CA1334458C

CA1334458C - Process for forming low-viscosity emulsions of polar oils in water

Info

Publication number: CA1334458C
Application number: CA000601353A
Authority: CA
Inventors: Fred Schambil; Gert-Lothar Striepling; Holger Tesmann
Original assignee: Henkel AG and Co KGaA
Current assignee: Henkel AG and Co KGaA
Priority date: 1988-06-06
Filing date: 1989-05-31
Publication date: 1995-02-14
Anticipated expiration: 2012-02-14
Also published as: DE58901763D1; DE3819193A1; EP0345586A1; WO1989011907A1; JPH03504685A; ES2033489T3; EP0419505A1; EP0345586B1; ATE77761T1

Abstract

Low-viscosity oil-in-water emulsions of oils that are at least 50 % by weight monoesters and diesters containing at least 10 carbon atoms and may also contain up to 50% by weight of aliphatic acid triglycerides and/or up to 25% by weight of hydrocarbon oils may be prepared by emulsification with 0.1 to 0.5 part by weight - per part by weight of the oil component - of an emulsifier having an HLB value of 11 to 12 and, preferably, also with 0.1 to 0.5 part by weight - per part by weight of the oil component - of a co-emulsifier of the saturated aliphatic alcohol or aliphatic acid/polyol partial ester type. The emulsion, which contains at least 1 part by weight of water per part by weight of oil component, is prepared at a temperature above the melting point of the mixture of oil component, emulsifier, and co-emulsifier if used, by a process that includes heating the mixed components to a temperature within or above the phase inversion temperature range, subsequently cooling the emulsion to a temperature below the phase inversion temperature range and, optionally, further diluting the emulsion with water.

