WO2018065177A1 - Composition de détergent à lessive contenant un polymère amphotère - Google Patents
Composition de détergent à lessive contenant un polymère amphotère Download PDFInfo
- Publication number
- WO2018065177A1 WO2018065177A1 PCT/EP2017/072863 EP2017072863W WO2018065177A1 WO 2018065177 A1 WO2018065177 A1 WO 2018065177A1 EP 2017072863 W EP2017072863 W EP 2017072863W WO 2018065177 A1 WO2018065177 A1 WO 2018065177A1
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- WIPO (PCT)
- Prior art keywords
- detergent composition
- laundry detergent
- amphoteric polymer
- composition according
- polymer
- Prior art date
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/16—Organic compounds
- C11D3/37—Polymers
- C11D3/3796—Amphoteric polymers or zwitterionic polymers
-
- 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
- C11D3/0005—Other compounding ingredients characterised by their effect
- C11D3/0036—Soil deposition preventing compositions; Antiredeposition agents
Definitions
- the present invention relates to a solid laundry detergent composition for improved grease cleaning.
- the laundry detergent composition is particularly effective in removing greasy stains from fabrics and enhancing oil repellency of fabrics.
- the solid laundry detergent composition of the present invention contains an amphoteric polymer in the form of a polybetaine-type polymer.
- washing with ordinary detergents often does not remove these stains adequately, because the active ingredients are diluted in the wash rather than being concentrated at or near the stained portions. Furthermore, ordinary detergents do not effectively tackle redeposition of grease onto the fabric during washing.
- Laundry detergent compositions which are specifically designed for removing greasy stains from fabrics have been described in the art.
- US 2015/0267147 AA (Henkel) , for instance, describes a laundry detergent composition that contain porous polyamide particles having an oil absorption capacity of at least 60 g/100 g for removing greasy stains from textiles .
- US 2001/0014658 AA (Ecolab) describes a process for removing hydrophobic and particulate soil from laundry items, the process comprising the steps of: (a) contacting a soiled laundry item with an aqueous treatment comprising an effective treating amount of a hydrophobic ethoxylate surfactant composition; and (b) laundering the treated laundry item with a conventional aqueous laundry detergent.
- Polybetaines are amphoteric polymers in which pendant groups have betaine-type structure.
- the cationic-anionic inner-salt pendant of polybetaines comprises a positively charged ion in the form of a quaternary ammonium ion and a negative species that is separated from the positively charged ammonium group by an alkyl spacer. Examples of such negatively charged species include carboxylates, phosphonates and sulfonates. Therefore, polybetaines can be divided into
- polycarboxybetaines polyphosphobetaines and polysulfobetaines, respectively.
- US 2006/0217286 AA (Rhoda Chimie) describes a composition for the cleaning or the rinsing of hard surfaces comprising at least one surface-active agent and at least one polybetaine (B).
- JP 10-195498 A (Lion Corp, 1998) describes a liquid detergent composition with solid granules dispersed therein, said composition further comprises a dispersion stabilizer in the form of a cationic high molecular compound and an amphoteric polymer compound.
- a dispersion stabilizer in the form of a cationic high molecular compound and an amphoteric polymer compound.
- N-methacryloylethyl-N,N- dimethylammonium-a-N-methylcarboxybetaine- based polymer is mentioned as an example of a suitable amphoteric polymer.
- JP 1 1 -335239 A (Lion Corp, 1999) describes a stain remover composition
- a stain remover composition comprising (A) an amphoteric polymer and/or a cationic polymer compound and (B) benzyl alcohol and/or N-methylpyrrolidone, said composition having pH of 3.0 to 9.0.
- N- methacryloylethyl N,N-dimethylammonium-a-N- methylcarboxybetaine-butyl methacrylate copolymer is mentioned as an example of a suitable amphoteric polymer.
- the present inventors have developed a solid laundry detergent composition that is particularly effective in removing greasy stains from fabrics and in enhancing the oil repellency of fabrics.
