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EP4634265A1 - Polyesters - Google Patents

Polyesters

Info

Publication number
EP4634265A1
EP4634265A1 EP23821983.6A EP23821983A EP4634265A1 EP 4634265 A1 EP4634265 A1 EP 4634265A1 EP 23821983 A EP23821983 A EP 23821983A EP 4634265 A1 EP4634265 A1 EP 4634265A1
Authority
EP
European Patent Office
Prior art keywords
formula
structural units
lll
linear
groups
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
EP23821983.6A
Other languages
German (de)
English (en)
Inventor
Hiroe Yamada
Clemens LIEDEL
Mike SAHL
Xiaoqiang GUO
Juan SARRIA
Rekha Singh
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.)
Clariant International Ltd
Original Assignee
Clariant International Ltd
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 Clariant International Ltd filed Critical Clariant International Ltd
Publication of EP4634265A1 publication Critical patent/EP4634265A1/fr
Pending legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • C08G63/66—Polyesters containing oxygen in the form of ether groups
    • C08G63/668—Polyesters containing oxygen in the form of ether groups derived from polycarboxylic acids and polyhydroxy compounds
    • C08G63/672—Dicarboxylic acids and dihydroxy compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • C08G63/68—Polyesters containing atoms other than carbon, hydrogen and oxygen
    • C08G63/685—Polyesters containing atoms other than carbon, hydrogen and oxygen containing nitrogen
    • C08G63/6854—Polyesters containing atoms other than carbon, hydrogen and oxygen containing nitrogen derived from polycarboxylic acids and polyhydroxy compounds
    • C08G63/6856—Dicarboxylic acids and dihydroxy compounds

Definitions

  • the invention relates to specific polyesters, a process for their preparation, solutions or dispersions comprising such polyesters and solvents, the use of such polyesters as solubilizing agents for cucurbiturils, the use of such polyesters as soil release agents, and detergent compositions comprising such polyesters, surfactants, and water.
  • Cucurbiturils due to their barrel-like structures, are known to bind a number of substances to form host-guest compounds and, for this reason, have high application potential in a number of applications in home care, e.g. for malodor removal.
  • Cucurbiturils made from an industrial process usually contain more than one substance, e.g. a mixture of cucurbit[5]uril, cucurbit[6]uril, cucurbit[7]uril, cucurbit[8]uril.
  • many of these cucurbiturils have very poor water solubilities, e.g. cucurbit[6]uril 18 mg/L in water and cucurbit[8]uril 17 mg/L in water at room temperature (25°C). Due to their poor solubilities, it is difficult to formulate industrial grade cucurbiturils into aqueous formulations to get homogenous compositions, e. g. in the area of consumer care.
  • US 10,881 ,592 B2 discloses a stable suspension composition comprising cucurbituril particles suspended in a medium, wherein the cucurbituril particles have an average particle size of from about 0.25 pm to about 50 pm. It can be used in a few consumer care products in the form of suspensions. However, in many other consumer care products, e.g. laundry detergents, solutions are highly preferred.
  • US 6,869,466 B1 discloses an aqueous solution comprising a solubilizing agent for increasing the solubility of the cucurbituril in the aqueous solution, where the solubilizing agent is selected from the group consisting of metal salts, ammonium salts, acids and polyhydroxylated organic compounds.
  • the solubilizing agent is selected from the group consisting of metal salts, ammonium salts, acids and polyhydroxylated organic compounds.
  • polyesters comprising
  • R 1 is H or SO 3 - 1 / P M p+ , and
  • R 2 is a linear or branched alkylene group represented by the formula (CmH2m), with m being an integer from 2 to 10, and
  • X is N-R 3 or O, preferably N-R 3 ,
  • R 3 is H or an alkyl group represented by the formula (C P H2 P +i), with p being an integer from 1 to 10, more preferably is H or an alkyl group represented by the formula (C P H2 P +i), with p being an integer from 1 to 6, even more preferably is H or an alkyl group represented by the formula (C P H2 P +i), with p being an integer from 1 to 3 and extraordinarily preferably is H or CH3,
  • Y is a linear or branched alkyl group represented by the formula (C q H2q+i), with q being an integer from 1 to 18, or a group of the formulae (111-1 ), (HI-2) or (HI-3),
  • R 4 and R 5 are, independently of one another, H or a linear or branched alkyl group represented by the formula (CrH2r+i), with r being an integer from 1 to 18, preferably a linear or branched alkyl group represented by the formula (CrH2r+i), with r being an integer from 1 to 18, preferably from 1 to 12, more preferably from 1 to 10, and even more preferably from 1 to 8, n is an integer from 1 to 20, preferably from 1 to 12, more preferably from 1 to 6, even more preferably from 2 to 4, particularly preferably is 2 or 3 and extraordinarily preferably is 3,
  • R 7 is an alkyl group containing from 1 to 30 carbon atoms or an alkenyl group containing from 2 to 30 carbon atoms, preferably an alkyl group containing from 1 to 22 carbon atoms or an alkenyl group containing from 2 to 22 carbon atoms, more preferably an alkyl group containing from 1 to 6 carbon atoms or an alkenyl group containing from 2 to 6
  • R 6 is a linear or branched C1-30 alkyl group, preferably a linear or branched C1-4 alkyl group, and more preferably methyl, a, b and c are, based on molar average, a number independently selected from 0 to 200, the sum of a+b+c is from 2 to 500, preferably from 2 to 200 and more preferably from 2 to 150, the [C2H4-O], [C3H6-O] and [C4H8-O] groups of the terminal group of the formula (IV-a) may be arranged blockwise, alternating, periodically and/or statistically, preferably blockwise and/or statistically, and either of the [C2H4- O], [C3H6-O] and [C4H8-O] groups of the terminal group of the formula (IV-a) can be linked to -R 6 and/or -O.
  • a subject matter of the present invention is polyesters comprising
  • R 1 is H or SO3- 1 / P M p+ .