Description

PATENT
1 334458 Docket D 7898 IN WATER

Field of the Invention This invention relates to a process for the production of oil-in-water emulsions of polar oil components contain-ing one or more ester functions in the molecule, or of mix-tures of such polar oils with relatively small quantitiesof nonpolar hydrocarbons, under conditions which lead to particularly stable low-viscosity emulsions.
Statement of Related Art It is known that oil-in-water emulsions prepared and stabilized with nonionic emulsifiers undergo phase inver-sion on heating, i.e. the continuous or outer aqueous phase can become the dispersed or inner phase at relatively high temperatures. This process is generally reversible, i.e.
the original emulsion type is reformed again on cooling.
It is also known that the temperature of the phase inversion is dependent on many factors, for example on the type and phase volume fraction of the oil component and on the hydrophilicity and chemical structure of the emulsifier or mixtures of emulsifiers; cf. for example K. Shinoda and H. Kunieda in Encyclopedia of Emulsion Technology, Vol. 1, ed. P. Becher 1983 (M. Decker, N.Y.), pages 337 - 367. It is also known that emulsions prepared at or just below the phase inversion temperature are distinguished by particular fineness and stability while those prepared above the phase inversion temperature are less finely divided (cf. S.
Friberg, C. Solans, J. Colloid Interface Sci., 66, 367 -368 (1978)).
F. Schambil, F. Jost and M. J. Schwuger report in "Progress in Colloid & Polymer Science 73, (1987), 37 - 47 on the properties of cosmetic emulsions containing aliphatic alcohols and aliphatic alcohol polyglycol ethers 1 33445`8 and also state that emulsions prepared above the phase inversion temperature show relatively low viscosity and high stability in storage.
However, the publications cited above are concerned only with emulsions of which the oil phase consists com-pletely or predominantly of nonpolar hydrocarbons. By con-trast, corresponding emulsions in which the oil component consists completely or predominantly of polar esters and triglycerides do not show any phase inversion at temper-atures below 100C, when emulsifiers or emulsifier combinations known for such purposes in the prior art are used.
Accordingly, an object of the present invention is to provide an emulsifier system for completely or pre-dominantly polar oil components which makes it possible to produce emulsions which invert at temperatures below 100C
and which can thus be converted into particularly stable low-viscosity emulsions.
Description of the Invention The present invention comprises a process for the production of low-viscosity oil-in-water emulsions of an oil component (A) which consists of (A.l) 50 to 100% by weight of mono- or di-ester molecules that contain at least 10 carbon atoms and that correspond to one of the formulae (I) R1COOR2, (II) R2ooc-R3-cooR2~ and (III) R1Coo-R3-OOCR1, in which each of R1 and R2 independently represents a C122 alkyl group or C822 alkenyl group, and R3 represents a C216 alkylene group;
and, optionally, (A.2) 0 to 50% by weight of aliphatic acid triglycerides of C8 22 aliphatic acids; and, optionally, (A.3) 0 to 25% by weight of hydrocarbon molecules, characterized in that the oil component (A) and an amount of water having a mass at least equal to the mass of the oil component (A) are made into an emulsion with the aid ~ of 1 334458 0.1 to 0.5 part by weight - per part by weight of the oil component - of a primary emulsifier component (B) having an HLB value of 11 to 12 and consisting of molecules selected from the group of;
(B.l) adducts of ethylene oxide with C1622 aliphatic alcohols and (B.2) adducts of ethylene oxide with partial esters of C36 polyols with C1422 aliphatic acids;
and, preferably, also with the aid of 0.1 to 0.5 part by weight - per part by weight of the oil component -of a co-emulsifier component (C) consisting of molecules selected from the group of:
(C.l) saturated C1622 aliphatic alcohols and (C.2) partial esters of C36 polyols with saturated C1422 aliphatic acids, said emulsion being made at a temperature above the melting point of the mixture of water, oil component (A), emulsifier (B), and co-emulsifier (C) if used, and that the emulsion is heated to, or is prepared at, a temperature within or above the phase inversion temperature range of the mixture, after which the emulsion is cooled to a temperature below the phase inversion temperature range and, optionally, further diluted with water.
Within the compositions defined above and under the working conditions mentioned, emulsions of the polar oil component selected from the monoesters and diesters men-tioned show a phase inversion below 100C, so that particu-larly stable, finely divided, and low-viscosity emulsions can also be prepared with these polar oil components under practical conditions by the described process.
Oil components selected from the monoesters and di-esters of formulae I, II and III are known as cosmetic and pharmaceutical ingredients and also as lubricant compon-ents. Among the monoesters and diesters of this type, those which are liquid at room temperature (20C) are the most important. Monoesters (I) suitable as oil components are, for example, the methyl and isopropyl esters of C1222 aliphatic acids such as, for example, methyl laurate, methyl stearate, methyl oleate, methyl erucate, isopropyl palmitate, isopropyl myristate, isopropyl palmitate, isopropyl stearate, isopropyl oleate. Other suitable monoesters are, for example, n-butyl stearate, n-hexyl laurate, n-decyl oleate, isooctyl stearate, isononyl palmitate, isononyl isononanoate, 2-ethyl hexyl palmitate, 2-ethyl hexyl laurate, 2-hexyl decyl stearate, 2-octyl dodecyl palmitate, oleyl oleate, oleyl erucate, erucyl oleate, and also esters obtainable from technical aliphatic alcohol mixtures and technical aliphatic carboxylic acids, for example esters of saturated and unsaturated C1222 aliphatic alcohols and saturated and unsaturated C1222 aliphatic acids, of the type obtainable from animal and vegetable fats. Naturally occurring monoester and wax ester mixtures, of the type present for example in jojoba oil or in sperm oil, are also suitable.
Suitable dicarboxylic acid esters (II) are, for example, di-n-butyl adipate, di-n-butyl sebacate, di-(2-ethylhexyl)-adipate, di-(2-hexyldecyl)-succinate and diiso-tridecyl azelate. Suitable diol esters (III) are, for example, ethylene glycol dioleate, ethylene glycol diiso-tridecanoate, propylene glycol di-(2-ethylhexanoate), bu-tanediol diisostearate and neopentyl glycol dicaprylate.
Suitable aliphatic acid triglycerides are natural vegetable oils, for example olive oil, sunflower oil, soybean oil, peanut oil, rapeseed oil, almond oil, palm oil, and also the liquid fractions of coconut oil or palm kernel oil, and also animal oils, such as for example neat's foot oil, the liquid fractions of beef tallow, or even synthetic triglycerides of the type obtained by esterification of glycerol with C822 aliphatic acids, for example triglycerides of caprylic acid/capric acid mixtures, triglycerides of technical oleic acid or of palmitic acid/oleic acid mixtures.

