Source: https://patents.google.com/patent/US5300694?oq=7%2C190%2C101
Timestamp: 2018-03-24 06:37:20
Document Index: 186070520

Matched Legal Cases: ['Application No. 911052587', 'arts2', 'arts3', 'arts5', 'arts6', 'arts7', 'arts8', 'arts   4', 'arts  72', 'arts  20']

US5300694A - Alkoxylated compounds and their use in cosmetic stick formulations - Google Patents
Alkoxylated compounds and their use in cosmetic stick formulations Download PDF
US5300694A
US5300694A US07974145 US97414592A US5300694A US 5300694 A US5300694 A US 5300694A US 07974145 US07974145 US 07974145 US 97414592 A US97414592 A US 97414592A US 5300694 A US5300694 A US 5300694A
US07974145
Stelio J. Elmi
Elmi Stelio J
Novel phenol compounds of the formula: ##STR1## wherein R1 is an alkyl substituent of 15 carbon atoms, R is an ethyl or propyl substituent, and n is about 200.
This a division of copending application Ser. No. 07/845,860 filed Mar. 4, 1992 and now U.S. Pat. No. 5,258,136.
Helin et al, U.S. Pat. No. 3,226,352 discloses parasubstituted substituted ethoxylated phenols having from 7 to 15 ethoxy groups. A hydrophobic group containing 9 carbons is disclosed.
Gedeon et al. U.S. Pat. No. 4,268,498 discloses a clear cosmetic stick comprised of a number of ingredients, none of which includes sodium stearate or a hydrophobe substituted alkoxylated phenol. At column 1, lines 8-15, there is a disclosure that sodium stearate based sticks get hazy and cloudy.
Sabol et al, U.S. Pat. No 4,842,762 discloses a laundry soil and stain remover in applicator stick form. Formulations are set out in Examples 1 and 4 in which nonylphenol ethoxylate and stearic acid are employed. In Example 4, sodium ions are also present.
Additionally, European Pat. Application No. 911052587 (Publication No. 0 450 597A2) describes a gel stick which incorporates a water dispersible emollient that is a polyoxyethylene ether of a branched chain fatty alcohol, the fatty alcohol having from 8 to about 22 carbons and the average number of ethylene glycol ether units being from about 1 to 6. The gel stick composition has enhanced transparency to the transmission of light.
R.sub.4 -(O-R).sub.n OH
wherein R4 is (a) lanolin, (b) mono- and di-glycerides of C12 to C22 fatty acids, or (c) C12 to C22 fatty acids; and
The foregoing objects of this invention are also achieved by incorporating in a sodium stearate gel novel alkoxylated phenols of the formula: ##STR2## wherein R1 is an alkyl substituent from 8 to 18 carbon atoms, R is an ethyl (--C2 H4 --) or propyl substituent (--C3 H6 --) and n may range from 50 to 200. Preferably n is about 200, R1 is about 15 carbon atoms and the O--R or O--alkyl group is OC2 H4.
Other preferred compounds for such use are for example: ##STR3## wherein R2 and R3 are each, independently an alkyl substituent of 8 to 15 carbon atoms, preferably a linear alkyl of 9 carbon atoms (nonyl), R is an ethyl or propyl substituent, preferably ethyl and n is from 50 to 200, preferably about 150.
The use of the foregoing compounds provides for enhanced transparency to sodium stearate gel sticks as opposed to cloudy translucent sticks. The addition of up to about 1 to 8 parts per hundred of the aforedescribed alkoxylated compounds enhances transparency of the get, minimizes the "syneresis" effect upon storing the final gel sticks at low or high temperature, and also increases the setting point of the gel composition.
The gel compositions of the present invention are transparent to the transmission of light. "Transparent" generally means that sufficient light passes through the gel to enable an observer to see through the gel, without difficulty, an image, e.g. lettering. Generally, gel sticks in accordance with the present invention will transmit more than 40% of the light passed therethrough. Further, the gels of the present invention remain transparent for a reasonable period cf time, typically at least about one month at room temperature preferably for at least three months at room temperature.
