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JP-2026076291-A - Fibrous amino acid-based substrates, particularly nonionic high molecular weight fatty acid compounds for hair treatment.

JP2026076291AJP 2026076291 AJP2026076291 AJP 2026076291AJP-2026076291-A

Abstract

[Problem] To provide a hair care formulation that can be synthesized in a simple, cost-effective, and flexible manner, mainly based on sustainable raw materials, is easy to formulate and use, and is useful for conditioning hair and improving combability, smoothness, and a pleasant finish for both dry and wet hair. [Solution] The present invention provides a hair care formulation comprising at least one nonionic compound comprising at least one terminal estolide moiety, a nonionic compound comprising at least one terminal estolide moiety, the use of a nonionic compound comprising at least one terminal estolide moiety in a cosmetic formulation for skin and/or hair care, the use of a nonionic compound comprising at least one terminal estolide moiety for fiber treatment, and a composition comprising at least one such compound for hair treatment. [Selection Diagram] None

Inventors

  • ワグナー，ロランド
  • ストレイヒャー，カタリーナ
  • ローマン，ラウラ
  • ヴェンスケ，クリスチアン
  • ハヴェリ，シュルティサガル，ダッタトラヤ

Assignees

  • モメンティブ パフォーマンス マテリアルズ ゲーエムベーハー

Dates

Publication Date
20260511
Application Date
20260206
Priority Date
20191217

Claims (20)