  • R 2 is a linear or branched alkylene group represented by the formula
  • X is N-R 3 or O, preferably N-R 3 ,
  • R 3 is H or an alkyl group represented by the formula (C P H2p+i), with p being an integer from 1 to 10, more preferably is H or an alkyl group represented by the formula (C P H2 P +i), with p being an integer from 1 to 6, even more preferably is H or an alkyl group represented by the formula (C P H2p+i), with p being an integer from 1 to 3 and extraordinarily preferably is H or CH3,
  • Y is a linear or branched alkyl group represented by the formula (C q H2q+i), with q being an integer from 1 to 18, or a group of the formulae (111-1 ), (HI-2) or (HI-3),
  • R 4 and R 5 are, independently of one another, H or a linear or branched alkyl group represented by the formula (C r H2r+i), with r being an integer from 1 to 18, preferably a linear or branched alkyl group represented by the formula (CrH2r+i), with r being an integer from 1 to 18, preferably from 1 to 12, more preferably from 1 to 10, and even more preferably from 1 to 8, n is an integer from 1 to 20, preferably from 1 to 12, more preferably from 1 to 6, even more preferably from 2 to 4, particularly preferably is 2 or 3 and extraordinarily preferably is 3,
  • R 6 is a linear or branched C1-30 alkyl group, preferably a linear or branched C1-4 alkyl group, and more preferably methyl, a, b and c are, based on molar average, a number independently selected from 0 to 200, the sum of a+b+c is from 2 to 500, preferably from 2 to 200 and more preferably from 2 to 150, the [C2H4-O], [C3H6-O] and [C4H8-O] groups of the terminal group of the formula (IV-a) may be arranged blockwise, alternating, periodically and/or statistically, preferably blockwise and/or statistically, and either of the [C2H4- O], [C3H6-O] and [C4H8-O] groups of the terminal group of the formula (IV-a) can be linked to -R 6 and/or -O.
  • polyesters of the invention possess or lead to advantageous solubilizing effects of cucurbiturils in water and thus work as solubilizing agent for cucurbiturils.
  • Solubilizing agent for cucurbiturils as used herein means an agent that enhances the solubility of cucurbiturils, preferably in aqueous compositions and more preferably in aqueous solutions or dispersions.
  • inventive polyesters can enhance the malodor removing effect of cucurbiturils, e.g. of cucurbiturils that are present in aqueous compositions such as in aqueous washing liquors.
  • inventive polyesters additionally e.g. show beneficial compatibility with liquid detergent compositions and detergency enhancement and can act as a soil release agent possessing advantageous soil release performance.
  • inventive polyesters may show beneficial anti-greying effect and malodor removal.
  • Soil release agent as used herein means an agent that enhances soil removal during laundering by modifying the surface of the fabric that is laundered, preferably by increasing the surface polarity.
  • one molecule of the polyesters of the invention comprises two or more of the structural units of the formula (I)
  • the definitions of R 1 and of the cation 1 / P M p+ and the binding positions of the different groups -(CO)- and R 1 relative to each other may vary between those structural units.
  • the one or more structural units of the formula (I) of the polyesters of the invention are preferably derived from aromatic dicarboxylic acids or their salts or their dialkylesters, such as, terephthalic acid, phthalic acid, isophthalic acid, 5- sulfoisophthalic acid, 3-sulfophthalic acid, 4-sulfophthalic acid or their salts or their dialkyl esters, more preferably their (C1-C4)-dialkyl esters and even more preferably their dimethyl esters, or mixtures thereof.
  • R 1 in the one or more structural units of the formula (I) is SOa" 1 / P M p+
  • the cation 1 / P M p+ preferably is Na + .
  • R 1 in the one or more structural units of the formula (I) of the polyesters of the invention is H.
  • the binding positions of the two groups -(CO)- relative to each other is para .
  • the one or more structural units of the formula (I) of the polyesters of the invention are derived from terephthalic acid or its salts or its dialkyl esters, preferably its (C1-C4)-dialkyl esters and more preferably its dimethyl ester, or mixtures thereof.
  • the number of structural units of the formula (I) in the polyesters of the invention is, based on molar average, from 1 to 30, more preferably from 1 .2 to 25, even more preferably from 1 .4 to 20 and particularly preferably from 1 .6 to 15.
  • further structural units derived from other di- or polycarboxylic acids or their salts or their (di)alkylesters can be used in the polyesters of the invention, such as, naphthalene-1 ,4-dicarboxylic acid, naphthalene-2, 6, -dicarboxylic acid, tetrahydrophthalic acid, trimellitic acid (but different to the structural units of the formulae (lll-a) and (lll-b)), diphenoxyethane-4,4'-dicarboxylic acid, diphenyl-4,4'- dicarboxylic acid, 2,5-furandicarboxylic acid, adipic acid, sebacic acid, decan-1 , 10- dicarboxylic acid, fumaric acid, succinic acid, 1 ,4-cyclohexanedicarboxylic acid, cyclohexanediacetic acid, glutaric acid, azelaic acid,
  • one molecule of the polyesters of the invention comprises two or more of the structural units of the formula (II)
  • the definition of R 2 may vary between those structural units.
  • the one or more structural units of the formula (II) of the polyesters of the invention are preferably derived from alkylene glycols.
  • Preferred structural units of the formula (II) are derived from alkylene glycols selected from the group consisting of ethylene glycol, 1 ,2-propyleneglycol, 1 ,3-propyleneglycol, 2-methyl- 1 ,3-propanediol, 1 ,4-butanediol, 1 ,3-butanediol, 2,3-butanediol, 1 ,2-butanediol, 2,2-dimethyl-1 ,3-propanediol, 1 ,2-pentanediol, 1 ,5-pentanediol, 1 ,2-hexanediol, 1 ,6-hexanediol and mixtures thereof.
  • triols or tetraols can be used in the polyesters of the invention, preferably glycerol, pentaerythritol or mixtures thereof.
  • further structural units derived from triols or tetraols would be present to a minor extent, for example in an amount smaller than 5 wt.-% based on the total weight of the polyester of the invention.
  • R 2 in the one or more structural units of the formula (II) of the polyesters of the invention is selected from the group consisting of (C2H4), (C3H6), and mixtures thereof.
  • one molecule of the polyesters of the invention comprises two or more of the structural units of the formula (lll-a) or two or more of the structural units of the formula (lll-b) or two or more of the terminal groups of the formula (lll-c)
  • the definitions of X and Y may vary between those structural units of the formula (lll-a) and between those structural units of the formula (lll-b) and the definition of Y may vary between those terminal groups of the formula (lll-c).
  • one molecule of the polyesters of the invention comprises one or more structural units of the formula (lll-a) and one or more structural units of the formula (lll-b)
  • the definitions of X and Y may vary between those structural units of the formula (lll-a) and (lll-b).
