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WO2024249229A1 - Mélange de polyglycosides d'alkyle - Google Patents

Mélange de polyglycosides d'alkyle Download PDF

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Publication number
WO2024249229A1
WO2024249229A1 PCT/US2024/030679 US2024030679W WO2024249229A1 WO 2024249229 A1 WO2024249229 A1 WO 2024249229A1 US 2024030679 W US2024030679 W US 2024030679W WO 2024249229 A1 WO2024249229 A1 WO 2024249229A1
Authority
WO
WIPO (PCT)
Prior art keywords
alkyl
mixture
alkyl polyglycosides
formula
linear
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
PCT/US2024/030679
Other languages
English (en)
Inventor
Daniel S. Miller
Janet MCMILLAN
Robert Kennedy
Matthew M. Yonkey
Yujing TAN
Jianbo Hou
Zachary ROLFS
Tanner MCDANIEL
Timothy J. Young
Yuanqiao Rao
Thomas Peterson
Sally DREISBACH
Dan YE
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Dow Global Technologies LLC
Rohm and Haas Co
Original Assignee
Dow Global Technologies LLC
Rohm and Haas Co
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Dow Global Technologies LLC, Rohm and Haas Co filed Critical Dow Global Technologies LLC
Priority to CN202480034009.6A priority Critical patent/CN121175322A/zh
Publication of WO2024249229A1 publication Critical patent/WO2024249229A1/fr
Anticipated expiration legal-status Critical
Pending legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
    • C07H15/02—Acyclic radicals, not substituted by cyclic structures
    • C07H15/04—Acyclic radicals, not substituted by cyclic structures attached to an oxygen atom of the saccharide radical
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/66—Non-ionic compounds
    • C11D1/662—Carbohydrates or derivatives

