WO2010057973A1 - Compositions solides de traitement de surface contenant des phosphonates neutralisés par des amines - Google Patents

Compositions solides de traitement de surface contenant des phosphonates neutralisés par des amines Download PDF

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Publication number
WO2010057973A1
WO2010057973A1 PCT/EP2009/065549 EP2009065549W WO2010057973A1 WO 2010057973 A1 WO2010057973 A1 WO 2010057973A1 EP 2009065549 W EP2009065549 W EP 2009065549W WO 2010057973 A1 WO2010057973 A1 WO 2010057973A1
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WO
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Prior art keywords
phosphonic acid
bis
propyl
amine
methylene phosphonic
Prior art date
Application number
PCT/EP2009/065549
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English (en)
Inventor
Patrick NOTTÉ
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Thermphos Trading Gmbh
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Publication of WO2010057973A1 publication Critical patent/WO2010057973A1/fr

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    • 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
    • C11D3/16—Organic compounds
    • C11D3/36—Organic compounds containing phosphorus
    • C11D3/364—Organic compounds containing phosphorus containing nitrogen
    • 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
    • C11D3/16—Organic compounds
    • C11D3/36—Organic compounds containing phosphorus

Definitions

  • This invention pertains to solid surface treatment compositions comprising surface active agents, selected amine neutralized phosphonates, conventional additives and optional ingredients.
  • the surface treatment compositions herein are suitable for known applications including detergent laundry compositions, dishwashing compositions, textile softening compositions and hard surface cleaners.
  • the surface compositions herein comprise as a major constituent, generally of from 99.9 % to 70 % of a surface-active agent and from 0.1 % to 30 % of an amine neutralized phosphonic acid component.
  • the neutralizing amine radical is represented by a combination of, at least, two structurally different amine species, one being more hydrophobic by at least two HLB units compared to the second more hydrophilic species.
  • US 2007/0015678 describes modified polysaccharide polymers, in particular oxidized polymers containing up to 70 mole % carboxyl groups and up to 20 mole % aldehyde groups.
  • the modified polysaccharides can be used in a variety of applications including water treatment.
  • the modified polysaccharides can also be used in blends with other chemicals including conventional phosphonates.
  • EP 1 090 980 discloses fabric rejuvenating technologies including compositions and methods. Phosphonates are used as builders and as metal sequestrants. 2-Phosphonobutane-l,2,4-tricarboxylic acid is preferred in that respect.
  • EP 1 035 198 teaches the use of phosphonates as builders in detergent tablets. Phosphonates are also used in the tablet coating composition.
  • EP 0 892 039 pertains to liquid cleaning compositions containing a non-ionic surfactant, a polymer, such as a vinyl pyrrolidone homopolymer or copolymer, a polysaccharide, such as a xanthan gum, and an amphoteric surfactant.
  • a non-ionic surfactant such as a vinyl pyrrolidone homopolymer or copolymer
  • a polysaccharide such as a xanthan gum
  • amphoteric surfactant Conventional phosphonates e.g. diethylene triamino penta(methylene phosphonic acid) (DTPMP) can be used as chelating agents.
  • DTPMP diethylene triamino penta(methylene phosphonic acid)
  • EP 0 859 044 concerns liquid hard surface cleaners containing dicapped poly alkoxylene glycols capable of conferring soil removal properties to the surface to which the cleaner has been applied.
  • the cleaner compositions can
  • Oxygen bleach detergent technology/compositions containing heavy metal sequestrants such as phosphonobutane tricarboxylic acid, are described in EP 0 713 910. Bleaching machine dishwashing compositions are illustrated in EP 0 682 105. DTPMP is used as heavy metal ion sequestrant.
  • US 5 414 112 A discloses: N-bis(phosphonomethyl)-L-glutamic acid; -L-serine; and -L- lysine and their use as scale inhibitors in industrial waters.
  • WO 98/30666 A pertains to alkaline detergent containing mixed organic and inorganic sequestrants.
  • the detergents use a mixture of a condensed phosphate and an organic phosphonate sequestrant.
  • the phosphonate sequestrant can be represented by conventional species.
  • EP 0 496 605 A concerns surface treatment solutions and process effective for making semi-conductor surfaces free from metallic impurities.
  • the compositions comprise hydrogen peroxide and water as major constituents and also a phosphonate chelant selected from conventional species.
  • EP 0 001 853 A describes neutral to mildly alkaline detergent compositions based on a particulate alumino silicate builder and a low level of a conventional polyphosphonic acid, preferably ethylene diamine tetramethylene phosphonic acid.
