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
  • A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
  • A61K8/86—Polyethers
• • 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
  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
  • C08G65/34—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives

Definitions

• Patent Documents 1 and 2 disclose cosmetic compositions containing specific polyethers as cosmetics that combine high moisturizing effects with a pleasant, non-sticky feel when used.
• R 1 , R 2 , and a number of R 3 are each independently a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms; the ratio of (the number of hydrogen atoms in R 1 to R 3 )/(the number of hydrocarbon groups in R 1 to R 3 ) is 20 or less;
• GL is a glycerin residue, CH2CH2O is an ethylene glycol residue ; CH 2 CH 2 CH 2 O is the 1,3-propanediol residue; C n H 2n O is an alkanediol residue having 4 to 8 carbon atoms;
• a , b , c, and d are the average degrees of polymerization of GL, CH2CH2O , CH2CH2CH2O , and CnH2nO , respectively ;
• a is a number from 0 to 30, b is a number from 0 to 80, a+b are numbers from 1 to 80, c is a number from 0
• the present invention provides a polyether that can be used as a cosmetic base, imparting moisturizing effects, a non-sticky feel, and low-temperature stability to cosmetics.
• cosmetics containing a specified amount of a cosmetic base made from the polyether of the present invention have a pleasant, non-sticky feel and high moisturizing effect, and can maintain good transparency and low-temperature stability even when the amount of surfactant used in the cosmetics is reduced.
• polyether of the present invention is represented by the following formula (1):
• the polyether of the present invention may be used alone or in combination of two or more types.
• the definitions of the symbols in formula (1) are explained below.
• R 1 , R 2 , and a number of R 3 are each independently a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms.
• Polyethers having a hydrocarbon group having 21 or more carbon atoms may result in a decrease in the moisturizing effect, transparency, or low-temperature stability of the cosmetic.
• hydrocarbon groups examples include alkyl groups, alkenyl groups, cycloalkyl groups, aryl groups, and aralkyl groups.
• the hydrocarbon group is preferably an alkyl group or an alkenyl group. Both the alkyl group and the alkenyl group may be either linear or branched.
• the ratio of (the number of hydrogen atoms in R 1 to R 3 )/(the number of hydrocarbon groups in R 1 to R 3 ) (hereinafter sometimes referred to as "hydrogen atoms/hydrocarbon groups") is 20 or less, preferably 15 or less, and more preferably 10 or less, from the viewpoints of suppressing stickiness, transparency, and low-temperature stability in the cosmetic.
• the ratio of hydrogen atoms/hydrocarbon groups may be 0. Furthermore, in this specification, when the number of hydrocarbon groups in R 1 to R 3 is 0, the ratio of hydrogen atoms/hydrocarbon groups is interpreted as ⁇ (infinity).
• the ratio of hydrogen atoms/hydrocarbon groups of the polyether (i.e., (the number of hydrogen atoms in R 1 to R 3 )/(the number of hydrocarbon groups in R 1 to R 3 )) can be calculated from the integral value of the signal of the carbonyl carbon derived from the acetyl group and the integral value of the signal of the terminal CH 3 derived from the hydrocarbon group, which are obtained by 13 C-NMR measurement when the polyether is acetylated, according to the following formula: It can be calculated by dividing the integral value of the signal of the carbonyl carbon derived from the acetyl group by the integral value of the signal of the terminal CH3 derived from the hydrocarbon group.
• the acetylation method is not particularly limited and any known method can be used, but a method using pyridine and acetic anhydride as described in the Examples section below is preferred. 13C -NMR measurement can be performed as described in the Examples section below.
• hydrogen atoms/hydrocarbon groups can be calculated by combining not only 13 C-NMR measurement but also measurements such as 1 H-NMR, DEPT135, and two-dimensional NMR (HHCOSY, HMQC, HMBC, NOESY).
• GL is a glycerin residue.
