EP3898920A1 - Activateurs de blanchiment contenant deux groupes ammonium quaternaire - Google Patents

Activateurs de blanchiment contenant deux groupes ammonium quaternaire

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Publication number
EP3898920A1
EP3898920A1 EP19818025.9A EP19818025A EP3898920A1 EP 3898920 A1 EP3898920 A1 EP 3898920A1 EP 19818025 A EP19818025 A EP 19818025A EP 3898920 A1 EP3898920 A1 EP 3898920A1
Authority
EP
European Patent Office
Prior art keywords
linear
branched
carbon atoms
compound
alkyl
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.)
Withdrawn
Application number
EP19818025.9A
Other languages
German (de)
English (en)
Inventor
Sascha Schaefer
Svenja NEUHAUS
Antje Gebert-Schwarzwaelder
Nora SCHMIDT
Christa JUNKES
Arne Jansen
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.)
Henkel AG and Co KGaA
Original Assignee
Henkel AG and Co KGaA
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 Henkel AG and Co KGaA filed Critical Henkel AG and Co KGaA
Publication of EP3898920A1 publication Critical patent/EP3898920A1/fr
Withdrawn legal-status Critical Current

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Classifications

    • 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
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/39—Organic or inorganic per-compounds
    • C11D3/3902—Organic or inorganic per-compounds combined with specific additives
    • C11D3/3905—Bleach activators or bleach catalysts
    • C11D3/3907—Organic compounds
    • C11D3/3917—Nitrogen-containing compounds
    • C11D3/3927—Quarternary ammonium compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06L—DRY-CLEANING, WASHING OR BLEACHING FIBRES, FILAMENTS, THREADS, YARNS, FABRICS, FEATHERS OR MADE-UP FIBROUS GOODS; BLEACHING LEATHER OR FURS
    • D06L1/00—Dry-cleaning or washing fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods
    • D06L1/12—Dry-cleaning or washing fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods using aqueous solvents
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06L—DRY-CLEANING, WASHING OR BLEACHING FIBRES, FILAMENTS, THREADS, YARNS, FABRICS, FEATHERS OR MADE-UP FIBROUS GOODS; BLEACHING LEATHER OR FURS
    • D06L4/00—Bleaching fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods; Bleaching leather or furs
    • D06L4/10—Bleaching fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods; Bleaching leather or furs using agents which develop oxygen
    • D06L4/12—Bleaching fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods; Bleaching leather or furs using agents which develop oxygen combined with specific additives

Definitions

  • the present invention relates to a compound of formula (I) and additionally to a method to manufacture the compound of formula (I). Furthermore, the invention is directed to a use of the compound of formula (I) as a bleach activator and to a laundry detergent composition, an automatic dishwashing composition, and an industrial cotton bleach composition, which comprise at least one compound of formula (I) according to the invention.
  • Bleachable stains or colored materials on textiles or on hard surfaces can be discolored, oxidized and ultimately removed using highly active bleach activators in combination with a source of hydrogen peroxide.
  • TAED tetraacetylethylenediamine
  • Some commonly used bleach activators such as tetraacetylethylenediamine (TAED) show a low water solubility at low temperatures. Low temperature washing and cleaning of laundry and hard surfaces requires more reactive bleach activators, which aliphatic activators cannot achieve.
  • Commonly used activators like TAED provide only less reactive bleach-active compounds such as peracids and are less efficient in the generation of the same. Benzylic peracids have a much higher activity towards bleachable stains and colored materials, which makes them more sustainable and allow formulations, which are more compact.
  • quaternary ammonium groups-containing lactam-based compounds can be applied as bleach activators, preferably in laundry detergents, automatic dishwashing agents or industrial cotton bleach compositions. These compounds provide higher solubility in water, preferably at low temperatures, and higher affinity towards fibers, preferably cotton fibers, in comparison with non- charged or anionic bleach activators. Furthermore, they provide a higher bleaching activity compared to aliphatic bleach activators such as TAED. Thereby, lower dosages of bleach activators are required in a composition, to achieve the same bleaching effect.
