WO2002015850A1 - Preparation cosmetique et produit cosmetique basique - Google Patents

Preparation cosmetique et produit cosmetique basique Download PDF

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Publication number
WO2002015850A1
WO2002015850A1 PCT/JP2001/007151 JP0107151W WO0215850A1 WO 2002015850 A1 WO2002015850 A1 WO 2002015850A1 JP 0107151 W JP0107151 W JP 0107151W WO 0215850 A1 WO0215850 A1 WO 0215850A1
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Prior art keywords
cosmetic
carbon atoms
polymer
butene
product
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PCT/JP2001/007151
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English (en)
Japanese (ja)
Inventor
Tamiko Suga
Mitsuo Okamoto
Yuichi Tokumoto
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Nippon Petrochemicals Company Limited
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Publication of WO2002015850A1 publication Critical patent/WO2002015850A1/fr

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • A61K8/8105—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
    • A61K8/8111—Homopolymers or copolymers of aliphatic olefines, e.g. polyethylene, polyisobutene; Compositions of derivatives of such polymers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin

Definitions

  • the present invention includes a hydrogenated product of a putene polymer having a specific chemical structure, has excellent oxidation stability and low skin irritation, and is further characterized by being colorless, odorless, and inexpensive, and is particularly used as a basic cosmetic. Related to cosmetics with excellent properties. Background art
  • JP A 4 9 one 8 5 2 4 3 JP, 1 0 0 ° F ⁇ 4 Orefuin heavy which is hydrogenation treatment having a kinematic viscosity of 1 5 to 3 5 cSt at (3 7. 8 ° C)
  • a cosmetic composition blended with a synthetic oil for cosmetics consisting of coalescing is disclosed, and its properties include odorlessness, low cost, low irritation to animals and humans, and storage stability.
  • the present inventors have made intensive studies on the above points, molecular weight and molecular weight distribution of the polymer in c 4 unsaturated compounds containing Murrell hydrogenation treatment in cosmetic compositions
  • the hydrogenated product in a cosmetic containing a treated product of a ⁇ 4 olefin polymer, has a signal of 7 to 6 Oppm detected in 13 C-NMR measurement.
  • the ratio of the integrated value of the signal of the tertiary carbon atom to the integrated value of is 0.
  • the present invention relates to a cosmetic characterized in that at least one selected from the group consisting of olefin polymers having a carbon number of less than 0 and having 20, 24, 28 and 32 carbon atoms is a main component. .
  • the second of the present invention in the first invention, C 4 Orefin polymer, C 4 Monoo Refuin such a result by polymerizing containing Isobuten alone or Isoputen using a fluorine-containing compound as a polymerization catalyst, and the polymer 60% by mole or more of the cosmetic has a vinylidene terminal structure.
  • a third aspect of the present invention relates to the cosmetic according to the first or second aspect of the present invention, wherein the fluorine content of the C 4 olefin polymer is 1 O ppm or less.
  • a fourth aspect of the present invention relates to the cosmetic according to any one of the first to third aspects of the present invention, wherein the cosmetic mainly comprises a hydrogenated product having 24 and / or 28 carbon atoms. You.
  • a fifth aspect of the present invention relates to the cosmetic according to any one of the first to third aspects of the present invention, wherein the cosmetic mainly comprises a hydrogenated product having 20 and ⁇ Z or 24 carbon atoms. You.
  • a sixth aspect of the present invention relates to a basic cosmetic using the cosmetic according to any one of the first to fifth aspects of the present invention.
  • the polymer of the C 4 unsaturated compound according to the present invention has a carbon number of 20, 24, 28 and At least one selected from the group consisting of the 32 olefin polymers is the main component, and the hydrogenated one is the integral of the signal of 7-6 O ppm detected in the 13 C—NMR measurement.
  • the ratio of the integrated value of the signal of the tertiary carbon atom to the value is less than 0.08. (Hereinafter referred to as “butene oligomer hydride”)
  • 1 3 C-NM and R ratio of the integrated value of the signals of the tertiary carbon atoms against the integrated value of 7 and 6 O ppm of signal detected in the measurement can be determined by the following procedure.