  • EP 0 291 869 A discloses phosphate free detergents, having reduced incrustation tendency, comprising an additive level of an incrustation inhibitor selected from conventional aminoalkylene phosphonic acid and/or a linear polymer/copolymer of acrylic acid, methacrylic acid and/or maleic acid.
  • EP 0 157 605 discloses liquid detergent compositions containing major levels of surfactants, more than about 50 %, and fatty acids, more than about 30 %, in combination with a quasi builder level of a polyphosphonic acid sequestrant.
  • the phosphonic acid can be present as a salt of potassium, ammonium, C2-8 alkanolamine or C2-8 alkylamine or a mixed salt of ammonium, alkaline metal, alkanolamine or alkylamine in combination with an earth alkaline metal.
  • the composition contains up to 10 %, preferably less than 5 % of water.
  • Sequestrants can facilitate stain removal efficacy by sequestering cations e.g. metal ions which can be, and frequently are, bound to greasy stains.
  • sequestrant action is known to be substandard and insufficient because the embedding of the stains to the surface can be based on cations and, in addition, on locked up polymeric, difficultly detachable structures.
  • percent or “%” as used throughout this application stands, unless defined differently, for “percent by weight” or “% by weight”.
  • phosphonic acid and “phosphonate” are used interchangeably depending, of course, upon medium prevailing alkalinity/acidity conditions.
  • ppm stands for "parts per million”.
  • this invention relates to solid surface treatment composition containing surface- active agents, conventional additives and optional ingredients, comprising:
  • X is selected from C1-C200000, preferably C1-C50000, most preferably C1-C2000, linear, branched, cyclic or aromatic hydrocarbon radicals, optionally substituted by one or more Ci -C 12 linear, branched, cyclic or aromatic groups (which radicals and/or which groups can be) optionally substituted by OH, COOH, COOG, F, Br, Cl, I, OG, SO 3 H, SO 3 G and SG moieties; ZPO 3 M 2 ; [V-N(IQ] n -K; [V-N(Y)J n -V or [V-O] x -V; wherein V is selected from: a C2-50 linear, branched, cyclic or aromatic hydrocarbon radical, optionally substituted by one or more C 1-12 linear, branched, cyclic or aromatic groups (which radicals and/or groups are) optionally substituted by OH, COOH, COOR', F/Br/Cl/I, OR
  • Z is a Ci _6 alkylene chain
  • M is H
  • W is selected from H, X and ZPO 3 M 2 ;
  • aminoalkylene phosphonic acid contains, at least, two phosphonic acid groups
  • D is selected from Ci_ioo linear, branched, cyclic or aromatic hydrocarbon chain, optionally substituted by a Ci_i 2 linear, branched, cyclic or aromatic group (which chain and/or which group can be) optionally substituted by SO 3 H,SO 3 J,COOJ,OJ and SJ moieties; or [V-O] x -V wherein V is selected from a C 2 -C50 linear, branched, cyclic or aromatic hydrocarbon radical, optionally substituted by one or more Ci-Ci 2 linear, branched, cyclic or aromatic groups (which radicals and/or groups are) optionally substituted by SO 3 H, SO 3 R' ,COOR' ,OR' or SR' moieties wherein J is selected from Ci- Cioo linear, branched, cyclic or aromatic hydrocarbon radicals, optionally substituted by one or more Ci-Ci 2 linear, branched, cyclic or aromatic groups (which chain and/or group can be ) optionally substitute
  • iii phosphono-alkane-polycarboxylic acid wherein the alkane moiety is a C3_2o linear, branched, cyclic or aromatic hydrocarbon chain and wherein the molar ratio of phosphonic acid radical to carboxylic acid radical is in the range of from 2 : 3 to 1 : 7;
  • linear or branched hydrocarbon chains having from 6 to 2.10 6 carbon atoms containing amino groups substituted by ZPO3M2 , and/or -E-N(W)(Y), with respect to the hydrocarbon chain, in either terminal or branched positions whereby the molar ratio of the aminoalkylene phosphonic acid substituents to the number of carbon atoms in the hydrocarbon chain is in the range of from 2 : 1 to 1 : 40 whereby at least 30 % of the available NH/NH2 functionalities have been converted into the corresponding aminoalkylene phosphonic acid and/or into -E-N(W)(Y) substituted groups and wherein the alkylene moiety is selected from Ci -6 ; wherein E is selected from C1-C2000, preferably C1-C500, most preferably C1-C200, linear, branched, cyclic or aromatic hydrocarbon radicals, optionally substituted by one or more C 1 -C 12 linear, branched, cyclic or aromatic groups (which
  • M is H
  • W is selected from H, E and ZPO 3 M 2 ; preferentially W is ZPO 3 M 2 ;
  • K is ZPO 3 M 2 or H whereby K is ZPO 3 M 2 when W is H or E; with the proviso that the aminoalkylene phosphonic acid contains, at least, two phosphonic acid groups;
  • X is selected from C1-C200000, preferably Ci_soooo, most preferably Ci_2ooo, linear, branched, cyclic or aromatic hydrocarbon radicals, optionally substituted by one or more Ci -C 12 linear, branched, cyclic or aromatic groups (which radicals and/or which groups can be) optionally substituted by OH, COOH, COOG, F, Br, Cl, I, OG, SO 3 H, SO 3 G and SG moieties; H; [V-N(H)J x -H or [V-N(Y)J n -V or [V-O] x -V; wherein V is selected from: a C2-50 linear, branched, cyclic or aromatic hydrocarbon radical, optionally substituted by one or more C 1-12 linear, branched, cyclic or aromatic groups (which radicals and/or groups are) optionally substituted by OH, COOH, COOR', F/Br/Cl/I, OR', SO 3 H
