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    • 专利摘要:
    There is disclosed a silicone substitute for use in a personal care formulation comprising a mixture of at least one polymeric ester and at least one non-polymeric ester. The polymeric ester is an esterification reaction product of (i) at least one first dicarboxylic acid, (ii) at least one first monofunctional alcohol or monofunctional carboxylic acid, and (iii) glycerin or derivatives thereof. The non-polymeric ester is an esterification reaction product of (i) at least one second dicarboxylic acid and (ii) at least one second monofunctional alcohol, the substituent being substantially free of silicone. There is disclosed a personal care formulation that is substantially free of silicone, the formulation comprising a silicone substitute consisting essentially of a mixture of at least one polymeric ester, As described above, and a non-polymeric ester as described above. Corresponding methods are also described.
    公开号:CH707632B1
    申请号:CH00898/14
    申请日:2012-11-14
    公开日:2016-11-15
    发明作者:Burgo Rocco；Winn Daniel；Burch Kimberly
    申请人:Inolex Investment Corp；
    IPC主号:
    专利说明:

    Description
    [0001] The present application claims the benefit under US 35 § 119 (e) of Provisional US Patent Application No. 61/559266, filed Nov. 14, 2011, the entire content of which is incorporated Herein by reference.
    BACKGROUND OF THE INVENTION [0002] Silicone fluids are widely used in toiletries, cosmetics and personal care formulations. The most frequently used are dimethicones, cyclomethicones, and phenyltrimethicone (hereinafter all silicone materials are referred to as "silicones"). Incorporated in a skin care formulation, silicone fluids offer various advantages such as improved sliding, reduced bonding, emollient communication, and other changes in the "sensory" characteristics of the formulation , As well as other advantages. Incorporated in hair care formulations such as conditioners, they can reduce the detangling force in the wet state and increase the shine of the hair.
    Silicone fluids have been considered to be particularly useful since they tend to offer the above-mentioned advantages without contributing to an oily or fatty side and give what many consider a "dry" skin feeling. This attribute is highly desirable in toiletries, cosmetics and other personal care formulations such as creams, lotions, antiperspirants, shaving formulations, and make-up formulations. Further advantages are that silicones are excellent dispersing and spreading agents, generally have a light white color, a low odor, and are resistant to chemical attack and oxidation. These attributes make them particularly suitable for personal care applications. However,
    Description of the Related Art [0004] For example, there has been concern about the safety of the use of silicone fluids on the skin. In light of the possible links between silicone and silicone degradation products with regard to the development of autoimmune system deficiencies in women with silicone breast implants and / or persons suffering from other disorders, Materials have recently been the subject of a more rigorous review by the Food and Drug Administration (FDA). Although definitive links have not been confirmed, many cosmetics manufacturers have taken steps to try to reduce or eliminate the silicone ingredients from the formulations.
    [0005] Furthermore, silicones have also been implicated as potentially harmful to the environment. For example, Environment Canada has published a document indicating that dimethicones are suspected to be environmental toxins and bioaccumulative.
    Accordingly, there is a need in the art to identify alternative non-silicone fluids which offer silicone-like advantages in a formulation but do not bring actual or perceived health and environmental risks.
    [0007] The industry has made efforts to meet this need. For example, publication of US patent application 2005/0260150 discloses esters of low viscosity which can be used in replacement of low viscosity silicone fluids. United States Patent Application Publication 2004/0241 200 describes mixtures of certain synthetic esters with volatile hydrocarbons which are useful for the replacement of volatile tetrameric and pentameric cyclomethicones. US Patent Application Publication 2009/0123939 discloses mixtures of hydrocarbon fluids useful for the replacement of volatile tetrameric and pentameric cyclomethicones. United States Patent Application Publication 2011/0 064 685 discloses personal care compositions comprising an aqueous dispersion comprising a metallocene catalyzed polyolefin and an ethylene acrylic acid copolymer; A cationic polymer; And at least one cosmetically acceptable surfactant, emollient or active cosmetic, provided that the personal care composition contains less than 0.09% by weight of silicone and is preferably substantially free of silicone.
    [0008] As the population becomes more aware of the potential negative effects on the organism and the environment associated with the use of fossil fuel-derived ingredients, the personal care industry has rapidly advanced its research of ingredients " Natural "for use in virtually all types and forms of cosmetic formulation. The media has led to this growth by popularizing the idea that there may be potential negative effects on the body and the environment associated with the use of fossil fuel-derived ingredients. The personal care industry has rapidly advanced its attempts to identify "natural" ingredients for use in virtually all types and forms of cosmetic formulation. Especially, Although used in marketing, the term "natural" has not yet been clearly defined in this context; Efforts are being made by industry trade organizations to give a more concise and coherent meaning to the term.
    [0009] It may take some time before a universal definition accepted by the natural industry is proposed; However, it is generally recognized that materials derived from renewable and / or sustainable sources, or alternatively non-fossil fuel sources, are considered to be natural. Petrochemicals are derived from fossil fuels and are not considered natural. No derivative of petrochemicals is considered natural. As such, silicones are not classified as natural, since they are derived from petrochemicals. Consequently,
    BRIEF SUMMARY OF THE INVENTION A silicone substitute is described herein for use in a personal care formulation comprising a mixture of at least one polymeric ester and at least one non-polymeric ester. The polymeric ester is an esterification reaction product of (i) at least one first dicarboxylic acid, (ii) at least one first monofunctional alcohol or monofunctional carboxylic acid, and (iii) glycerin or derivatives thereof. The non-polymeric ester is an esterification reaction product of (i) at least one second dicarboxylic acid and (ii) at least one second monofunctional alcohol, the substituent being substantially free of silicone.
    [0011] Also described is a personal care formulation which is substantially free of silicone, the formulation comprising a silicone substitute consisting essentially of a mixture of at least one polymeric ester as described above and an ester Non-polymeric polymer as described above. Associated processes are also disclosed.
    BRIEF DESCRIPTION OF THE SEVERAL VIEWS OF THE DRAWINGS [0012] The foregoing summary may be better understood when read in conjunction with the accompanying drawings. In order to illustrate aspects of the invention, the data and embodiments of the invention have been shown in the drawings. It should be understood, however, that the invention is not limited to the precise arrangements and means shown. In the drawings:
    FIG. 1 shows the infrared spectrum of an exemplary non-polymeric ester of the invention, deheptyl succinate;
    FIG. 2 shows the infrared spectrum of an exemplary polymeric ester of the invention, CGC type 4;
    FIG. 3 represents the propagation velocity of the silicone substitute relative to that of the silicone bitual material in graphic form;
    FIG. 4 is a table indicating the amounts of reagents of different sample and comparative sample formulations provided to human test subjects in panel evaluation of comparative skin sensation properties;
    FIG. 5 is a copy of the survey used by the panel in the evaluation of sample and comparative sample formulations;
    FIG. 6 (containing figures 6A to 6E) represents the results of the panel evaluation in graphical form;
    FIG. 7 is a photographic recording of data demonstrating the comparative tackiness (tack) of the silicone substitute and the usual silicone-containing formulation
    FIG. 8 shows the results of an evaluation of pigment grinding; and
    FIG. 9 shows the results of an evaluation of the shine (shine) of hair to which the silicone substitutes have been applied.
