US2114490A - Emulsion - Google Patents

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US2114490A
US2114490A US165901A US16590137A US2114490A US 2114490 A US2114490 A US 2114490A US 165901 A US165901 A US 165901A US 16590137 A US16590137 A US 16590137A US 2114490 A US2114490 A US 2114490A
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hydrophillic
water
oleaginous
lipins
oil
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US165901A
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Benjamin R Harris
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    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS, 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
    • A23D7/011—Compositions other than spreads

Definitions

  • My invention relates to water-oil emulsions and processes of producing the same.
  • the present invention is a continuation in part of my prior application Serial No. 709,022, filed January 30,
  • oleomargarine which is essentially an emulsion of oils and fats and water with finely subdivided clotted casein as the emulsify'ing agent
  • vanishing cream which is stearlc acid emulsified with potassium or sodium soap in water
  • cold creams which are essentially emulsions of oleaginous materials with soap and water
  • certain types of furniture polishes which likewise are emulsions of various kinds of oils, among them mineral oil and turpentine and water or other aqueous liquid with a suitable emulsifying agent
  • bread doughs and cake batters etc.
  • emulsions are generally made of vegetable, animal and/or mineral oils and fats, depending upon the nature of the emulsion, which are for all practical purposes immiscible with water and/or aqueous liquids.
  • substances of a class which I term hydrophillic lipins, however, and which contain free OH groups such emulsions are stabilized by the emulsifying action of the hydrophillic lipin and greatly improved results are obtained.
  • One of the principal objects of my invention is to stabilize emulsions of this general character.
  • emulsions of the general character described above, as well as other emulsions comprising oleaginous and fatty materials and water or aqueous liquids may be appreciably improved by the introduction of a proportion of certain types of materials, which I designate as hydrophillic lipins and which are described in V
  • the oleaginous substance may be entirely replaced by hydrophillic lipins.
  • my hydrophilliclipins and the oleaginous substances 55 used heretofore in water and oil emulsions are distinctly immiscible with water, are not readily wetted by water to any appreciable extent and do not show the aflinity for water which characterize, in part, my hydrophillic lipins.
  • the hydrophillic properties of my lipins manifest themselves by capacity, in varying degrees, to imbibe water, to be wetted by water and to foam or froth with water. It is common knowledge to those skilled in the art that the fats and oils heretofore used are, generally speaking, notably deficient in this capacity.
  • my hydrophillic lipins are characterized by the presence ofa group of moderately high molecular weight, say, from about six car- 20 bons up, and of predominantly oleaginous or hydrocarbon characteristics, which imparts the strictly oleaginous character to a portion of the hydrophillic lipin molecule and another group, or association of groups, with at least one unesterified hydroxy group attached to carbon and with distinctly hydrophillic characteristics; that is, a group which imparts to the molecule as a whole a certain degree of affinity for water and aqueous media not possessed by the oleaginous materials such as linseed oil, lard, petrolatum, soya bean oil, etc., heretofore used in water and oil emul-' sions.
  • a group of moderately high molecular weight say, from about six car- 20 bons up
  • oleaginous or hydrocarbon characteristics which imparts the strictly oleaginous character to a portion of the hydrophillic lipin molecule and another group,
  • hydrophillic lipins which are of value are:
  • Mono-olelc acid ester of sucrose 2. Mono-lauric acid ester of dextrose 3. Mono-stearic acid ester of fructose 4. Mono-stearic acid ester of mannitol v 5. Coconut oil mixed fatty acid mono-esters ofmaltose 6. Di-palmitic acid ester of sucrose '7. Mono-ricinoleic acid ester of levulose 8. Mono-lauric acid ester of sorbitol 9. Di-caproic acid ester of maltose l0. Mono-lauric acid ester of mannitol 11. Mono-oleic acid ester of mannitol l2.
  • Mono-oleic acid ester of sorbitol I may employ various sugars and sugar alcohols as polyhydroxy substances, which may be partially esterifled with higher aliphatic or fatty acids to produce the hydrophilliclipins which I employ in accordance with the principles of my invention.
