TWI637053B - 聚合物、製備其聚合物溶液之方法及從溶液中鉗合金屬離子之方法 - Google Patents
聚合物、製備其聚合物溶液之方法及從溶液中鉗合金屬離子之方法 Download PDFInfo
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- TWI637053B TWI637053B TW104108103A TW104108103A TWI637053B TW I637053 B TWI637053 B TW I637053B TW 104108103 A TW104108103 A TW 104108103A TW 104108103 A TW104108103 A TW 104108103A TW I637053 B TWI637053 B TW I637053B
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- Prior art keywords
- acid
- polymer
- monomer
- solution
- sodium
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- 229920000642 polymer Polymers 0.000 title claims abstract description 211
- 238000000034 method Methods 0.000 title claims description 72
- 229910021645 metal ion Inorganic materials 0.000 title claims description 9
- 238000004519 manufacturing process Methods 0.000 title description 8
- 230000008569 process Effects 0.000 title description 4
- -1 tri-substituted vinyl Chemical group 0.000 claims abstract description 142
- 239000000178 monomer Substances 0.000 claims abstract description 124
- 239000002253 acid Substances 0.000 claims abstract description 105
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 17
- 239000000203 mixture Substances 0.000 claims description 196
- 238000006116 polymerization reaction Methods 0.000 claims description 45
- 150000003839 salts Chemical class 0.000 claims description 45
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 claims description 44
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 claims description 40
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 31
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 28
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 28
- 230000003472 neutralizing effect Effects 0.000 claims description 21
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 19
- 150000002148 esters Chemical class 0.000 claims description 17
- LCPVQAHEFVXVKT-UHFFFAOYSA-N 2-(2,4-difluorophenoxy)pyridin-3-amine Chemical compound NC1=CC=CN=C1OC1=CC=C(F)C=C1F LCPVQAHEFVXVKT-UHFFFAOYSA-N 0.000 claims description 14
- CHQMHPLRPQMAMX-UHFFFAOYSA-L sodium persulfate Substances [Na+].[Na+].[O-]S(=O)(=O)OOS([O-])(=O)=O CHQMHPLRPQMAMX-UHFFFAOYSA-L 0.000 claims description 14
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 13
- 239000000654 additive Substances 0.000 claims description 13
- MNCGMVDMOKPCSQ-UHFFFAOYSA-M sodium;2-phenylethenesulfonate Chemical compound [Na+].[O-]S(=O)(=O)C=CC1=CC=CC=C1 MNCGMVDMOKPCSQ-UHFFFAOYSA-M 0.000 claims description 13
- 239000012736 aqueous medium Substances 0.000 claims description 10
- 239000003638 chemical reducing agent Substances 0.000 claims description 10
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 claims description 10
- 150000005846 sugar alcohols Polymers 0.000 claims description 10
- ATVJXMYDOSMEPO-UHFFFAOYSA-N 3-prop-2-enoxyprop-1-ene Chemical compound C=CCOCC=C ATVJXMYDOSMEPO-UHFFFAOYSA-N 0.000 claims description 8
- 239000003505 polymerization initiator Substances 0.000 claims description 8
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 claims description 6
- 229920002472 Starch Polymers 0.000 claims description 6
- 239000007800 oxidant agent Substances 0.000 claims description 6
- 235000019698 starch Nutrition 0.000 claims description 6
- 230000000996 additive effect Effects 0.000 claims description 5
- 239000012535 impurity Substances 0.000 claims description 5
- 230000001590 oxidative effect Effects 0.000 claims description 5
- 229920002451 polyvinyl alcohol Polymers 0.000 claims description 5
- 235000010265 sodium sulphite Nutrition 0.000 claims description 5
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 3
- 239000004372 Polyvinyl alcohol Substances 0.000 claims description 3
- 229910052698 phosphorus Inorganic materials 0.000 claims description 3
- 239000011574 phosphorus Substances 0.000 claims description 3
- 239000008107 starch Substances 0.000 claims description 3
- IRLPACMLTUPBCL-KQYNXXCUSA-N 5'-adenylyl sulfate Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](COP(O)(=O)OS(O)(=O)=O)[C@@H](O)[C@H]1O IRLPACMLTUPBCL-KQYNXXCUSA-N 0.000 claims 3