- ~ 334458 As stated above, monoesters and diesters and trigly-cerides which are liquid at normal temperature (20C) are preferable as oil components for the process according to the invention, although higher-melting fats and esters corresponding to the above formulae may also be used, preferably in such quantities that the total mixed oil component remains liquid at normal temperature.
The oil component may also contain hydrocarbon oils in quantities of up to at most 25~ by weight, based on the total oil component. Suitable hydrocarbons are, especially, paraffin oils and synthetic hydrocarbons, for example liquid polyolefins, or specific hydrocarbons, for example alkyl cyclohexanes, such as for example 1,3-diisooctyl cyclohexane.
Some nonionic ethylene oxide adducts with C1622 aliphatic alcohols suitable as primary emulsifiers (B) are commercially available. The technical products are mixtures of homologous poly(oxyethylene) ethers of the starting aliphatic alcohols, in which the average degree of ethoxylation corresponds to the molar quantity of ethylene oxide added on per mole of starting alcohol. Other suitable emulsifiers are ethylene oxide adducts with partial esters of any C36 polyol and any C1422 aliphatic acid. Products such as these may be obtained, for example, by ethoxylation of glycerol monostearate, glycerol monopalmitate or of mono- and di-aliphatic acid esters of sorbitan, for example sorbitan monostearate or sorbitan sesquioleate. Emulsifiers suitable for the process according to the invention should have an HLB value of 11 to 12. The HLB (hydrophilic-lipophilic balance) is a value which may be calculated in accordance with the following equation: HLB = (100 - L)/5, in which L is the percent by weight of lipophilic groups, i.e. the aliphatic alkyl or aliphatic acyl groups, in the ethylene oxide adducts.
Preferred emulsifiers are adducts of 8 to 12 moles of ethylene oxide with one mole of saturated C1622 aliphatic alcohols. Adducts of 8 to 12 moles of ethylene oxide with a molar amount of saturated C20-C22 aliphatic alcohol are particularly preferred as emulsifiers for the emulsification in accordance with the invention of oil components which contain no apolar hydrocarbon oils, i.e.
which consist of 50 to 100% by weight monoesters and diesters of formulae I, II and III and O to 50% by weight aliphatic acid triglycerides.
In many cases, a co-emulsifier (C) is preferably used in addition to the primary emulsifier for preparing the oil-in-water emulsions by the process according to the invention. On account of its hydrophilicity, the co-emulsifier is not suitable on its own for the preparation of oil-in-water emulsions, even though particularly stable and finely divided emulsions of the polar oil components may be prepared in conjunction with the use of both types of emulsifiers defined above. According to the invention, suitable co-emulsifiers are those of the saturated C1622 aliphatic alcohol type, for example cetyl alcohol, stearyl alcohol, arachidyl alcohol, behenyl alcohol, or mixtures of these alcohols such as are obtained in the technical hydrogenation of vegetable and animal C16-C22 aliphatic acids or the corresponding aliphatic acid methyl esters. Other suitable co-emulsifiers are partial esters of a C36 polyol and saturated C1422 aliphatic acids. Partial esters such as these are, for example, the monoglycerides of palmitic and/or stearic acid, the sorbitan mono- and/or diesters of myristic acid, palmitic acid, stearic acid, or of mixtures of these aliphatic acids, the monoesters of tri-methylolpropane, erythritol or pentaerythritol and satur-ated C1422 aliphatic acids. Other suitable monoesters are the technical monoesters which are obtained by esterification of 1 mole of polyol with 1 mole of aliphatic acid and which represent a mixture of monoester, diester, and unesterified polyol.
Cetyl alcohol, stearyl alcohol, or a glycerol, sorbi-tan, or trimethylolpropane monoester of a saturated C1422 aliphatic acid, or mixtures thereof, are preferred as co-' 334458 `- emulsifiers for the process according to the invention.
