WO2008103136A1 - Alcanolamides de beurre de karité - Google Patents

Alcanolamides de beurre de karité Download PDF

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Publication number
WO2008103136A1
WO2008103136A1 PCT/US2007/004582 US2007004582W WO2008103136A1 WO 2008103136 A1 WO2008103136 A1 WO 2008103136A1 US 2007004582 W US2007004582 W US 2007004582W WO 2008103136 A1 WO2008103136 A1 WO 2008103136A1
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WO
WIPO (PCT)
Prior art keywords
shea butter
alkanolamide
alkanolamides
weight
present
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.)
Ceased
Application number
PCT/US2007/004582
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English (en)
Inventor
Steven Rogers
Anthony O'lenick
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.)
Rutherford Chemicals LLC
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Rutherford Chemicals LLC
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Filing date
Publication date
Application filed by Rutherford Chemicals LLC filed Critical Rutherford Chemicals LLC
Priority to PCT/US2007/004582 priority Critical patent/WO2008103136A1/fr
Publication of WO2008103136A1 publication Critical patent/WO2008103136A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/16—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
    • C07C233/17—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
    • C07C233/18—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton

Definitions

  • the present invention relates to novel alkanolamides prepared by the reaction of an alkanolamine and shea butter, preferably mild-processed shea butter (MPSB).
  • Materials of the present invention are useful as cosmetic and personal care ingredients; they thicken shampoos and body washes, stabilize foam, and deliver to the hair and skin highly desirable active ingredients present in shea butter, including natural antioxidants.
  • alkanolamides perform a variety of functions including viscosity enhancement, foam stabilization, emulsif ⁇ cation and detergency. Specific applications include as humectants and hair detanglers.
  • alkanolamides are the reaction product of an alkanolamine and a fatty material.
  • Fatty materials are a class of compounds which include fatty carboxylic acids, fatty methyl esters and fatty glycerides. Sources of fatty materials include coconut, peanut, soybean, and rapeseed oils, fractionated and non- fractionated fatty methyl esters and fatty acids of carbon chains of varying lengths.
  • Variations in carbon chain lengths of the fatty sources can change the properties of alkanolamides.
  • a finished product having as an ingredient Cs to Cio fatty acids exhibit foam stability, but contribute little as thickeners.
  • Ci 2 to Cj 4 fatty acids are particularly useful as foam boosters; they also show good viscosity building properties.
  • Blending alkanolamides of differing carbon chain lengths can help optimize performance of the finished products in which they are incorporated.
  • Lauric-myristic diethanolamides for example, are common ingredients in formulations of high foaming products such as dishwashing detergent, bubble bath and hair shampoo. They also impart emolliency and conditioning effects to skin and hair, making them among the most commonly used alkanolamides in the personal care industry.
  • Higher molecular weight, unsaturated fatty alkanolamides reduce foam and produce good viscosity build.
  • Illustrative are oleic and linoleic alkanolamides which are excellent viscosity builders at low concentrations. This property makes them particularly useful in surfactant-containing formulations that otherwise are difficult to thicken.
  • Higher molecular weight unsaturated products are known to be oxidatively unstable and can interfere with fragrance in finished products.
  • Shea butter is a butter extracted from the kernel of Butrospermum parkii. This plant, also referred to as Vitellaria paradoxa, is native to Africa.
  • the term butter describes a material that is a solid at room temperature, but melts at about 40 0 C. Chemically, shea butter is a triglyceride conforming to the following structure
  • R a , R b and R c each have one of the following compositions:
  • R b The average composition of R b is different than R n and R 0 , the latter two being similar.
  • the Rb moiety contains predominantly the unsaturated Ci 8 group (oleyl) while R a and R 0 contain predominantly the saturated C is group (stearyl). Differences between internal (Rb) and terminal (R 3 , R 0 ) substitution are seen in natural products but not in synthetic molecules produced in the laboratory.
  • the novel shea butter alkanolamide compounds of the present invention are produced by reacting shea butter, preferably MPSB, with an alkanolamine, preferably under specific mild processing conditions.
  • mild processing is meant processes that do not remove or otherwise diminish the amount or potency of active ingredients, particularly highly desired unsaponifiables.
  • mild processing is employed both at the time of harvesting and initial extraction (creating mild-processed shea butter) and during Rogers; O'Lenick, Jr.
  • shea butter alkanolamides of the present invention thus deliver unexpectedly high amounts of unsaponifiables to the skin and hair in a heretofore unachievable manner. They not only thicken but also act as antioxidants and free radical scavengers. Summary of the Invention
  • the present invention relates to a novel class of alkanolamides made by reacting shea butter with alkanolamines and a process for using them in personal care applications.
  • mild processing is employed both at the time of harvesting and initial extraction (creating mild-processed shea butter) and during subsequent preparation of alkanolamide derivatives.
  • materials containing unexpectedly high amounts of active ingredients, particularly highly desired unsaponifiables, are produced.
  • the compounds of the present invention are alkanolamides produced by reacting shea butter with an alkanolamine.
  • the shea butter is mild-processed and is reacted with an alkanolamine under mild processing conditions.