  • one molecule of the polyesters of the invention comprises one or more structural units of the formula (lll-a) and one or more terminal groups of the formula (lll-c) or one or more structural units of the formula (lll-b) and one or more terminal groups of the formula (lll-c)
  • the definition of Y may vary between those structural units of the formula (lll-a) and terminal groups of the formula (lll-c) and between those structural units of the formula (lll-b) and terminal groups of the formula (lll-c).
  • the one or more structural units or terminal groups of the formulae (lll-a), (lll-b) and (lll-c) of the polyesters of the invention may be derived from trimellitic acid, trimellitic anhydride or their derivatives and amines of the formula HNR 3 Y wherein R 3 and Y have the meaning given above, and in particular from trimellitic acid, trimellitic anhydride or their derivatives and amines of the formula HNR 3 (C q H2q+i), HNR 3 (CH2)nNR 4 R 5 or mixtures thereof, in which R 3 , R 4 , R 5 , n and q have the meaning given above, preferably 2-dimethylamino-ethylamine, 2-diethylamino- ethylamine, 2-dipropylamino-ethylamine, 2-dibutylamino-ethylamine, 3- dimethylamino-propylamine, 3-diethylamino-propylamine, 3-diprop
  • the one or more structural units or terminal groups of the formulae (lll-a) and (lll-b) of the polyesters of the invention may be derived from trimellitic acid, trimellitic anhydride or their derivatives and alcohols of the formula HO-Y, in which Y has the meaning given above, and in particular from trimellitic acid, trimellitic anhydride or their derivatives and alcohols of the formula HO(C q H2q+i), HO(CH2)nNR 4 R 5 or mixtures thereof, in which R 4 , R 5 , n and q have the meaning given above, preferably 2-dimethylamino-ethanol, 2-diethylamino-ethanol, 2- dipropylamino-ethanol, 2-dibutylamino-ethanol, 3-dimethylamino-propanol, 3- diethylamino-propanol, 3-dipropylamino-propanol, 3-dibutylamino-propanol, 4- dimethylamino-butan
  • the groups of the formula (HI-1 ) are preferred.
  • one molecule of the polyesters of the invention comprises two or more of the terminal groups of the formula (IV-a)
  • the definitions of R 6 , a, b and c may vary between those terminal groups.
  • the [CAHS-O]-, [C3H6-O]- and [C2H4-O]-groups may be arranged blockwise, alternating, periodically and/or statistically, preferably blockwise and/or statistically.
  • the groups [C4H8-O], [C3H6-O] and [C2H4-O] may be arranged, for example, in a purely statistically or blockwise form but may also be arranged in a form which could be considered as both statistical and blockwise, e.g.
  • both R 6 - and -O may be connected to a [C4H8-O]- group, they may both be connected to a [C3H6-O]-group, they may both be connected to a [C2H4-O]-group or they may be connected to different groups selected from [C4H8-O], [C3H6-O] and [C2H4-O].
  • a in the one or more terminal groups of the formula (IV-a) of the polyesters of the invention is, based on molar average, a number from 0 to 180, more preferably from 2 to 130 and even more preferably from 10 to 100.
  • b in the one or more terminal groups of the formula (IV-a) of the polyesters of the invention is, based on molar average, a number from 0 to 50, more preferably from 0 to 20 and even more preferably b is 0.
  • c in the one or more terminal groups of the formula (IV-a) of the polyesters of the invention is 0.
  • b and c in the one or more terminal groups of the formula (IV-a) of the polyesters of the invention are 0.
  • the polyester of the invention further comprises one or more structural units of the formula (V-a)
  • f in the one or more structural units of the formula (V-a) of the polyesters of the invention is 0.
  • e and f in the one or more structural units of the formula (V-a) of the polyesters of the invention are 0.
  • the groups (C2H4) in the terminal groups of the formula (IV-a) or in the structural units of the formula (V-a) preferably are of the formula -CH2-CH2-.
  • the groups (C3H6) in the terminal groups of the formula (IV-a) or in the structural units of the formula (V-a) preferably are of the formula -CH(CH3)-CH2- or -CH2-CH(CH3)-, i.e. of the formula
  • the groups (C4H8) in the terminal groups of the formula (IV-a) or in the structural units of the formula (V-a) preferably are of the formula -CH(CH3)-CH(CH3)-, i.e. of the formula
  • structural units of the formulae (II) and (V-a) may be linked directly to structural units or terminal groups of the formulae (I), (lll-a), (lll-b) or (lll-c) resulting in ester groups.
  • terminal groups of the formula (IV-a) may be linked directly to structural units of the formulae (I), (lll-a) or (lll-b) also resulting in ester groups.
  • the amount of the one or more terminal groups of the formula (IV-a), based on the total weight of the polyester preferably is at least 40 wt.-%, more preferably from 42 to 90 wt.-% and even more preferably from 45 to 85 wt.-%.
  • the polyester of the invention consists exclusively of the one or more structural units of the formula (I) and the one or more structural units of the formula (II) and the one or more structural units or terminal groups selected from the formulae (lll-a), (lll-b), (lll-c) or mixtures thereof and the one or more terminal groups of the formula (IV-a), and if present, the one or more structural units of the formula (V-a).
  • the polyesters of the invention consist exclusively of the one or more structural units of the formula (I), and the one or more structural units of the formula (II), and the one or more structural units or terminal groups selected from the formulae (lll-a), (lll-b), (lll-c) or mixtures thereof, and the one or more terminal groups of the formula (IV-a).
  • the weight average molecular weight (Mw) of the polyesters of the invention is from 1000 to 20000 g/mol.
  • the weight average molecular weight (Mw) of the polyesters of the invention may be determined by gel permeation chromatography (GPC) analysis, preferably as detailed in the following: 20 pl of sample with a concentration of 1 mg/ml dissolved in tetrahydrofuran (THF)/H2O 80:20 (v:v) is injected onto a PSS Suprema column set of two columns with the dimensions 300 mm length and 8 mm internal diameter (ID) with a porosity of 30 A and particle size 10 pm. The detection is monitored at 235 nm on a multiple wavelength detector.
  • GPC gel permeation chromatography
  • the employed eluent is 1 .25 g/l of disodium hydrogen phosphate dihydrate in a 45 / 55 % (v/v) water / acetonitrile mixture. Separations are conducted at a flow rate of 1 ml/minute at 25 °C. Quantification is performed by externally calibrating standard samples of different molecular weight polyethylene glycols (430 g/mol - 44000 g/mol).
  • the polyesters of the invention comprise one or more terminal groups of the formula (IV-a) and may also comprise one or more terminal groups of the formula (lll-c).
