WO2004096282A1 - Gel de melange hydrophile - Google Patents

Gel de melange hydrophile Download PDF

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Publication number
WO2004096282A1
WO2004096282A1 PCT/JP2004/006067 JP2004006067W WO2004096282A1 WO 2004096282 A1 WO2004096282 A1 WO 2004096282A1 JP 2004006067 W JP2004006067 W JP 2004006067W WO 2004096282 A1 WO2004096282 A1 WO 2004096282A1
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WO
WIPO (PCT)
Prior art keywords
gel
hydrophilic
xanthan gum
pep
blend
Prior art date
Application number
PCT/JP2004/006067
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English (en)
Japanese (ja)
Inventor
Junya Fujimori
Original Assignee
Junya Fujimori
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Junya Fujimori filed Critical Junya Fujimori
Priority to JP2005505915A priority Critical patent/JP4109286B2/ja
Publication of WO2004096282A1 publication Critical patent/WO2004096282A1/fr

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/0012—Galenical forms characterised by the site of application
    • A61K9/0014—Skin, i.e. galenical aspects of topical compositions
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
    • A61K47/10—Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
    • A61K47/36—Polysaccharides; Derivatives thereof, e.g. gums, starch, alginate, dextrin, hyaluronic acid, chitosan, inulin, agar or pectin
    • 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
    • A61K8/73—Polysaccharides
    • 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
    • A61K8/90—Block copolymers
    • 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
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
    • C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
    • C08B37/0006—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid
    • C08B37/0024—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid beta-D-Glucans; (beta-1,3)-D-Glucans, e.g. paramylon, coriolan, sclerotan, pachyman, callose, scleroglucan, schizophyllan, laminaran, lentinan or curdlan; (beta-1,6)-D-Glucans, e.g. pustulan; (beta-1,4)-D-Glucans; (beta-1,3)(beta-1,4)-D-Glucans, e.g. lichenan; Derivatives thereof
    • C08B37/0033—Xanthan, i.e. D-glucose, D-mannose and D-glucuronic acid units, saubstituted with acetate and pyruvate, with a main chain of (beta-1,4)-D-glucose units; Derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L5/00—Compositions of polysaccharides or of their derivatives not provided for in groups C08L1/00 or C08L3/00
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L71/00—Compositions of polyethers obtained by reactions forming an ether link in the main chain; Compositions of derivatives of such polymers
    • C08L71/02—Polyalkylene oxides
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/59—Mixtures
    • A61K2800/594—Mixtures of polymers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/74—Biological properties of particular ingredients
    • A61K2800/75—Anti-irritant
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2650/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G2650/28—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule characterised by the polymer type
    • C08G2650/58—Ethylene oxide or propylene oxide copolymers, e.g. pluronics