More specifically, the terminology "transparent" may refer to a standard described by F. W. Wells in Soap and Chemical Specialties, Vol. XXI, No. 6 and No. 7 June and July 1955 which provides a criteria for transparency (in actuality translucency) A product, e.g. sodium stearate gel, in order to be considered transparent, i.e. translucent, must permit bold faced type of about 14 point size to be read easily through a quarter-inch section of the product. Other methods, for example "translucency voltage", have been employed to evaluate the transparency and translucency of soaps, see for example U.S. Pat. No. 2,970,116 to Kelly et al. incorporated herein by reference. In actuality, transparency is the limit of translucency wherein no attenuation or loss of transmission occurs, and images viewed through a "transparent" material will appear as if the material were not there at all.
It is believed that the alkoxylated substituent of the compounds used herein serves to solubilize the sodium stearate and prevent crystallization. Further, as the number of alkoxy groups increases, the set-up temperatures cf the gel also increases. Still further, the sodium stearate sticks of the present invention do not exhibit syneresis, set up at higher temperatures than similar gels, and maintain truer colors for longer periods of time.
Sodium stearate stick formulations, and in particular sodium stearate--propylene glycol/polyethylene glycol stick formulations, are well known in the art, see for example U.S. Pat. No. 4,226,889 to Yuhas, incorporated herein by reference.
wherein R4 is (a) lanolin, (b) mono- and di-glycerides of C12 to C22 fatty acids, or (c) a 12 to C22 fatty acid; and
PEG-12 PEG-65 Lanolin
Additional compounds which can be incorporated into such stick formulations are the alkoxylated phenols of the following formula: ##STR4##
wherein R1 is an alkyl substituent of from 8 to 18 carbon atoms, R is an ethyl or propyl substituent, and n is from abut 50 to 200. More specifically:
POE -50 Dodecyl Phenyl Ether
POE -100 Dodecyl Phenyl Ether
POE -150 Dodecyl Phenyl Ether
POE -200 Dodecyl Phenyl Ether
Additional alkoxylate phenols which can be incorporated in such stick formulations are: ##STR5##
wherein R2 and R3 are each, independently, an alkyl substituent of 8 to 15 carbon atoms, R is an ethyl or propyl substituent, and n is from about 50 to 200. More specifically:
Of these latter compounds Igepal DM 970 marketed by the General Aniline and Film Corporation is preferred. DM 970 is an ortho-para-nonyl ethoxylated phenol having 150 ethoxy groups. Other such phenols having other hydrophobic groups such as C8 -C15 for instance, are also useful, such as Sulfine® WLL (a dinonyl phenol ethoxylate) supplied by Finetex, Inc., but Igepal DM 970 is preferred.
Preferably, for example, the alkoxylated phenols are added to an aqueous sodium stearate gel stick formula in amounts of about one to eight parts per hundred, preferably about two to four parts per hundred to produce the desired transparent gel stick. The amount of sodium stearate in the gel is well known in the art, e.g. about 1-30 parts by weight per 100 parts of water, about 8 parts of sodium stearate being preferred. Of course, the optimum proportion of sodium stearate to water in any particular instance will depend upon the nature of the other ingredients of the cosmetic stick composition. Nonetheless, most useful compositions will have proportions of sodium stearate to water within the above ranges.
Another essential ingredient cf the cosmetic stick composition is an "active ingredient", by which is meant an ingredient which is desired to deposit on the skin of a human being. Such active ingredients can include biologically active materials such as bacteriostats and fungistats, pigments and dyes or other colorants, perfumes, emollients, ultraviolet absorbers or "sun screens", and talc. Of course, any active ingredient must be stable in the aqueous alkaline environment provided by the sodium stearate-water vehicle. Depending upon the intended use of the cosmetic stick composition, the amount of the "active ingredient" can vary from as little as 0.05 weight percent or less up to 50 weight percent or more of the total weight of the composition. Two or more active substances may also be present. For example, a talc stick can also include a bacteriostat and/or a fungistat for use as a medicated powder stick, for example a foot powder stick, or it can contain a pigment for use as a pigmented talc stick.