    DETAILED DESCRIPTION OF THE INVENTION The invention described herein encompasses silicone substitutes for use in personal care formulations (such as, without limitation, shampoos, makeup removers, conditioners, cosmetics and lotions) Which are substantially free of silicone (s), but have substantially equivalent end-use and / or end-use characteristics. More specifically, the Applicant has made the surprising discovery that by mixing certain types of natural ester fluids (ie, not derived from petrochemicals) certain desirable characteristics usually conferred by silicone fluids to formulations of Personal care can be obtained, including, for example, spreading speed, skin sensation, sticky reduction, The dispersion of the pigment, and the shine of the hair. By using the silicone substitutes of the invention, personal care formulations, including skin and hair products, which contain natural ingredients, are substantially free of silicone, and are perceived by end-users As having aesthetic, touch and / or skin sensing properties identical or similar to those of conventional silicone-containing formulations.
    By the term "substantially silicone-free" it is meant that the personal care formulations are formulated without the inclusion of any initial compounds containing silicone groups. For example, the formulations of the invention contain less than 0.09% by weight of silicone, and preferably 0.08% by weight or less.
    The invention comprises a natural silicone substitute for use in personal care formulations which is a mixture of at least one polymeric ester and at least one non-polymeric ester. The term "natural", as used herein, describing acids, alcohols and / or esters, means that all atoms contained in the structure of the acid, ester or alcohol which are used to prepare the esters are Obtained from renewable sources and / or from sustainable sources. "Renewable and sustainable" means that carbon is not obtained from petrochemical sources. Examples of non-petrochemical carbon sources may include, but are not limited to, plants, biomass of agricultural or forestry waste.
    In the invention, amalgams or mixtures of non-polymeric esters and polymers derived from the esterification of naturally occurring acids and alcohols are particularly useful. The term "esterification" is used herein to describe a condensation reaction between a carboxylic acid group and / or a carboxylic acid ester group with a hydroxyl group. An "esterification reaction product" is a product resulting from this event. The silicone substitutes included in the invention are a mixture of polymeric and non-polymeric esters formed from esterification reactions.
    [0017] Each of the esters present in the silicone replacement fluid is derived from the esterification of at least one dicarboxylic acid. In the practice of the invention, the polymeric ester is a product of the esterification reaction of at least one first dicarboxylic acid, at least one monofunctional or monofunctional carboxylic acid and glycerin and / or a derivative Of the latter. The polymeric esters in a given silicone substitute can be obtained from the same first dicarboxylic acid, first monofunctional alcohol or monofunctional carboxylic acid, and glycerine or glycerine derivative or they can be prepared from a mixture of first dicar -boxylic acids, first monofunctional alcohols and / or monofunctional carboxylic acids,
    The non-polymeric ester of the silicone substitute is a reaction product of at least one second dicarboxylic acid and at least one second monofunctional alcohol. As with the polymeric esters, the non-polymeric ester in a given silicone substitute can be obtained from the same second dicarboxylic acid and a second monofunctional alcohol or can be prepared from a mixture of second dicarboxylic acids and second Monofunctional alcohols or any permutation of these materials, so that the "non-polymeric ester" included in the silicone mixture / substitute itself is an amalgam or a mixture of various non-polymeric esters.
    In the case of each of the polymeric ester and the non-polymeric ester, suitable dicarboxylic acids and / or monohydric alcohols may independently contain short- or medium-length carbon chains (although polymeric and non-polymeric esters Polymers need not necessarily be prepared from starting materials having the same number of carbon atoms). By "short" chain length is meant that the compound contains from one to six carbon atoms. By "medium" chain length, it is meant that the compound contains seven to twelve carbon atoms.
    In certain embodiments, the monofunctional dicarboxylic acids and / or alcohols may independently contain chains of 1,2,3,4,5,6,7,8,9,10,11,12,13,14 , Or 15 carbon atoms. In other embodiments, the monofunctional dicarboxylic acids and / or alcohols may independently contain chains of 10 to 25 carbon atoms and / or 1 to 10 carbon atoms. In any embodiment of the invention, one or more of the monofunctional dicarboxylic acids and / or alcohols may independently have carbon chains which are independently linear and / or branched and / or carbon atoms which are independently saturated And / or unsaturated and / or functionalized or nonfunctionalized. In some embodiments,
    Particularly useful acids and / or alcohols may be those which contain saturated linear chains containing from three to ten carbon atoms.
    [0022] Any dicarboxylic acids known or developed in the art may be independently selected for use in esterification reactions, including but not limited to 1,4-butanedioic acid (succinic acid), 1,5-pentanedioic acid (glutaric acid), 1,6-hexanedioic acid (adipic acid), 9-nonanedioic acid (azelaic acid) and 1,10-decanedioic acid. Under certain circumstances, sebacic acid may be preferred.
    All of the monofunctional dicarboxylic acids known or developed in the art may be independently selected for use in the esterification reaction, including but not limited to hexa-nic acid (caproic acid), Heptanoic acid, octanoic acid (caprylic acid), nonanoic acid, deca-noic acid (capric acid) and dodecanoic acid (lauric acid). In some cases, caprylic acid and capric acid may be preferred.
    [0024] Glycerin or glycerine derivatives are used in the preparation of the polymeric ester. The glycerine derivatives include, but are not limited to, those derived from the condensation of glycerol with itself to higher glycerol ether derivatives, called polyglycols.
    All monofunctional alcohols known or developed in the art may be used, including but not limited to 1-hexanol, 1-heptanol, 1-octanol, 2-octanol and 1-decanol. Under certain conditions, 1-heptanol may be preferred.
    In each case, it may be preferred that the acid (s), the alcohol (s) and / or the polyols (glycerine or its derivatives) be natural as defined above.
    In the formation of the esters which form the silicone substitutes included in the invention from natural reagents, one or more dicarboxylic acids are esterified with one or more monofunctional alcohols and / or one or more monofunctional carboxylic acids. The esters may be formed by any esterification technique known in the art. For example, in a first reaction, a non-polymeric ester derived from the esterification of one or more monofunctional alcohols with one or more dicarboxylic acids is prepared. In a second reaction, a polymeric ester derived from one or more dicarboxylic acids, one or more monofunctional carboxylic acids, and glycerol and / or polyglycerol is prepared.
