EP1230003A2 - Procede de production d'agents de fixation organiques et d'agents tensioactifs organiques, produits obtenus par ce procede, et utilisation de ces produits - Google Patents

Procede de production d'agents de fixation organiques et d'agents tensioactifs organiques, produits obtenus par ce procede, et utilisation de ces produits

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Publication number
EP1230003A2
EP1230003A2 EP00931040A EP00931040A EP1230003A2 EP 1230003 A2 EP1230003 A2 EP 1230003A2 EP 00931040 A EP00931040 A EP 00931040A EP 00931040 A EP00931040 A EP 00931040A EP 1230003 A2 EP1230003 A2 EP 1230003A2
Authority
EP
European Patent Office
Prior art keywords
organic
optionally substituted
produced
emulsifier
surfactant
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Withdrawn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
EP00931040A
Other languages
German (de)
English (en)
Inventor
Morten Sloth Weidner
Morten Just Petersen
Tonny Jorgensen
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.)
Astion Development AS
Original Assignee
Astion Development AS
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 Astion Development AS filed Critical Astion Development AS
Publication of EP1230003A2 publication Critical patent/EP1230003A2/fr
Withdrawn legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/0012—Galenical forms characterised by the site of application
    • A61K9/0014—Skin, i.e. galenical aspects of topical compositions
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
    • A—HUMAN NECESSITIES
    • A21—BAKING; EDIBLE DOUGHS
    • A21D—TREATMENT OF FLOUR OR DOUGH FOR BAKING, e.g. BY ADDITION OF MATERIALS; BAKING; BAKERY PRODUCTS
    • A21D2/00—Treatment of flour or dough by adding materials thereto before or during baking
    • A21D2/08—Treatment of flour or dough by adding materials thereto before or during baking by adding organic substances
    • A21D2/14—Organic oxygen compounds
    • A21D2/16—Fatty acid esters
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS OR COOKING OILS
    • A23D7/00—Edible oil or fat compositions containing an aqueous phase, e.g. margarines
    • A23D7/01—Other fatty acid esters, e.g. phosphatides
    • A23D7/013—Spread compositions
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L29/00—Foods or foodstuffs containing additives; Preparation or treatment thereof
    • A23L29/10—Foods or foodstuffs containing additives; Preparation or treatment thereof containing emulsifiers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/04—Dispersions; Emulsions
    • A61K8/06—Emulsions
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/37—Esters of carboxylic acids
    • A61K8/375—Esters of carboxylic acids the alcohol moiety containing more than one hydroxy group
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/55—Phosphorus compounds
    • A61K8/556—Derivatives containing from 2 to 10 oxyalkylene groups
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/10—Washing or bathing preparations
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
    • C09K23/14—Derivatives of phosphoric acid
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
    • C09K23/16—Amines or polyamines
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
    • C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
    • C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
    • C11C3/003—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fatty acids with alcohols
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
    • C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
    • C11C3/02—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fatty acids with glycerol
    • C11C3/025—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fatty acids with glycerol with a stoechiometric excess of glycerol
    • 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
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/02—Anionic compounds
    • C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
    • C11D1/29—Sulfates of polyoxyalkylene ethers
    • 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
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/02—Anionic compounds
    • C11D1/34—Derivatives of acids of phosphorus
    • 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
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/66—Non-ionic compounds
    • C11D1/722—Ethers of polyoxyalkylene glycols having mixed oxyalkylene groups; Polyalkoxylated fatty alcohols or polyalkoxylated alkylaryl alcohols with mixed oxyalkylele groups
    • 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
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/88—Ampholytes; Electroneutral compounds
    • C11D1/90—Betaines
    • 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
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/88—Ampholytes; Electroneutral compounds
    • C11D1/92—Sulfobetaines ; Sulfitobetaines
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
    • A61K47/14—Esters of carboxylic acids, e.g. fatty acid monoglycerides, medium-chain triglycerides, parabens or PEG fatty acid esters
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/20—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing sulfur, e.g. dimethyl sulfoxide [DMSO], docusate, sodium lauryl sulfate or aminosulfonic acids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q1/00—Make-up preparations; Body powders; Preparations for removing make-up
    • A61Q1/02—Preparations containing skin colorants, e.g. pigments
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q1/00—Make-up preparations; Body powders; Preparations for removing make-up
    • A61Q1/02—Preparations containing skin colorants, e.g. pigments
    • A61Q1/04—Preparations containing skin colorants, e.g. pigments for lips
    • A61Q1/06—Lipsticks
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/02—Preparations for cleaning the hair
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/12—Preparations containing hair conditioners

Definitions

  • the present invention relates to a method of producing organic emulsifiers and organic surfactants, to organic emulsifiers and organic surfactants produced by said method, and more specifically to organic cosmetic, organic food, organic pharmaceutical, organic technical and organic detergent compositions containing them as well as the use of organic emulsifiers and organic surfactants produced by said method for the preparation of organic cosmetic, organic food, organic pharmaceutical, organic technical and organic detergent preparations of superior quality.
  • Pesticides include herbicides such as 2,4-Dichlorophenoxyacetic acid, 2,4,5-Trichlorophenoxyacetic acid, Alachlor, Amitrole, Atrazine, Metribuzin and Trifluralin; fungicides such as Benomyl, ethyiene bis dithiocarbamates, hexachlorobenzene and tributyltin compounds; insecticides such as Cabaryl, Malathion, Methomyl, Dicolfol, Meth- oxychlor, Lindane, Beta-Hexachlorocyclohexane, DDT, Chlordane, heptachlor and hepta- chlor epxides, Dieldrin, Mirex, Toxaphene, and nematocides such as Aldicarb and 1,2-Di- bromo-3-chloropropane. 1
  • a number of pesticides have been found to accumulate in nature. Recently, pesticide residues have been found in drinking water in a number of countries. Furthermore it is well established that a broad spectrum of crops and foods derived therefrom contain considerable amounts of pesticides. Also, potential non-food products such as vegetable oils often contain pesticide residues.
  • organic agriculture On the basis of the above-mentioned problems associated with conventional agriculture, a new form of agriculture has evolved, termed organic agriculture.
  • This model of agriculture which is also sometimes called “ecological agriculture” or “biological agriculture”, is in practise free of the use of synthetic pesticides or processed chemical fertilisers.
  • organic agriculture is much more environmentally friendly and provides crops that are free of pesticide residues.
  • Organic agriculture is based on specific and precise standards of production which aim at achieving optimal agro-ecosystems which are socially, ecologically and economically sustainable. Terms such as “biological” and “ecological” are also used in an effort to describe the organic system more clearly. Requirements for organically produced foods differ from those for other agricultural products in that production procedures are an intrinsic part of the identification and labelling of, and claim for, such products. The principles for organic production, specifically for plants and plant products, are described in greater detail in international guidelines as mentioned below.
  • Organic is a labelling term that denotes products which have been produced in accordance with organic production standards and certified by a duly constituted certification body or authority.
  • Organic agriculture is based on minimising the use of external inputs, avoiding the use of synthetic fertilisers and pesticides. Organic agriculture practices cannot ensure that products are completely free of residues, due to general environmental pollution. However, methods are used to minimise pollution of air, soil and water. Organic food handlers, processors and retailers adhere to standards to maintain the integrity of organic agricultural products.
  • the primary goal of organic agriculture is to optimise the health and productivity of interdependent communities of soil, life, plants, animals and people.
  • Organic agriculture is constituted by production management systems which promote and enhance agro-ecosystem health, including biodiversity, biological cycles, and soil biological activity.