• glycocerin residue refers to a group represented by formula (2) or formula (3):
• the glycerin residue may be a group formed from a compound other than glycerin, as long as it is a group having a structure represented by formula (2) or formula (3).
• a group represented by formula (2) and “a group represented by formula (3)” may be abbreviated as “group (2)” and “group (3)”, respectively.
• both group (2) and group (3) may be present.
• both group (2) and group (3) are preferably present.
• the molar ratio of group (2)/group (3) is preferably 40/60 to 99/1, more preferably 40/60 to 90/10, and even more preferably 50/50 to 80/20, from the viewpoints of suppressing stickiness, transparency, and low-temperature stability in cosmetics.
• the molar ratio of group (2)/group (3) can be calculated by 13C -NMR measurement. Specifically, the molar ratio of group (2)/group (3) can be calculated by comparing the integral value of the signal of the methine carbon of group (2) (near 71 ppm) with the integral value of the signal of the methine carbon of group (3) (near 79 ppm).
• C n H 2n O is an alkanediol residue having 4 to 8 carbon atoms.
• the alkanediol may be either linear or branched.
• alkanediol residues having 4 to 8 carbon atoms examples include 1,2-butanediol residue, 1,3-butanediol residue, 1,4-butanediol residue, 1,2-pentanediol residue, 1,3-pentanediol residue, 1,4-pentanediol residue, 1,5-pentanediol residue, neopentyl glycol residue, 1,2-hexanediol residue, 1,3-hexanediol residue, 1,4-hexanediol residue, 1,5-hexanediol residue, 1,6-hexanediol residue, 3-methyl-1,5-pentanediol residue, 1,2-heptanediol residue, 1,7-heptanediol residue, and 1,8-octanediol residue.
• CnH2nO is preferred in view of the moisturizing effect, transparency, and low-temperature stability in cosmetics.
• it is an alkanediol residue having 4 to 6 carbon atoms, More preferably, it is a 1,2-butanediol residue, a 1,3-butanediol residue, a 1,4-butanediol residue, a 1,5-pentanediol residue, or a 1,6-hexanediol residue; More preferably, it is a 1,3-butanediol residue, a 1,4-butanediol residue, or a 1,6-hexanediol residue. Particularly preferred is a 1,3-butanediol residue or a 1,6-hexanediol residue.
• a, b, c, and d are the average degrees of polymerization of GL, CH 2 CH 2 O, CH 2 CH 2 CH 2 O, and C n H 2n O, respectively. Therefore, these may all be decimal numbers.
• b is a number from 0 to 80, preferably a number from 0 to 50, and more preferably a number from 0 to 30.
• "b is 0" means that CH 2 CH 2 O is not present.
• b is preferably a number from 4 to 50.
• c is a number from 0 to 60, preferably a number from 0 to 40, and more preferably a number from 0 to 30.
• "c is 0" means that CH 2 CH 2 CH 2 O is not present.
• d is 0, from the viewpoints of the transparency and low-temperature stability of the cosmetic, c is preferably a number from 2 to 30.
• d is a number from 0 to 60, preferably a number from 0 to 40, and more preferably a number from 0 to 30.
• d is 0
• CnH2nO is absent.
• d is preferably a number from 2 to 30.
• c + d is a number from 1 to 70, preferably a number from 2 to 50, and more preferably a number from 3 to 40.
• (a + b)/(c + d) is a number between 0.2 and 8, preferably between 0.25 and 5, and more preferably between 0.33 and 4, from the viewpoints of moisturizing effect, stickiness suppression, transparency, and low-temperature stability in cosmetics. Note that, in this specification, when c + d is 0, (a + b)/(c + d) is interpreted as ⁇ (infinity).
• n is the number of carbon atoms in C n H 2n O and is a number from 4 to 8. From the viewpoint of transparency and low-temperature stability in cosmetics, n is preferably a number from 4 to 6, more preferably 4 or 6.
• a plurality of CH 2 CH 2 O may form a block, and this block may be randomly bonded to GL, CH 2 CH 2 CH 2 O, and C n H 2n O.
