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CN111821216A - Liquid thickener composition comprising polyalkoxylated polyol polyester having Guerbet acid moieties - Google Patents

Liquid thickener composition comprising polyalkoxylated polyol polyester having Guerbet acid moieties Download PDF

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CN111821216A
CN111821216A CN201910248814.XA CN201910248814A CN111821216A CN 111821216 A CN111821216 A CN 111821216A CN 201910248814 A CN201910248814 A CN 201910248814A CN 111821216 A CN111821216 A CN 111821216A
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glyceryl
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塞缪尔·Q·林
徐·秦
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Appchem Ltd
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    • 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
    • A61K8/85—Polyesters
    • 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
    • A61K47/34—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyesters, polyamino acids, polysiloxanes, polyphosphazines, copolymers of polyalkylene glycol or poloxamers
    • 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
    • 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
    • A61K2800/48—Thickener, Thickening system

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Abstract

The present application relates to liquid thickener compositions comprising polyalkoxylated polyol polyesters having Guerbet acid moieties. The compounds contained herein relate to polyalkoxylated polyol polyesters having a viscosity that allows the product to be poured but remain on the desired surface to which it is applied. Examples of such compounds may be illustrated by the following formula: q- [ (OA)n‑OR]m。

Description

Liquid thickener composition comprising polyalkoxylated polyol polyester having Guerbet acid moieties
Priority requirement
This non-provisional application is a continuation-in-part application of U.S. application No. 15/652,602 filed on 18.7.2017, which claims priority to U.S. application No. 62/499,643 filed on 1.2.2017 and U.S. application No. 62/495,443 filed on 14.9.2016, the contents of which are incorporated herein by reference in their entirety.
Technical Field
The field of the invention and its examples relate to polyalkoxylated polyol polyesters which can develop a viscosity that allows the product to be poured but remain on the desired surface to which it is applied.
Background
Rheology or material flow studies are applied to consumer products such as shower gels, shampoos, liquid detergents, dish detergents, hand washes, skin care lotions or creams, hair conditioners, hair styling products, etc. to develop a specific viscosity profile. This profile is critical to the consumer's product preferences and final purchasing decisions.
Consumers prefer products with such rheological profiles: the product is stable in the container, low enough in viscosity to be easily poured from the container, and also thick enough to be applied to the body, hair or fabric without dripping from the consumer's hands or the surface to which it is applied. In addition, the product must stabilize and maintain a consistent rheological profile during storage in the warehouse, while in transit, and while on the shelf for many years.
There are many commercial thickeners that use esters of polyalkoxylated polyols and fatty acids to thicken surfactant-containing formulations. Examples of commercial products include polyethylene glycol 6000 distearate, also known under the INCI name PEG-150 distearate; PEG 120 methyl glucose dioleate and PEG 120 methyl glucose trioleate (glucmate)TMDOE 120 and GlucomateTMVLT); PEG-150 pentaerythritol tetrastearate (Crothix)TMCrothix (TM) Liquid and VersathixTM) (ii) a PEG-150 polyglyceryl-2 tristearate (Genapol LT); PEG/PPG-120/10-trimethylolpropane trioleate (Arlypon TT). The number of hydrophilic polyalkoxylated arms was two in PEG-150 distearate, three in Arlypon TT, four in Genapol LT and Crothix, Crothix Liquid and Versathix, and five in Glucomate DOE 120.
US5,192,462 (Gloor et al) relates to thickeners comprising tetraesters made from fatty acids and polyoxyethylene pentaerythritol having four polyethylene glycol arms. Its preferred chemical structure is PEG-150 pentaerythritol tetrastearate, which is a matrix for Crothix, Crothix Liquid, and Versathix Liquid.
US7,709,011 and US7,553,495 (both Klug et al) relate to thickeners of oxyalkylated polyglycerol esters with fatty acids for topical formulations containing surfactants, as shown below.
Figure BDA0002011799810000021
Wherein A is of the formula-C2H4-or C3H6A radical of formula-B is hydrogen or a radical of formula-COR, wherein at least one symbol B is a radical of formula-COR-, R is C7-C21Alkyl radical, C7-C21Hydroxyalkyl or alkenyl, n is a number from 1 to 10, preferably from 1.8 to 5, and x, y, z are numbers from 0 to 100, wherein the sum of x, y and z is from 50 to 250, and preferably 130-170. This definition of formula-1 is described in column 2, lines 24-28.
For those skilled in the art, the number of hydrophilic poly (ethylene glycol) arms is equal to n + 2. When n is 10 and x + y + z is 250, the average number of ethylene glycol units or (x + y + z)/n is [250/(10+2) ] and is at most about 21.
Disclosure of Invention
Embodiments of the present invention may be added to containers at room temperature or higher during the manufacture of cosmetic, dermatological, and pharmaceutical compositions (e.g., shampoos, shower gels, etc.).
An object of an embodiment of the present invention is a flowable liquid comprising a high concentration of a polyalkoxylated polyol polyester of formula-2, an organic vehicle, and water.
Q-[(OA)n-OR]m
Formula-2
Wherein Q is defined as the group of an organic polyol compound having the elements carbon, hydrogen, oxygen and nitrogen, and having 6 to 50 carbon atoms, and being a saturated or unsaturated, linear, branched or cyclic chain, and being independently substituted by 6 to 25 groups of the formula [ (OA)n-OR]Substituted with a group of (1); wherein A is selected from-C2H4-or-C3H6-; n is 1 to 125; r is independently selected from hydrogen or-COR1(ii) a And R is1Independently selected from C6-C34Alkyl radical, C6-C22Hydroxyalkyl radical, C2-C34An alkenyl group; wherein R is1Preferably stearic acid moieties, isostearic acid moieties, oleic acid moieties, guerbet acid moieties having from 12 to 32 carbon atoms, or mixtures thereof. - [ (OA)n-OR]"is a group attached to the Q group. Highly preferred R1Is an oleic acid moiety; another highly preferred example is a mixture of isostearic acid and guerbet acid. In some embodimentsThe Guerbet acid has 12 to 32 carbons, more preferably about 16 to 32 carbons, more preferably 18 to 24 carbons, and most preferably 20 carbons, and COR1Is not less than 2.5, preferably not less than 3, and most preferably not less than 4, based on the polyalkoxylated polyol polyester according to formula-2 in the composition; and m is an integer selected from 6 to 25, preferably 6 to 12. N per hydrophilic poly (alkylene glycol) arm may range from 1 to 125, and the average number of n is from 25 to 120, preferably from 30 to 85, and most preferably from 30 to 70.
In one embodiment, the invention relates to the following items:
1. a liquid thickener composition comprising:
20% to 80% of a polyalkoxylated polyol polyester of formula:
Q-[(OA)n-OR]m
formula-2
Q is a radical of an organic polyol compound having 6 to 50 carbon atoms and being a saturated or unsaturated linear, branched or cyclic chain structure wherein one or more, preferably all of said carbon atoms are independently represented by the formula [ (OA)n-OR]Wherein n is 6 to 25,
wherein each of the remaining 6 to 50 carbon atoms is independently substituted with hydrogen, oxygen (preferably-OH) or nitrogen (preferably-NH)2) Particularly preferably hydrogen;
a is selected from-C2H4-or-C3H6-，
R is independently selected from hydrogen or-COR1，
Wherein COR in said composition1The average total number of the (A) is more than or equal to 2,
R1independently selected from C6-C34Alkyl, preferably derived from a guerbet acid; c6-C22Hydroxyalkyl radicals, preferably derived from guerbet acids; c6-C22Alkenyl, preferably derived from a guerbet acid;
wherein R is1Preferably derived from stearic acid, isostearic acid, oleic acid, Guerbet acid or mixtures thereof,
n is an integer independently selected from 1 to 125, and
m is an integer selected from 6 to 25;
an organic vehicle selected from the group consisting of: an organic solvent, a hydrophobic thickener, or a mixture thereof,
the organic solvent is selected from the group consisting of: mono-or polyhydric alcohols and ether, ester or amide derivatives thereof, glycerol, propylene glycol, 1, 3-propanediol, butylene glycol, dipropylene glycol, pentanediol, methoxydiethylene glycol, polyglycerol-3, polyglycerol-2, glycerol polyether-7, glycerol polyether-26, diglycerol, sorbitol, glucose, methyl glucamide, glyceryl laurate, glyceryl oleate, glyceryl isostearate, propylene glycol monolaurate, PEG-6 glyceryl caprylate/caprate, sorbitan sesquicaprylate, sorbitol laurate, methyl glucose caprate/caprylate/oleate, PEG-7 glyceryl cocoate, fatty methyl ester ethoxylates, alkyl polyglucosides, decyl glucoside, cocoa glucoside, glucose, polysorbate 20, polysorbate 60 and polysorbate 80, alkanoyl methylglucamides, lauroyl methylglucamides, octanoyl/decanoyl methylglucamides, and
the hydrophobic thickener is selected from the group consisting of: nonionic alkanolamides, liquid alkanolamides, ethoxylated C10-C14Alcohols, laureth-1 to laureth-5, dimethyl lauramide/myristamide, PPG-2 hydroxyethyl cocamide, cocamide DIPA, lauramide DIPA, soya amide DIPA; and
water, wherein the weight ratio of water to organic solvent vehicle is from 4:1 to 1: 4.