  • sugars include the monosaccharides, di-
  • saccharldes trisaccharides and the like among which are specifically sucrose, dextrose, galactose,
  • lactose maltose, mannose, levulose, xylose, arabinose, rhamnose and rafhnose.
  • sugar alcohols are mannitol, sorbitol, dulcitol, arabitol and the like.
  • the higher molecular weight aliphatic and fatty acids with which the sugars and sugar alcohols are partially esterified include the following: caproic acid, caprylic acid, capric acid, saturated and unsaturated higher aliphatic acids such as the higher fatty acids containing preferably from twelve to eighteen carbon atoms and including stearic acid, oleic acid, ricinoleic acid,
  • naphthenic acid and hydroaromatic acids such as abietic acid and the like.
  • the lard may be advantageously replaced by 200 grams of mono-oleic acid ester of sucrose.
  • saponification of the stearic acid with the ammonia is carried out first, after which the lipin is introduced; in other respects, the usual procedure for making a face cream of this type may be followed.
  • Another example of my invention may be carried out in the manufacture of vanishing cream as follows:
  • monostearyl glucose is more hydrophillic and a better emulsifying agent than distearyl glucose
  • hydrophillic lipins are limited to the particular substances specifically named in this specification by way of example.
  • Other organic water-soluble polyhydroxy substances may be used, in which one or more than one hydroxyl is converted into an ester group with a high molecular weight fatty acid or derivative thereof having at least six carbon atoms, and preferably twelve to eighteen carbon atoms, there being at least one and preferably several free or unesterlfied hydroxyl groups attached to the polyhydroxy nucleus.
  • my hydrophillic lipins may also be used for the manufacture of furniture polishes, mineral oil, turpentine and water emulsions and other ole-' aginous emulsions containing animal and vegetable fats and oils such as corn oil, cottonseed oil, marine oils, tung oil, oleo oil, beef stearine, lard, soy bean oil, linseed oil, and mineral oils such as liquid parafiin, kerosene, petrolatum, and oleaginous substances such as turpentine, etc.
  • animal and vegetable fats and oils such as corn oil, cottonseed oil, marine oils, tung oil, oleo oil, beef stearine, lard, soy bean oil, linseed oil, and mineral oils such as liquid parafiin, kerosene, petrolatum, and oleaginous substances such as turpentine, etc.
  • the propor tions of the hydrophillic lipins employed in the emulsions are variable, this depending upon the exactnature of the emulsiomthe potency of the particular hydrophillic lipin selected, and the specific results desired.
  • the proportions may range from a fraction of 1% to at least several percent. For example, from about V41 to about 5% based on the weight of. the emulsion as a whole, is usually satisfactory.
  • An emulsion comprising oleaginous material, aqueous material and a hydrophillic lipin of a class consisting of higher fatty acid esters of sugars and war alcohols, said lipins containing at least one unesterified sugar or sugar alcohol y I P- 2.
  • An emulsion comprising oleaginous mate rial, aqueous material, and a proportion of a higher molecular weight aliphatic acid ester of the class of sugar alcohols consisting of mannitol and sorbitol, said ester containing at least one free sugar alcoholhydroxy. group.
  • An emulsion comprising oleaginous material, aqueous material, and a proportion of a higher molecular weight fatty acid ester of the 5.
  • a cosmetic emulsion containing oleaginousmaterial, aqueous material and a hydrophillic lipin of a class consisting of higher fatty acid esters of sugars and sugar alcohols, said lipins oontaining at least one unesterified'sugar or sugar alcohol hydroxy group.
  • An emulsion comprising oleaginous material, aqueous material, alkaline material, and a hydrophillic lipin of a class consisting of higher molecular aliphatic acid esters of the class consisting of sugars and sugar alcohols, said lipins containing at least one unesterified sugar or sugar alcohol hydroxy group.

Description

, 50 greater detail hereinafter.
Patented Apr. 19, 1938 UNITED STATES PATENT o1=1=1c1z Benjamin ar:i :hicago, 111.