  • the present invention relates in a first aspect to a compound of formula (I)
  • a 1 , A 2 and A 3 are independently selected from O, S, or Se;
  • Z 1 and Z 2 are independently selected from linear or branched alkyl, cycloalkyl, or aryl, or linear or branched alkylcycloalkyl or alkylaryl having up to 30 carbon atoms, respectively, and which can contain at least one heteroatom selected from O, S, N, Si, Se or P and/or which can be substituted by at least one substituent, preferably selected from hydroxy-, linear or branched C1 -C6 alkoxy-, amino-, nitro-, fluoro-, chloro-, bromo-, iodo-, carbonyl-, carboxyl-, linear or branched C1 -C6 ester- or ether-, mercapto- , sulfonyl-, cyano-, or linear or branched C1 -C6 alkyl-, alkenyl- or alkynyl-, cycloalkyl-, or aryl groups, whereby the hydrocarbon groups can contain at least one
  • R 1 to R 10 are independently selected from hydrogen, linear or branched alkyl, cycloalkyl, or aryl, or linear or branched alkylcycloalkyl or alkylaryl having up to 30 carbon atoms, respectively, and which can contain at least one heteroatom selected from O, S, N, Si, Se or P, and/or which can be substituted by at least one substituent, preferably selected from hydroxyl-, linear or branched C1 -C6 alkoxy-, amino-, nitro-, fluoro-, chloro-, bromo-, iodo-, carbonyl-, carboxyl-, linear or branched C1 -C6 ester- or ether-, mercapto-, sulfonyl-, cyano-, or linear or branched C1 -C6 alkyl-, alkenyl- or alkynyl-, cycloalkyl-, or aryl groups, whereby the hydrocarbon groups can contain
  • R 5 ⁇ R 6 , and R 7 and/or R 8 , R 9 , and R 10 form together with the N atom to which they are attached a hydrocarbon ring with up to 8 carbon atoms, wherein the ring can contain at least one double bond, and/or wherein the ring can be substituted by at least one substituent, preferably selected from hydroxyl-, linear or branched C1 -C6 alkoxy-, amino-, nitro-, fluoro-, chloro-, bromo-, iodo-, carbonyl-, carboxyl-, linear or branched C1 -C6 ester- or ether-, mercapto-, sulfonyl-, cyano-, or linear or branched C1 -C6 alkyl-, alkenyl- or alkynyl-, cycloalkyl-, or aryl groups, whereby the hydrocarbon groups can contain at least one heteroatom selected from O, S, N, Si, Se
  • R 1 to R 4 are as defined above;
  • n is an integer from 0 to 12;
  • X is selected from chloride, bromide, iodide, tosylate, mesylate, triflate, sulfate, carbonate, or phosphate, wherein 2 X- can be X 2- , or 2/3 X 3- .
  • the invention relates to a method of manufacturing a compound of formula (I) according to the invention, comprising or consisting of the steps: a) reacting a compound of formula (IV)
  • A is selected from O, S, or Se
  • R 1 to R 4 are independently selected from hydrogen, linear or branched alkyl, cycloalkyl or aryl, or linear or branched alkylcycloalkyl or alkylaryl having up to 30 carbon atoms, respectively, and which can contain at least one heteroatom selected from O, S, N, Si, Se or P, and/or which can be substituted by at least one substituent, preferably selected from hydroxyl-, linear or branched C1 -C6 alkoxy-, amino-, nitro-, fluoro-, chloro-, bromo-, iodo, carbonyl-, carboxyl-, linear or branched C1 -C6 ester- or ether-, mercapto-, sulfonyl-, cyano-, or linear or branched C1 -C6 alkyl-, alkenyl- or alkynyl-, cycloalkyl-, or aryl groups, whereby the hydrocarbon groups can contain at least
  • n is an integer from 0 to 12; with at least one compound of formula (V), preferably in stoichiometric excess of the at least one compound of formula (V) in relation to the compound of formula (IV),
  • A is selected from O, S, or Se;
  • Z is selected from linear or branched alkyl, cycloalkyl or aryl or linear or branched alkylcycloalkyl or alkylaryl having up to 30 carbon atoms, respectively, and which can contain at least one heteroatom selected from O, S, N, Si, Se or P and/or which can be substituted by at least one substituent, preferably selected from hydroxy-, linear or branched C1 -C6 alkoxy-, amino-, nitro-, fluoro-, chloro-, bromo-, iodo- , carbonyl-, carboxyl-, linear and branched C1 -C6 ester- or ether-, mercapto-, sulfonyl-, cyano-, or linear or branched C1 -C6 alkyl-, alkenyl- or alkynyl-, cycloalkyl-, or aryl groups, whereby the hydrocarbon groups can contain at least one heteroatom selected from O, S
  • R 17 is Cl, Br or I
  • R 18 is linear or branched alkyl, cycloalkyl, or aryl, or linear or branched alkylcycloalkyl or alkylaryl having up to 30 carbon atoms, respectively, and which can contain at least one heteroatom selected from O, S, N, Si, Se or P, and/or which can be substituted by at least one substituent, preferably selected from hydroxyl-, linear or branched C1 -C6 alkoxy-, amino-, nitro-, fluoro-, chloro-, bromo-, iodo-, carbonyl-, carboxyl-, linear or branched C1 -C6 ester- or ether-, mercapto-, sulfonyl-, cyano-, or linear or branched C1 -C6 alkyl-, alkenyl- or alkynyl-, cycloalkyl-, or aryl groups, whereby the hydrocarbon groups can contain at least one heteroatom selected from O
  • R 19 to R 21 are independently selected from hydrogen, linear or branched alkyl, cycloalkyl, or aryl, or linear or branched alkylcycloalkyl or alkylaryl having up to 30 carbon atoms, respectively, and which can contain at least one heteroatom selected from O, S, N, Si, Se or P, and/or which can be substituted by at least one substituent, preferably selected from hydroxyl-, linear or branched C1 -C6 alkoxy-, amino-, nitro-, fluoro-, chloro-, bromo-, iodo-, carbonyl-, carboxyl-, linear or branched C1 -C6 ester- or ether-, mercapto-, sulfonyl-, cyano-, or linear or branched C1 -C6 alkyl-, alkenyl- or alkynyl-, cycloalkyl-, or aryl groups, whereby the hydrocarbon groups can
  • R 19 to R 21 form together with the N atom to which they are attached a hydrocarbon ring with up to 8 carbon atoms, wherein the ring can contain at least one double bond, and/or the ring can be substituted by at least one substituent, preferably selected from hydroxyl-, linear or branched C1 -C6 alkoxy-, amino-, nitro-, fluoro-, chloro-, bromo-, iodo-, carbonyl-, carboxyl-, linear or branched C1 -C6 ester- or ether-, mercapto-, sulfonyl-, cyano-, or linear or branched C1 -C6 alkyl-, alkenyl- or alkynyl-, cycloalkyl-, or aryl groups, whereby the hydrocarbon groups can contain at least one heteroatom selected from O, S, N, Si, Se or P; to obtain at least one compound of formula (I), (II) or (III).
