WO2010057976A1 - Compositions liquides de traitement de surface contenant des dérivés d'acide phosphonique neutralisés par un système binaire d’amines - Google Patents

Compositions liquides de traitement de surface contenant des dérivés d'acide phosphonique neutralisés par un système binaire d’amines Download PDF

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Publication number
WO2010057976A1
WO2010057976A1 PCT/EP2009/065553 EP2009065553W WO2010057976A1 WO 2010057976 A1 WO2010057976 A1 WO 2010057976A1 EP 2009065553 W EP2009065553 W EP 2009065553W WO 2010057976 A1 WO2010057976 A1 WO 2010057976A1
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WO
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Prior art keywords
phosphonic acid
bis
propyl
amine
methylene phosphonic
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Application number
PCT/EP2009/065553
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English (en)
Inventor
Patrick NOTTÉ
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Thermphos Trading Gmbh
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Publication of WO2010057976A1 publication Critical patent/WO2010057976A1/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
    • 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

Definitions

  • This invention pertains to liquid treatment compositions containing surface-active agents, conventional additives and optional components comprising a surface-active agent and an amine neutralized phosphonic acid compound.
  • the treatment compositions herein comprise a major level of surface-active agent and a relatively minor level of an amine neutralized phosphonic acid.
  • the liquid compositions herein comprise, at least 10 % of water.
  • the surfactant component can be represented by known surfactants including non- ionic, anionic, amphotheric, zwitterionic and cationic species.
  • the phosphonic acid group can be represented by specific aminoalkylene phosphonic acids, narrowly defined alkylene phosphonic acid species and by phosphono-alkane-polycarboxylic acids.
  • the amine neutralizing agent is represented by a combination of, at least, two structurally different amine species, one more hydrophobic species and one more hydrophilic species.
  • US 3,527,608 describes a bottle washing process based on conventional alkaline cleansers complemented by a liquid non-ionic detergent/foam depressant concentrate and also water- soluble organic acids which are capable of forming complexes with hardness causing agents.
  • suitable hardness sequestrants are represented by conventional phosphonates such as amino tri(methylene phosphonic acid) and ethylene diamino tetra(methylene phosphonic acid).
  • EP 0 517 605 discloses liquid detergent compositions containing major levels of anionic and non- ionic surfactants and a saturated fatty acid salt whereby the anionic and fatty acid species are neutralized in situ with amines and from 0.5 to 6 % of a polyphosphonate sequestrant salt.
  • the amine salts can be represented by C2-8 alkanolamines or C2-8 alkaneamines.
  • FR 2 677 370 concerns sequestrants suitable for use in liquid detergents containing at least 20 % of water.
  • the sequestrant can be represented by a mixed salt of: an earth-alkaline metal; an alkali metal, ammonium, alkanolamine or alkane amine of hydroxyethane 1,1- diphosphonic acid.
  • US 4,717,507 pertains to liquid builder- free detergent concentrates having fabric-softening properties containing alkyl benzene sulfonates, ethoxylated non- ionics, water-soluble soaps, fatty acid amide, sequestrants, alcohols and water.
  • the sequestrants can be represented by polyphosphonic acids such as amino tri(methylene phosphonic acid), ethylene diamine tetra(methylene phosphonic acid)and diethylene triamine penta(methylene phosphonic 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.
  • An additional important object of the invention aims at using functionality enhancers, i.e. a binary amine system, to thus promote guiding the phosphonic component towards hydrophobic concentrations/stains and also at using such a binary amine system for increasing the effectiveness of the bleach analogous performance in the laundry liquor.
  • functionality enhancers i.e. a binary amine system
  • percent or “%” as used throughout this application stands, unless defined differently, for “percent by weight” or “% by weight”.
  • phosphonic acid and “phosphonate” are also used interchangeably depending, of course, upon medium prevailing alkalinity/acidity conditions.
  • ppm stands for "parts per million”.
  • liquid surface treatment composition comprising a major level of a surface active agent in combination with an amine neutralized phosphonic acid component.
  • this invention relates to liquid 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 - A -
  • V is selected from: a C2-50 linear, branched, cyclic or aromatic hydrocarbon radical, optionally substituted by one or more Ci_i 2 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, SO 3 R' or SR' moieties; wherein R' is a Ci_i 2 linear, branched, cyclic or aromatic hydrocarbon radical, wherein G is selected from C1-C200000, preferably C1-C50000, most preferably C1-C2000, linear, branche
  • 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 C2-C50 linear, branched, cyclic or aromatic hydrocarbon radical, optionally substituted by one or more C 1 -C 12 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 C 1 - Cioo linear, branched, cyclic or aromatic hydrocarbon radicals, optionally substituted by one or more C 1 -C 12 linear, branched, cyclic or aromatic groups (which chain and/or group can be )
  • iii phosphono-alkane-polycarboxylic acid wherein the alkane moiety is a C 3 _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 ZPO 3 M 2 , 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/NH 2 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 C1-C12 linear, branched, cyclic or aromatic groups (which radical
  • 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;
  • aminoalkylene phosphonic acid contains, at least, two phosphonic acid groups
  • X is selected from Ci-C 2 ooooo, preferably Ci_soooo, most preferably Ci_ 2 ooo, linear, branched, cyclic or aromatic hydrocarbon radicals, optionally substituted by one or more Ci-Ci 2 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)] X -H or [V-N(Y)] n -V or [V-O] x -V; wherein V is selected from: a C 2-50 linear, branched, cyclic or aromatic hydrocarbon radical, optionally substituted by one or more Ci_i 2 linear, branched, cyclic or aromatic groups (which radicals and/or groups are) optionally substituted by OH, COOH, COOR', F/Br/Cl/I, OR',
  • W is selected from H and X; whereby 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 ratios of first (more hydrophobic) : second (more hydrophilic) in the range of from 10 : 1 to 4 : 7 ; and
  • 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 its molecular weight 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 at 20 °C of the neutralized product. For an amino alkylene phosphonic acid and also for an aminophosphonate in the meaning of iv, this value is at least 1, preferably from 1.5 to 8.5, in one particular execution from 2 to 8.
  • the pH of a 1 % aqueous solution at 20°C of the neutralized phosphonate being 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 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 or of either one of the first or 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- hydroxyethylene 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(K)] X -K or [V-N(Y)J 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-N,N- di(methylene phosphonic acid); poly((propyl or ethyl) imino bis(methylene phosphonic acid)) substituted polyethylene imine; glycine N 5 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 ethy
  • 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 imino bis
  • 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; 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 89.6% to 58% of a surface active agent; from 0.4% to 32% of a selected amine neutralized phosphonic acid; and at least 10 % of water, although mixtures of water and suitable well known solvents including aliphatic alcohols can preferably be used.
  • the water can represents at least 20 % and can be used together with up to 20 % of a solvent selected from C 1-10 aliphatic alcohol, monopropylene glycol, ethers of glycol e.g. ethylene glycol and butylglycol, benzyl alcohol and mixtures thereof.
  • the aliphatic alcohol is represented by C2-4 species and is used in levels of about 10 %.
  • 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 C 10-20 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.
  • Treatment compositions generally are well known and have found commercial application for a long time. The ingredients of such compositions are eminently well known, including quantitative and qualitative parameters. We wish to exemplify, in a summary manner, some of the matrixes of treatment compositions to which the essential phosphonate ingredient can be added.

