WO2021246862A1 - Polyol esters from biobased feedstocks for use as emollient in personal care applications - Google Patents
Polyol esters from biobased feedstocks for use as emollient in personal care applications Download PDFInfo
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- WO2021246862A1 WO2021246862A1 PCT/MY2021/050044 MY2021050044W WO2021246862A1 WO 2021246862 A1 WO2021246862 A1 WO 2021246862A1 MY 2021050044 W MY2021050044 W MY 2021050044W WO 2021246862 A1 WO2021246862 A1 WO 2021246862A1
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- WIPO (PCT)
- Prior art keywords
- formula
- ester
- personal care
- alkyl chain
- care composition
- Prior art date
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- 229920005862 polyol Polymers 0.000 title claims abstract description 184
- -1 Polyol esters Chemical class 0.000 title claims abstract description 165
- 239000003974 emollient agent Substances 0.000 title claims description 15
- 239000000203 mixture Substances 0.000 claims abstract description 121
- 125000000217 alkyl group Chemical group 0.000 claims description 104
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 claims description 60
- 150000002763 monocarboxylic acids Chemical class 0.000 claims description 47
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 38
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 36
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 claims description 31
- 150000001875 compounds Chemical class 0.000 claims description 29
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 claims description 26
- 238000000034 method Methods 0.000 claims description 25
- XDOFQFKRPWOURC-UHFFFAOYSA-N 16-methylheptadecanoic acid Chemical compound CC(C)CCCCCCCCCCCCCCC(O)=O XDOFQFKRPWOURC-UHFFFAOYSA-N 0.000 claims description 24
- 235000021355 Stearic acid Nutrition 0.000 claims description 24
- 238000006243 chemical reaction Methods 0.000 claims description 24
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical class CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims description 24
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 23
- 125000004432 carbon atom Chemical group C* 0.000 claims description 21
- 235000011187 glycerol Nutrition 0.000 claims description 19
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 18
- 235000021314 Palmitic acid Nutrition 0.000 claims description 18
- 239000002253 acid Substances 0.000 claims description 18
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 18
- IPCSVZSSVZVIGE-UHFFFAOYSA-N palmitic acid group Chemical group C(CCCCCCCCCCCCCCC)(=O)O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 claims description 18
- 150000003077 polyols Chemical class 0.000 claims description 17
- 239000011541 reaction mixture Substances 0.000 claims description 17
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 claims description 16
- 125000002947 alkylene group Chemical group 0.000 claims description 15
- MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid group Chemical group C(CCCCCC)(=O)O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 claims description 15
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid group Chemical group C(CCCCC)(=O)O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims description 15
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims description 12
- GYSCBCSGKXNZRH-UHFFFAOYSA-N 1-benzothiophene-2-carboxamide Chemical compound C1=CC=C2SC(C(=O)N)=CC2=C1 GYSCBCSGKXNZRH-UHFFFAOYSA-N 0.000 claims description 12
- WMYINDVYGQKYMI-UHFFFAOYSA-N 2-[2,2-bis(hydroxymethyl)butoxymethyl]-2-ethylpropane-1,3-diol Chemical compound CCC(CO)(CO)COCC(CC)(CO)CO WMYINDVYGQKYMI-UHFFFAOYSA-N 0.000 claims description 12
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 claims description 12
- GHVNFZFCNZKVNT-UHFFFAOYSA-N Decanoic acid Natural products CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 claims description 12
- 235000021360 Myristic acid Nutrition 0.000 claims description 12
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 12
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 12
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 claims description 12
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims description 12
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N pentanoic acid group Chemical group C(CCCC)(=O)O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 claims description 12
- 229960004063 propylene glycol Drugs 0.000 claims description 12
- 235000013772 propylene glycol Nutrition 0.000 claims description 12
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 11
- QWGRWMMWNDWRQN-UHFFFAOYSA-N 2-methylpropane-1,3-diol Chemical compound OCC(C)CO QWGRWMMWNDWRQN-UHFFFAOYSA-N 0.000 claims description 6
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 claims description 6
- 229940105990 diglycerin Drugs 0.000 claims description 6
- GPLRAVKSCUXZTP-UHFFFAOYSA-N diglycerol Chemical compound OCC(O)COCC(O)CO GPLRAVKSCUXZTP-UHFFFAOYSA-N 0.000 claims description 6
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 claims description 6
- 239000000600 sorbitol Substances 0.000 claims description 6
- 239000008117 stearic acid Substances 0.000 claims description 6
- 150000007513 acids Chemical class 0.000 claims description 4
- RKJGFHYCZPZJPE-UHFFFAOYSA-N 2,2-bis(16-methylheptadecanoyloxymethyl)butyl 16-methylheptadecanoate Chemical group CC(C)CCCCCCCCCCCCCCC(=O)OCC(CC)(COC(=O)CCCCCCCCCCCCCCC(C)C)COC(=O)CCCCCCCCCCCCCCC(C)C RKJGFHYCZPZJPE-UHFFFAOYSA-N 0.000 claims description 3
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid ester group Chemical class C(CCCCCCCCCCC)(=O)O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 claims description 3
- 229940118594 trimethylolpropane triisostearate Drugs 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 abstract description 5
- 229960002446 octanoic acid Drugs 0.000 description 22
- 238000009472 formulation Methods 0.000 description 14
- 101100029145 Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv) PE25 gene Proteins 0.000 description 8
- 238000000354 decomposition reaction Methods 0.000 description 8
- 239000000376 reactant Substances 0.000 description 7