  1. A hair care formulation comprising at least one compound of formula (I), R 1 (-X-C(O)-F) p (I) Here, R1 in formula (I) is selected from p-valent, optionally substituted hydrocarbon radicals, optionally -O-, -NH-, -C(O)-, -C(S)-, tertiary amino group, and may comprise one or more groups selected from quaternary ammonium groups, and may optionally be substituted with one or more groups selected from carboxyl groups or hydroxyl groups. p ≥ 2, more preferably 2 - 8¹¹, X may be the same or different, and is selected from -O- or -NR10- , where R10 is hydrogen, or optionally -O-, -NH-, -C(O)-, -C(S)-, or a tertiary amino group having up to 100 carbon atoms. Selected from the group consisting of linear, cyclic, or branched saturated, unsaturated, or aromatic hydrocarbon radicals that are optionally substituted with one or more groups selected from the group, Alternatively, in formula (I), R 10 can form a bond to R 1 to form a ring structure. F may be the same or different, and may have a maximum of 1005 carbon atoms, and may optionally be -O-, -NH-, -C(O)-, -C(S)-, and a tertiary amino group. Selected from optionally substituted linear, cyclic, or branched saturated, unsaturated, or aromatic hydrocarbon radicals, comprising one or more groups selected from and optionally substituted with one or more selected from carboxyl groups, hydroxyl groups, or halide groups, However, this is conditional on at least one radical F containing at least one part of formula (II) or formula (II*), -R 6 (-X-C(O)-R 6 ) m -X-C(O)-R 7 (II) -R 6 (-X-C(O)-R 6 ) m -X-C(O)-R 7* (II*) Here, X is as defined above, m = 0 to 20, preferably 1 to 20. R6 is independently selected from divalent, optionally substituted linear, cyclic, or branched saturated or unsaturated hydrocarbon radicals having up to 36 carbon atoms. R7 has 1 to 1000 carbon atoms and can optionally be -O-, -NH-, -C(O)-, -C(S)-, or a tertiary amino group. Quaternary ammonium group A linear, cyclic, or branched saturated or unsaturated hydrocarbon radical, independently selected from optionally substituted linear, cyclic, or branched, saturated or unsaturated hydrocarbon radicals, comprising one or more groups selected from and which may be substituted with a carboxyl group, a hydroxyl group, or a halide group, wherein the radical R7 cannot contain an internal carboxyl group or amide group; that is, R7 cannot contain a combination of a -C(O)- group and an -O- group, or a combination of a -C(O)- group and an -NH- or tertiary amino group. However, in at least one part of formula (II), R7 has at least two, preferably at least six, carbon atoms, and in the same part of formula (II), at least one R6 has at least six, preferably at least eight carbon atoms. R7 * has 1 to 1000 carbon atoms and can optionally be -O-, -NH-, -C(O)-, -C(S)-, or a tertiary amino group. Quaternary ammonium group A branched or dendrimer hydrocarbon radical, independently selected from optionally substituted, comprising one or more groups selected from and which may be substituted with a carboxyl group, a hydroxyl group, or a halide group, where the radical R 7* is terminated with two or more groups of the general structure described below. -X-C(O)-T Here, X is as defined above, and T is a monovalent linear, cyclic, or branched saturated or unsaturated hydrocarbon radical having up to 36 carbon atoms and optionally substituted with a carboxyl group, a hydroxyl group, or a halide group. However, in at least one part of formula (II*), R7 * is terminated by one or more groups T having at least two, preferably at least six, carbon atoms, and in the same part of formula (II*), at least one R6 has at least six, preferably at least eight carbon atoms. or, A compound comprising at least one compound of general formula (IV), R 1 (-C(O)-X-G) q (IV) Here, X is as defined above, R1 in formula (IV) preferably has up to 1000 carbon atoms and optionally -O-, -NH-, -C(O)-, -C(S)-, tertiary amino group, Selected from q-valent, optionally substituted hydrocarbon radicals, which may comprise one or more groups selected from quaternary ammonium groups and may optionally be substituted with one or more groups selected from carboxyl groups or hydroxyl groups. q = 2 to 55, preferably 