2. The liquid composition according to item 1, wherein the C derived from a Guerbet acid6-C34The alkyl group has the formula:
Figure BDA0002011799810000041
where n is 1-120, preferably 3, 5, 7, 9 or 13.
3. The liquid composition according to item 1 or 2, wherein the liquid composition further comprises:
20-80% of said polyalkoxylated polyol polyester of formula-2, wherein Q is a radical of a polyol compound:
sugar alcohols, polyols having at least six hydroxyl groups (polyhydroic alcohols) having the general formula HOCH2(CHOH)nCH2OH, mannitol, sorbitol, galactitol, fucitol, iditol, inositol, heptatol, isomalt, maltitol, lactitol, maltotriose, and maltotetraol;
a disaccharide having a glycosidic bond,
the reaction product of dipentaerythritol and pentaerythritol,
dextrin having the chemical structure of (C)6H10O5)nWherein n is a number from 2 to 20,
a dendritic polymer polyol, and
a polyglycerol having 3 to 10 glycerol units and 6 or more hydroxyl groups;
an organic vehicle selected from the group consisting of: an organic solvent, a hydrophobic thickener, or a mixture thereof,
the organic solvent is selected from the group consisting of: mono-or polyhydric alcohols and ether, ester or amide derivatives thereof, glycerol, propylene glycol, 1, 3-propanediol, butylene glycol, dipropylene glycol, pentanediol, methoxydiethylene glycol, polyglycerol-3, polyglycerol-2, glycerol polyether-7, glycerol polyether-26, diglycerol, sorbitol, glucose, methyl glucamide, glyceryl laurate, glyceryl oleate, glyceryl isostearate, propylene glycol monolaurate, PEG-6 glyceryl caprylate/caprate, sorbitan sesquicaprylate, sorbitol laurate, methyl glucose caprate/caprylate/oleate, PEG-7 glyceryl cocoate, fatty methyl ester ethoxylates, alkyl polyglucosides, decyl glucoside, cocoa glucoside, glucose, polysorbate 20, polysorbate 60 and polysorbate 80, alkanoyl methylglucamides, lauroyl methylglucamides, octanoyl/decanoyl methylglucamides, and
the hydrophobic thickener is selected from the group consisting of: nonionic alkanolamides, liquid alkanolamides, ethoxylated C10-C14Alcohols, laureth-1 to laureth-5, dimethyl lauramide/myristamide, PPG-2 hydroxyethyl cocamide, cocamide DIPA, lauramide DIPA, soya amide DIPA; and
water, wherein the weight ratio of water to organic solvent vehicle is from 4:1 to 1: 4.
4. The liquid composition according to any one of the preceding items, wherein the liquid thickener composition further comprises:
20-80% of said polyalkoxylated polyol polyester of formula-2, wherein Q is a radical of a polyol compound:
sugar alcohols, polyols having at least six hydroxyl groups (polyhydroic alcohols) having the general formula HOCH2(CHOH)nCH2OH, mannitol, sorbitol, galactitol, fucitol, iditol, inositol, heptatol, isomalt, maltitol, lactitol, maltotriose, maltotetraitol and polyalditol,
a disaccharide formed from two monosaccharides by dehydration via a glycosidic bond,
the reaction product of dipentaerythritol and pentaerythritol,
dextrin having the chemical structure of (C)6H10O5)nWherein n is 2 to 20, and
a dendritic polymer polyol;
the organic vehicle is selected from the group consisting of: an organic solvent, a hydrophobic thickener, or a mixture thereof,
the organic solvent is selected from the group consisting of: mono-or polyhydric alcohols and ether, ester or amide derivatives thereof, glycerol, propylene glycol, 1, 3-propanediol, butylene glycol, dipropylene glycol, pentanediol, methoxydiethylene glycol, polyglycerol-3, polyglycerol-2, glycerol polyether-7, glycerol polyether-26, diglycerol, sorbitol, glucose, methyl glucamide, glycerol laurate, glycerol oleate, glycerol isostearate, propylene glycol monolaurate, PEG-6 caprylic/capric glyceride, sorbitan caprylate/caprate, sorbitan sesquicaprate, sorbitol laurate, methyl glucose caprate/caprylate/oleate, PEG-7 glyceryl cocoate, fatty methyl ester ethoxylates; alkyl polyglucosides such as decyl glucoside, coco glucoside; polysorbate 20, polysorbate 60 and polysorbate 80; alkanoyl methylglucamides, lauroyl methylglucamides, octanoyl/decanoyl methylglucamides, and
the hydrophobic thickener is selected from the group consisting of: nonionic alkanolamides, liquid alkanolamides, ethoxylated C10-C14Alcohols, laureth-1 to laureth-5, and dimethyl lauramide/myristamide, PPG-2 hydroxyethyl cocamide, cocamide DIPA, lauramide DIPA, soya amide DIPA; and
water, wherein the weight ratio of water to organic solvent vehicle is from 4:1 to 1: 4.
5. The liquid composition of any one of the preceding items, wherein the liquid composition further comprises:
20% to 80% of a compound of formula-2 wherein Q is the group of sorbitol, trehalose, mannitol, dipentaerythritol, sucrose, lactose, chitobiose, cellobiose and maltose;
the organic vehicle is selected from the group consisting of: an organic solvent, a hydrophobic thickener or a mixture thereof, wherein
The organic solvent is selected from the group consisting of: mono-or polyhydric alcohols and ether, ester or amide derivatives thereof, glycerol, propylene glycol, 1, 3-propanediol, butylene glycol, dipropylene glycol, pentanediol, methoxydiethylene glycol, polyglycerol-3, polyglycerol-2, glycerol polyether-7, glycerol polyether-26, diglycerol, sorbitol, glucose, methyl glucamide, glyceryl laurate, glyceryl oleate, glyceryl isostearate, propylene glycol monolaurate, PEG-6 glyceryl caprylate/caprate, sorbitan sesquicaprylate, sorbitol laurate, methyl glucose caprate/caprylate/oleate, PEG-7 glyceryl cocoate, fatty methyl ester ethoxylates, alkyl polyglucosides, decyl glucoside, cocoa glucoside, glucose, polysorbate 20, polysorbate 60 and polysorbate 80, alkanoyl methylglucamides, lauroyl methylglucamides, and octanoyl/decanoyl methylglucamides, and
the hydrophobic thickener is selected from the group consisting of: nonionic alkanolamides, liquid alkanolamides, ethoxylated C10-C14Alcohols, laureth-1 to laureth-5, dimethyl lauramide/myristamide; PPG-2 hydroxyethyl cocamide, cocamide DIPA, lauramide DIPA, soyamide DIPA; and
water, wherein the weight ratio of water to organic solvent vehicle is from 4:1 to 1: 4.
6. The liquid composition of any one of the preceding items, wherein the liquid composition further comprises:
20% to 80% of a compound of formula-2 wherein Q is the group of sorbitol, trehalose, mannitol, dipentaerythritol, sucrose, lactose, chitobiose, cellobiose and maltose;
the organic carrier, or a mixture thereof, selected from the group consisting of: alkyl polyglucosides, alkyl methyl glucamides, sorbitan laurate, sorbitan caprylate/caprate, liquid nonionic alkanolamide surfactants, laureth-1, laureth-2, laureth-3, glyceryl caprylate/caprate and glyceryl laurate; and
water, wherein the weight ratio of water to organic solvent vehicle is from 4:1 to 1: 4.
7. The liquid composition of any one of the preceding items, wherein the liquid composition further comprises:
20% to 80% of a compound of formula-2 wherein Q is the group of sorbitol, trehalose, mannitol, dipentaerythritol, sucrose, lactose, chitobiose, cellobiose and maltose;
the organic carrier or a mixture thereof selected from the group consisting of alkanolamides; and
water, wherein the weight ratio of water to organic solvent vehicle is from 4:1 to 1: 4.
8. A cosmetic, dermatological or pharmaceutical composition in the form of a hair cleansing/treatment preparation, a skin and body cleansing/treatment preparation and other rinse preparations comprising a liquid thickener composition according to any of the preceding items.
9. A cosmetic, dermatological or pharmaceutical composition comprising a liquid thickener composition according to item 5 in the form of a hair cleansing/treatment preparation, a skin and body cleansing/treatment preparation and other rinse preparations.
10. The cosmetic, dermatological and pharmaceutical composition according to item 7, further comprising
Water, and
1-50% by weight of a surfactant selected from the group consisting of: anionic surfactants, cationic surfactants, nonionic surfactants, amphoteric surfactants, and mixtures thereof;
from 0.1% to 15% of said liquid thickener composition of formula-2; and
0.1% to 60% of other ingredients selected from the group consisting of: skin and hair actives, stabilizers, other thickeners, and other conventional personal cleansing ingredients.