  • Tertiary carbon atoms were determined by DEPT measurements.
  • the trimethylaminosilane (TMS) was defined as O ppm, and the integral value of signonole at 7 to 60 ppm was calculated.
  • the content of tertiary carbon atoms was calculated by the following equation.
  • the ratio of the integral value of the signal of the tertiary carbon atom being less than 0.08 means that the butene oligomer hydride of the present invention has, for example, 20 or 24 carbon atoms, such as heat or ultraviolet light. It means that it does not contain more than two tertiary carbon atoms per mole that are unstable to energy and easily decomposed or oxidized. As a result, the butene oligomer hydride of the present invention exhibits excellent oxidation stability.
  • oligomer hydride according to the present invention for example, isobutene alone or petroleum, naphtha, and a butadiene raffinate was divided butadiene 0-4 fractions produced by thermal decomposition of butane polymerized in a fluorine-containing catalysts as butene polymer, It can be obtained by hydrogenating the oligomer component contained therein.
  • the carbon number of the butene polymer according to the present invention obtained by this method is represented by 4n (n ⁇ 2, where n is a natural number) since no side reaction occurs in which a carbon atom is eliminated during the polymerization reaction. Therefore, it is possible to purify and separate those with a specific molecular weight by distillation without using any special equipment or technology. Therefore, since the butene oligomer hydride of the present invention does not contain any component having a carbon number of 19 or less that exhibits skin irritation, it has excellent oxidative stability as described above, has a low oxidative degradation rate, and has a low skin irritation. I have to show it It has the following features.
  • First tertiary carbon atoms is less carbon atoms 4 n to (n ⁇ 2 n is a natural number) of a Butenpori mer, Isoputen alone is are in the polymerisation zone with the reactor (reaction zone) is C 4 containing Isoputen
  • the fraction is supplied and polymerization is carried out using a fluorinated catalyst.
  • a stirring type or a loop type can be arbitrarily selected, and a plurality of reactors may be provided.
  • Raw materials for polymerization can be used isobutene alone or naphtha in ethylene plants, kerosene, gas oil, butadiene raffinate butadiene were excluded from C 4 fraction obtained from the cracker, such as butane.
  • This butadiene rafte is a hydrocarbon mixture comprising 1-butene, 2-butene, isopthene and butanes. More specifically, 1-butene is about 10 to 40% by weight, and 2-butene is about 1 to 10% by weight. 40 weight. / 0, Isoputen about 3 for 5-7 0% by weight, butadiene approximately 0. 5 wt 0/0 or less, and butanes to those containing from about 1 0 to 3 0% by weight.
  • the other monomer is not particularly limited as long as it is within this composition range, and may be four fractions contained in a decomposition component from a fluid catalytic cracking (FCC) unit.
  • FCC fluid catalytic cracking
  • butadiene raffinate having the above composition may be used.
  • the composition can be changed by distillation or by adding isopten to increase the concentration of isopten, or by reducing the concentration of 1-butene by a reaction such as catalytic hydroisomerization, or by chemical or physical manipulation. it can.
  • the content of isopten is large, and the water content in the polymerization raw material inhibits the activity of the catalyst, so that it is usually adjusted to 1 O ppm or less.
  • the fluorinated catalyst examples include boron trifluoride-based catalysts and catalysts obtained by contacting a divalent nickel compound with a hydrocarbylaluminum halide and trifluoroacetic acid, such as nickel-heptanoate, dichloroethylethyl and trifluorochloro. And those formed by interaction with acetic acid.
  • This divalent nickel-based fluorinated catalyst has been proposed in Japanese Patent Application Laid-Open No. 57-87366.
  • a boron trifluoride-based catalyst is used, but more preferably a complex catalyst using an oxygen-containing compound as a complexing agent.
  • Preferred as a complexing agent for boron trifluoride are water, alcohols, and dialkyl ethers, which may be used alone or in a mixture at an appropriate ratio.
  • the alcohols aliphatic or aromatic alcohols having 1 to 21 carbon atoms are suitable.
  • the hydrocarbon group may be linear, branched, alicyclic, or include a ring. Specific examples include methanol, ethanol, propanol, n-butanol, pentanole, hexanolone, heptanol, n-year-old lanthanum, n-nonanol, decanolone, benzyl alcohol, 1,4-butanediol, and the like. .
