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
  • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
  • A61K8/55—Phosphorus compounds
  • A61K8/553—Phospholipids, e.g. lecithin
• • 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
  • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
  • A61K8/55—Phosphorus compounds
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
  • A61Q1/00—Make-up preparations; Body powders; Preparations for removing make-up
• • 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
• • 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
  • A61K2800/10—General cosmetic use

Definitions

• the present invention relates to a cosmetic base comprising a phosphorylcholine-like group-containing compound, and a cosmetic containing the cosmetic base.
• a gemini-type surfactant is a multi-chain, multi-hydrophilic group-type amphiphilic substance that has multiple hydrophobic chains and hydrophilic groups in one molecule.
• features of gemini-type surfactants include: (i) high surfactant activity typified by low critical micelle concentration and low Kraft point, (ii) high molecular association that easily forms higher-order structures such as vesicles, and (iii) ) Good cleaning performance such as antibacterial, wettability, antifoaming, metal ion resistance, and permeability. Due to these useful functions, gemini-type surfactants are widely used in various industrial fields including the cosmetics industry.
• Non-Patent Document 1 reports on the synthesis of a gemini-type surfactant having a phosphorylcholine-like group as a hydrophilic group and its solution physical properties, and discloses that the surfactant has excellent interfacial properties.
• Patent Documents 1 and 2 report that a gemini-type compound having a phosphorylcholine-like group has a moisturizing effect such as high detergency or high percutaneous absorption promotion and excellent barrier function. ing.
• gemini-type surfactants disclosed in these publications have a hydrophobic chain of a hydrocarbon group, and when the chain length is long, they are poorly soluble in water and oily ingredients, and therefore cannot be blended in cosmetics. In addition, there is a problem that after applying the blended cosmetic to the skin, a hard film feeling occurs. On the other hand, when the hydrophobic chain length is short, although the solubility in water and oil is improved, it is still insufficient, and there is a problem that the cosmetic containing the compound has poor stability at high temperatures. .
• Patent Documents 3 to 5 by introducing a highly hydrophilic amide bond into a part of the hydrophobic chain of a compound having a phosphorylcholine-like structure, it has a long-chain hydrocarbon group, but has good water solubility, interface A compound having an active ability and an excellent feeling of use has been proposed.
• the amide group of this compound is too hydrophilic, when it is used as a cosmetic base, it does not have sufficient emulsification stability at high temperatures. There was a problem that the feeling was generated.
• JP 2001-262184 A Japanese Unexamined Patent Application Publication No. 2011-213602 JP 2012-201617 A JP 2013-1644 A JP 2013-1645 A
• the object of the present invention is to have excellent solubility in oily components, maintain emulsification stability at high temperatures when blended in cosmetics, and give a feeling of crushed oil droplets during application and no hard film feeling.
• a cosmetic base comprising a phosphorylcholine-like group-containing compound having a specific structure has excellent solubility in oily ingredients, and that the cosmetic base can be used in cosmetics.
• the present invention was completed based on the discovery that when blended, the emulsification stability at high temperatures is dramatically improved, and that the feeling of oil droplets being crushed during application provides a good feeling of use without a hard film feeling. came to. That is, the present invention is shown below.
• a cosmetic base comprising a phosphorylcholine-like group-containing compound represented by formula (1).
• R 1 and R 2 in formula (1) each independently represent a hydrocarbon group having 12 to 22 carbon atoms, and R 3 is CH 3 or (CH 2 CH 2 O) n —H (n is 1 to is an integer of 30), provided that one of R 1 and R 2 is an unsaturated hydrocarbon group having 18 carbon atoms)
• R 1 and R 2 are independently represent a hydrocarbon group having 12 to 22 carbon atoms, and R 3 is CH 3 or (CH 2 CH 2 O) n —H (n is 1 to is an integer of 30), provided that one of R 1 and R 2 is an unsaturated hydrocarbon group having 18 carbon atoms
• the cosmetic base comprising the phosphorylcholine analogous group-containing compound of the present invention has excellent solubility in oily ingredients, maintains emulsion stability at high temperatures when blended in cosmetics, and can be applied when blended in cosmetics. It is useful as a cosmetic for skin and hair because it has a good texture without a hard film feeling and a feeling of crushed oil droplets at times.
• the cosmetic base of the present invention comprises a phosphorylcholine-like group-containing compound represented by formula (1).
• the phosphorylcholine-like group-containing compound represented by formula (1) may be simply referred to as "PC compound”.
• R 1 and R 2 in formula (1) each independently represent a hydrocarbon group having 12 to 22 carbon atoms, and R 3 is CH 3 or (CH 2 CH 2 O) n —H (n is 1 to is an integer of 30), provided that one of R 1 and R 2 is an unsaturated hydrocarbon group having 18 carbon atoms)
• R 1 and R 2 are each independently a hydrocarbon group having 12 to 22 carbon atoms.
• the hydrocarbon group having 12 to 22 carbon atoms is a saturated hydrocarbon group or an unsaturated hydrocarbon group, and may be linear, branched or cyclic.
• one of R 1 and R 2 is an unsaturated hydrocarbon group having 18 carbon atoms.
• the other of R 1 and R 2 is not an unsaturated hydrocarbon group.