11. The cosmetic, dermatological and pharmaceutical composition according to item 9, further comprising
Water, and
1-50% by weight of a surfactant selected from the group consisting of: anionic surfactants, cationic surfactants, nonionic surfactants, amphoteric surfactants, and mixtures thereof;
from 0.1% to 15% of said liquid thickener composition of formula-1; and
0.1% to 60% of other ingredients selected from the group consisting of: skin and hair actives, stabilizers, other thickeners, and other conventional personal cleansing ingredients.
12. A cosmetic, dermatological or pharmaceutical composition of about 1% to 8% of the liquid composition according to any one of items 1 to 7, further comprising:
from about 1% to 25% by weight of skin and hair active ingredients selected from the group consisting of: UV filters, moisturizers, conditioners, preservatives, deodorant actives, reducing agents for permanent products, colorants for hair coloring, anti-aging actives, fragrances, petrolatum, vegetable oils, cationic conditioning polymers, and mixtures thereof; and
and (3) water.
13. The composition of any of clauses 1 to 7, wherein the guerbet acid moiety has from 16 to 32 carbons.
14. The composition of any of clauses 1 to 7, wherein the guerbet acid moiety has from 18 to 24 carbons.
15. The composition of any of clauses 1 to 7, wherein the Guerbet acid moiety has 20 carbons.
As an example, formula-3 is the chemical structure of the polyalkoxylated polyol ester of formula-2, wherein Q is the group of the organic polyol compound sorbitol.
Figure BDA0002011799810000081
Formula-3 is the reaction product of (a) a fatty acid and (b) an alkoxylated sorbitol, wherein A is a chemical group-C2H4-or-C3H6-; r is hydrogen or of the formula-COR1Group of (A), R1Is C6-C34Alkyl radical, C6-C22Hydroxyalkyl radical, C2-C22Alkenyl or mixtures thereof, and R1The total number of groups is 3-6. Preferred R1Derived from stearic acid, isostearic acid, oleic acid, guerbet acid or mixtures thereof. Most preferred R1Is oleic acid, and n1、n2、n3、n4、n5And n6Is an integer from 1 to 120, and the average n is from 25 to 100.
Guerbet acids are primary carboxylic acids with well-defined carbon chain twin branches (formula-4). This unique branched structure results in lower melting point, lower viscosity and better solubility. Examples of commercial products are from the Sasol company (Sasol)
Figure BDA0002011799810000084
In the range of 12 carbons to 32 carbons. The preferred carbon range is 16 to 32 carbons, most preferably 18 to 24 carbons, and the most preferred number of carbons is 20.
Figure BDA0002011799810000082
The branched guerbet acid derived moiety has the formula:
Figure BDA0002011799810000083
wherein n is 1-120. Symbol
Figure BDA0002011799810000085
Represents the attachment site of the moiety to the carbon atom of-COR 1. In other words, "derived from a Guerbet acid" means R1(alkyl, alkenyl or hydroxyalkyl) together with-COOH form a Guerbet acid. The flowable liquid thickener of embodiments of the present invention comprises (a) from 20% to 90% and preferably from 30% to 70%, by weight of the total composition, of a polyalkoxylated polyol polyester of formula-2; (b) an organic vehicle selected from the group consisting of organic solvents and liquid hydrophobic thickeners, or mixtures thereof, each as defined below; and (c) water. The ratio of water to organic solvent/hydrophobic thickener is from 4:1 to 1:4, preferably from 2:1 to 1: 2.
The organic solvent is in principle a water-soluble or water-dispersible solvent. Selected from the group consisting of monohydric or polyhydric alcohols and ether, ester or amide derivatives thereof. Examples of alcohols include, but are not limited to, propylene glycol, 1, 3-propanediol, butylene glycol, dipropylene glycol, pentylene glycol, methoxydiglycol, glycerol, polyglycerol-2, polyglycerol-3, glycerol polyether-7, glycerol polyether-26, diglycerol, sorbitol, glucose, methyl glucamide, and the like. Examples of ester, ether and amide derivatives thereof include, but are not limited to, PEG-6 glyceryl caprylate/caprate, sorbitan sesquicaprate, sorbitol laurate, polyglycerol-2 caprylate/caprate, polyglycerol-3 laurate, PEG-7 glyceryl cocoate; fatty methyl ester ethoxylates; alkyl polyglucosides such as decyl glucoside, coco glucoside, etc.; polysorbate 20, polysorbate 60 and polysorbate 80; and alkanoyl methylglucamides (known under the trade name Glucotaine), such as lauroyl methylglucamide, octanoyl/decanoyl methylglucamide, and the like.
Hydrophobic thickeners are low molecular weight thickeners that increase the viscosity of the surfactant in water by affecting the surfactant assembly in the water. One class of hydrophobic thickeners are alkanolamides, which are condensates of fatty acids or triglycerides with alkanolamines such as monoethanolamine, diethanolamine, monoisopropylamine, diisopropylamine, and other alkoxylated amines. Preferred alkanolamides are alkanolamides which are liquid above 15 ℃. Examples of liquid nonionic alkanolamides include, but are not limited to, PPG-2 hydroxyethyl cocamide, cocamide DIPA, lauramide DIPA, soyamide DIPA, cocamide DEA, lauramide DEA, and the like. Other classes of hydrophobic thickeners include ethoxylated C10-C14Alcohols and dimethyl lauramide/myristamide.
Another embodiment of the present invention is a personal care, cosmetic, dermatological, and pharmaceutical formulation containing the liquid thickener composition of an embodiment of the present invention. The liquid thickener compositions of the embodiments of the present invention are suitable as thickeners, rheology modifiers, dissolving agents, and dispersing agents for aqueous, aqueous/alcoholic, and surfactant-containing formulations; as emulsifying and suspending agents with thickening and thickening action for emulsions and suspensions. Such surfactant-containing preparations, emulsions and suspensions are, for example, shampoos, bath preparations, shower gels, foam baths, facial cleansers, hand soaps, bar soaps, shaving creams, hair conditioners, deodorants, lotions, creams, ointments, wet wipes, antiperspirants, sunscreens, etc. Embodiments of the present invention are also suitable as thickeners and rheology modifiers for fabric care products, such as fabric conditioners and liquid laundry detergents.
The formulations of the cleaning formulations and of the emulsions and suspensions according to the invention preferably comprise from 0.05% to 25% by weight, particularly preferably from 0.1% to 15% by weight, particularly preferably from 0.5% to 10% by weight, based on the final formulation, of the liquid thickeners according to the invention.
The cleaning compositions according to embodiments of the present invention may further comprise the following ingredients: all conventional anionic, cationic, zwitterionic, nonionic and amphoteric surfactants; all conventional skin and hair benefit actives such as cosmetic oils, petrolatum, vegetable oils, hydrogenated vegetable oils, UV filters, proteins, shine agents, anti-aging agents, amino acids, biological actives, moisturizers, conditioning polymers, silicones, cationic polymers, sucrose polyesters, anti-dandruff zinc salts, hydroxy acids, skin whitening agents; all conventional stabilizers, such as silica, 12-hydroxystearic acid, hydrogenated castor oil, ethylene glycol distearate, bentonite and hectorite clays, fatty acids, fatty alcohols; all conventional thickeners, such as hydroxyethyl cellulose, xanthan gum, polyacrylates, modified or unmodified starches, and the like; all conventional dyes, colorants, pearlescers, fragrances, chelating agents, solvents, humectants, salts and the like.
The total amount of surfactant used in embodiments of the present invention may be between 5 and 70 wt%, preferably between 10 and 40 wt%, and most preferably between 12 and 35% based on the final composition.
Definition of
As used above, and throughout this disclosure, the following terms are to be understood to have the following meanings, unless otherwise indicated. In the absence of a definition, the conventional definition known to those skilled in the art prevails.
As used herein, the terms "comprising," "including," and "containing" are used in their open, non-limiting sense.
As used herein, the singular forms "a", "an" and "the" include plural referents unless the context clearly dictates otherwise.
To provide a more concise description, some of the quantitative representations given herein are not appropriate for the term "about". It is understood that, whether the term "about" is used explicitly or not, every quantity given herein is meant to refer to the actual given value, and it is also meant to refer to the approximation to such given value that would reasonably be inferred based on the ordinary skill in the art, including equivalents and approximations due to the experimental and/or measurement conditions for such given value. Whenever a yield is given as a percentage, such yield refers to the mass of an entity for which the yield is given relative to the maximum amount of the same entity that can be obtained under the particular stoichiometric conditions. Unless otherwise specified, concentrations given in percentages refer to mass ratios.
As used herein, "alkyl" means a straight or branched saturated chain having 1 to 30 or more carbon atoms. Alkyl groups may be unsubstituted or substituted. Alkyl groups containing three or more carbon atoms may be straight-chain, branched-chain or cyclic.