Definitions

  • the present invention relates to a mixture of alkyl polyglycosides.
  • the invention relates to a mixture of alkyl polyglycosides, comprising: a linear alkyl polyglucoside of formula A R 1 -O-(G)nH (A) wherein R 1 is a linear C 6-15 alkyl group; wherein n is an average of 1 to 5; wherein G is a monosaccharide of glucose and a branched alkyl polysaccharide of formula B wherein R 2 is a linear or alkyl group; wherein g is 1 to 5; wherein S is a monosaccharide with 5 or 6 carbon atoms; with the proviso that the mixture of alkyl polyglycosides comprises ⁇ 15 wt%, based on weight of the mixture of alkyl polyglycosides, of a
  • R 6 is –(CH2)mCH(CH3) with 4 to 6 carbon atoms; that the mixture of alkyl polyglycosides comprises ⁇ 3 wt%, based on weight of the mixture of alkyl polyglycosides, of a compound of formula VI wherein R 12 is -(CH 2 ) p CH 3 ; monosaccharide with 4 to 6 carbon atoms; wherein p is 1 to 4 and wherein f is 1.1 to 10.
  • Aqueous cleaning formulations for example, floor care formulations, hard surface cleaning formulations have a wide array of uses.
  • uses include cleaning hard surfaces such as floors, counters, walls, tables, and other things made of, for example, wood, stone, laminate, ceramic and plastic materials which need to be cleaned periodically of accumulated dirt, oil, grease, and other contaminants.
  • a proposed alternative has been sugar based surfactants.
  • sugar based surfactants have exhibited poor water solubility, especially in the presence of salts; and poor cleaning performance when used in single surfactant systems (e.g., without an anionic cosurfactant).
  • Recent efforts have sought to overcome the poor cleaning performance by exploring sugar based surfactants with branched hydrophobes.
  • the present invention provides a mixture of alkyl polyglycosides, comprising: a linear alkyl polyglucoside of formula A Attorney Docket No.
  • R 1 -O-(G) n H (A) wherein R 1 is a linear C 6-15 alkyl group; wherein n is an average of 1 to 5; wherein G is a monosaccharide of glucose; and a branched alkyl polysaccharide of formula B wherein R 2 is a linear or alkyl group; wherein g is an average a or carbon atoms; with the proviso that the mixture of alkyl polyglycosides comprises ⁇ 15 wt%, based on weight of the mixture of alkyl polyglycosides, of a compound of formula I (I) wherein R 4 is a linear or alkyl group; wherein G 1 is a monosaccharide with 4 to 6 carbon atoms and wherein x is 1.1 to 4; with the proviso that R 1 is a linear C9-15 alkyl group in at least some of the linear alkyl polyglucoside of formula A; with the proviso that when
  • R 16 is a branched C 9-11 alkyl group; wherein G 2 is a glucose unit and wherein y is 1.4 to 2.0; with the proviso that the mixture of alkyl polyglycosides comprises 0 to 35 wt%, based on weight of the mixture of alkyl polyglycosides, of a compound of formula III wherein R 6 is –(CH2)mCH(CH3) with 4 to 6 carbon atoms; z m that the mixture of alkyl polyglycosides comprises ⁇ 3 wt%, based on weight of the mixture of alkyl polyglycosides, of a compound of formula VI wherein R 12 is -(CH2)pCH3; monosaccharide with 4 to 6 carbon atoms; wherein p is 1 to 4 and wherein f is 1.1 to 10.
  • the present invention provides an aqueous cleaning composition comprising water and a mixture of alkyl polyglycosides of the present invention.
  • the present invention provides a method of cleaning a hard surface, comprising: providing a soiled hard surface; wetting the soiled hard surface with an aqueous cleaning composition of the present invention; and wiping the wetted soiled hard surface to provide a cleaned hard surface.
  • water soluble as used herein and in the appended claims with respect to a given concentration of a mixture of alkyl polyglycosides in water, means that a solution of the given concentration of the mixture of alkyl polyglycosides in water will have a turbidity of ⁇ 15 Nephelometric Turbidity Units (NTU) measured at 20 °C using a turbidity meter.
  • NTU Nephelometric Turbidity Units