  • An organic production system is designed to:
  • An integral component of certification is the inspection of the organic management system. Procedures for operator certification are based primarily on a yearly description of the agricultural enterprise as prepared by the operator in cooperation with the inspection body. Likewise, at the processing level, standards are also developed against which the processing operations and plant conditions can be inspected and verified. Where the inspection process is undertaken by the certification body or authority, there must be a clear separation between the inspection and certification functions. In order to maintain their integrity, certification bodies or authorities which certify the procedures of the operator should be independent of economic interests with regard to the certification of operators.
  • Products will be regarded as bearing indications referring to organic production methods where, in the labelling or claims, including advertising material or commercial documents, the product, or its ingredients, is described by the terms "organic”, “biodynamic”, “biological”, “ecological” or words of similar intent including diminutives which, in the country where the product is put on the market, suggest to the purchaser that the product or its ingredients were obtained according to organic production methods.
  • organically produced foods such as organic vegetables and cereals
  • a production of organic meat derived from animals fed on organic feeds, and organic eggs from fowls fed on organic feeds have also reached the market.
  • more processed organic food products have become available, such as organic bread and organic diary products derived from milk obtained from animals fed on organic feeds.
  • organic production has not provided more advanced processed products.
  • Organic agriculture has evolved as a grass-root movement and basically the principles of organic production have been to keep the products as simple and unprocessed as possible.
  • This current concept of organic products has strongly inhibited the development of more technically advanced organic products, limiting the possibility of a commercial breakthrough for organic products in a broader sense, e.g. organic plant derived chemicals or advanced processed organic additives leading to more advanced organic foods, organic cosmetics, organic pharmaceuticals or organic technical products, such as detergents.
  • the present invention provides a method of producing a number of organic emulsifiers and organic surfactants that are acceptable as components of organic food or organic non-food products.
  • the method of the invention comprises:
  • an organic or organically produced product is defined as a product produced according to any of the above-mentioned principles and guidelines for organic agriculture, or similar guidelines.
  • the product has been certified as such by a relevant authority.
  • This definition covers all organic or organically produced products, including plants, animals or birds or any products or components derived therefrom.
  • the method of the invention and the organic emulsifiers or surfactants obtained by it are novel simply because nobody has ever before thought of combining the principles of organic farming with the advanced knowledge of chemical processing technology.
  • the people involved in organic farming have typically been idealistic and based on grass-root movements, without understanding of advanced industrial processing.
  • the people involved in industrial chemical processing technology have not even considered the possibility of developing products based on organic materials, because they typically have a very limited knowledge of the existence of organic products and because organic agriculture has a low-tech image.
  • the methods and products according to the invention are not only novel, but also in- volve an important inventive step by combining the knowledge and principles of two worlds that are usually not combined, whereby it is possible to dramatically improve the quality and industrial usefulness of organic products and provide the world with some technically satisfying organic cosmetics, organic foods, organic pharmaceuticals, organic technical products, and organic detergents that have never been possible before.
  • the latter is simply because similar non-organic emulsifiers and detergents cannot be employed in an organic finished product, as the finished product would no longer be organic, since it would no longer be based primarily on organic ingredients.
  • organic emulsifiers and organic surfactants according to the invention make it possible to produce much more advanced, professional and attractive organic products, thus giving organic products a much more serious and competitive image, e.g. in the following areas:
  • Organic cosmetics e.g. skin care products, hair care products, creams or lotions (e.g. facial creams, facial day creams, facial night creams, facial protective creams, facial moisturisers, body lotions, cleansing milk etc.), sunscreens, hand soaps or shower soaps (liquid or solid soaps), deodorants, lipsticks, mascaras, liquid foundations, shampoos, "2 in 1" shampoos, dandruff shampoos, conditioners, etc.
  • creams or lotions e.g. facial creams, facial day creams, facial night creams, facial protective creams, facial moisturisers, body lotions, cleansing milk etc.
  • sunscreens e.g. facial creams, facial day creams, facial night creams, facial protective creams, facial moisturisers, body lotions, cleansing milk etc.
  • sunscreens e.g. facial creams, facial day creams, facial night creams, facial protective creams, facial moisturisers, body lotions, cleansing milk etc.
  • sunscreens e.g. facial
  • Organic foods e.g. salad dressings, mayonnaise, sauces, ice cream, candy, spreads, margarines, bakery and confectionery products, coffee whiteners, etc.
  • Organic pharmaceuticals e.g. plant based drugs.
  • Organic technical products e.g. paints, varnishes, shoe polish, printing ink and plastics.
  • Organic detergents such as household cleaners (e.g. hand dishwasher detergents, automatic dishwasher detergents, laundry detergents and laundry aids etc.) and industrial cleaning products.
  • the present invention provides cosmetic, food, pharmaceutical, technical or detergent compositions containing an organic emulsifier or detergent according to the in- vention.
  • the present invention provides the use of the organic emulsifiers or surfactants for preparing an organic cosmetic composition, an organic food composition, an organic pharmaceutical composition, an organic technical composition or an organic detergent composition.
  • the present invention provides a method for producing organic surfactants and organic emulsifiers.
  • Said method consists essentially of the following three steps:
  • organic surfactant(s) and organic emulsifier(s) chemical modification of the refined oil(s) and fat(s) providing organic surfactant(s) and organic emulsifier(s).
  • organic emulsifiers and surfactants with various chemical structures can be produced according to the method of the present invention. The structures of such organic emulsifiers and surfactants are described in the literature, e.g. in Ullmann's Encyclopedia of Industrial Chemistry.
  • Organic surfactants produced according to the method of the present invention include anionic emulsifiers or surfactants of the general formula I, non-ionic emulsifiers or surfactants of the general formula II, and amphoteric emulsifiers or surfactants of the general formula III (see below).
  • the invention comprises anionic surfactants produced by the method of the invention and having the general formula I:
  • R is selected from optionally substituted C 6 . 30 -alkyl, optionally substituted C 6 - 30 - alkenyl, optionally substituted C 6- 3o-alkyl(aryl), and optionally substituted C 6 . 30 -alkoxy;
  • X is (CH 2 -CH 2 -O);
  • Y is SO 2 , and SO 3 ;
  • Z is selected from hydrogen, Na + , K + , 1 Ca ++ , 1 Mg ++ , and NH 4 + ;
  • n O, 1 , 2, 3 or 4.
  • surfactants with the general formula I are salts of alkyl sulphates, alkyl ether sulphates and alkyl sulfosuccinates. Especially preferred are sodium lauryl sulphate and lauryl ether sulphate.
  • the invention comprises non-ionic surfactants produced by the method of the invention and having the general formula II:
  • R 2 -X n -Z m -H II wherein R 2 is selected from optionally substituted C 6 . 3 o-alkyl, optionally substituted C 6-3 o- alkenyl, optionally substituted C 6 . 3 o-alkyl(aryl), optionally substituted C 6 .3o-alkoxy, optionally substituted C 6 - 30 -alkyl(aryloxy), and optionally substituted C 6- 3o-alkylamide;
  • X is (CH 2 -CH 2 -O);
  • Z is (CH 2 -CH(CH 3 )-O).
  • n is 0-60 and m is 0,3-6 with the proviso that n is 0,3-6 when m is 3-6, and n+m > 1.
  • surfactants with the general formula II are polyoxy ethylene fatty acid esters. Especially preferred are polyoxyethylene(8)stearate and polyoxyethylene(40)stearate.
  • the invention also comprises amphoteric surfactants produced by the method of the invention and having the general formula ill:
  • R 3 and R 4 are independently selected from optionally substituted C 1-10 -alkyl, and optionally substituted C 2-10 -alkenyl;
  • R 5 is selected from optionally substituted C 6 . 30 -alkyl, and optionally substituted C 6 - 3 o- aikenyl;
  • X is selected from C ⁇ -3 o-alkyl, oxo, -CH 2 CO 2 " , -(CH 2 ) 3 SO 3 ' , and halogen such as fluorine, chlorine, iodine and bromine.