  • the novel Rogers; O'Lenick, Jr. Shea Butter Alkanolamides Atty. Docket VER-PCT-001 alkanolamides of the present invention are rich in unsaponif ⁇ ables, including antioxidants and free-radical scavengers.
  • Shea butter alkanolamide derivatives of the present invention conform to the following structure:
  • R 1 is derived from shea butter and comprises . from about 0.1 to about 2.0 % by weight C] ⁇ 23 ; from about 0.5 to about 2.0% by weight Ci 3 H 27 ; from about 2.0 to about 6.0% by weight C 15 H 31 ; from about 25 to about 50% by weight Ci 7 H 35 ; and from about 40.0 to about 60.0 % by weight Ci 7 H 33 ;
  • R 2 is selected from the group consisting Of-CH-CH 2 OH,
  • R 3 is selected from the group consisting of -H, -CH 2 CH 2 OH.
  • Shea butter can be prepared by standard extraction techniques known to those of skill in the art.
  • U.S. Patent No. 6,552,208 the disclosure of which is incorporated herein by reference, describes several methods for processing shea butter.
  • Suitable extraction vehicles may include, but are not limited to, ethanol, methanol, ethyl acetate, acetone, chloroform and water, or any other solvent and water.
  • shea butter is mild-processed; it is extracted using a hydrocarbon-free solvent system and its alkanolamide derivatives are Rogers; O'Lenick, Jr. Shea Butter AIkanolamides Atty. Docket VER-PCT-001 made under mild processing conditions.
  • ground-up kernels are boiled in water under mild conditions as described in the examples below.
  • the oil phase is then separated from the water phase by decanting.
  • This process provides a yellow solid wax rich in unsaponifiables.
  • wax is meant a material obtained by boiling in water under ambient conditions, decanted and filtered.
  • the mild processing of the present invention may be contrasted with separation using solvents and high temperature treatment with high pressure steam. While the latter processes result in what some may describe as a "more pure" triglyceride, unsaponifiables, and the benefits derived therefrom, are lost. Vacuum distillation which strips off the desirable components is also to be avoided in processing MPSB of the present invention.
  • Sterols comprise about 20% of the unsaponifiables in shea butter. More particularly, the sterols comprise: cholesterol (from about 1 % to about 3%); alpha- spinasterol (from about 1% to about 4%); delta-7-stigmasterol (from about 40% to about 44%); delta-7-avenasterol (from about 38% to about 41%).
  • the remaining constituents of the unsaponifiables (about 80%) include other highly desirable active compounds including tocopherol, karitin, cinamic acid esters, alpha and beta amyrin and phenolics.
  • Phenolic compounds are natural products composed of one or more aromatic benzene rings with one or more hydroxyl group. They are a class of natural products that possess antioxidant and free radical scavenging properties.
  • phenolics in the unsaponifiables of mild-processed shea butter include gallic acid, gallocatchin, catechin, Rogers; O'Lenick, Jr. Shea Butter Alkanolamides Atty. Docket VER-PCT-001 epigallocatechin gallate, epicatechin, gallocatechin gallate, gallocatechin gallate and quercetin.
  • Alkanolamides of the present invention are made by the amidation reaction of shea butter (or, preferably, MPSB) with an alkanolamine conforming to the following structure:
  • R 2 is selected from the group consisting Of-CH 2 CH 2 OH,
  • R 3 is selected from the group consisting of -H, -CH 2 CH 2 OH.
  • Alkanolamines suitable for use in the present invention are commercially available from a variety of suppliers, including Dow Chemical (Midland, Michigan). Illustrative examples of suitable alkanolamines are listed below:
  • the amidation is conducted at a temperature of from about 80 0 C to about 90 0 C in the presence of an anhydrous alkaline catalyst.
  • Another aspect of the present invention is a process for delivering antioxidants to the skin or hair by topically applying a finished product comprising an effective amount of an alkanolamide made by the amidation reaction of shea butter (or, preferably, MPSB) and an alkanolamine conforming to the following structure:
  • R 2 is selected from the group consisting Of-CH 2 CH 2 OH,
  • R 3 is selected from the group consisting of -H, -CH 2 CH 2 OH.
  • the amidation is conducted at a temperature of from Rogers; O'Lenick, Jr. Shea Butter Alkanolamides Atty. Docket VER-PCT-001 about 80 0 C to about 90°C in the presence of an anhydrous alkaline catalyst. By processing in this temperature range, alkanolamides of the present invention and glycerin remain in the product.
  • Tn contrast when methyl esters or fatty acids are used in preparing alkanolamides, methanol or water, respectively, are distilled off, resulting in the loss of desirable unsaponif ⁇ ables.
  • the lower processing temperatures are also more compatible with, and maintain the potency of, antioxidants present in the unsaponif ⁇ ables.
  • the effective concentration of alkanolamide ranges from about 0.5% to about 15.0% by weight.
  • R 2 is -CH 2 CH 2 OH
  • R 3 is -H
  • R 2 is -CH 2 CH 2 OH
  • R 3 is -CH 2 CH 2 OH
  • R 2 is -CH 2 CH 2 O-CH 2 CH 2 OH
  • R 3 is -H.
  • R 2 is -CH 2 CH(CH 3 )OH
  • R 3 is -H.
  • Mild-processed shea butter is made according to the following procedure:
  • Examples 5 — 8 are illustrative of the MPSB alkanolamides of the present invention.
  • the specified number of grams of alkanolamine (Examples 1-4) is added the specified number of grams of MPSB.
  • This mass is heated to from about 80 0 C to about 90 0 C. Thereafter, about 0.4% by weight of solid sodium methylate powder is added.
  • the mass is held within the specified temperature range for a period of from about four to about six hours. Nothing is distilled off during this time.
  • the amine value drops during this period and, after several hours, stabilizes. Once the amine value stabilizes, the reaction is held an additional hour and the reaction mass is cooled to ambient temperature.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Cosmetics (AREA)