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  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
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  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
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Abstract

La présente invention concerne des compositions liquides de traitement de surface contenant un tensioactif, un acide phosphonique neutralisé par des amines et de l'eau. L'agent de neutralisation à base d'amines est représenté par une combinaison de deux espèces d'amines structuralement différentes, une première espèce plus hydrophobe et une deuxième espèce plus hydrophile, ayant des valeurs de balance hydrophile-lipophile (HLB) distinctes. La valeur HLB de l'espèce hydrophobe est inférieure de plusieurs unités sur l'échelle HLB à la valeur HLB de l'espèce hydrophile. Les compositions se révèlent particulièrement bénéfiques pour éliminer des taches de graisse tenaces.
PCT/EP2009/065553 2008-11-21 2009-11-20 Compositions liquides de traitement de surface contenant des dérivés d'acide phosphonique neutralisés par un système binaire d’amines WO2010057976A1 (fr)

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EP08169651 2008-11-21
EP08169651.0 2008-11-21

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Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102517589A (zh) * 2011-12-29 2012-06-27 广东电网公司电力科学研究院 一种成膜缓蚀剂及其制备方法
JP2015206021A (ja) * 2014-04-23 2015-11-19 花王株式会社 硬質表面用洗浄剤組成物
CN105154269A (zh) * 2015-09-11 2015-12-16 中国石油大学(华东) 一种油类污物清洗剂及制备方法
CN105419972A (zh) * 2015-12-24 2016-03-23 东莞市安美润滑科技有限公司 一种高洁净度抗腐蚀水基光学玻璃清洗剂及其使用方法
WO2017011736A1 (fr) * 2015-07-16 2017-01-19 The Procter & Gamble Company Compositions de nettoyage contenant une amine cyclique et un parfum encapsulé
WO2017011733A1 (fr) * 2015-07-16 2017-01-19 The Procter & Gamble Company Compositions de nettoyage contenant une amine cyclique et un agent d'ombrage des tissus et/ou un azurant optique
WO2017011735A1 (fr) * 2015-07-16 2017-01-19 The Procter & Gamble Company Compositions de nettoyage contenant une amine cyclique et une silicone
WO2021052768A1 (fr) * 2019-09-17 2021-03-25 Zschimmer & Schwarz Mohsdorf GmbH & Co. KG Dérivés d'acide phosphonique et leur procédé de préparation

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 (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102517589A (zh) * 2011-12-29 2012-06-27 广东电网公司电力科学研究院 一种成膜缓蚀剂及其制备方法
JP2015206021A (ja) * 2014-04-23 2015-11-19 花王株式会社 硬質表面用洗浄剤組成物
WO2017011736A1 (fr) * 2015-07-16 2017-01-19 The Procter & Gamble Company Compositions de nettoyage contenant une amine cyclique et un parfum encapsulé
WO2017011733A1 (fr) * 2015-07-16 2017-01-19 The Procter & Gamble Company Compositions de nettoyage contenant une amine cyclique et un agent d'ombrage des tissus et/ou un azurant optique
WO2017011735A1 (fr) * 2015-07-16 2017-01-19 The Procter & Gamble Company Compositions de nettoyage contenant une amine cyclique et une silicone
CN105154269A (zh) * 2015-09-11 2015-12-16 中国石油大学(华东) 一种油类污物清洗剂及制备方法
CN105419972A (zh) * 2015-12-24 2016-03-23 东莞市安美润滑科技有限公司 一种高洁净度抗腐蚀水基光学玻璃清洗剂及其使用方法
WO2021052768A1 (fr) * 2019-09-17 2021-03-25 Zschimmer & Schwarz Mohsdorf GmbH & Co. KG Dérivés d'acide phosphonique et leur procédé de préparation

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