  • Organic emulsifiers and surfactants produced by the method according to the invention include compounds of the general formula IV:
  • R 6 , Rzor R 8 is independently selected from optionally substituted C 6 3o-alkylcarbonyloxy, and optionally substituted C 6 30 -alkenylcarbonyloxy,
  • R 6 , R or R 8 is independently selected from hydrogen, hydroxy, R'C(O)O-, and R"OP(OH)(O)O-, such as ethanoate, 2-hydroxypropanoate, 3,4-d ⁇ carboxy-3-hydroxybuta- noate, 3-carboxy-2,3-d ⁇ hydroxypropanoate, 3-carboxy-2-acetyloxy-3-hydroxypropanoate, 3-carboxy-3-acetyloxy-2-hydroxypropanoate, 3-carboxy-2,3-d ⁇ acetyloxypropanoate,
  • R 1 is selected from optionally substituted C ⁇ 30 -alkyl, and optionally substituted C 2 30 - alkenyl, such as methyl,
  • R" IS selected from hydrogen, ammonium, d 10 -alkyl, am ⁇ no(C 1 10 -alkyl), mono-, di- and tn(C ! 10 -alkyl)am ⁇ no(C 1 10 -alkyl), such as aminoethyl, trimethylaminoethyl, inositol, and
  • R 6 , R 7 or R 8 independently selected from hydrogen, hydroxyi, optionally substituted C 6 30 -alkylcarbonyloxy, optionally substituted C 6 30 -alkenylcarbonyloxy, and R'C(O)O-
  • emulsifiers with the general formula IV are acetic acid esters of mono- and diglycerides, lactic acid esters of mono- and diglycerides, citric acid esters of mono- and diglycerides and mixed acetylated tarta ⁇ c acid esters of mono- and diglycerides
  • Organic emulsifiers and surfactants according to the invention include phospholipids
  • emulsifiers and surfactants are phosphatidyl cho- hne, phosphatidyl ethanolamine, phosphatidyl senne or phosphatidyl inositol, or lyso- phosphohpids thereof
  • Organic emulsifiers and surfactants according to the invention include fatty acid esters of a mono- or polysacchande or fatty acid esters of the corresponding alcohol of a mono- or polysacchande
  • emulsifiers and surfactants are fatty acid esters of monosaccha ⁇ des selected from the group consisting of trioses, tetroses, pentoses, hex- oses, heptoses and octoses or their corresponding alcohols
  • organic emulsifiers and surfactants produced by the method of the invention include compounds of the general formula V:
  • R 9 , R ⁇ 0 and Rn are independently selected from optionally substituted C 6 - 3 o-alkyl- carbonyl, and optionally substituted C 6 . 30 -alkenylcarbonyl, and hydrogen.
  • emulsifiers with the general formula V are sorbitan fatty acid esters and poly- oxyethylene sorbitan fatty acid esters. Especially preferred are sorbitan monolaurate, sorbitan monopalmitate, sorbitan monooleate, sorbitan monostearate, sorbitan tristearate, polyoxyethylene(20)sorbitan monolaurate, polyoxyethylene(20)sorbitan monooleate, poly- oxyethylene(20)sorbitan monopalmitate, polyoxyethylene(20)sorbitan monostearate and polyoxyethylene(20)sorbitan tristearate.
  • the invention comprises organic emulsifiers and surfactants produced by the method of the invention and having the general formula VI:
  • R 12 , R 13 or R 1 is independently selected from optionally substituted C 6 . 3 o-alkylcarbonyl, and optionally substituted C 6-3 o-alkeny1carbonyl;
  • R ⁇ 2 , R ⁇ 3 and R M are independently selected from hydrogen, optionally substituted C 6 - 3 o-alkylcarbonyloxy, and optionally substituted C 6 - 30 - alkenylcarbonyloxy.
  • emulsifiers with the general formula VI are common sucrose fatty acid esters.
  • only natural chemicals or chemicals derived from an organically produced organism are employed in the production of the organic emusifier or surfactant of the invention.
  • citric acid derived from organically produced lemons or limes may preferably be employed in the production of citric acid esters of monoglycerides.
  • lactic acid derived from organically produced milk may preferably be employed in the production of lactic acid esters of monoglycerides or in the production of stearoyl iactylates.
  • organic emulsifiers and surfactants that can be produced according to the method of the invention, are emulsifiers and surfactants approved for the use in food products, since such emulsifiers are generally harmless to the living organism.
  • Lists of such approved emulsifiers and surfactants can be provided by international authorities, such as the European Commission, the FAO/WHO (Codex), and national authorities, e.g. the United States Food and Drug Administration (see Monographs for Emulsifiers for Foods, 2 nd edition, 1985, European Food Emulsifiers Association).
  • fats and oils are defined as triacylglycerols or fatty acid esters of other carboxylic alcohols, where fats are solid at 20°C and oils are liquid at 20°C.
  • composition means any mixture of chemicals for industrial uses, such as industrial emulsions, lubricants, paints, varnishes, plastics, slipping agents, cooling liq- uids, etc.
  • C ⁇ o-alky means a linear and branched hydrocarbon group having 1 to 30 carbon atoms, such as methyl, ethyl, propyl, /so-propyl, butyl, iso-b - tyl, tert-butyl, pentyl, /so-pentyl, hexyl, /so-hexyl, heptyl, /so-heptyl, octyl, /so-octyl, nonyl, /so-nonyl, decanyl, /so-decanyl, octanyl, decanyl, dodecanyl, tetradecanyl, hexadecanyl, octadecanyl, eicosanyl, docosanyl, tetracosanyl, hexacosanyl, and o
  • C 6 - 3 o-alkyl means a linear and branched hydrocarbon group having 6 to 30 carbon atoms, such as octanyl, decanyl, dodecanyl, tetradecanyl, hexadecanyl, octadecanyl, eicosanyl, docosanyl, tetracosanyl, hexacosanyl, and octacosanyl.
  • C 1-10 -alkyl is intended to cover linear and branched hydrocarbon groups having 1 to 10 carbon atoms, e.g.
  • C ⁇ . 30 -alkyl are methyl, ethyl, propyl, /so-propyl, butyl, tert-butyl, decanyl, dodecanyl, tetradecanyl, hexadecanyl, octadecany, eicosanyl and docosanyl.
  • C 6 Preferred examples of "C 6 .
  • 3 o-alkyl are dodecanyl, tetradecanyl, hexadecanyl, and octadecanyl, and especially preferred examples of "C ⁇ o-alkyl” are methyl, ethyl, propyl, /so-propyl, butyl and tert-butyl.
  • C 2 . 30 -alkenyl covers linear and branched hydrocarbon groups having 2 to 30 carbon atoms and comprising 1 to 15 unsaturated bonds.
  • alkenyl groups are butenyl, pentadieneyl, hexenyl, hexadienyl, hepenyl, heptadienyl, octenyl, octadienyl, nonenyl, nonadienyl, decenyl, decadienyl, decatrienyl, decetetraenyl, dodecenyl, dodecadienyl, dodecatrienyl, dodecetetraenyl, dodecepentaenyl, tetradecenyl, tetradecadienyl, tetradecatrienyl, tetradecetetraenyl, tetradecepentaenyl, tetradecehexaenyl
  • C 6 - 30 -alkenyl covers linear and branched hydrocarbon groups having 6 to 30 carbon atoms and comprising 1 to 15 unsaturated bonds.