To obtain particularly preferred low-viscosity emulsions with the oil components (A), emulsifiers (B) and co-emulsifiers (C) specified above by the process according to the invention, these components have to be used in relatively closely defined quantitative ratios. A ratio by weight of A to B to C of 1 : 0.1 - 0.3 : 0.1 - 0.3 is preferred, a ratio by weight of A to B to C of l : 0.2 :
0.15 being more preferred.
The process according to the invention may be carried out after initially determining the phase inversion temper-ature, by heating a sample of the emulsion prepared in the usual way at or near room temperature, using a conductivity measuring instrument and determining the temperature at which there is a pronounced reduction in conductivity. The specific conductivity of the oil-in-water emulsion initially present normally decreases from initial values of more than 1 millisiemens per cm (mS/cm) to values below 0.1 mS/cm over a temperature range of 2 to 8C. This temperature range is referred to herein as the phase inversion temperature range.
Once the phase inversion temperature range of the mixture of components needed for a particular emulsion to be made according to this invention is known, the process according to the invention may be carried out either by heating an emulsion initially prepared at a lower temperature to a temperature lying within or above the phase inversion temperature range or by preparing the emulsion at a temperature lying within or above the phase inversion temperature range. After exposure to a temperature within or above the phase inversion temperature range, the mixture is cooled below that temperature range as part of the process of forming the final emulsion.
The oil-in-water emulsions prepared by the process according to the invention are extremely finely divided and stable. It is particularly noticeable that the emulsions prepared in accordance with the invention have a consider-`1 334458 ably lower viscosity than emulsions prepared by the conven-tional process.
Accordingly, it is also possible by the process ac-cording to the invention to produce emulsions of polar oil components of low viscosity and distinctly increased sta-bility which, hitherto, could only be produced from nonpolar hydrocarbons.
Oil-in-water emulsions of the type obtained by the process according to the invention are useful, for example, as skin-care and body-care preparations, as cooling lubri-cants, or as fabric and fiber finishes. The process ac-cording to the invention is particularly useful for the production of emulsion-like preparations for skin and hair treatment purposes. The following Examples are intended to illustrate the invention without limiting it in any way.
EXAMPLES
1. Preparation of the emulsions (general procedure) The oil components, emulsifiers and co-emulsifiers were mixed, heated to a temperature above the melting point of the mixture, and homogenized. The melt was then emulsi-fied while stirring in the water, which had been heated to approximately the same temperature. The compositions of the emulsions are shown in Table I.
2. Determination of the phase inversion temperature Using a conductivity measuring bridge (of a type made by the Radiometer company of Copenhagen), the electrical conductivity of the emulsions was measured as a function of temperature. To this end, each emulsion was initially cooled to +20C. At this temperature, the emulsions showed a conductivity of more than 1 millisiemens per cm (mS/cm), indicating that they were present as oil-in-water emul-sions. A conductivity chart was determined by slowly heating, at a rate of approximately 0.5C/minute under the control of a temperature programmer, a sample of the emulsion contained in a thermally insulated vessel. The temperature range in which the conductivity fell from a value of at least 1 mS/cm to a value below 0.1 mS/cm ~D O
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With all the emulsions shown in Table I, this temperature range was below 100C (See Table II, phase inversion values).

