CN111849201A - Macromolecular dye and application thereof in super-concentrated efficient antibacterial laundry gel bead - Google Patents
Macromolecular dye and application thereof in super-concentrated efficient antibacterial laundry gel bead Download PDFInfo
- Publication number
- CN111849201A CN111849201A CN202010752236.6A CN202010752236A CN111849201A CN 111849201 A CN111849201 A CN 111849201A CN 202010752236 A CN202010752236 A CN 202010752236A CN 111849201 A CN111849201 A CN 111849201A
- Authority
- CN
- China
- Prior art keywords
- dye
- parts
- macromolecular
- diol
- diisocyanate
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
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- 239000011324 bead Substances 0.000 title claims abstract description 29
- 230000000844 anti-bacterial effect Effects 0.000 title abstract description 13
- 239000000975 dye Substances 0.000 claims abstract description 51
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims abstract description 40
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 19
- 239000004970 Chain extender Substances 0.000 claims abstract description 14
- 150000002009 diols Chemical class 0.000 claims abstract description 13
- 239000000985 reactive dye Substances 0.000 claims abstract description 12
- 125000005442 diisocyanate group Chemical group 0.000 claims abstract description 9
- 238000002360 preparation method Methods 0.000 claims abstract description 7
- 239000003054 catalyst Substances 0.000 claims abstract description 6
- 230000003385 bacteriostatic effect Effects 0.000 claims abstract description 5
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 5
- 239000002994 raw material Substances 0.000 claims abstract description 4
- 238000006243 chemical reaction Methods 0.000 claims description 20
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 19
- 239000002202 Polyethylene glycol Substances 0.000 claims description 9
- 229920001223 polyethylene glycol Polymers 0.000 claims description 9
- CRVGTESFCCXCTH-UHFFFAOYSA-N methyl diethanolamine Chemical compound OCCN(C)CCO CRVGTESFCCXCTH-UHFFFAOYSA-N 0.000 claims description 7
- -1 adipate diol Chemical class 0.000 claims description 6
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 claims description 6
- 238000003756 stirring Methods 0.000 claims description 6
- 238000001816 cooling Methods 0.000 claims description 5
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 claims description 5
- 238000010008 shearing Methods 0.000 claims description 5
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 claims description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
- 239000005057 Hexamethylene diisocyanate Substances 0.000 claims description 4
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 4
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 claims description 4
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 claims description 4
- 229920001610 polycaprolactone Polymers 0.000 claims description 4
- 229920001451 polypropylene glycol Polymers 0.000 claims description 4
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 claims description 4
- 125000003158 alcohol group Chemical group 0.000 claims description 3
- 239000002981 blocking agent Substances 0.000 claims description 3
- 238000004945 emulsification Methods 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- BJZYYSAMLOBSDY-QMMMGPOBSA-N (2s)-2-butoxybutan-1-ol Chemical compound CCCCO[C@@H](CC)CO BJZYYSAMLOBSDY-QMMMGPOBSA-N 0.000 claims description 2
- JVYDLYGCSIHCMR-UHFFFAOYSA-N 2,2-bis(hydroxymethyl)butanoic acid Chemical compound CCC(CO)(CO)C(O)=O JVYDLYGCSIHCMR-UHFFFAOYSA-N 0.000 claims description 2
- 150000004056 anthraquinones Chemical class 0.000 claims description 2
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 2
- 125000003827 glycol group Chemical group 0.000 claims description 2
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 claims description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 239000000178 monomer Substances 0.000 claims description 2
- 238000006386 neutralization reaction Methods 0.000 claims description 2
- 239000004632 polycaprolactone Substances 0.000 claims description 2
- 239000004417 polycarbonate Substances 0.000 claims description 2
- 229920000515 polycarbonate Polymers 0.000 claims description 2
- 229920000909 polytetrahydrofuran Polymers 0.000 claims description 2
- 229960004063 propylene glycol Drugs 0.000 claims description 2
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 abstract description 3
- 239000004814 polyurethane Substances 0.000 abstract description 3
- 229920002635 polyurethane Polymers 0.000 abstract description 3
- 238000003786 synthesis reaction Methods 0.000 abstract description 3
- 238000005406 washing Methods 0.000 description 15
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 230000000694 effects Effects 0.000 description 10
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 9
- 239000003599 detergent Substances 0.000 description 8
- 239000004094 surface-active agent Substances 0.000 description 8
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 7
- 239000012975 dibutyltin dilaurate Substances 0.000 description 7
- 239000007795 chemical reaction product Substances 0.000 description 6
- 238000012360 testing method Methods 0.000 description 5
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- 239000003086 colorant Substances 0.000 description 4
- 238000005202 decontamination Methods 0.000 description 4
- 230000003588 decontaminative effect Effects 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 230000001954 sterilising effect Effects 0.000 description 4
- 238000004659 sterilization and disinfection Methods 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 239000005058 Isophorone diisocyanate Substances 0.000 description 3
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 3
- 230000009471 action Effects 0.000 description 3
- 239000011259 mixed solution Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 230000002195 synergetic effect Effects 0.000 description 3
- 102000004190 Enzymes Human genes 0.000 description 2
- 108090000790 Enzymes Proteins 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 230000001236 detergent effect Effects 0.000 description 2