  • alkenyl groups are octenyl, octadienyl, decenyl, decadienyl, decatrienyl, decetetraenyl, dodecenyl, dodecadienyl, dodecatrienyl, dodecetetraenyl, dodecepentaenyl, tetradecenyl, tetradecadienyl, tetradecatrienyl, tetradecetetraenyl, tetradecepentaenyl, tetradecehexaenyl, hexadecenyl, hexadecadienyl, hexadecatrienyl, hexadecetetraenyl, hexadecepentaenyl,
  • C 2 - 30 -alkenyl are linear hydrocarbon groups having 1 to 4 unsaturated bonds such as dodecenyl, dodecadienyl, tetradecenyl, tetradecadienyl, tetradecatrienyl, hexadecenyl, hexadecadienyl, hexadecatrienyl, octadecenyl, octadecadienyl, octadecatrienyl, and octadecetetraenyl.
  • C 6 - 3 o-alkenyl are linear hydro- carbon groups having 1 to 5 unsaturated bonds such as dodecenyl, dodecadienyl, tetradecenyl, tetradecadienyl, tetradecatrienyl, hexadecenyl, hexadecadienyl, hexadecatrienyl, octadecenyl, octadecadienyl, octadecatrienyl, and octadecetetraenyl.
  • op- tionally substituted means that the group in question may be substituted one or several times, preferably 1-5 times, with group(s) selected from hydroxy (which when bound to an unsaturated carbon atom may be present in the tautomeric keto form), C 1-10 -alkyl, hydroxy(C 1 . ⁇ o-alkyl), C 1-10 -alkylcarbonyloxy, carboxy, d- 10 -alkoxycarbonyl, C 1-10 -alkoxy, C 2 .
  • ⁇ o-alkenyloxy, oxo (forming a keto or aldehyde functionality), C 1-10 -alkylcarbonyl, formyl, aryl, aryloxycarbonyi, aryloxy, arylcarbonyl, heteroaryl, heteroaryloxycarbonyl, hetero- aryloxy, heteroarylcarbonyl, amino, mono-, di- and tri(C ⁇ .
  • the substituents are selected from hydroxy, d- 10 -alkyl, hydroxy(C 1 _ 10 -alkyl), d- ⁇ o-alkylcarbonyloxy, carboxy, C 1-10 -alkoxycarbonyl, d. 6 -alkoxy, d- 6 -alkoxycarbonyl, d- 6 -alkylcarbonyl, formyl, aryl, aryloxycarbonyi, arylcarbonyl, heteroaryl, amino, mono- and di(d-6-alkyl)amino, carbamoyl, mono- and di(C 1 .
  • aryl means a fully or partially aromatic carbocyclic ring or ring system, such as phenyl, naphthyl, 1 ,2,3,4-tetrahydronaphthyl, anthracyl, phenanthra- cyl, pyrenyl, benzopyrenyl, fluorenyl and xanthenyl, among which phenyl is a preferred ex- ample.
  • heteroaryl groups examples include oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyrrolyl, imidazolyl, pyrazolyl, pyridinyl, pyrazinyl, pyridazinyl, piperidinyl, coumaryl, furyl, quinolyl, benzothiazolyl, benzotriazolyl, benzodiazolyl, benzooxozolyl, phthalazinyl, phthalanyl, triazolyl, tetrazolyl, isoquinolyl, acridinyl, carbazolyl, dibenzazepinyl, indolyl, benzopyrazolyl, and phenoxazonyl.
  • the term “optionally substituted” means that the group in question may be substituted one or several times, preferably 1-5 times, in particular 1-3 times, with group(s) selected from hydroxy (which when present in an enol system may be represented in the tautomeric keto form), C 1-6 -alkyl, d. 6 -alkoxy, oxo (which may be represented in the tautomeric enol form), carboxy, d. 6 -alkoxycarbonyl, d.
  • Halogen includes fluoro, chloro, bromo, and iodo.
  • the first step in the method of the invention comprises isolating an organic oil or fat from an organic source.
  • the organic source may be any living organism produced organically.
  • an organic or organically produced living organism is defined as an organism produced according to any of the above- mentioned principles and guidelines for organic agriculture and farming, or similar guidelines, the product preferably being certified as being organic by a relevant authority.
  • the organically produced organism is a plant. Any organically produced plant may be used and any part of the plant may be employed as a source of the oil or fat. Such parts may for example be fruits, flowers, leaves, stems, wood (from trees), bark, roots, cell cultures, tissue cultures, etc.
  • oils and fats such as: babassu oil, boleko oil, borneo tallow, castor oil, cereal oils, cocoa butter, coconut oil, corn (maize) oil, cottonseed oil, grape seed oil, hazelnut oil, hemp seed oil, illipe fat, kapok oil, kenaf seed oil, linseed oil, lupine 5 oil, mowrah fat, mustard seed oil, neou oil, niger seed oil, oiticica oil, okra oil, olive oil, palm oil, paimkernel oil, parinarium oil, peanut oil, perilla oil, poppy seed oil, pumpkin seed oil, rapeseed oil, safflower oil, sesame oil, shea butter, soybean oil, sunflower oil, teaseed oil, tung oil, vernonia oil, walnut oil, etc.
  • oils and fats such as: babassu oil, boleko oil, borneo tallow, castor oil, cereal oils, cocoa butter, coconut
  • the isolation of the oil or fat from the plant source generally includes two steps, expelling and solvent extraction.
  • Oilseeds are normally preexpelled to a residual fat content of about 20%, and the expeller cake is then extracted to 1-2% fat. Preexpelling is omitted if the fat content of the seed is
  • Coarse materials such as copra are first broken by passage through interlocking rolls. 30 Fluted rolls are used for nearly all other seeds. Smooth or so-called flaking rolls are used to complete seed comminution.
  • the comminuted seed is conditioned prior to expelling by moistening and heating in suitable equipment.
  • lipoproteins decompose, proteins coagulate, and 35 intracellular oil bodies coalesce.
  • the cell walls themselves are not macerated during conditioning. Coagulation of protein facilitates expelling and subsequent percolation in the extractor.
  • Undesirable enzymes and microorganisms are deactivated at temperatures above 80°C and in the presence of sufficient moisture.
  • Expelling separates the oil from the solid phase, the so-called expeller cake, and can be carried out in continuous or batch presses.
  • the expeller oil still contains so-called foots which must be removed by filtration.
  • the extraction solvent should dissolve only glycerides but not undesirable compo- nents such as coloring matter and gums.
  • the solvents must not contain toxic components, and should be recoverable with minimum loss, be safe in handling, and be readily removable from the extracted material.
  • aliphatic hydrocarbons especially pentane, hexane or heptane, are preferred.
  • Technical hexane with a boiling point range of 55-70°C has proved to be optimal. Hexane can be readily removed from the oil at temperatures below 100°C in vacuo and can be stripped from the meal with steam. The solubility of hexane in the condensed water is only 0.1%.
  • Chlorinated hydrocarbons such as trichloroethylene and dichloromethane are of interest because of their high extraction capacity but are not preferred because of the potential toxicity risk from residual solvent. Processes in which the oil is displaced by hot water are also an option.
  • Oilseeds can preferably be extracted in a counter-current process: pure solvent is contacted with material that has already been largely extracted, and the oil-rich solution is contacted with non-extracted material. Such extractions can be performed either continuously or in a batch process.
  • a more environmentally friendly extraction procedure could be based on catalytic enzymes, such as cellulases, liberating the fatty contents of the plant cells.
  • catalytic enzymes such as cellulases
  • fractionation methods could subsequently be applied, e.g. centrifugation to obtain a purified oil or fat fraction.
  • An enzymatically based process would be ideal for processing of plant cell cultures.
  • Production of plant cells in tanks according to the principles of organic production could be a convenient production method, especially in the case of labile fats and oils.
  • the organically produced organism is an animal.
  • any organically produced animal may be employed as a source of the fat or oil, for example small or large land animals, fish, birds or reptiles.
  • the source of the fat or oil may be any part of the organically produced animal, including eggs or milk.