  • the polyesters of the invention may comprise one or more further terminal groups, preferably selected from the group consisting of -OH (this terminal group can e.g. occur in case a structural unit of the formulae (I), (lll-a) or (lll-b) terminates an end of the polyester), -OCH3 (this terminal group can e.g. occur in case a structural unit of the formula (I) terminates an end of the polyester), -OR 2 OH wherein R 2 has the meaning given above (this terminal group can e. g.
  • the [C2H4-O], [C3H6-O] and [C4H8-O] groups may be arranged blockwise, alternating, periodically and/or statistically and either of the [C2H4-O], [C3H6-O] and [C4H8-O] groups can be linked to -O and/or H (this terminal group can e. g. occur in case a structural unit of the formula (V-a) terminates an end of the polyester).
  • the polyesters of the invention comprise, in addition to the one or more terminal groups of the formula (IV-a), one or more terminal groups of the formula (lll-c). In a more preferred embodiment of the invention, all terminal groups of the polyesters of the invention are selected from the group consisting of the terminal groups of the formula (IV-a) and the terminal groups of the formula (lll-c).
  • all terminal groups of the polyesters of the invention are terminal groups of the formula (IV-a).
  • polyesters of the invention typically a two-stage process is used of either direct esterification of dicarboxylic acids and diols or transesterification of (i) diesters of dicarboxylic acids and (ii) diols, followed by a polycondensation reaction under reduced pressure.
  • a further subject matter of the invention is a process for the preparation of the polyesters of the invention comprising the steps of: heating one or more substances of the formula (l-a)
  • Q 1 and Q 2 are, independently of one another, H or (C1-C4)-alkyl and preferably are CH3, and
  • R 1 has the meaning given above, and preferably, the substance of the formula (l-a) is dimethyl terephthalate, and one or more substances of the formula HO-R 2 -OH, wherein R 2 has the meaning given above, and preferably, the one or more substances of the formula HO-R 2 - OH are selected from the group consisting of ethylene glycol, 1 ,2-propyleneglycol, and mixtures thereof, and one or more substances of the formulae (lll-d), (lll-e), (lll-f) or mixtures thereof, wherein
  • Y is a linear or branched alkyl group represented by the formula
  • Q 3 and Q 4 are, independently of one another, H or (C1-C4)-alkyl, preferably H or CH3, and more preferably H, and one or more substances of the formula HO-[C2H4-O] a -[C3H6-O]b-[C4Ha-O]c-R 6 , wherein R 6 , a, b and c have the meaning given above, the [C2H4-O], [C3H6-O] and [C4H8-O] groups may be arranged blockwise, alternating, periodically and/or statistically, preferably blockwise and/or statistically, and either of the [C2H4-O], [C3H6-O] and [C4H8-O] groups can be linked to -R 6 and -OH, and, optionally, one or more substances of the formula HO-[C2H4-O]d-[C3H6-O]e-[C4Ha-O]f-H, wherein d,
  • Typical transesterification and condensation catalysts known in the art can be used for the inventive process for the preparation of the polyesters of the invention, such as antimony, germanium and titanium-based catalysts.
  • tetraisopropyl orthotitanate (IPT) and sodium acetate (NaOAc) are used as the catalyst system in the inventive process for the preparation of the polyesters of the invention.
  • polyesters of the invention that comprise one or more groups of the formula (111-1 ) can e.g. be quaternised by methods well-known to the person skilled in the art in order to obtain the polyesters of the invention that comprise one or more groups of the formula (HI-2), for example with quaternising agents such as dimethylsulfate, or they can be oxidised by methods well-known to the person skilled in the art in order to obtain the polyesters of the invention that comprise one or more groups of the formula (HI-3), for example with oxidising agents such as hydrogen peroxide H2O2.
  • polyesters of the invention are typically prepared by polycondensation processes as described above. This leads to statistically determined mixtures of polyesters in which a mixture of molecular species with a distribution around a molar average is obtained.
  • the raw materials for the preparation of the polyesters according to the invention can be based on fossil carbon or renewable carbon.
  • Renewable carbon includes carbon originating from biomass, carbon capture, or chemical recycling.
  • the raw materials for the preparation of the polyesters according to the invention are at least partly based on renewable carbon.
  • the Renewable Carbon Index (RCI, a measure of sustainability by dividing the number of carbons derived from renewable sources by the total number of carbons in an active ingredient) of the polyesters according to the invention preferably is above 40%, more preferably above 50%, even more preferably above 60%, particularly preferably from 70 to 100% (including 100%), and most preferably 100%.
  • all the -CH2-CH2-O- structural units within terminal groups of the formula (IV-a) and structural units of the formula (V-a), as well as all the -CH2-CH2- O- structural units within structural units of the formula (II), in case these comprise one or more structural units -CH2-CH2-O-, are bio-based, and the polyesters of the invention have a RCI above 40%, preferably from 50 to 95%, and more preferably from 60 to 85%.
  • polyesters of the invention may be used in substance, i.e. as granules, but may also be provided as solutions or dispersions. The latter two exhibit beneficial handling properties and are more easily dosed.
  • a further subject matter of the invention is solutions or dispersions comprising one or more polyesters of the invention and one or more solvents.
  • the one or more solvents contained in the solution or dispersion of the invention are selected from the group consisting of water, ethanol, propanol, butanol, ethylene glycol, 1 ,2-propylene glycol, 1 ,3-propylene glycol, 1 ,2-butylene glycol, 1 ,3-butylene glycol, 1 ,4-butylene glycol, butyl glycol, butyl diglycol, butyl polyglycol, and mixtures thereof.
  • the solution or dispersion of the invention comprises water.
  • the solution or dispersion of the invention comprises water and one or more cucurbiturils.
  • Cucurbiturils are barrel-like molecules which can be prepared according to the process described in US 10,626,119 B2.
  • the solutions or dispersions of the invention comprise water and one or more solvents different from water, preferably selected from the group consisting of ethanol, propanol, butanol, ethylene glycol, 1 ,2-propylene glycol, 1 ,3-propylene glycol, 1 ,2-butylene glycol, 1 ,3-butylene glycol, 1 ,4-butylene glycol, butyl glycol, butyl diglycol, butyl polyglycol, and mixtures thereof.