- 239000002085 irritant Substances 0.000 description 6
- 231100000021 irritant Toxicity 0.000 description 6
- 239000002453 shampoo Substances 0.000 description 6
- 238000003892 spreading Methods 0.000 description 6
- 239000007788 liquid Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 239000005635 Caprylic acid (CAS 124-07-2) Substances 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 230000000875 corresponding effect Effects 0.000 description 4
- 238000005886 esterification reaction Methods 0.000 description 4
- 238000002354 inductively-coupled plasma atomic emission spectroscopy Methods 0.000 description 4
- 239000006210 lotion Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 230000035899 viability Effects 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 230000032050 esterification Effects 0.000 description 3
- 230000001965 increasing effect Effects 0.000 description 3
- 235000013336 milk Nutrition 0.000 description 3
- 239000008267 milk Substances 0.000 description 3
- 210000004080 milk Anatomy 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 0 C*C(C)*CC(C=*)N=C Chemical compound C*C(C)*CC(C=*)N=C 0.000 description 2
- 231100000124 OECD 439 In Vitro Skin Irritation Toxicity 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- 206010040880 Skin irritation Diseases 0.000 description 2
- 239000004927 clay Substances 0.000 description 2
- 230000009977 dual effect Effects 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 230000003020 moisturizing effect Effects 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
- FBUKVWPVBMHYJY-UHFFFAOYSA-N nonanoic acid Chemical compound CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 230000037307 sensitive skin Effects 0.000 description 2
- 230000001953 sensory effect Effects 0.000 description 2
- 231100000475 skin irritation Toxicity 0.000 description 2
- 230000036556 skin irritation Effects 0.000 description 2
- 238000010561 standard procedure Methods 0.000 description 2
- 238000010998 test method Methods 0.000 description 2
- 231100000048 toxicity data Toxicity 0.000 description 2
- ZLCMTFCQJBGXGR-UHFFFAOYSA-N 1,2,3-trihydroxyundecan-4-one Chemical compound CCCCCCCC(=O)C(O)C(O)CO ZLCMTFCQJBGXGR-UHFFFAOYSA-N 0.000 description 1
- 241001550224 Apha Species 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 206010015946 Eye irritation Diseases 0.000 description 1
- 235000019482 Palm oil Nutrition 0.000 description 1
- 239000005643 Pelargonic acid Substances 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 239000003463 adsorbent Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 230000003750 conditioning effect Effects 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 230000002596 correlated effect Effects 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 231100000013 eye irritation Toxicity 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000012487 in-house method Methods 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 230000035764 nutrition Effects 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000002540 palm oil Substances 0.000 description 1
- 230000002085 persistent effect Effects 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000002076 thermal analysis method Methods 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- 230000002110 toxicologic effect Effects 0.000 description 1
- 231100000723 toxicological property Toxicity 0.000 description 1
- 231100000027 toxicology Toxicity 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
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
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/37—Esters of carboxylic acids
- A61K8/375—Esters of carboxylic acids the alcohol moiety containing more than one hydroxy group
-
- 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
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/37—Esters of carboxylic acids
-
- 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
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
- A61Q19/10—Washing or bathing preparations
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/02—Preparations for cleaning the hair
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/06—Preparations for styling the hair, e.g. by temporary shaping or colouring
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/12—Preparations containing hair conditioners
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/02—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen
- C07C69/22—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen having three or more carbon atoms in the acid moiety
- C07C69/30—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen having three or more carbon atoms in the acid moiety esterified with trihydroxylic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/34—Esters of acyclic saturated polycarboxylic acids having an esterified carboxyl group bound to an acyclic carbon atom
-
- 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 personal care compositions comprising ester polyol esters, to ester polyol ester compounds, to uses of ester polyol esters in personal care compositions, and to methods of manufacturing ester polyol esters.
- a common problem associated with personal care compositions such as emollients is an undesirable residue persisting on a person’s skin after application of an emollient, particularly an oily or greasy residue. Such residues can cause skin irritation and are unpleasant to a user.
- Ester polyol esters are products formed from the reaction of a polyol with more than one equivalents of an ester such that more than one hydroxyl moiety in the polyol is esterified, as described in US 9,885,006 B2. Ester polyol esters are commonly used as lubricants and have not previously been described as useful emollients.
- ester polyol esters can have the necessary properties to be effective emollients.
- ester polyol esters can coat a person’s skin with a thin oil film that keeps skin hydrated but which does not leave an oily residue.
- Ester polyol esters are also non-irritant, stable and can be produced from renewable feedstocks.
- the present invention provides the following.