2 to 40, more preferably 2 to 4, and G may be the same or different, having a maximum of 1005 carbon atoms, and optionally -O-, -NH-, -C(O)-, -C(S)-, and tertiary amino groups Selected from optionally substituted linear, cyclic, or branched saturated, unsaturated, or aromatic hydrocarbon radicals, comprising one or more groups selected from and substituted with one or more selected from carboxyl groups, hydroxyl groups, or halide groups, However, this is conditional on at least one radical G containing at least one part of formula (V), -R 6 (-C(O)-X-R 6 ) m -C(O)-X-R 11 (V) Here, X is as defined above, m = 0 to 20, preferably 1 to 20. R 6 in equation (V) is as defined above for equation (I), R11 has 1 to 1000 carbon atoms and can optionally have -O-, -NH-, -C(O)-, -C(S)-, or a tertiary amino group. Quaternary ammonium group A linear, cyclic, or branched saturated or unsaturated hydrocarbon radical, independently selected from optionally substituted linear, cyclic, or branched, saturated or unsaturated hydrocarbon radicals, comprising one or more groups selected from and which may be substituted with a carboxyl group, a hydroxyl group, or a halide group, wherein the radical R11 cannot contain an internal carboxyl group or amide; that is, R11 cannot contain a combination of a -C(O)- group and an -O- group, or a combination of a -C(O)- group and an -NH- or tertiary amino group. However, in at least one part of formula (V), R11 has at least two, preferably at least six, carbon atoms, and in the same part of formula (V), at least one R6 has at least six, preferably at least eight carbon atoms. However, the compound of formula (I) does not consist solely of glycerol and ricinoleic acid moieties, i.e., polyglycerol polyricinolate (PGPR). Hair care ingredients.
  2. The hair care formulation according to claim 1, wherein in a compound of formula (I) or (IV), R1 is as defined above, having up to 10,000 carbon atoms, preferably up to 1,000, more preferably up to 300, even more preferably up to 100, and most preferably up to 50 carbon atoms.
  3. The hair care formulation according to claim 1 or 2, wherein in a compound of formula (I) or (IV), the number of carbon atoms in any R7 or R11 of the compound is from 3 to 300, preferably from 3 to 100, more preferably from 3 to 50, even more preferably from 3 to 36, even more preferably from 3 to 24, and most preferably from 11 to 24.
  4. The hair care formulation according to any one of claims 1 to 3, wherein the compound of formula (I) or (IV) has a molecular weight in the range of 1,500 to 200,000 g/mol, preferably 1,500 to 100,000 g/mol, more preferably 1,500 to 30,000 g/mol, even more preferably 1,500 to 1,000 g/mol, even more preferably 1,500 to 5,000 g/mol, and most preferably 1,500 to 3,000 g/mol.
  5. The hair care formulation according to any one of claims 1 to 4, wherein the compound of formula (I) comprises a portion of formula (II) from 2 to 100, more preferably a portion of formula (II) from 2 to 50, even more preferably 2 to 20, even more preferably 2 to 10, even more preferably 2 to 6, and most preferably 2 to 4 of formula (II); or, wherein the compound of formula (IV) comprises a portion of formula (V) from 2 to 100, more preferably a portion of formula (V) from 2 to 50, even more preferably 2 to 20, even more preferably 2 to 10, even more preferably 2 to 6, and most preferably 2 to 4 of formula (V); or, wherein the compound of formula (I) comprises a portion of formula (II*) from 2 to 100, more preferably a portion of formula (II*) from 2 to 50, even more preferably 2 to 20, even more preferably 2 to 10, even more preferably 2 to 6, and most preferably 2 to 4 of formula (II*).