  • solvents different from water preferably selected from the group consisting of ethanol, propanol, butanol, ethylene glycol, 1 ,2-propylene glycol, 1 ,3-propylene glycol, 1 ,2-butylene glycol, 1 ,3-butylene glycol, 1 ,4-butylene glycol, butyl glycol, butyl diglycol, butyl polyglycol, and mixtures thereof.
  • the solutions or dispersions of the invention comprise water and one or more solvents different from water, preferably selected from the group consisting of ethanol, propanol, butanol, ethylene glycol, 1 ,2-propylene glycol, 1 ,3-propylene glycol, 1 ,2-butylene glycol, 1 ,3-butylene glycol, 1 ,4-butylene glycol, butyl glycol, butyl diglycol, butyl polyglycol, and mixtures thereof, and one or more cucurbiturils.
  • solvents different from water preferably selected from the group consisting of ethanol, propanol, butanol, ethylene glycol, 1 ,2-propylene glycol, 1 ,3-propylene glycol, 1 ,2-butylene glycol, 1 ,3-butylene glycol, 1 ,4-butylene glycol, butyl glycol, butyl diglycol, butyl polyglycol, and mixtures thereof, and one or more
  • the inventive polyesters may advantageously be used as solubilizing agents of cucurbiturils.
  • a further subject matter of the invention is the use of one or more polyesters of the invention as solubilizing agents for cucurbiturils.
  • the inventive polyesters may advantageously be used as soil release agents.
  • a further subject matter of the invention is the use of one or more polyesters of the invention as soil release agents.
  • polyesters of the invention as solubilizing agents for cucurbiturils and/or as soil release agents preferably takes place in consumer products, and more preferably in laundry detergent formulations, fabric conditioners, automatic dishwashing rinse aid formulations, hand dishwashing liquids, air fresheners or hard surface cleaners.
  • the consumer products are detergent compositions.
  • a further subject matter of the invention is a detergent composition, preferably a laundry detergent composition, comprising
  • solutions or dispersions of the invention may e.g. represent liquid handling forms of the polyesters of the invention and may be used for the preparation of the inventive detergent compositions to be used by end consumers.
  • the detergent compositions of the invention and preferably the laundry detergent compositions of the invention additionally comprise one or more cucurbiturils.
  • the detergent compositions of the invention comprise the one or more polyesters of component Z1 ) preferably in an amount of at least 0.1 wt.-%, more preferably in an amount from 0.1 to 10 wt.-%, even more preferably in amount from 0.2 to 5 wt.-% and particularly preferably in an amount from 0.2 to 3 wt.-%, in each case based on the total weight of the detergent composition.
  • the detergent compositions of the invention comprise one or more surfactants as component Z2).
  • the one or more surfactants of component Z2) of the detergent compositions of the invention are selected from the group consisting of anionic, nonionic, cationic and zwitterionic surfactants, and more preferably from the group consisting of anionic, nonionic and zwitterionic surfactants.
  • Suitable anionic surfactants that may be used are any of the conventional anionic surfactant types typically used in detergent products. These include alkyl sulfonates, alkyl ether sulfates, alkyl sulfates, alkyl ester sulfonates and soaps. Preferred anionic surfactants are alkylbenzene sulfonates, alkyl ether sulfates, alkyl sulfates and soaps.
  • Preferred alkyl sulfonates are alkylbenzene sulfonates, particularly linear alkylbenzene sulfonates (LAS) having an alkyl chain length of C8-C15.
  • Possible counter ions for concentrated alkaline liquids are ammonium ions, e.g. those generated by the neutralization of alkylbenzene sulfonic acid with one or more ethanolamines, for example monoethanolamine (MEA) or triethanolamine (TEA), or alternatively, alkali metals, e.g. those arising from the neutralization of alkylbenzene sulfonic acid with alkali hydroxides.
  • the linear alkyl benzene sulfonate surfactants may be LAS with an alkyl chain length of preferably from 8 to 15 and more preferably from 12 to 14.
  • the neutralization of the acid may be performed before its addition to the detergent compositions of the invention or during the process of formulating the detergent compositions of the invention through excess addition of neutralizing agent.
  • Preferred alkyl ether sulfates (AES) are alkyl polyethoxylate sulfate anionic surfactants of the formula
  • R 11 is a saturated or unsaturated alkyl chain having preferably from 10 to 22 carbon atoms, and more preferably from 12 to 16 carbon atoms,
  • M + is a cation which makes the compound water-soluble, preferably an ammonium cation, a substituted ammonium cation, an alkali metal cation, or other material chosen from the list of buffers, and
  • A alkyl sulfates
  • R 12 is a linear or branched alkyl chain having preferably from 8 to 24 carbon atoms, and more preferably from 12 to 18 carbon atoms, and
  • M + is a cation which makes the compound water-soluble, preferably an ammonium cation, a substituted ammonium cation, an alkali metal cation, or other material chosen from the list of buffers.
  • Soaps are preferably fatty acids and more preferably linear saturated or unsaturated fatty acids having from 10 to 18 carbon atoms.
  • Nonionic surfactants include primary and secondary alcohol ethoxylates, preferably C8-C20 aliphatic alcohol ethoxylated with an average of from 1 to 35 moles of ethylene oxide per mole of alcohol, and more preferably the C10-C15 primary and secondary aliphatic alcohols ethoxylated with an average of from 1 to 10 moles of ethylene oxide per mole of alcohol.
  • Nonionic surfactants furthermore include nonylphenol ethoxylates, ethoxylated fatty acid monoethanolamides and fatty acid methyl ester ethoxylates.
  • Non-ethoxylated nonionic surfactants include alkyl polyglycosides, fatty acid monoethanolamides, glycerol monoethers, polyhydroxy amides, polyhydroxy alkyl fatty acid amides or N-acyl N-hydrocarbyl derivatives of glucosamine (“glucamides”) such as N-methyl glucamides. Mixtures of nonionic surfactants may be used.
  • the fatty acid methyl ester ethoxylates are selected from mixtures of fatty acid methyl ester ethoxylates of the formula (XI)
  • R 2 O is selected from the group consisting of linear or branched, preferably linear, saturated alkyl groups with 7 to 29 carbon atoms, linear or branched, preferably linear, mono- or polyunsaturated alkenyl groups with 7 to 29 carbon atoms, and combinations thereof, and xa is selected from integer numbers from 1 to 200, and the average number of (CH 2 CH 2 O)-units of the fatty acid methyl ester ethoxylates of the formula (XI) in the mixture is a number from 5 to 25, preferably from 7 to 13, more preferably from 9 to 11 and even more preferably is 10.