- a personal care composition comprising an ester polyol ester of formula la, and an ester polyol ester of formula lb la wherein in formula la: each Ri a is independently a linear or branched alkyl chain having from 1 to 17 carbon atoms; each R 2a is independently a linear or branched alkyl chain having from 2 to 12 carbon atoms substituted by one or more Ri a C(0)0- groups; wherein in formula lb:
- L is a linear alkylene chain with from 1 to 18 carbon atoms; each R 2b is independently a linear or branched alkyl chain having from 2 to 12 carbon atoms substituted by one or more Ri a C(0)0- groups; and each Ri a and R ia are independently a linear or branched alkyl chain having from 1 to 17 carbon atoms.
- ester polyol ester of formula la is an ester polyol ester of formula lc: lc, wherein each Ri c is independently the alkyl chain of a monocarboxylic acid selected from the group consisting of: acetic, propanoic, butyric, pentanoic, hexanoic, nonanoic, 2-ethyl hexanoic, heptanoic, octanoic, decanoic, lauric, myristic, palmitic and stearic acids, and each R 2C is independently a moiety formed by removing a primary hydroxyl group from a primary polyol selected from the group consisting of: glycerin, diglycerin, ethylene glycol, diethylene glycol, 1,2-propanediol, bis(1 ,2-propanediol), 2-methyl-1 ,3- propanediol (2-MePG),
- each R ic is independently the alkyl chain of a monocarboxylic acid selected from the group consisting of: hexanoic, nonanoic, 2-ethyl hexanoic, heptanoic, octanoic, decanoic, and lauric acids, optionally wherein each R ic is independently the alkyl chain of a monocarboxylic acid selected from the group consisting of octanoic acid and decanoic acid.
- ester polyol ester of formula lb is an ester polyol ester of formula Id: wherein:
- L is a linear alkylene chain with from 2 to 14 carbon atoms; each R 2d is independently a moiety formed by removing a primary hydroxyl group from a primary polyol selected from the group consisting of: glycerin, diglycerin, ethylene glycol, diethylene glycol, 1,2-propanediol, bis(1 ,2-propanediol), 2-methyl-1 ,3- propanediol (2-MePG), trimethylolpropane (TMP), di-trimethylolpropane (Di-TMP), neopentyl glycol (NPG), pentaerythritol (PE), dipentaerythritol (diPE) and sorbitol, wherein said moiety is bonded to the rest of the molecule at the location of the removed primary hydroxyl group, and each remaining hydroxyl functional group in said moiety is esterified with a monocarboxylic acid of formula Ri c -COOH; each
- R 2C and/or R 2 i are a moiety having the formula: where the dashed line represents the point of attachment to the rest of the molecule, and wherein each R ic independently represents the alkyl chain of a monocarboxylic acid selected from the group consisting of: acetic, propanoic, butyric, pentanoic, hexanoic, nonanoic, 2-ethyl hexanoic, heptanoic, octanoic, decanoic, lauric, myristic, palmitic and stearic acids, optionally wherein each Ri c is independently the alkyl chain of a monocarboxylic acid selected from the group consisting of octanoic acid and decanoic acid.
- R 2C and/or R 2d are a moiety having the formula: where the dashed line represents the point of attachment to the rest of the molecule, and wherein each R ic independently represents the alkyl chain of a monocarboxylic acid selected from the group consisting of: acetic, propanoic, butyric, pentanoic, hexanoic, nonanoic, 2-ethyl hexanoic, heptanoic, octanoic, decanoic, lauric, myristic, palmitic and stearic acids, optionally wherein each Ri c is independently the alkyl chain of a monocarboxylic acid selected from the group consisting of octanoic acid and decanoic acid.
- each R ic independently represents the alkyl chain of a monocarboxylic acid selected from the group consisting of: acetic, propanoic, butyric, pentanoic, hexanoic, nonanoi
- each A independently represents a linear C5-9 alkyl chain, or a linear or branched C14-17 alkyl chain
- lib wherein in formula lib: each A independently represents a linear C5-9 alkyl chain, or a linear or branched C14-17 alkyl chain
- n is an integer of from 6 to 10.
- each A independently represents a C 6-8 alkyl group, optionally a C7 alkyl group;
- each A independently represents the alkyl chain of a monocarboxylic acid selected from the group consisting of palmitic and stearic acids, optionally the alkyl chain of isostearic or stearic acid, more optionally the alkyl chain of isostearic acid.
- ester polyol ester of formula la is an ester polyol ester of formula lie
- ester polyol ester of formula lb is an ester polyol ester of formula lid: lie wherein in formula lie each A independently represents a linear C5-9 alkyl chain, or a linear or branched C14-17 alkyl chain
- lid wherein in formula lid: each A independently represents a linear C5-9 alkyl chain, or a linear or branched C14-17 alkyl chain
- n is an integer of from 6 to 10.
- each A independently represents a C 6-8 alkyl group, optionally a C 7 alkyl group;
- each A independently represents the alkyl chain of a monocarboxylic acid selected from the group consisting of palmitic and stearic acids, optionally the alkyl chain of isostearic or stearic acid, more optionally the alkyl chain of isostearic acid. 16.
- n is an integer of from 7 to 9, optionally wherein n is 8.
- each A represents a C 7 alkyl group and n is 8;
- ester polyol ester of formula la, lc or I la to ester polyol ester of formula lb, Id or lib is from 60:40 to 70:30;
- ester polyol ester of formula la, lc or lla is from 40:60 to 50:50.
