CN111868221A - 用于洗衣清洁剂的抗再沉积添加剂 - Google Patents
用于洗衣清洁剂的抗再沉积添加剂 Download PDFInfo
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- CN111868221A CN111868221A CN201980019456.3A CN201980019456A CN111868221A CN 111868221 A CN111868221 A CN 111868221A CN 201980019456 A CN201980019456 A CN 201980019456A CN 111868221 A CN111868221 A CN 111868221A
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- meth
- composition
- polymer
- ethylenically unsaturated
- alkyl
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- 239000003599 detergent Substances 0.000 title claims abstract description 17
- 239000000654 additive Substances 0.000 title description 10
- 229920000642 polymer Polymers 0.000 claims abstract description 41
- 239000000178 monomer Substances 0.000 claims abstract description 35
- 239000000203 mixture Substances 0.000 claims abstract description 24
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims abstract description 11
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000004094 surface-active agent Substances 0.000 claims abstract description 8
- 239000003795 chemical substances by application Substances 0.000 claims abstract 4
- -1 aminopropyl Chemical group 0.000 claims description 11
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 7
- WIYVVIUBKNTNKG-UHFFFAOYSA-N 6,7-dimethoxy-3,4-dihydronaphthalene-2-carboxylic acid Chemical compound C1CC(C(O)=O)=CC2=C1C=C(OC)C(OC)=C2 WIYVVIUBKNTNKG-UHFFFAOYSA-N 0.000 claims description 6
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims description 5
- 239000003945 anionic surfactant Substances 0.000 claims description 5
- 150000003926 acrylamides Chemical class 0.000 claims description 3
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 claims description 3
- QAOWNCQODCNURD-UHFFFAOYSA-L sulfate group Chemical group S(=O)(=O)([O-])[O-] QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 3
- 150000001252 acrylic acid derivatives Chemical class 0.000 claims description 2
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims description 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims 1
- 125000001302 tertiary amino group Chemical group 0.000 claims 1
- 239000000243 solution Substances 0.000 description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 15
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 13
- 239000008367 deionised water Substances 0.000 description 12
- 229910021641 deionized water Inorganic materials 0.000 description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 239000003999 initiator Substances 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 239000002689 soil Substances 0.000 description 7
- 230000000996 additive effect Effects 0.000 description 6
- 239000004744 fabric Substances 0.000 description 6
- 238000005227 gel permeation chromatography Methods 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 6