  • R 2 o in the above-mentioned mixtures of fatty acid methyl ester ethoxylates of the formula (XI) is selected from the group consisting of linear or branched, preferably linear, saturated alkyl groups with 7 to 21 carbon atoms, linear or branched, preferably linear, mono- or polyunsaturated alkenyl groups with 7 to 21 carbon atoms, and combinations thereof, more preferably, R 2 o is selected from the group consisting of linear or branched, preferably linear, saturated alkyl groups with 11 to 19 carbon atoms, linear or branched, preferably linear, mono- or polyunsaturated alkenyl groups with 11 to 19 carbon atoms, and combinations thereof, and even more preferably, R 2 o is selected from the group consisting of linear or branched, preferably linear, saturated alkyl groups with 13 to 19 carbon atoms, linear or branched, preferably linear, mono- or polyunsaturated alkenyl groups with 13 to 19 carbon atom
  • xa in the above-mentioned mixtures of fatty acid methyl ester ethoxylates of the formula (XI) is selected from integer numbers from 1 to 150, more preferably from 1 to 100, even more preferably from 1 to 75, particularly preferably from 1 to 50, extraordinarily preferably from 1 to 30 and especially preferably from 1 to 25.
  • the above-mentioned mixtures of fatty acid methyl ester ethoxylates of the formula (XI) comprise components (MEE1) and (MEE2)
  • (MEE2) one or more fatty acid methyl ester ethoxylates of the formula (XI), wherein R20 is selected from the group consisting of linear or branched, preferably linear, saturated alkyl groups with 17 carbon atoms, linear or branched, preferably linear, polyunsaturated alkenyl groups with 17 carbon atoms, and combinations thereof, and the molar ratio of component (MEE1 ) to component (MEE2) is at least 2.2:1 .0.
  • the glucamides are selected from the formula (X) wherein
  • R98 is a linear or branched, preferably a linear, alkyl group having 7 to 21 and preferably 7 to 17 carbon atoms, or a linear or branched, preferably a linear, alkenyl group having one or more double bonds and 7 to 21 , preferably 7 to 17, carbon atoms
  • R99 is a linear or branched, preferably a linear, alkyl group having 1 to 6 carbon atoms, more preferably a methyl, ethyl, propyl or butyl group, and even more preferably a methyl group.
  • R98CO in formula (X) is selected from the group consisting of capryloyl, pelargonoyl, caprinoyl, undecyloyl, lauroyl, tridecyloyl, myristoyl, pentadecyloyl, palmitoyl, margaroyl, stearoyl, myristoleoyl, pamitoleoyl, oleoyl, linolenoyl, and mixtures thereof.
  • R98 is a linear alkyl group having 11 to 13 carbon atoms and R99 is a methyl group, or
  • R98CO derives from coconut oil
  • R99 is a methyl group
  • R98CO derives from sunflower oil
  • R99 is a methyl group.
  • the detergent compositions of the invention contain, based on the total weight of the detergent composition, preferably from 0.2 to 40 wt.-% and more preferably from 1 to 20 wt.-% of a nonionic surfactant, such as alcohol ethoxylate, nonylphenol ethoxylate, fatty acid methyl ester ethoxylate, alkylpolyglycoside, ethoxylated fatty acid monoethanolamide, fatty acid monoethanolamide, polyhydroxy alkyl fatty acid amide or glucamide.
  • a nonionic surfactant such as alcohol ethoxylate, nonylphenol ethoxylate, fatty acid methyl ester ethoxylate, alkylpolyglycoside, ethoxylated fatty acid monoethanolamide, fatty acid monoethanolamide, polyhydroxy alkyl fatty acid amide or glucamide.
  • the detergent compositions of the invention may comprise, based on the total weight of the detergent composition, up to 10 wt.-% of a zwitterionic surfactant, e.g. amine oxide or betaine.
  • a zwitterionic surfactant e.g. amine oxide or betaine.
  • Typical amine oxides used are of the formula
  • R 13 is a long chain moiety and each CH2R 14 is a short chain moiety
  • R 14 is preferably selected from the group consisting of H, CH3 and -CH2OH.
  • R 13 is a primary or branched hydrocarbyl moiety with a chain length of 8 to 18 carbon atoms, which can be saturated or unsaturated.
  • R 13 is a primary alkyl moiety with a chain length of 8 to 18 carbon atoms.
  • Preferred amine oxides have compositions wherein R 13 is a Cs-C-is alkyl and R 14 is H. These amine oxides are e.g. illustrated by C12-14 alkyldimethyl amine oxide, hexadecyl dimethylamine oxide, octadecylamine oxide.
  • a preferred amine oxide material is lauryl dimethylamine oxide, also known as dodecyldimethylamine oxide or DDAO.
  • Betaines may be alkyldimethyl betaines or alkylamido betaines, wherein the alkyl groups have C12-18 chains.
  • the one or more surfactants of component Z2) of the detergent compositions of the invention are selected from the group consisting of linear alkyl benzene sulfonates, alkyl ether sulfates, alkyl sulfates, soaps, nonionic surfactants, amine oxides and betaines, and more preferably the one or more surfactants of component Z2) of the detergent compositions of the invention are selected from the group consisting of linear alkyl benzene sulfonates, alkyl ether sulfates, alkyl sulfates, soaps and nonionic surfactants.
  • the detergent compositions of the invention comprise the one or more surfactants of component Z2) preferably in an amount of at least 3 wt.-%, more preferably in an amount from 3 to 65 wt.-%, even more preferably in an amount from 4 to 60 wt.-% and particularly preferably in an amount from 5 to 55 wt.-%, in each case based on the total weight of the detergent composition.
  • the detergent compositions of the invention comprise water of component Z3) preferably in an amount of at least 10 wt.-%, more preferably in an amount from 25 to 96.9 wt.-%, even more preferably in an amount from 35 to 95.8 wt.-% and particularly preferably in an amount from 42 to 94.8 wt.-%, in each case based on the total weight of the detergent composition.
  • the detergent compositions of the invention may comprise one or more optional ingredients, e.g. they may comprise conventional ingredients commonly used in detergent compositions, preferably laundry detergent compositions.