3. Preparation of the emulsions in accordance with the invention The emulsions were prepared as described in 1. and then briefly heated (for about 1 minute) to a temperature in, or slightly above, the phase inversion temperature range. (See Table II, production temperature values.) The emulsions were then rapidly cooled with stirring to room temperature at a cooling rate of approximately 2OC
per minute. After storage for 1 hour at 20C, the viscosity was measured using a rotational viscosimeter (Brookfield type LVT).

4. Comparison Tests For comparison, the emulsions were prepared as des-cribed in part 1, but were heated only to a temperature below the phase inversion temperature range. (See Table II, production temperature values). Cooling was carried out under the same conditions as in part 3.

5. Result The results of processing in accordance with the in-vention and of the Comparison Tests are shown in Table II
for the formulations according to Table I. Processing in accordance with the invention by the process described in part 3 always gave stable, low-viscosity liquid oil-in-water emulsions. By contrast, the Comparison Tests gave oil-in-water emulsions of relatively high viscosity and, in some cases, of relatively low stability.
The embodiments of the invention in which a proprietary or exclusive right is claimed are:

Claims

1. A process for the preparation of an oil-in-water emulsion which inverts at temperatures below 100°C, of an oil component (A) consisting essentially of:
(A.1) 50 to 100% by weight of mono- or di-ester molecules that contain at least 10 carbon atoms and that correspond to one of the formulae R1COOR2, R2OOC-R3-COOR2, and R1COO-R3-OOCR1, in which each of R1 and R2 independently represents a C1-22 alkyl group or C8-22 alkenyl group and R3 represents a C2-16 alkylene group;
(A.2) up to 50% by weight of aliphatic acid triglycerides of C8-22 aliphatic acids; and (A.3) up to 25% by weight of hydrocarbon molecules, said process comprising the steps of:
(I) forming, at a temperature sufficiently high that all components are present in liquid phase, an emulsion consisting essentially of:
a selected quantity of component (A);
a quantity of water having a weight at least equal to the selected quantity of component (A); and (B) about 0.1 to about 0.5 part by weight, per part by weight of component (A), of a primary emulsifier component having an HLB
value of 11 to 12 and consisting of molecules selected from the group consisting of (B.1) adducts of ethylene oxide with C16-22 aliphatic alcohols and (B.2) adducts of ethylene oxide with partial esters between C3-6 polyols and C14-22 aliphatic acids;
(II) exposing the emulsion formed in step (I) to a temperature within its phase inversion temperature range; and (III) cooling the emulsion formed in step (II) below its phase inversion temperature range.

2. A process for the preparation of an oil-in-water emulsion which inverts at temperatures below 100°C, of an oil component (A) consisting essentially of:
(A.1) 50 to 100% by weight of mono- or di-ester molecules that contain at least 10 carbon atoms and that correspond to one of the formulae R1COOR2, R2OOC-R3-COOR2, and R1COO-R3-OOCR1, in which each of R1 and R2 independently represents a C1-22 alkyl group or C8-22 alkenyl group and R3 represents a C2-16 alkylene group;
(A.2) up to 50% by weight of aliphatic acid triglycerides of C8-22 aliphatic acids; and (A.3) up to 25% by weight of hydrocarbon molecules, said process comprising the steps of:
(I) forming, at a temperature sufficiently high that all components are present in liquid phase, an emulsion consisting essentially of:
a selected quantity of component (A);
a quantity of water having a weight at least equal to the selected quantity of component (A);
(B) about 0.1 to about 0.5 part by weight, per part by weight of component (A), of a primary emulsifier component having an HLB
value of 11 to 12 and consisting essentially of molecules selected from the group consisting of (B.1) adducts of ethylene oxide with C16-22 aliphatic alcohols and (B.2) adducts of ethylene oxide with partial esters between C3-6 polyols and C14-22 aliphatic acids; and (C) from 0.1 to 0.5 part by weight, per part by weight of component (A), of a co-emulsifier component consisting essen-tially of molecules selected from the group consisting of:

(C.1) saturated C16-22 aliphatic alcohols;
and (C.2) partial esters of C3-6 polyols with saturated C14-22 aliphatic acids;
(II) exposing the emusion formed in step (I) to a temperature within its phase inversion temperature range; and (II) cooling the emulsion formed in step (II) below its phase inversion temperature range.

3. A process according to claim 1, additionally comprising a step (IV) of diluting with water the oil-in-water emulsion formed in step (III).

4. A process according to claim 3, wherein primary emulsifier component (B) consists essentially of molecules that are adducts of 8 to 12 molecules of ethylene oxide with saturated C16-22 aliphatic alcohol molecules.

5. A process according to claim 2, wherein primary emulsifier component (B) consists essentially of molecules that are adducts of 8 to 12 molecules of ethylene oxide with saturated C16-22 aliphatic alcohol molecules.

6. A process according to claim 1, wherein primary emulsifier component (B) consists essentially of molecules that are adducts of 8 to 12 molecules of ethylene oxide with one saturated C16-22 aliphatic alcohol molecule.