As used herein, "alkenyl" includes unbranched or branched hydrocarbon chains having one or more double bonds therein and having 1 to 30 or more carbon atoms. The double bond of the alkenyl group may be unconjugated or conjugated to another unsaturated group. Alkenyl groups may be unsubstituted or substituted.
The term "hydroxy" means an OH group;
the term "hydroxyalkyl" means an alkyl group as defined above wherein the alkyl group has an OH group disposed thereon.
The term "alkoxy" or "alkoxylated" as used herein includes-O- (alkyl), wherein alkyl is as defined above.
As used herein, the term "composition" is intended to encompass a product comprising the specified ingredients in the specified amounts, as well as any product which results, directly or indirectly, from combination of the specified ingredients in the specified amounts.
The term "amino" as used herein means a substituent containing at least one nitrogen atom.
As used herein, the term "substituted" means that a particular group or moiety bears one or more suitable substituents, wherein a substituent may be attached at one or more positions to the particular group or moiety.
As used herein, the term "unsubstituted" means that the specified group bears no substituents.
Any atom represented herein having a valence that is not met or specified is considered to have a sufficient number of hydrogen atoms to meet the valence of the atom. For example, "substituted with oxygen" or "substituted with nitrogen" means that the substituents are oxygen bonded to one hydrogen (-OH) through one bond or without hydrogen (O) through two bonds and nitrogen bonded to two hydrogen (-NH2) through one bond or with one hydrogen (NH) through two bonds.
Detailed Description
An object of an embodiment of the present invention is a flowable liquid thickener comprising a high concentration of polyalkoxylated polyol polyester of formula-2, an organic vehicle, and water that is easy to use. The liquid composition is very simple and can be easily added to a container at room temperature or higher during the manufacture of cosmetic, dermatological and pharmaceutical compositions (e.g. shampoos, shower gels, etc.).
The polyalkoxylated polyol polyester (formula-2) of the present invention is prepared by one or more reaction stages: alkoxylation of polyol compounds followed by esterification with fatty acids.
Q-[(OA)n-OR]m
Formula-2
Polyalkoxylated polyols were prepared by: after drying a mixture of a polyol compound and an alkali catalyst such as KOH, NaOH, or calcium metal under vacuum at 100-200 ℃, a polyol compound having 6 to 20 hydroxyl groups is alkoxylated with ethylene oxide or propylene oxide at 130-200 ℃. The alkylene oxide is metered into the reactor under pressure over a period of 10 to 20 hours. Ethylene oxide, propylene oxide, or mixtures of ethylene oxide and propylene oxide may be used to provide primary-OH groups, secondary-OH groups, or mixtures thereof.
The polyol compound of the present invention may be a natural polyol or a synthetic polyol having six hydroxyl groups or more, and examples thereof are shown by the following classes of compounds (but not limited thereto):
1. sugar alcohols, also known as polyols having at least six hydroxyl groups (polyhydroxyl/polyalchol), have the general formula HOCH2(CHOH)nCH2And (5) OH. Examples include, but are not limited to, mannitol, sorbitol, galactitol, fucitol, iditol, inositol, heptatol, isomalt, maltitol, lactitol, maltotriose, maltotetraitol, and polyalditol.
2. Disaccharides, which are formed by dehydration of two monosaccharides via a glycosidic bond. Examples include, but are not limited to, trehalose, sucrose, lactose, maltose, and the like. Which contains six or more hydroxyl groups.
3. Dipentaerythritol
4. Dextrin having the chemical structure of (C)6H10O5)nWherein n is 2 to 20.
5. A dendritic polymer polyol. For example,
Figure BDA0002011799810000111
h2004, H2003 and H20 have 6, 12 and 16 terminal hydroxyl groups respectively,
Figure BDA0002011799810000112
is the trade name of boston corporation (Perstorp Inc).
6. Polyglycerol having 3 to 10 glycerol units with 6 or more hydroxyl groups.
After the reaction, each hydroxyl group of the starting polyol compound will grow into a hydrophilic poly (alkylene glycol) arm. The length of all arms may be the same or different depending on the reaction conditions.
The next reaction is an esterification reaction between the alkoxylated polyol compound and the fatty acid such that some or all of the hydrophilic poly (alkylene glycol) arms are capped with the fatty acid ester. The reaction is carried out between 120 ℃ and 250 ℃ with or without a catalyst until the desired acid number or degree of esterification is reached. The preferred method is to use an esterification catalyst such as an alkyl benzene sulfonic acid, methane sulfonic acid, an organotin catalyst, an organotitanate catalyst, and the like. The preferred molar ratio of fatty acid to alkoxylated polyol compound is to form an ester having from 30% to 100% hydrophilic poly (alkylene glycol) arms. For example, when the starting polyol compound is sorbitol, which will produce six poly (alkylene glycol) arms per sorbitol molecule, the molar ratio will be 2.4 to 6, resulting in a structure of formula-3. When it is trehalose, the molar ratio is from 3.2 to 8 when eight poly (alkylene glycol) arms will be produced. Most preferably, more than at least four fatty ester terminated arms are formed.
Figure BDA0002011799810000121
Q of formula-2 is defined as the radical of an organic polyol compound wherein the radical structure is derived from a polyol by removal of one or more, preferably all, of the corresponding OH-groups, has the elements carbon, hydrogen, oxygen and nitrogen, and has 6 to 50 carbon atoms, and is a saturated or unsaturated, linear, branched or cyclic chain, and is independently substituted with 6 to 25 groups having the formula [ (OA)n-OR]Is substituted with a group (b). Wherein A is selected from-C2H4-or-C3H6-; and n is 1 to 125; r is independently selected from hydrogen or-COR1(ii) a And R is1Independently selected from C6-C34Alkyl radical, C6-C22Hydroxyalkyl radical, C2-C22An alkenyl group; wherein R is1Preferably derived from stearic acid, isostearic acid, oleic acid, Guerbet acid or mixtures thereof, and preferably oleic acid or Guerbet acid, or a combination of Guerbet acid and isostearic acid, and COR1Is not less than 2.5, preferably not less than 3, and most preferably not less than 4. N of the hydrophilic poly (alkylene glycol) arms is an integer from 1 to 125, and may be the same or different for all arms. The average number of n per hydrophilic poly (alkylene glycol) arm is from 25 to 120, preferably from 30 to 85, and most preferably from 30 to 70.
Guerbet acids are primary carboxylic acids with well-defined carbon chain twin branches (formula-4). This unique branched structure results in lower melting point, lower viscosity and better solubility. The preferred carbon range is 16 to 32 carbons, most preferably 18 to 24 carbons, and the most preferred number of carbons is 20.
The flowable liquid thickener of embodiments of the present invention comprises (a) from 20% to 90% and preferably from 30% to 70%, by weight of the total composition, of a polyalkoxylated polyol polyester of formula-2; (b) an organic vehicle selected from the group consisting of organic solvents and liquid hydrophobic thickeners, or mixtures thereof, each as defined below; and (c) water. The ratio of water to organic solvent/hydrophobic thickener is from 4:1 to 1:4, and preferably from 2:1 to 1: 2.
The organic solvent is in principle a water-soluble or water-dispersible solvent. Selected from the group consisting of monohydric or polyhydric alcohols and ether, ester or amide derivatives thereof. Examples of alcohols include, but are not limited to, propylene glycol, 1, 3-propanediol, butylene glycol, dipropylene glycol, pentylene glycol, methoxydiglycol, glycerol, polyglycerol-2, polyglycerol-3, glycerol polyether-7, glycerol polyether-26, diglycerol, sorbitol, glucose, methyl glucamide, and the like. Examples of ester, ether and amide derivatives thereof include, but are not limited to, PEG-6 glyceryl caprylate/caprate, sorbitan sesquicaprate, sorbitol laurate, polyglycerol-2 caprylate/caprate, polyglycerol-3 laurate, PEG-7 glyceryl cocoate; fatty methyl ester ethoxylates; alkyl polyglucosides such as decyl glucoside, coco glucoside, etc.; polysorbate 20, polysorbate 60 and polysorbate 80; and alkanoyl methylglucamides (known under the trade name Glucotaine), such as lauroyl methylglucamide, octanoyl/decanoyl methylglucamide, and the like.
Hydrophobic thickeners are low molecular weight thickeners that increase the viscosity of the surfactant in water by affecting the surfactant assembly in the water. One class of hydrophobic thickeners are alkanolamides, which are condensates of fatty acids or triglycerides with alkanolamines such as monoethanolamine, diethanolamine, monoisopropylamine, diisopropylamine, and other alkoxylated amines. Preferred alkanolamides are alkanolamides which are liquid above 15 ℃. Liquid nonionic alkanesExamples of alkanolamides include, but are not limited to, PPG-2 hydroxyethyl cocamide, cocamide DIPA, lauramide DIPA, soyamide DIPA, cocamide DEA, lauramide DEA, and the like. Other classes of hydrophobic thickeners include ethoxylated C10-C14Alcohols and dimethyl lauramide/myristamide. From Stepan
Figure BDA0002011799810000131
CAA is a commercial example of the dimethyl lauramide/myristamide class.