    To prepare the silicone substitute, non-polymeric and polymeric esters are then mixed in a ratio determined such that the substitute gives a personal care formulation performance characteristics that correspond to the silicone fluid the mixture is to Replace, for example, cyclomethic cone and / or dimethicone fluids. "Performance characteristics" refer to desirable final properties encountered by the consumer and / or product formulator that silicone fluids confer on personal care formulations, such as speed of propagation, skin sensation and other Properties of touch (slippage or drag, feeling of smoothness, residual sensation, speed of absorption in the skin, shine / gloss of hair,
    The polymeric and non-polymeric esters may be present in the silicone substitute in any desired ratio as long as the performance characteristics are attained or maintained. Assessment of a given mixture to ensure it has adequate and desired performance characteristics as a silicone substitute (as dictated by the final personal care formulation) is a matter of routine testing, Well within the skill of an average formulator. In some cases the weight ratio of polymeric ester to non-polymeric ester may be from about 1 to about 1 to about 1 to about 50 (i.e., 1: 1 to 1 : ~ 50).
    In some cases for convenience of formulation it may be desirable to use an identified ratio of polymeric ester to non-polymeric ester in the silicone substitute which is adjusted such that the silicone substituent has A specific viscosity. (In this way, a formulator of personal care products which seeks to substitute a silicone substitute in its formulation instead of a silicone of specific viscosity does not have to modify its formulation by other means, which increases The convenience of the silicone substitute.) Under these circumstances, the identified ratio can be determined by measuring the viscosity of the final product (the silicone substitute) and adjusting the ratio as necessary to arrive at the target viscosity. For example, A silicone substitute may be desired which has a viscosity of from about 1 to about 1000 cSt, from about 10 to about 500 cSt, from about 20 to about 350 cSt, from about 50 to about 200 cSt and / or d About 70 to about 100 cSt (1 cSt = 1 mm2 / s). Under certain circumstances, to facilitate manipulation by personal care formulators, it may be desirable to prepare silicone substitutes having a determined ratio of polymeric esters to non-polymeric esters which results in viscosities of about 10, about 20 , About 50, about 100, about 200, and / or about 350 (all in cSt, i.e. mm2 / s).
    [0031] The invention also includes personal care formulations which are natural and are substantially free of silicone. The personal care formulations include the silicone substitute according to the invention and at least one additional ingredient (which is not silicone). Any ingredient that may be applied to the hair, skin or nails may be included, including pharmacological agents. Examples of ingredients may include, but are not limited to, a surfactant, flavoring agent, perfume, opacifying agent, colorant, wax, emulsifier, fat, oil, preservative, UV absorbent compound, detergent, foaming agents, stabilizers, pH modifiers, foaming agents, moisturizers, water, alcohol, urea, A cosmetic active agent, a pigment, a wetting agent, a hair or skin softener and a solvent. Others may include: acetone, water, alcohol, parabens, mineral oil, vegetable oil, olive oil, paraffin, PEG, polyethylene, polyethylene glycol, polyoxyethylene, oxynol, petroleum jelly, lauryl sodium sulphate, Sodium hydroxymethylglycinate, triethanolamine, diethanolamine cocamide, diethanolamine laurimide, diethanolamine linoleamide, diethanolamine oleamide, oxybenzone, essential oils, emollient, octylmethoxycinnamate, titanium dioxide, sulphate of sodium myreth, And zinc oxide.
    The personal care formulation may be prepared by any means known in the art and the methods will necessarily vary depending on the particular type of personal care formulation to be prepared (eg, antiperspirant formulation for underarms with respect to A skin cleansing formulation). The personal care formulation itself may take the form of a solid, semi-solid, liquid, gel, aerosol or aerosol material, film, paste, cream, Lotion, emulsion, suspension, and / or powder.
    [0033] The silicone substitute may be present in the personal care formulation in any amount; The amount will vary depending on various factors, including the particular type of personal care formulation to be prepared. In some circumstances it may be preferred that the silicone substitute be present in the personal care formulation in an amount of from about 1% to about 95% by weight, from about 5% to about 80% by weight, from about 10 From about 15% to about 60% by weight, from about 20% to about 50% by weight, or from about 30% to about 40% by weight of the total composition. It may be preferred that the silicone substitute be present in an amount of about 1%, about 2%, about 3%, about 4%, about 5%, about 6%, About 7%, about 8%,
    Both the silicone substitutes and the personal care formulations included in the invention as described herein have final properties similar or identical to those of their equivalents containing usual silicone. In particular, the difference between a spreading value of a silicone mixture of the invention or a personal care formulation of the invention ("spreading value of the invention" Spreading of a customary silicone or customary silicone-containing personal care formulation ("usual spreading value") is less than about 10%, less than about 5%, less than about 1% of the d Total usual spreading. In addition, the sensation properties of the skin,
    EXAMPLE 1 Preparation of an Example of Non-Polymeric Ester of the Invention
    [0036] The reaction product of 1-heptanol and succinic acid ("diheptyl succinate") was prepared. To a five-necked four-necked flask equipped with a stirrer, hot-air heater, nitrogen gas bubbling, a steam column and a total condenser was added 2813 g 24.25 moles-grams) of n-heptanol. 938 grams (7.94 moles-grams) of succinic acid was added. To this was added 7.5 g of ethanesulfonic acid (70% aqueous solution) as catalyst.
    The mixture was heated to about 150 ° C, and a vacuum was slowly set in place. At the end of this step, the acid value of the material was measured to be 0.90 mg KOG / g. The mixture was then cooled to about 90 ° C and a sodium carbonate solution was added to neutralize the residual acidity.
    The ester was then distilled by batch followed by steam cleaning. The cleaned ester was treated with activated charcoal and filtered to obtain an essentially odorless and colorless fluid.
    Analytical properties of the ester are shown below in Table 1. TABLE 1
    Property Units Result
    Color APHA 23
    Acid value mg KOH / g 0.035
    Hydroxyl value mg KOH / g 0.25
    Odor Organoleptic Sweet
    Viscosity at 25 ° C cSt 8.6
    Viscosity at 40 ° C cSt 5.8
    Sp. Gr. 25/25 - 0.9338
    Flash point ° C 186
    Moisture% w / w 0.01 [0041] FIG. 1 represents the infrared spectrum of the non-polymeric ester prepared as described above.
    EXAMPLE 2 Preparation of Examples of Polymeric Esters of the Invention Variants of the reaction product of decanedioic acid ("sebacic acid" derived from castor oil 5), 1.2 , 3-propanetriol ("glycerol", derivative of coconut oil) and octanoic acid ("caprylic acid", derived from coconut oil) were prepared. Reagent quantities for each variant are given in Table 2.1 below.