7. A process according to claim 2, wherein oil component (A) consists essentially of molecules selected from classes (A.1) and (A.2) only and component (B) consists essentially of molecules that are adducts of 8 to 12 molecules of ethylene oxide with one saturated C20-22 aliphatic alcohol molecule.

8. A process according to claim 4, wherein component (A) consists essentially of molecules selected from classes (A.1) and (A.2) only and component (B) consists essentially of molecules that are adducts of 8 to 12 molecules of ethylene oxide with one saturated C20-22 aliphatic alcohol molecule.

9. A process according to claim 3, wherein component (A) consists essentially of molecules selected from classes (A.1) and (A.2) only and component (B) consists essentially of molecules that are adducts of 8 to 12 molecules of ethylene oxide with one saturated C20-22 aliphatic alcohol molecule.

10. A process according to claim 1, wherein component (A) consists essentially of molecules selected from classes (A.1) and (A.2) only and component (B) consists essentially of molecules that are adducts of 8 to 12 molecules of ethylene oxide with one saturated C20-22 aliphatic alcohol molecule.

11. A process according to claim 9, wherein component (C) consists essentially of molecules selected from the group consisting of cetyl alcohol, stearyl alcohol, and monoesters of glycerol, sorbitan, and trimethylolpropane with saturated C14-22 aliphatic acids.

12. A process according to claim 8, wherein component (C) consists essentially of molecules selected from the group consisting of cetyl alcohol, stearyl alcohol, and monoesters of glycerol, sorbitan, and trimethylolpropane with saturated C14-22 aliphatic acids.

13. A process according to claim 7, wherein component (C) consists essentially of molecules selected from the group consisting of cetyl alcohol, stearyl alcohol, and monoesters of glycerol, sorbitan, and trimethylolpropane with saturated C14-22 aliphatic acids.

14. A process according to claim 2, wherein component (C) consists essentially of molecules selected from the group consisting of cetyl alcohol, stearyl alcohol, and monoesters of glycerol, sor-bitan, and trimethylolpropane with saturated C14-22 aliphatic acids.

15. A process according to claim 4, wherein component (C) consists essentially of molecules selected from the group consisting of cetyl alcohol, stearyl alcohol, and monoesters of glycerol, sorbitan, and trimethylolpropane with saturated C14-22 aliphatic acids.

16. A process according to claim 3, wherein component (C) consists essentially of molecules selected from the group consisting of cetyl alcohol, stearyl alcohol, and monoesters of glycerol, sorbitan, and trimethylolpropane with saturated C14-22 aliphatic acids.

17. A process according to claim 16, wherein the oil component (A), the emulsifier (B), and the co-emulsifier (C) are used in a ratio by weight of A to B to C of 1 : 0.1 - 0.3 : 0.1 - 0.3.

18. A process according to claim 15, wherein the oil component (A), the emulsifier (B), and the co-emulsifier (C) are used in a ratio by weight of A to B to C of 1 : 0.1 - 0.3 : 0.1 - 0.3.

19. A process according to claim 14, wherein the oil component (A), the emulsifier (B), and the co-emulsifier (C) are used in a ratio by weight of A to B to C of 1 : 0.1 - 0.3 : 0.1 - 0.3.

20. A process according to claim 13, wherein the oil component (A), the emulsifier (B), and the co-emulsifier (C) are used in a ratio by weight of A to B to C of 1 : 0.1 - 0.3 : 0.1 - 0.3.

21. A process according to claim 12, wherein the oil component (A), the emulsifier (B), and the co-emulsifier (C) are used in a ratio by weight of A to B to C of 1 : 0.1 - 0.3 : 0.1 - 0.3.

22. A process according to claim 11, wherein the oil component (A), the emulsifier (B), and the co-emulsifier (C) are used in a ratio by weight of A to B to C of 1 : 0.1 - 0.3 : 0.1 - 0.3.

23. A process according to claim 10, wherein the oil component (A), the emulsifier (B), and the co-emulsifier (C) are used in a ratio by weight of A to B to C of 1 : 0.1 - 0.3 : 0.1 - 0.3.