- 229940001584 sodium metabisulfite Drugs 0.000 description 6
- 235000010262 sodium metabisulphite Nutrition 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- GDFCSMCGLZFNFY-UHFFFAOYSA-N Dimethylaminopropyl Methacrylamide Chemical compound CN(C)CCCNC(=O)C(C)=C GDFCSMCGLZFNFY-UHFFFAOYSA-N 0.000 description 5
- 229920002125 Sokalan® Polymers 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 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 description 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- 125000004103 aminoalkyl group Chemical group 0.000 description 4
- 229920001577 copolymer Polymers 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- CHQMHPLRPQMAMX-UHFFFAOYSA-L sodium persulfate Substances [Na+].[Na+].[O-]S(=O)(=O)OOS([O-])(=O)=O CHQMHPLRPQMAMX-UHFFFAOYSA-L 0.000 description 4
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 229910019142 PO4 Inorganic materials 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 239000002270 dispersing agent Substances 0.000 description 3
- 150000002148 esters Chemical group 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 239000004584 polyacrylic acid Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- JKNCOURZONDCGV-UHFFFAOYSA-N 2-(dimethylamino)ethyl 2-methylprop-2-enoate Chemical compound CN(C)CCOC(=O)C(C)=C JKNCOURZONDCGV-UHFFFAOYSA-N 0.000 description 2
- IRLPACMLTUPBCL-KQYNXXCUSA-N 5'-adenylyl sulfate Chemical group 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 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- 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 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 238000012512 characterization method Methods 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 239000012459 cleaning agent Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- 150000002191 fatty alcohols Chemical class 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- SURQXAFEQWPFPV-UHFFFAOYSA-L iron(2+) sulfate heptahydrate Chemical compound O.O.O.O.O.O.O.[Fe+2].[O-]S([O-])(=O)=O SURQXAFEQWPFPV-UHFFFAOYSA-L 0.000 description 2
- 239000003550 marker Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000002516 radical scavenger Substances 0.000 description 2
- 238000001542 size-exclusion chromatography Methods 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 2
- 150000008054 sulfonate salts Chemical class 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
- 229910021536 Zeolite Inorganic materials 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229940077388 benzenesulfonate Drugs 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
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- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
- 238000004851 dishwashing Methods 0.000 description 1
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 125000005395 methacrylic acid group Chemical group 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 1
