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EP-4739653-A1 - COMPOSITIONS AND METHODS AND USES RELATED THERETO

EP4739653A1EP 4739653 A1EP4739653 A1EP 4739653A1EP-4739653-A1

Abstract

A method of preparing a taurate surfactant composition, the method comprising reacting a carboxylic acid of formula R 1 COOH or a reactive equivalent thereof with a compound of formula (I): (I) wherein X is hydrogen, a metal ion or an optionally substituted ammonium ion; R1 represents an optionally substituted C 3 -C 35 hydrocarbyl group; each of R 2 , R 3 , R 4 , R 5 and R 6 independently represents hydrogen or a C 1 -C 4 alkyl group; wherein the compound of formula (I) has a percentage renewable carbon index (RCI) of at least 50%.

Inventors

  • SWALLOW, Peter
  • GOUGH, TONY
  • MCROBBIE, IAN MALCOLM

Assignees

  • Innospec Limited

Dates

Publication Date
20260513
Application Date
20240703

Claims (20)

  1. 1 . A method of preparing a taurate surfactant composition, the method comprising reacting a carboxylic acid of formula R 1 COOH or a reactive equivalent thereof with a compound of formula (I): wherein X is hydrogen, a metal ion or an optionally substituted ammonium ion; R 1 represents an optionally substituted C3-C35 hydrocarbyl group; each of R 2 , R 3 , R 4 , R 5 and R 6 independently represents hydrogen or a C1-C4 alkyl group; wherein the compound of formula (I) has a percentage renewable carbon index (RCI) of at least 50%.
  2. 2. A method according to claim 1 wherein the compound of formula (I) has a percentage renewable carbon index (RCI) of 95 to 100%.
  3. 3. A method according to claim 1 or claim 2 wherein the carboxylic acid of formula R 1 COOH or a reactive equivalent thereof has a percentage renewable carbon index (RCI) of 95 to 100%.
  4. 4. A surfactant composition comprising one or more taurate compounds of formula (II): wherein X is hydrogen, a metal ion or an optionally substituted ammonium ion; R 1 represents an optionally substituted C3-C35 hydrocarbyl group; each of R 2 , R 3 , R 4 , R 5 and R 6 independently represents hydrogen or a C1-C4 alkyl group; wherein at least 50% of the carbon atoms provided by the moiety NR 6 CR 2 R 3 CR 4 R 5 SC>3X in the compound of formula (II) are from a renewable carbon source.
  5. 5. A compound of formula (II): wherein X is hydrogen, a metal ion or an optionally substituted ammonium ion; R 1 represents an optionally substituted C3-C35 hydrocarbyl group; each of R 2 , R 3 , R 4 , R 5 and R 6 independently represents hydrogen or a C1-C4 alkyl group; wherein at least 50% of the carbon atoms provided by the moiety NR 6 CR 2 R 3 CR 4 R 5 SC>3X in the compound of formula (II) are from a renewable carbon source.
  6. 6. A compound of formula (I): wherein X is hydrogen, a metal ion or an optionally substituted ammonium ion; each of R 2 , R 3 , R 4 , R 5 and R 6 independently represents hydrogen or a C1-C4 alkyl group and wherein at least one of R 2 , R 3 , R 4 , R 5 and R 6 is not hydrogen; wherein at least 50% of the carbon atoms in the compound are from a renewable carbon source
  7. 7. The use of a surfactant composition comprising one or more taurate compounds of formula (II): wherein X is hydrogen, a metal ion or an optionally substituted ammonium ion; R 1 represents an optionally substituted C3-C35 hydrocarbyl group; each of R 2 , R 3 , R 4 , R 5 and R 6 independently represents hydrogen or a C1-C4 alkyl group; wherein at least 50% of the carbon atoms provided by the moiety NR 6 CR 2 R 3 CR 4 R 5 SC>3X in the compound of formula (II) are from a renewable carbon source; in toilet care, automatic dishwashing, manual dishwashing, laundry, fabric care, kitchen care, carpet cleaning, air fresheners, vehicle care, polishing products, machine cleaning and maintenance, pesticides, insecticides, fungicides, herbicides, oilfield chemical applications, marine applications, personal care, institutional I industrial cleaning or emulsion polymerisation compositions.