  • dialkyl ethers having the same or different aliphatic or aromatic hydrocarbon groups having 1 to 20 carbon atoms are preferable.
  • the hydrocarbon group may be linear, branched, alicyclic, or include a ring.
  • dimethinooleethenore methinoleethenoreethenore, getinoreethenore, meth7 repropinoleate nore, etinolepropinoleatel, dipropinoleatenole, dibutinoreetenele, methyl petite / Reetet / Les, Etchinolebutinoleethenore, Propinolebutynoleethenore, Dipentinole ethenore, Phenoinolemethinoleether, Phenyletinoletethenore, Difeninoleetether, Cyclohexinolemethinoleether, Cyclohex Xyllechnoletertel and the like.
  • the supply amount of the complexing agent is preferably 0.01 to 1, OO Om mol based on 1 mol of isopten in the raw material. If it is less than 0.03 mmol, the reaction hardly proceeds, and if it is more than 1, OO O mmol, side reactions such as isomerization and conversion occur, which is not preferable.
  • the supply amount of the catalyst is suitably 0.1 to 500 mmol as boron trifluoride with respect to 1 mol of isobutene. If the amount of catalyst supplied is less than 0.1 mmol, the reaction is difficult to proceed because the amount of catalyst is small, and if it is more than 50 O mmol, the cost of the catalyst increases and it is not economical, which is not preferable.
  • the boron trifluoride complex catalyst is prepared according to a conventional method. For example, it is prepared by blowing a predetermined amount of gaseous boron trifluoride while cooling a complexing agent that has been cooled to or below room temperature in advance. Alternatively, supply the catalyst and complexing agent separately into the reaction system to form a complex in the system May be.
  • the polymerization reaction temperature is preferably from 100 to 50 ° C, more preferably from 150 to 20 ° C. If the temperature is too low, the conversion of isobutene will be low, and if it is too high, side reactions such as isomerization and rearrangement will occur.
  • any of a batch system and a continuous system can be used.
  • the continuous type is more economical and more efficient, so the following is an example of the continuous type.
  • the contact time between the raw material and the catalyst is important, and in the present invention, it is preferably 5 minutes to 4 hours. If the contact time is less than 5 minutes, a sufficient conversion of isopten cannot be obtained, and if the contact time is more than 4 hours, economical loss is large and side reactions such as isomerization and rearrangement are promoted.
  • the catalyst is deactivated using a suitable deactivator, for example, water, alkaline water, alcohol, or the like. After removal of the catalyze the organic layer was neutralized, and water washed to remove unreacted C 4 components by distillation.
  • a suitable deactivator for example, water, alkaline water, alcohol, or the like.
  • the butene polymer produced by the above method has few tertiary carbon atoms, 60% or more of the unsaturated bonds in the polymer have a vinylidene structure, and all carbon atoms are 4 n (n ⁇ 2, where n is a natural number) Is represented by
  • the above-mentioned butene polymer contains residual fluorine derived from the catalyst at lppm or more in terms of fluorine atoms, and in some cases, hundreds of ppm.
  • This residual fluorine is an organic fluorine which is difficult to remove even if it is deactivated by a conventional method and subsequent washing with water, becomes hydrogen fluoride, corrodes the apparatus, and is not used in the subsequent hydrogenation reaction. Inhibits the reaction as a catalyst. Therefore, the fluorine concentration in the butene polymer is preferably 10 ppm or less.
  • the fluorine compound is removed by contacting with a treating agent containing an anolemminium atom. Fluorine atoms in the fluorine compound are fixed and removed in the treatment agent containing aluminum.
  • the specific method of removing the fluorine compound is described in detail in the patent (International Application No. PCT / JP00 / 011036).
  • the fluorine concentration in the butene polymer is reduced to 10 ppm or less.
  • the butene polymer is appropriately distilled to obtain a butene oligomer having 36 or less carbon atoms.
  • the amount of butene oligomer is 5 to 30% based on the butene polymer.
  • the butene oligomer obtained by the above distillation is chemically unstable due to the double bond at the polymer end. Therefore, a hydrogenation reaction is carried out to prevent the formation of skin irritating substances due to oxidation, generation of odor and discoloration as a saturated hydrocarbon.