- the personal care composition according to Clause 20 wherein the reaction is quenched once the acid value reaches a value below 20 mgKOH/g, and the hydroxyl value reaches a value below 5 mgKOH/g. 22.
- the personal care composition according to Clause 20 or 21 wherein the mixture of ester polyol esters of formula la, lb, lc, Id, I la, lib, lie or lid produced by said reaction has a dynamic viscosity at 25°C of from 20 to 90 cps, preferably a dynamic viscosity at25°C selected from: (a) 20-30 cps;
- the personal care composition according to any one of the preceding clauses, wherein the total combined mass percent of ester polyol ester or formula la, lc, lla or lie and ester polyol ester of formula lb, Id, lib or lid in the personal care composition is from 0.5 to 65 wt. %, preferably from 0.5 to 15 wt. %, such as 0.5 to 12 wt. %.
- ester polyol ester as described in any one of Clauses 1 to 25 in a personal care composition, optionally wherein the ester polyol ester comprises a first ester polyol ester or formula la, lc, lla or lie and second ester polyol ester of formula lb, Id, lib or lid.
- each A independently represents a C 6-8 alkyl group.
- a method for preparing an ester polyol ester comprising preparing a reaction mixture comprising: a polyol selected from the group consisting of glycerin, trimethylolpropane and a combination thereof; sebacic acid; and octanoic acid, wherein the method comprises a step of esterifying the glycerin with sebacic acid and octanoic acid, wherein the reaction mixture has a hydroxyl group to carboxyl group ratio (HCR) corresponding to a ratio of moles of hydroxyl groups to moles of carboxyl groups, and the HCR is less than about 1 , and wherein the molar ratio of octanoic acid to sebacic acid is from 99.99:0.01 to 99:1 (such as about 99.97:0.03 to about 99.7:0.3, for example about 99.95:0.05, about 99.875:0.125, or about 99.78:0.22).
- HCR hydroxyl group to carboxyl group ratio
- reaction mixture has a hydroxyl to carboxyl ratio (HCR) of less than about 0.97, preferably from about 0.92 to about 1 , more preferably from about 0.92 to about 0.97, further preferably from about 0.93 to about 0.95, more preferably still from about 0.940 to about 0.955.
- HCR hydroxyl to carboxyl ratio
- FIG. 1 shows the structure of an ester polyol ester formed from glycerin and caprylic acid.
- FIG. 2 shows the structure of an ester polyol ester formed from glycerin, sebacic acid and caprylic acid.
- FIG. 3 shows toxicity data for compounds according to the invention as tested with OECD 492.
- FIG. 4 shows toxicity data for compounds according to the invention as tested with OECD 439.
- the invention provides a personal care composition
- a personal care composition comprising an ester polyol ester of formula la, and an ester polyol ester of formula lb la wherein in formula la: each Ri a is independently a linear or branched alkyl chain having from 1 to 17 carbon atoms; each R 2a is independently a linear or branched alkyl chain having from 2 to 12 carbon atoms substituted by one or more Ri a C(0)0- groups; lb wherein in formula lb:
- L is a linear alkylene chain with from 1 to 18 carbon atoms; each R 2b is independently a linear or branched alkyl chain having from 2 to 12 carbon atoms substituted by one or more R ia C(0)0- groups; and each Ri a and Ri a are independently a linear or branched alkyl chain having from 1 to 17 carbon atoms.
- the term “comprising” may be interpreted as requiring the features mentioned, but not limiting the presence of other features.
- the word “comprising” may also relate to the situation where only the components/features listed are intended to be present (e.g. the word “comprising” may be replaced by the phrases “consists of or “consists essentially of). It is explicitly contemplated that both the broader and narrower interpretations can be applied to all aspects and embodiments of the present invention.
- the word “comprising” and synonyms thereof may be replaced by the phrase “consisting of or the phrase “consists essentially of or synonyms thereof and vice versa.
- ester polyol ester means a compound formed from the esterification of at least two hydroxyl groups in a polyol.
- the ester polyol esters have at least 90% esterification of polyol hydroxyl groups, such as at least 95%, at least 99%, at least 99.5% such as about 100% esterification of polyol hydroxyl groups.
- polyol ester may be used interchangeably herein with “ester polyol ester” .
- alkyl means a monovalent group of formula -C n H 2 n +i .
- Alkyl groups may be linear or branched. In some embodiments of the invention, alkyl groups may be linear. In other embodiments of the invention, alkyl groups may be branched.
- alkylene means a divalent group of formula -C n H 2n -.
- Alkylene groups may be linear or branched. In some embodiments of the invention, alkylene groups are typically linear.
- formulation and “composition” may be used interchangeably herein.
- the ester polyol ester of formula la may be an ester polyol ester of formula lc: lc, wherein each Ri c is independently the alkyl chain of a monocarboxylic acid selected from the group consisting of: acetic, propanoic, butyric, pentanoic, hexanoic, nonanoic, 2-ethyl hexanoic, heptanoic, octanoic, decanoic, lauric, myristic, palmitic and stearic acids, and each R 2C is independently a moiety formed by removing a primary hydroxyl group from a primary polyol selected from the group consisting of: glycerin, diglycerin, ethylene glycol, diethylene glycol, 1,2-propanediol, bis(1 ,2-propanediol), 2-methyl-1 ,3-propanediol (2-MePG), trimethylo
- each Ri c may independently be the alkyl chain of a monocarboxylic acid selected from the group consisting of: hexanoic, nonanoic, 2-ethyl hexanoic, heptanoic, octanoic, decanoic, and lauric acids.