  6. At least one compound of general formula (I) is represented by general formula (III), {[(F-C(O)-X-) 1-5 R 3 (-X-C(O)-)] 1-3 R 4 -C(O)-X-} r -R 2 (-X-C(O)-F) s (III) Here, X is as defined above, R² in formula (III) has up to 1000 carbon atoms and can optionally be -O-, -NH-, -C(O)-, -C(S)-, or a tertiary amino group. and may comprise one or more groups selected from quaternary ammonium groups, and optionally substituted with one or more carboxyl or hydroxyl groups, selected from (r+s) valence, optionally substituted hydrocarbon radicals, and optionally forming a bond to the nitrogen atom of the group -NR10- when R10 is bonded to R2 , R3 has up to 1000 carbon atoms and can optionally consist of -O-, -NH-, -C(O)-, -C(S)-, and tertiary amino groups. Selected from optionally substituted, divalent to hexavalent hydrocarbon radicals, which may contain one or more groups selected from: If multiple R3s exist in equation (III), they may be the same or different. R4 has up to 300 carbon atoms and can optionally consist of -O-, -NH-, -C(O)-, -C(S)-, and tertiary amino groups. Selected from linear, cyclic, or branched saturated, unsaturated, or aromatic hydrocarbon radicals, which are optionally substituted with divalent to tetravalent groups and include one or more groups selected from the following: If multiple R4s exist in equation (III), they may be the same or different. And here, from r + s = 2, we get 55. r = 0 to 54, s ≥ 1, and in equation (III), F is as defined above, provided that at least one of the radicals F contains at least one part of equation (II) or equation (II*), -R 6 (-X-C(O)-R 6 ) m -X-C(O)-R 7 (II) -R 6 (-X-C(O)-R 6 ) m -X-C(O)-R 7* (II*) Here, X, R6 , R7 , and R7 * are as defined in the previous section. m = 0 to 20, preferably 1 to 20. The hair care formulation according to any one of claims 1 to 5 , provided that in at least one part of formula (II), R7 has at least two, preferably at least six carbon atoms, and in the same part of formula (II), at least one R6 has at least six, preferably at least eight carbon atoms, or in at least one part of formula (II*), R7 * is terminated by one or more groups T having at least two, preferably at least six carbon atoms, and in the same part of formula (II*), at least one R6 has at least six, preferably at least eight carbon atoms.
  7. R1 in the compound of formula (IV) or R2 in the compound of formula (III) has 2 to 300 carbon atoms, more preferably 3 to 200 carbon atoms, even more preferably 3 to 150 carbon atoms, specifically 3 to 50 carbon atoms, and more specifically 3 to 20 carbon atoms, and optionally -O-, -NH-, -C(O)-, -C(S)-, and tertiary amino groups. A hair care formulation according to any one of claims 1 to 6, which may comprise one or more groups selected from and optionally substituted with a carboxyl group or a hydroxyl group.
  8. In the compound of formula (III), The hair care formulation according to claims 6 and 7, wherein R3 is selected from a divalent to tetravalent residue, specifically a divalent residue, a trivalent residue, or a tetravalent residue.
  9. In the compound of formula (III), R3 has a maximum of 300 carbon atoms, more preferably 3 to 200 carbon atoms, even more preferably 3 to 150 carbon atoms, specifically 3 to 50 carbon atoms, and more specifically 3 to 20 carbon atoms, and optionally -O-, -NH-, -C(O)-, -C(S)-, and tertiary amino groups. A hair care formulation according to claims 6 to 8, selected from optionally substituted hydrocarbon radicals, which may include one or more groups selected from the above.
  10. In compounds of formula (I), (III), or (IV), F and G have up to 200 carbon atoms, preferably 10 to 200 carbon atoms, more preferably 10 to 150, and even more preferably 10 to 100 carbon atoms, and optionally -O-, -NH-, -C(O)-, -C(S)-, and tertiary amino groups. A hair care formulation according to any of the preceding claims, comprising one or more groups selected from and optionally substituted with one or more carboxyl groups, hydroxyl groups or halogenated groups, selected from optionally substituted linear, cyclic or branched, saturated, unsaturated or aromatic hydrocarbon radicals.
  11. In the compound of formula (III), R4 has 2 to 300 carbon atoms, preferably 5 to 200 carbon atoms, more preferably 8 to 150 carbon atoms, and even more preferably 10 to 120 carbon atoms, and optionally -O-, -NH-, -C(O)-, -C(S)-, and tertiary amino groups. A hair care formulation according to claims 6 to 10, selected from linear, cyclic, or branched saturated, unsaturated, or aromatic hydrocarbon radicals that are optionally substituted with divalent to tetravalent, preferably divalent, trivalent, or tetravalent groups, comprising one or more groups selected from the above.