  • the invention relates to a use of the compound according to the invention, as a bleach activator.
  • the invention relates to a laundry detergent composition, to an automatic dishwashing composition and to an industrial cotton bleaching composition comprising at least one compound according to the invention and a bleach.
  • One or more relates to“at least one” and comprises 1 , 2, 3, 4, 5, 6, 7, 8, 9 or more of the referenced species.
  • “at least one” means“one or more”, i.e. 1 , 2, 3, 4, 5, 6, 7, 8, 9 or more.
  • “At least one”, as used herein in relation to any component, refers to the number of chemically different atoms or molecules, i.e. to the number of different types of the referenced species, but not to the total number of atoms or molecules.
  • “at least one compound of formula (I)” means that at least one type of compound of formula (I) falling within the definition can be part of the composition, but that also two or more different compounds according to formula (I) can be present, but does not mean that several compounds of only one type of compound may be present.
  • Up to x carbon atoms for example“up to 30 carbon atoms” according to the invention refers to hydrocarbon groups with a minimum of 1 and a maximum of 30 carbon atoms, the numbers being integers. The possibility of 0 carbon atoms is excluded, when using the wording of “up to x carbon atoms”. In case of branched or cyclic hydrocarbon groups the lower limit is 3 carbon atoms.
  • R 1 to R 21 are chosen from hydrocarbon groups or are substituted by a hydrocarbon group, for example linear or branched C1 -C6 alkyl-, alkenyl- or alkynyl-, cycloalkyl-, or aryl groups, they can contain heteroatoms, such as O, S, N, Si, Se, or P.
  • Groups based on hydrogen and carbon atoms, which already contain at least one heteroatom, such as ester- or carboxyl groups, are not included in the definition of hydrocarbon groups according to the invention.
  • X- represents chloride, bromide, iodide, tosylate, mesylate, or triflate.
  • 2 X- is X 2- , a doubly negatively charged ion, such as sulfate or carbonate, or 2 X- can represent 2/3 of a triply negatively charged ion X 3- , such as phosphate, which is then shared between several cations, for example two phosphate ions are the counter ions for the three cations of the compounds of formula (I).
  • the expression "essentially free of means that the respective compound can be contained in the composition in principle, but then be present in a quantity that does not interfere with a function of the other components.
  • the property "essentially free of a particular compound is preferably considered to be a total weight of less than 0.1 wt.-%, more preferably less than 0.001 wt.-%, in particular free of this particular compound, based on the total weight of the composition.
  • Numeric ranges specified in the format "in/from x to y" include the values specified. If several preferred numeric ranges are specified in this format, it goes without saying that all ranges resulting from the combination of the different endpoints will also be included.
  • Molecular weight data referto the weight-average molecular weight in g/mol, unless the number-average molecular weight is explicitly mentioned. It is preferably determined by GPC using polystyrene standards.