  • the hydrogenation reaction is carried out by reacting with hydrogen at high temperature in the presence of a metal catalyst.
  • a metal catalyst a white metal, a genus of nickel, for example, copper, nickel, palladium, platinum or the like is used alone or in combination of two or more. Further, these metals may be used by adhering them to a carrier such as kieselguhr, alumina or silica.
  • the reaction type may be a continuous type or a batch type.
  • the reaction conditions are as follows: temperature is 65 to 250 ° C, hydrogen pressure is normal pressure to 10 O kgf / cm 2 (9.8 MPa), and catalyst is the amount as metal amount with respect Buteno oligomer, 0. 0 0 0 1 5 to 1.0 wt 0/0 are preferred. Whether or not the hydrogenation reaction has proceeded is determined by measuring the iodine value, and the iodine value should be less than 1.0 gI / 100 g.
  • the hydrogenated putene oligomer is appropriately distilled to obtain a fraction having a distillation temperature of 144 to 160 ° C / 6 to 7 nmiHg (8.0 to 9.3 hPa).
  • a distillation temperature 144 to 160 ° C / 6 to 7 nmiHg (8.0 to 9.3 hPa).
  • gas chromatography capillary column: HT-5, 12 m, temperature: 30 to 250 ° C, heated at 5 ° C / min
  • those with 20 carbon atoms were 95% or more. Occupy.
  • 70 were found to have 24 and 28 carbon atoms. / o or more is included.
  • the butene oligomers having 20 and / or 24 carbon atoms and 24 and / or 28 carbon atoms obtained by the above method can be used as cosmetics of the present invention in various cosmetic compositions.
  • the amount is determined according to the specific purpose. In particular, when incorporated into basic cosmetics, the effect is most effectively exhibited.
  • Examples of basic cosmetics include lotions (cleansing lotion, astringent lotion, flexible lotion, multi-layer lotion), creams (burnishing cream, moisture cream, eye cream, cleansing cream, massage cream, Mollient cream, nourishing cream, night cream, base cream, lip balm) Ningling lotion, no, lotion, body mouth, emollient lotion, milky lotion, nourishing lotion, moisture lotion, suntan lotion, cleansing milk, etc.), no.
  • Butadiene rice (butadiene extraction residue from ethylene crackers) containing isobutene was used as a raw material.
  • the composition of the raw material by gas chromatography is as follows (weight / 0 ).
  • the raw material was fed at a flow rate of 4 L / h into a continuous polymerization apparatus having an inner volume of 4 L, and boron trifluoride was supplied to 8.27 mniol per 1 mol of olefin in the raw material.
  • Getyl ether and ethanol were fed separately such that the molar ratio to boron trifluoride was 1.00 and 0.03, respectively.
  • the conversion of isobutene was 95%.
  • Activated alumina (trade name: PSG-D25, manufactured by PRO CATALYSE) dried under reduced pressure at 200 ° C for 2 hours in a fixed-bed container with a capacity of 10 Oml was ground to a particle size of 0.5 mm to 1. What was classified into 4 mm was filled.
  • the residual fluorine concentration determined by Wickbold-colorimetry after treatment was less than 1 ppm.
  • the iodine value of the hydrogenated butene oligomer after the reaction was less than 1. Og-I / 100 g, and all peaks indicating olefins observed before the reaction in 13 C-NMR measurement had disappeared. From the above results, it was confirmed that the hydrogenation reaction proceeded.
  • the oligomer hydride was analyzed by gas chromatography to find that the number of carbon atoms was all 20 and the ratio of tertiary carbon atoms determined by 13 C_NMR was 0.051.
  • the kinematic viscosity at 25 ° C was 13.2 cSt.
  • the subsequent steps were performed in the same manner as in Example 1 to obtain a putene oligomer monohydride having 16 to 35 carbon atoms.
  • the hydride of the butene oligomer had a tertiary carbon atom ratio of 0.121 as determined by 13 C-NMR, and a kinematic viscosity at 25 ° C. of 20.7 cSt.
  • Example 1 Gas chromatographic analysis was performed on the hydrogenated pentene oligomer of Example 1 and Comparative Example 1. Table 1 shows the composition of the number of carbon atoms determined by the first graph. Carbon several minutes cloth
  • the hydrogenated pentene oligomer of Example 1 had 100 mol% of those having 20 carbon atoms, whereas in Comparative Example 1, the components other than 20 carbon atoms accounted for 40% or more. Was included.
  • Example 1 and Comparative Example 1 were subjected to a heating test.