  • W is selected from H and X;
  • the molar ratio of the phosphonic acid multiplied by the number of phosphonic acid moieties in the phosphonic acid to the molar ratio of amine multiplied by the number of N in the amine is from:
  • the amine neutralizing agent is represented by a combination of, at least, two structurally different amine species, the first one being more hydrophobic having a HLB value which is at least 2 units smaller than the HLB value of the second, and the second one being more hydrophilic than the first one, said first and said second amine species being used in equivalent proportions of first (more hydrophobic) : second (more hydrophilic) in the range of from 10 : 3 to 1 : 10.
  • the HLB system and the calculation of the individual HLB values of amine neutralizing species are based on the criteria set forth in:
  • the HLB scale goes from 0 to 20.
  • the HLB value of a compound is derived from the water loving portion of the compound, on a molecular weight basis, and then dividing that number by 5.
  • the amine neutralizing agent is used in neutralizing levels, in relation to the phosphonic acid component, thereby considering the required pH of the detergent formulation, including the type of phosphonate. It goes without saying that detergent co -neutralizing agents such as alkaline and alkaline-earth metal hydroxides can be used.
  • the degree of neutralizing activity of the essential amine component, in relation to the phosphonic acid group can be expressed by means of the pH of a 1% aqueous solution, 20 0 C, of the neutralized product. For amino alkylene phosphonic acids and also for the aminophosphonates in the meaning of iv, this value is at least 1, preferably from 1.5 to 10, in one particular execution from 2 to 8.
  • alkylene phosphonic acids and for the phosphonoalkane polycarboxylic acids this value is at least 2, preferably from 3 to 8.5, and in one particular execution from 3.5 to 8.0.
  • the amine-neutralized phosphonate component can also be prepared individually and as such i.e. as a solution or as a solid added to the claimed arrangement.
  • the phosphonic acid neutralizing adjustments which can be required are routine measures well known in the domain of the art.
  • the first and second amine species are preferably used in equivalent ratios (more hydrophobic : more hydrophilic) of from:
  • equivalent ratio represents the number of moles of the more hydrophobic amine multiplied by the number of amino groups present in that molecule divided by the number of moles of the more hydrophilic amine multiplied by the number of amino groups present in that molecule.
  • Alkylene amines, alkylamines and arylamines used in combination with the second species, in the ponderal proportions set forth above, are more hydrophobic, in the meaning of the invention herein, than species from the group of alkoxyamines and alkanolamines.
  • the first, more hydrophobic, amine neutralizing species has a HLB value which is, at least, 4 units, smaller than the HLB value of the second more hydrophilic species.
  • the HLB value of the first (more hydrophobic) species is smaller than 6.
  • the HLB values of mixtures of either one the first of the second species can be determined in accordance with the UNIQUEMA paper.
  • the iii phosphonocarboxylic acid is preferably represented by 2-phosphonobutane 1,2,4- tricarboxylic acid.
  • the ii alkylene phosphonic acid can, in one preference, be represented by species of the formula 1-hydroxyalkylene 1,1-diphosphonic acid wherein the alkyl group is selected from C 2-10 , more preferably C 2-6 , in one particular execution 1- hydroxy ethylene 1,1-diphosphonic acid.
  • D in the ii alkylenephosphonic acid is [V-O] x -V with V being C 2-10 and with x being from 1-50.
  • X or Y are different from ZPO3M2 when W is ZPO 3 M 2 .
  • W and K are ZPO3M2 when X is [V-O] x -V.
  • z is equal to or smaller than half the number of carbon atoms in X.
  • W and Y are [V- N(BQ] x -K or [V-N(Y)] n -V when X is a Ci to C 50 alkyl chain substituted by COOH, COOG, SO 3 H, SO 3 G, OG, SG, OH, F, Br, Cl or I groups.
  • the i and iv aminoalkylene phosphonic acid group can preferably be selected from the group of: ethylene diamine tetra(methylene phosphonic acid); diethylenetriamine penta(methylene phosphonic acid); 1,3-propane diamine-N,N'-bis(2- aminoethyl)hexa(methylene phosphonic acid); L-lysine-N,N,N',N'-tetra(methylene phosphonic acid); L-alanine di(methylene phosphonic acid); poly((propyl or ethyl) imino bis(methylene phosphonic acid)) substituted polyethylene imine; glycine N,N-bis(propyl or ethyl imino bis(methylene phosphonic acid)); alanine N,N-bis(propyl or ethyl imino bis(methylene phosphonic acid)); ⁇ -alanine N,N-bis(propyl or ethyl imino bis