- the detergent composition of the present invention is particularly effective in removing greasy stains from fabrics and in enhancing the oil repellency of fabrics.
- amphoteric polymer having molecular weight of at least 5,000 Da, said amphoteric polymer further being characterized in that least 30% of the monomeric units of the amphoteric polymer are betaine units represented by the following formula (I):
- H 2 C C(R 1 )-C(0)0-(CH2)n-N + (R 2 )(R 3 )-(CH 2 )p-X (I)
- R 1 represents a hydrogen atom or a linear or branched C1-C6 alkyl group
- R 2 and R 3 independently of each other, represent an alkyl, hydroxyalkyl or
- aminoalkyl group in which the alkyl group is a linear or branched C1-C6 alkyl
- n is an integer in the range of 1 to 4.
- ⁇ p is an integer in the range of 2 to 8;
- the amphoteric polymer can be used to significantly enhance the oil repellency of fabrics.
- the amphoteric polymer can be used in a post wash composition or in the form of a main wash composition to reduce the extent of redeposition of grease and to enhance future removal of greasy stains.
- Greasy stains generally have a tendency to redeposit on the fabrics during the wash cycle.
- the inventors do not wish to be bound by theory, it is believed that when a stained fabric is brought into contact with an aqueous medium containing the amphoteric polymer, the polymer attaches itself to the fabric, thereby enhancing the oleophobicity (i.e., oil repelling property) of the fabric.
- the improved oil repellency is hypothesized to be due to the superhydrophilic nature of the amphoteric polymers, which adsorb a thin monolayer of moisture on the surface of the fabric, thereby rendering the fabric oil repellent.
- the invention relates to a solid laundry detergent composition containing 0.1 to 20 wt.% of an amphoteric polymer having molecular weight of at least 5,000 Da, said amphoteric polymer further being characterized in that least 30%, preferably at least 50%, of the monomeric units of the amphoteric polymer are betaine units represented by the following formula (I):
- H 2 C C(R 1 )-C(0)0-(CH 2 )n-N + (R 2 )(R 3 )-(CH 2 )p-X
- R 1 represents a hydrogen atom or a linear or branched Ci to C6 alkyl group
- R 2 and R 3 independently of each other, represent an alkyl, hydroxyalkyl or
- alkyl group in which the alkyl group is a linear or branched Ci to C6 alkyl
- laundry detergent composition refers to a composition that can be used to remove or to aid the removal of stains from fabric.
- laundry detergent compositions include detergent compositions that are used in the washing or laundry and ancillary detergent compositions that are used to treat fabrics so as to enhance the stain releasing behaviour of the fabrics during a subsequent wash. It is colloquially referred to as Next-Time-Cleaning-Benefits.
- amphoteric polymer as used herein, unless indicated otherwise,
- amphoteric homopolymers encompasses both amphoteric homopolymers and amphoteric copolymers.
- the laundry detergent composition according to the present invention is very effective in removing greasy stains from fabrics and it further improves the tendency of the washed fabrics to easily release such greasy stains by enhancing the oil repellency of the fabric.
- greasy stains refers to stains comprising hydropbobic material such as fats, oils, waxes and mineral oil.
- the solid laundry detergent composition of the present invention preferably is a powder (e.g. a granulate) or a shaped solid article, e.g. a bar or cake which could be a soap- based composition or a composition based on non-soap surfactants like linear alkyl benzene sulphonates.
- the amphoteric polymer is preferably introduced in the detergent composition in the form of polymer-containing particles that contain 30 to 95 wt.% of carrier material and at least 0.3 wt.% of the amphoteric polymer. More preferably, these polymer-containing particles contain 10 to 50 wt.% of carrier material and at least 0.5 wt.%, more preferably at least 5 wt.% of the amphoteric polymer. Typically, the detergent composition contains not more than 20 wt.% of the amphoteric polymer.
- the aforementioned polymer-containing particles typically have a diameter in the range of 0.1 to 1000 ⁇ .
