Abstract:
A powdered compressed cosmetic material comprising a hydroxypropyl-etherified glycolipid ester represented by the general formula; ##STR1## wherein R 1  represents a methyl group or a hydrogen atom, R 2  represents a saturated or unsaturated hydrocarbon group having carbon atoms of 11 to 15 when R 1  is a methyl group, or R 2  represents a saturated or unsaturated hydrocarbon group having carbon atoms of 12 to 16 when R 1  is a hydrogen atom, A represents the group ##STR2## R 3  represents a saturated or unsaturated hydrocarbon group having carbon atoms of 1 to 20 or --(A) h  H, and a, b, c, d, e, f, g and h are integers, whose sum ranges from 1 to 6.

Description:
BACKGROUND OF THE INVENTION 
     1. Field of the Invention 
     This invention relates to powdered compressed cosmetics, more particularly to a novel powdered compressed cosmetic material comprising a hydroxypropyl-etherified glycolipid ester (hereinafter abbreviated as &#34;POSL&#34;) represented by the general formula (I); ##STR3## wherein R 1  represents a methyl group or a hydrogen atom, R 2  represents a saturated or unsaturated hydrocarbon group having carbon atoms of 11 to 15 when R 1  is a methyl group, or R 2  represents a saturated or unsaturated hydrocarbon group having carbon atoms of 12 to 16 when R 1  is a hydrogen atom, A represents the group ##STR4## R 3  represents a saturated or unsaturated hydrocarbon group having carbon atoms of 1 to 20 or --(A) h  H, and a, b, c, d, e, f, g and h are integers, whose sum ranges from 1 to 60. 
     2. Description of the Prior Art 
     Powdered compressed cosmetic materials have hithertofore been produced by compressing and molding under elevated pressure a mixture of a major component such as talc or sericite, and a combining agent such as a paste, for instance, carboxymethyl cellulose, or an emulsifying agent, for instance, squalane or lanolin. However, these known cosmetic materials, which are usually produced by compression to such extent that applicable hardness can be obtained, are liable to be easily cracked when dried or fallen by mistake while being carried with the consumer, with eventual unfitness for use. 
     In order to eliminate the above noted defects, the present inventors have made a wide variety of studies, and as a result, have found that a powdered compressed cosmetic material of good and stable quality and performance can be produced by incorporating POSL of the formula (I) in the cosmetic composition. 
     Based on this finding, the present invention has been accomplished. 
     SUMMARY OF THE INVENTION 
     Briefly stated, this invention provides an excellent powdered compressed cosmetic material which comprises POSL represented by the formula (I) and which is prevented against cracking even when dried or given a shock. 
     DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS 
     POSL to be used in the present invention is a novel compund which can be produced, for instance, by reacting glycolipid or a glycolipid ester represented by the general formula (II); ##STR5## wherein R 4  represents a saturated or unsaturated hydrocarbon group having carbon atoms of 1 to 20 or a hydrogen atom, R 1  and R 2  are the same as defined above, with propylene oxide in the presence of an alkali catalyst (Japanese Patent Application No. 24306/1978 now U.S. Pat. No. 4,195,177, issued Mar. 25, 1980). 
     The properties of POSL which is useful in and typical of the invention are shown below. 
     
         __________________________________________________________________________       Addition      Saponifi-       mole Hydroxyl                 Acid                     cationR.sup.1   R.sup.2  R.sup.3       number            value                 value                     value                          Appearance__________________________________________________________________________CH.sub.3   C.sub.15 H.sub.28  CH.sub.3       5    420.3                 0.2 61.3       7    376.5                 0.7 53.5 Viscous                          paste sub-       15   261.5                 0.3 37.0 stance       30   167.2                 1.2 21.5CH.sub.3   C.sub.15 H.sub.28  C.sub.12 H.sub.25       7    325.3                 0.2 47.0 Paste-like       15   236.2                 0.8 31.5 wax sub-       30   159.3                 0.5 20.7 stanceCH.sub.3   C.sub.15 H.sub.28  -(A).sub.h H       5    492.0                 0.7 60.5       8    413.5                 0.0 51.5 Viscous                          paste sub-       15   299.0                 0.1 37.5 stance       30   185.3                 0.0 23.8__________________________________________________________________________ 
    
     By the term powdered compressed cosmetic material is meant the so-called pressed face powder, cheek rouge, highlight, eye-shadow or the like for use with a compact which is produced by mixing a major component such as talc, kaolin, sericite, silk powder, nylon powder, metal soap, starch or the like, with a combining agent such as a paste, oil or emulsion, for instance, squalane, liquid paraffin, isopropyl myristate, oleyl alcohol, lanolin or the like, and further incorporating an inorganic or organic pigment in the above mixture, and finally subjecting the resulting mixture to compression molding. 
     The powdered compressed cosmetic material according to the present invention can be produced by any conventional dry or wet method, with the exception that POSL is mixed with the above composition in an amount of 0.1 to 10 percent, preferably 3 to 7 percent, based upon the total weight of the powdered compressed cosmetic material. 
    