  • the compound according to the invention is a compound of formula (II):
  • a 1 , A 2 and A 3 are independently selected from O, S, or Se;
  • R 1 to R 16 are independently selected from hydrogen, linear or branched alkyl, cycloalkyl, or aryl, or linear or branched alkylcycloalkyl or alkylaryl having up to 30 carbon atoms, respectively, preferably up to 15 carbon atoms, more preferably up to 10 carbon atoms, and which can contain at least one heteroatom selected from O, S, N, Si, Se or P, and/or which can be substituted by at least one substituent, preferably selected from hydroxyl-, linear or branched C1 -C6 alkoxy-, amino-, nitro-, fluoro-, chloro-, bromo-, iodo- , carbonyl-, carboxyl-, linear or branched C1 -C6 ester- or ether-, mercapto-, sulfonyl-, cyano-, or linear or branched C1 -C6 alkyl-, alkenyl- or alkynyl-,
  • R 5 ⁇ R 6 , and R 7 and/or R 8 , R 9 , and R 10 form together with the N atom to which they are attached a hydrocarbon ring with up to 8 carbon atoms, wherein the ring can contain at least one double bond, and/or the ring can be substituted by at least one substituent, preferably selected from hydroxyl-, linear or branched C1 -C6 alkoxy-, amino-, nitro-, fluoro-, chloro-, bromo-, iodo-, carbonyl-, carboxyl-, linear or branched C1 -C6 ester- or ether-, mercapto-, sulfonyl-, cyano-, or linear or branched C1 -C6 alkyl-, alkenyl- or alkynyl-, cycloalkyl-, or aryl groups, whereby the hydrocarbon groups can contain at least one heteroatom selected from O, S, N, Si, Se or P
  • R 1 to R 4 and R 11 to R 16 are as defined above;
  • n is an integer from 0 to 12;
  • X is selected from chloride, bromide, iodide, tosylate, mesylate, triflate, sulfate, carbonate, or phosphate, wherein 2 X- can be X 2- , or 2/3 X 3- .
  • the compound according to the invention is a compound of formula (II), wherein
  • a 1 , A 2 and A 3 are the same, preferably O; and/or
  • n is 1 or 2, preferably 1 ;
  • R 1 to R 4 and R 11 to R 16 are independently selected from linear or branched C1 -C4 alkyl and hydrogen, preferably hydrogen; or
  • R 5 , R 6 , and R 7 and/or R 8 , R 9 , and R 10 form together with the N atom to which they are attached a hydrocarbon ring with up to 8 carbon atoms, preferably with 5 carbon atoms, wherein the ring preferably contains at least one double bond, more preferably 3 double bonds, wherein the ring is preferably pyridine, and/or the ring, preferably the pyridine, can be substituted by at least one substituent, preferably selected from hydroxyl-, linear or branched C1 -C6 alkoxy-, amino-, nitro-, fluoro-, chloro-, bromo-, iodo-, carbonyl-, carboxyl-, linear or branched C1 -C6 ester- or ether-, mercapto-, sulfonyl-, cyano-, or linear or branched C1 -C6 alkyl-, alkenyl- or alkynyl-,
  • R 1 to R 4 and R 11 to R 16 are as defined above; and/or
  • X- is selected from chloride, bromide, or iodide.
  • the compound according to the invention is a compound of formula
  • the invention relates to a method to manufacture the compound according to the invention, comprising or consisting of the steps: a) reacting a compound of formula (IV)
  • A is selected from O, S, or Se, preferably O;
  • R 1 to R 4 are independently selected from hydrogen, linear or branched alkyl, cycloalkyl or aryl, or linear or branched alkylcycloalkyl or alkylaryl having up to 30 carbon atoms, respectively, preferably up to 15 carbon atoms, more preferably up to 10 carbon atoms, and which can contain at least one heteroatom selected from O, S, N, Si, Se or P, and/or which can be substituted by at least one substituent, preferably selected from hydroxyl-, linear or branched C1 -C6 alkoxy-, amino-, nitro-, fluoro-, chloro-, bromo-, iodo, carbonyl-, carboxyl-, linear or branched C1 -C6 ester- or ether-, mercapto-, sulfonyl-, cyano-, or linear or branched C1 -C6 alkyl-, alkenyl- or alkynyl-, cyclo
  • n is an integer from 0 to 12, preferably 1 or 2, more preferably 1 ; with at least one compound of formula (V), preferably in stoichiometric excess of the at least one compound of formula (V) in relation to the compound of formula (IV), more preferably more than two equivalents of the at least one compound of formula (V) in relation to the compound of formula (IV) (V),
  • A is selected from O, S, or Se, preferably O;
  • Z is selected from linear or branched alkyl, cycloalkyl or aryl or linear or branched alkylcycloalkyl or alkylaryl having up to 30 carbon atoms, respectively, preferably up to 15 carbon atoms, more preferably up to 10 carbon atoms, and which can contain at least one heteroatom selected from O, S, N, Si, Se or P and/or which can be substituted by at least one substituent, preferably selected from hydroxy-, linear or branched C1 -C6 alkoxy-, amino-, nitro-, fluoro-, chloro-, bromo-, iodo-, carbonyl-, carboxyl-, linear and branched C1 -C6 ester- or ether-, mercapto-, sulfonyl-, cyano-, or linear or branched C1 -C6 alkyl-, alkenyl- or alkynyl-, cycloalkyl-, or aryl
  • R 17 is Cl, Br or I