  • optional ingredients include, but are not limited to builders, bleaching agents, bleach active compounds, bleach activators, bleach catalysts, photobleaches, dye transfer inhibitors, colour protection agents, anti-redeposition agents, dispersing agents, fabric softening and antistatic agents, fluorescent whitening agents, enzymes, enzyme stabilizing agents, foam regulators, defoamers, malodour reducers, preservatives, disinfecting agents, hydrotropes, fibre lubricants, anti-shrinkage agents, buffers, fragrances, processing aids, colorants, dyes, pigments, anticorrosion agents, fillers, stabilizers, solvents different from water and other conventional ingredients for detergent compositions, preferably laundry detergent compositions.
  • This second polymer is preferably a polyalkoxylated polyethyleneimine (EPEI).
  • EPEI polyalkoxylated polyethyleneimine
  • Polyethylene imines are materials composed of ethylene imine units - CH2CH2NH- and, where branched, the hydrogen on the nitrogen is replaced by another chain of ethylene imine units. These polyethyleneimines can be prepared, for example, by polymerizing ethyleneimine in the presence of a catalyst such as carbon dioxide, sodium bisulfite, sulfuric acid, hydrogen peroxide, hydrochloric acid, acetic acid, and the like.
  • the detergent compositions of the invention may comprise other polymeric materials, for example dye transfer inhibition polymers, anti-redeposition polymers and cotton soil release polymers, preferably those based on modified cellulosic materials.
  • the detergent compositions of the invention may further comprise a polymer of polyethylene glycol and vinyl acetate, for example the lightly grafted copolymers described in WO 2007/138054.
  • amphiphilic graft polymers based on water soluble polyalkylene oxides as graft base and side chains formed by polymerisation of a vinyl ester component have the ability to enable reduction of surfactant levels whilst maintaining high levels of oily soil removal.
  • a hydrotrope is a solvent that is neither water nor conventional surfactant that aids the solubilisation of the surfactants and other components, especially polymer and sequestrant, in the liquid to render it isotropic.
  • suitable hydrotropes there may be mentioned as preferred: monopropylene glycol (MPG), glycerol, sodium cumene sulfonate, ethanol, other glycols, e.g. dipropylene glycol, diethers and urea. MPG and glycerol are preferred hydrotropes.
  • one or more enzymes selected from protease, mannanase, pectate lyase, cutinase, lipase, amylase, and cellulase may be present in the detergent compositions of the invention. Less preferred additional enzymes may be selected from esterase, peroxidase and oxidase. The enzymes are preferably present with corresponding enzyme stabilizers.
  • the total enzyme content in the detergent compositions of the invention is preferably from 0 to 5 wt.-%, more preferably from 0.2 to 4 wt.-% and even more preferably from 0.4 to 2 wt.-%, in each case based on the total weight of the detergent composition.
  • Sequestrants are preferably included.
  • Preferred sequestrants include organic phosphonates, alkanehydroxy phosphonates and carboxylates available under the DEQUEST trademark from Thermphos.
  • the preferred sequestrant level is less than 10 wt.-% and preferably less than 5 wt.-%, in each case based on the total weight of the detergent composition of the invention.
  • a particularly preferred sequestrant is HEDP (1-Hydroxyethylidene-1 ,1 ,- diphosphonic acid).
  • DTPMP diethylenetriamine penta(methylene phosphonic acid)
  • Heptasodium DTPMP diethylenetriamine penta(methylene phosphonic acid)
  • buffers are one or more ethanolamines, e.g. monoethanolamine (MEA) or triethanolamine (TEA). They are preferably used in the detergent compositions of the invention at levels of from 1 to 15 wt.-%, based on the total weight of the detergent composition.
  • Other suitable amino alcohol buffer materials may be selected from the group consisting of compounds having a molecular weight above 61 g/mol, which includes MEA.
  • Suitable materials also include, in addition to the already mentioned materials, monoisopropanolamine, diisopropanolamine, triisopropanolamine, monoamino hexanol, 2-[(2-methoxyethyl) methylamino]- ethanol, propanolamine, N-methylethanolamine, diethanolamine, monobutanolamine, isobutanolamine, monopentanolamine, 1 -amino-3-(2- methoxyethoxy)-2-propanol, 2-methyl-4-(methylamino)-2-butanol and mixtures thereof.
  • amino ethanol buffers are alkali hydroxides such as sodium hydroxide or potassium hydroxide.
  • Builders Further washing and cleaning ingredients which may be present in the detergent compositions of the invention include inorganic and/or organic builders in order to reduce the degree of hardness of the water. These builders may be present in the detergent compositions of the invention in amounts of from about 5 to about 80 wt.-%, based on the total weight of the detergent compositions.
  • Inorganic builders include, for example, alkali metal, ammonium and alkanolammonium salts of polyphosphates, silicates, carbonates, sulfates and aluminosilicates.
  • Suitable organic builders include polycarboxyl compounds, for example ether polycarboxylates, ether hydroxypolycarboxylates, copolymers of maleic anhydride with ethylene or vinyl methyl ether, 1 ,3,5-trihydroxybenzene-2,4,6- trisulfonic acid and carboxymethyloxysuccinic acid, the alkali metal, ammonium and substituted ammonium salts of polyacetic acids, such as ethylenediaminetetraacetic acid and nitrilotriacetic acid, and also polycarboxylic acids, for example mellitic acid, succinic acid, oxydisuccinic acid, polymaleic acid, benzene-1 ,3,5-tricarboxylic acid, carboxymethyloxysuccinic acid, and soluble salts thereof.
  • polycarboxyl compounds for example ether polycarboxylates, ether hydroxypolycarboxylates, copolymers of maleic anhydride with ethylene or vinyl methyl
  • citrates for example citric acid and its soluble salts, in particular the sodium salt
  • polycarboxylic acid builders which can also be used in granulated compositions, in particular together with zeolites and/or sheet silicates.
  • Solvents different from water e.g. may preferably be selected from the group consisting of ethanol, monopropylene glycol and glycerol.
  • the detergent compositions of the invention may additionally contain viscosity modifiers, foam boosting agents, preservatives (e.g. bactericides), pH buffering agents, polyelectrolytes, anti-shrinking agents, anti-wrinkle agents, anti-oxidants, sunscreens, anti-corrosion agents, drape imparting agents, anti-static agents and ironing aids.
  • the detergent compositions of the invention may further comprise pearlisers and/or opacifiers or other visual cues and shading dye.
  • the detergent compositions of the invention may be in solid or in liquid form, including a gel form.
  • the detergent compositions of the invention preferably the laundry detergent compositions of the invention, may be packaged as unit doses in a polymeric film soluble in the wash water.