• one of R 1 and R 2 is an unsaturated hydrocarbon group having 18 carbon atoms and the other is a saturated hydrocarbon group having 12 to 22 carbon atoms.
• R 1 is a saturated hydrocarbon group with 12 to 22 carbon atoms and R 2 is an unsaturated hydrocarbon group with 18 carbon atoms.
• R 1 is a saturated hydrocarbon group having 18 to 22 carbon atoms and R 2 is an unsaturated hydrocarbon group having 18 carbon atoms.
• R 1 and R 2 are unsaturated hydrocarbon groups.
• the emulsification stability at high temperatures is poor.
• the number of carbon atoms in R 1 and/or R 2 is less than 12, the emulsification stability at high temperature is deteriorated when the PC compound is used in cosmetics. However, when blended in cosmetics, a hard film feeling is expressed.
• saturated hydrocarbon group having 12 to 22 carbon atoms examples include lauryl group, stearyl group and behenyl group, preferably stearyl group or behenyl group, more preferably behenyl group.
• the unsaturated hydrocarbon group having 18 carbon atoms is preferably an oleyl group.
• R 3 represents CH 3 or (CH 2 CH 2 O)nH.
• n is an integer from 1 to 30;
• n is preferably an integer of 1 to 5, more preferably an integer of 1 to 3, and n is 1 from the viewpoint of emulsion stability and long-term durability of moisture retention after drying.
• R 3 is CH 2 CH 2 OH.
• the PC compound used in the present invention is an alcohol represented by formula (2) and 2-chloro-2-oxo-1,3,2-dioxaphospholane (hereinafter abbreviated as COP) in the presence of an organic base. It is obtained by ring-opening the intermediate obtained by the reaction with a tertiary amine represented by the formula (3).
• the resulting PC compound can be purified by general purification methods such as reprecipitation and recrystallization.
• R 1 , R 2 and R 3 in formulas (2) and (3) have the same definitions as in formula (1).
• the form of the cosmetic containing the cosmetic base of the present invention is not particularly limited. , hair mists, hair creams, hair foams and other hair cosmetics, skin care cosmetics such as lotions, milky lotions, creams, beauty essences and foundations, makeup cosmetics, massage cosmetics, and pack cosmetics. It may be in various forms such as body care cosmetics such as agents, body shampoos, and hand soaps.
• the cosmetic of the present invention contains a cosmetic material and the above PC compound.
• the blending ratio of the PC compound is not particularly limited, but is usually blended in an amount of 0.001 to 20% by mass based on the total cosmetic composition. If the amount is less than 0.001% by mass, the amount of the PC compound is insufficient, and it may be difficult to obtain the desired effect. On the other hand, if it exceeds 20% by mass, the handling properties during preparation of the cosmetic may deteriorate, and the resulting cosmetic may not exhibit a favorable feeling during use.
• the cosmetic of the present invention may contain other ingredients within a range that does not impair the performance of the present invention.
• Other components include, for example, lower alcohols, hydrocarbon oils, natural fats and oils, synthetic triglycerides, ester oils, waxes, silicone derivatives, oily bases, anionic surfactants, amphoteric surfactants, nonionic surfactants, cationic surfactants, semipolar surfactants, water-soluble polymers, organic or inorganic salts, pH adjusters, bactericides, chelating agents, antioxidants, UV absorbers, vitamins, animals and plants natural extracts, dyes, pigments, fragrances, etc. derived from
• Table 1 shows the details of the cosmetic base of the present invention synthesized in Synthesis Examples 1-6 and the 11 compounds synthesized in Comparative Synthesis Examples 1-5. Further, the compound synthesized in Comparative Synthesis Example 6 is shown in formula (4). R 1 , R 2 and R 3 in Table 1 correspond to Formula (1).
• Examples 1 to 6, Comparative Examples 1 to 7 According to the recipes in Table 2, each component of the oil phase and water phase was dissolved at 70°C. The oil phase was added to the water phase with stirring, and the mixture was stirred with a homomixer. The obtained emulsified cosmetic was evaluated for the uniformity of the oil phase at the time of production and the emulsification stability at high temperature based on the following criteria, and the following sensory test was performed. In addition, the numerical value in the table
• the compounds synthesized in Synthesis Examples 1 to 6 have excellent solubility in oily components, and emulsified cosmetics containing these compounds have high emulsification stability at high temperatures. It was found that there was no hard film feeling after application, a feeling of crushed oil droplets was felt during application, and a moist feeling was maintained for a long period of time after application. If the gemini type compound does not contain an unsaturated hydrocarbon group as in Comparative Examples 1, 2, 3, and 4, a hard film feeling is exhibited at the time of application, and the good feeling of oil droplets is not exhibited. Also, if both the hydrocarbon groups of the gemini type compound are unsaturated hydrocarbons as in Comparative Example 5, the emulsification stability is poor.
• a gemini type compound having an amide group as in Comparative Example 6 has poor solubility in an oil phase and poor emulsification stability, and develops a hard film feel after application.
• a surfactant having a phosphorylcholine group having a structure different from that of the present application, as in Comparative Example 7, is inferior in emulsion stability, and does not exhibit a pleasant feel, such as the crushing feeling of oil droplets, during application.

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• 2022
  • 2022-03-16 WO PCT/JP2022/011953 patent/WO2022209899A1/ja not_active Ceased
  • 2022-03-16 US US18/551,542 patent/US20240180808A1/en active Pending
  • 2022-03-16 CN CN202280020571.4A patent/CN117062593A/zh active Pending
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