- the polymer-containing particles have a diameter in the range of 10 to 800 ⁇ , most preferably of 20 to 500 ⁇ .
- the amphoteric polymer is contained in polymer-containing particles that comprise one or more core particles and a coating that contains the amphoteric polymer.
- the one or more core particles are preferably made of silicate mineral. Examples of suitable silicate materials include feldspar, montmorillonite, bentonite, zeolite and combinations thereof.
- amphoteric polymer is contained in polymer- containing particles containing at least 30 wt.% of water-soluble carrier material. More preferably, the polymer-containing particles contain at least 30 wt.% of water-soluble carrier polymer. Examples of suitable water-soluble carrier polymer include
- the solid laundry detergent composition of the present invention preferably contains 0.2 to 10 wt.%, more preferably 0.3 to 8 wt.% and most preferably 0.4 to 3 wt.% of the amphoteric polymer.
- the amphoteric polymer employed in the present detergent composition preferably has a molecular weight of at least 8,000 Da, more preferably of 12,000 to 100,000 Da and most preferably of 15,000 to 50,000 Da.
- the monomeric units represented by above mentioned formula (I) preferably represent at least 50%, more preferably at least 70%, even more preferably at least 90% and most preferably at least 95% of the monomeric units of the amphoteric polymer.
- R 1 in formula (I) preferably represents Ci to C3 alkyl, more preferably it represents methyl or ethyl, and most preferably it represents methyl group.
- R 2 and R 3 in formula (I) independently of each other represent Ci to C3 alkyl, more preferably methyl or ethyl. Most preferably, R 2 and R 3 each represents methyl group.
- the integer n in formula (I) preferably is 1 to 3. Most preferably n is 2.
- the integer p in formula (I) preferably is 2 to 4. Most preferably p is 3.
- X in formula (I) represents COO " .
- Carboxybetaine methacrylate is an example of betaine monomer in which X represents COO " .
- composition may additionally comprise the amphoteric polymer where X in formula (I) represents SO3 "2 .
- Sulfobetaine methacrylate is an example of betaine monomer in which X represents SO3 "2 .
- the amphoteric polymer employed in accordance with the present invention is not a copolymer comprising methacryloylalklyl dimethylammonium-methylcarboxybetaine- butyl methacrylate.
- the amphoteric polymer of the present invention is a homopolymer, i.e. a polymer in which all monomeric units are betaine units according to formula (I).
- the amphoteric polymer is a copolymer, it is preferred that at least 20% of the monomeric units of the copolymer are diallyldialkylammonium units, preferably diallyldimethylammonium units.
- the laundry detergent composition of the present invention typically comprises 0.01 to 10 wt.%, more preferably 0.02 to 5 wt.% and most preferably 0.025 to 1 wt.% of surfactants selected from anionic surfactants, zwitterionic surfactants and nonionic surfactants.
- the detergent composition contains at least 0.01 wt.%, more preferably at least 0.02 wt.% and most preferably at least 0.025 wt.% of nonionic surfactant.
- the detergent composition contains at least 0.01 wt.%, more preferably at least 0.02 wt.%, most preferably at least 0.025 wt.% poly(ethylene glycol) alkyl ether represented by the following formula :
- r is an integer in the range of 7 to 17;
- s is an integer in the range of 1 to 25.
- the detergent composition contains 30 to 95 wt.% of builder, more preferably 40 to90 wt.% of builder and most preferably 50 to 75 wt.% of builder.
- Inorganic builders that may be used include sodium carbonate; aluminosilicates, such as zeolites; and layered silicates; and inorganic phosphate builders such as sodium orthophosphate, pyrophosphate and tripolyphosphate.
- Organic builders that may be used include polycarboxylate polymers such as polyacrylates, acrylic/maleic copolymers, and acrylic phosphinates; monomeric polycarboxylates such as citrates, gluconates, oxydisuccinates, glycerol mono-, di and trisuccinates, carboxymethyloxy succinates, carboxymethyloxymalonates, dipicolinates, hydroxyethyliminodiacetates, alkyl- and alkenylmalonates and succinates; and sulfonated fatty acid salts.