  • oils and fats such as: land animal oils and fats, e.g. beef tal- low, chicken fat, goat fat, goose fat, horse fat, lard, mutton tallow, etc.; marine oils and fats, e.g. cod oil, halibut oil, herring oil, menhaden oil, etc.
  • Animal fats can be readily isolated from tissue by heating since the cell membranes of animal cells are much weaker than those of plant cells. The intraceliular fat expands on heating and disrupts the membrane. Extraction with solvents is limited to offal. Fatty tissue is particularly susceptible to decomposition so that rapid processing is necessary if refrigeration is not possible. Microbial and autolytic degradation rapidly leads to oxidation, hydrolysis, colour deterioration, and unpleasant odours and flavours, which are difficult to remove from the fat. The free fatty acid content therefore serves as a convenient, primary quality criterion.
  • Fish oils are generally isolated by rendering. Crushed fish (herring, menhaden, sardines, pilchards) with a dry matter content of 15-22% is first cooked in closed vessels at relatively low pressure. This operation sterilises the fish and coagulates the protein to produce a fish mass that can be easily pressed. Subsequent screw pressing separates most of the water and oil from the press cake.
  • the press water is pre-purified over screens or with a decanter (desiudger) and then separated by centrifugation into crude fish oil and stickwater (or glue water).
  • the press cake (about 50% water) is dried and sometimes also extracted with a solvent. Eventually a process employing liquefied propane as the extraction solvent can be utilised. Such a method can also be used to fractionate fish liver oils.
  • the organically produced organism is a microorganism.
  • Any organically produced microorganism may be employed as a source of the oil or fat.
  • Such microorganisms may for example be bacteria, yeast, fungi, algae, etc. Extraction of the fat or oil fraction from such microorganisms follows basic extraction principles some of which are mentioned above.
  • the preferred extraction solvents are organic solvents that are water-immiscible, e.g. pentane, hexane, heptane, ethyl acetate, n-butanol or higher alcohols.
  • a more environmentally friendly extraction procedure would be based on catalytic enzymes, liberating the fatty contents of the microorganisms.
  • several frac- tionation methods could be applied, e.g. centrifugation to obtain a purified oil or fat fraction.
  • the second step in the method of the invention comprises refining the isolated organic oil or fat. This step is optional in the sense that it is not always required, since some crude oils may be suitable for chemical modification without refinement.
  • the aim of the refinement step is to prepare the organic oil or fat for the chemical modification necessary to produce the organic emulsifiers or surfactants according to the invention.
  • Refinement of the isolated organic oil or fat is an optional step before the chemical modification by which the organic emulsifier or surfactant according to the invention is produced.
  • Crude oils and fats obtained by expelling, extraction, or rendering contain trace components that are undesirable for stability and further processing. These substances include seed particles, dirt, phosphatides, carbohydrates, proteins, trace metals, pigments, waxes, oxidation products of fatty acids, and toxic components such as polycyclic aromatic hydrocarbons, gossypol, mycotoxins, sulfur compounds (in fish and cruciferous oils).
  • the aim of refining the oils and fats according to the invention is to remove these undesirable components as much as possible without significantly affecting the concentration of desirable constituents such as polyunsaturated fatty acids, and without significant loss of the major glyceride components. Refining usually involves the following steps:
  • the last step in the method according to the present invention comprises chemical modification of the refined organic oils and fats to produce organic emulsifiers or surfactants, e.g. with the general formulae I, II, III, IV, V, and VI.
  • chemical modification comprises one or more chemical reactions performed on the optionally refined organic oils and fats, and includes all reactions which can be applied to refined oils and fats.
  • the obtained chemically modified oils and fats can be further modified using chemical reactions such as oxidation, reduction, salt formation, aliphatic nucleophilic substitution, aromatic electrophilic substitution, aliphatic electrophilic substitution, aromatic nucleophilic substitution, free-radical substitution, addition to carbon-carbon multiple bonds, addition to carbon-hetero multiple bonds, elimination, rearrangements and polymerization.
  • chemical reactions such as oxidation, reduction, salt formation, aliphatic nucleophilic substitution, aromatic electrophilic substitution, aliphatic electrophilic substitution, aromatic nucleophilic substitution, free-radical substitution, addition to carbon-carbon multiple bonds, addition to carbon-hetero multiple bonds, elimination, rearrangements and polymerization.
  • the products obtained by the above-mentioned chemical reactions can be subjected to further chemical reactions.
  • organic emulsifiers and surfactants according to the invention have numerous applications, within the fields of organic cosmetic compositions, organic food compositions, organic pharmaceutical compositions, organic technical compositions and organic detergent compositions.
  • the products resulting from substituting the conventional emulsifiers and surfactants (produced from non-organic sources) with organic emulsifiers and surfactants are true organic end-products wherein all ingredients originating from possible organic sources are produced organically.
  • the following are typical non-limiting examples of applications within these areas.
  • An organic skin care product according to the present invention may typically be produced by mixing an oil phase consisting of iipophilic emulsifiers according to the invention and emollients, with an aqueous phase consisting of water and water soluble compounds, typically at elevated temperatures.
  • the emollient is an organically produced oil or fat, or an organic ester produced according to the invention.
  • the organic skin care product contains a preservative to prevent microbial growth.
  • the preservative is organically produced, e.g. a surface active organic preservative produced according to the present invention, such as glyceryl mono capryiate.
  • a fragrance is optionally added.
  • the fragrance is an organically produced essential plant oil.
  • Typical non-limiting examples of products in this category include creams such as facial creams, facial day creams, facial night creams, facial protective creams and facial moisturisers etc; lotions such as body lotions and cleansing milk etc; sunscreens, soaps such as liquid hand soaps, solid hand soaps, liquid shower soaps and solid shower soaps; deodorants such as deodorant roll-ons and deodorant sticks; lipsticks; mascaras; liquid foundations and cleansers.
  • creams such as facial creams, facial day creams, facial night creams, facial protective creams and facial moisturisers etc
  • lotions such as body lotions and cleansing milk etc
  • sunscreens soaps such as liquid hand soaps, solid hand soaps, liquid shower soaps and solid shower soaps
  • deodorants such as deodorant roll-ons and deodorant sticks
  • lipsticks mascaras
  • liquid foundations and cleansers liquid foundations and cleansers.
  • emulsifiers/surfactants that may be produced according to the present invention are sodium stearoyl lactylate, glycol stearate, glycol palmitate, glycerol stearate, glycerol palmitate, glycerol oleate, sucrose cocoate, sorbitan stearate, stearyl citrate.
  • emollients/thickeners that may be produced according to the present invention are monoglycerides, diglycerides, trigiycerides (long-chain, medium- chain, and short-chain), stearyl alcohol, cetyi alcohol, isopropyl isostearate, stearic acid, isobutyl palmitate, isocetyl stearate, oieyl alcohol, isopropyl laurate, hexyl laurate, decyl oleate, octadecan-2-ol, isocetyl alcohol, cetyi palmitate, isopropyl myristate, isopropyl palmitate, isopropyl stearate, butyl stearate, butyl myristate, isostearic acid, palmitic acid, isopropyl linoleate, lauryl lactate, isostearyl isostearate, myristyl lactate
  • An organic hair care product according to the invention may typically consist of an organic anionic surfactant, an organic amphoteric surfactant, an organic cationic surfactant, and/or an organic foaming agent. Furthermore, the product may contain water, dyes, perfume, pH-regulators, NaCI and preservatives. Typically, a one-pot manufacturing procedure is employed, where all the ingredients are mixed one at a time.
  • the preservative is organically produced, e.g. a surface active organic preservative produced according to the present invention, such as glyceryl mono capryiate.
  • the fragrance is an organically produced essential plant oil.
  • Typical non-limiting examples of products in this category include shampoos, "2 in 1" shampoos, dandruff shampoos, conditioners, etc.