  • R 18 is linear or branched alkyl, cycloalkyl, or aryl, or linear or branched alkylcycloalkyl or alkylaryl having up to 30 carbon atoms, respectively, preferably up to 15 carbon atoms, more preferably up to 10 carbon atoms, and which can contain at least one heteroatom selected from O, S, N, Si, Se or P, and/or which can be substituted by at least one substituent, preferably selected from hydroxyl-, linear or branched C1 -C6 alkoxy-, amino-, nitro-, fluoro-, chloro-, bromo-, iodo-, carbonyl-, carboxyl-, linear or branched C1 -C6 ester- or ether-, mercapto-, sulfonyl-, cyano-, or linear or branched C1 -C6 alkyl-, alkenyl- or alkynyl-, cycloalkyl-, or
  • A, Z, n, R 1 to R 4 , and R 18 are as defined above; b) reacting the at least one compound of formula (VI) with at least one compound of formula (VII), preferably in stoichiometric excess of the at least one compound of formula (VII) in relation to the compound of formula (VI), more preferably more than two equivalents of the at least one compound of formula (VII) in relation to the compound of formula (VI);
  • R 19 to R 21 are independently selected from hydrogen, linear or branched alkyl, cycloalkyl, or aryl, or linear or branched alkylcycloalkyl or alkylaryl having up to 30 carbon atoms, respectively, preferably up to 15 carbon atoms, more preferably up to 10 carbon atoms, and which can contain at least one heteroatom selected from O, S, N, Si, Se or P, and/or which can be substituted by at least one substituent, preferably selected from hydroxyl-, linear or branched C1 -C6 alkoxy-, amino-, nitro-, fluoro-, chloro-, bromo-, iodo-, carbonyl-, carboxyl-, linear or branched C1 -C6 ester- or ether-, mercapto-, sulfonyl-, cyano-, or linear or branched C1 -C6 alkyl-, alkenyl- or alkynyl-,
  • R 19 to R 21 form together with the N atom to which they are attached a hydrocarbon ring with up to 8 carbon atoms, preferably with 5 carbon atoms, wherein the ring can contain at least one double bond, preferably 3 double bonds, wherein the ring is preferably pyridine, and/or the ring can be substituted by at least one substituent, preferably selected from hydroxyl-, linear or branched C1 -C6 alkoxy-, amino-, nitro, fluoro-, chloro, bromo-, iodo-, carbonyl-, carboxyl-, linear or branched C1 -C6 ester- or ether-, mercapto-, sulfonyl-, cyano-, or linear or branched C1 -C6 alkyl-, alkenyl- or alkynyl-, cycloalkyl-, or aryl groups, whereby the hydrocarbon groups can contain at least one heteroatom selected from O, S, N,
  • the at least one compound of formula (V) is only one compound of formula
  • the at least one compound of formula (VI) is only one compound of formula
  • the at least one compound of formula (VII) is only one compound of formula
  • bleach activators are also known under the name“peracid precursors”.
  • the compound according to the invention is comprised in laundry detergent compositions, automatic dishwashing compositions or industrial cotton bleaching compositions.
  • the at least one compound according to the invention is contained in the composition in 0.1 to 50 wt.-%, preferably 0.25 to 25 wt.-%, more preferably 1 to 10 wt.-%, based on the total weight of the composition.
  • the composition according to the invention has a pH value of from 4 to 14, preferably 6 to 12, more preferably 7 to 10.
  • the laundry detergent compositions, automatic dishwashing compositions or industrial cotton bleaching compositions according to the present invention comprise at least one compound according to the invention and further contain a bleach.
  • the bleach can be any type of hydrogen peroxide source.
  • Source of hydrogen peroxide include any convenient compound or mixture, which under typical use conditions provides an effective amount of hydrogen peroxide.
  • Levels of the source of hydrogen peroxide in the bleaching composition can vary widely and are in some embodiments from about 0.5 wt.-% to about 60 wt.-%, and in some embodiments, from about 0.5 wt.-% to about 25 wt.-% of the composition.
  • the source of hydrogen peroxide can be any hydrogen peroxide source known in the art, including, but not limited to, hydrogen peroxide itself.
  • the source of hydrogen peroxide can be a perborate, e.g., sodium perborate (any hydrate, including the mono- or tetra-hydrate), sodium carbonate peroxyhydrate or equivalent percarbonate salts, sodium pyrophosphate peroxyhydrate, urea peroxyhydrate, or sodium peroxide.
  • a perborate e.g., sodium perborate (any hydrate, including the mono- or tetra-hydrate), sodium carbonate peroxyhydrate or equivalent percarbonate salts, sodium pyrophosphate peroxyhydrate, urea peroxyhydrate, or sodium peroxide.
  • any convenient hydrogen peroxide sources can also be used.
  • the percarbonate bleach comprises dry particles having an average particle size in the range from about 500 micrometer to about 1 ,000 micrometer, not more than about 10 wt.-% of said particles being smaller than about 200 micrometer and not more than about 10 wt.-% of said particles being larger than about 1 ,250 micrometer.
  • the percarbonate can be coated with silicate, borate or water-soluble surfactants.