  12. In the compound of formula (III), The hair care formulation according to claims 6 to 11, wherein r = 0 to 50 or 1 to 50, preferably 0 to 20, more preferably 0 to 10, even more preferably 1 to 10, specifically 1 to 5, more specifically 0, 1, 2, 3, 4, 5, and even more specifically 2.
  13. In a compound of formula (I) or (III), At least one of the radicals F is a partial -R 6 (-O-C(O)-R 6 ) m -O-C(O)-R 7 , -R 6 (-NR 10 -C(O)-R 6 ) m -O-C(O)-R 7 , -R 6 (-NR 10 -C(O)-R 6 ) m -NR 10 -C(O)-R 7 , Preferably, -R 6 (-O-C(O)-R 6 ) m -O-C(O)-R 7 , where R 10 , R 6 , R 7 , and m are as defined above. It includes at least one part selected from, Alternatively, in the compound of formula (I) or (III), At least one of the radicals F is a partial -R 6 (-O-C(O)-R 6 ) m -O-C(O)-R 7* , -R 6 (-NR 10 -C(O)-R 6 ) m -O-C(O)-R 7* , -R 6 (-NR 10 -C(O)-R 6 ) m -NR 10 -C(O)-R 7* , Preferably, -R 6 (-O-C(O)-R 6 ) m -O-C(O)-R 7* , where R 10 , R 6 , R 7* , and m are as defined above. A hair care formulation according to any of the preceding claims, comprising at least one portion selected from the above.
  14. In the compound of formula (IV), At least one of the radicals G is a partial -R 6 (-C(O)-O-R 6 ) m -C(O)-O-R 11 , -R 6 (-C(O)-NR 10 -R 6 ) m -C(O)-O-R 11 , -R 6 (-C(O)-NR 10 -R 6 ) m -C(O)-NR 10 -R 11 , Preferably, -R 6 (-C(O)-O-R 6 ) m -C(O)-O-R 11 , where R 10 , R 6 , R 11 , and m are as defined above. A hair care formulation according to any one of claims 1 to 5, 7, and 10, comprising at least one of the following.
  15. In the compound (II), (V), or (II*) of the compound (I), (III), or (IV), A hair care formulation according to any of the above claims, wherein m = 0 to 10, more preferably 0 to 6, even more preferably 1 to 6, specifically 0, 1, 2, 3, 4, 5, 6, more specifically 0 or 1.
  16. In compounds of formula (I), (III), or (IV), R 10 is selected from the group consisting of hydrogen, n-, iso-, or tert.- C1 - C22 -alkyl, C2 - C22 -alkoxyalkyl, C5 - C30 -cycloalkyl, C6 - C30 -aryl, C6 - C30 -aryl( C1 - C6 )alkyl, C6 - C30 -alkylaryl, C2 - C22 -alkenyl, and C2 - C22 -alkenyloxyalkyl, which may optionally be substituted with hydroxyl and halogen, respectively, and may optionally contain one or more ether groups (-O-), and preferably R 10 is selected from hydrogen or n-, iso-, and tert.- C1 - C22 -alkyl, as described in any of the above claims.
  17. In compounds of formula (I), (III), or (IV), R6 is independently selected from optionally substituted linear, cyclic, or branched saturated or unsaturated radicals having up to 24 carbon atoms, preferably 1 to 24, more preferably 2 to 20, and even more preferably 8 to 18 carbon atoms, according to any of the above claims, as a hair care formulation.
  18. In a compound of formula (I) or (III), R7 is independently selected from optionally substituted linear, cyclic or branched, saturated or unsaturated hydrocarbon radicals, as described in any of claims 1 to 13 and 15 to 17, wherein R7 has up to 24 carbon atoms, preferably 1 to 24, more preferably 2 to 20, and even more preferably 8 to 18 carbon atoms, and may optionally be substituted with one or more groups selected from carboxyl groups, hydroxyl groups, or halide groups.
  19. In the compound of formula (IV), R11 is independently selected from optionally substituted linear, cyclic, or branched saturated or unsaturated hydrocarbon radicals having up to 24 carbon atoms, preferably 1 to 24, more preferably 2 to 20, and even more preferably 8 to 18 carbon atoms, according to any one of claims 1 to 5, 7, 10, and 14 to 17.
  20. In a compound of formula (I) or (III), The total number of carbon atoms in R6 + R7 (Σ carbon atoms R6 , R7 ) in each single part of general formula (II) consisting of R6 and R7 is 10 to 300, preferably 15 to 200, more preferably 20 to 150, and even more preferably 30 to 100. Alternatively, in the compound of formula (I) or (III), The total number of carbon atoms in R6 + R7 * in each single part of the general formula (II*) composed of R6 and R7 * (Σ carbon atoms R6 , R7 * ) is 10 to 300, preferably 15 to 200, more preferably 20 to 150, and even more preferably 30 to 100. A hair care formulation according to any one of the above-mentioned claims 1 to 13 and 15 to 18.