- 239000003599 detergent Substances 0.000 abstract description 119
- 238000005516 engineering process Methods 0.000 abstract description 12
- HNEGQIOMVPPMNR-IHWYPQMZSA-N citraconic acid Chemical compound OC(=O)C(/C)=C\C(O)=O HNEGQIOMVPPMNR-IHWYPQMZSA-N 0.000 abstract description 6
- 229940018557 citraconic acid Drugs 0.000 abstract description 6
- HNEGQIOMVPPMNR-NSCUHMNNSA-N mesaconic acid Chemical compound OC(=O)C(/C)=C/C(O)=O HNEGQIOMVPPMNR-NSCUHMNNSA-N 0.000 abstract description 6
- HNEGQIOMVPPMNR-UHFFFAOYSA-N methylfumaric acid Natural products OC(=O)C(C)=CC(O)=O HNEGQIOMVPPMNR-UHFFFAOYSA-N 0.000 abstract description 5
- 230000032050 esterification Effects 0.000 abstract 1
- 238000005886 esterification reaction Methods 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 103
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 75
- 229920001577 copolymer Polymers 0.000 description 58
- 239000000047 product Substances 0.000 description 50
- 239000002002 slurry Substances 0.000 description 50
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- 102000004190 Enzymes Human genes 0.000 description 41
- 108090000790 Enzymes Proteins 0.000 description 41
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 41
- 229940088598 enzyme Drugs 0.000 description 41
- 125000004432 carbon atom Chemical group C* 0.000 description 40
- 239000004615 ingredient Substances 0.000 description 38
- 239000002904 solvent Substances 0.000 description 36
- 239000002736 nonionic surfactant Substances 0.000 description 35
- 239000007844 bleaching agent Substances 0.000 description 32
- 239000000843 powder Substances 0.000 description 32
- 239000000523 sample Substances 0.000 description 31
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 29
- 239000000463 material Substances 0.000 description 29
- 238000009472 formulation Methods 0.000 description 28
- 239000003999 initiator Substances 0.000 description 28
- 239000007788 liquid Substances 0.000 description 27
- 150000001875 compounds Chemical class 0.000 description 25
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 24
- 125000000217 alkyl group Chemical group 0.000 description 23
- 229910052799 carbon Inorganic materials 0.000 description 23
- 238000012360 testing method Methods 0.000 description 23
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 22
- 238000004140 cleaning Methods 0.000 description 22
- 229920001296 polysiloxane Polymers 0.000 description 22
- 239000011734 sodium Substances 0.000 description 22
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 21
- 229910052783 alkali metal Inorganic materials 0.000 description 21
- 239000007864 aqueous solution Substances 0.000 description 21
- 239000004744 fabric Substances 0.000 description 21
- 102000035195 Peptidases Human genes 0.000 description 20
- 108091005804 Peptidases Proteins 0.000 description 20
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 20
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 19
- 239000000126 substance Substances 0.000 description 18
- 238000000746 purification Methods 0.000 description 17
- 239000002453 shampoo Substances 0.000 description 17
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 16
- 239000002245 particle Substances 0.000 description 16
- 229910052708 sodium Inorganic materials 0.000 description 16
- 235000019832 sodium triphosphate Nutrition 0.000 description 16
- 150000001298 alcohols Chemical class 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 15
- 238000006386 neutralization reaction Methods 0.000 description 15
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 14
- 239000000460 chlorine Substances 0.000 description 14
- 229910052801 chlorine Inorganic materials 0.000 description 14
- 229910052751 metal Inorganic materials 0.000 description 14
- 239000002184 metal Substances 0.000 description 14
- 235000011121 sodium hydroxide Nutrition 0.000 description 14
- 229920001897 terpolymer Polymers 0.000 description 14
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 13
- 230000000694 effects Effects 0.000 description 13
