US20030044370A1 - Resin powder for dermatologic composition, skin cleansing agent and cosmetic composition using the powder, and preparation process of the powder - Google Patents

Resin powder for dermatologic composition, skin cleansing agent and cosmetic composition using the powder, and preparation process of the powder Download PDF

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Publication number
US20030044370A1
US20030044370A1 US10/015,611 US1561101A US2003044370A1 US 20030044370 A1 US20030044370 A1 US 20030044370A1 US 1561101 A US1561101 A US 1561101A US 2003044370 A1 US2003044370 A1 US 2003044370A1
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Prior art keywords
resin
resin powder
powder
particles
particle size
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Abandoned
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US10/015,611
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English (en)
Inventor
Yuki Sasaki
Yasuo Matsumura
Takayoshi Aoki
Etsuo Tominaga
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Fujifilm Business Innovation Corp
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Fuji Xerox Co Ltd
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Assigned to FUJI XEROX CO., LTD. reassignment FUJI XEROX CO., LTD. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: AOKI, TAKAYOSHI, MATSUMURA, YASUO, SASAKI, YUKI, TOMINAGA, ETSUO
Publication of US20030044370A1 publication Critical patent/US20030044370A1/en
Priority to US11/850,034 priority Critical patent/US8518424B2/en
Abandoned legal-status Critical Current

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    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/81Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08JWORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J3/00Processes of treating or compounding macromolecular substances
    • C08J3/12Powdering or granulating
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/81Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • A61K8/8141Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • A61K8/8152Homopolymers or copolymers of esters, e.g. (meth)acrylic acid esters; Compositions of derivatives of such polymers
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/84Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • A61K8/85Polyesters
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00Preparations for care of the skin
    • A61Q19/10Washing or bathing preparations