- 229910000403 monosodium phosphate Inorganic materials 0.000 description 1
- 235000019799 monosodium phosphate Nutrition 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- JRKICGRDRMAZLK-UHFFFAOYSA-L persulfate group Chemical class S(=O)(=O)([O-])OOS(=O)(=O)[O-] JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 229960004063 propylene glycol Drugs 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 229920005604 random copolymer Polymers 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229940071207 sesquicarbonate Drugs 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 235000019832 sodium triphosphate Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 239000010457 zeolite Substances 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
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/02—Anionic compounds
- C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
- C11D1/14—Sulfonic acids or sulfuric acid esters; Salts thereof derived from aliphatic hydrocarbons or mono-alcohols
- C11D1/143—Sulfonic acid esters
-
- 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
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/02—Anionic compounds
- C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
- C11D1/14—Sulfonic acids or sulfuric acid esters; Salts thereof derived from aliphatic hydrocarbons or mono-alcohols
- C11D1/146—Sulfuric acid esters
-
- 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
-
- 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
- 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
- C11D3/3769—(Co)polymerised monomers containing nitrogen, e.g. carbonamides, nitriles or amines
-
- 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
- C11D3/3769—(Co)polymerised monomers containing nitrogen, e.g. carbonamides, nitriles or amines
- C11D3/3773—(Co)polymerised monomers containing nitrogen, e.g. carbonamides, nitriles or amines in liquid compositions
-
- C11D2111/12—
Abstract
一种洗衣清洁剂组合物,其包含抗再沉积剂、表面活性剂,和任选地助洗剂,其中所述抗再沉积剂是包含以下聚合单元的聚合物:(a)5wt%到40wt%的具有至少一个6到11.5的pKa值的至少一种含氮烯系不饱和单体,和(b)60wt%到95wt%的至少一种烯系不饱和羧酸单体。
Description
背景技术
本发明大体上涉及在洗衣清洁剂组合物中可作为抗再沉积添加剂的聚合物。
常规地,已将如聚丙烯酸和羧甲基纤维素的聚合物配制到洗衣清洁剂中,以便防止污垢在洗涤过程期间再沉积到衣物上。然而,这些聚合物中的许多聚合物没有展现出足够的效果,或者其需要相对高的剂量以便满足当今洗衣过程的需求,在此过程中减少用水量的环境趋势已大幅度增加了洗涤槽池中污垢的浓度。例如,GB2104091A公开了出于此目的的两性共聚物。然而,改进的添加剂将是有用的。
发明内容
本发明涉及一种洗衣清洁剂组合物,其包含表面活性剂,任选地助洗剂,以及聚合物,所述聚合物包含以下聚合单元:(a)5wt%到40wt%的具有至少一个6到11.5的pKa值的至少一种含氮烯系不饱和单体,和(b)60wt%到95wt%的至少一种烯系不饱和羧酸单体。
具体实施方式
除非另外指示,否则所有百分比均是重量百分比(wt%),并且所有温度均以℃为单位。如本领域中已知,通过凝胶渗透色谱法(GPC)使用聚丙烯酸标准品测量重量平均分子量Mw。GPC技术详细地论述于以下:《现代尺寸排阻色谱法(Modern Size ExclusionChromatography)》,W.W.Yau,J.J.Kirkland,D.D.Bly;威利国际科学(Wiley-Interscience),1979和《材料表征和化学分析指南(A Guide to MaterialsCharacterization and Chemical Analysis)》,J.P.Sibilia;VCH,1988,第81-84页。本文所报告的分子量以道尔顿为单位。如本文所用,术语“(甲基)丙烯酸”是指丙烯酸或甲基丙烯酸;术语“碳酸盐”是指碳酸盐、碳酸氢盐或倍半碳酸盐的碱金属或铵盐;术语“和术语“柠檬酸盐”是指碱金属柠檬酸盐。聚合物中单体单元的百分比是固体重量(即,不包括存在于聚合物乳液中的任何水)的百分比。关于聚合物中聚合羧酸单元的所有提及包括所述酸的金属盐,其将以接近或高于羧酸基的pKa的pH值存在。pKa值在25℃下测量。胺的pKa是指质子化胺的pKa。