- PEDCQBHIVMGVHV-UHFFFAOYSA-N glycerol Substances OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 13
- 239000011572 manganese Substances 0.000 description 13
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 13
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 239000004115 Sodium Silicate Substances 0.000 description 12
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- 125000001931 aliphatic group Chemical group 0.000 description 11
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- 229910052760 oxygen Inorganic materials 0.000 description 11
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- 238000005481 NMR spectroscopy Methods 0.000 description 10
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- UFZOPKFMKMAWLU-UHFFFAOYSA-N ethoxy(methyl)phosphinic acid Chemical compound CCOP(C)(O)=O UFZOPKFMKMAWLU-UHFFFAOYSA-N 0.000 description 10
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- 125000005270 trialkylamine group Chemical group 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-O triethanolammonium Chemical compound OCC[NH+](CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-O 0.000 description 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical compound CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 0.000 description 1
- 150000001461 trihydroxyphenols Chemical class 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- BSVBQGMMJUBVOD-UHFFFAOYSA-N trisodium borate Chemical compound [Na+].[Na+].[Na+].[O-]B([O-])[O-] BSVBQGMMJUBVOD-UHFFFAOYSA-N 0.000 description 1
- HRXKRNGNAMMEHJ-UHFFFAOYSA-K trisodium citrate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O HRXKRNGNAMMEHJ-UHFFFAOYSA-K 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical class [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 229960000281 trometamol Drugs 0.000 description 1
- 239000012588 trypsin Substances 0.000 description 1
- 230000001810 trypsinlike Effects 0.000 description 1
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
- 229940124543 ultraviolet light absorber Drugs 0.000 description 1
- KJIOQYGWTQBHNH-UHFFFAOYSA-N undecanol Chemical compound CCCCCCCCCCCO KJIOQYGWTQBHNH-UHFFFAOYSA-N 0.000 description 1
- 239000004474 valine Substances 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
- 238000009463 water soluble packaging Methods 0.000 description 1
- 239000000811 xylitol Substances 0.000 description 1
- HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 description 1
- 235000010447 xylitol Nutrition 0.000 description 1
- 229960002675 xylitol Drugs 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 239000004246 zinc acetate Substances 0.000 description 1
- 150000003752 zinc compounds Chemical class 0.000 description 1
- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 description 1
- 229910000368 zinc sulfate Inorganic materials 0.000 description 1
- 229960001763 zinc sulfate Drugs 0.000 description 1
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
- C11D3/3746—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- C11D3/3757—(Co)polymerised carboxylic acids, -anhydrides, -esters in solid and liquid compositions
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/12—Polymerisation in non-solvents
- C08F2/16—Aqueous medium
- C08F2/22—Emulsion polymerisation
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/04—Acids; Metal salts or ammonium salts thereof
- C08F220/06—Acrylic acid; Methacrylic acid; Metal salts or ammonium salts thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
- C08F222/02—Acids; Metal salts or ammonium salts thereof, e.g. maleic acid or itaconic acid
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/14—Peroxides
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F212/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring
- C08F212/02—Monomers containing only one unsaturated aliphatic radical
- C08F212/04—Monomers containing only one unsaturated aliphatic radical containing one ring
- C08F212/14—Monomers containing only one unsaturated aliphatic radical containing one ring substituted by heteroatoms or groups containing heteroatoms
- C08F212/30—Sulfur