Another embodiment of the present invention is a cosmetic and pharmaceutical formulation containing a flowable liquid thickener composition. The liquid compositions of the embodiments of the present invention are suitable as thickeners, rheology modifiers, solubilizers, and dispersants for aqueous, aqueous/alcoholic, and surfactant-containing formulations; as emulsifying and suspending agents with thickening and thickening action for emulsions and suspensions. Such surfactant-containing preparations, emulsions and suspensions are, for example, shampoos, bath preparations, shower gels, foam baths, facial cleansers, hand soaps, bar soaps, shaving creams, hair conditioners, deodorants, lotions, creams, ointments, wet wipes, antiperspirants, sunscreens, etc.
The formulations of the cleaning preparations, emulsions and suspensions according to the invention preferably comprise, based on the final formulation, from 0.05% to 25% by weight, particularly preferably from 0.1% to 15% by weight, particularly preferably from 0.5% to 10% by weight, of the ready-to-use liquid thickener compositions according to the invention containing polyalkoxylated polyol polyesters of the formula-2.
Cleaning compositions according to embodiments of the present invention may further comprise the following components: all conventional anionic, cationic, zwitterionic, nonionic and amphoteric surfactants; skin and hair benefit actives such as cosmetic oils, petrolatum, vegetable oils, hydrogenated vegetable oils, UV filters, proteins, shine agents, anti-aging agents, amino acids, bioactives, moisturizers, conditioning polymers, silicones, cationic polymers, sucrose polyesters, anti-dandruff zinc salts, hydroxy acids, skin whitening agents, and the like; stabilizers such as silica, 12-hydroxystearic acid, hydrogenated castor oil, ethylene glycol distearate, bentonite and hectorite clays, fatty acids, fatty alcohols, and the like; other thickeners such as hydroxyethyl cellulose, xanthan gum, polyacrylates, modified or unmodified starches, and the like; and polyethylene glycol. The cleaning compositions may be in the form of a liquid, paste, gel or solid and may be used for personal cleaning, fabric cleaning and hard surface cleaning.
The total amount of surfactant used in the composition of the present invention may be between 5 and 70 wt%, preferably between 10 and 40 wt%, and most preferably between 12 and 35 wt%, based on the final composition.
Each of these components, as well as preferred and optional components, in the cleaning composition are described below.
A. Detersive surfactant
Conventional detersive surfactants can be selected from anionic, cationic, nonionic, amphoteric/zwitterionic surfactants or mixtures thereof. Details of these conventional detersive surfactants have been cited in many prior art, such as US7,659,235B 2; 8,361,450B 2; 8,802,607B 2; 3,929,678; 2,528,378, which are all incorporated by reference; and McCutcheon's, Emulsifiers and Detergents (1989) published by m.c. publishing Co (m.c. publishing Co). Anionic surfactants may include alkyl sulfates or alkyl ether sulfates (including alkyl glyceryl ether sulfates). It may also include sulfate-free anionic surfactants as shown below.
Aliphatic sulfonates, including but not limited to primary alkanes (e.g. C)8-C22) Sulfonates, primary alkane disulfonates, C8-C22Olefin sulfonates, alkyl glyceryl ether sulfonates, aromatic alkyl sulfonates or C8-C22A hydroxyalkane sulfonate.
Alkyl sulfosuccinates (including monoalkyl and dialkyl, e.g. C)6-C22Sulfosuccinates), alkyl and acyl taurates, alkyl and acyl glycinates, alkyl sulfoacetates, alkyl phosphatesAlkyl phosphate, alkoxyalkyl phosphate and acyl lactate, C8-C22Monoalkylsuccinates and maleates. Fatty acyl isethionates, which are typically prepared by the reaction of isethionates, such as alkali metal isethionates, and aliphatic fatty acids of 8 to 20 carbon atoms. For example, commercial products of fatty acyl isethionates are DEFI, Hostapon SCI-78C, Jordapon CI print, YA-SCI-85, Iselux LQ-CLR-SB, and the like. Having the formula R- (CH)2CH2O)nCO2M wherein R is C8-C20An alkyl group; n is 1 to 20; and M is a positive ion, such as sodium, potassium, and the like. Another class of anionic surfactants are soaps or fatty acid salts. Sulfonate derivatives of alkyl polyglucosides include, for example, sodium lauryl glucoside hydroxypropyl sulfonate and sodium decyl glucoside and hydroxypropyl sulfonate.
Other sulfate-free mild surfactants are a class of alkanoyl surfactants prepared from amino acids. Alkyl is C8To C20Preferably C12To C16An alkyl group. Such surfactants may include, for example, alkanoyl sarcosinates, alkanoyl glycinates and alkanoyl glutamates. For example, the commercial product is of Ajinamoto
Figure BDA0002011799810000141
Figure BDA0002011799810000142
Eversoft et al, of the middle Lion chemical company (Sino Lion).
Preferred anionic surfactants are sulfate-free mild surfactants and mixtures thereof. The weight proportion of anionic surfactant in the composition according to the invention is in the range from 5 to 35% by weight, preferably from 10 to 25% by weight.
Amphoteric or zwitterionic surfactants are surfactants having a positive and a negative charge. It can be broadly described as a derivative of an aliphatic quaternary ammonium, phosphonium, sulfonium compound in which the aliphatic radical can be straight or branched chain, and whereinOne of the aliphatic radicals being C8To C18Carbon atoms and one containing an anionic group, e.g. carboxy, sulfonate, sulfate, phosphate or phosphonate. Examples may include conventional betaines, such as ammonium N-alkyl-N, N-dimethylglycinate, cocamidopropyl betaine; c12-C18Alkyl dimethyl-sulfopropyl betaines and amine oxides. The proportion of amphoteric surfactant in the composition according to the invention is from 0.5% to 30% by weight, and preferably from 1% to 15% by weight.
The nonionic surfactant may include alkoxylated fatty alcohols, acids, amides or alkyl phenols; long chain tertiary amine oxides; long chain tertiary phosphine oxides; a dialkyl sulfoxide; sugar amides, as described in US5,389,279 and 5,009,814; alkyl polyglucosides, as described in US 4,565,647 and 3,723,325, all of which are incorporated by reference. Preferred nonionic surfactants are alkyl polyglucosides and alkyl polyglucosamides. Examples of commercial products may include those of BASFSeries, Dow Chemicals
Figure BDA0002011799810000153
Series, Gluco by Clariant
Figure BDA0002011799810000152
And Poly SugaMuls by Colonial Chemicals. The proportion of the nonionic surfactant according to the present invention is in the range of 1 to 20% by weight, and preferably 1 to 15%.
Cationic surfactants are surfactants having positively charged groups. Suitable cationic surfactants may include quaternary ammonium salts, such as di (C)10-C24) Alkyl dimethyl ammonium chloride, (C)10-C24) Alkyl trimethylammonium chloride or sulphate, and N-acylaminoethyl-N, N-diethyl-N-methylammonium chloride. Other conventional cationic surfactants are described in US8,470,305 and 8,470,305, which are incorporated by reference. The weight proportion of cationic surfactant in the composition according to the invention is in the range from 1 to 10% by weight, and preferably from 1 to 7% by weight.
B.Liquid crystal inducer and modifier
Liquid crystal inducers are small, non-ionic molecules. It is believed to dissolve in the mixture of surfactants and alter the surfactant micelles to form a stack of larger structural aggregates of different shapes and sizes, such as lamellar liquid structures or vesicles, rods and cubic liquid crystals. An alternative name for liquid crystal inducers is hydrophobic thickeners. It includes the classes alkanolamide, alkylamine oxide or mixtures thereof. Examples of this class include monoethanolamides and diethanolamides, isopropanolamides of fatty acids of 10 to 20 carbon atoms, PPG-hydroxyethyl cocamide, and alkylamine oxides of 10 to 20 carbon atoms. Another class of chemicals in liquid crystal inducers are alkoxylated alkyl alcohols of 8 to 18 carbon atoms, preferably 8 to 12 carbon atoms, and 1 to 4 ethylene oxide units.
The liquid crystal modifier comprises fatty acid and fatty alcohol with 8-20 carbon atoms and aliphatic hydrocarbon with molecular weight less than 400 g/mol. It is believed to change the size and shape of the liquid crystal. US7,655,607B 2 (incorporated by reference) is a reference to the scope and examples of liquid crystal inducers and modifiers.