- polycarboxylate polymers such as polyacrylates, acrylic/maleic copolymers, and acrylic phosphinates
- monomeric polycarboxylates such as citrates, gluconates, oxydisuccinates, glycerol mono-, di and trisuccinates, carboxymethyloxy succinates, carboxymethyloxymalonates, dipicolinates, hydroxyethyliminodiacetates, alky
- Another aspect of the present invention relates to the use of an amphoteric polymer as defined herein before for removing greasy stains from a fabric or for improving the oil repellency of a fabric, said use comprising contacting the fabric with an aqueous liquid containing 0.01 to2 wt.% of the amphoteric polymer.
- the aqueous liquid further contains 0.01 to 2 wt.% of nonionic surfactant, more preferably 0.02 to 1 wt.% of an nonionic surfactant represented by aforementioned formula.
- the invention is further illustrated by the following non-limiting examples. EXAMPLES Example 1
- CBMA 2-Carboxy-N,N-dimethyl-N-(2'-(methacryloyloxy)ethyl)ethylimminium inner salt
- Free radical polymerization of the CBMA monomer was carried out in an aqueous medium using the method described by Lee et al. (Synthesis and solubility of the poly(sulfobetaine)s and the corresponding cationic polymers: Synthesis and characterization of sulphobetaines and the corresponding cationic monomers by nuclear magnetic resonance spectra, Polymer (1994), vol. 35, no. 10, 2210 - 2217). Potassium persulfate was used as an initiator and polymerization was carried out in an inert atmosphere under stirring at 60 to 70 °C for 8 hours. Molecular weight of the CBMA hompolymer was in the range of 10,000 to 100,000 Da.
- a copolymer of the CBMA monomer and N,N-diallyl-N,N-dimethyl ammonium chloride (DADMAC) was prepared following a free radical polymerization technique described by Thomas et al. (Synthesis, Characterization, and Aqueous Solution Behavior of Electrolyte- and pH-Responsive Carboxybetaine-Containing Cyclocopolymers, Macromolecules (2003), 36(26), 9710-9715). Potassium persulphate was used as the initiator and the polymerization was carried out for 8 hours at 70 °C under nitrogen blanket. Molecular weight of the CMBA DADMAC copolymer was in the range of 10,000 to 100,000 Da.
- the ratio of the two monomers used was 65 mol% CBMA and 35 wt% DADMAC.
- Free radical polymerization of SBMA (sulphobetaine methacrylate; Sigma Aldrich) monomer was carried out in an aqueous medium using the method described by Lee et al. (Synthesis and solubility of the poly(sulfobetaine)s and the corresponding cationic polymers: Synthesis and characterization of sulphobetaines and the corresponding cationic monomers by nuclear magnetic resonance spectra, Polymer (1994), vol. 35, no. 10, 2210 - 2217). Potassium persulfate was used as an initiator and the
- Polyester swatches were treated with polymer solutions containing different
- the SRI (Stain Removal Index) of the dried washed fabric samples was determined.
- the SRI-values were determined by measuring reflectance of the fabric swatches measured at R460 (values at 460 nanometer, UV excluded and included) using a MICROTEK® Artix Scanner F1 with Software: Silverfast Ai Studio, Lasersoft Imaging.
- Example 1 was repeated except that this time polyester and cotton swatches were first stained with a model sebum, followed by ageing for 24 hours. These stained fabric samples were washed in a Tergotometer at 1 10 rpm at ambient temperature in water (24 °fH) in the presence of 1 .5 g/l of Surf Excel®, which is a commercial detergent composition of Unilever.