Description

This invention relates to nonionic polymer fatty acid compounds, the use of nonionic polymer fatty acid compounds, aqueous compositions containing the same, cosmetic compositions containing the same, particularly hair care compositions, and their use for hair treatment. Hair can generally be straight, wavy, curly, twisted, or kinky. Human hair consists of three main morphological elements: the cuticle (the outermost thin shell of several concentric layers), the cortex (the body of the hair), and, in the case of larger diameter hair, the medulla (a thin central nucleus). The cuticle and cortex give rise to the mechanical properties of the hair, namely its tendency to be wavy, curly, or twisted. Straight hair may resemble a rod with a circular cross-section, wavy hair may appear compressed into an oval cross-section, curly hair may appear even more compressed into an elongated oval cross-section, and the cross-section of twisted hair may be even flatter. The main component of hair is the cross-linked alpha-helix protein keratin. Keratin is an intermediate filament protein specifically found in epithelial cells, such as human skin and hair, wool, feathers, and nails. Alpha-helix type I and type II keratin intermediate filament proteins (KIFs), with molecular weights of approximately 45–60 kDa, are embedded in an amorphous matrix of keratin-related proteins (KAPs), with molecular weights of 20–30 kDa (M.A. Rogers, L. Langbein, S. Praetzel-Wunder, H. Winter, J. Schweizer, J. Int Rev Cytol. 2006; 251:209-6); both intramolecular and intermolecular disulfide bonds provided by cystine contribute to the cytoskeletal protein network that maintains the cytoskeleton. In addition to disulfide crosslinks, ionic bonds or salt bridges pairing various amino acids found in hair proteins contribute to the outward shape of the hair. It is known in the art that hair can be treated with functionalized silicones and hydrocarbons that provide one or more cosmetic benefits, such as conditioning, shine, UV protection, and color retention. Typically, these silicone and hydrocarbon-based derivatives physically deposit on the fiber surface (cuticle) and thus contribute to the appearance of the hair, namely its smoothness, silky feel, friction resistance, alignment, and combability. Advanced silicone derivatives are generally considered high-performance materials with respect to attributes such as a smooth, silky hair feel, reduced friction, easy combability, and protection of hair color. Classified silicones are described in the prior art disclosures, namely US4891166, EP282720, US2008027202, US6730766, US6240929, WO02/10257, WO02/10259, WO2004/069137, WO2013/148629, WO2013/148635, and WO2013/148935. Typical hydrocarbon-based monoquaternary ammonium compounds include saturated or unsaturated fatty acid-based monofatty acid esters and difatty acid ester quats, as well as fatty amide quats having 10 to 24 carbon atoms in the alkyl chain. Details of these materials containing quaternary ammonium groups are disclosed, for example, in US2009/0000638, WO2012/027369, US2013/259820 and US5880086, US6465419, US6462014, US6323167, US6037315, US5854201, US5750490, US5463094, and US2003/013627. Certain monoquats containing polymerized fatty acids as hydrophobic tails are proposed for personal care applications in WO2004/093834. Nonionic ester derivatives containing polymerized fatty acids have been proposed as lubricants (US2011/0282084). C3 to C20 alcohol esters of high molecular weight fatty acids have been proposed as conditioning agents (WO2016/174256). WO2013/009471 describes C1 to C40 alcohol esters of high molecular weight fatty acids for the same application. Esters of Guerbet alcohols containing ricinoleic acid improve skin radiance (US 5786389). Polyesters of Guerbet alcohols containing dimer acids and dimer alcohols are proposed for the same application (US 7259226). Polyesters of polyalkylene oxides with dimer acids and monofunctional acids are skin conditioners (US 6800275). Esterified monomers and polymeric castor oil derivatives are also known and have been proposed as lubricants (US 2049072; A. Erdem-Senatalar et. al., J. Am. Oil Chem.Soc. 1994, 71(9), 1035-1037; A.T. Erciyes et. al., J. Am. Oil Chem.Soc. 1991, 68(9), 639-641; K.D. Pathak, J. Scientific & Industrial Res. 1955, 14B, 637-639). EP665286 describes the estolide portion containing triglycerides as a lubricant and thickener. Partial transesterification of high molecular weight fatty acids with plant-based oils yields products useful as emollients and moisturizers (FR2858616). Esterilization of castor oil with succinic acid or dimer acid and monofunctional C6 to C34 acids yields polyesters that give a glossy finish to the skin (US6787129, US6670441). There is a need for a fibrous amino acid-based substrate, particularly an efficient compound for hair treatment, that can be synthesized in a simple, cost-effective, and flexible manner, primarily based on sustainable raw mater