  • Table 2 shows the results of measuring the peroxide value and the acid value before and after heating. Table 2 Measurement results of peroxide value and acid value before and after the heating test
  • Oxidation stability test The oxidative stability test was performed according to the standard oil and fat analysis test method 2.5.1.2 CDM (Conductometric Determination Method) established by the Japan Oil Chemists' Society. This test method is equivalent to the AOCS Official Method Cdl2b-92 Oil Stability Index (OSI) established by the American Oil Chemists' Society (AOCS).
  • the CDM value is expressed as the elapsed time until a break point at which the value of the volatile decomposition product generated by oxidation is collected in water and the value of the conductivity is measured. The higher the CDM value, the higher the oxidation stability.
  • the test method is as follows. Connect the measurement vessel containing 5 Oml of ion-exchanged water and the reaction vessel containing 3 g of sample. 1 20 ⁇ 0.2 Put the above reaction vessel in a thermostatic chamber adjusted to 2 ° C, leave it for 10 minutes, then blow clean air at a flow rate of 2 OL / h and start measuring conductivity at the same time. The measurement is terminated when the rate reaches 300 S / cm.
  • the measurement temperature can be set to 100 ° C. or 140 ° C. depending on the magnitude of the CDM value.
  • Example 1 A CDM test was performed on Example 1 and Comparative Example 1. Table 3 shows the CDM value and the time when the conductivity of water reached 40 ⁇ S / cm. Table 3 CDM test results (1 40.C)
  • the material of Example 1 is a material having not only excellent oxidation stability but also a low oxidation deterioration rate. This is due to the low tertiary carbon atoms.
  • Table 4 shows the properties of Example 1 and Comparative Example 1.
  • the method for measuring “acidity and alkalinity” in the table is as follows.
  • the ratio of the integrated value of the signal of the tertiary carbon atom to the integrated value is the ratio of the integrated value of the signal of the tertiary carbon atom to the integrated value.
  • Example 2 Forty healthy males and females (19 males and 21 females) were tested, and 0.1 ml of the cosmetic oil (1) obtained in Example 1 was applied to the circular cloth part of the bandage for patch test, and the inner part of the upper arm was used. Affixed to As a control, only a bandage was applied in parallel. After 24 hours, skin symptoms were visually observed and evaluated. For the evaluation method, the presence or absence of symptoms (erythema, edema, blisters, etc.) was confirmed according to the following criteria of the Japan Patch Test Study Group.
  • Table 5 shows the results. Table 5 Results of 24 Hour Closed Patch Test From the results in Table 5, it can be seen that the putenoligomer hydride obtained in Example 1 is almost non-irritating.
  • Component B was added to Component A, and Component C was further added and mixed and dissolved.
  • the dye was added thereto, the mixture was cooled for 2 to 3 days, and the precipitate was adsorbed and filtered using an adsorbent.
  • the prototype was less susceptible to oxidative degradation than the conventional product, had less skin irritation, and had a refreshing feel to the skin.
  • Component ⁇ was heated to 70 to 75 ° C to dissolve it, and then filtered. While stirring this, after heating and dissolving in it at 73 to 78 ° C, the filtered component B was added. The mixture was emulsified with a high-speed homomixer, allowed to stand for defoaming, cooled, then added with a flavor at 55 to 60 ° C, and cooled to room temperature.
  • the pulverized and sieved pigment was added, mixed and dispersed at about 70 ° C., and then filtered. This was heated to 70 to 75 ° G in advance and dissolved, and then filtered component B was added, followed by stirring to emulsify. After defoaming, a fragrance was added at 55 to 60 ° C, and the mixture was cooled to room temperature.
  • the prototype was less susceptible to oxidative degradation than the conventional product, had less irritation to the skin, and had a refreshing feel to the skin.
  • the hydrated putene oligomer which is a main component of the cosmetic of the present invention, is excellent in oxidative stability, has a low oxidative deterioration rate, contains no skin irritating components, and is colorless. It is odorless and inexpensive. Cosmetics containing these are particularly suitable for basic cosmetics.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Dermatology (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Cosmetics (AREA)
  • Polymerization Catalysts (AREA)