优选地,烯系不饱和羧酸单体是C3-C8单烯系不饱和羧酸单体,优选地为C3-C4。优选地,羧酸单体具有至少一个附接到碳-碳双键的碳上的羧基。优选地,羧酸单体具有一个或两个羧基,优选地为一个。优选地,单烯系不饱和羧酸单体是(甲基)丙烯酸。
优选地,含氮烯系不饱和单体的至少一个pKa值至少为6.5,优选地至少为7,优选地至少为7.5,优选地至少为8;优选地不大于11,优选地不大于10.5。优选地,含氮烯系不饱和单体是单烯系不饱和的。优选地,含氮烯系不饱和单体包含经取代或未经取代的氨基,优选地叔氨基,优选地叔氨基烷基,优选地二烷氨基烷基,优选地二(C1-C6烷基)氨基烷基,优选地二(C1-C4烷基)氨基烷基,优选地二甲氨基烷基或二乙氨基烷基,优选地二甲氨基烷基。优选地,叔氨基烷基包含3到20个碳原子;优选地至少4个碳原子;优选地不超过15个碳原子,优选地不超过10个,优选地不超过8个。优选地,含氮烯系不饱和单体是(甲基)丙烯酸的经取代氨基烷基酯或酰胺,其优选地为二(C1-C4烷基)氨乙基或二(C1-C4烷基)氨丙基(甲基)丙烯酸酯或(甲基)丙烯酰胺,优选地为二(C1-C2烷基)氨乙基或二(C1-C2烷基)氨丙基酯或酰胺,优选地为甲基丙烯酸2-(二甲氨基)乙酯或N-[3-(二甲氨基)丙基]甲基丙烯酰胺。
优选地,聚合物包含至少7wt%的至少一种含氮烯系不饱和单体的聚合单元,其优选地至少为8wt%;其优选地不超过35wt%,优选地不超过30wt%,优选地不超过25wt%,优选地不超过20wt%,优选地不超过15wt%。优选地,聚合物包含至少65wt%的至少一种烯系不饱和羧酸单体的聚合单元,其优选地至少为70wt%,优选地至少为75wt%,优选地至少为80wt%,优选地至少为85wt%;其优选地不超过93wt%,优选地不超过92wt%。
优选地,聚合物基本上不含包含聚合环氧烷单元(例如环氧乙烷或环氧丙烷)的单体的聚合单元。优选地,聚合物基本上不含除如上文所指示的单体(a)和(b)以外的任何单体的聚合单元。优选地,术语“基本上不含”意指具有不超过5wt%,优选地不超过2wt%,优选地不超过1wt%,优选地不超过0.5wt%,优选地不超过0.1wt%。
优选地,洗衣清洁剂组合物包含0.1wt%到5wt%的聚合物,其优选地至少为0.3wt%,优选地至少为0.5wt%,优选地至少为0.7wt%,优选地至少为0.9wt%;其优选地不超过3wt%,优选地不超过2wt%,优选地不超过1.5wt%。
优选地,洗衣清洁剂组合物包含0wt%到90wt%的水;其优选地不超过70wt%,优选地不超过40wt%,优选地不超过10wt%,优选地不超过5wt%。
优选地,洗衣清洁剂组合物包含至少1.0wt%的至少一种表面活性剂;其优选地至少为2.0wt%,优选地至少为5.0wt%;其优选地不超过70wt%,优选地不超过50wt%,优选地不超过40wt%。
本发明的清洁剂组合物一般由表面活性剂的混合物构成。表面活性剂中的至少一种是阴离子表面活性剂。阴离子表面活性剂优选地为硫酸盐或磺酸盐。一种优选的阴离子表面活性剂是由式Rb-C6H4-SO3M表示的烷基苯磺酸盐,其中Rb表示C6-C18烷基(优选地为直链),C6H4表示苯二基(优选地为1,4-苯二基),并且M表示钠、钾或铵离子。另一优选的阴离子表面活性剂是任选地乙氧基化脂肪醇的半酯盐,式为Ra-O-(AO)nSO3M,其中Ra表示C6-C22直链或支链烷基,AO表示环氧乙烷、环氧丙烷、环氧丁烷或两种或更多种无规或嵌段布置的环氧烷的组合,n为0到10范围的数字且M表示阳离子(优选地为钠、钾或铵离子)。
清洁剂还可含非离子表面活性剂,其优选地为直链醇乙氧基化物,其中醇为具有6-22个碳的直链脂肪醇且表面活性剂含2到20摩尔当量的环氧乙烷。
清洁剂还可含溶剂。当中优选的溶剂是1,2-丙二醇、甘油和乙醇。
清洁剂优选地含助洗剂的混合物。当中优选的助洗剂是三聚磷酸钠、碳酸钠、碳酸氢钠和沸石。清洁剂还可基本上不含磷酸盐(优选地小于1wt%)。
优选地,本发明的聚合物包含不超过0.3wt%的交联单体的聚合单元,其优选地不超过0.1wt%,优选地不超过0.05wt%,优选地不超过0.03wt%,优选地不超过0.01wt%。交联单体是多烯系不饱和单体。
优选地,本发明的聚合物中聚合AMPS单元(包括金属或铵盐)的量不超过10wt%,优选地不超过5wt%,优选地不超过2wt%,优选地不超过1wt%。优选地,本发明的聚合物含不超过8wt%的丙烯酸或甲基丙烯酸的酯的聚合单元,其优选地不超过5wt%,优选地不超过3wt%,优选地不超过1wt%。
优选地,聚合物的Mw至少为5,000,优选地至少为6,000,优选地至少为9,000,优选地至少为10,000,优选地至少为11,000,优选地至少为12,000;其优选地不超过70,000,优选地不超过50,000,优选地不超过30,000,优选地不超过20,000,优选地不超过15,000。
聚合物可与可用于控制自动洗碗机中的不溶性沉积物的其它聚合物组合使用,所述其它聚合物包括例如包含以下组合的聚合物:丙烯酸、甲基丙烯酸、马来酸或其它二酸单体的残基,丙烯酸或甲基丙烯酸的酯(包括聚乙二醇酯),苯乙烯单体、AMPS和其它磺化单体,以及经取代的丙烯酰胺或甲基丙烯酰胺。
优选地,本发明的聚合物通过溶液聚合产生。优选地,聚合物是无规共聚物。优选的溶剂包括2-丙醇、乙醇、水和其混合物。优选地,引发剂不含磷。优选地,聚合物含小于1wt%的磷,其优选地小于0.5wt%,优选地小于0.1wt%,优选地是聚合物不含磷。优选地,用过硫酸盐引发聚合,并且聚合物上的端基为硫酸盐或磺酸盐。聚合物可呈水溶性溶液聚合物、浆料、干粉或颗粒或其它固体形式的形式。
本发明的聚合物潜在地可用作其它清洁和水处理应用的分散剂,包括家用和公共洗涤器中自动洗碗时使用的清洁剂。
实例
材料.在实例中评估以下材料。组成详情提供于表1中。
PAA:丙烯酸的均聚物,ACUSOLTM 445N分散剂聚合物,可购自陶氏化学公司(TheDow Chemical Company)。
实例1-5(本发明):丙烯酸和甲基丙烯酸2-(二甲氨基)乙酯的共聚物。
实例6(比较):丙烯酸和甲基丙烯酸2-(二甲氨基)乙酯的共聚物。
实例7-9(本发明):丙烯酸和N-[3-(二甲氨基)丙基]甲基丙烯酰胺的共聚物。
表1.