Definitions

  • the present invention relates to a resin powder for a dermatologic skin composition.
  • the invention also relates to a skin cleansing agent and cosmetic composition containing the resin powder and a preparation process of the resin powder.
  • powder-containing cosmetic compositions such as foundation, eye shadow, baby powder, emulsion, antiperspirant powder and body shampoo
  • addition of a spherical resin powder and moreover an improvement in a resin to be added have conventionally been conducted in order to improve its smoothness and spreadability upon application, affinity to the skin and refreshing coolness after use.
  • the above-described spherical fine particles have a particle size distribution (CV) of 15% or less, meaning that the particles are almost truly spherical. So the cosmetic composition has good spreadability upon application, but skin adhesion or affinity to the skin necessary upon its application becomes insufficient, tending to cause makeup to comes off.
  • CV particle size distribution
  • Such spherical resin powder particles are usually prepared by emulsion polymerization or suspension polymerization, which method however markedly widens the particle size distribution of the resin powder and permits preparation of only truly spherical particles.
  • an object of the invention is to provide a resin powder for dermatologic composition capable of attaining sufficient spreadability and skin adhesion upon application of a cosmetic composition, a skin cleansing composition or the like to the skin.
  • Another object of the invention is to provide a skin cleansing composition containing the resin powder.
  • a still other object of the invention is to provide a cosmetic composition containing the resin powder.
  • the represent invention also relates to a cosmetic composition comprising the above-described resin powder for a dermatologic composition.
  • the present invention also relates to a skin cleansing composition comprising the above-described resin powder for a dermatologic composition.
  • the present invention further relates to a process for preparing the above-described resin powder for a dermatologic composition, which comprises preparing a dispersion of resin particles by emulsion polymerization and allowing the resin particles to undergo agglomeration.
  • FIG. 1 is a graph illustrating a relation between particle size and volume of resin particles.
  • resin particles have an average volume particle size of 2.0 to 20.0 ⁇ m, preferably 2.0 to 15.0 ⁇ m.
  • a cosmetic composition or skin cleansing composition containing resin particles having a particle size outside the above-described range is deteriorated in usability such as spreadability. Particularly when the particle size exceeds 20 ⁇ m, foreign body sensation appears upon use and, moreover, coming off of makeup may be brought about.
  • the volume DX means a value of D (particle size) where the straight line intersects the axis D.
  • the particles of the resin powder for dermatologic composition according to the invention have a shape factor SF1 of 110 to 140.
  • shape factor SF1 of resin particles as used herein means a value as defined by the following formula:
  • the shape factor SF1 is calculated by analyzing a microscopic image or scanning electron microscopic image by an image analyzer (“LUZEX III”, manufactured by Nireco Corporation), measuring the maximum length ML and projected area A of resin particles and substituting them in the above-described formula.
  • a surfaceness index of the resin particles is preferably 2.0 or less.
  • the term “surfaceness index” of the resin particles as used herein is defined by the following formula:
  • n means the number of particles in the channel of a Coulter counter
  • R is the diameter ( ⁇ m) of the channel of the Coulter counter
  • is a density of resin particles (g/cm 3 ).
  • Coulter counter as used herein means “TA-II” manufactured by Nikkaki Co.
  • the specific surface area measured is a BET specific surface area measured using “Flow Sorb 2300” manufactured by SHIMADZU CORP.
  • Flow Sorb 2300 manufactured by SHIMADZU CORP.
  • GSDp (number D 84/number D 16) 0.5
  • the number DX means a value of D (particle size) where the straight line crosses with the axis D.
  • a ratio (volumetric ratio) of particles having a volume particle size of 20 ⁇ m or greater is preferably 3% or less.
  • a ratio of particles having a volume particle size of 20 ⁇ m or greater is 3% or greater, the resulting composition does not smoothly spread on the skin and uniformity upon application tends to be lost. This tendency becomes eminent when the average volume particle size of the resin particles becomes smaller and the surfaceness index approaches 1.0.
  • the resin constituting the resin particles used in the invention preferably has a number-average molecular weight of 3000 to 20000.
  • number-average molecular weight as used herein means a molecular weight as measured using a molecular weight analyzer (“HLC-8120” manufactured by TOSOH CORP). Number-average molecular weights less than 3000 tend to cause agglomeration of resin particles and soften the resin, thereby interfering with usability and storage stability.
  • Number-average molecular weights exceeding 20000 tend to make the resin particles too hard, thereby interfering with usability and storage stability (described specifically, when these resin particles are incorporated in a cosmetic composition, the resulting composition is reduced in the affinity to the skin and imparts the skin with tautness).
  • the resin constituting the resin particles preferably has a weight-average molecular weight of 6000 to 100000.
  • weight-average molecular weight as used herein means a molecular weight as measured using a molecular weight analyzer (“HLC-8120”, trade name; manufactured by TOSOH CORP) with THF as a solvent. Weight-average molecular weights less than 6000 tend to cause agglomeration of resin particles and soften the resin, thereby interfering with usability and storage stability.
  • Number-average molecular weights exceeding 100000 tend to make the resin particles too hard, thereby interfering with usability and storage stability (described specifically, when these resin particles are incorporated in a cosmetic composition, the resulting composition is reduced in affinity to the skin and imparts the skin with tautness).
  • the resin constituting the resin particles preferably has a glass transition temperature of 40 to 100° C.
  • glass transition temperature as used herein means a temperature as measured using a differential scanning calorimeter (“DSC-50”, trade name; product of SHIMADZU CORP) at a heating rate of 10° C./min.
  • DSC-50 differential scanning calorimeter
  • the resin softens excessively and tends to interfere with usability and storage stability.
  • Glass transition temperatures exceeding 100° C. tend to make the resin particles too hard, thereby interfering with usability and storage stability (described specifically, when these resin particles are incorporated in a cosmetic composition, the resulting composition has reduced skin affinity and imparts the skin with tautness).
  • the resin powder according to the invention preferably has a compaction ratio of 0.6 or less.