No Drawing. Application September 2'7, 1987,
Serial No. 165,901
11 Claims.
My invention relates to water-oil emulsions and processes of producing the same. The present invention is a continuation in part of my prior application Serial No. 709,022, filed January 30,
1934, which, in turn, is a division of nrv prior application Serial No. 431,964, filed February 27, 1930, which has issued as Patent No. 2,109,842. In the art of making water-in-oil emulsions and oil-ln-water emulsions, it is customary to bring the ingredients into intimate contact with each other by shaking, agitating, beating, homogenizing, grinding, working in a colloid mill or using some other means for the purpose of subdividing the disperse phase in intimate contact with the continuous phase, and, generally speaking, in the presence of a. suitable emulsifying agent.
Some of the better known emulsions of this kind are, for example, oleomargarine, which is essentially an emulsion of oils and fats and water with finely subdivided clotted casein as the emulsify'ing agent; vanishing cream, which is stearlc acid emulsified with potassium or sodium soap in water; cold creams which are essentially emulsions of oleaginous materials with soap and water; certain types of furniture polishes, which likewise are emulsions of various kinds of oils, among them mineral oil and turpentine and water or other aqueous liquid with a suitable emulsifying agent; bread doughs and cake batters, etc.
The above emulsions are generally made of vegetable, animal and/or mineral oils and fats, depending upon the nature of the emulsion, which are for all practical purposes immiscible with water and/or aqueous liquids. By the addition of substances of a class which I term hydrophillic lipins, however, and which contain free OH groups, such emulsions are stabilized by the emulsifying action of the hydrophillic lipin and greatly improved results are obtained.
- One of the principal objects of my invention is to stabilize emulsions of this general character. I have found that emulsions of the general character described above, as well as other emulsions comprising oleaginous and fatty materials and water or aqueous liquids, may be appreciably improved by the introduction of a proportion of certain types of materials, which I designate as hydrophillic lipins and which are described in V In certain cases, if desired, the oleaginous substance may be entirely replaced by hydrophillic lipins.
One of the principal differences between my hydrophilliclipins and the oleaginous substances 55 used heretofore in water and oil emulsions is that my substances have a more or less marked affinity for water and aqueous liquids, whereas, the oleaginous substances used heretofore, such as corn oil, cottonseed oil, various marine oils, linseed oil, tung oil, oleo oil, beef stearlne, turpentine, liquid 5 paraflln, etc., are distinctly immiscible with water, are not readily wetted by water to any appreciable extent and do not show the aflinity for water which characterize, in part, my hydrophillic lipins.
Generally speaking, the hydrophillic properties of my lipins manifest themselves by capacity, in varying degrees, to imbibe water, to be wetted by water and to foam or froth with water. It is common knowledge to those skilled in the art that the fats and oils heretofore used are, generally speaking, notably deficient in this capacity.
In general, my hydrophillic lipins are characterized by the presence ofa group of moderately high molecular weight, say, from about six car- 20 bons up, and of predominantly oleaginous or hydrocarbon characteristics, which imparts the strictly oleaginous character to a portion of the hydrophillic lipin molecule and another group, or association of groups, with at least one unesterified hydroxy group attached to carbon and with distinctly hydrophillic characteristics; that is, a group which imparts to the molecule as a whole a certain degree of affinity for water and aqueous media not possessed by the oleaginous materials such as linseed oil, lard, petrolatum, soya bean oil, etc., heretofore used in water and oil emul-' sions.
Among the hydrophillic lipins which are of value are:
l. Mono-olelc acid ester of sucrose 2. Mono-lauric acid ester of dextrose 3. Mono-stearic acid ester of fructose 4. Mono-stearic acid ester of mannitol v 5. Coconut oil mixed fatty acid mono-esters ofmaltose 6. Di-palmitic acid ester of sucrose '7. Mono-ricinoleic acid ester of levulose 8. Mono-lauric acid ester of sorbitol 9. Di-caproic acid ester of maltose l0. Mono-lauric acid ester of mannitol 11. Mono-oleic acid ester of mannitol l2. Mono-oleic acid ester of sorbitol I may employ various sugars and sugar alcohols as polyhydroxy substances, which may be partially esterifled with higher aliphatic or fatty acids to produce the hydrophilliclipins which I employ in accordance with the principles of my invention. These sugars include the monosaccharides, di-
saccharldes, trisaccharides and the like among which are specifically sucrose, dextrose, galactose,
lactose, maltose, mannose, levulose, xylose, arabinose, rhamnose and rafhnose. Among the sugar alcohols are mannitol, sorbitol, dulcitol, arabitol and the like.