    
     This invention will now described with reference to certain specific Examples, but the invention is not limited to the Examples. The following Reference Example is illustrative of the preparation of POSL which is useful in the invention. 
     REFERENCE EXAMPLE 
     (i) To a mixture of 1500 g of glucose, 75 g of a yeast extract and 15 g of urea was added water to adjust the whole volume to 15 l, and the resulting mixture was sterilized and utilized as a fermentation liquid. To this fermentation liquid was inoculated Torulopsis bombicola which had been cultured in the same culture medium as above at 30° C. for 48 hours. The fermentation was started under the following conditions: temperature, 20° C.; stirring, 300 rpm; and aeration, 0.33 VVM. The culturation was conducted for 24 hours after inoculation of the microorganisms, and 150 g of beef tallow was added, followed by adding the same amount of beef tallow at intervals of 24 hours. The added beef tallow amounted to 900 g. After the final addition, the fermentation was continued for additional 24 hours. The fermentation time amounted to 168 hours. After the completion of the fermentation, the sophorolipid layer precipitating at the bottom of a fermentor was collected by decantation to give 1300 g of sophorolipid, which was in the form of a paste having a water content of about 50%. 
     (II) 100 g of the thus obtained sophorolipid together with 2.5 g of polypropylene glycol having an average molecular weight of 200 was placed in a 200 ml round bottom flask equipped with a stirrer and a Liebig condenser. The mixture was evaporated with stirring an an oil bath (80° C.) under a reduced pressure of 250 mmHg to eliminate water. 2 hours later, the distillation of water was completed, and the water content at that time was found to be less 1%. 
     (iii) 150 g of methanol was added to the thus prepared polypropylene solution of sophorolipid, and to the resulting mixture was added 2.5 g of sulfuric acid. The mixture was reacted at 40° C.±2° C. for 90 minutes. The reaction was regarded as having been completed at the time when many spots of the raw material or sophorolipid converged on one spot corresponding to a glycolipid methyl ester by thin-layer chromatography on silica gel [developing solvent: chloroform-methanol-acetic acid (75:20:5)]. 
     After the completion of the reaction, the mixture was made neutral with a given amount of potassium hydroxide and then filtered. The filtrate was placed again in a round bottom flask equipped with a Liebig condenser, and methanol and methyl acetate were removed by distillation to obtain 48 g of a mixture containing 94% of a crude [2&#39;-O-β-D-glucopyranosyl-β-D-glucopyranosyl)oxy]alkanic acid and alkenic acid methyl ester in the form of a brown paste and coexisting polypropylene glucose. This mixture was purified by column chromatography on silica gel to obtain a pure [(2&#39;-O-β-D-glucopyranosyl-β-D-glucopyranosyl)oxy]alkanic acid and alkenic acid methyl ester. 
     
         ______________________________________IR (cm.sup.-1):         ##STR6##        1380-3200 (OH sugar)        900-750 (glucopyranose ring)NMR [δ(pyridine)]:        1.1-1.6 (CH.sub.2CH.sub.2)        3.6 (OCH.sub.3)        3.5-5.0 (sugar)        5.5 (CHCHunsaturated fatty acid)Oil-characteristics analysis:            Acid value:      0            Hydroxy value:   615            Saponification value:                             88            Ester value:     87______________________________________ 
    
     (iv) Into an autoclave were placed 100 g of the thus obtained mixture of the [(2&#39;-O-β-D-glucopyranosyl-β-D-glucopyranosyl)oxy]alkanic acid and alkenic acid methyl ester and coexisting polypropylene glycol and 0.25 g of potassium hydroxide. Subsequently, propylene oxide gas was bubbled into the mixture in an amount corresponding to a predetermined addition mole number, and the mixture was reacted at 100°-120° C. for 6 hours. After the completion of the reaction, the mixture was neutralized with phosphoric acid and filtered under high pressure to obtain a crude product in the form of a brown paste. This product was purified by chromatography on silica gel to obtain a pure polyoxypropylene[(2&#39;-O-β-D-glucopyranosyl-β-D-glucopyranosyl)oxy]alkalic acid and alkenic acid methyl ester as a pale yellow paste. 
     EXAMPLE 1 
     Test samples A to D were prepared according to the compositions and preparation methods indicated below. After these test samples and commercial goods E and F were preserved at 50° C. for 12 hours, any cracks arising from drying were observed with the naked eye. 
     The results obtained are shown in Table 1. From these results, it can be seen that the samples C and D produced by the present method have nothing defective and are stable. 
     