  • compaction ratio means a value calculated by substituting loosely-packed apparent specific gravity X and tightly-packed apparent specific gravity Y, as measured by a powder tester manufactured by Hosokawa Micron Ltd, in the following formula:
  • the resin powder according to the invention preferably has a water content of 3 wt. % or less.
  • the water content is also an important factor influencing on the fluidity of the resin particles. Water contents of the resin powder exceeding 3 wt. % decrease dry touch feeling and tends to deteriorate spreadability upon application. Incorporation of a resin powder having a water content of 3 wt. % or less improves fluidity of a dermatologic composition containing it.
  • the water content can be measured in a known manner.
  • an acid value has an influence on the anti-greasiness of a resin and at the same time, on adhesion and agglomeration between resin particles and another substance.
  • the resin constituting the resin particles preferably has an acid value falling within a range of from 1.0 to 20 mg/KOH/g.
  • a cosmetic composition containing resin particles constituted by such a resin can be washed way by an ordinarily employed soap or face wash.
  • a cosmetic composition or cleansing composition containing them has appropriate adhesion strength and the resin particles do not agglomerate each other.
  • surface tension of a solution which is available by dissolving 1 g of the resin powder in 3 g of acetone, adding 25 g of deionized water to the resulting solution, and filtering off the precipitate thus formed, is preferably 20 mN or greater.
  • the surface tension is less than 20 mN, the amount of impurities increases, which tends to cause problems such as deterioration in storage stability, for example, generation of agglomerates upon storage, and emission of an offensive odor.
  • the upper limit of the surface tension of the solution is 70 mN, because surface tension of the solution never exceeds 70 mN.
  • the conductivity of the above-described solution is preferably 100 ⁇ S or less.
  • the conductivity exceeds 100 ⁇ S, the amount of impurities increases, which tends to cause problems such as deterioration in storage stability, for example, generation of agglomerates upon storage, and emission of an offensive odor.
  • the above-described solution preferably has a surface tension of 20 mN or greater and conductivity of 100 ⁇ S or less. If so, problems such as deterioration in storage stability, for example, generation of agglomerates upon storage, and emission of an offensive odor do not occur. Accordingly such resin powder is suited as a component of a dermatologic composition.
  • a resin to be used for resin particles of the invention include homopolymers of a monomer, for example, a styrene monomer such as styrene, p-chlorostyrene or ⁇ -methylstyrene, an acrylic monomer such as methyl acrylate, ethyl acrylate, n-propyl acrylate, lauryl acrylate or 2-ethylhexyl acrylate, a methacrylic monomer such as methyl methacrylate, ethyl methacrylate, n-propyl methacrylate, lauryl methacrylate or 2-ethylhexyl methacrylate, an ethylenically unsaturated acid monomer such as acrylic acid, methacrylic acid or sodium styrenesulfonate, a vinylnitrile such as acrylonitrile or methacrylonitrile, a vinyl ether such as
  • the resin powder of the invention has excellent spreadability and skin adhesion so that it is suitably added to various cosmetic compositions and skin cleansing compositions.
  • No limitation is imposed on the cosmetic composition or skin cleansing composition insofar as it is an ordinarily employed powder-containing composition.
  • Its formulation form is also not limited and examples include liquid, paste, O/W emulsion, W/O emulsion, gel, powder and solid.
  • Examples of the cosmetic composition include makeup cosmetic compositions such as foundation, lipstick, powder lip, lip gloss, cheek rouge, eye shadow, eye liner, mascara and dusting powder, baby powder, shaving lotion, shaving foam, calamine lotion, emulsion, cream, ointment, peel-off pack, antiperspirant, deodorant, hair treatment agent, permanent wave formulation, hair dye, hair setting lotion, hair tonic, hair growth tonic and baldness remedy.
  • Examples of the cleansing composition include face wash cream, face wash powder, body shampoo, hair shampoo and hair rinse.
  • the resin powder for dermatologic composition according to the invention is preferably prepared by emulsion polymerization & agglomeration method.
  • the resin powder is obtained by washing and drying the thus-obtained fused particles.
  • suction filtration and pressure filtration are preferred for productivity.
  • No particular limitation is imposed on the drying method, but vacuum lyophilization, jet flash drying, fluid drying and oscillation type fluid drying are preferred.
  • the resin powder of the invention may have another fine particles attached to the resin particles (resin particles having fine particles adhered to the surface thereof will hereinafter be called “fine-particle-adhered resin particles”).
  • fine-particle-adhered resin particles it is possible not only to prevent re-agglomeration of fine particles, but also to permit exhibition of a function derived from the fine particles while maintaining the usability derived from the resin particles.
  • the size of the fine particles to be adhered to the resin particles depends on their amount to be adhered and the size of the resin particles. Particularly preferred is use, in combination, of resin particles and fine particles to satisfy the following formula: (particle size of resin particles)/(particle size of fine particles) ⁇ 2. At this ratio less than 2, adhesion strength of fine particles to the resin particles tends to lower.
  • Examples of the ultraviolet screening agent include inorganic compounds such as titanium oxide and cerium oxide and organic compounds such as benzophenone, benzotriazole and salicylic acid salts.
  • Examples of the infrared ray shielding agent include titanium oxide, zirconium oxide and silicon carbide, and compounds thereof.
  • the resulting dermatologic composition or cosmetic composition acquire synergistic effects. Described specifically, the composition can exhibit functions (fluidizing function, ultraviolet-ray absorbing function and storage-stability improving function) derived from the metal compound fine particles while maintaining smoothness, spreadability and skin affinity of the resin particles.
  • metal oxides ordinarily employed as a raw material for cosmetic compositions are usable and examples include, but not limited to, silicon dioxide, iron oxide (red oxide, black iron oxide), zirconium oxide and aluminum oxide.
  • a weak adhesive strength ratio of fine particles to the resin particles is preferably 90% or less.
  • the term “weak adhesive strength ratio” as used herein means a ratio, to the amount of the metal compound in the whole resin powder, of the amount of the metal compound in a supernatant obtained by dispersing 2 g of a resin powder composed of fine-particle-adhered resin particles and a trace amount of a surfactant in 40 g of pure water, applying ultrasonic wave for 1 minute at 50 micron-ampere by an ultrasonic oscillator inserted in the dispersion and then centrifuging the dispersion. It expresses the adhesive strength of the fine particles to the resin particles.
  • the amount of the metal compound in the supernatant and that in the whole resin powder composed of fine-particle-adhered resin particles can be determined by element analysis using fluorescent X-rays.