- each R ic may independently be the alkyl chain of a monocarboxylic acid selected from the group consisting of octanoic acid and decanoic acid.
- R ic may be the alkyl chain of octanoic acid.
- ester polyol ester of formula lb may be an ester polyol ester of formula Id:
- each R 2d is independently a moiety formed by removing a primary hydroxyl group from a primary polyol selected from the group consisting of: glycerin, diglycerin, ethylene glycol, diethylene glycol, 1 ,2-propanediol, bis(1 ,2-propanediol), 2-methyl-1 ,3-propanediol (2-MePG), trimethylolpropane (TMP), di-trimethylolpropane (Di-TMP), neopentyl glycol (NPG), pentaerythritol (PE), dipentaerythritol (diPE) and sorbitol, wherein said moiety is bonded to the rest of the molecule at the location of the removed primary hydroxyl group, and each remaining hydroxyl functional group in said moiety is esterified with a monocarboxylic acid of formula Ri
- L may be a linear alkylene chain with from 4 to 12 carbon atoms, for example a C 8 linear alkylene chain.
- R 2c and/or R 2 i may be a moiety having the formula: where the dashed line represents the point of attachment to the rest of the molecule, and wherein each R ic independently represents the alkyl chain of a monocarboxylic acid selected from the group consisting of: acetic, propanoic, butyric, pentanoic, hexanoic, nonanoic, 2-ethyl hexanoic, heptanoic, octanoic, decanoic, lauric, myristic, palmitic and stearic acids.
- a monocarboxylic acid selected from the group consisting of: acetic, propanoic, butyric, pentanoic, hexanoic, nonanoic, 2-ethyl hexanoic, heptanoic, octanoic, decanoic, lauric, myristic, palmitic and stearic acids.
- each Ri c may independently be the alkyl chain of a monocarboxylic acid selected from the group consisting of octanoic acid and decanoic acid.
- R 2c and/or R 2 i may be a moiety having the formula: where the dashed line represents the point of attachment to the rest of the molecule, and wherein each R ic independently represents the alkyl chain of a monocarboxylic acid selected from the group consisting of: acetic, propanoic, butyric, pentanoic, hexanoic, nonanoic, 2-ethyl hexanoic, heptanoic, octanoic, decanoic, lauric, myristic, palmitic and stearic acids.
- each Ri c may independently be the alkyl chain of a monocarboxylic acid selected from the group consisting of oct
- the ester polyol ester of formula la may be an ester polyol ester of formula lla, and/or the ester polyol ester of formula lb is an ester polyol ester of formula lib: lla wherein in formula lla each A independently represents a linear C5-9 alkyl chain, or a linear or branched C14-17 alkyl chain; lib wherein in formula lib: each A independently represents a linear C5-9 alkyl chain, or a linear or branched C14-17 alkyl chain; and n is an integer of from 6 to 10.
- each A may independently represent a linear C5-9 alkyl chain, for example a linear C 6-8 alkyl group, such as a linear C7 alkyl group.
- n is an integer of from 7 to 9, such as 8.
- each A represents a C 7 alkyl group and n is 8.
- a particular example of a compound of formula lib that may be mentioned herein is capryloyl glycerin/sebacic acid copolymer.
- each A may independently represent a linear or branched C14-17 alkyl chain, optionally the alkyl chain of a monocarboxylic acid selected from the group consisting of palmitic and stearic acids, more optionally the alkyl chain of isostearic or stearic acid, further optionally the alkyl chain of isostearic acid.
- n is an integer of from 6 to 10, optionally an integer of from 7 to 9, such as 8.
- the ester polyol ester of formula la may be an ester polyol ester of formula lie
- the ester polyol ester of formula lb may be an ester polyol ester of formula lid: wherein in formula lie each A independently represents a linear C5-9 alkyl chain, or a linear or branched C14-17 alkyl chain
- lid wherein in formula lid: each A independently represents a linear C5-9 alkyl chain, or a linear or branched C14-17 alkyl chain
- n is an integer of from 6 to 10.
- each A may independently represent a linear C5-9 alkyl chain, for example a linear C 6-8 alkyl group, such as a linear C 7 alkyl group.
- n is an integer of from 7 to 9, such as 8.
- each A represents a C 7 alkyl group and n is 8.
- each A may independently represent a linear or branched Ci 4 -i 7 alkyl chain, optionally the alkyl chain of a monocarboxylic acid selected from the group consisting of palmitic and stearic acids, more optionally the alkyl chain of isostearic or stearic acid, further optionally the alkyl chain of isostearic acid.
- n is an integer of from 6 to 10, optionally an integer of from 7 to 9, such as 8.
- a particular example of a compound of formula lie that may be mentioned herein is trimethylolpropane triisostearate.