Definitions

  • the present study is a gel that can be used in the pharmaceutical, cosmetic, health food, and chemical industries, has low toxicity and skin irritation, has excellent stability for chemical substances in the gel, and has low viscosity. It relates to a hydrophilic blend gel that can be washed only with water. Background art
  • Gel bases used in the fields of pharmaceuticals and cosmetics are broadly classified into hydrophobic bases and hydrophilic bases. Ideally, these gel bases have low skin irritation, excellent ability to keep the chemicals in the gel stable, non-greasy, and easy to clean. Is desired.
  • hydrophilic bases have the advantages of being chemically inert, not reacting with pharmaceuticals, and not subject to rancidity. Although it is excellent in its ability to stably maintain chemicals such as drugs, it has the disadvantage that it is not practical because of its high viscosity and high adhesion to skin and clothing.
  • hydrophilic gel base material for example, hydroxypropyl pill methylcellulose (METROS 90 SH—400, Shin-Etsu Chemical Co., Ltd.), can handle a maximum gel concentration of 5 to 10 weight. / 0 has been reported.
  • carboxymethylcellulose sodium and lithium can handle only 1 gel weight. /. It is as follows.
  • carboxyvinyl polymers Hibis @ Ko 105, Wako Pure Chemical Industries
  • the gel's concentration is 5 weight by weight because it shows higher viscosity at a lower concentration than the above two gel bases. / 0 or less.
  • these hydrophilic gel bases have high adhesiveness to skin and mucous membranes, have a sticky property when used, and have a disadvantage that they are difficult to remove during washing.
  • An object of the present invention is to have excellent ability to stabilize drugs in a gel, to have low skin irritation, to be easy to handle even at high gel concentrations, to be non-sticky, to be easily removed from the skin, and to be hydrophilic. It is to provide a blend gel. Disclosure of the invention
  • Kishimei is a combination of xanthan gum and polyoxyethylene-polyoxy pi-pyrene glycol copolymer (including those containing ethylenediamine as a cross-linking molecule in the molecular structure), and polyoxyethylene-polyoxy'propylene glycol copolymer.
  • the compounding ratio of 1% to 95% with respect to the total polymer weight and heat treatment at a temperature higher than the structural transition temperature of xanthan gum has excellent ability to stabilize the drug in the gel and low skin irritation It is possible to provide a hydrophilic blended gel that is easy to handle even at a high gel concentration, does not stick, and is easily removed from the skin.
  • FIG. 1 is a graph showing the relationship between the mouth opening viscosity of the hydrophilic blend gel according to the present invention and the amount of xanthan gum mixed therein
  • FIG. 2 is a diagram illustrating 25 of cephalothin sodium in the hydrophilic blend gel according to the present invention. It is a figure which shows the result of the stability test in C, (A) is a figure which shows the residual ratio of cephalothin sodium 2 days after, and (B.) 4 days after. BEST MODE FOR CARRYING OUT THE INVENTION ''
  • the present inventors have conducted intensive studies to achieve the above object, and have reported many reports in recent years. “The stability of a chemical substance in a gel is not only the macroviscosity of the gel base, but also the stability of the gel. Depends on the gel mouth viscosity of the gel, which is closely related to the motility of water. A gel with a higher degree can keep the drug more stable (Sumie Yoshioka,
  • the inventor of the present invention concluded that the handling of the gel ⁇ removal from the skin depends on the viscosity of the Makco, but the stability of the chemical substance in the gel depends on the viscosity of the mouth, which meets both objectives.
  • the gel base is considered to be a base with low Macco viscosity and high Miku viscosity due to its low viscosity, so we do not stick to the pharmaceutical field and search for polymers to be the target gel base from a wide range of fields without sticking to the pharmaceutical field did.
  • a low-viscosity, low-adhesion hydrophilic blend gel is prepared by suspending and mixing the polyoxyethylene-polyoxypropylene dalicol copolymer (hereinafter referred to as PEP) with water and heating. was found to be able to be obtained. '
  • the method for preparing the hydrophilic blend gel according to the present invention is as follows. That is, a suspension or an aqueous solution is separately prepared for xanthan gum and ⁇ and ⁇ P, and both polymer solutions are mixed at an arbitrary weight ratio shown below, heated for a predetermined time, and cooled to room temperature.
  • the hydrophilic blend gel according to the present invention can be obtained.
  • a hydrophilic blended gel related to the present invention can also be obtained by preliminarily heating an aqueous solution or suspension of xanthan gum and adding PEP.
  • composition ratio of xanthan gum and PEP capable of producing the hydrophilic blend gel according to the present invention is preferably such that the blending amount of PEP is 1 ° / 0 to 95%, more preferably 1%, based on the total polymer weight. 0% to 90 ° /. It is.