  • the mixture of alkyl polyglycosides of the present invention comprises: a linear alkyl polyglucoside of formula A (preferably, 50 to 95 wt%; more preferably, 60 to 95 wt%; still more preferably, 65 to 92.5 wt%; most preferably, 67 to 90 wt%), based on weight of the mixture of alkyl polyglycosides, of the linear alkyl polyglucoside of formula A) R 1 -O-(G)nH (A) wherein R 1 is a linear C 6-15 alkyl group (preferably, a linear C 8-14 alkyl group; more preferably, a linear C8-10 alkyl group; still more preferably, at least one of a linear C8 alkyl group and a linear C 10 alkyl group; most preferably, a mixture of a linear C 8 alkyl group and a linear C10 alkyl group); wherein n is an average of 1 to 5 (preferably, 1 to 3; more
  • R 2 is a linear or branched C 2-7 alkyl group; wherein R 3 is a linear or branched C 4-7 alkyl group; wherein g is an average of 1 to 5 (preferably, 1 to 3; more preferably, 1 to 2; most preferably, 1.1 to 2) and wherein S is a monosaccharide with 5 or 6 carbon atoms (preferably, ribulose, xylulose, ribose, arabinose, xylose, lyxose, galactose, mannose, glucose and mixtures thereof; more preferably, arabinose, xylose, glucose and mixtures thereof; still more preferably, xylose, glucose and mixtures thereof; most preferably, xylose); with the proviso that the mixture of alkyl polyglycosides comprises ⁇ 15 wt% (preferably, 1 to 13 wt%; more preferably, 1 to 12.5 wt%; still more preferably, 5 to
  • R 6 is –(CH 2 ) m CH(CH 3 ) with 4 to 6 carbon atoms; that the mixture of alkyl polyglycosides comprises ⁇ 3 wt% (preferably, ⁇ 0.5 wt%; more preferably, ⁇ 0.1 wt%; still more preferably, ⁇ 0.05 wt%; yet more preferably, ⁇ 0.01 wt%; still yet more preferably, ⁇ 0.001 wt%; yet still more preferably, ⁇ 0.0001 wt%; most preferably, less than detectable limit), based on weight of the mixture of alkyl polyglycosides, of a compound of formula VI wherein R 12 is -(CH2)pCH3; monosaccharide with 4 to 6 carbon atoms; wherein p is 1 to 4 and wherein f is 1.1 to 10.
  • the mixture of alkyl polyglycosides of the present invention comprises: 50 to 95 wt% (preferably, 60 to 95 wt%; more preferably, 65 to 92.5 wt%; most preferably, 67 to 90 wt%), based on weight of the mixture of alkyl polyglycosides, of a linear alkyl polyglucoside of formula A; wherein R 1 is a linear C6-15 alkyl group (preferably, a linear C8-14 alkyl group; more preferably, a linear C8-10 alkyl group; still more preferably, at least one of a linear C8 alkyl group and a linear C10 alkyl group; most preferably, a mixture of a linear C8 alkyl group and a linear C 10 alkyl group); wherein n is an average of 1 to 5 (preferably, 1 to 3; more preferably, 1 to 2; most preferably, 1.1 to 2); wherein G is a monosaccharide of glucose; and 5
  • the mixture of alkyl polyglycosides comprises ⁇ 15 wt% (preferably, 1 to 13 wt%; more preferably, 1 to 12.5 wt%; still more preferably, 5 to 12 wt%; yet more preferably, 7.5 to 11.5 wt%; still yet more preferably, 8 to 11 wt%; most preferably, 9 to 10.5 wt%), based on weight of the mixture of alkyl polyglycosides, of a compound of formula I (I) wherein R 4 is a linear or 1 alkyl group; wherein G is a to atoms x to 4; with the proviso that R 1 is a linear C9-15 alkyl group (preferably, a linear C9-14 alkyl group; more preferably, a linear C10-12 alkyl group;
  • R 10 is –(CH 2 ) c+1 CH 3 ; with 4 to 6 carbon atoms; that the linear alkyl polyglucoside of formula A and the branched alkyl polysaccharide of formula B comprise 95 to 100 wt% (preferably, 97 to 100 wt%; more preferably, 98 to 100 wt%; still more preferably, 99 to 100 wt%; yet more preferably, 99.5 to 100 wt%; still yet more preferably, 99.9 to 100 wt%; most preferably, 100 wt%) of the alkyl polyglycosides present in the mixture of alkyl polyglycosides; (iv) with the proviso that the mixture of alkyl polyglycosides comprises ⁇ 0.05 wt% (preferably, ⁇ 0.01; more preferably, ⁇ 0.005; still more preferably, ⁇ 0.001; yet more preferably, ⁇ 0.0005; still yet more preferably, ⁇
  • the mixture of alkyl polyglycosides of the present invention comprises 50 to 95 wt% (preferably, 60 to 95 wt%; more preferably, 65 to 92.5 wt%; most preferably, 67 to 90 wt%), based on weight of the mixture of alkyl polyglycosides, of a linear alkyl polyglucoside of formula A; wherein the linear alkyl polyglucoside of formula A is a blend comprising 5 to 95 wt% (preferably, 10 to 90 wt%; more preferably, 25 to 75 wt%; still more preferably, 40 to 60 wt%; most preferably, 45 to 55 wt%), based on weight of the blend, of a linear C8 alkyl polyglucoside and 5 to 95 wt% (preferably, 10 to 90 wt%; more preferably, 25 to 75 wt%; still more preferably, 40 to 60 wt%; most preferably, 45 to 55 wt%), based on weight of the blend,