C.Skin and hair benefit actives
These benefit actives may be water soluble, water insoluble or water dispersible. Water soluble actives may include, but are not limited to, polyols such as glycerol, diglycerol, sorbitol, propylene glycol (propylene glycol), propylene glycol (propandiol), panthenol, and sugars; alpha-hydroxy acids and salts thereof and low molecular weight polyethylene glycols. Water insoluble and water dispersible skin and hair benefit actives include, but are not limited to, petrolatum, silicones, vegetable oils, essential oils, emollients, hydrocarbon oils, fatty esters, cationic polymers, high refractive index oils for lightening, anti-dandruff agents, protein/protein derivatives, and the like. These water insoluble benefit agents are typically present in the composition as an emulsion or a stripe. Non-limiting examples in US7,262,158 are incorporated herein by reference. Other various skin and hair benefit actives may include vitamins, lipids (sucrose esters, lanolin, cholesterol, etc.), liposomes, essential fatty acids, butter, minerals, antimicrobials, anti-acne agents, oil control agents, astringents, oil control agents, scrub and exfoliate particles, essential oils, sunscreens, styling aids, dyes, perfumes, cyclodextrin/perfume complexes, anti-wrinkle actives (amino acids and derivatives thereof such as N-acetyl-L-cysteine), thiols, anti-cellulite agents (caffeine, theophylline, etc.), tanning actives, skin whitening actives, skin soothing agents (such as bisabolol, aloe, dipotassium glycyrrhizinate, etc.).
Cationic water-soluble/dispersible polymers are very useful as conditioning actives or deposition aids for compositions according to embodiments of the present invention. Suitable cationic polymers for use in the composition according to the invention have a cationic charge density in the range of from 0.2 to 8meq/g and a molecular weight in the range of from 1,000 to 3,000,000. The cationic groups thereof are nitrogen-containing moieties, such as quaternary ammonium or cationic protonated amino moieties, which can be primary, secondary and tertiary amines. Non-limiting examples of cationic polymers are described in the CTFA Cosmetic Ingredient Dictionary (CTFA Cosmetic Ingredient Dictionary), 3 rd edition, edited by emerson (estin), crohn (cross), and Haynes (Haynes), which are incorporated herein by reference, as well as US 8470,305 and US8,105,994.
Non-limiting examples can include copolymers of vinyl monomers having cationic protonated amine or quaternary ammonium functionalities with water-soluble spacer monomers such as acrylamide, methacrylamide, alkyl and dialkyl acrylamides, vinyl pyrrolidone, vinyl caprolactone, and the like. Non-limiting specific examples are polyquaternium-11, -16, -7, -6, -22, -47, -39. Other suitable cationic polymers include polysaccharide polymers such as cationic cellulose derivatives, cationic starch derivatives, cationic guar gum derivatives, and the like. Non-limiting examples include the following trade names: from Rhonepoulenc
Figure BDA0002011799810000161
From the sub-span dragon company (Aqualon)
Figure BDA0002011799810000162
And N-Hance polymers, UCARE polymers from the Dow chemical company, MerQuat from Nalco, Galactasol from Hangao (Henkel), and the like.
D.Stabilizers and other thickeners
The stabilizer (or structuring system) serves to form a crystalline stabilizing network in the composition, preventing coalescence and phase separation of the droplets of lipophilic benefit agent in the product. Non-limiting examples include hydroxyl-containing fatty acids, fatty esters, or fatty soap water-insoluble waxy materials, such as 12-hydroxystearic acid, 9, 10-dihydroxystearic acid, tris-9, 10-dihydroxystearin, and tris-12 hydroxystearin. Another class of stabilizers is C10-22Ethylene glycol fatty acid esters, fumed silica, precipitated silica, montmorillonite clay, and the like. Examples of other conventional stabilizers are disclosed in US 6,194,363 and US 9,138,428, both of which are incorporated by reference. Another class of stabilizers is the gel network of fatty amphiphiles (e.g. stearic acid and behenyltrimethylammonium chloride), as disclosed in US8,470,305, which is incorporated by reference. Another class of stabilizers is blends of unmodified and modified starches and fatty acids, as disclosed in US 6,906,016, incorporated by reference.
Other thickeners useful for stabilizing and altering the viscosity of the composition according to the present invention are polymers. Non-limiting examples include carbohydrate gums such as cellulose gum, microcrystalline cellulose, cellulose gel, hydroxyethyl cellulose, hydroxypropyl cellulose, sodium carboxymethyl cellulose, methyl/propyl cellulose, guar gum, karaya gum, tragacanth gum, acacia gum, agar gum, xanthan gum, and mixtures thereof; modified and unmodified starch granules having a gelatinization temperature between 30 ℃ and 85 ℃ and pregelatinized cold water soluble starch. Further non-limiting examples include the class of hydrophobically associating, cross-linking, alkali swellable acrylate polymers comprising acidic monomers having hydrophobic end groups and associative monomers as disclosed in US 9,161,899 (incorporated by reference). Non-limiting commercial examples are Carbopol Aqua SF-1 from Lubrizol, Stabylen 30 from 3V Sigma S.P.A., Inc. (3V Sigma S.P.A.), and the Aqupec series from Sumitomo Seika, Japan.
Suitable other thickeners may include salts such as sodium chloride and sodium sulfate; cellulose derivatives such as hydroxyethyl cellulose; xanthan gum, guar gum; starch and starch derivatives; carboxyvinyl polymers, e.g.
Figure BDA0002011799810000171
940; polyacrylate emulsions, e.g.
Figure BDA0002011799810000172
Aqua SF-1 polymers; polyethylene glycol; and polyvinyl alcohol.
According to the invention, the formulation of emulsions and suspensions comprises water; an oil; an emulsifier; preferably from 0.05 to 20% by weight, particularly preferably from 0.1 to 10% by weight, particularly preferably from 0.5 to 5% by weight, of a ready-to-use liquid composition of the formula-1; and other conventional ingredients for skin care, hair care and body care. The non-aqueous portion of the emulsion is typically in the range of 2% to 85%, and preferably 5% to 45%. Oils include, but are not limited to, cosmetic oils that are refined vegetable oils, refined synthetic or fermented hydrocarbon oils, silicone oils, and synthetic ester oils.
The following non-limiting examples demonstrate the compositions and outstanding performance of the present invention.
Examples of the invention
Example 1 Synthesis of polyalkoxylated polyesters of formula-2 having different molecular structures. Table 1 lists the preparation of polyalkoxylated polyol polyesters of formula-2 having a range of molecular weights of alkoxylated sorbitol and fatty acid. The reaction flask used was a one-liter resin kettle with four necks. Sorbitol (polyol) is mixed with KOH or NaOH base catalyst and dried under vacuum at 90 to 110 ℃. X moles of ethylene oxide or ethylene oxide and one mole of sorbitolThe blend of propylene oxide is added under pressure and reacted at 140 ℃ to 180 ℃ over a reaction time of 10-20 hours. After the reaction, the resulting product was cooled, degassed and filtered to give sorbitol polyether-xxx. The ingredients of sorbitol polyether-xxx, oleic or stearic acid, and catalyst-methanesulfonic acid were added to the flask, then purged with nitrogen. The mixture was heated to between 120 ℃ to 220 ℃ while mixing under nitrogen and collecting the water. Continuing the reaction until R1The sum (or acid number) of (a) is targeted or nearly constant. The product was collected after cooling the flask to room temperature. The resulting polyester was a waxy solid.
Figure BDA0002011799810000181
Example 2. easy to use liquid thickeners of the present examples are prepared by mixing polyalkoxylated polyol polyesters of formula-2 above with a suitable solvent or carrier and water. Table 2 shows some non-limiting examples.
Figure BDA0002011799810000182
Example 3 the liquid thickener examples in table 2 can thicken non-sulfate and sulfate surfactant cleaning products. To demonstrate its thickening efficiency, LT-3 liquid thickener was compared to a commercial liquid thickener of the prior art in a non-sulfate surfactant cleansing formulation comprising x% liquid thickener, 8.67% sodium cocoyl glutamate (Amisoft CS-11, supplied by Ajinomoto Inc.), 1% cocamide MEA, 0.3% EDTA, 1% NaCl, and appropriate amounts of water and citric acid adjusted to pH 7, fragrance, preservative. Sources of commercial thickeners: the Crothix Liquid with INCI name PEG-150 pentaerythritol tetrastearate (and) PEG-6 glyceryl caprylate/caprate (and) water and the Versathix with INCI name PEG-150 pentaerythritol tetrastearate (and) PPG-2 hydroxyethyl cocamide (and) water were manufactured by the procumbent company of gore (Croda Inc). The Glutamate VLT is manufactured by Lubrizol under the INCI name PEG-120 methyl glucose trioleate (and) propylene glycol (and) water. Arlypon TT is manufactured by BASF corporation under the INCI name PEG-PPG 120/10-trimethylolpropane trioleate (and) laureth-2.
Figure BDA0002011799810000191
The sodium cocoyl glutamate surfactant is derived from glutamic acid amino acids. It is a well-known mild surfactant. It is also known that it is difficult to thicken; as evidenced by the low thickening performance of well-known commercial thickeners-Crothix liquid, Versathix, Glutamate VLT, and Arlypon TT in table 3. In contrast, LT-3 of the present invention exhibits a thickening efficacy that is more than 3 times greater than all of these commercial thickeners.