    The esterification was carried out in a four-necked flask equipped with a stirrer, a balloon heater, a bubbling of nitrogen gas, a steam column and a Total condenser. In each case, the reagents were introduced into the vessel and heated to about 215 ° C.
    The pressure was then reduced to remove the reaction water and the acid value was monitored to follow the course of the reaction. When the reaction was sufficiently complete (acid value 5 mg KOH / g or less) the contents of the reactor were cooled to about 180 ° C and was steam cleaned under high vacuum for about four hours. Steam cleaning was stopped, and the reaction product was cooled and evacuated into containers. Table 2.2 shows the properties obtained.
    [0046] FIG. 2 represents the infrared spectrum of the exemplary GSC polymeric ester of type 4.
    Table 2.1
    Product Grade Glycerol Grams Sebacic Acid Grams GSC Type 1 1440 960 1600 GSC Type 2 1462 769 1269 GSC Type 3 1416 786 1298 GSC Type 4 1392 774 1334 GSC Type 5 1558 733 1209 GSC Type 6 1492 737 1271 Table 2.2
    Product Acid Value Hydroxyl Value Color (APHA) Moisture Viscosity (mg KOH / g) (mg KOH / g) (w / w%) (cP at 25 ° C) GSC Type 1 0.13 85.3 58 0.05 5900 GSC Type 2 0.26 45.4 309 0.025 3185 GSC Type 3 0.25 ND ND ND Gelated GSC Type 4 0.33 49.2 120 0.011 6200 GSC Type 5 0.91 26.1 188 0.026 2525 GSC Type 6 1.07 26.4 327 0.005 5100 Example 3 Preparation of an Example of The esters of Examples 1 and 2 were blended to make a total of about 1000 grams of test mixture by mixing in a glass beaker of appropriate size with a mechanical stirrer until the next- To obtain a clear, homogeneous solution. Six test mixtures were prepared to have the approximate viscosities of 10 cSt, 20 cSt, 50 cSt, 100 cSt, 200 cSt and 350 cSt,
    Table 3.1 shows the properties obtained for the exemplary silicone substitute of the invention.
    Table 3.1 GSC ID Type 4 DHS Viscosity at Flash Point Wt. Index Wt% (wt%) 25 ° C (cSt) (° C) Refraction 25/25 N10 2.0 98.0 10.0 195 1.4395 0.9356 N20 11.3 88.7 19.7 198 1.4417 0.9443 N50 27.5 72.5 53.8 206 1.4456 0.584 N100 32.5 67.5 109 200 1.4480 0.9691 N200 44.0 56.0 206 208 1.4507 0.9798 GSC Type 4 DHS Viscosity Flash Point (% By weight) 25 ° C (cSt) (° C) Refraction 25/25 N350 52.5 47.5 351 204 1.4529 0.9892 Example 4: A silicone substitute An evaluation of the spreading speeds of the silicone substitutes included in the invention as compared to the spreading speed of various dimethicones commonly used in personal care formulations was carried out.As is understood in the art, the spreading rate or spreading value is representative of the ability of the formulation to flow onto the skin upon application and is considered a significant measure in the determination Of the attributes of a final personal care formulation.
    Six samples of silicone substitute according to the invention (S1 to S6) prepared in Example 3 and six comparative samples of dimethicone fluid (CS1 to CS6) were evaluated, each with a variable viscosity, as shown in FIG. Table below: Comparative sample mix identifier.
    Samples 51 N10CS1 Dimethicone 10 is 52 N20 CS2 Dimethicone 20 is 53 N50 CS3 Dimethicone 20 is 53 N50 CS3 Dimethicone 50 is 54 N100 CS4 Dimethicone 100 is 55 N200 CS5 Dimethicone 100 is 55 N200 CS5 Dimethicone 200 is 56 N350 CS6 Dimethicone 350 is [ Mixture N10, N2O, N50, N100, N200, N350) were prepared according to the method described in Example 3. Each sample S1 to S6 and CS1 to CS6 was treated as follows: a piece of filter paper was placed on A Petri dish. Using a pipette, 50 L of the sample was applied approximately at the center of the filter paper. At the end of each of 1 minute, 3 minutes, 5 minutes, the circumference of the sample was plotted on the paper. The diameter of each circle created was measured. Two measurements were made for each sample at each time interval. The measurements are presented below. As plots, the measurements are shown in Fig. 3, by the viscosity.
    FIG. 3 Samples Mixing ID Comparative Samples 51 N10 CS1 Dimethicone 10 is 52 N20 CS2 Dimethicone 20 is 53 N50 CS3 Dimethicone 50 is 54 N100 CS4 Dimethicone 100 is 55 N200 CS5 Dimethicone 200 is 56 N350 CS6 Dimethicone 350 is Example 5 Comparison Sensation properties on the skin between mixtures of the invention and silicone fluids.
    Samples were prepared as follows, using the amounts of reagents as shown in the table in FIG. 4. Water in the amount indicated for phase A was heated to 78-80 ° C. Using a helix, the rest of the phase A ingredients were combined together into a mud and then mixed with the heated water. The combined "B" phase ingredients were heated to 80 ° C and added to "A" by continuing to mix. The entire mixture was allowed to cool to 60 ° C. A "C" phase was added to each batch and the whole mixture was cooled to room temperature.
    [0061] Four ounces (113.4 grams) of each formulation were packaged in a glass jar. Participants in the study were asked to apply 0.10 to 0.20 g of lotion on their inner forearm (one formulation on each arm). Participants were then asked to complete a survey. The statement is attached as an appendix as Fig. 5. The data produced from the readings are plotted in Fig. 6 (6A to 6D).
    The results of this study indicate that the silicone substitutes produce results similar to dimethicone equivalents.
    Six sample mixtures (S1 to S6) were created by combining 20 wt.% Lexorez 200 (an exclusive mixture of trimethylpentanediol / adipic acid / crosslinked glycerol polymer, available from Inolex Chemical Company, Philadelphia, PA , USA) and 80% by weight of each of samples S1 to S6, as shown below: Sample Sample Mixing ID # 51 N105 N2O53 N54 N10055 N200 56 N350 Lexorez 200 is A viscous polyester having a viscosity of about 25,000 cP at 25 ° C. Samples S1 to S6 were prepared according to the technique established in Example 3. Using a disposable transfer pipette, 0.20 g of Lexorez 200 was applied to the left side of a Petri dish and applied 0.20 g each of S1-S6 on the right side of the can. Each sample was manually spread to cover a circle with a diameter of 2 cm. A standard cotton ball (purchased from a beauty supply store) was placed on each sample circle. The cotton ball was pushed into the sample and then moved away using an upward movement. The amount of cotton fibers remaining on each sample circle was evaluated visually and recorded by photographic means.