  • organic anionic surfactants that may be produced according to the present invention are sodium lauryl sulphate, ammonium lauryl sulphate, magnesium lauryl sulphate, triethylamine lauryl sulphate, monoethylamine lauryl sulphate, sodium laureth sulphate, ammonium laureth sulphate, magnesium laureth sulphate, tri- methylamine laureth sulphate, monoethylamine laureth sulphate, sodium myreth sulphate, ammonium myreth sulphate, magnesium myreth sulphate, TEA myreth sulphate, MEA myreth sulphate, sulphosuccinates, alkyl phosphates, etc.
  • organic amphoteric surfactants that may be produced according to the present invention are cocamidopropyl betaine, cocoamphocarboxylglycinate, cocobetaine, etc.
  • Typical non-limiting examples of cationic surfactants that may be produced according to the present invention are cetyi trimethyl ammonium chloride, cetyi trimethyl ammonium bromide, distearyl dimethyl ammonium chloride, benzyl dimethyl stearyl ammonium chloride, guar hydroxy propyl trimethylammonium chloride, etc.
  • Hair care products according to the invention may also contain a fragrance, and preferably, the fragrance is an organically produced essential plant oil.
  • Organic colour products according to the invention include, but are not limited to, lip products, mascara, foundations, concealers and tinted moisturisers.
  • Such products can be categorised by their viscosity at room temperature. Some have a very high viscosity e.g. lip sticks, concealers and mascara, while others have a lower viscosity e.g. liquid foundations and tinted moisturisers. These products often consist of various waxes, emollients, emulsifiers and pigments. Preferred pigments are iron oxide and plant derived colourants, preferably derived from organically produced plants.
  • organic emollients and emulsifiers used in the production of these products according to the present invention are, cetyi alcohol, stearoyl alcohol, oleyl alcohol, octacosanol, hexacosanol, isopropyl myristate, decyl oleate, cetyi palmitate, isocetyl stearate, stearoyl stearate, etc.
  • such products with a high viscosity typically may also contain natural waxes preferably organically produced, e.g. carnauba wax, candelilla wax, ceresine wax, beeswax, etc.
  • colour cosmetics according to the invention may also contain a fragrance and preferably, the fragrance is an organically produced essential plant oil.
  • organic washing powders according to the invention may be produced by combining organic surfactants according to the invention with other active ingredients.
  • organic surfactants usually comprise 5 to 90 % w/w and preferably 5 to 60 % w/w of the formulation.
  • Other optional ingredients are water-softening agents and builders (usually 5 to 30 % w/w of the formulation), enzymes (usually below 2 % w/w of the formulation) and eventually bleaching agents (usually below 1 % w/w of the formulation).
  • the organic surfactant ingredients can be non-ionic, anionic, cationic or amphoteric and is responsible for the washing-activity.
  • Water softening-agents and builders are added to washing powders to improve the cleansing action, and to prevent precipitation of magnesium, calcium and iron salts. Usually, mixtures of two or more of the following compounds are used as water softening agents and builders: Sodium citrate, phosphates, zeolites, sodium carbonate and silicates. Enzymes are sometimes added to washing powders to de- grade fats, proteins and polysaccharides, and generally one or more of the following types are used: Upases, amylases, cellulases, and proteases. Bleaching agents can be silicates, "optical white,” or active oxygen compounds e.g. perborates.
  • organic washing powders according to the invention may also contain a fra- grance and preferably, the fragrance is an organically produced essential plant oil.
  • the method of the invention it is thus possible to produce a washing powder, where all or most ingredients are derived from organically produced plants.
  • Such products generally comprise an organic surfactant or emulsifiers according to the invention either alone or in combination with various other ingredients.
  • the organic surfactant ingredients can be non-ionic, anionic, cationic or amphoteric.
  • Typical non-limiting examples of products in this category include hand dishwasher detergents, automatic dishwasher detergents, laundry detergents and laundry aids etc.
  • Non-limiting examples of other optional ingredients are: water, water-softening agents, enzymes and fragrances as mentioned above.
  • Food preparations contain ingredients of dietary value, just like pharmaceuticals contain ingredients of therapeutic value. Furthermore, such products often contain emulsifiers or surfactants to obtain an acceptable product formulation.
  • Organic food and pharmaceutical preparations according to the invention are produced by employing organic emulsifiers and surfactants in combination with the primary dietary or therapeutic ingredient and preferably these dietary or therapeutic ingredients are produced organically.
  • Typical non-limiting examples of such organic foods according to the invention are: dairy products, sauces, spreads, margarines, coffee whiteners, salad dressing, mayonnaise, bakery and confectionery products e.g. bread, meat products, ice cream, candy, chewing gum, etc.
  • organic pharmaceutical products are tablets, capsules, lozenges, chewing gum, fluids, granulates, sprays (e.g. aerosol), inhalants, ointments, gels, liniments, emulsions (e.g. cream or lotion), etc.
  • Oil palms (Elaeis guineensis) are grown in Malaysia according to the principles of organic production. Thus no pesticides or chemical fertilisers are employed in the production and the highest degree of caution is taken not to disturb the surrounding environment. Further- more the production is certified as organic by an authorised European organic certification institution.
  • the fruits contain 35-60% oil, depending on the moisture content.
  • the fresh palm fruits contain very active fat-splitting enzymes (lipases) which must be deactivated as quickly as possible prior to isolating the oil. Since lipases are particularly active in damaged fruits, the whole fruit bunches are sterilised by heating with live steam in autoclaves to deactivate the enzymes and loosen the fruit from the bunches.
  • lipases fat-splitting enzymes
  • the sterilised fruit bunches are threshed in a rotary drum stripper consisting of longitudinal channel bars; the fruit falls through whereas the empty bunch stem is retained in the drum.
  • the separated, sterilised fruits are then converted into an oily mash by a mechanical stirring process known as digestion.
  • the digested fruit mass is passed through screw presses, and the liquor from the press is clarified by static settling or by using decanter centrifuges.
  • the oil is then treated with citric acid and bleaching earth to remove foreign matter and traces of copper and iron compounds. Finally the oil is neutralised by distillation at a temperature of up to 270°C and at a pressure of 0.5-0.8 kPa (5-8 mbar).
  • the oil is hydrolyzed by boiling the oil in 6 M NaOH (1 :2 W/W) for four hours.
  • the mixture is diluted by addition of an equal amount of water.
  • Concentrated hydrochloric acid is slowly added until the mixture is weakly acidic and then the mixture is cooled to room temperature.
  • the fatty acid (mixture of primarily stearic acid and palmitic acid), which is referred to as stearic acid in the following, is isolated by filtration and recrystallized from methanol.
  • Glyceryl monostearate is produced by direct esterification. Three equivalents of glycerol are mixed with one equivalent of stearic acid and 1% (W/W) concentrated sulfuric acid is added. The mixture is heated at 150°C for four hours. Water produced by the reaction is allowed to escape from the reactor. The mixture is slowly cooled to room temperature. Glyceryl monostearate precipitates and is isolated by filtration.
  • Olive trees (Olea europaea) are grown in Greece according to the principles of organic production. Thus no pesticides or chemical fertilisers are employed in the production of the olives and the highest degree of caution is taken not to disturb the surrounding environment. Furthermore the production is certified as organic by an authorised European organic certification institution.
  • the quality of the obtained olive oil depends on the ripeness of the olives, the type of har- vesting (picking, shaking), intermediate storage, and type of processing. Olives contain 38-58% oil and up to 60% water. The ripe olives are processed as quickly as possible since lipases in the pulp cause rapid hydrolysis of the oil, impairing its quality. The mashed pulp is separated in a horizontal decanter and the crude oil is recentrifuged after addition of wash water and thereby clarified.