The higher molecular weight aliphatic and fatty acids with which the sugars and sugar alcohols are partially esterified include the following: caproic acid, caprylic acid, capric acid, saturated and unsaturated higher aliphatic acids such as the higher fatty acids containing preferably from twelve to eighteen carbon atoms and including stearic acid, oleic acid, ricinoleic acid,
naphthenic acid and hydroaromatic acids such as abietic acid and the like.
In cosmetic cream formulae where lanolin is used, it is possible in some cases to entirely replace and in most cases, to partially substitute my hydrophillic lipins for said lanolin and the same is true in cosmetic formulae where beeswax is normally employed.
In cosmetic cold cream formulae, which contain I a proportion of white vaseline or oils or fats, a part of the fatty ingredient may be substituted with the hydrophillic lipin to give desirable results. Thus, for example, in. the following formula:
Stearic acid grams Lard dn Ammonia water (sp. gr. 0.880);
cubic centimeters- Distilled water do Scent The lard may be advantageously replaced by 200 grams of mono-oleic acid ester of sucrose. When this change is made, the saponification of the stearic acid with the ammonia is carried out first, after which the lipin is introduced; in other respects, the usual procedure for making a face cream of this type may be followed.
Another example of my invention may be carried out in the manufacture of vanishing cream as follows:
Grams 1500 300 Rosewater Glycerine Stearic acid Potassium hydroxide 12 Monostearic acid ester of fructose 80 The ingredients, exclusive of the lipins, are warmed to saponlfy the stearic acid and agitated together in the usual order and manner by means of a suitable stirring apparatus. Finally, while still warm, the hydrophillic lipin is added to the mixture with stirring. -A suitable amount of coloring and scent material may be added; other ingredients also may be added, such as starch, zinc oxide, and other medicaments.
It will seem that one outstanding characteristic of the constitutional structure of my hydrophillic lipins is that the fatty character of the otherwise oleaginous molecule is partly offset and attenuated by the presence of hydrophillic hydrou groups attached to carbon.
I have found that the degree of the attenuation of the oleaginous characteristics is by no means, the same in different hydrophillic lipins,
' but varies, first, with the number and character of the free hydroxyl groups present, and, second, with the mass and character of the oleaginous group or groups. Thus, for example, monostearyl glucose is more hydrophillic and a better emulsifying agent than distearyl glucose,
in view of the fact that the former has four free hydroxy groups, whereas the latter has only three free hydroxy groups.
It is by no means to be understood that my hydrophillic lipins are limited to the particular substances specifically named in this specification by way of example. Other organic water-soluble polyhydroxy substances may be used, in which one or more than one hydroxyl is converted into an ester group with a high molecular weight fatty acid or derivative thereof having at least six carbon atoms, and preferably twelve to eighteen carbon atoms, there being at least one and preferably several free or unesterlfied hydroxyl groups attached to the polyhydroxy nucleus.
Besides themanufacture of cosmetic creams, my hydrophillic lipins may also be used for the manufacture of furniture polishes, mineral oil, turpentine and water emulsions and other ole-' aginous emulsions containing animal and vegetable fats and oils such as corn oil, cottonseed oil, marine oils, tung oil, oleo oil, beef stearine, lard, soy bean oil, linseed oil, and mineral oils such as liquid parafiin, kerosene, petrolatum, and oleaginous substances such as turpentine, etc.
It will,0f course, be appreciated that the propor tions of the hydrophillic lipins employed in the emulsions are variable, this depending upon the exactnature of the emulsiomthe potency of the particular hydrophillic lipin selected, and the specific results desired. In general, the proportions may range from a fraction of 1% to at least several percent. For example, from about V41 to about 5% based on the weight of. the emulsion as a whole, is usually satisfactory.