The sodium stearate stick composition is formed by mixing the ingredients at elevated temperatures sufficient to form a liquid solution or suspension, ordinarily about 70° C. to about 85° C., pouring the liquid into a mold or dispensing container and allowing it to cool and set. As indicated previously, the use of the alkoxylated phenols increase the set temperature In some cases, a period of several hours or even days may be required before the cosmetic stick composition is completely solidified. It is preferred that the water and sodium stearate, and optionally the other liquid or liquefiable ingredients, be first mixed to form a clear solution, and the solid ingredients such as talc or pigments are then added. The mixture is then partially cooled, at which time volatile components, such as perfume oils, are added, and then final cooling is effected.
When the cosmetic stick composition is subjected to temperature extremes, e.g. a temperature as low as about 0° to 40° C., or a temperature of about 50° C., or higher, it has been found that liquid exudes from the solid stick. Attempts to prevent such "syneresis" through the use of increased amounts of sodium stearate have not proven to be particularly successful because a hard, waxy composition results. It has been further found, however, that the addition of relatively small amounts of the alkoxylated compounds used in this invention increases the setting point, as well as the rate of setting, of the water-sodium stearate cosmetic stick base. Thus, stick-type cologne compositions which otherwise might be too soft for practical use in a stick-type product, such as deodorant colognes containing high proportions of such compounds, perfume oils, can be formulated into a cosmetic stick composition by the use of such compounds.
These same principles have been seen to apply, but with a lower degree of success with "substrates" other than phenol For example most fatty substrates, when ethoxylated, show activity in clarifying sodium stearate/propylene glycol sticks, and with different effects co stick integrity. For example:
______________________________________Na Stearate         4.0 partsPropylene glycol   71.0 partsWater              20.0 partsIgepal DM 970 (ortho-               4.0 partsparanonyl ethoxylatedphenol having 150 ethoxygroups)Urea                1.0 parts______________________________________
The above mixture was heated to about 80°-85° C. with stirring and poured into dispensing molds. Gelling commenced at about 70° C. The produce had excellent transparency.
The composition contained the following ingredients and prepared as above:
______________________________________Na Stearate         4.0 partsPropylene glycol   72.0 partsWater              20.0 partsIgepal DM 970 (ortho-               3.2 partsparanonyl ethoxylatedphenol having 150 ethoxygroups)Urea                0.8 parts______________________________________
______________________________________Na Stearate        4.0 partsPropylene glycol   73.0 partsWater              2.0 partsIgepal DM 970 (ortho-              2.4 partsparanonyl ethoxylatedphenol having 150 ethoxygroups)Urea               0.6 parts______________________________________
______________________________________Na Stearate   4%      4%      7%    7%Propylene Glycol        72%     68%     70.25%                              70.25%Water        20%     20%     21.42%                              21.42%Igepal DM 970        43%      8%      1.0%  2.0%(ortho-paranonylethoxylated phenolhaving 150 ethoxygroups)Urea         --      --      --    --Na Stearate   4%      4%      4%    4%    4%Propylene Glycol        71%     72%     73%   65.7% 58%Water        20%     20%     20%   27.3% 35Igepal DM 970         4.0%    3.20%   2.4%  2.4%  2.4%(ortho-paranonylethoxylated phenolhaving 150 ethoxygroups)Urea          1.0%    .8%     .60%  .60%  0.6%______________________________________
EXAMPLE 2IN-SITU FORMATION OF SODIUM STEARATE
______________________________________Stearic acid        3.9 partsNaOH (50% soln.)    1.2 partsPolyethylene glycol              72.0 partsWater              18.9 partsEthoxylated meta-nonyl               4.0 partsphenol having 200 ethoxygroups ("PDP-200")The pH was initially 9.37.______________________________________
pH initially @70° C. =7.82 is adjusted to 9.52. The molded product become cloudy within 1/2 hour.