Example 4 table 4 shows other non-limiting examples of liquid thickeners of the present invention comprising polyalkoxylated polyol polyesters of formula-2 and a suitable solvent and water.
Figure BDA0002011799810000192
Example 5 several liquid thickeners of the invention in table 4 were formulated into personal cleansing products based on the extremely mild amino acid derived surfactant sodium cocoyl glutamate, sold under the trade name Amisoft CS-11, supplied by the company ajinomoto. Based on the weight of the cleaning product, the composition comprised 77.23% water, 8.67% Amisoft CS-11, 8.0% cocamidopropyl betaine (trade name Monateric LMAB, supplied by Mooney Industries), 4% cocamidopropyl hydroxysultaine (trade name Cola Teric CBS-HP, supplied by Coronel chemical), 1% glyceryl monolaurate, 0.1% EDTA, 1% NaCl, and appropriate amounts of essential oils, preservatives, and the like.
Figure BDA0002011799810000201
Example 6 this example demonstrates the superior performance of the liquid thickener of the present embodiment over commercial thickeners in a classical sulfate surfactant product comprising 10.7% sodium lauryl ether sulfate (70% solution), 8.58% cocamidopropyl betaine (35% solution), 0.25% cocamide MEA, 0.2% EDTA, 0.5% salt, x% thickener, water in appropriate amounts and citric acid adjusted to pH 5.5. 0.31% LT-1 and 0.3% Versathix of Table 2 gave viscosities 16140cP and 4080cP, respectively, in the surfactant formulation. The LT-1 of the invention has thickening performance which is more than 6 times higher than Versathix.
Example 7 this example demonstrates the use of the liquid thickener of the present invention in topical skin care applications. Daily skin lotions are prepared at 65 ℃ to 80 ℃ and comprise by weight a) phase a: 10% caprylic/capric triglyceride, 10% dimethicone oil, and 1.5% cetearyl alcohol and cetearyl glucoside (trade name: Montanov 68, emulsifier, supplied by Seppic Inc.); and B) phase B: 3% LT-2, 3% glycerol, 0.1% EDTA, 0.3% preservative. The pH of the final lotion was 5.8 and the viscosity was 13520cP at 5 rpm.
Example 8. Strong hair cuticle smoothing films for damaged hair after coloring, perming, relaxing, straightening, etc. The hair treatment product comprises, by weight, a) phase a: 89.05% water, 3% glycerol, 0.1% EDTA; b) 1.8% behenyltrimethylammonium chloride, 3% cetearyl alcohol, 0.8% ceteareth-20, 1% argan oil, 1% LT-2; and c) adjusting the pH value to 5.5 by using a proper amount of preservative and citric acid. Phase B was prepared by mixing all the ingredients of phase B at 75 ℃ to 85 ℃ with a propeller. It was added to phase A while mixing at 600-800rpm and 75-85 ℃. After cooling to room temperature, add phase C. The final product was smooth and shear thinning with a viscosity of 16800cP at 5 rpm.
Example 9. table 6 illustrates the latent surfactant formulations of the present examples with skin/hair actives and other additives.
Figure BDA0002011799810000202
Figure BDA0002011799810000211
Example 10. Table 7 of this example illustrates the synthesis of a polyester of formula-1 with a gemini branched Guerbet acid. Commercial Guerbet acids used were Isocab-20 (2-octyl-dodecanoic acid) having 20 carbons and Isocab-24 (2-decyl-tetradecanoic acid) having 24 carbons, supplied by the company Sasolr. The same reaction conditions as in example 1 apply here.
Figure BDA0002011799810000212
Example 11 this example shows a non-limiting example of a liquid thickener composition comprising the polyester of example 10. Table 8 illustrates a potential liquid thickener composition comprising polyester-10 and polyester-11.
Figure BDA0002011799810000213
Figure BDA0002011799810000221
Example 12 this example illustrates the surprising thickening ability of the above Liquid thickeners compared to the commercial product Crothix Liquid. Table 9 shows the composition of two common prototype shampoo bases. Table 10 shows the viscosity of a shampoo prototype and Corthix Liquid with the Liquid thickener of the invention of table 8. Note that in table 10, 3% LT14 exhibited about 37 times higher thickening power than 4.5% Corthix Liquid.
Figure BDA0002011799810000222
Figure BDA0002011799810000223

Claims (15)

1. A liquid thickener composition comprising:
20% to 80% of a polyalkoxylated polyol polyester of formula:
Q-[(OA)n-OR]m
formula-2
Q is a group of an organic polyol compound having 6 to 50 carbon atoms and being a saturated or unsaturated linear, branched or cyclic chain structure in which one or more of the carbon atoms are independently represented by the formula [ (OA)n-OR]Wherein n is 6 to 25,
wherein each of the remaining 6 to 50 carbon atoms is independently substituted with hydrogen, oxygen, or nitrogen,
a is selected from-C2H4-or-C3H6-，
R is independently selected from hydrogen or-COR1，
Wherein COR in said composition1The average total number of the (A) is more than or equal to 2,
R1independently selected from C6-C34Alkyl, preferably derived from a guerbet acid; c6-C22Hydroxyalkyl radicals, preferably derived from guerbet acids; c6-C22Alkenyl, preferably derived from a guerbet acid;
wherein R is1Preferably derived from stearic acid, isostearic acid, oleic acid, Guerbet acid or mixtures thereof,
n is an integer independently selected from 1 to 125, and
m is an integer selected from 6 to 25;
an organic vehicle selected from the group consisting of: an organic solvent, a hydrophobic thickener, or a mixture thereof,
the organic solvent is selected from the group consisting of: mono-or polyhydric alcohols and ether, ester or amide derivatives thereof, glycerol, propylene glycol, 1, 3-propanediol, butylene glycol, dipropylene glycol, pentanediol, methoxydiethylene glycol, polyglycerol-3, polyglycerol-2, glycerol polyether-7, glycerol polyether-26, diglycerol, sorbitol, glucose, methyl glucamide, glyceryl laurate, glyceryl oleate, glyceryl isostearate, propylene glycol monolaurate, PEG-6 glyceryl caprylate/caprate, sorbitan sesquicaprylate, sorbitol laurate, methyl glucose caprate/caprylate/oleate, PEG-7 glyceryl cocoate, fatty methyl ester ethoxylates, alkyl polyglucosides, decyl glucoside, cocoa glucoside, glucose, polysorbate 20, polysorbate 60 and polysorbate 80, alkanoyl methylglucamides, lauroyl methylglucamides, octanoyl/decanoyl methylglucamides, and
the hydrophobic thickener is selected from the group consisting of: nonionic alkanolamides, liquid alkanolamides, ethoxylated C10-C14Alcohols, laureth-1 to laureth-5, dimethyl lauramide/myristamide, PPG-2 hydroxyethyl cocamide, cocamide DIPA, lauramide DIPA, soya amide DIPA; and
water, wherein the weight ratio of water to organic solvent vehicle is from 4:1 to 1: 4.
2. The liquid thickener composition of claim 1, wherein the C derived from a Guerbet acid6-C34The alkyl group has the formula:
Figure FDA0002011799800000021
where n is 1-120, preferably 3, 5, 7, 9 or 13.
3. The liquid thickener composition according to claim 1 or 2, wherein the liquid thickener composition further comprises:
20-80% of the polyalkoxylated polyol polyester of formula-2, wherein said Q is a radical of a polyol compound:
sugar alcohols, polyols having at least six hydroxyl groups (polyhydroic alcohols) having the general formula HOCH2(CHOH)nCH2OH; mannitol, sorbitol, galactitol, fucitol, iditol, inositol, heptatol, isomalt, maltitol, lactitol, maltotriose, and maltotetraol;
a disaccharide having a glycosidic bond,
the reaction product of dipentaerythritol and pentaerythritol,
dextrin having the chemical structure of (C)6H10O5)nWherein n is a number from 2 to 20,
a dendritic polymer polyol, and
a polyglycerol having 3 to 10 glycerol units and 6 or more hydroxyl groups;
an organic vehicle selected from the group consisting of: an organic solvent, a hydrophobic thickener, or a mixture thereof,
the organic solvent is selected from the group consisting of: mono-or polyhydric alcohols and ether, ester or amide derivatives thereof, glycerol, propylene glycol, 1, 3-propanediol, butylene glycol, dipropylene glycol, pentanediol, methoxydiethylene glycol, polyglycerol-3, polyglycerol-2, glycerol polyether-7, glycerol polyether-26, diglycerol, sorbitol, glucose, methyl glucamide, glyceryl laurate, glyceryl oleate, glyceryl isostearate, propylene glycol monolaurate, PEG-6 glyceryl caprylate/caprate, sorbitan sesquicaprylate, sorbitol laurate, methyl glucose caprate/caprylate/oleate, PEG-7 glyceryl cocoate, fatty methyl ester ethoxylates, alkyl polyglucosides, decyl glucoside, cocoa glucoside, glucose, polysorbate 20, polysorbate 60 and polysorbate 80, alkanoyl methylglucamides, lauroyl methylglucamides, octanoyl/decanoyl methylglucamides, and
the hydrophobic thickener is selected from the group consisting of: nonionic alkanolamides, liquid alkanolamides, ethoxylated C10-C14Alcohols, laureth-1 to laureth-5, dimethyl lauramide/myristamide, PPG-2 hydroxyethyl cocamide, cocamide DIPA, lauramide DIPA, soya amide DIPA; and
water, wherein the weight ratio of water to organic solvent vehicle is from 4:1 to 1: 4.