    The photos created are shown in FIG. 7. In each case, the silicone substitutes of the invention have a reduced or weak tack (dry skin sensation) characteristic associated with silicones.
    EXAMPLE 6 Evaluation of the pigment grinding.
    The ability of the silicone substitutes to act as a pigment dispersant was evaluated by evaluating the viscosity and appearance of the pigment fragments. This capacity is important because high concentration, low viscosity pigment dispersions are used in color cosmetics.
    Nine test formulations were prepared by combining the ingredients as shown in the table below: ABCDEFGHI N10 50.00 N20 50.00 N50 50.00 N100 50.00 N200 50.00 N350 50.00
    Dimethicone 50 is 50.00
    Castor oil 50.00
    LexFeel 700 50.00
    Red Leather 7 50.00 50.00 50.00 50.00 50.00 50.00 50.00 50.00 50.00 LexFeel 700 is a mixture of pentaenthrity / heptanoate / caprylate / caprate available from Inolex Chemical Company, Philadelphia, PA, USA. Mixtures N10, N2O, N50, N100, N200, N350 were prepared as described in Example 3. The dimethicone / silicone substitute selected for testing was slowly mixed with the red lacquer pigment until the pigment Moistened to avoid losing pigment in a cloud of dust. The mixture was continued until the pigment was completely dispersed. The viscosity of each assay mixture A to I was measured using a Brookfield viscometer using a TD spindle and a Helipath support. The results are shown in FIG. 8.
    The data indicate that the silicone substitutes in the series are comparative to the silicone mixture and facilitate an acceptable pigment dispersion. The silicone substitute mixtures were easy to mix and the viscosities obtained were low.
    EXAMPLE 7 Evaluation of the Gloss The ability of the silicone substitutes to confer a gloss by comparison with dimethicone equivalents was evaluated, in particular on human hair. Silicones, both dimethicone and cyclomethicone, are commonly used to add gloss capabilities to hair styling products but often accumulate on the hair and do not decompose once washed into the environment. Test formulations A to L were prepared by mixing the ingredients for each as shown in the table below:
    ABCDEFGHI J KL
    Isododecane 80 80 80 80 80 80 80 80 80 80 80 80 N10 20 -------- ---
    Dimethicone-20 - - - - - - is N20 - - - - - - -
    Dimethicone 20 is N50
    Dimethicone 50 is N100
    Mixtures N10, N20, N50, N100, N200 and N350 were prepared as set forth in Example 3.
    [0073] Braids of virgin human hair were cut into thirteen 8 cm strips. Each braid was shampooed and rinsed with deionized water for one minute. Each braid was sprayed from one of the test formulations A to L, a remaining untreated braid. Each braid was wrapped around a 28 cm cylinder and allowed to air dry. To evaluate the brightness, the cylinder was placed on a flat surface at a distance of 1 meter from an electric light working lamp. All other light sources have been eliminated. The cylinder with braids was illuminated by electric light. A picture of the hair was taken and the bandwidth of the gloss was measured. The data collected are shown graphically in FIG. 9. On the basis of these data,
    EXAMPLE 8 Natural moisturizing lotion for the skin A natural moisturizing lotion for the skin is prepared using the silicone substitute according to the invention. The ingredients used in the formulation are shown in the table below
    Phase Ingredient Amount (% by Weight) A Water 70.15 A Panthenol 0.1 B Glycerin 5.0 B Microcrystalline Cellulose and Cellulose Gum 1.0 B Xanthan Gum 0.2 C Cetearyl Alcohol and Cetearyl Glucoside 5.0 C N100 (Example 3) 10.0 C Jojoba Esters 2.0
    Phase Ingredient Quantity (% by weight) C Cetyl alcohol 2.0 C Helianthus annus oil 3.0 C Tocopheryl acetate 0.1 C Caprylhydroxamic acid and glyceryl caprylate and 1.0 glycerine The ingredients of phase A are mixed and heated to 80 ° C. . The ingredients of phase C are premixed with each other and then added to the heated phase A mixture by helix mixing. The A / C mixture is heated to 80 ° C. The ingredients of phase B are premixed. When the A / C mixture is at 80 ° C, the A / C mixture is added to the premix of phase B by helical mixing. The mixture is continued until the entire formulation is uniformly mixed. The formulation is cooled to room temperature while the mixture is maintained.
    In the evaluation it was determined that the lotion had a pH of 5.82 at 25 ° C. and a Brookfield viscosity of 39 000 cPs at 25 ° C. and that the lotion had both a dry sensation Of the skin and a pigment dispersing ability similar to that of a lotion which contains dimethicone.
    EXAMPLE 9 Antiperspirant stick.
    [0080] An antiperspirant stick formulation is prepared from the substitute of the invention. The ingredients used in the preparation are given below:
    Phase Ingredient Amount (wt.%) A N5 (Example 3) 56.0 A Hydroxystearic Acid 10.0 B Talc 6.0 B Silica 4.0 B Aluminum Tetrachlorohydrex Zirconium / Glycine 26.0 The ingredients of phase A are mixed using moderate agitation By helix and heated to 80 ° C. Thereafter, each phase B ingredient is added individually to the A phase mixture while the temperature is maintained. Mixing is accomplished using moderate helix agitation. The final mixture is cooled to room temperature.
    The antiperspirant product obtained does not contain silicones, but has the properties of dry skin sensation and smooth application of the formulations containing cyclomethicone.
    EXAMPLE 10 Natural Lip Dye A natural lip coloring formulation is prepared from the substitute of the invention. The ingredients used in the preparation are given below:
    Phase Ingredient Amount (wt%) A N350 (Example 3) 37.30 A N5 (Example 3) 20.0 A Diamidon Phosphate 5.0 A Argnia Spinosa (Argan) Core Oil 1.5 A Triticum Vulgare (Wheat) Germ Oil 3.0 A Prunus Armeniaca Core Oil (Apricot) 2.0 A Copernica Cerifera Wax (Carnauba) 12.0
    Phase Ingredient Amount (% by weight) A Euprorbia Wax Cerifera (Candelilla) 4.0 A Maqnifera Indica (Mango) 2.0 Butter Butyrosperum Parkii (Shea Butter) 1.0 A Glyceryl Caprylate Glyceryl Undecylenate 0.8 B Mica Sericite 6.0 B Titanium dioxide 2.0 B Yellow lacquer 6 0.8 B Red lacquer 6 0.2 B Mica dioxide (and) Titanium 1.5 C Tocopheryl acetate, Vitamin E acetate 0.3 C Retinyl palmitate Vitamin A palmitate 0.3 C Fragrance 0.3 [0085 ] The ingredients of phase A are combined and heated to about 80 ° C to 85 ° C while undergoing helical mixing. The pigments of phase B are ground and then added to phase A. The mixture is mixed until it appears as visually uniform. The heat is removed, and the ingredients of phase C are added.