  • the heating temperature must be higher than the structural transition temperature of xanthan gum. The reason is that the generation mechanism of the hydrophilic blend gel according to the present invention changes the xanthan gum from ⁇ -helical structure to / 3 random coil 'structure by heating And, because based on that is compatible with PEP molecular chain in its c
  • the structural transition temperature of xanthan gum reported by P. Ann ab 1 e et al. Is 1.2 weight. /.
  • the temperature is 51 ° C in an aqueous solution, but in a buffer solution or electrolyte solution, this temperature shifts to the higher temperature side and rises to 80 ° C or higher (P. Annableand PA William Ams, Macromol. 1994. vol 27. no. 15). That is, the heating temperature depends on the solvent used when preparing the present hydrophilic blend gel. For example, if the solvent is purified water and pH 7 phosphate buffer, 90 ° C to 95 ° C is preferred.
  • the heating time when heating at 90 ° C. is preferably 30 minutes to 90 minutes. It has been reported that heating xanthan gum at '95 ° C for 9 hours completely destroys the ⁇ - helical structure. The present inventor also mixed xanthan gum and PEP at a weight ratio of 1: 1 and 9 hours at 9 ⁇ . Upon heating, gelling did not occur even when the temperature was returned to room temperature. Therefore, severe temperature and time conditions that completely destroy the ⁇ -helix structure or xanthan gum molecular chains should be avoided.
  • the formation mechanism of the hydrophilic blend gel according to the present invention is based on the fact that the ordered ⁇ -helix structure of xanthan gum is changed to a random structure and is compatible with a polyester compound such as PEP. It is thought that there is. For this reason, the structure of the xanthan gum can be randomized. Even using a method such as sonication, the hydrophilic blend gel according to the present invention can be prepared.
  • PEP which can be used to produce the hydrophilic blend gel according to the present invention include all grades sold by each company (for example, Adeka Pluronics Ltd.
  • hydrophilic blend gel made by Asahi Jongka, PEP 101 made by Freund, Nippon Oil & Fats) Manufactured by Pronon 20S), and the resulting hydrophilic blend gel has a different Macco viscosity and microviscosity depending on the grade, so it can be selected appropriately according to the application. ⁇
  • the weight was 10 in consideration of this difference in grade, that is, the difference in the mixing ratio of dithylene oxide and pucopyrene oxide in PEP. /.
  • PEP containing dithylene oxide hereinafter referred to as 10% PEP, trade name: Adecapul Kou Nick L 121, Asahi Denka
  • 80 weight /.
  • the effect of the present invention was examined using a PEP containing ethylene oxide (hereinafter referred to as 80% PEP, trade name: Adeki Pluronic F68, Asahi Denka).
  • EPEP PEP containing ethylenediamine as a cross-linking base
  • xanthan gum is heated similarly to the above PEP.
  • a hydrophilic blend gel having low adhesion and high stability and low skin irritation can be produced.
  • hydrophilic blend gel having the same action and effect can be produced by using a polyether compound such as polyethylene glycol in addition to the above PEP.
  • the hydrophilic blend gel 'according to the present invention can be used alone as a hydrophilic ointment alone, or can be added as a gel base to other hydrophilic and oily ointment formulations.
  • the hydrophilic blend gel can be subjected to a treatment such as freeze-drying to remove water and be used as an additive such as a tablet or an injection as a powder.
  • xanthan gum is a food additive
  • polyoxyethylene-polyoxypropylene glycol '' copolymer ⁇ polyethylene glycol '' is safe and excellent as an additive for oral preparations.
  • Such a hydrophilic blend gel can also be used as a jewel for oral administration.
  • the hydrophilic blend gel according to the present invention has a feature that it is not sticky and is easy to clean, so that it is used as a hair dyeing gel, a hair gel, and a body gel applicable to the whole body. Is also possible.
  • EPEP has tertiary nitrogen in its molecular structure, it exhibits mild cation properties and is considered to be suitable as a carrier for anionic polymers (eg, genes).
  • anionic polymers eg, genes.
  • the application of PEP to gene therapy has already been reported, and it has been shown that PEP promotes gene transfer into muscle cells. Genetic details Since the application of cationic polymers is effective to promote the uptake into cells, EPEP is expected to be more useful in gene therapy than PEP. Therefore, it is considered that the xanthan gum ZE PEP blend genole of the present invention composed of EPEP can be used as a carrier for gene therapy.
  • this hydrophilic blend genole can be used as an extremely safe gel, or as an additive for pharmaceuticals, cosmetics, etc.
  • Xanthan gum powder and 10% PEP (Example 1), or 80. /. PEP (Example 2) or EPEP (Example 3) was placed in a pressure-resistant bottle at a weight ratio of 1: 1 respectively, and purified water was added to suspend the suspension. This suspension was heated in a warm bath at 90 ° C. for 1 hour to obtain a hydrophilic blend gel according to the present invention.