  • the detergent compositions of the invention may be supplied in multidose plastics packs with a top or bottom closure. A dosing measure may be supplied with the pack either as a part of the cap or as an integrated system.
  • TMSA TMSA is solubilized in acetone by stirring in a reaction vessel under a nitrogen stream.
  • 53 g (0.51 mol) of 3-dimethylamino-1 -propylamine is slowly added into the reaction vessel at 20 °C and mixing is continued for 1 hour.
  • reaction temperature is increased to 50 °C for 30 minutes and then increased to reflux temperature for 4 hours.
  • Acetone and water are then distilled off and the precursor precipitates from the system.
  • the precipitated precursor is collected and washed with acetone and dried overnight.
  • TMSA TMSA is solubilized in DMSO by stirring in a reaction vessel under a nitrogen stream.
  • 75 g (0.40 mol) of 3-dibuylamino-propylamine is slowly added into the reaction vessel at 20 °C and mixing is continued for 1 hour.
  • the reaction temperature is increased to 50 °C for 30 minutes then to 80 °C and vacuum is applied.
  • the reaction mixture was further stirred at this temperature for 4 hours.
  • DMSO and water are distilled off and the precursor precipitates from the system. The precipitated precursor is collected and washed with DMSO and dried overnight.
  • Precursor examples 2 and 3 are synthesized according to precursor example 1
  • precursor example 5 is synthesized according to precursor example 4 with monomer type and dosage described in Table 1 .
  • the mixture is heated up to 230°C. At 230°C, the pressure is reduced to 1 mbar over 160 minutes. Once the polycondensation reaction has started, 1 ,2-propylene glycol is distilled out of the system. The mixture is stirred for 4 hours at 230°C and a pressure of 1 mbar. The reaction mixture is cooled down to 140 - 150°C. Vacuum is released with nitrogen and the molten polymer is transferred out of the reactor.
  • Inventive polyester examples 2 to 11 are synthesized according to inventive polyester example 1 with monomer type and dosage described in Table 2.
  • a cucurbituril sample which contains cucurbit[6]uril (50 wt.-%), cucurbit[7]uril (35 wt.-%) and cucurbit[8]uril (10 wt.-%), and inventive polyesters were added to water and stirred at room temperature (25°C) for at least 1 hour.
  • compositions consisting of the cucurbituril sample and water and compositions consisting of the cucurbituril sample, other substances but no inventive polyesters, and water were prepared and used as comparative compositions.
  • An artificial malodor composition was prepared by mixing 10 mg of 2,3-butanedione, 5 mg of octanal, 30 mg of isovaleraldehyde, 300 mg of isovaleric acid and 50 mg of hexanal in 1 L of water.
  • the cucurbituril sample contains cucurbit[6]uril (50 wt.-%), cucurbit[7]uril (35 wt.- %) and cucurbit[8]uril (10 wt.-%).
  • Aqueous cucurbituril compositions A and B are Aqueous cucurbituril compositions A and B:
  • Aqueous cucurbituril compositions A 5 wt.-% of inventive polyesters and 0.5 wt.-% of the cucurbituril sample were mixed in water and stirred to form slightly turbid to clear solutions.
  • Aqueous cucurbituril composition B 0.5 wt.-% of the cucurbituril sample was mixed in water.
  • the mixtures were prepared in headspace vials. The vials were then closed tightly and analyzed.
  • the headspace vials were equilibrated at 60°C for 30 min at the autosampler before the measurement.
  • a gas phase sample of 1000 pL was extracted from the vial and injected into the GC column.
  • Mass detector parameter run in select ion mode. The peak area of each odorant was then integrated and recorded.

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Polyesters Or Polycarbonates (AREA)

Abstract

La présente invention concerne des polyesters comprenant des motifs structuraux, par exemple dérivés A) de certains acides dicarboxyliques aromatiques ou leurs dérivés, et B) de certains alkylène glycols, et C) de substances pouvant, par exemple, être obtenues à partir de la réaction d'acide trimellitique, d'anhydride trimellitique ou de leurs dérivés avec certaines amines ou certains alcools, et D) de certains éthers monoalkyliques de polyalkylène glycol à fonction monohydroxyle. Ces polyesters peuvent par exemple être utilisés en tant qu'agents de solubilisation pour des cucurbituriles, par exemple dans des produits de consommation tels que des compositions de détergent pour lessives et en particulier dans des produits de consommation aqueux tels que des compositions de détergent pour lessives aqueuses.
EP23821983.6A 2022-12-12 2023-12-08 Polyesters Pending EP4634265A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
IN202221071473 2022-12-12
EP23171732 2023-05-04
PCT/EP2023/084969 WO2024126303A1 (fr) 2022-12-12 2023-12-08 Polyesters

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Family Cites Families (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA1049367A (fr) 1974-06-25 1979-02-27 The Procter And Gamble Company Detergents liquides capables de deloger les saletes
US4125370A (en) 1976-06-24 1978-11-14 The Procter & Gamble Company Laundry method imparting soil release properties to laundered fabrics
US4702857A (en) 1984-12-21 1987-10-27 The Procter & Gamble Company Block polyesters and like compounds useful as soil release agents in detergent compositions
US4759876A (en) 1985-03-19 1988-07-26 Colgate-Palmolive Company Stable soil release promoting enzymatic liquid detergent composition
ATE98674T1 (de) 1985-04-15 1994-01-15 Procter & Gamble Stabile fluessige reinigungsmittel.
US4713194A (en) 1986-04-15 1987-12-15 The Procter & Gamble Company Block polyester and like compounds having branched hydrophilic capping groups useful as soil release agents in detergent compositions
US4711730A (en) 1986-04-15 1987-12-08 The Procter & Gamble Company Capped 1,2-propylene terephthalate-polyoxyethylene terephthalate polyesters useful as soil release agents
US6869466B2 (en) 1999-05-07 2005-03-22 Unisearch Limited Cucurbiturils and method for binding gases and volatiles using cucurbiturils
EP2029645B1 (fr) 2006-05-31 2010-07-21 Basf Se Polymères greffés amphiphiles à base d'oxydes de polyalkylène et esters vinyliques
GB2556619B (en) 2016-08-24 2019-01-02 Aqdot Ltd Suspension compositions
EP3543243B1 (fr) 2016-12-22 2022-02-02 Aqdot Limited Procédé de préparation de dérivés de cucurbiturile
EP4073141A1 (fr) * 2019-12-09 2022-10-19 Clariant International Ltd Polyesters

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