• this block may be randomly bonded to GL, CH 2 CH 2 CH 2 O, and C n H 2n O.
• a (CH 2 CH 2 O) 3 block is formed.
• the weight-average molecular weight (Mw) of the polyether of the present invention calculated from a chromatogram obtained by gel permeation chromatography (GPC), is preferably 300 to 10,000, and more preferably 500 to 8,000, from the viewpoint of suppressing stickiness in cosmetics.
• the polyethers of the present invention can be produced by known methods. For example, (i) a reaction intermediate is produced by a dehydration condensation reaction of a polyhydric alcohol in the presence of an acid catalyst such as sulfuric acid at 80°C to 130°C under normal pressure, and (ii) the resulting reaction intermediate is then etherified with an alkyl halide or alkenyl halide in the presence of a catalyst such as potassium hydroxide at 80°C to 130°C to produce the polyethers of the present invention.
• an acid catalyst such as sulfuric acid at 80°C to 130°C under normal pressure
• a catalyst such as potassium hydroxide
• the polyether of the present invention can be used as a cosmetic base.
• the polyether of the present invention can also be used as a plasticizer, detergent, or wetting agent.
• the present invention provides a cosmetic base comprising the polyether of the present invention.
• the cosmetic base of the present invention may be used alone or in combination with two or more types.
• the present invention also provides a cosmetic containing the cosmetic base of the present invention in an amount of 0.1 to 30% by mass based on the total mass of the cosmetic.
• the cosmetic of the present invention is not particularly limited and may be any of aqueous cosmetics, water-in-oil or oil-in-water emulsion cosmetics, and oil-based cosmetics.
• cosmetics include skin care cosmetics such as lotions, serums, emulsions, creams, packs, and sunscreen creams; body cosmetics; makeup removers such as cleansing oils and cleansing waters; skin cleansers such as body soaps, hand soaps, and facial cleansing pastes; hair cosmetics such as shampoos, treatments, hair liquids, hair oils, hair tonics, and hair growth agents; and makeup cosmetics such as makeup bases, liquid foundations, and BB creams.
• the content of the cosmetic base of the present invention is 0.1 to 30% by mass, preferably 0.5 to 15% by mass, based on the total mass of the cosmetic of the present invention.
• the cosmetic of the present invention preferably contains water (more preferably purified water). Furthermore, the cosmetic of the present invention may contain other components different from the cosmetic base and water of the present invention, as needed, as long as the effects of the present invention are not impaired. There are no particular limitations on the other components, as long as they are components commonly used in cosmetics.
• the total amount of the other ingredients is preferably 0.1 to 80% by mass, and more preferably 0.5 to 40% by mass, of the entire lotion, serum, or emulsion of the present invention, from the viewpoints of moisturizing effect, freshness, and feel when used (e.g., a refreshing feeling).
• Water is the remainder of the lotion, serum, or emulsion of the present invention (i.e., the remainder of the lotion, serum, or emulsion other than the cosmetic base and other ingredients of the present invention).
• the total amount of the other ingredients is preferably 5 to 99% by mass, and more preferably 10 to 85% by mass, of the entire cream, liquid foundation, or sunscreen cream of the present invention, from the viewpoint of emollient effect and moisture evaporation inhibitory effect.
• Water is the remainder of the cream, liquid foundation, or sunscreen cream of the present invention (i.e., the remainder of the cream, liquid foundation, or sunscreen cream other than the cosmetic base and other ingredients of the present invention).
• the total amount of the other ingredients is preferably 40 to 99.5% by mass, and more preferably 60 to 99% by mass, based on the total amount of the cleansing oil of the present invention, from the standpoint of cleansing performance.
• Water constitutes the remainder of the cleansing oil of the present invention (i.e., the remainder of the cleansing oil other than the cosmetic base of the present invention and other ingredients).
• the total amount of the other ingredients is preferably 2 to 80% by mass, and more preferably 5 to 60% by mass, based on the total amount of the cleansing water of the present invention, from the viewpoint of cleansing performance.