  • a comparative example was used as a gel base, which is a lip pipi-methyl cellulose (Comparative Example 1), a carboxybutyl 'polymer (Comparative Example 2), and a sodium carboxymethyl cellulose (Comparative Example 3).
  • the kinematic viscosity of these gels is measured with a capillary viscometer and the specific gravity of the gel is also measured! /, Converted to absolute viscosity. This value corresponds to the Mac mouth viscosity of the hydrophilic blend gel of the present invention.
  • the micro-mouth viscosity of the hydrophilic blended gel was determined by electron spin resonance (ESR) measurement by spin labeling using TEM POL as a spin labeling agent, and the results shown in Table 1 were obtained. . ⁇ table 1 ⁇
  • the Mac mouth viscosities of the hydrophilic blended gels are as follows: hydroxypropyl methylcellulose (Comparative Example 1), carboxybutyl polymer (Comparative Example 2), which is currently widely used as a gel base. And about 1/30 to 2/5 of the Macco viscosity of sodium carboxymethyl'cellulose (Comparative Example 3).
  • the viscosity of the mouth opening of the hydrophilic blended gel of the present invention was as high as or higher than that of the comparative gel.
  • hydrophilic blend gels have higher Mic viscosity than the existing hydrophilic gels shown in Experimental Example 1 (Comparative Example 13), regardless of the mixing ratio of xanthan gum. It is believed that the ability to stabilize the drug therein is also higher. Also, the microviscosity of the amphiphilic blend gel shown here tends to increase as the amount of xanthan gum blended decreases, and by increasing the blending ratio of PEP or EPEP, a more stable hydrophilic blended gel is prepared. We can see that we can do it.
  • Xanthan gum with a total gel concentration of 7% / '10% PEP blend gel was applied to 7 adult subjects who had no skin disease in their hands for 0.8 days as a hand cream for 7 days at noon and at bedtime. We had you use. Also, instruct the patient not to wash their hands for 2 hours after administration in the daytime, and before bedtime, apply the gel to both hands, then allow time for the skin to permeate and dry, and become sticky. Seconds to one minute), and when I went to bed, the results shown in Table 2 were obtained. That is, 7 days later, no one complained of skin irritation or hypersensitivity, but two people felt good xanthan-derived moisturizing and moisturizing properties. [Table 2]
  • the hydrophilic blend gel according to the present invention was obtained by using 7% hydroxypropylmethylcellulose gel (shown as 7% HPMC in the figure) and 7% carboxymethylcellulose sodium 7% CM CNa).
  • the 7% carboxyvinyl polymer gel (shown as 7% CP in the figure) is not a practical gel concentration due to its high viscosity and skin adhesion, as suggested by Experimental Examples 1 and 4. Had excellent stabilizing ability.
  • the ability to stabilize the drug of the 7% X an EPNOP hydrophilic hydrophilic gel showed a value as high as that of the ⁇ % CP gel.
  • the Xan / 10% PEP hydrophilic blend gel which is inferior in drug stabilizing ability at 7% total polymer concentration, has a total polymer concentration of 16%. It was shown that increasing the concentration to / ⁇ provided a stabilizing effect comparable to that of the 7% CP gel. In addition, the total polymer concentration was 23. /. It was clarified that the Xa11 / 10% PEP hydrophilic blend gel was more excellent in the ability to stabilize cephalothin sodium than the 7% CP gel when it was increased.
  • Xanthan gum which is a hydrophilic blend gel according to the present invention.
  • ⁇ polyoxyethylene-polyoxypropylene dalycol blend gel containing a steroid agent When the prepared ointment was administered to patients with atopic dermatitis, good results were obtained.
  • a total of 10 g was added by adding 8 g / 99 g of a 4% xanthan gum / polyoxyethylene-polyoxypropylene glycol blended gel to 1.0 g of propylene glycol and 0.1 g of hydrocortisone butyrate.
  • Xanthan gum / polyoxyethylene-polyoxypropylene glycol 'blend gel ointment containing 0.1% hydrocortisone butyrate was prepared and administered to the following patients. Case: 4-year-old boy
  • the eczema of both lower legs was applied to the ⁇ heart and used for one week. Compared to conventional steroid ointments, it spreads better, can be used widely in small quantities, and has good absorbency, so it is not sticky and clothes are not contaminated. In one week, dermatitis subsided, eczema crusted, and pruritus disappeared.
  • the xanthan / gum / polyoxyethylene / polyoxypropylene glycol copolymer blend gel or the xanthan gum / polyniter compound blend gel according to the present invention has low skin irritation and low viscosity and low adhesion. It is easy to handle, even at high gel concentrations, and can be removed from the skin only by washing with water without stickiness. For this reason, the hydrophilic blended gel of the present invention can be put to practical use at a higher concentration (20 weight / 0 or more) than the currently used hydrophilic gel. Excellent in stabilizing drugs and chemicals significantly.