    In the evaluation, it was demonstrated that the formulation had a pH of 5.25 at 25 ° C. and a Brookfield viscosity of 82 000 cps. Furthermore, it is found that the lipid dye formulation provides spreading and skin sensing properties similar to those of dimethicone-containing formulations.
    EXAMPLE 11 Natural after-shampoo without silicone.
    [0088] A natural conditioner without silicone is prepared from the substitute of the invention. The ingredients used in the preparation are given below:
    Phase Ingredient Amount (wt%) A Water A Glycerin A Arginine B Brassicyl Isoleucinate Esylate (and) Brassica Alcohol B N350 (Example 3) 8.0 B Glyceryl Caprylate (and) Glyceryl Undecylenate 1.0 B Orbignya Speciosa Core Oil (And) 1.0
    Astrocaryum Murumuru seed butter To prepare the conditioner, the ingredients of phase A are combined and heated to 75 ° C. by mixing with a helix. Separately, the ingredients of phase A are combined by heating them also at 75 ° C. by mixing with a helix. Heat is removed and phase B is added to phase A. When the mixture has cooled to 35 ° C, the ingredients of phase C are added. The entire formulation is cooled to room temperature while mixing.
    Evaluation of the formulation demonstrates that it has a pH of 3.85 at 25 ° C. and a Brookfield viscosity of 35 000 cPs at 25 ° C. In addition, the conditioner gives the hair a sensation and a gloss comparable to formulations containing silicone.
    It will be appreciated by those skilled in the art that modifications could be made to the embodiments described above without departing from the broad inventive concept of these. It is understood, therefore, that the present invention
    权利要求:
    Claims (48)
    [1] 1. A silicone substitute for use in a personal care formulation comprising a mixture of at least one polymeric ester and at least one non-polymeric ester, the polymeric ester being an esterification reaction product of (i) at least A first dicarboxylic acid, (ii) at least one first monofunctional or monofunctional carboxylic acid, and (iii) glycerin or derivatives thereof; And the non-polymeric ester being an esterification reaction product of (i) at least one second dicarboxylic acid and (ii) at least one second monofunctional alcohol, the substituent being substantially free of silicone.
    [2] 2. A substitute as claimed in claim 1, wherein at least one of the first or second monofunctional alcohols is independently selected from monofunctional alcohols having from 1 to 25 carbon atoms.
    [3] 3. A substitute according to claim 1, wherein at least one of the first or second monofunctional alcohols is chosen independently from monofunctional alcohols having 1 carbon atom having 10 carbon atoms.
    [4] 4. A substitute according to claim 1, wherein at least one of the first or second monofunctional alcohols is independently selected from a monofunctional alcohol having 1 carbon atom, a monofunctional alcohol having 2 carbon atoms, a monofunctional alcohol having 3 carbon atoms, A monofunctional alcohol having 4 carbon atoms, a monofunctional alcohol having 5 carbon atoms, a monofunctional alcohol having 6 carbon atoms, a monofunctional alcohol having 7 carbon atoms, a monofunctional alcohol having 8 carbon atoms, a monofunctional alcohol having 9 Carbon monohydric alcohol, a monofunctional alcohol having 10 carbon atoms, a monofunctional alcohol having 11 carbon atoms, and a monofunctional alcohol having 12 carbon atoms.
    [5] 5. A substitute according to claim 1, wherein at least one of the first or second monofunctional alcohols is independently a straight chain monofunctional alcohol.
    [6] 6. A substitute according to claim 1, wherein at least one of the first or second monofunctional alcohols contains saturated carbon atoms.
    [7] 7. A substitute according to claim 6, wherein all the carbon atoms present in the at least one of the first or second monofunctional alcohols are saturated.
    [8] 8. A substitute according to claim 1, wherein at least one of the first dicarboxylic acid or the second dicarboxylic acid is independently selected from dicarboxylic acids having from 15 carbon atoms to 25 carbon atoms.
    [9] 9. A substitute according to claim 1, wherein at least one of the first dicarboxylic acid or the second dicarboxylic acid is independently selected from dicarboxylic acids having from 5 carbon atoms to 10 carbon atoms.
    [10] 10. A substitute according to claim 1 having a viscosity of about 10 mm 2 / s.
    [11] 11. A substitute according to claim 1, having a viscosity of about 20 mm 2 / s.
    [12] 12. A substitute according to claim 1 having a viscosity of about 50 mm 2 / s.
    [13] 13. A substitute according to claim 1, having a viscosity of about 100 mm 2 / s.
    [14] 14. A substitute according to claim 1 having a viscosity of about 200 mm 2 / s.
    [15] 15. A substitute according to claim 1, having a viscosity of about 350 mm 2 / s.
    [16] 16. A personal formulation which is substantially free of silicone, comprising a silicone substitute consisting essentially of a mixture of at least one polymeric ester and at least one non-polymeric ester, the polymeric ester being an esterification reaction product (I) at least one first dicarboxylic acid, (ii) at least one first monofunctional or monofunctional carboxylic acid and (iii) glycerin or derivatives thereof; And the non-polymeric ester being an esterification reaction product of (i) at least one second dicarboxylic acid and (ii) at least one second monofunctional alcohol and at least one additional personal care ingredient.
    [17] 17. The personal care formulation according to claim 16, wherein at least one of the first or second monofunctional alcohols is independently selected from monofunctional alcohols having from 1 to 25 carbon atoms.
    [18] The personal care formulation of claim 16 wherein at least one of the first or second monofunctional alcohols is independently selected from monofunctional alcohols having from 1 carbon atom to 10 carbon atoms.
    [19] 19. A personal care formulation according to claim 16, wherein at least one of the first or second monofunctional alcohols is independently selected from a monofunctional alcohol having 1 carbon atom, a monofunctional alcohol having 2 carbon atoms, a monofunctional alcohol having 3 atoms Carbon monohydric alcohol, a monofunctional alcohol having 4 carbon atoms, a monofunctional alcohol having 5 carbon atoms, a monofunctional alcohol having 6 carbon atoms, a monofunctional alcohol having 7 carbon atoms, a monofunctional alcohol having 8 carbon atoms, Monofunctional alcohol having 9 carbon atoms, a monofunctional alcohol having 10 carbon atoms, a monofunctional alcohol having 11 carbon atoms, and a monofunctional alcohol having 12 carbon atoms.
    [20] 20. The personal care formulation of claim 16, wherein at least one of the first or second monofunctional alcohols is independently a straight chain monofunctional alcohol.
    [21] 21. The personal care formulation according to claim 16, wherein at least one of the first or second monofunctional alcohols contains at least one saturated carbon atom.
    [22] 22. The personal care formulation of claim 16, wherein all carbon atoms present in the at least one of the first or second monofunctional alcohols are saturated.