  • the mixture of alkyl polyglycosides of the present invention comprises 5 to 50 wt% (preferably, 5 to 40 wt%; more preferably, 7.5 to 35 wt%; most preferably, 10 to 33 wt%), based on weight of the mixture of alkyl polyglycosides, of a branched alkyl polysaccharide of formula B; wherein R 2 is a linear or branched C2-7 alkyl group; wherein R 3 is a linear or branched C 4-7 alkyl group; wherein g is an average of 1 to 5 (preferably, 1 to 3; more preferably, 1 to 2; most preferably, 1.1 to 2); wherein S is a monosaccharide with 5 or 6 carbon atoms (preferably, ribulose, xylulose, ribose, arabinose, xylose, lyxose, galactose, mannose, glucose and mixtures thereof; more preferably, arab
  • the mixture of alkyl polyglycosides of the present invention comprises 5 to 50 wt% (preferably, 5 to 40 wt%; more preferably, 7.5 to 35 wt%; most preferably, 10 to 33 wt%), based on weight of the mixture of alkyl polyglycosides, of a branched alkyl polysaccharide of formula B; wherein R 2 is a linear or branched C 2-7 alkyl group; wherein R 3 is a linear or branched C4-7 alkyl group; wherein g is an average of 1 to 5 (preferably, 1 to 3; more preferably, 1 to 2; most preferably, 1.1 to 2); wherein S is a monosaccharide with 5 or 6 carbon atoms (preferably, ribulose, xylulose, ribose, arabinose, xylose, lyxose, galactose, mannose, glucose and mixtures thereof; more preferably, arabinose,
  • R 3 is a linear or branched C 4-7 alkyl group; wherein g is an average of 1 to 5 (preferably, 1 to 3; more preferably, 1 to 2; most preferably, 1.1 to 2); wherein S is a monosaccharide with 5 or 6 carbon atoms (preferably, ribulose, xylulose, ribose, arabinose, xylose, lyxose, galactose, mannose, glucose and mixtures thereof; more preferably, arabinose, xylose, glucose and mixtures thereof; still more preferably, xylose, glucose and mixtures thereof; most preferably, xylose); and wherein the branched alkyl polysaccharide of formula B comprises > 90 wt% (preferably, 92 to 100 wt%; more preferably, 95 to 100 wt%; still more preferably, 98 to 100 wt%; most preferably, 99 to 100 wt%),
  • the aqueous cleaning composition of the present invention further comprises an additive.
  • the aqueous cleaning composition of the present invention optionally further comprises a cleaning surfactant other than the mixture of alkyl polyglycosides of the present invention; wherein the cleaning surfactant is selected from the group consisting of nonionic surfactants other than the mixture of alkyl polyglycosides, anionic surfactants, cationic surfactants, zwitterionic surfactants, amphoteric surfactants and mixtures thereof.
  • the aqueous cleaning composition of the present invention comprises 0.01 to 35 wt% (preferably, 0.1 to 20 wt%; more preferably, 1 to 15 wt%; most preferably, 5 to 12 wt%), based on the weight of the aqueous cleaning composition, of a cleaning surfactant other than the mixture of alkyl polyglycosides of the present invention; wherein the cleaning surfactant is selected from the group consisting of nonionic surfactants other than the mixture of alkyl polyglycosides, anionic surfactants, cationic surfactants, zwitterionic surfactants, amphoteric surfactants and mixtures thereof.
  • the anionic surfactant is selected from the group consisting of C8-20 alkyl benzene sulfonic acid, C8-20 alkyl benzene sulfates, C8-20 alkyl benzene sulfonate, C8-20 alkyl ether sulfonic acids, C8-20 alkyl ether sulfates, C8-20 alkyl ether sulfonates, paraffin sulfonic acid, paraffin sulfates, paraffin sulfonate, alpha-olefin sulfonic acid, alpha-olefin sulfate, alpha-olefin sulfonate, sulfonates of fatty acids, sulfonates of fatty acid esters, salts thereof and mixtures thereof.
  • the 85464-WO-PCT cleaning composition of the present invention optionally further comprises 0 to 10 wt% (preferably, 0.1 to 10 wt%; more preferably, 0.5 to 7.5 wt%; most preferably, 1 to 5 wt%), based on the weight of the aqueous cleaning composition, of an organic solvent; wherein the organic solvent is ethanol.
  • the aqueous cleaning composition of the present invention further comprises a dispersant polymer.