  • the oil is treated with citric acid and bleaching earth to remove foreign matter. Subsequently the oil is neutralised by distillation.
  • the oil is hydrolyzed by boiling the oil in 6 M NaOH (1:2 W/W) for four hours.
  • the mixture is diluted by addition of an equal amount of water.
  • Concentrated hydrochloric acid is slowly added until the mixture is weakly acidic and then the mixture is cooled to room temperature.
  • the fatty acid (primarily oleic acid) is isolated by filtration and recrystallized from methanol.
  • Sorbitan monooleate is prepared by mixing equimolar amounts of sorbitol and oleic acid and heating the mixture at 225°C for two hours.
  • Sodium hydroxide (0.3% W/W) is used to catalyze the reaction.
  • the reaction is performed under nitrogen, but the water produced from the reaction is allowed to escape from the reactor.
  • Oil palms (Elaeis guineensis) are grown in Malaysia according to the principles of organic production. Thus no pesticides or chemical fertilisers are employed in the production and the highest degree of caution is taken not to disturb the surrounding environment. Further- more the production is certified as organic by an authorised European organic certification institution.
  • the fruits contain 35-60% oil, depending on the moisture content.
  • the fresh palm fruits contain very active fat-splitting enzymes (lipases) which must be deactivated as quickly as possible prior to isolating the oil. Since lipases are particularly active in damaged fruits, the whole fruit bunches are sterilised by heating with live steam in autoclaves to deactivate the enzymes and loosen the fruit from the bunches.
  • lipases fat-splitting enzymes
  • the sterilised fruit bunches are threshed in a rotary drum stripper consisting of longitudinal channel bars; the fruit falls through whereas the empty bunch stem is retained in the drum.
  • the separated, sterilised fruits are then converted into an oily mash by a mechanical stirring process known as digestion.
  • the digested fruit mass is passed through screw presses, and the liquor from the press is clarified by static settling or by using decanter centrifuges.
  • the oil is then treated with citric acid and bleaching earth to remove foreign matter and traces of copper and iron compounds. Finally the oil is neutralised by distillation at a temperature of up to 270°C and at a pressure of 0.5-0.8 kPa (5-8 mbar).
  • the oil is hydrolyzed by boiling the oil in 6 M NaOH (1 :2 W/W) for four hours.
  • the mixture is diluted by addition of an equal amount of water.
  • Concentrated hydrochloric acid is slowly added until the mixture is weakly acidic and then the mixture is cooled to room temperature.
  • the fatty acid (mixture of primarily stearic acid and palmitic acid), which is referred to as stearic acid in the following, is isolated by filtration and recrystallized from methanol.
  • Lactic acid lactate is prepared by heating lactic acid at 120°C for 10 hours.
  • One equivalent of stearic acid, 1.2 equivalents of lactic acid lactate and A equivalent of sodium carbonate are mixed and heated at 200°C for 1.5 hours.
  • the reaction is performed under nitrogen, but the water produced from the reaction is allowed to escape from the reactor. No further purification is necessary.
  • Oil palms (Elaeis guineensis) are grown in Malaysia according to the principles of organic production. Thus no pesticides or chemical fertilisers are employed in the production and the highest degree of caution is taken not to disturb the surrounding environment. Furthermore the production is certified as organic by an authorised European organic certification institution.
  • the fruits contain 35-60% oil, depending on the moisture content.
  • the fresh palm fruits contain very active fat-splitting enzymes (lipases) which must be deactivated as quickly as possible prior to isolating the oil. Since lipases are particularly active in damaged fruits, the whole fruit bunches are sterilised by heating with live steam in autoclaves to deactivate the enzymes and loosen the fruit from the bunches.
  • lipases fat-splitting enzymes
  • the sterilised fruit bunches are threshed in a rotary drum stripper consisting of longitudinal channel bars; the fruits falls through whereas the empty bunch stem is retained in the drum.
  • the separated, sterilised fruit are then converted into an oily mash by a mechanical stirring process known as digestion.
  • the digested fruit mass is passed through screw presses, and the liquor from the press is clarified by static settling or by using decanter centrifuges.
  • the oil is then treated with citric acid and bleaching earth to remove foreign matter and traces of copper and iron compounds. Finally the oil is neutralised by distillation at a temperature of up to 270°C and at a pressure of 0.5-0.8 kPa (5-8 mbar).
  • the oil is hydrolyzed by boiling the oil in 6 M NaOH (1:2 W/W) for four hours.
  • the mixture is diluted by addition of an equal amount of water.
  • Concentrated hydrochloric acid is slowly added until the mixture is weakly acidic and then the mixture is cooled to room temperature.
  • the fatty acid (mixture of primarily stearic acid and palmitic acid), which is referred to as stearic acid in the following, is isolated by filtration and recrystallized from methanol.
  • Glyceryl monostearate is produced by direct esterification. Three equivalents of glycerol are mixed with one equivalent stearic acid and 1% (W/W) concentrated sulfuric acid is added. The mixture is heated at 150°C for four hours. Water produced by the reaction is allowed to escape from the reactor. The mixture is slowly cooled to room temperature. Glyceryl monostearate precipitates and is isolated by filtration.
  • An organic facial cream according to the invention is prepared according to the following formula.
  • the ingredients of A are mixed and heated to 70°C.
  • the ingredients of B are mixed and heated to 70°C.
  • B is mixed into A under constant stirring. The mixture is allowed to cool. At 45°C C is added and the formulation is cooled to room temperature.
  • An organic facial night cream according to the invention is prepared according to the following formula.
  • the ingredients of A are mixed and heated to 70°C.
  • the ingredients of B are mixed and heated to 70°C.
  • B is mixed into A under constant stirring. The mixture is allowed to cool. At 45°C C is added and the formulation is cooled to room temperature.
  • An organic facial moisturiser according to the invention is prepared according to the following formula.
  • the ingredients of A are mixed and heated to 70°C.
  • the ingredients of B are mixed and heated to 70°C.
  • B is mixed into A under constant stirring. The mixture is allowed to cool. At 45°C C is added and the formulation is cooled to room temperature.
  • An organic moisturising liquid hand soap according to the invention is prepared according to the following formula.
  • the ingredients of A are mixed and heated to 70°C.
  • the ingredients of B are added during cooling starting at 35°C, with mixing in between.
  • An organic facial day cream according to the invention is prepared according to the following formula.
  • the ingredients of A are mixed and heated to 70°C.
  • the ingredients of B are mixed and heated to 70°C.
  • B is mixed into A under constant stirring. The mixture is allowed to cool. At 45°C C is added and the formulation is cooled to room temperature.
  • An organic general purpose cleansing milk according to the invention is prepared accord- ing to the following formula.
  • the ingredients of A are mixed and heated to 70°C.
  • the ingredients of B are mixed and heated to 70°C.
  • A is mixed into B under constant stirring. The mixture is allowed to cool. At 45°C C is added and the formulation is cooled to room temperature.
  • An organic facial protective cream according to the invention is prepared according to the following formula.
  • Example 11 The ingredients of A are mixed and heated to 70°C.
  • the ingredients of B are mixed and heated to 70°C.
  • B is mixed into A under constant stirring. The mixture is allowed to cool. At 45°C C is added and the formulation is cooled to room temperature.
  • An organic shampoo according to the invention is prepared according to the following formula.
  • the ingredients are dissolved in water one at a time in the written order. A little heat is applied during mixing.
  • An organic "2 in 1" shampoo according to the invention is prepared according to the following formula.
  • An organic Special Care Shampoo according to the invention is prepared according to the following formula.
  • the ingredients are dissolved in water one at a time in the written order. A little heat is applied during mixing.
  • An organic conditioner according to the invention is prepared according to the following formula.
  • the ingredients of A are mixed and heated to 70°C. B is heated to 70°C. B is added to A under stirring. The emulsion is allowed to cool and at 40°C C is added. Cooling is com- pleted.