- the weight ratio of the ester polyol ester of formula la, lc, I la or lie to ester polyol ester of formula lb, Id, lib or lid may be from 95:5 to 30:70.
- the particular weight ratio will influence the properties of the mixture of ester polyol esters, such as the viscosity and surface tension.
- the ratio of ester polyol esters may be varied to provide the desired physical properties for the personal care composition, which will depend on the type of personal care composition. For example, as will be appreciated by a person skilled in the art, the required physical properties for a hair wax are different to those for a moisturising cream.
- ester polyol esters that may be useful in the present invention are set out below.
- the weight ratio of ester polyol ester of formula la, lc or I la to ester polyol ester of formula lb, Id or lib is from 90:10 to 80:20.
- ester polyol ester of formula la, lc or lla The weight ratio of ester polyol ester of formula lb, Id or lib is from 40:60 to 50:50.
- the ratio of ester polyol esters in a personal care composition will correspond to the ratio in which they are produced during the production method.
- the ratio of ester polyol ester of formula la, lc, lla or lie to ester polyol ester of formula lb, Id, Mb or lid produced by the reaction will depend on the ratio of monocarboxylic acid (e.g. octanoic acid) to dicarboxylic acid (e.g. sebacic acid) in the reaction mixture.
- monocarboxylic acid e.g. octanoic acid
- dicarboxylic acid e.g. sebacic acid
- the concentration of dicarboxylic acid is typically kept low.
- the molar ratio of monocarboxylic acid to dicarboxylic acid in the reaction mixture is typically from 99.99:0.01 to 99:1 (such as about 99.97:0.03 to about 99.7:0.3). Specific molar ratios that may be mentioned herein include about 99.95:0.05, about 99.875:0.125, and about 99.78:0.22.
- the ester polyol esters of formula la, lb, lc, Id, lla, Mb, lie or lid are present in the personal care composition in the ratio produced by a reaction between: a polyol of formula R 2a -OH or R 2b -OH; a monocarboxylic acid of formula Ri a -COOH; and a dicarboxylic acid of formula HOOC-L-COOH, wherein the molar ratio of monocarboxylic acid to dicarboxylic acid in the reaction mixture is from 99.99:0.01 to 99:1 (such as about 99.97:0.03 to about 99.7:0.3, for example about 99.95:0.05, about 99.875:0.125, or about 99.78:0.22), and the ratio of hydroxyl groups to carboxyl groups in the reaction mixture is from about 0.940 to about 0.955.
- the reaction to produce the ester polyol esters is quenched when the acid value reaches a value below 20 mgKOH/g, and the hydroxyl value reaches a value below 5 mgKOH/g.
- This has the effect of stopping the reaction when the amount of free acid and hydroxyl groups is low, and the reaction has almost run to completion. This may help to reduce the formation of unwanted side products.
- the mixture of ester polyol esters produced by the reaction will have a dynamic viscosity. This is a key property that influences how the personal care composition will feel on a person’s skin, and can be adjusted by varying the carbon chain lengths and ratio of mono-acid to diacid in the reaction mixture.
- ester polyol esters of formula la, lb, lc, Id, I la, lib, lie or lid produced by said reaction has a dynamic viscosity at 25°C of from 20 to 90 cps.
- Particular dynamic viscosities at 25°C that may be mentioned herein include 20-30 cps; 35-45 cps; and 80-90 cps.
- the amount of ester polyol ester in a personal care composition will depend on the intended use of the personal care composition.
- “amount of ester polyol ester” refers to the total amount of ester polyol ester of formula la, lb, lc, Id, lla, lib, lie and lid in the composition.
- the amount of ester polyol ester in the personal care composition may be from 0.5 to 65 wt. %.
- the amount of ester polyol ester in the personal care composition may be from about 0.5 to about 15 wt. %, such as 0.5 to 12 wt. %. Particular personal care compositions according to the invention are discussed in the below Examples.
- ester polyol esters may be produced from a variety of feedstocks. For example, they may be produced from renewable biobased feedstocks. They may also be produced from synthetic or non-biobased feedstocks. In some embodiments of the invention, particularly when longer chain acids are desired, the ester polyol esters may be formed from a biobased feedstock comprising palm acids, which may be derived from palm oil.
- the personal care composition of the invention may be any personal care composition in which the ester polyol esters may be useful.
- the personal care composition may be a haircare composition or a skincare composition, especially an emollient composition.
- haircare compositions include a hair mask, a hair wax, a shampoo, and a hair conditioner.
- a skincare composition include a body wash, a skin or body lotion, and a body milk.
- Any of the personal care compositions of the invention may be optimised for healthy adult skin, baby skin, or other sensitive skin.
- a body wash, skin or body lotion, shampoo and body milk may be desirably optimised for baby skin or other sensitive skin such as on a user’s face.
- compositions may be suitable for more than one use, and may function as both a haircare and skincare composition, or have dual functionality within the class of haircare or skincare compositions.
- dual functionality personal care compositions include a combined hair and body wash, and a combined “two in one” shampoo and conditioner composition.