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Detergent Compositions (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201461953239P | 2014-03-14 | 2014-03-14 | |
| US61/953,239 | 2014-03-14 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| TW201538717A TW201538717A (zh) | 2015-10-16 |
| TWI637053B true TWI637053B (zh) | 2018-10-01 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW104108103A TWI637053B (zh) | 2014-03-14 | 2015-03-13 | 聚合物、製備其聚合物溶液之方法及從溶液中鉗合金屬離子之方法 |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US11214758B2 (https=) |
| EP (1) | EP3116924B1 (https=) |
| JP (2) | JP7071039B2 (https=) |
| KR (1) | KR102350475B1 (https=) |
| CN (1) | CN106574018A (https=) |
| BR (1) | BR112016021154A2 (https=) |
| ES (1) | ES2823562T3 (https=) |
| TW (1) | TWI637053B (https=) |
| WO (1) | WO2015138872A1 (https=) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US11879111B2 (en) | 2020-03-27 | 2024-01-23 | Ecolab Usa Inc. | Detergent compositions, cleaning systems and methods of cleaning cosmetic and other soils |
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| BR112019011780B1 (pt) | 2016-12-12 | 2023-03-07 | Clariant International Ltd | Polímero compreendendo carbono de material biológico, seu processo de obtenção e seu uso |
| WO2018108611A1 (en) | 2016-12-12 | 2018-06-21 | Clariant International Ltd | Use of bio-based polymer in a cosmetic, dermatological or pharmaceutical composition |
| EP3554644B1 (en) | 2016-12-15 | 2025-03-19 | Clariant International Ltd | Water-soluble and/or water-swellable hybrid polymer |
| EP3554646B1 (en) | 2016-12-15 | 2025-03-19 | Clariant International Ltd | Water-soluble and/or water-swellable hybrid polymer |
| ES3017507T3 (en) | 2016-12-15 | 2025-05-13 | Clariant Int Ltd | Water-soluble and/or water-swellable hybrid polymer |
| EP3554643B1 (en) | 2016-12-15 | 2025-03-19 | Clariant International Ltd | Water-soluble and/or water-swellable hybrid polymer |
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| EP3418366A1 (en) | 2017-06-19 | 2018-12-26 | The Procter & Gamble Company | Automatic dishwashing cleaning composition |
| EP3441450A1 (en) * | 2017-08-11 | 2019-02-13 | The Procter & Gamble Company | Automatic dishwashing composition |
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| WO2019099145A1 (en) * | 2017-11-15 | 2019-05-23 | Dow Global Technologies Llc | Dispersant polymer for autodish formulations |
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- 2015-03-13 WO PCT/US2015/020408 patent/WO2015138872A1/en not_active Ceased
- 2015-03-13 KR KR1020167028558A patent/KR102350475B1/ko active Active
- 2015-03-13 TW TW104108103A patent/TWI637053B/zh active
- 2015-03-13 EP EP15712768.9A patent/EP3116924B1/en not_active Revoked
- 2015-03-13 CN CN201580024475.7A patent/CN106574018A/zh active Pending
- 2015-03-13 ES ES15712768T patent/ES2823562T3/es active Active
- 2015-03-13 US US15/125,820 patent/US11214758B2/en active Active
- 2015-03-13 JP JP2016575634A patent/JP7071039B2/ja active Active
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2020
- 2020-01-17 JP JP2020005968A patent/JP2020063458A/ja active Pending
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US11879111B2 (en) | 2020-03-27 | 2024-01-23 | Ecolab Usa Inc. | Detergent compositions, cleaning systems and methods of cleaning cosmetic and other soils |
| US12203050B2 (en) | 2020-03-27 | 2025-01-21 | Ecolab Usa Inc. | Detergent compositions, cleaning systems and methods of cleaning cosmetic and other soils |
Also Published As
| Publication number | Publication date |
|---|---|
| EP3116924A1 (en) | 2017-01-18 |
| ES2823562T3 (es) | 2021-05-07 |
| BR112016021154A2 (pt) | 2021-08-24 |
| US20170022451A1 (en) | 2017-01-26 |
| EP3116924B1 (en) | 2020-08-19 |
| KR20160135272A (ko) | 2016-11-25 |
| CN106574018A (zh) | 2017-04-19 |
| JP2020063458A (ja) | 2020-04-23 |
| US11214758B2 (en) | 2022-01-04 |
| JP7071039B2 (ja) | 2022-05-18 |
| TW201538717A (zh) | 2015-10-16 |
| WO2015138872A1 (en) | 2015-09-17 |
| JP2017510693A (ja) | 2017-04-13 |
| KR102350475B1 (ko) | 2022-01-11 |
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