  • a typical organic lip stick according to the invention is prepared according to the following formula.
  • a typical organic mascara according to the invention is prepared according to the following formula.
  • the waxes are melted and the other ingredients added before filling.
  • Example 17 A typical organic liquid foundation according to the invention is prepared according to the following formula.
  • the ingredients of A are mixed (without triethanoiamine) and heated to 75°C
  • the ingredients of B are mixed and heated to 75°C B is added to A, triethanoiamine is added and stirred until smooth and homogenous C and D is added
  • An organic washing powder according to the invention is prepared according to the following formula
  • the ingredients are mixed in water to obtain a slurry paste After spraydrying the product has the following composition
  • Distearyldimethyl ammoniumchlo ⁇ de produced according to the method of the inven • Zeolite 9 2 % (w/w)
  • An organic washing powder according to the invention is prepared according to the following formula.
  • the ingredients are mixed in water to obtain a slurry paste. After spraydrying the product has the following composition:
  • An organic washing powder according to the invention is prepared according to the following formula.
  • the ingredients are mixed in water to obtain a slurry paste. After spraydrying the product has the following composition:
  • An organic washing-up liquid according to the invention is prepared according to the following formula.
  • the ingredients are slowly added to the water and stirring is continued until a clear homogenous solution is obtained.
  • the product has the following composition:
  • Example 22 An organic washing-up liquid according to the invention is prepared according to the following formula.
  • the ingredients are slowly added to the water and stirring is continued until a clear homogenous solution is obtained.
  • the product has the following composition:
  • n-dodecylbenzene sulphonate produced according to the method of the invention: 29.5 % (w/w).
  • An organic washing-up liquid according to the invention is prepared according to the following formula.
  • the ingredients are slowly added to the water and stirring is continued until a clear homogenous solution is obtained.
  • the product has the following composition: • n-dodecylbenzene sulphonate (produced according to the method of the invention): 20.0 % (w/w).
  • Sucrose monolactylate produced according to the method of the invention: 5.0 % (w/w).
  • Glyceryl monocaprylate preservative, produced according to the method of the invention: 0.5 % (w/w).
  • Water 74.5 % (w/w).
  • An organic household detergent according to the invention is prepared according to the following formula.
  • the ingredients are slowly added to the water, and stirring is continued until a clear homogenous solution is obtained.
  • the product has the following composition:
  • n-dodecylbenzene sulphonate produced according to the method of the invention: 15.0 % (w/w).
  • n-stearyl sulfonate produced according to the method of the invention: 5.0 % (w/w).
  • Distearyldimethyl ammoniumchloride produced according to the method of the invention: 2.0 % (w/w).
  • Glyceryl monocaprylate serving, produced according to the method of the invention: 0.5 % (w/w).
  • Example 25 An organic household detergent according to the invention is prepared according to the following formula.
  • the ingredients are slowly added to the water and stirring is continued until a clear homogenous solution is obtained.
  • the product has the following composition: • Sodium lauryl ether sulphate (produced according to the method of the invention): 10.0 % (w/w).
  • Distearyldimethyl ammoniumchloride produced according to the method of the invention: 2.0 % (w/w).
  • Sucrose monolactylate produced according to the method of the invention: 10.0 % (w/w).
  • Glyceryl monocaprylate (preservative, produced according to the method of the inven- tion): 0.5 % (w/w).
  • An organic household detergent according to the invention is prepared according to the following formula.
  • the ingredients are slowly added to the water and stirring is continued until a clear homogenous solution is obtained.
  • the product has the following composition:
  • Distearyldimethyl ammoniumchloride produced according to the method of the invention: 2.0 % (w/w).
  • Glyceryl monocaprylate (preservative, produced according to the method of the inven- tion): 0.5 % (w/w).
  • Washing powder for automatic dishwasher is a washing powder for automatic dishwasher
  • Washing powders for automatic dishwasher is produced according to the method of the invention, as shown in the following non-limiting examples:
  • An organic washing powder (for automatic dishwashers) according to the invention is prepared according to the following formula.
  • the ingredients are mixed in water to obtain a slurry paste. After spraydrying the product has the following composition: • Sodium lauryl ether sulphate (produced according to the method of the invention): 37.3 % (w/w).
  • An organic washing powder (for automatic dishwashers) according to the invention is prepared according to the following formula.
  • the ingredients are mixed in water to obtain a slurry paste. After spraydrying the product has the following composition:
  • Distearyldimethyl ammoniumchloride produced according to the method of the invention: 10.4 % (w/w).
  • Example 29 An organic washing powder (for automatic dishwashers) according to the invention is prepared according to the following formula. The ingredients are mixed in water to obtain a slurry paste. After spraydrying the product has the following composition:
  • n-stearyl sulfonate produced according to the method of the invention: 9.9 % (w/w).

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  • Pharmacology & Pharmacy (AREA)
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Abstract

La présente invention concerne un procédé de production d'agents de fixation organiques et d'agents tensioactifs organiques, des agents de fixation organiques et des agents tensioactifs organiques produits par ce procédé. Cette production consiste à utiliser dans la préparation des agents précités de l'huile ou des matières grasses issues de sources biologiques, par exemple de plantes organiques ou d'animaux . Lorsque ces agents de fixation ou ces tensioactifs sont utilisés pour obtenir des produits finis biologiques, tels que des produits cosmétiques biologiques, des aliments biologiques, des produits pharmaceutiques biologiques, des compositions de détergents et de produits techniques biologiques, ces produits finis sont complètement biologiques. Parmi les produits biologiques de cette invention citons des produits cosmétiques biologiques, des aliments biologiques, des produits pharmaceutiques biologiques, des compositions de détergents et de produits techniques biologiques de qualité supérieure.
EP00931040A 1999-06-01 2000-05-30 Procede de production d'agents de fixation organiques et d'agents tensioactifs organiques, produits obtenus par ce procede, et utilisation de ces produits Withdrawn EP1230003A2 (fr)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
DKPA199900773 1999-06-01
DK990773 1999-06-01
US13973699P 1999-06-18 1999-06-18
US139736P 1999-06-18
PCT/DK2000/000293 WO2000072953A2 (fr) 1999-06-01 2000-05-30 Procede de production d'agents de fixation organiques et d'agents tensioactifs organiques, produits obtenus par ce procede, et utilisation de ces produits

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EP1230003A2 true EP1230003A2 (fr) 2002-08-14

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EP (1) EP1230003A2 (fr)
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Cited By (1)

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WO2013087735A1 (fr) 2011-12-12 2013-06-20 Aktsiaselts Toidu Ja Fermentatsioonitehnoloogia Arenduskeskus Dispositif et procédé pour traiter une matière première

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BRPI0702541A2 (pt) * 2007-06-21 2009-02-10 Petroleo Brasileiro Sa processo de craqueamento catalÍtico para produÇço de diesel a partir de sementes de oleaginosas
US9579618B2 (en) 2015-06-17 2017-02-28 Christos Ritzoulis Emulsifiers from grape processing by-products
CN107376654A (zh) * 2017-08-25 2017-11-24 安徽智博新材料科技有限公司 一种复方中药提取液澄清用微滤膜清洗剂
CN111050571A (zh) * 2018-03-16 2020-04-21 陶氏环球技术有限责任公司 泡沫控制
CN114364776A (zh) * 2019-09-02 2022-04-15 联合利华知识产权控股有限公司 洗涤剂组合物

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WO2013087735A1 (fr) 2011-12-12 2013-06-20 Aktsiaselts Toidu Ja Fermentatsioonitehnoloogia Arenduskeskus Dispositif et procédé pour traiter une matière première

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WO2000072953A2 (fr) 2000-12-07

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