  • preferred i and iv aminoalkylene phosphonic acid groups can be selected from the group of: 4-amino butanoic acid N,N-bis(propyl or ethyl imino bis(methylene phosphonic acid)); methionine N,N-bis(propyl or ethyl imino bis(methylene phosphonic acid)); L-lysine N,N,N',N'-tetra(propyl or ethyl imino bis(methylene phosphonic acid)); aspartic acid N,N-bis(propyl or ethyl imino bis(methylene phosphonic acid)); phenylalanine N,N-bis(propyl or ethyl imino bis(methylene phosphonic acid)); threonine N,N-bis(propyl or ethyl imino bis(methylene phosphonic acid)); 2-ethanol amine N,N-bis(propyl or ethyl imin
  • the essential amine component needed to neutralize the phosphonic acids can be represented by a wide variety of known species.
  • preferred amines include: alkylene amines; alkoxy amines; halogen substituted alkyl amines; aryl amines; and alkanol amines. It is understood that poly species are embraced.
  • alkyl amines also includes -polyalkyl amines-, -alkyl polyamines- and -polyalkyl polyamines-.
  • amines of interest include: ethylene diamine; diethylene triamine; triethylene tetramine; tetraethylene pentamine; hexamethylene diamine; dihexamethylene triamine; 1,3-propane diamine N,N'-bis (2-amino ethyl); polyether amine; polyether polyamines; amine and poly amine alkoxylates or polyalkoxylates like cocodiamine ethoxylate; 2-chloroethyl amine; 3-chloropropyl amine; 4-chlorobutyl amine; primary, secondary and tertiary amines, and the corresponding poly-amines with C1-C50 linear or branched or cyclic hydrocarbon chains, in particular morpholine, n-butylamine; isopropyl amine; diisopropyl amine; di-n-butylamine; tri-n-butylamine; tri-isobutyl amine; cyclohexy
  • Aromatic amines can be represented by aniline; diaminotoluenes; diphenylalanine; N-phenylbenzamine.
  • Commercially available fatty amines with a chain length from C 6 -C 22 such as hydrogenated tallow alkyl amine; cocoalkyl amine and soyaalkylamine are also examples of preferred species.
  • the treatment compositions can be used, in a conventional manner, for application in relation to all kind of surfaces.
  • the like applications can be represented by: textile laundry; textile softening, textile bleaching; hard surface treatment; dishwasher use; glass and other surface treatment/cleaning applications well known in the domain of the technology.
  • the treatment compositions herein comprise, as a major constituent, of from 99.9% to 70% of a surface active agent; and from 0.1% to 30% of a selected amine neutralized phosphonic acid
  • the treatment compositions of this invention frequently contain, expressed in relation to the total composition, surfactant ingredients in the range of from 2 to 50 %, more preferably of from 2 to 40 % in specific executions from 3 to 15%.
  • the phosphonate ingredient herein can be used, in the actual treatment compositions, in sub additive levels in the range of from 0.001 to 5 %, preferably from 0.002 to 3 %.
  • the phosphonate exhibits, within the context of the actual treatment composition, conventional phosphonate functionalities such as chelant, sequestrant, threshold scale inhibition, dispersant and oxygen bleach analogous properties.
  • the essential phosphonate can provide, in part due to its structural particularities in combination with the amine neutralizing properties, additional synergistic functionalities in relation to e.g.
  • the essential phosphonate amine salt was also found to seek the promiscuity of hydrophobic concentrations/stains in the laundry liquor thereby providing desirable performance benefits non achievable by means of art technologies.
  • the binary amine phosphonate salt also, quite unexpectedly and against expectations, reinforces the effectiveness of bleach analogous performance during the laundry operation.
  • the inventive compositions are particularly beneficial in relation to greasy stains which are known to be particularly stubborn and adversely resistant to, for example, actual liquid treatment technology.
  • the essential phosphonate constituent very importantly, can greatly facilitate the environmental and regulatory acceptability of the cleaning compositions herein.
  • the treatment compositions herein can also comprise conventional additives and optional components which are used in art established levels and for their known functionalities.
  • the surface active agents herein can be represented by conventional species selected from e.g. cationic, anionic, non-ionic, ampholytic and zwitterionic surfactants and mixtures thereof. Typical examples of the like conventional detergent components are eminently well known and have been used extensively.
  • Useful surfactants include C 11-20 alkyl benzene sulfonates, Cio-20 alkyl sulfates, C12-20 alkyl alkoxy sulfates containing e.g. 1-6 ethoxy groups and Cio- 2 0 soaps.
  • Suitable non-ionic surfactants can also be represented by amine oxides having the formula R,R',R"N ⁇ O wherein R, R' R" can be alkyl having from 10 to 18 carbon atoms.
  • Cationic surfactants include quaternary ammonium surfactants such as C 6-16 N-alkyl or alkenyl ammonium surfactants.
  • Nonionic surfactant low foaming
  • Suitable examples of amine combinations for use in the illustrated treatment compositions are listed hereinafter.

