detergent compositions, nonionic surface active compounds, anionic surface active compounds, etc., can solve the problems of limited utilization of large-capacity applications, unsuitable surfactants, expensive and other problems

Inactive Publication Date: 2001-02-07
THE PROCTER & GAMBLE COMPANY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Perhaps the most common type of branched fatty acid, such as isostearic acid, can be used as a surfactant, but is too expensive, has limited availability for high-volume applications, and lacks formulation flexibility; there are also short-chain types such as 2 - Ethylhexanoic acid, but these are relatively unsuitable as surfactants
In short, formulators are severely limited in their flexibility when relying on only a small number or blends of these commonly commercially available branched fatty acids

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0130] 5-Methylpentadecanoic acid

[0131] See General Method I. Decyl bromide (compound (1), R=CH 3 (CH 2 ) 9 -) into the Grignard reagent (I, step (a)). To this was added 5-chloro-2-pentanone (Aldrich C6, 2660-3) (I, step (b)). The reaction mixture is reacted with acetic anhydride (I, step (c)) to form the chloroacetate (3). Removal of acetic acid (I, step (d)) by refluxing (3) in a suitable solvent such as benzene yields a mixture of chlorinated olefin isomers (4). (4) is converted to its Grignard reagent (I, step (e)) by standard practice techniques. Treatment of the Grignard reagent (I, step (f)) with carbon dioxide and acidic aqueous solution followed by catalytic hydrogenation (Pd catalyst) gave 5-methylpentadecanoic acid (5).

Embodiment 2

[0133] 7-methyltridecanoic acid

[0134] See General Method I. Hexyl bromide (compound (1), R=CH 3 (CH 2 ) 5 -) into the Grignard reagent (I, step (a)). To this was added 5-chloro-2-pentanone (Aldrich C6, 2660-3) (I, step (b)). The reaction mixture is reacted with acetic anhydride (I, step (c)) to form the chloroacetate (3). Acetic acid (I, step (d)) is removed by refluxing (3) in a suitable solvent such as benzene to obtain a mixture of chloroalkene isomers (4) (R=CH 3 (CH 2 ) 5 -). Conversion of (4) to the Grignard reagent (I, step (e)) follows standard practice techniques. Treatment of Grignard reagent with ethylene oxide followed by aqueous acidic solution (I, step (h)), hydrogenation with Pd catalyst (I, step (i)), and hydrobromination (I, step (j)). Alkyl bromide (6) (R=CH 3 (CH 2 ) 5 -, y=5) is converted into Grignard reagent (I, step (k)), and treated with carbon dioxide and acidic aqueous solution (I, step (1)) to obtain the product 7-methyltridecanoic ac...

Embodiment 3

[0136] 8-Methylpentadecanoic acid

[0137] See General Method I. Heptyl bromide (compound (1), R=CH 3 (CH 2 ) 6 -) into the Grignard reagent (I, step (a)). To this was added 5-chloro-2-pentanone (Aldrich C6, 2660-3) (I, step (b)). The reaction mixture is reacted with acetic anhydride (I, step (c)) to form the chloroacetate (3). Acetic acid (I, step (d)) is removed by refluxing (3) in a suitable solvent such as benzene to obtain a mixture of chloroalkene isomers (4) (R=CH 3 (CH 2 ) 6 -). Conversion of (4) to the Grignard reagent (I, step (e)) follows standard practice techniques. Grignard reagent (I, step (h)), Pd catalyst hydrogenation (I, step (i)), and hydrobromination (I, step (j)) are treated with ethylene oxide followed by aqueous acidic solution. Alkyl bromide (6) (R=CH 3 (CH 2 ) 6 -, y=5) into Grignard reagent (I, step (k)), treated with formaldehyde and water (I, step (m). Formation of alkyl halide (8) by hydrobromination (R=CH 3 (CH 2 )6 -, x=6) (I, ste...

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Abstract

Novel fatty acids and their derivatives, such as salts, novel surfactant systems comprising one or more of these compounds and consumer products containing compounds in said surfactant systems, such as laundry products, personal care products, pharmaceutical compositions , industrial cleaners, etc.

Description

field of invention [0001] The present invention relates to certain novel fatty acids and their derivatives, such as salts, to novel surfactant systems containing one or more of these compounds, and to consumer products comprising said compounds or surfactant systems, such as laundry products, Personal care products, pharmaceutical compositions, industrial cleaners and more. Background of the invention [0002] Fatty acids and soaps have a long history dating back to ancient times. This technique has been highly developed over the last century (see for example "Contemporary Soaps, Candles and Glycerine", L.L. Lanborn, Van Nostrand, New York, 1906). Influential works such as "Industrial Oil and Fat Products", A.E. Bailey, Interscience Press, New York, 1951, and "Fatty Acids", edited by Klare S. Matkley, Parts 1-5, Interscience Press, New York, 1960-1968, which provide a systematic introduction to the technology. Fatty acids are discussed in "Fatty Acids" (ed. E.H. Pryde, Am...

Claims

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Application Information

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IPC IPC(8): C07C53/126C07C53/128C07C69/24C11D1/00C11D1/04C11D1/62C11D1/65C11D1/66C11D3/00C11D3/20C11D3/43C11D9/00C11D9/02C11D17/00
CPCC11D1/62A61Q19/00C11D3/43C11D1/04C11D10/04C11D3/2079A61K8/361C11D1/65C11D3/2093C11D9/007C11D9/005C11D3/0015Y02P20/582
Inventor D·S·康纳J·J·沙伊贝尔D·J·巴克T·特里恩P·K·文森J·C·T·R·布尔科特-斯特·劳伦德M·R·斯维克E·H·沃尔G·M·弗兰肯尼斯H·J·M·德梅耶雷T·A·克里佩M·J·德克莱尔R·G·瑟韦森
Owner THE PROCTER & GAMBLE COMPANY
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