Wherever the term "higher" or higher molecular weight" is employed herein, it will be understoodtomeanatleastaixcarbon atomsunles otherwise specifically stated.
What I claim as new and desire to protect by Letters Patent of the United States is:
1. An emulsion comprising oleaginous material, aqueous material and a hydrophillic lipin of a class consisting of higher fatty acid esters of sugars and war alcohols, said lipins containing at least one unesterified sugar or sugar alcohol y I P- 2. An emulsion comprising oleaginous mate rial, aqueous material, and a proportion of a higher molecular weight aliphatic acid ester of the class of sugar alcohols consisting of mannitol and sorbitol, said ester containing at least one free sugar alcoholhydroxy. group.
3. An emulsion comprising oleaginous material, aqueous material, and a proportion of a higher molecular weight fatty acid ester of the 5. A cosmetic emulsion containing oleaginousmaterial, aqueous material and a hydrophillic lipin of a class consisting of higher fatty acid esters of sugars and sugar alcohols, said lipins oontaining at least one unesterified'sugar or sugar alcohol hydroxy group.
6. A cosmetic emulsion containing oleaginous material, aqueous material, and a proportion of a 8. A cosmetic emulsion containing oleaginous material, aqueous material, and a proportion of a higher molecular weight fatty acid ester of a sugar alcohol of the class consisting of mannitol and sorbitol, said ester containing at least one free sugar alcohol hydroxy group.
9. An emulsion comprising oleaginous material, aqueous material, alkaline material, and a hydrophillic lipin of a class consisting of higher molecular aliphatic acid esters of the class consisting of sugars and sugar alcohols, said lipins containing at least one unesterified sugar or sugar alcohol hydroxy group.
10. A cosmetic emulsion containing oleaginous material, aqueous material, soap, and a hydrophillic lipin of a class consisting of higher fatty acid esters of sugars and sugar alcohols, said lipins containing at least one unesterified sugar or sugar alcohol hydroxy group.
11. A cosmetic emulsion containing oleaginous material, aqueous material, soap, and a proportion of a higher molecular weight aliphatic acid ester of the class of sugar alcohols consisting of mannitol and sorbitol, said ester containing at 20 least one free sugar alcohol hydroxy group.
BENJAMIN R. HARRIS.
US165901A 1937-09-27 1937-09-27 Emulsion Expired - Lifetime US2114490A (en)

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Cited By (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2776268A (en) * 1952-10-18 1957-01-01 Best Foods Inc Leather paste polish containing wax and a monoglyceride
US3516833A (en) * 1963-01-26 1970-06-23 Agfa Ag Photographic material containing a hydrophilic colloid and a sucrose ester
USB370706I5 (en) * 1970-06-17 1975-01-28
US3867301A (en) * 1971-09-11 1975-02-18 Dai Ichi Kogyo Seiyaku Co Ltd Detergent compositions
US3914458A (en) * 1972-07-21 1975-10-21 Asahi Denka Kogyo Kk Edible water in oil emulsion and method for preparing the same
US3919430A (en) * 1974-01-28 1975-11-11 Akzona Inc Water absorption base
US3926840A (en) * 1972-08-21 1975-12-16 Henkel & Cie Gmbh Emulsifiers of water-in-oil creams
US3939290A (en) * 1972-07-21 1976-02-17 Asahi Denka Kogyo Kabushiki Kaisha Water in oil emulsion
US4254105A (en) * 1975-10-11 1981-03-03 The Lion Dentifrice Co., Ltd. Multiple emulsion having a form of water/oil/water phase and process for preparation thereof, and multiple emulsion type cosmetics
US4379755A (en) * 1978-08-10 1983-04-12 Nihon Surfactant Industry Co., Ltd. Gelatinizing agent composition, and gel and aqueous emulsion prepared therefrom