Abstract

Préparation cosmétique contenant un produit d'hydrogénation d'un polymère d'oléfine C4, ce produit d'hydrogénation en spectrométrie par résonance magnétique nucléaire 13C émettant un signal à 7 à 60 ppm, dont la proportion de valeur intégrée est attribuable à un atome de carbone tertiaire par rapport à la valeur intégrée de ce signal inférieure à 0,08. Ce produit d'hydrogénation contient en tant qu'ingrédient principal au moins un élément sélectionné dans le groupe constitué par des polymères d'oléfine possédant 20, 24, 28 et 32 atomes de carbone respectivement. Produit cosmétique basique contenant cette préparation cosmétique. Cette préparation cosmétique et ce produit cosmétique basique présentent une stabilité excellente, ne contiennent aucuns ingrédients irritant la peau, sont incolores et inodores et sont également économiques.
PCT/JP2001/007151 2000-08-23 2001-08-21 Preparation cosmetique et produit cosmetique basique WO2002015850A1 (fr)

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JP2000-252164 2000-08-23
JP2000252164A JP4562882B2 (ja) 2000-08-23 2000-08-23 化粧料および基礎化粧品

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EP1617912B1 (fr) * 2003-04-16 2007-10-24 Cognis IP Management GmbH Composition cosmetique contenant une oligo-alpha-olefine
DE10317781A1 (de) * 2003-04-16 2004-11-04 Cognis Deutschland Gmbh & Co. Kg Poly-alpha-Olefin-haltige kosmetische Zusammensetzung
JP2011503192A (ja) * 2007-11-13 2011-01-27 プレスパース、エルエルシー 風合いおよび揮発性を付与するシリコンフリーな炭化水素類
JP6065424B2 (ja) * 2012-06-28 2017-01-25 日油株式会社 毛髪化粧料用揮発性油
JP2014065666A (ja) * 2012-09-24 2014-04-17 Nof Corp 皮膚外用剤用揮発性油
US9855201B2 (en) 2012-06-28 2018-01-02 Nof Corporation Volatile oil for cosmetics
KR101523568B1 (ko) * 2013-05-16 2015-05-28 대림산업 주식회사 반응성 폴리부텐 및 비반응성 폴리부텐의 선택적 제조장치 및 방법

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4061780A (en) * 1972-12-20 1977-12-06 Nichiyu Kagaku Co., Ltd. Cosmetic oil containing isobutylene
JPH0272107A (ja) * 1988-09-08 1990-03-12 Nippon Oil & Fats Co Ltd 化粧料
JPH02188518A (ja) * 1989-01-14 1990-07-24 Nippon Petrochem Co Ltd 整髪料
JPH02188519A (ja) * 1989-01-14 1990-07-24 Nippon Petrochem Co Ltd 整髪料

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Publication number Priority date Publication date Assignee Title
JPS536218B2 (fr) * 1972-12-20 1978-03-06

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4061780A (en) * 1972-12-20 1977-12-06 Nichiyu Kagaku Co., Ltd. Cosmetic oil containing isobutylene
JPH0272107A (ja) * 1988-09-08 1990-03-12 Nippon Oil & Fats Co Ltd 化粧料
JPH02188518A (ja) * 1989-01-14 1990-07-24 Nippon Petrochem Co Ltd 整髪料
JPH02188519A (ja) * 1989-01-14 1990-07-24 Nippon Petrochem Co Ltd 整髪料

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