  • a weak adhesive strength ratio as defined above exceeds 90%, usability of the dermatologic composition such as cosmetic composition or skin cleansing composition tends to lower because of weak adhesive force of the fine particles to the surface of the resin particles. In addition, there is a potential danger that the fine particles released from the resin particles may have an influence on another component.
  • a weak adhesive strength ratio is preferably 50% or less.
  • a weight ratio of the fine particles to the resin particles usually falls within a range of 0.1 to 90 wt. %, preferably 0.1 to 60 wt. %.
  • the weight ratio is less than 0.1 wt. %, the fine particles do not tend to exhibit their functions fully because of their small content. Addition of them in an amount exceeding 90 wt. % does not increase the content of the fine particles relative to the resin particles because the fine particles flake off.
  • the amount of the resin powder to be incorporated in the cosmetic composition or skin cleansing composition differs with its using purpose, the amount usually ranges from 0.1 to 90 wt. %, preferably 0.5 to 60 wt. %. At an amount less than 0.1 wt. %, effects of the resin powder do not appear readily, while even at an amount exceeding 90 wt. %, effects of the resin powder given to the cosmetic composition or cleansing composition do not increase in proportion.
  • the other components to be incorporated therein are selected according to the using purpose of the cosmetic composition and are not limited specifically.
  • examples include inorganic powders such as talc, kaolin, mica, sericite, magnesium carbonate, calcium carbonate, aluminum silicate, barium silicate, calcium silicate, magnesium silicate, magnesium, silica, zeolite, barium sulfate and calcium phosphate, organic powders such as silicone resin powders and cellulose powders, pearlescent pigments such as titanium dioxide, zinc oxide, iron oxide, iron titanate, yellow oxide, carbon black, titanium monoxide, bismuth oxychloride and fish scale guanine, metal powder pigments such as aluminum powder and copper powder, organic pigments such as Red No.
  • the resin powder may be incorporated after treatment with silicone, metal soap, fatty acid, surfactant, acid, alkali or inorganic salt, or combination thereof.
  • Examples of a further component to be incorporated in a cosmetic composition or skin cleansing composition include hydrocarbons such as squalane, vaseline and liquid paraffin, oils such as higher fatty acids or oils and fats including camellia oil and olive oil, esters, and higher alcohols, surfactants, antiperspirants, bactericides, water, antiseptics and thickeners.
  • hydrocarbons such as squalane, vaseline and liquid paraffin
  • oils such as higher fatty acids or oils and fats including camellia oil and olive oil, esters, and higher alcohols
  • surfactants such as antiperspirants, bactericides, water, antiseptics and thickeners.
  • the cosmetic composition or skin cleansing composition of the invention can be prepared in a conventional manner.
  • the glass transition temperature was measured using a differential scanning calorimeter (“DSC-50”, trade name; product of SHIMADZU CORP.) at a heating rate of 10° C./min.
  • DSC-50 differential scanning calorimeter
  • the compaction ratio was calculated by substituting loosely packed apparent specific gravity X and tightly packed apparent specific gravity Y, as measured by a powder tester (product of Hosokawa Micron), in the following formula:
  • Compaction ratio (tightly packed apparent specific gravity Y ⁇ loosely packed apparent specific gravity X)/(tightly packed apparent specific gravity Y).
  • the water content was calculated by accurately weighing (W1) 1 g of a resin powder, drying it at 110° C. for 1 hour in a drier, taking it out from the drier, measuring the drying loss (W2) and substituting (W1) and (W2) in the following formula:
  • a volatile content was measured by adding 2 parts by weight of 2-propanol to 1 part by weight of the resin powder, dispersing the mixture for 30 minutes by ultrasonic wave, storing it in a refrigerator (5° C.) for at least one day, conducting solvent extraction, analyzing the supernatant by gas chromatography (“GC-14A”, trade name; product of SHIMADZU CORP.) and determining the volatile content in the resin powder.
  • GC-14A gas chromatography
  • Carrier gas He (2.5 kg/cm 2 )
  • Air flow rate 0.5 kg/cm 2
  • W weight (g) of a resin powder accurately weighed
  • S is an using amount (ml) of KOH
  • B is a using amount (ml) of KOH in measurement of blank
  • f is the factor of OH.
  • Liquids A and B were mixed, each 50 parts by weight, and mixed in a stirrer to obtain a suspension. The solvent was then distilled off under reduced pressure. To the residue was added 10 parts by weight of 6N hydrochloric acid and calcium carbonate was removed. By washing with water, drying and classification, a resin powder having an average particle size of 7.6 ⁇ m were obtained.
  • a resin powder was prepared in a similar manner to Examples 1 to 7 except for decreasing the spherizing time to 5 hours.
  • the resin powder thus obtained was measured for average volume particle size, average volume particle size distribution GSDv, shape factor SF1, surfaceness index, average number particle size distribution GSDp, volume, a ratio of particles having a volume particle size of 20 ⁇ m or greater, number-average molecular weight, weight-average molecular weight, glass transition temperature, compaction ratio, water content, volatile content, acid value, surface tension and conductivity.
  • the results are shown in Table 3.
  • a polyester polymer (terephthalic acid/bisphenol A propylene oxide adduct/cyclohexanedimethanol) was kneaded in an extruder.
  • the slab thus obtained was rolled and cooled, followed by pulverization by a hammer mill and then a jet mill.
  • the resulting powder was classified by an air classifier and crude and fine powder particles were removed, whereby a resin powder was obtained.
  • the resin powder thus obtained was measured for average volume particle size, average volume particle size distribution GSDv, shape factor SF1, surfaceness index, average number particle size distribution GSDp, a ratio of particles having a volume particle size of 20 ⁇ m or greater, number-average molecular weight, weight-average molecular weight, glass transition temperature, compaction ratio, water content, volatile content, acid value, surface tension and conductivity.
  • Table 3 The results are shown in Table 3.
  • the amount of the metal compound in the supernatant obtained by centrifugation of the resulting dispersion and the amount of the metal compound in the whole fine-particle-adhered resin particles were determined by a fluorescent X-ray analyzer (“SFT-1500”, trade name; product of SHIMADZU CORP).
  • the resin powder for dermatologic composition according to the invention makes it possible to attain sufficient spreadability and adhesion upon application.
  • the skin cleansing composition of the invention sufficient spreadability and adhesion upon application can be attained, leading to an improvement in usability.
  • a slight amount of the skin cleansing composition remains on the skin surface even after it is washed away, and as a result, the skin surface has a smooth feeling.