    [23] 23. A personal care formulation according to claim 16, wherein at least one of the first dicarboxylic acid or the second dicarboxylic acid is independently selected from dicarboxylic acids having from 1 to 25 carbon atoms.
    [24] 24. The personal care formulation of claim 16 wherein at least one of the first dicarboxylic acid or the second dicarboxylic acid is independently selected from dicarboxylic acids having from 5 carbon atoms to 10 carbon atoms.
    [25] 25. The personal care formulation of claim 16, wherein all of the carbon atoms present in the at least one of the first or second dicarboxylic acids are saturated.
    [26] 26. The personal care formulation of claim 16, wherein the silicone substitute has a viscosity of about 10 mm2 / sec.
    [27] 27. A personal care formulation according to claim 16, wherein the silicone substitute has a viscosity of about 20 mm2 / s.
    [28] 28. The personal care formulation of claim 16, wherein the silicone substitute has a viscosity of about 50 mm2 / sec.
    [29] 29. The personal care formulation of claim 16, wherein the silicone substitute has a viscosity of about 100 mm2 / s.
    [30] The personal care formulation of claim 16, wherein the silicone substitute has a viscosity of about 200 mm2 / sec.
    [31] 31. The personal care formulation of claim 16, wherein the silicone substitute has a viscosity of about 350 mm2 / s.
    [32] 32. The personal care formulation of claim 16, wherein the at least one personal care ingredient is selected from a surfactant, flavoring agent, perfume, opacifying agent, colorant, wax, emulsifier, Fatty acid, oil, preservative, UV absorbent compound, detergent, foaming agents, stabilizers, pH modifiers, foaming agents, moisturizers, water, alcohol, urea, Wetting agent, hair or skin softener and solvent.
    [33] 33. The personal care formulation of claim 16, wherein the at least one personal care ingredient is selected from parabens, mineral oil, vegetable oil, olive oil, paraffin, PEG, Polyethylene, polyethylene glycol, polyoxyethylene, polyoxynol, petroleum jelly, laureth sodium sulfate, sodium laureth sulfate, sodium myreth sulfate, sodium oleth sulfate, ceteareth sodium sulfate, hydan- Tooth, sodium hydroxymethylglycinate, triethanolamine, diethanolamine cocamide, diethanolamine laurimide, diethanolamine linoleamide, diethanolamine oleamide, oxybenzone, essential oils, emollient, octylmethoxycinnamate, titanium dioxide, and The zinc oxide.
    [34] 34. The personal care formulation of claim 16, wherein the silicone substitute is present in an amount of from 1% to 95% by weight of the formulation.
    [35] 35. A personal care formulation according to claim 16, wherein the silicone substitute is present in an amount of from 5% to 80% by weight of the formulation.
    [36] 36. A personal care formulation according to claim 16, wherein the silicone substitute is present in an amount of from 10% to 30% by weight of the formulation.
    [37] 37. A personal care formulation according to claim 16, wherein the silicone substitute is present in an amount of about 3% by weight of the formulation.
    [38] 38. A process for preparing a personal care formulation which is substantially free of silicone comprising preparing a basic formulation and incorporating into the basic formulation a silicone substituent consisting essentially of at least one ester Polymer and at least one non-polymeric ester, the polymeric ester being an esterification reaction product of (i) at least one first dicarboxylic acid, (ii) at least one monofunctional monofunctional or monofunctional carboxylic acid and (Iii) glycerine or derivatives thereof, and the non-polymeric ester being an esterification reaction product of (i) at least one second dicarboxylic acid and (ii) at least one second monofunctional alcohol, Base comprising at least one of a surfactant, a flavoring agent, a perfume, an opacifier,A solvent, a colorant, a wax, an emulsifier, a fat, an oil, a preservative, a UV-absorbing compound, a detergent, A foaming agent, a stabilizer, a pH modifier, a moisturizer, water, an alcohol, a urea, a wetting agent, and a hair softener Or skin.
    [39] 39. The process of claim 38 wherein at least one of the first or second monofunctional alcohols is independently selected from monofunctional alcohols having from 30 carbon atoms to 25 carbon atoms.
    [40] 40. A process according to claim 38, wherein at least one of the first or second monofunctional alcohols is independently selected from monofunctional alcohols having 1 carbon atom having 10 carbon atoms.
    [41] 41. The process of claim 38, wherein at least one of the first or second monofunctional alcohols is independently selected from a monofunctional alcohol having 1 carbon atom, a monofunctional alcohol having 2 carbon atoms, a monofunctional alcohol having 3 carbon atoms, A monofunctional alcohol having 4 carbon atoms, a monofunctional alcohol having 5 carbon atoms, a monofunctional alcohol having 6 carbon atoms, a monofunctional alcohol having 7 carbon atoms, a monofunctional alcohol having 8 carbon atoms, a monofunctional alcohol having 9 Carbon monohydric alcohol, a monofunctional alcohol having 10 carbon atoms, a monofunctional alcohol having 11 carbon atoms, and a monofunctional alcohol having 12 carbon atoms.
    [42] 42. The method of claim 38, wherein at least one of the first or second monofunctional alcohols is independently a straight chain monofunctional alcohol.
    [43] 43. A process according to claim 38, wherein at least one of the first or second monofunctional alcohols contains at least one saturated carbon atom.
    [44] 44. A method according to claim 38, wherein all the carbon atoms present in the at least one of the first or second monofunctional alcohols are saturated.
    [45] 45. A process according to claim 38, wherein at least one of the first dicarboxylic acid or the second dicarboxylic acid is independently selected from dicarboxylic acids having a carbon atom of 25 carbon atoms.
    [46] 46. ​​The process of claim 38 wherein at least one of the first dicarboxylic acid or the second dicarboxylic acid is independently selected from dicarboxylic acids having from 5 carbon atoms to 10 carbon atoms.
    [47] 47. The process of claim 38, wherein all of the carbon atoms present in the at least one of the first or second dicarboxylic acids are saturated.
    [48] 48. The process of claim 38, wherein at least one of the carbon atoms present in the at least one of the first or second dicarboxylic acids is saturated.