• Water constitutes the remainder of the cleansing water of the present invention (i.e., the remainder of the cleansing water other than the cosmetic base of the present invention and other ingredients).
• the total amount of the other ingredients is preferably 15 to 95% by mass, and more preferably 30 to 85% by mass, of the entire facial cleansing paste of the present invention, from the viewpoint of cleansing performance.
• Water constitutes the remainder of the facial cleansing paste of the present invention (i.e., the remainder of the facial cleansing paste other than the cosmetic base of the present invention and other ingredients).
• GPC gel permeation chromatography
• Example polyether or Comparative Example polyether An aqueous solution or dispersion of the Example polyether or Comparative Example polyether was prepared by placing 2.0% of the Example polyether or Comparative Example polyether, 3.0% of PEG-40 hydrogenated castor oil and 3.0% of Polysorbate 80 as surfactants, 0.3% of olive oil and 0.1% of squalane as oil agents, and the remainder being purified water into a beaker and stirring until homogeneous.
• Example 6 Production of Example Cosmetics 1 to 15, Comparative Example Cosmetics 1 to 11, and Reference Example Cosmetics 1 and 2
• Example polyether or comparative example polyether, PEG-40 hydrogenated castor oil, common ingredients, and purified water were mixed and stirred in the amounts shown in Table 4 or Table 5 to produce Example Cosmetics 1 to 15, Comparative Examples Cosmetics 1 to 11, and Reference Example Cosmetics 1 and 2.
• the compositions of the common ingredients are shown in Table 6.
• BG is the cosmetic name indicated by the Japan Cosmetic Industry Association and stands for 1,3-butylene glycol.
• Example Polyethers 1 to 12 which correspond to the polyethers of the present invention, were excellent in all of the above evaluations.
• Comparative Example Polyethers 1 to 11 were insufficient in any of the above evaluations.
• Comparative Polyether 1 in which R 1 to R 3 are hydrogen atoms and the ratio of hydrogen atoms to hydrocarbon groups is ⁇ , the transparency of a dispersion containing olive oil and squalane was insufficient. Furthermore, Comparative Cosmetic 1, which contains Comparative Polyether 1, was insufficient in terms of non-stickiness, transparency, and low-temperature stability.
• Comparative Example Polyether 2 in which a + b exceeded 80, the transparency of the dispersion containing olive oil and squalane was insufficient. Furthermore, Comparative Example Cosmetic 2, which contained Comparative Example Polyether 2, was insufficient in terms of lack of stickiness, transparency, and low-temperature stability.
• Comparative Example Polyether 3 in which (a + b)/(c + d) was less than 0.2, the transparency of the dispersion containing olive oil and squalane was insufficient. Furthermore, Comparative Example Cosmetic 3, which contained Comparative Example Polyether 3, was insufficient in terms of lack of stickiness, moisturizing effect, transparency, and low-temperature stability.
• Comparative Polyether 6 in which the ratio of hydrogen atoms to hydrocarbon groups exceeded 20, d exceeded 60, and c + d exceeded 70, exhibited insufficient transparency in a dispersion containing olive oil and squalane. Furthermore, Comparative Cosmetic 6, which contained Comparative Polyether 6, exhibited insufficient non-stickiness, moisturizing effect, transparency, and low-temperature stability.
• Comparative Example Polyether 7 where both c and d were 0 and (a + b)/(c + d) was infinity, the transparency of the dispersion containing olive oil and squalane was insufficient. Furthermore, Comparative Example Cosmetic 7, which contained Comparative Example Polyether 7, was insufficient in terms of lack of stickiness, moisturizing effect, transparency, and low-temperature stability.
• Comparative Example Polyether 9 in which n exceeds 8, the transparency of the dispersion containing olive oil and squalane was insufficient. Furthermore, Comparative Example Cosmetic 9, which contained Comparative Example Polyether 9, had insufficient moisturizing effect, transparency, and low-temperature stability.

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