Abstract

L'invention concerne de nouveaux alcanolamides préparés par réaction d'un alcanolamide et de beurre de karité, de préférence de beurre de karité transformé par des techniques douces (MPSB: mild processed shea butter). Ces substances sont utiles en tant qu'ingrédients cosmétiques et de soins personnels. Elles épaississent les shampoings et les produits d'hygiène corporelle, stabilisent la mousse, et permettent de délivrer à la peau et aux cheveux des insaponifiables de haute valeur présents dans le beurre de karité, notamment des anti-oxydants naturels.
PCT/US2007/004582 2007-02-23 2007-02-23 Alcanolamides de beurre de karité Ceased WO2008103136A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
PCT/US2007/004582 WO2008103136A1 (fr) 2007-02-23 2007-02-23 Alcanolamides de beurre de karité

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/US2007/004582 WO2008103136A1 (fr) 2007-02-23 2007-02-23 Alcanolamides de beurre de karité

Publications (1)

Publication Number Publication Date
WO2008103136A1 true WO2008103136A1 (fr) 2008-08-28

Family

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Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2007/004582 Ceased WO2008103136A1 (fr) 2007-02-23 2007-02-23 Alcanolamides de beurre de karité

Country Status (1)

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WO (1) WO2008103136A1 (fr)

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5616552A (en) * 1994-06-15 1997-04-01 Ajinomoto Co., Inc. Detergent composition comprising N-acylthreonine salt
US20010044405A1 (en) * 1998-03-11 2001-11-22 Mona Industries, Inc. Alkanolamides
US6514918B1 (en) * 2000-08-18 2003-02-04 Johnson & Johnson Consumer Companies, Inc. Viscous, mild, and effective cleansing compositions

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5616552A (en) * 1994-06-15 1997-04-01 Ajinomoto Co., Inc. Detergent composition comprising N-acylthreonine salt
US20010044405A1 (en) * 1998-03-11 2001-11-22 Mona Industries, Inc. Alkanolamides
US6514918B1 (en) * 2000-08-18 2003-02-04 Johnson & Johnson Consumer Companies, Inc. Viscous, mild, and effective cleansing compositions

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