         ______________________________________Sam-                              Preparationples Kinds      Compositions (%)  methods______________________________________A    Conventional           Talc           60   Dry methodformulation           Sericite       20   Compressive           Koalin         10   pressure:           Aluminum stearate                          2    50 kg/cm.sup.2           Lanolin        2           Squalane       3           Titanium oxide 2           Iron oxide     1B    Conventional           Talc           70   Wet methodformulation           Tericite       25   Compressive           Aluminum stearate                          2    pressure:           Titanium oxide 2    40 kg/cm.sup.2           Iron oxide     1           0.1% Carboxymethyl           cellulose      20C    Applicants&#39;           Talc           75   Dry methodformulation           Sericite       16   Compressive           Aluminium stearate                          2    pressure:           POSL-1         4    40 kg/cm.sup.2           Titanium oxide 2           Iron oxide     1D    Applicants&#39;           Talc           80   Wet methodformulation           Kaolin         8    Compressive           Aluminium stearate                          3    pressure:           POSL-2         6    40 kg/cm.sup.2           Titanium oxide 2           Iron oxide     1E    Commercial solid face powderF    Commercial cheek rouge______________________________________ POSL-1: R.sup.1 = CH.sub.3, R.sup.2 = C.sub.15 H.sub.28 , R.sup.3 = C.sub.12 H.sub.25 the sum of a to h = 7 in the formula (I) POSL-2: R.sup.1 = CH.sub.3, R.sup.2 = C.sub.15 H.sub.28, R.sup.3 = -(A).sub.h H the sum of a to h = 15 in the formula (I) 
    
     
                       TABLE 1______________________________________Sample marks   Cracked conditions______________________________________A              Cracked and exfoliated partlyB              CrackedC              Not cracked nor exfoliatedD              Not cracked nor exfoliatedE              CrackedF              Cracked and exfoliated partly______________________________________ 
    
     EXAMPLE 2 
     The same samples A to F as used in Example 1 were placed in compacts, and the compacts were each dropped ten times naturally from a distance or height of 1.5 m. Any cracks caused by such falling test were observed with the naked eye. 
     The results obtained are shown in Table 2. From these results, it can be seen that the samples C and D produced by the present method were unaffected by the test and were found to retain their stability. 
     
                       TABLE 2______________________________________Samples     Cracked conditions______________________________________A           Cracked and exfoliated almost wholly       from the compactB           Cracked and exfoliated partly from the       compactC           Not cracked nor exfoliatedD           Not cracked nor exfoliatedE           Cracked and exfoliated partly from the       compactF           Cracked and exfoliated almost wholly       from the compact______________________________________ 
    
     EXAMPLE 3 
     Four species A to D extracted from the same samples as used in Example 1 and two species G and H freshly prepared by the present method were cut off in a region of 3 cm×3 cm, respectively. These samples were each placed horizontally and given a stress of 5 kg/cm 2  from a horizontal direction at a rate of 5 mm/minute until any cracks were caused. The distance (mm×10) by which the dynamic point migrated was measured. 
     The results obtained are shown in Table 3. From these results, it can be seen that the migration distance of the present samples is large, which indicates these samples are resistant to deformation and stable. 
     
                       TABLE 3______________________________________   Test runs                                    AverageSamples   1st    2nd     3rd   4th  5th  values______________________________________A         30     33      28    29   32   30.4B         28     27      29    32   31   29.4C         45     42      44    43   42   43.2D         41     42      41    41   43   41.6G         39     41      42    39   40   40.2H         40     41      39    42   42   40.8______________________________________Compositions of Samples G and H         SamplesCompositions    G           H______________________________________Talc            56 parts    65 partsSericite        20          16Aluminium stearate           2           2Titanium oxide  2           2Iron oxide      1           1Kaolin          10          8Lanolin         2           1Squalane        3           2POSL-3          4           --POSL-4          --          3Preparation method           Dry method  Dry methodCompressive pressure           40 kg/cm.sup.2                       40 kg/cm.sup.2______________________________________ POSL-3: R.sup.1 = CH.sub.3, R.sup.2 = C.sub.15 H.sub.28, R.sup.3 = CH.sub.3 the sum of a to h = 30 in the formula (I) POSL-4: R.sup.1 = CH.sub.3, R.sup.2 = C.sub. 15 H.sub.28, R.sup.3 = -(A).sub.h H the sum of a to h = 5 in the formula (I)