AA=丙烯酸,DMAEMA=甲基丙烯酸2-(二甲氨基)乙酯,DMAPMA=N-[3-(二甲氨基)丙基]甲基丙烯酰胺
聚合物合成
实例1
将300g去离子水装入到配备有机械搅拌器、加热套、热电偶、冷凝器、氮气入口和用于添加共进料的入口的两升圆底烧瓶中。制备3.32g的0.15%硫酸铁七水合物的促进剂溶液并将其放置在一旁。制备溶解于10.0g去离子水中的0.63g偏亚硫酸氢钠的釜添加剂(kettle additive)并将其放置在一旁。搅拌釜内含物并使用氮吹扫(nitrogen sweep)将其加热到73±1℃。同时,将380g冰丙烯酸(AA)添加到刻度量筒中以添加到釜中。分别地,将20g的甲基丙烯酸2-(二甲氨基)乙酯(DMAEMA)添加到注射器中以添加到釜中。将溶解于50.0g去离子水中的1.15g过硫酸钠的引发剂溶液添加到注射器中以添加到釜中。将溶解于60.0g去离子水中的13.37g偏亚硫酸氢钠的链调节剂溶液添加到注射器中以添加到釜中。
当釜内含物达到73℃的反应温度时,将促进剂溶液和偏亚硫酸氢钠釜添加剂装料添加到釜中。一旦返回到反应温度,则同步地且分别地开始单体、引发剂和链调节剂共进料。在73±1℃下,经80分钟添加链调节剂溶液,经90分钟添加单体共进料,且经95分钟添加引发剂共进料。制备溶解于10.0g去离子水中的0.53g过硫酸钠的两种追加剂(chaser)溶液并将其添加到分开的注射器中。引发剂共进料完成后10分钟,添加第一追加剂溶液。经10分钟将第一追加剂溶液添加到釜中,接着保持20分钟。在这一保持完成后,经10分钟添加第二追加剂溶液,接着保持另外的20分钟。
在使用空气流冷却反应器的同时,以使反应温度维持在60℃以下的速率经由加料漏斗将175.0g的50%氢氧化钠添加到釜中。将过氧化氢(1.2g的35%溶液)作为清除剂添加到釜中。10分钟后,以使反应温度维持在60℃以下的速率经由加料漏斗将151.3g的50%氢氧化钠添加到釜中。将去离子水(60.0g)作为最终冲洗液添加到漏斗中。接着将内含物冷却并包装。
最终产物的固体含量为42.21%,pH为6.27,粘度为1480cP。残余的AA含量为70ppmw。重量平均分子量和数目平均分子量分别为20783g/mol和5583g/mol。
实例2-6可由本领域技术人员基本上如上文针对实例1所描述的方法制备,其中可对试剂和条件进行适当的修改。
实例7
将300g去离子水和3.32g的0.15%硫酸铁七水合物装入到配备有机械搅拌器、加热套、热电偶、冷凝器、氮气入口和用于添加共进料的入口的两升圆底烧瓶中。制备溶解于7.0g去离子水中的0.4g偏亚硫酸氢钠的釜添加剂并将其放置在一旁。搅拌釜内含物并使用氮吹扫将其加热到73±1℃。同时,将360g冰AA添加到刻度量筒中以添加到釜中。分别地,将40g的N-[3-(二甲氨基)丙基]甲基丙烯酰胺(DMAPMA)添加到注射器中以添加到釜中。将溶解于50.0g去离子水中的1.25g过硫酸钠的引发剂溶液添加到注射器中以添加到釜中。将溶解于70.0g去离子水中的8.6g偏亚硫酸氢钠的链调节剂溶液添加到注射器中以添加到釜中。