US4826702A (en) * 1986-06-17 1989-05-02 Q.P. Corporation separate type dressing
US20090176876A1 (en) * 2008-01-04 2009-07-09 Jr Chem, Llc Compositions, kits and regimens for the treatment of skin, especially decolletage
US7687650B2 (en) 2006-02-03 2010-03-30 Jr Chem, Llc Chemical compositions and methods of making them
US7867522B2 (en) 2006-09-28 2011-01-11 Jr Chem, Llc Method of wound/burn healing using copper-zinc compositions
US7897800B2 (en) 2006-02-03 2011-03-01 Jr Chem, Llc Chemical compositions and methods of making them
US7927614B2 (en) 2006-02-03 2011-04-19 Jr Chem, Llc Anti-aging treatment using copper and zinc compositions
US8952057B2 (en) 2011-01-11 2015-02-10 Jr Chem, Llc Compositions for anorectal use and methods for treating anorectal disorders
EP2172263A4 (en) * 2007-07-02 2015-08-05 Nisshin Oillio Group Ltd W/o/w emulsion composition
US9427397B2 (en) 2009-01-23 2016-08-30 Obagi Medical Products, Inc. Rosacea treatments and kits for performing them

Cited By (23)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2776268A (en) * 1952-10-18 1957-01-01 Best Foods Inc Leather paste polish containing wax and a monoglyceride
US3516833A (en) * 1963-01-26 1970-06-23 Agfa Ag Photographic material containing a hydrophilic colloid and a sucrose ester
USB370706I5 (en) * 1970-06-17 1975-01-28
US3925242A (en) * 1970-06-17 1975-12-09 Rhone Poulenc Sa Process for reducing foaming of liquids susceptible to foaming
US3867301A (en) * 1971-09-11 1975-02-18 Dai Ichi Kogyo Seiyaku Co Ltd Detergent compositions
US3914458A (en) * 1972-07-21 1975-10-21 Asahi Denka Kogyo Kk Edible water in oil emulsion and method for preparing the same
US3939290A (en) * 1972-07-21 1976-02-17 Asahi Denka Kogyo Kabushiki Kaisha Water in oil emulsion
US3926840A (en) * 1972-08-21 1975-12-16 Henkel & Cie Gmbh Emulsifiers of water-in-oil creams
US3919430A (en) * 1974-01-28 1975-11-11 Akzona Inc Water absorption base
US4254105A (en) * 1975-10-11 1981-03-03 The Lion Dentifrice Co., Ltd. Multiple emulsion having a form of water/oil/water phase and process for preparation thereof, and multiple emulsion type cosmetics
US4379755A (en) * 1978-08-10 1983-04-12 Nihon Surfactant Industry Co., Ltd. Gelatinizing agent composition, and gel and aqueous emulsion prepared therefrom
US4826702A (en) * 1986-06-17 1989-05-02 Q.P. Corporation separate type dressing
US7687650B2 (en) 2006-02-03 2010-03-30 Jr Chem, Llc Chemical compositions and methods of making them
US7897800B2 (en) 2006-02-03 2011-03-01 Jr Chem, Llc Chemical compositions and methods of making them
US7927614B2 (en) 2006-02-03 2011-04-19 Jr Chem, Llc Anti-aging treatment using copper and zinc compositions
US8148563B2 (en) 2006-02-03 2012-04-03 Jr Chem, Llc Chemical compositions and methods of making them
US7867522B2 (en) 2006-09-28 2011-01-11 Jr Chem, Llc Method of wound/burn healing using copper-zinc compositions
EP2172263A4 (en) * 2007-07-02 2015-08-05 Nisshin Oillio Group Ltd W/o/w emulsion composition
US20090176876A1 (en) * 2008-01-04 2009-07-09 Jr Chem, Llc Compositions, kits and regimens for the treatment of skin, especially decolletage
US8273791B2 (en) 2008-01-04 2012-09-25 Jr Chem, Llc Compositions, kits and regimens for the treatment of skin, especially décolletage
US8505730B2 (en) 2008-01-04 2013-08-13 Jr Chem, Llc Compositions, kits and regimens for the treatment of skin, especially décolletage
US9427397B2 (en) 2009-01-23 2016-08-30 Obagi Medical Products, Inc. Rosacea treatments and kits for performing them
US8952057B2 (en) 2011-01-11 2015-02-10 Jr Chem, Llc Compositions for anorectal use and methods for treating anorectal disorders

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