  • composition according to the invention can further contain bleach activators different from the compound according to formula (I), which can be chosen from conventional compounds known in the art.
  • Typical conventional bleach activators include nonanoyloxybenzene sulfonate (NOBS) and tetraacetyl ethylenediamine (TAED), and combinations thereof.
  • compositions according to the invention are essentially free of any further bleach activator different from the compound according to formula (I).
  • compositions according to the invention are essentially free of tetraacetylethylenediamine (TAED).
  • compositions according to the invention may further comprise components selected from surfactants, acidifiers, alkalizing agents, anti-crease compounds, antibacterial/antimicrobial substances, antioxidants, antideposition agents, antistatic agents, bitter substances, bleach stabilizers, builder substances, corrosion inhibitors, ironing aids, cobuilders, further fragrances or pro-fragrances, shrinkage inhibitors, electrolytes, emulsifiers, enzymes, enzyme stabilizers, protease inhibitors, colorants, dyes, dye transfer inhibitors, fluorescent agents, fungicides, germicides, metal sequestering agents, odor-complexing substances, auxiliary agents, hydrotropics, rinse aids, complexing agents, preservatives, optical brighteners, perfume carriers, pearl-luster agents, pH control agents, phobing and impregnating agents, polymers, swelling and sliding fasteners, foam inhibitors, layered silicates, dirt- repellent substances, organic solvents, silicone oils, soil-release active substances, UV-protective substances, viscos
  • the optional components can be comprised in the composition according to the invention in amounts of from 0.01 to 60 wt.-%, preferably of from 0.1 to 40 wt.-%, more preferably of from 1 to 25 wt.-%.
  • liquid compositions are concerned, they contain a solvent system.
  • the solvent system of compositions according to the invention can be a solvent system containing water alone or mixtures of organic solvents, preferably alcohols, either without or preferably with water.
  • Preferred organic solvents include every solvent, which is suitable in the field of laundry detergents, dishwashing agents or bleaching compositions.
  • Solvent systems can be absent, for example from anhydrous solid embodiments of the invention.
  • solvent systems are present at levels in the range of 0.1 wt.-% to 98 wt.-%, preferably of 1 wt.-% to 50 wt.-%, more preferably of 2 wt.-% to 25 wt.-%.
  • compositions are aqueous compositions, more preferably aqueous, liquid compositions.
  • compositions according to the invention further comprise at least one surfactant selected from anionic surfactants, cationic surfactants, amphoteric surfactants, or non-ionic surfactants.
  • Suitable non-ionic surfactants are in particular, but without being limited to, ethoxylation and/or propoxylation products of alkyl glycosides and/or linear or branched alcohols each with 8 to 18 C atoms in the alkyl moiety and 3 to 20, preferably 4 to 10 alkyl ether groups. Furthermore, corresponding ethoxylation and/or propoxylation products of N-alkylamines, vicinal diols, fatty acid esters and fatty acid amides, which correspond to the above-mentioned long-chain alcohol derivatives with regard to the alkyl moiety, and of alkylphenols with 5 to 12 C atoms in the alkyl radical are useful.
  • non-ionic surfactants such as fatty alcohol polyglycol ethers, alkyl polyglucoside, or fatty acid glucamide, are useful, in particular in amounts of 0.1 -25 wt.-%, based on the total weight of the composition.
  • Suitable anionic surfactants are preferably soaps and soaps containing sulphate or sulphonate groups with preferably alkali ions as cations.
  • Suitable soaps are preferably the alkali salts of saturated or unsaturated fatty acids with 8 to 18 carbon atoms. These fatty acids can also be used in incompletely neutralized form.
  • the useful sulfate-type surfactants include the salts of the sulfuric acid half-esters of fatty alcohols with 8 to 18 carbon atoms and the sulfation products of said non-ionic surfactants with a low degree of ethoxylation.
  • the useful surfactants of the sulfonate-type include, for example, linear alkylbenzene sulfonates with 8 to 14 carbon atoms in the alkyl moiety, alkane sulfonates with 8 to 18 carbon atoms, and olefin sulfonates with 8 to 18 C atoms, which are formed during the reaction of corresponding mono olefins with sulfur trioxide, as well as alpha-sulfo fatty acid esters, which are formed during the sulfonation of fatty acid methyl or ethyl esters.
  • alkylbenzene sulfonate or alkylsulfate is present in the composition according to the invention, preferably in amounts of 0.1 to 40 wt.-%, based on the total weight of the composition.
  • Cationic surfactants are preferably selected from, but without being limited to, esterquats and/or quaternary ammonium compounds (QAV) according to the general formula (R I )(R")(R III )(R IV )N + X- in which R' to R IV represent identical or different C1 to C22 alkyl radicals, C7 to C28 arylalkyl radicals or heterocyclic radicals, wherein two or, in the case of an aromatic integration, such as in pyridine, even three radicals together with the nitrogen atom form the heterocycle, for example a pyridinium or imidazolinium compound, and X- represents halide ions, sulfate ions, hydroxide ions or similar anions.