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    同族专利:
    公开号 | 公开日
    JP2019065048A|2019-04-25|
    CN104114234A|2014-10-22|
    EP3360600A1|2018-08-15|
    EP2780083A1|2014-09-24|
    WO2013074655A1|2013-05-23|
    EP2780083B1|2021-07-28|
    US10292929B2|2019-05-21|
    US9610237B2|2017-04-04|
    EP2780083A4|2015-05-20|
    ES2885838T3|2021-12-15|
    PL2780083T3|2021-12-27|
    ES2884702T3|2021-12-10|
    JP2014533288A|2014-12-11|
    US20140356303A1|2014-12-04|
    PL3360600T3|2021-12-27|
    EP3360600B1|2021-08-11|
    CN104114234B|2019-07-23|
    CN109984956A|2019-07-09|
    US20170196796A1|2017-07-13|
    引用文献:
    公开号 | 申请日 | 公开日 | 申请人 | 专利标题
    DE3061696D1|1979-02-03|1983-03-03|Dynamit Nobel Ag|Fluid, biodegradable ester mixtures resistant to oxidation, with low cloud points, and their preparation|
    DE3810426A1|1988-03-26|1989-10-12|Bayer Ag|FOAM ABSORBER|
    DE19623383C2|1996-06-12|1999-07-01|Henkel Kgaa|Use of fatty substances as a silicone substitute for the production of cosmetic and / or pharmaceutical preparations|
    JP2000212049A|1999-01-18|2000-08-02|Shiseido Co Ltd|Hair cosmetic|
    JP2004262783A|2003-02-28|2004-09-24|Nippon Fine Chem Co Ltd|Cosmetic and imparting agent for touch similar to that of silicone|
    US20040241200A1|2003-05-19|2004-12-02|Daniel Winn|Personal care products that do not contain tetramer and/or pentamer cyclomethicones|
    US20040258642A1|2003-06-18|2004-12-23|Calello Joseph Frank|Cosmetic compositions|
    DE102004017222A1|2004-04-05|2005-10-20|Cognis Ip Man Gmbh|Sensory waxes for cosmetic and / or pharmaceutical formulations|
    US20050260150A1|2004-05-20|2005-11-24|Inolex Investment Corp.|Polyol polyester-containing personal care products that do not contain low viscosity silicone fluids|
    WO2006004911A2|2004-06-28|2006-01-12|Inolex Investment Corp.|Complex polyol polyester polymer compositions for use in personal care products and related methods|
    WO2009064790A1|2007-11-13|2009-05-22|Presperse, Llc|Silicon-free hydrocarbons providing aesthetic volatility|
    US8758736B2|2007-12-20|2014-06-24|L'oreal|Water-in-oil emulsion stabilized with a lipophilic emulsifier and a hydrophobically modified polysaccharide|
    ES2837139T3|2008-08-15|2021-06-29|Inolex Investment Corp|Natural compositions for personal care based on undecylenated ousters|
    US20100068162A1|2008-09-18|2010-03-18|Lipo Chemicals Inc.|Compositions Having Silicone Properties|
    US8715630B2|2009-09-15|2014-05-06|Dow Global Technologies Llc|Silicone replacements for personal care compositions|
    JP5273743B2|2010-03-05|2013-08-28|信越化学工業株式会社|Cosmetic composition and cosmetics|
    CN109984956A|2011-11-14|2019-07-09|伊诺莱克斯投资公司|The natural siloxanes substitute of siloxanes fluids in personal care formulations|US8992959B2|2010-12-10|2015-03-31|Medline Industries, Inc.|Articles having antimicrobial properties and methods of manufacturing the same|
    CN109984956A|2011-11-14|2019-07-09|伊诺莱克斯投资公司|The natural siloxanes substitute of siloxanes fluids in personal care formulations|
    US20150147375A1|2013-11-27|2015-05-28|Medline Industries, Inc.|Non-sticky antimicrobial medical articles|
    BR112016029241A2|2014-06-16|2017-08-22|Procter & Gamble|Method for treating hair with a concentrated conditioner|
    JP2017519011A|2014-06-16|2017-07-13|ザ プロクター アンド ギャンブル カンパニー|Method for treating hair using a concentrated conditioner|
    EP3154506A1|2014-06-16|2017-04-19|The Procter and Gamble Company|Method of treating hair with a concentrated conditioner|
    WO2016172407A1|2015-04-23|2016-10-27|The Procter & Gamble Company|Hair care conditioning composition|
    ITUB20153889A1|2015-09-25|2017-03-25|Bio Lo Ga Srl|Hydrophobic vitamin E-based gel free of silicone products for topical application|
    US10265251B2|2015-12-15|2019-04-23|The Procter And Gamble Company|Method of treating hair|
    WO2017106404A1|2015-12-15|2017-06-22|The Procter & Gamble Company|Method of treating hair|
    CN108367168A|2015-12-15|2018-08-03|宝洁公司|The method for handling hair|
    US10124951B2|2015-12-15|2018-11-13|The Procter And Gamble Company|Method of treating hair|
    CN108367169A|2015-12-15|2018-08-03|宝洁公司|The method for handling hair|
    EP3389597A1|2015-12-15|2018-10-24|The Procter and Gamble Company|Method of treating hair|
    US10294013B2|2015-12-21|2019-05-21|The Procter And Gamble Plaza|Package to dispense a foaming composition|
    JP6157659B1|2016-02-10|2017-07-05|イノレックス インベストメント コーポレイション|Synergistic compositions, formulations and related methods for reducing UV-induced lipid peroxidation|
    JP6960743B2|2016-02-29|2021-11-05|日本精化株式会社|Small molecule silicone alternative oil|
    US10835480B2|2016-04-22|2020-11-17|The Procter And Gamble Company|Method of forming a silicone layer|
    WO2017184794A1|2016-04-22|2017-10-26|The Procter & Gamble Company|Method of forming a silicone layer|
    MX2018013276A|2016-05-26|2019-03-28|Kimberly Clark Co|Anti-adherent compositions and methods of inhibiting the adherence of microbes to a surface.|
    WO2019113813A1|2017-12-13|2019-06-20|Beiersdorf Daily ChemicalCo. Ltd.|A hair cleansing composition|
    US11229589B2|2018-03-01|2022-01-25|Inolex Investment Corporation|Natural hydrocarbon/ester compositions with improved sensory properties, formulations and related methods|
    WO2020147934A1|2019-01-15|2020-07-23|Symrise Ag|Diester of plant-based 1,3-propanediol|
    IT201900003053A1|2019-03-01|2020-09-01|Agf88 Holding Srl|COSMETIC FORMULATION, PROCEDURE FOR ITS REALIZATION AND METHOD OF USE AS A COSMETIC TREATMENT FOR HAIR ALTERNATIVE TO SILICONES|
    EP3932440A1|2019-03-28|2022-01-05|TERUMO Kabushiki Kaisha|Medical device|
    WO2021046622A1|2019-09-11|2021-03-18|Maian Industria De Produtos Quimicos Ltda|Natural silicone replacement composition, production method and use thereof|
    法律状态:
    优先权:
    申请号 | 申请日 | 专利标题
    US201161559266P| true| 2011-11-14|2011-11-14|
    PCT/US2012/065052|WO2013074655A1|2011-11-14|2012-11-14|Natural silicone replacements for silicone fluids in personal care formulations|
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