- the ester polyol esters used in the personal care compositions may have a dynamic viscosity at 25°C selected from any one of the below ranges: from 20 to 90 cps, from 20 to 80 cps, from 20 to 45 cps, from 20 to 35 cps, from 20 to 30 cps; from 30 to 90 cps, from 30 to 80 cps, from 30 to 45 cps, from 30 to 35 cps; from 35 to 90 cps, from 35 to 80 cps, from 35 to 45 cps; from 45 to 90 cps, from 45 to 80 cps; from 80 to 90 cps.
- the invention also provides the use of an ester polyol ester as disclosed herein, in a personal care composition.
- the use may comprise the use of a first ester polyol ester or formula la, lc, I la or lie and second ester polyol ester of formula lb, Id, lib or lid.
- the invention also provides certain compounds of formula I la, lib, lie and lid.
- the invention provides a compound of formula lla or lie: lie wherein each A independently represents a C 6-8 alkyl group.
- the compound of formula lla may have the formula
- the compound of formula lie may have the formula
- the invention provides a compound of formula lib or lid: wherein each A independently represents a C 6-8 alkyl group and n is an integer of from 6 to 10.
- the compound of formula lib has the structure
- the compound of formula lid has the structure
- the invention also provides a method for preparing an ester polyol ester (such as an ester polyol ester of formula I la-1 Id above), the method comprising preparing a reaction mixture comprising: a polyol selected from the group consisting of glycerin, trimetholoyl propane and a combination thereof; sebacic acid; and octanoic acid, wherein the method comprises a step of esterifying the glycerin with sebacic acid and octanoic acid, wherein the reaction mixture has a hydroxyl group to carboxyl group ratio (HCR) corresponding to a ratio of moles of hydroxyl groups to moles of carboxyl groups, and the HCR is less than about 1 , and wherein the molar ratio of octanoic acid to sebacic acid is from 99.99:0.01 to 99:1.
- HCR hydroxyl group to carboxyl group ratio
- the molar ratio of octanoic acid to sebacic acid may be about 99.97:0.03 to about 99.7:0.3, for example about 99.95:0.05, about 99.875:0.125, or about 99.78:0.22).
- the reaction may be quenched once the acid value reaches a value below 20 mgKOH/g, and the hydroxyl value reaches a value below 5 mgKOH/g.
- the mixture of ester polyol esters produced by the reaction may have a dynamic viscosity at 25°C of from 20 to 90 cps.
- the mixture of ester polyol esters produced by the reaction may have a dynamic viscosity at 25°C of from 20-30 cps, 35-45 cps, or 80-90 cps.
- ester polyol esters useful in the personal care compositions of the invention may be made by corresponding methods to that described above.
- Other methods for preparing ester polyol esters are described in US 9,885,006 B2 and the below Examples.
- the ester polyol esters used in the present invention can provide personal care compositions having enhanced sensory characteristics.
- the ester polyol esters are more fluid than many known emollients, and this provides a lighter and less oily fee on the skin, as well as resulting in lower irritation potential.
- the ester polyol esters are also highly stable, enhancing the oxidation stability of the personal care compositions and making them suitable for prolonged storage without requiring antioxidants to be added to the composition.
- Ester polyol esters formed from polyols such as glycerin and TMP are highly branched, allowing the manufacture of higher molecular weight products that have lower viscosity than unbranched ester polyol esters. This improves the spreadability of the resulting compositions, providing the properties discussed above.
- the ester polyol esters may also have a higher refractive index, resulting in a higher shine, which is especially desirable in haircare products.
- Sebacic acid was purchased from Megachem, with purity 99.5%.
- Caprylic acid was purchased from KLK Oleochemicals with purity 99%.
- Glycerin was purchased from KLK Oleochemicals with purity 99.7%.
- a polyol, a monoacid, a diacid, and a tin oxide catalyst (amounts specified in Tables 1 a and 1 b below) were mixed in a reactor protected from oxygen and moisture.
- the reaction setup comprised a 4-neck round bottom flask equipped with overhead stirrer, inlet for nitrogen gas for blanketing, condenser with dean stark apparatus attached to it and a thermocouple/temperature controller.
- the resulting mixture was initially homogenized at 115°C, after which the content was sampled to determine the acid value.
- the reactor temperature was increased stepwise to 115°C, 180°C and finally to the maximum reaction temperature of 210°C.
- the reaction produced water, which was removed by the elevated temperature and condensed by a condenser.
- PE25, PE50 and PE100 comprise the two compounds shown in Fig. 1 and Fig. 2.
- EM25 and EM44 comprise analogous compounds formed from the C 9 mono- and di-acids azelaic acid and pelargonic acid.
- the amount of each reagent used to prepare the glycerin ester polyol esters is shown in Table 1a. Table 1a: Details of reactants for preparing glycerin polyol esters
- the elastic-like force between the as-synthesized polyol esters and air also referred to as surface tension
- TGA thermogravimetric analyser
- the spreading ability of the polyol ester samples was measured by the following method. At 25°C, a drop of the sample (20 pi) was applied to a flat, horizontal surface of ash-less paper (a Whatman filter paper). The liquid emollient sample was left to spread for 10 minutes. After 10 minutes, the wetted area was measured and the results are tabulated in Table 7. PE25 recorded the highest spreading area over a 10 minute duration, followed by PE50 and PE100. PE25 exhibited a fast spreading ability compared to PE50 and PE100 with medium and low spreading ability, respectively. Visually, PE25 appeared to be less viscous than PE50 and PE100.