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  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Detergent Compositions (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)

Abstract

La présente invention concerne des compositions solides de traitement de surface contenant des phosphonates neutralisés par des amines, des tensioactifs, des additifs classiques et des ingrédients facultatifs. L'agent de neutralisation à base d'amines est représenté par un système binaire d'une ou plusieurs espèces hydrophobes et une ou plusieurs espèces hydrophiles, lesquelles espèces sont employées dans des proportions sélectionnées.
PCT/EP2009/065549 2008-11-21 2009-11-20 Compositions solides de traitement de surface contenant des phosphonates neutralisés par des amines WO2010057973A1 (fr)

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EP08169652.8 2008-11-21
EP08169652 2008-11-21

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2015193203A1 (fr) * 2014-06-19 2015-12-23 Unilever Plc Compositions de traitement des taches
CN111615550A (zh) * 2017-10-06 2020-09-01 卡斯特罗尔有限公司 金属加工流体添加剂组合物

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4129515A (en) * 1976-09-13 1978-12-12 The Procter & Gamble Company Heavy-duty liquid detergent and process
EP0517605A1 (fr) * 1991-06-05 1992-12-09 Nln Composition détergente liquide concentrée contenant un agent séquestrant de type polyphosphonate
WO1996012000A1 (fr) * 1994-10-13 1996-04-25 The Procter & Gamble Company Composition detergente contenant des amines et des tensioactifs anioniques
US5929022A (en) * 1996-08-01 1999-07-27 The Procter & Gamble Company Detergent compositions containing amine and specially selected perfumes
EP1932850A1 (fr) * 2006-12-11 2008-06-18 Thermphos Trading GmbH Composés de phosphonate

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4129515A (en) * 1976-09-13 1978-12-12 The Procter & Gamble Company Heavy-duty liquid detergent and process
EP0517605A1 (fr) * 1991-06-05 1992-12-09 Nln Composition détergente liquide concentrée contenant un agent séquestrant de type polyphosphonate
WO1996012000A1 (fr) * 1994-10-13 1996-04-25 The Procter & Gamble Company Composition detergente contenant des amines et des tensioactifs anioniques
US5929022A (en) * 1996-08-01 1999-07-27 The Procter & Gamble Company Detergent compositions containing amine and specially selected perfumes
EP1932850A1 (fr) * 2006-12-11 2008-06-18 Thermphos Trading GmbH Composés de phosphonate

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2015193203A1 (fr) * 2014-06-19 2015-12-23 Unilever Plc Compositions de traitement des taches
CN106661519A (zh) * 2014-06-19 2017-05-10 荷兰联合利华有限公司 污物处理组合物
CN111615550A (zh) * 2017-10-06 2020-09-01 卡斯特罗尔有限公司 金属加工流体添加剂组合物
CN111615550B (zh) * 2017-10-06 2022-11-01 卡斯特罗尔有限公司 金属加工流体添加剂组合物
US11499118B2 (en) 2017-10-06 2022-11-15 Castrol Limited Metal working fluid additive composition
US11952552B2 (en) 2017-10-06 2024-04-09 Castrol Limited Metal working fluid additive composition

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