  • QAV quaternary ammonium compounds
  • QAV can be produced by reaction of tertiary amines with alkylating agents, e.g. methyl chloride, benzyl chloride, dimethyl sulfate, dodecyl bromide, but also ethylene oxide.
  • alkylating agents e.g. methyl chloride, benzyl chloride, dimethyl sulfate, dodecyl bromide, but also ethylene oxide.
  • alkylating agents e.g. methyl chloride, benzyl chloride, dimethyl sulfate, dodecyl bromide, but also ethylene oxide.
  • alkylating agents e.g. methyl chloride, benzyl chloride, dimethyl sulfate, dodecyl bromide, but also ethylene oxide.
  • the alkylation of tertiary amines with a long alkyl radical and two methyl groups is particularly simple. Quaternization of tertiary amines with two long radicals
  • QAVs which can be used, include benzalkonium chloride (N-alkyl-N,N-dimethyl-benzylammonium chloride), benzalkone B (m,p- dichlorobenzyldimethyl-Ci2-alkylammonium chloride, benzoxonium chloride (benzyl-dodecyl-bis-(2- hydroxyethyl)-ammonium chloride), cetrimonium bromide (N-hexadecyl-N,N-trimethyl-ammonium bromide), benzetonium chloride (N,N dimethyl-N [2-[2-[p-(1 ,1 ,3,3-tetramethylbutyl)phenoxy]-ethoxy]- ethyl]-benzylammonium chloride), dialkyldimethylammonium chlorides such as di-n-decyl- dimethylammonium chloride, didecyldimethylammonium bromide, di
  • esterquats are methyl N-(2-hydroxyethyl)-N,N-di(talgacyl-oxyethyl)ammonium-metho-sulfate, bis-(palmitoyl)-ethyl-hydroxyethyl-methyl-ammonium-methosulfate or methyl-N,N-bis(acyl-oxyethyl)-N- (2-hydroxyethyl)ammonium-methosulfate.
  • esterquats are used in amounts of 0.1 to 30 wt.-%, based on the total weight of the composition.
  • Suitable amphoteric/zwitterionic surfactants include amine oxides and betaines.
  • Suitable surfactants can also be fatty amine ethoxylates, preferably in amounts of 0.01 to 4 wt.-%, based on the total weight of the composition.
  • composition according to the invention may further comprise water-soluble and water-insoluble, organic and inorganic builder substances.
  • Water-soluble organic builder substances include for example, but without being limited to, polycarboxylic acids, in particular citric acid and sugar acids, monomeric and polymeric aminopolycarboxylic acids, in particular methylglycinediacetic acid, nitrilotriacetic acid and ethylenediaminetetraacetic acid as well as polyaspartic acid, polyphosphonic acids, in particular aminotris(methylenephosphonic acid), ethylenediaminetetrakis(methylene- phosphonic acid) and 1 -hydroxyethane-1 ,1 -diphosphonic acid, polymeric hydroxy compounds such as dextrin, polymeric (poly)carboxylic acids, polymeric acrylic acids, methacrylic acids, maleic acids and copolymers thereof, which may also contain small amounts of polymerizable substances without carboxylic acid functionality when polymerized.
  • Suitable, but less preferred compounds of this class are copolymers of acrylic acid or methacrylic acid with vinyl ethers such as vinyl methyl ethers, vinyl esters, ethylene, propylene and styrene, in which the proportion of acid is at least 50 wt.-%.
  • the organic builder substances can be used, preferably for the production of liquid agents, in the form of aqueous solutions, preferably in the form of 30 to 50 wt.-% aqueous solutions. All acids mentioned are usually used in the form of their water-soluble salts, in particular their alkali salts.
  • Organic builder substances can be comprised in compositions according to the invention, in amounts of up to 40 wt.-%, preferably up to 25 wt.-% and more preferably from 0.1 wt.-% to 8 wt.-%. Amounts near this upper limit are preferably used in pasty or liquid, in particular water-containing agents according to the invention. Laundry after-treatment agents, such as fabric softeners, may also be free of organic builder. It may be preferred that the composition comprises low levels of phosphate salt and/or zeolite, for example from 0.1 to 10 wt.-%, preferably from 1 to 5 wt.-%. Optionally, the composition may be free of strong builder.
  • Alkali silicates and aluminum silicates and polyphosphates, preferably sodium triphosphate are particularly suitable as water-soluble inorganic builder materials.
  • water-insoluble, water-dispersible inorganic builder materials crystalline or amorphous alkali metal aluminum silicates, if desired, can be used in quantities of up to 50 wt.-%, preferably not more than 40 wt.-%, and in liquid media, in particular from 1 wt.-% to 5 wt.-%.
  • crystalline sodium aluminum silicates in detergent quality in particular zeolites A, P and, where appropriate, X, are preferred. Quantities near this upper limit are preferably used in solid, particulate agents.