EXAMPLE 3SOAP BAR
______________________________________1.     Na Stearate      5.0 parts2.     Polyethylene glycol                   60.1 parts3.     PDP-200 (ethoxylated                   4.0 parts  meta-nonyl phenol having  200 ethoxy groups).4.     Monoamide 716 (  1.0 parts5.     Water            17.5 parts6.     Myristic acid, HY 9514                   4.5 parts7.     Lauric acid, HY 9912                   4.5 parts8.     NaOH (50% aqueous)                   3.4 parts______________________________________
______________________________________              A    B______________________________________Sodium Stearate      4.00   5.00Polyethylene Glycol  67.68  64.70Water                18.80  18.00PDP-200 (ethoxylated 4.00   4.00meta-nonyl phenolhaving 200 ethoxygroupsMyristic Acid        2.00   3.00Lauric Acid          2.00   3.00Sodium Hydroxide-50% 1.52   2.30______________________________________
______________________________________           A       B______________________________________Sodium Stearate   7.0    parts   4.0 partsPDP-200 (ethoxylated             4.0 partsmeta-nonyl phenolhaving 200 ethoxygroupsPolyethylene Glycol             72.0   parts  72.0 partsWater             21.00  parts  20.0 parts______________________________________
______________________________________USE OF SULFINE.sup.R WLL (FINETEX)AS THE ALKOXYLATED DINONYL PHENOL______________________________________Na Stearate  4.1    5.7    4.1   4.1  4.1   4.1Polyethylene Glycol        72.0   72.0   71.0  70.0 69.0  68.0*Sulfine WLL 5.8    3.0    5.8   5.8  5.8   5.870% (Dinonyl phenolethoxylate)KHCO.sub.3                 1.0   2.0  3.0   4.0Water        18.1   19.3   18.1  18.1 18.1  18.1______________________________________ *Sulfine ® WLL from Finetex, Incorporated  Dinonyl phenol ethoxylate.
1. A phenol compound of the formula: ##STR6## wherein R1 is an alkyl substituent of 15 carbon atoms, R is an ethyl substituent, and n is about 200.
2. A phenol compound of the formula: ##STR7## wherein R1 is an alkyl substituent of 15 carbon atoms, R is an ethyl substituent, and n is about 200.
US07974145 1992-03-04 1992-11-10 Alkoxylated compounds and their use in cosmetic stick formulations Expired - Fee Related US5300694A (en)
PCT/US1993/003124 WO1994022801A1 (en) 1993-03-29 1993-03-29 Alkoxylated compounds and their use in cosmetic stick formulations
US84586092 Division 1992-03-04 1992-03-04
US5300694A true US5300694A (en) 1994-04-05
ID=22236479
US07845680 Expired - Fee Related US5258136A (en) 1992-03-04 1992-03-04 Alkoxylated compounds and their use in cosmetic stick formulations
US07974145 Expired - Fee Related US5300694A (en) 1992-03-04 1992-11-10 Alkoxylated compounds and their use in cosmetic stick formulations
US (2) US5258136A (en)
EP (1) EP0691947B1 (en)
JP (1) JPH10506656A (en)
DE (2) DE69327340D1 (en)
WO (1) WO1994022801A1 (en)
US3442654A (en) * 1964-12-11 1969-05-06 Gaf Corp Gelatin coating composition containing purified polyoxyalkylene glycol ether
US2385818A (en) * 1942-03-18 1945-10-02 Safety Fuel Inc Solidified normally liquid hydrocarbons
US2860103A (en) * 1954-10-12 1958-11-11 Pan American Petroleum Corp Making gelled hydrocarbons
JPH0474400B2 (en) * 1986-10-02 1992-11-26
JPH0723597B2 (en) * 1989-12-08 1995-03-15 三洋化成工業株式会社 Papermaking synthetic fibers dispersant and papermaking process
WO1994022801A1 (en) 1994-10-13 application
DE69327340T2 (en) 2000-06-08 grant
EP0691947A1 (en) 1996-01-17 application
EP0691947A4 (en) 1996-02-21 application
JPH10506656A (en) 1998-06-30 application
US5258136A (en) 1993-11-02 grant
EP0691947B1 (en) 1999-12-15 grant
DE69327340D1 (en) 2000-01-20 grant