当釜内含物达到73℃的反应温度时,将偏亚硫酸氢钠釜添加剂装料添加到釜中。一旦返回到反应温度,则同步地且分别地开始单体、引发剂和链调节剂共进料。在73±1℃下,经80分钟添加链调节剂溶液,经90分钟添加单体共进料,且经95分钟添加引发剂共进料。制备溶解于10.0g去离子水中的0.53g过硫酸钠的两种追加剂溶液并将其添加到分开的注射器中。引发剂共进料完成后10分钟,添加第一追加剂溶液。经5分钟将第一追加剂溶液添加到釜中,接着保持10分钟。在这一保持完成后,经5分钟添加第二追加剂溶液,接着保持另外的10分钟。
在使用空气流冷却反应器的同时,以使反应温度维持在60℃以下的速率经由加料漏斗将100g的50%氢氧化钠添加到釜中。将过氧化氢(1.0g的35%溶液)作为清除剂添加到釜中。10分钟后,以使反应温度维持在60℃以下的速率经由加料漏斗将202g的50%氢氧化钠添加到釜中。将去离子水(90.0g)作为最终冲洗液添加到漏斗中。接着将内含物冷却并包装。
最终产物的固体含量为41.22%,pH为6.52,粘度为2880cP。残余的AA含量为23ppmw。重量平均分子量和数目平均分子量分别为39150g/mol和8527g/mol。
实例8和9可由本领域技术人员基本上如上文针对实例7所描述的方法制备,其中可对试剂和条件进行适当的修改。
聚合物分子量.分子量可以使用已知方法,举例来说用以下典型参数通过凝胶渗透色谱法(GPC)来测量:
分析参数:
仪器:具有等度泵、真空脱气器、可变注射大小自动进样器和柱温箱或等效物的安捷伦(Agilent)1100HPLC系统。
检测器:安捷伦1100HPLC G1362A折射率检测器或等效物。
软件:安捷伦化学工作站(Agilent ChemStation),B.04.03版,以及安捷伦GPC-Addon B.01.01版。
柱组:东曹生命科学(TOSOH Bioscience)TSKgel G2500PWxl 7.8mm IDX30cm,7μm色谱柱(P/N 08020)以及东曹生命科学TSKgel GMPWxl 7.8mm IDX30cm,13μm(P/N 08025)。
方法参数:
流动相:在MilliQ HPLC水中的20mM磷酸盐缓冲液,pH约7.0。
流动速率:1.0ml/分钟
注射体积:20μL
色谱柱温度:35℃
运行时间:30分钟
标准品和样品:
标准品:聚丙烯酸,Mp 216到Mp 1,100,000的钠盐。来自美国聚合物标准品公司(American Polymer Standards)的Mp 900到Mp 1,100,000的标准品。
校准:使用安捷伦GPC-Addon软件进行多项式拟合(使用多项式4)。
注射浓度:1-2mg固体/mL 20mM GPC流动相稀释剂。用于标准品和样品二者。
样品浓度:
通常,将10mg样品到5mL 20mM AQGPC流动相溶液中。
流动标记物:30mM磷酸盐
溶液制备:
流动相:流动相:称出14.52g磷酸二氢钠(NaH2PO4)和14.08g磷酸氢二钠(Na2HPO4)。溶解到11L的MilliQ HPLC水中,搅拌以完全溶解所有固体。在溶解完成之后,用0.5N氢氧化钠将溶液调节到pH 7。此溶液用于经由固定体积移液管的流动相和样品/标准品的制备。
流动标记物:按重量计,混合等量的固体Na2HPO4和NaH2PO4。使用充分掺混的混合物,称重1.3克,并溶解到1升的20mM AQGPC流动相混合物中。
抗再沉积测试:
使用以下表2中描述的单元比率制备清洁剂基础配制物。
表2.