  8. 8. A formulated composition comprising: a surfactant composition comprising one or more taurate compounds of formula (II): wherein X is hydrogen, a metal ion or an optionally substituted ammonium ion; R 1 represents an optionally substituted C3-C35 hydrocarbyl group; each of R 2 , R 3 , R 4 , R 5 and R 6 independently represents hydrogen or a C1-C4 alkyl group; wherein at least 50% of the carbon atoms provided by the moiety NR 6 CR 2 R 3 CR 4 R 5 SC>3X in the compound of formula (II) are from a renewable carbon source; and one or more further components.
  9. 9. A precursor concentrate composition comprising: a surfactant composition comprising one or more taurate compounds of formula (II): wherein X is hydrogen, a metal ion or an optionally substituted ammonium ion; R 1 represents an optionally substituted C3-C35 hydrocarbyl group; each of R 2 , R 3 , R 4 , R 5 and R 6 independently represents hydrogen or a C1-C4 alkyl group; wherein at least 50% of the carbon atoms provided by the moiety NR 6 CR 2 R 3 CR 4 R 5 SC>3X in the compound of formula (II) are from a renewable carbon source; and one or more further surfactants.
  10. 10. A surfactant composition, compound, use, formulated composition or precursor concentrate composition according to any of claims 4 to 9 wherein from 95 to 100% or 98 to 100% of the carbon atoms provided by the moiety NR 6 CR 2 R 3 CR 4 R 5 SC>3X in the compound of formula (II) are from a renewable carbon source.
  11. 11. A surfactant composition, compound, use, formulated composition or precursor concentrate composition according to any of claims 4 to 10 where the compound of formula (II) has a percentage renewable carbon index (%RCI) of from 95 to 100%, preferably from 99 to 100%.
  12. 12. A method, surfactant composition, compound, use, formulated composition or precursor concentrate composition according to any preceding claim wherein R 1 is provided by one or more naturally occurring fatty acids.
  13. 13. A method, surfactant composition, compound, use, formulated composition or precursor concentrate composition according to any preceding claim wherein R 1 is provided by one or more fatty acids selected from coco acid, hexanoic acid, caproic acid, caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, palmitoleic acid, stearic acid, oleic acid, linoleic acid, arachidic acid, gadoleic acid, arachidonic acid, eicosapentanoic acid, behenic acid, erucic acid, docosahexanoic lignoceric acid, naturally occurring fatty acids such as those obtained from coconut oil, tallow, palm kernel oil, butterfat, palm oil, olive oil, corn oil, linseed oil, peanut oil, fish oil and rapeseed oil.
  14. 14. A method, surfactant composition, compound, use, formulated composition or precursor concentrate composition according to any preceding claim wherein R 6 is Ci to C4 alkyl, preferably methyl.
  15. 15. A method, surfactant composition, compound, use, formulated composition or precursor concentrate composition according to any of claims 1 to 13 wherein R 6 is hydrogen.
  16. 16. A method, surfactant composition, compound, use, formulated composition or precursor concentrate composition according to any preceding claim wherein one of the groups R 2 , R 3 , R 4 and R 5 represents an optionally substituted C1-C4 alkyl group (preferably methyl) and the remaining groups represent hydrogen.
  17. 17. A method, surfactant composition, use, compound, formulated composition or precursor concentrate composition according to claim 16 which comprises a mixture of isomers comprising a compound of formula R 1 CONR 6 CH2CHR 4 SC>3X in which each of R 6 and R 4 represents a Ci- 04 alkyl group (preferably methyl) and a compound of formula R 1 CONR 6 CHR2CH2SO3X in which each of R 6 and R 2 represents a C1-C4 alkyl group (preferably methyl); preferably wherein in at least 90% of compounds R 2 is methyl and R 4 is hydrogen and at most 10% of compounds R 2 is hydrogen and R 4 is methyl.
  18. 18. A method, surfactant composition, compound, use, formulated composition or precursor concentrate composition according to any of claims 1 to 15 wherein each of R 2 , R 3 , R 4 and R 5 is hydrogen.
  19. 19. A formulated composition according to any of claims of 8 or 10 to 18 wherein the one or more further components are selected from chelating agents, preservatives, pH modifiers, hydrotropes and further surfactants.
  20. 20. A formulated composition according to claim 19 which comprises one or more further surfactants.