  • suitable aluminum silicates have no particles with a grain size of more than 30 pm and preferably consist of at least 80 wt.-% of particles with a size of less than 10 pm.
  • the builder materials are selected from zeolites, polycarboxylates or sodium citrate.
  • builder substances if desired, can be present in compositions according to the invention in amounts of up to 60 wt.-%, preferably of 1 wt.-% to 40 wt.-%.
  • Laundry after treatment agents such as softeners, are preferably free of inorganic builder substances.
  • the composition according to the invention is a liquid at 25 °C
  • composition according to the invention is a solid at 25 °C.
  • compositions relate to compositions, which are fluid or flowable at standard conditions (approx. 20-25 °C, approx. 1013 mbar at sea level).
  • Liquid compositions also comprise gellike and paste-like compositions. “Solid” is understood to mean all solid presentation forms, for example powders, granulates or extrudates.
  • a powdery composition for example, can exist as a free-flowing powder, in particular with a bulk density of 300 g/L to 1200 g/L, especially 500 g/L to 900 g/L or 600 g/L to 850 g/L.
  • compositions according to the invention are preferably in the form of a molded object, in particular a compacted material, principally a tablet.
  • a molded object in particular a compacted material, principally a tablet.
  • the molded object can also be a granulate for example that is comprised in a bag or in a cast shape.
  • compositions according to the invention can be presented as one-phase or multi-phase products.
  • Compositions in particular automatic dishwashing compositions or laundry detergents, in particular with one, two, three or four phases, are preferred.
  • Automatic dishwashing compositions in the form of a prefabricated unit dose with two or more phases are particularly preferred.
  • tablets with two or more phases are particularly preferred, for example two-layer tablets, in particular two-layer tablets with a recess and a molded object in the recess.
  • compositions according to the invention are preferably prefabricated as unit doses. These unit doses preferably contain the necessary quantity of washing or cleaning active substances for one cleaning cycle. Preferred unit doses weigh between 12 and 30 g, preferably between 14 and 26 g and especially between 15 and 22 g.
  • the volume of the abovementioned unit doses and their three-dimensional shape are preferably chosen such that the prefabricated units can be dosed by being placed in the dosing chamber of a dishwasher. Consequently, the volume of the unit dose is preferably between 10 and 35 ml_, more preferably between 12 and 30 ml_ and most preferably between 15 and 25 ml_.
  • the compositions according to the invention, in particular the prefabricated unit doses have, in a preferred embodiment, a water-soluble coating.
  • Lactose and ovalbumin were mixed in 3:1 ratio (total 0.5 g), solved in distilled water and stirred for 10 min at room temperature. The mixture was then freeze-dried, ground in a mortar and heated in an oven at 160°C for 20 min and afforded after cooling to room temperature a yellow-brown powder.
  • Sodium percarbonate stock solution was prepared by dissolving 0.375 g in 100 mL water.
  • Activator stock solution was prepared by dissolving 0.05 g in 100 mL water. Table 3: Preparation of respective solutions
  • a test solution was prepared by dissolving 2.5 mg Morin in 100 ml_ water followed by adjustment of the pH value to 10-1 1 by addition of a suitable amount of NaOH. Then 98.0 mg sodium percarbonate was added followed by 13.1 mg of TAED or the compound of Example 1 . The resulting yellow solution was then stirred at room temperature and checked visually over time until the yellow color fully disappeared and a transparent solution was obtained.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Inorganic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
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Abstract

La présente invention concerne un composé de formule (I) et un procédé de fabrication du composé de formule (I). En outre, l'invention concerne une utilisation du composé de formule (I) en tant qu'activateur de blanchiment et une composition de détergent à lessive, une composition de lavage de vaisselle automatique, et une composition de blanchiment de coton industriel, qui comprennent au moins un composé de formule (I) selon l'invention.
EP19818025.9A 2018-12-21 2019-12-09 Activateurs de blanchiment contenant deux groupes ammonium quaternaire Withdrawn EP3898920A1 (fr)

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DE102018133517 2018-12-21
PCT/EP2019/084202 WO2020126608A1 (fr) 2018-12-21 2019-12-09 Activateurs de blanchiment contenant deux groupes ammonium quaternaire

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EP3898920A1 true EP3898920A1 (fr) 2021-10-27

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US3775333A (en) * 1972-06-30 1973-11-27 American Cyanamid Co N-acyl azolinones as peroxygen bleach activators
JP2001502334A (ja) * 1996-10-15 2001-02-20 ザ、プロクター、エンド、ギャンブル、カンパニー 不斉カチオン性ブリーチアクチベーターおよびそれを用いた組成物
US7179779B1 (en) * 2006-01-06 2007-02-20 North Carolina State University Cationic bleach activator with enhanced hydrolytic stability
CN104557708B (zh) * 2015-01-30 2017-04-26 江南大学 一种一浴合成阳离子漂白活化剂的方法及应用

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