- Example 1 was repeated, except that this time the aged stained fabric samples were washed in a Tergotometer Tergotometer at 1 10 rpm at ambient temperature in water (24 °fH). The results are tabulated in Table 3. Table 3
- Polyester swatches were treated with polymer solutions of the copolymer polyCBMA- co-DADMAC of Example 1.
- the solutions contained different concentrations of the copolymer or did not contain any copolymer (control, refer Table 4).
- the treated swatches were allowed to dry, followed by staining (0.2 mL) with artificial sebum and ageing for 24 hours.
- the fabric was then washed in a Tergotometer at 1 10 rpm at ambient temperature in water (24 °fH, no additives/surfactants were used), followed by drying.
- Polyester swatches were treated with polymer solutions of the homopolymer polySBMA of Example 1 .
- the solutions contained different concentrations of the homopolymer or did not containin any homopolymer (control, refer Table 5).
- the swatches were allowed to dry, followed by staining (0.2 mL) with artificial sebum and ageing for 24 hours.
- the fabric was then washed in a Tergotometer in water (no additives/surfactants were used), followed by drying.
- the SRI of the dried washed fabric samples was determined in the same way as in Example 1. The results of these measurements are shown in Table 5.
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- Engineering & Computer Science (AREA)
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Abstract
L'invention concerne une composition de détergent à lessive solide contenant un polymère amphotère, ledit polymère amphotère étant caractérisé en ce qu'au moins 30 % de ses motifs monomères sont des motifs bétaïne représentés par la formule (I) suivante : H2C=C(R1)-C(O)O-(CH2)n-N+(R2)(R3)-(CH2)p-X (I) dans laquelle : • R1 représente un atome d'hydrogène ou un groupe alkyle en C1 à C6 linéaire ou ramifié ; • R2 et R3, indépendamment l'un de l'autre, représentent un groupe alkyle, hydroxyalkyle ou aminoalkyle dans lequel le groupe alkyle est un alkyle en C1 à C6 linéaire ou ramifié ; • n est un nombre entier dans la plage de 1 à 4 ; • p est un nombre entier dans la plage de 2 à 8 ; • X représente COO". Les inventeurs ont découvert que des compositions de détergent à lessive contenant le polymère amphotère mentionné ci-dessus sont aptes à augmenter le caractère oléofuge de tissus.
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
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EP17767808.3A EP3519545B1 (fr) | 2016-10-03 | 2017-09-12 | Composition de détergent pour lessive contenant un polymère amphotère |
CN201780061396.2A CN109790494A (zh) | 2016-10-03 | 2017-09-12 | 包含两性聚合物的洗衣洗涤剂组合物 |
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EP16192012 | 2016-10-03 | ||
EP16192012.9 | 2016-10-03 |
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WO2018065177A1 true WO2018065177A1 (fr) | 2018-04-12 |
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PCT/EP2017/072863 WO2018065177A1 (fr) | 2016-10-03 | 2017-09-12 | Composition de détergent à lessive contenant un polymère amphotère |
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EP (1) | EP3519545B1 (fr) |
CN (1) | CN109790494A (fr) |
WO (1) | WO2018065177A1 (fr) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN108998271A (zh) * | 2018-06-21 | 2018-12-14 | 纳爱斯浙江科技有限公司 | 一种基于无规共聚物的抗沉积剂及含有该抗沉积剂的织物洗涤剂 |
Families Citing this family (1)
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WO2020251767A1 (fr) * | 2019-06-14 | 2020-12-17 | Dow Global Technologies Llc | Renforçateur de nettoyage polymère |
Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5512644A (en) * | 1993-09-08 | 1996-04-30 | Toyo Boseki Kabushiki Kaisha | Ampholytic polymer capable of absorbing aqueous electrolyte solution |
JPH10195498A (ja) | 1996-12-27 | 1998-07-28 | Lion Corp | 液体洗浄剤組成物 |
JPH11335239A (ja) | 1998-05-25 | 1999-12-07 | Lion Corp | ステインリムーバー組成物 |
WO2001005923A1 (fr) * | 1999-07-16 | 2001-01-25 | The Procter & Gamble Company | Compositions de detergent a lessive contenant des polyamines zwitterioniques et des tensioactifs ramifies en milieu de chaine |
US20010014658A1 (en) | 1998-10-07 | 2001-08-16 | Ecolab Inc. | Laundry pre-treatment or pre-spotting compositions used to improve aqueous laundry processing |
US20060217286A1 (en) | 2003-02-20 | 2006-09-28 | Geoffroy Cedric | Composition for cleaning or rinsing hard surfaces |
US20150267147A1 (en) | 2012-12-05 | 2015-09-24 | Henkel Ag & Co. Kgaa | Removal of greasy stains |
WO2016087258A1 (fr) * | 2014-12-05 | 2016-06-09 | Henkel Ag & Co. Kgaa | Détergents et produits de nettoyage à principe actif polymère |
-
2017
- 2017-09-12 EP EP17767808.3A patent/EP3519545B1/fr active Active
- 2017-09-12 WO PCT/EP2017/072863 patent/WO2018065177A1/fr active Application Filing
- 2017-09-12 CN CN201780061396.2A patent/CN109790494A/zh active Pending
Patent Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5512644A (en) * | 1993-09-08 | 1996-04-30 | Toyo Boseki Kabushiki Kaisha | Ampholytic polymer capable of absorbing aqueous electrolyte solution |
JPH10195498A (ja) | 1996-12-27 | 1998-07-28 | Lion Corp | 液体洗浄剤組成物 |
JPH11335239A (ja) | 1998-05-25 | 1999-12-07 | Lion Corp | ステインリムーバー組成物 |
US20010014658A1 (en) | 1998-10-07 | 2001-08-16 | Ecolab Inc. | Laundry pre-treatment or pre-spotting compositions used to improve aqueous laundry processing |
WO2001005923A1 (fr) * | 1999-07-16 | 2001-01-25 | The Procter & Gamble Company | Compositions de detergent a lessive contenant des polyamines zwitterioniques et des tensioactifs ramifies en milieu de chaine |
US20060217286A1 (en) | 2003-02-20 | 2006-09-28 | Geoffroy Cedric | Composition for cleaning or rinsing hard surfaces |
US20150267147A1 (en) | 2012-12-05 | 2015-09-24 | Henkel Ag & Co. Kgaa | Removal of greasy stains |
WO2016087258A1 (fr) * | 2014-12-05 | 2016-06-09 | Henkel Ag & Co. Kgaa | Détergents et produits de nettoyage à principe actif polymère |
Non-Patent Citations (3)
Title |
---|
LEE ET AL.: "Synthesis and solubility of the poly(sulfobetaine)s and the corresponding cationic polymers: Synthesis and characterization of sulphobetaines and the corresponding cationic monomers by nuclear magnetic resonance spectra", POLYMER, vol. 35, no. 10, 1994, pages 2210 - 2217 |
THOMAS ET AL.: "Synthesis, Characterization, and Aqueous Solution Behavior of Electrolyte- and pH-Responsive Carboxybetaine-Containing Cyclocopolymers", MACROMOLECULES, vol. 36, no. 26, 2003, pages 9710 - 9715, XP007910905, DOI: doi:10.1021/ma0345807 |
ZHANG ET AL.: "Superlow Fouling Sulfobetaine and Carboxybetaine Polymers on Glass Slides", LANGMUIR, vol. 22, no. 24, 2006, pages 10073, XP055001604, DOI: doi:10.1021/la062175d |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN108998271A (zh) * | 2018-06-21 | 2018-12-14 | 纳爱斯浙江科技有限公司 | 一种基于无规共聚物的抗沉积剂及含有该抗沉积剂的织物洗涤剂 |
Also Published As
Publication number | Publication date |
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EP3519545B1 (fr) | 2019-11-13 |
EP3519545A1 (fr) | 2019-08-07 |
CN109790494A (zh) | 2019-05-21 |
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