Description

Compositions and methods and uses related thereto The present invention relates to taurate surfactant compounds, compositions comprising such compounds and methods and uses relating thereto. Taurate compounds are common, versatile surfactants that can be used in a variety of applications. They are particularly useful in personal care applications due to their low irritancy potential, desirable foaming properties, high solubility and stability. However current commercial compositions comprising such surfactants are derived from petrochemical sources. Environmental concerns are becoming increasingly important to consumers with many seeking to purchase household and cosmetic products having a reduced environmental impact. Therefore it is highly desirable to provide surfactants that can be prepared from renewable carbon sources. In this specification when we refer to renewable carbon sources we mean to include all carbon sources that are not directly obtained from petrochemicals. However the term is intended to encompass recovered or recycled carbon that may originally have been obtained from such sources. Thus renewable carbon sources may include those classed as green (plant derived), blue (marine derived), purple (deriving from carbon capture) or grey (from plastics or pyrolysis of other material). According to the first aspect of the present invention there is provided a method of preparing a taurate surfactant composition, the method comprising reacting a carboxylic acid of formula R1COOH or a reactive equivalent thereof with a compound of formula (I): wherein X is hydrogen, a metal ion or an optionally substituted ammonium ion; R1 represents an optionally substituted C3-C35 hydrocarbyl group; and each of R2, R3, R4, R5 and R6 independently represents hydrogen or a C1-C4 alkyl group; and wherein the compound of formula (I) has a percentage renewable carbon index (RCI) of at least 50%. The method of the first aspect of the present invention relates to a method of preparing a taurate surfactant composition. The taurate composition provided may consist essentially of one or more taurate compounds or it may comprise one or more further components. The one or more further components may, for example, include by-products, residual starting materials, impurities or solvents. According to a second aspect of the present invention there is provided a surfactant composition comprising one or more taurate compounds of formula (II): wherein X is hydrogen, a metal ion or an optionally substituted ammonium ion; R1 represents an optionally substituted C3-C35 hydrocarbyl group; and each of R2, R3, R4, R5 and R6 independently represents hydrogen or a C1-C4 alkyl group; wherein at least 50% of the carbon atoms provided by the moiety NR6CR2R3CR4R5SC>3X in the compound of formula (II) are from a renewable carbon source. In some preferred embodiments the surfactant composition of the second aspect may be provided by the method of the first aspect. According to a third aspect of the present invention there is provided a compound of formula (II): (II) wherein X is hydrogen, a metal ion or an optionally substituted ammonium ion; R1 represents an optionally substituted C3-C35 hydrocarbyl group; and each of R2, R3, R4 and R5 independently represents hydrogen or a C1-C4 alkyl group; wherein at least 50% of the carbon atoms provided by the moiety NR6CR2R3CR4R5SC>3X in the compound of formula (II) are from a renewable carbon source. In the first, second and third (and further) aspects of the invention R1 represents an optionally substituted C3-C35 hydrocarbyl group. For the avoidance of doubt the present invention includes embodiments in which mixtures of compounds are present and thus R1 may represent different hydrocarbyl groups including mixtures of differing carbon chain length within the C3-C35 range. According to a fourth aspect of the present invention there is provided a compound of formula (I): wherein X is hydrogen, a metal ion or an optionally substituted ammonium ion; and each of R2, R3, R4, R5 and R6 independently represents hydrogen or a C1-C4 alkyl group; wherein at least 50% of the carbon atoms in the compound are from a renewable carbon source. Preferred features of the first, second, third and fourth aspects will now be described. References herein to the surfactant composition of the present invention unless otherwise stated may refer to the surfactant composition of the second aspect and/or the surfactant composition provided by the first aspect. R1 represents an optionally substituted C3-C35 hydrocarbyl group, R2, R3, R4 and R5 each independently represents hydrogen or a substituted or unsubstituted C1-C4 alkyl group, provided that at least one of R2, R3, R4 and R5 is not hydrogen, and X represents a cation. Suitably R1 represents an optionally substituted C3-C35 alkyl, C3-C35 alkenyl, C6-C12 aryl or Cs- C22 alkyl-Ce-Ci2 aryl group. More suitably, R1 represents an optionally substituted C3-C35 al