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
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  • Pharmacology & Pharmacy (AREA)
  • Polymers & Plastics (AREA)
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  • Dermatology (AREA)
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  • Biochemistry (AREA)
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  • Emergency Medicine (AREA)
  • Inorganic Chemistry (AREA)
  • Materials Engineering (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
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Abstract

L'invention concerne le mélange d'une gomme de xanthane avec un copolymère de polyoxyéthylène/polyoxypropylène glycol (pouvant renfermer de l'éthylènediamine comme molécule de réticulation dans la structure moléculaire) selon un rapport pondéral donné, ledit mélange étant ensuite chauffé. Plus précisément, le copolymère de polyoxyéthylène/polyoxypropylène glycol est incorporé dans une quantité comprise entre 1 et 95 % en poids en fonction de tous les polymères et le mélange est chauffé à une température pas inférieure à la température de transition structurelle de la gomme de xanthane.
PCT/JP2004/006067 2003-05-02 2004-04-27 Gel de melange hydrophile WO2004096282A1 (fr)

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JP2005505915A JP4109286B2 (ja) 2003-05-02 2004-04-27 親水性ブレンドゲル

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JP2003-127111 2003-05-02
JP2003127111 2003-05-02

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2016188919A1 (fr) * 2015-05-22 2016-12-01 Mag S.R.L. Societa' A Responsabilita' Limitata Semplificata Composition cicatrisante sur la base de sédum téléphium et d'allantoïne

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS584711A (ja) * 1981-06-26 1983-01-11 コルゲ−ト・パ−モリブ・カンパニ− 歯みがき
JP2000053552A (ja) * 1998-08-07 2000-02-22 Nisshin Oil Mills Ltd:The 化粧料
JP2002512842A (ja) * 1998-04-24 2002-05-08 ユニバーシティー オブ マサチューセッツ ヒドロゲル・細胞組成物の発達誘導と支持
WO2002045686A2 (fr) * 2000-12-07 2002-06-13 Altana Pharma Ag Preparation pharmaceutique en pate comprenant un ingredient actif labile en milieu acide

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Publication number Priority date Publication date Assignee Title
GR79663B (fr) * 1981-06-26 1984-10-31 Colgate Palmolive Co
JPS6067404A (ja) * 1983-09-22 1985-04-17 Pola Chem Ind Inc 皮膜型パツク料
JPH07101848A (ja) * 1993-09-30 1995-04-18 Shiseido Co Ltd ジェル状セルフタンニング化粧料
JP3524272B2 (ja) * 1996-07-23 2004-05-10 伊那食品工業株式会社 キサンタンガムの改質方法及び改質キサンタンガム
JP2002114628A (ja) * 2000-10-12 2002-04-16 Kose Corp 化粧料

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS584711A (ja) * 1981-06-26 1983-01-11 コルゲ−ト・パ−モリブ・カンパニ− 歯みがき
JP2002512842A (ja) * 1998-04-24 2002-05-08 ユニバーシティー オブ マサチューセッツ ヒドロゲル・細胞組成物の発達誘導と支持
JP2000053552A (ja) * 1998-08-07 2000-02-22 Nisshin Oil Mills Ltd:The 化粧料
WO2002045686A2 (fr) * 2000-12-07 2002-06-13 Altana Pharma Ag Preparation pharmaceutique en pate comprenant un ingredient actif labile en milieu acide

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
ANNABLE P. ET AL: "Interaction in Xanthan-Glucomannan Mixtures and the Influence of Electrolyte", MACROMOLECULES, vol. 27, 1994, pages 4204 - 4211, XP000456656 *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2016188919A1 (fr) * 2015-05-22 2016-12-01 Mag S.R.L. Societa' A Responsabilita' Limitata Semplificata Composition cicatrisante sur la base de sédum téléphium et d'allantoïne

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JPWO2004096282A1 (ja) 2006-07-13

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