24. A process according to claim 9, wherein the oil component (A), the emulsifier (B), and the co-emulsifier (C) are used in a ratio by weight of A to B to C of 1 : 0.1 - 0.3 : 0.1 - 0.3.

25. A process according to claim 8, wherein the oil component (A), the emulsifier (B), and the co-emulsifier (C) are used in a ratio by weight of A to B to C of 1 : 0.1 - 0.3 : 0.1 - 0.3.

26. A process according to claim 7, wherein the oil component (A), the emulsifier (B) and the co-emulsifier (C) are used in a ratio by weight of A to B to C of 1 : 0.1 - 0.3 : 0.1 - 0.3.

27. A process according to claim 5, wherein the oil component (A), the emulsifier (B), and the co-emulsifier (C) are used in a ratio by weight of A to B to C of 1 : 0.1 - 0.3 : 0.1 - 0.3.

28. A process according to claim 4, wherein the oil component (A), the emulsifier (B), and the co-emulsifier (C) are used in a ratio by weight of A to B to C of 1 : 0.1 - 0.3 : 0.1 - 0.3.

29. A process according to claim 3, wherein the oil component (A), the emulsifier (B), and the co-emulsifier (C) are used in a ratio by weight of A to B to C of 1 : 0.1 - 0.3 : 0.1 - 0.3.

30. A process according to claim 2, wherein the oil component (A), the emulsifier (B), and the co-emulsifier (C) are used in a ratio by weight of A to B to C of 1 : 0.1 - 0.3 : 0.1 - 0.3.

31. A process according to claim 30, wherein the oil component (A), the emulsifier (B), and the co-emulsifier (C) are used in a ratio by weight of A to B to C of 1 : 0.2 : 0.15.

32. A process according to claim 29, wherein the oil component (A), the emulsifier (B), and the co-emulsifier (C) are used in a ratio by weight of A to B to C of 1 : 0.2 : 0.15.

33. A process according to claim 28, wherein the oil component (A), the emulsifier (B), and the co-emulsifier (C) are used in a ratio by weight of A to B to C of 1 : 0.2 : 0.15.

34. A process according to claim 27, wherein the oil component (A), the emulsifier (B), and the co-emulsifier (C) are used in a ratio by weight of A to B to C of 1 : 0.2 : 0.15.

35. A process according to claim 26, wherein the oil component (A), the emulsifier (B), and the co-emulsifier (C) are used in a ratio by weight of A to B to C of 1 : 0.2 : 0.15.

36. A process according to claim 25, wherein the oil component (A), the emulsifier (B), and the co-emulsifier (C) are used in a ratio by weight of A to B to C of 1 : 0.2 : 0.15.

37. A process according to claim 24, wherein the oil component (A), the emulsifier (B), and the co-emulsifier (C) are used in a ratio by weight of A to B to C of 1 : 0.2 : 0.15.

38. A process according to claim 23, wherein the oil component (A), the emulsifier (B), and the co-emulsifier (C) are used in a ratio by weight of A to B to C of 1 : 0.2 : 0.15.

39. A process according to claim 22, wherein the oil component (A), the emulsifier (B), and the co-emulsifier (C) are used in a ratio by weight of A to B to C of 1 : 0.2 : 0.15.

40. A process according to claim 21, wherein the oil component (A), the emulsifier (B), and the co-emulsifier (C) are used in a ratio by weight of A to B to C of 1 : 0.2 : 0.15.

41. A process according to claim 20, wherein the oil component (A), the emulsifier (B), and the co-emulsifier (C) are used in a ratio by weight of A to B to C of 1 : 0.2 : 0.15.

42. A process according to claim 19, wherein the oil component (A), the emulsifier (B), and the co-emulsifier (C) are used in a ratio by weight of A to B to C of 1 : 0.2 : 0.15.

43. A process according to claim 18, wherein the oil component (A), the emulsifier (B), and the co-emulsifier (C) are used in a ratio by weight of A to B to C of 1 : 0.2 : 0.15.

44. A process according to claim 17, wherein the oil component (A), the emulsifier (B), and the co-emulsifier (C) are used in a ratio by weight of A to B to C of 1 : 0.2 : 0.15.