1直链烷基苯磺酸盐,斯泰潘公司(Stepan Co.)
2直链脂肪醇醚硫酸盐,斯泰潘公司
在以每分钟90次循环搅拌的去污测试仪(Terg-o-tometer)7243ES型(6x1L井筒)中评定抗再沉积(ARD)性能。配制物详情和测量条件描述于表3中。
表3.
*所有去污测试仪运行均包括无聚合物对照物(no-polymer control)且均包括ACUSOLTM445N分散剂聚合物基准
对个别织物进行标记并且在亨特(Hunter)ColorQuest XE色度计上测量基线白度指数(WI)。将清洁剂、聚合物和污垢添加到每个去污测试仪的盆中,并搅拌大约30秒,以确保清洁剂和聚合物的均质溶液以及污垢的均匀分散。接着根据上述条件将织物加入洗涤槽池中,洗涤并冲洗。一旦冲洗循环完成,则将织物在内部通风的干燥器(约50℃)中干燥。测量洗涤后织物的白度指数,并平均化每盆添加的每种类型的两块布的白度指数。WI值更接近原始布料的WI值指示性能更好。本发明聚合物的性能对照PAA的性能进行了基准测试。结果示于表4、表5,
表4.
a比较实例;b本发明实例
表5.
a比较实例;b本发明实例
表6
a比较实例;b本发明实例
表7.
a比较实例;b本发明实例
表8.
a比较实例;b本发明实例
在表4、表5、表7和表8中的数据显示,实例1-5和实例7-9最能够维持一定范围的布料类型的原始白度,如存在污垢时洗涤前后白度指数的较小变化所证明。
Claims (9)
1.一种洗衣清洁剂组合物,其包含抗再沉积剂、表面活性剂,和任选地助洗剂,其中所述抗再沉积剂是包含以下聚合单元的聚合物:(a)5wt%到40wt%的具有至少一个6到11.5的pKa值的至少一种含氮烯系不饱和单体,和(b)60wt%到95wt%的至少一种烯系不饱和羧酸单体。
2.根据权利要求1所述的组合物,其中至少一种含氮烯系不饱和单体具有至少一个7到11的pKa值。
3.根据权利要求2所述的组合物,其中所述聚合物包含以下聚合单元:5wt%到40wt%的至少一种包含叔氨基的烯系不饱和单体和60wt%到95wt%的至少一种C3-C8烯系不饱和羧酸单体。
4.根据权利要求3所述的组合物,其中所述含氮烯系不饱和单体包含二烷氨基烷基。
5.根据权利要求4所述的组合物,其中所述聚合物包含以下聚合单元:5wt%到35wt%的至少一种二(C1-C4烷基)氨乙基或二(C1-C4烷基)氨丙基(甲基)丙烯酸酯或(甲基)丙烯酰胺,和65wt%到95wt%的至少一种(甲基)丙烯酸。
6.根据权利要求5所述的组合物,其中所述聚合物具有5,000到70,000的Mw。
7.根据权利要求6所述的组合物,其中所述聚合物包含以下聚合单元:7wt%到30wt%的至少一种二(C1-C4烷基)氨乙基或二(C1-C4烷基)氨丙基(甲基)丙烯酸酯或(甲基)丙烯酰胺,和70wt%到93wt%的至少一种(甲基)丙烯酸。
8.根据权利要求7所述的组合物,其中所述表面活性剂包含至少一种是硫酸盐或磺酸盐的阴离子表面活性剂。
9.根据权利要求8所述的组合物,其中所述二(C1-C4烷基)氨乙基或二(C1-C4烷基)氨丙基(甲基)丙烯酸酯或(甲基)丙烯酰胺是甲基丙烯酸2-(二甲氨基)乙酯或N-[3-(二甲氨基)丙基]甲基丙烯酰胺。
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PCT/US2019/023295 WO2019199423A1 (en) | 2018-04-10 | 2019-03-21 | Anti-redeposition additive for laundry detergent |
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