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  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Molecular Biology (AREA)
  • Health & Medical Sciences (AREA)
  • Biochemistry (AREA)
  • Wood Science & Technology (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Biotechnology (AREA)
  • General Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Detergent Compositions (AREA)
  • Saccharide Compounds (AREA)
  • Cosmetics (AREA)
  • Polysaccharides And Polysaccharide Derivatives (AREA)

Abstract

Mélange de polyglycosides d'alkyle comprenant : un polyglycoside d'alkyle linéaire de formule A R1-O-(G)nH, R1 étant un alkyle en C6-15 linéaire ; n étant compris entre 1 et 5 ; G étant du glucose ; R1 étant un alkyle en C9-15 dans au moins une partie de la formule A ; et un polysaccharide d'alkyle ramifié de la formule, R2 étant un alkyle en C2-7 ; R3 étant un alkyle en C4-7 ; g étant compris entre 1 et 5 ; S étant un monosaccharide ; le mélange comprenant < 15 % en poids de la formule, R4 étant un alkyle en C3-4 ; R5 étant un alkyle en C5-6 ; G1 étant un monosaccharide ; x étant compris entre 1,1 et 4 ; le mélange comprenant de 0 à 35 % en poids de la formule, R6 étant -(CH2)mCH(CH3)2 ; R7 étant -(CH2)m+2CH(CH3)2 ; G3 étant un monosaccharide ; z étant compris entre 1,1 et 4 ; m étant compris entre 0 et 3 ; le mélange comprenant< 3 % en poids de la formule, R12 étant -(CH2)pCH3 ; R13 étant -(CH2)p+1CH(CH3)2 ; G6 étant un monosaccharide ; p étant compris entre 1 et 4 et f étant compris entre 1,1 et 10 ; à la condition que la somme de carbones dans R2 + R3 est comprise entre 7 et 9, le mélange comprenant < 1 % en poids de la formule R16-O-(G2)y, R16 étant un un alkyle en C9-11 ramifié ; G2 étant un glucose ; y étant compris entre 1,4 et 2,0.
PCT/US2024/030679 2023-06-02 2024-05-23 Mélange de polyglycosides d'alkyle Pending WO2024249229A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN202480034009.6A CN121175322A (zh) 2023-06-02 2024-05-23 烷基聚糖苷的混合物

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US202363470462P 2023-06-02 2023-06-02
US63/470,462 2023-06-02

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Publication Number Publication Date
WO2024249229A1 true WO2024249229A1 (fr) 2024-12-05

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PCT/US2024/030678 Pending WO2024249228A1 (fr) 2023-06-02 2024-05-23 Mélange d'alkylpolyglycosides linéaires et ramifiés
PCT/US2024/030679 Pending WO2024249229A1 (fr) 2023-06-02 2024-05-23 Mélange de polyglycosides d'alkyle

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CN (1) CN121175322A (fr)
AR (1) AR132839A1 (fr)
WO (2) WO2024249228A1 (fr)

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20100083778A1 (en) 2008-10-06 2010-04-08 Dow Global Technologies Inc. Devices for retaining a nonporous substrate and methods
WO2014146958A1 (fr) * 2013-03-22 2014-09-25 Basf Se Mélanges d'alkylpolyglycosides, leur préparation et leurs utilisations
WO2015000792A1 (fr) * 2013-07-03 2015-01-08 Basf Se Mélanges de composés, leur préparation, et utilisations

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
RU2673078C2 (ru) * 2013-03-22 2018-11-22 Басф Се Алкилгликозиды в качестве поверхностно-активных веществ
ES2627753T3 (es) * 2014-09-17 2017-07-31 Basf Se Mezcla de alquilglicósidos, su fabricación y uso

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20100083778A1 (en) 2008-10-06 2010-04-08 Dow Global Technologies Inc. Devices for retaining a nonporous substrate and methods
WO2014146958A1 (fr) * 2013-03-22 2014-09-25 Basf Se Mélanges d'alkylpolyglycosides, leur préparation et leurs utilisations
WO2015000792A1 (fr) * 2013-07-03 2015-01-08 Basf Se Mélanges de composés, leur préparation, et utilisations

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Publication number Publication date
AR132839A1 (es) 2025-08-06
CN121175322A (zh) 2025-12-19
WO2024249228A1 (fr) 2024-12-05

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