- ICP-OES Inductively coupled plasma-optical emission spectrometry
- OECD 492 a mean tissue viability of greater than or equal to 60% results in no classification, and indicates a non-irritant compound, while a mean tissue viability score of less than 60% results in a classification (Category 1 or Category 2), and indicates an irritant compound.
- OECD 439 a mean tissue viability of greater than or equal to 50% results in no classification, and indicates a non-irritant compound, while a mean tissue viability score of less than 50% results in a classification (Category 1 or Category 2), and indicates an irritant compound.
- both EM25 and EM44 are non-irritant compounds according to both OECD 492 and OECD TG439.
- Example 3 Examples of personal care formulations
- Table 11 Nature-Derived, Sulfate-Free Moisturizing Shampoo and Body Wash formulation
- Table 12 Air conditioner formulation
- Example 4 Comparison of various chemical properties with known emollients
- Table 18 Comparison of chemical properties with known emollients.
- ester polyol esters EM25 and EM44 have improved viscosity, spreadability and refractive index for their molecular weight. This results in improved sensory characteristics and an advantageously increased shine.
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Abstract
Description
Claims
Priority Applications (6)
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AU2021285699A AU2021285699A1 (en) | 2020-06-05 | 2021-06-04 | Polyol esters from biobased feedstocks for use as emollient in personal care applications |
KR1020227035498A KR20230067576A (en) | 2020-06-05 | 2021-06-04 | Polyol Esters from Bio-Based Sources for Use as Emollients in Personal Care Applications |
CN202180039967.9A CN115666498A (en) | 2020-06-05 | 2021-06-04 | Polyol esters from biobased feedstocks for use as emollients in personal care applications |
US18/007,586 US20230233430A1 (en) | 2020-06-05 | 2021-06-04 | Polyol esters from biobased feedstocks for use as emollient in personal care applications |
EP21818357.2A EP4120995A4 (en) | 2020-06-05 | 2021-06-04 | Polyol esters from biobased feedstocks for use as emollient in personal care applications |
JP2022574500A JP2023529357A (en) | 2020-06-05 | 2021-06-04 | Polyol esters from biobased raw materials for use as emollients in personal care applications |
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EP (1) | EP4120995A4 (en) |
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WO2023163035A1 (en) * | 2022-02-24 | 2023-08-31 | 日清オイリオグループ株式会社 | Oligoester and cosmetic containing said oligoester |
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GB915161A (en) * | 1958-02-07 | 1963-01-09 | Heyden Newport Chemical Corp | Improvements in or relating to synthetic lubricants |
US20050288478A1 (en) * | 2004-06-28 | 2005-12-29 | Inolex Investment Corp. | Complex polyol polyester polymer compositions for use in personal care products and related methods |
US20070207104A1 (en) * | 2006-03-06 | 2007-09-06 | Borish Edward T | Antimicrobial esters |
CN102010772A (en) * | 2010-12-01 | 2011-04-13 | 中国科学院新疆理化技术研究所 | Ester lubricating base oil with dumbbell-type structure and preparation method thereof |
US20160002569A1 (en) * | 2013-02-28 | 2016-01-07 | Petroliam Nasional Berhad | The preparation of biopolyol esters for lubricant application |
-
2020
- 2020-06-05 MY MYPI2020002906A patent/MY197602A/en unknown
-
2021
- 2021-06-04 WO PCT/MY2021/050044 patent/WO2021246862A1/en unknown
- 2021-06-04 CN CN202180039967.9A patent/CN115666498A/en active Pending
- 2021-06-04 US US18/007,586 patent/US20230233430A1/en active Pending
- 2021-06-04 AU AU2021285699A patent/AU2021285699A1/en active Pending
- 2021-06-04 KR KR1020227035498A patent/KR20230067576A/en active Search and Examination
- 2021-06-04 JP JP2022574500A patent/JP2023529357A/en active Pending
- 2021-06-04 EP EP21818357.2A patent/EP4120995A4/en active Pending
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GB915161A (en) * | 1958-02-07 | 1963-01-09 | Heyden Newport Chemical Corp | Improvements in or relating to synthetic lubricants |
US20050288478A1 (en) * | 2004-06-28 | 2005-12-29 | Inolex Investment Corp. | Complex polyol polyester polymer compositions for use in personal care products and related methods |
US20070207104A1 (en) * | 2006-03-06 | 2007-09-06 | Borish Edward T | Antimicrobial esters |
CN102010772A (en) * | 2010-12-01 | 2011-04-13 | 中国科学院新疆理化技术研究所 | Ester lubricating base oil with dumbbell-type structure and preparation method thereof |
US20160002569A1 (en) * | 2013-02-28 | 2016-01-07 | Petroliam Nasional Berhad | The preparation of biopolyol esters for lubricant application |
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WO2023163035A1 (en) * | 2022-02-24 | 2023-08-31 | 日清オイリオグループ株式会社 | Oligoester and cosmetic containing said oligoester |
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US20230233430A1 (en) | 2023-07-27 |
JP2023529357A (en) | 2023-07-10 |
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