4. The liquid thickener composition according to claim 1 or 2, wherein the liquid thickener composition further comprises:
20-80% of the polyalkoxylated polyol polyester of formula-2, wherein said Q is a radical of a polyol compound:
sugar alcohols, polyols having at least six hydroxyl groups (polyhydroic alcohols) having the general formula HOCH2(CHOH)nCH2OH; mannitol, sorbitol, galactitol, fucitol, iditol, inositol, heptatol, isomalt, maltitol, lactitol, maltotriose, maltotetraitol, and polyalditol,
a disaccharide formed from two monosaccharides by dehydration via a glycosidic bond,
the reaction product of dipentaerythritol and pentaerythritol,
dextrin having the chemical structure of (C)6H10O5)nWherein n is 2 to 20, and
a dendritic polymer polyol;
the organic vehicle is selected from the group consisting of: an organic solvent, a hydrophobic thickener, or a mixture thereof,
the organic solvent is selected from the group consisting of: mono-or polyhydric alcohols and ether, ester or amide derivatives thereof, glycerol, propylene glycol, 1, 3-propanediol, butylene glycol, dipropylene glycol, pentanediol, methoxydiethylene glycol, polyglycerol-3, polyglycerol-2, glycerol polyether-7, glycerol polyether-26, diglycerol, sorbitol, glucose, methyl glucamide, glycerol laurate, glycerol oleate, glycerol isostearate, propylene glycol monolaurate, PEG-6 caprylic/capric glyceride, sorbitan caprylate/caprate, sorbitan sesquicaprylate, sorbitol laurate, methyl glucose caprate/caprylate/oleate, PEG-7 glyceryl cocoate, fatty methyl ester ethoxylates; alkyl polyglucosides such as decyl glucoside, coco glucoside; polysorbate 20, polysorbate 60 and polysorbate 80; alkanoyl methylglucamides, lauroyl methylglucamides, octanoyl/decanoyl methylglucamides, and
the hydrophobic thickener is selected from the group consisting of: nonionic alkanolamides, liquid alkanolamides, ethoxylated C10-C14Alcohols, laureth-1 to laureth-5, and dimethyl lauramide/myristamide, PPG-2 hydroxyethyl cocamide, cocamide DIPA, lauramide DIPA, soya amide DIPA; and
water, wherein the weight ratio of water to organic solvent vehicle is from 4:1 to 1: 4.
5. The liquid thickener composition according to claim 1 or 2, wherein the liquid thickener composition further comprises:
20% to 80% of a polyalkoxylated polyol polyester of formula-2 wherein Q is the group of sorbitol, trehalose, mannitol, dipentaerythritol, sucrose, lactose, chitobiose, cellobiose, and maltose;
the organic vehicle is selected from the group consisting of: an organic solvent, a hydrophobic thickener or a mixture thereof, wherein
The organic solvent is selected from the group consisting of: mono-or polyhydric alcohols and ether, ester or amide derivatives thereof, glycerol, propylene glycol, 1, 3-propanediol, butylene glycol, dipropylene glycol, pentanediol, methoxydiethylene glycol, polyglycerol-3, polyglycerol-2, glycerol polyether-7, glycerol polyether-26, diglycerol, sorbitol, glucose, methyl glucamide, glyceryl laurate, glyceryl oleate, glyceryl isostearate, propylene glycol monolaurate, PEG-6 glyceryl caprylate/caprate, sorbitan sesquicaprylate, sorbitol laurate, methyl glucose caprate/caprylate/oleate, PEG-7 glyceryl cocoate, fatty methyl ester ethoxylates, alkyl polyglucosides, decyl glucoside, cocoa glucoside, glucose, polysorbate 20, polysorbate 60 and polysorbate 80, alkanoyl methylglucamides, lauroyl methylglucamides, and octanoyl/decanoyl methylglucamides, and
the hydrophobic thickener is selected from the group consisting of: non-ionic alkanolamides,Liquid alkanolamide, ethoxylation C10-C14Alcohols, laureth-1 to laureth-5, dimethyl lauramide/myristamide; PPG-2 hydroxyethyl cocamide, cocamide DIPA, lauramide DIPA, soyamide DIPA; and
water, wherein the weight ratio of water to organic solvent vehicle is from 4:1 to 1: 4.
6. The liquid composition according to claim 1 or 2, wherein the liquid thickener composition further comprises:
20% to 80% of a polyalkoxylated polyol polyester of formula-2 wherein Q is the group of sorbitol, trehalose, mannitol, dipentaerythritol, sucrose, lactose, chitobiose, cellobiose, and maltose;
the organic carrier, or a mixture thereof, selected from the group consisting of: alkyl polyglucosides, alkyl methyl glucamides, sorbitan laurate, sorbitan caprylate/caprate, liquid nonionic alkanolamide surfactants, laureth-1, laureth-2, laureth-3, glyceryl caprylate/caprate and glyceryl laurate; and
water, wherein the weight ratio of water to organic solvent vehicle is from 4:1 to 1: 4.
7. The liquid thickener composition according to claim 1 or 2, wherein the liquid thickener composition further comprises:
20% to 80% of a polyalkoxylated polyol polyester of formula-2 wherein Q is the group of sorbitol, trehalose, mannitol, dipentaerythritol, sucrose, lactose, chitobiose, cellobiose, and maltose;
the organic carrier or a mixture thereof selected from the group consisting of alkanolamides; and
water, wherein the weight ratio of water to organic solvent vehicle is from 4:1 to 1: 4.
8. A cosmetic, dermatological or pharmaceutical composition in the form of a hair cleansing/treatment formulation, skin and body cleansing/treatment formulation and other rinse formulations comprising the liquid thickener composition according to any of the preceding claims.
9. A cosmetic, dermatological or pharmaceutical composition comprising a liquid thickener composition according to claim 5 in the form of a hair cleansing/treatment formulation, a skin and body cleansing/treatment formulation and other rinse formulations.
10. The cosmetic, dermatological or pharmaceutical composition according to claim 8, further comprising water, and
1-50% by weight of a surfactant selected from the group consisting of: anionic surfactants, cationic surfactants, nonionic surfactants, amphoteric surfactants, and mixtures thereof;
from 0.1% to 15% of a liquid thickener composition of formula-2; and
0.1% to 60% of other ingredients selected from the group consisting of: skin and hair actives, stabilizers, other thickeners, and other conventional personal cleansing ingredients.
11. The cosmetic, dermatological or pharmaceutical composition of claim 9, further comprising
Water, and
1-50% by weight of a surfactant selected from the group consisting of: anionic surfactants, cationic surfactants, nonionic surfactants, amphoteric surfactants, and mixtures thereof;
from 0.1% to 15% of a liquid thickener composition of formula-1; and
0.1% to 60% of other ingredients selected from the group consisting of: skin and hair actives, stabilizers, other thickeners, and other conventional personal cleansing ingredients.
12. A cosmetic, dermatological or pharmaceutical composition of about 1% to 8% of the liquid thickener composition according to any of claims 1 to 7, further comprising:
from about 1% to 25% by weight of skin and hair active ingredients selected from the group consisting of: UV filters, moisturizers, conditioners, preservatives, deodorant actives, reducing agents for permanent products, colorants for hair coloring, anti-aging actives, fragrances, petrolatum, vegetable oils, cationic conditioning polymers, and mixtures thereof; and
and (3) water.
13. The composition of claim 1 or 2, wherein the guerbet acid moiety has from 16 to 32 carbons.
14. The composition of claim 1 or 2, wherein the guerbet acid moiety has from 18 to 24 carbons.
15. The composition of claim 1 or 2, wherein the guerbet acid moiety has 20 carbons.
CN201910248814.XA 2019-03-29 2019-03-29 Liquid thickener composition comprising polyalkoxylated polyol polyester having Guerbet acid moieties Pending CN111821216A (en)

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CN1323196A (en) * 1998-10-10 2001-11-21 考格尼斯德国有限责任公司 Cosmetic preparations
US20180071198A1 (en) * 2016-09-14 2018-03-15 Applechem Inc. Liquid thickener composition comprising polyalkoxylated polyols polyester for personal care, dermatological, and pharmaceutical preparations
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