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US10/015,611 2001-08-17 2001-12-17 Resin powder for dermatologic composition, skin cleansing agent and cosmetic composition using the powder, and preparation process of the powder Abandoned US20030044370A1 (en)

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JP2001248322A JP3608537B2 (ja) 2001-08-17 2001-08-17 皮膚外用組成物用樹脂粉体、これを用いた皮膚洗浄料及び化粧料並びに皮膚外用組成物用樹脂粉体の製造方法
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US20040266926A1 (en) * 2003-06-27 2004-12-30 Fuji Xerox Co., Ltd. Resin powder for cosmetic and cosmetic using the same
CN111212629A (zh) * 2017-10-13 2020-05-29 科丝美诗株式会社 包含基于丙烯酸酯的共聚物的眼妆组合物

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JP3596533B2 (ja) * 2002-03-14 2004-12-02 富士ゼロックス株式会社 固形粉末化粧料
JP3596534B2 (ja) 2002-03-14 2004-12-02 富士ゼロックス株式会社 乳化化粧料
JP5974825B2 (ja) * 2012-10-26 2016-08-23 住友ベークライト株式会社 低発塵性粉末樹脂混合物の製造方法および成形品の製造方法
ES2643506T3 (es) * 2012-03-07 2017-11-23 Sumitomo Bakelite Co., Limited Método para producir un artículo de resina moldeado, y artículo moldeado de resina producido de este modo
CA3026108A1 (fr) 2016-06-10 2017-12-14 Clarity Cosmetics Inc. Formulations non comedogenes de soin des cheveux et du cuir chevelu et methode d'utilisation

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TWI280145B (en) 2007-05-01
KR20030015816A (ko) 2003-02-25
JP2003055153A (ja) 2003-02-26
DE10200749A1 (de) 2003-02-27
FR2828688A1 (fr) 2003-02-21
KR100599543B1 (ko) 2006-07-13

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