- 229940088598 enzyme Drugs 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- WHIVNJATOVLWBW-UHFFFAOYSA-N n-butan-2-ylidenehydroxylamine Chemical compound CCC(C)=NO WHIVNJATOVLWBW-UHFFFAOYSA-N 0.000 description 2
- 230000003472 neutralizing effect Effects 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 229940051841 polyoxyethylene ether Drugs 0.000 description 2
- 229920000056 polyoxyethylene ether Polymers 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- VOXZDWNPVJITMN-ZBRFXRBCSA-N 17β-estradiol Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 VOXZDWNPVJITMN-ZBRFXRBCSA-N 0.000 description 1
- 239000004382 Amylase Substances 0.000 description 1
- 102000013142 Amylases Human genes 0.000 description 1
- 108010065511 Amylases Proteins 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 241000222122 Candida albicans Species 0.000 description 1
- 108010059892 Cellulase Proteins 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- 241000588724 Escherichia coli Species 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical group CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 102000004882 Lipase Human genes 0.000 description 1
- 239000004367 Lipase Substances 0.000 description 1
- 108090001060 Lipase Proteins 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 108091005804 Peptidases Proteins 0.000 description 1
- 239000004365 Protease Substances 0.000 description 1
- 102100037486 Reverse transcriptase/ribonuclease H Human genes 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- 241000191967 Staphylococcus aureus Species 0.000 description 1
- JNGWKQJZIUZUPR-UHFFFAOYSA-N [3-(dodecanoylamino)propyl](hydroxy)dimethylammonium Chemical compound CCCCCCCCCCCC(=O)NCCC[N+](C)(C)[O-] JNGWKQJZIUZUPR-UHFFFAOYSA-N 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 231100000460 acute oral toxicity Toxicity 0.000 description 1
- 150000001412 amines Chemical group 0.000 description 1
- 235000019418 amylase Nutrition 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 230000002421 anti-septic effect Effects 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- 229940095731 candida albicans Drugs 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 229940106157 cellulase Drugs 0.000 description 1
- 235000019864 coconut oil Nutrition 0.000 description 1
- 239000003240 coconut oil Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000007850 fluorescent dye Substances 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 229940026210 lauramidopropylamine oxide Drugs 0.000 description 1
- 235000019421 lipase Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000000691 measurement method Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
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- 210000000214 mouth Anatomy 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
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- 235000019419 proteases Nutrition 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
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- 230000000638 stimulation Effects 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B69/00—Dyes not provided for by a single group of this subclass
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- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G18/3271—Hydroxyamines
- C08G18/3275—Hydroxyamines containing two hydroxy groups
-
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G18/3819—Low-molecular-weight compounds having heteroatoms other than oxygen having nitrogen
- C08G18/3836—Low-molecular-weight compounds having heteroatoms other than oxygen having nitrogen containing azo groups
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
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- C08G18/30—Low-molecular-weight compounds
- C08G18/38—Low-molecular-weight compounds having heteroatoms other than oxygen
- C08G18/3855—Low-molecular-weight compounds having heteroatoms other than oxygen having sulfur
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
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- C08G18/40—High-molecular-weight compounds
- C08G18/48—Polyethers
- C08G18/4833—Polyethers containing oxyethylene units
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G18/65—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
- C08G18/66—Compounds of groups C08G18/42, C08G18/48, or C08G18/52
- C08G18/6666—Compounds of group C08G18/48 or C08G18/52
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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- C08G18/6681—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/32 or C08G18/3271 and/or polyamines of C08G18/38
- C08G18/6688—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/32 or C08G18/3271 and/or polyamines of C08G18/38 with compounds of group C08G18/3271
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B69/00—Dyes not provided for by a single group of this subclass
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B69/00—Dyes not provided for by a single group of this subclass
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- C09B69/103—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds containing a diaryl- or triarylmethane dye
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B69/00—Dyes not provided for by a single group of this subclass
- C09B69/10—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds
- C09B69/109—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds containing other specific dyes
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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
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/66—Non-ionic compounds
- C11D1/825—Mixtures of compounds all of which are non-ionic
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- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D17/00—Detergent materials or soaps characterised by their shape or physical properties
- C11D17/04—Detergent materials or soaps characterised by their shape or physical properties combined with or containing other objects
- C11D17/041—Compositions releasably affixed on a substrate or incorporated into a dispensing means
- C11D17/042—Water soluble or water disintegrable containers or substrates containing cleaning compositions or additives for cleaning compositions
- C11D17/043—Liquid or thixotropic (gel) compositions
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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
- C11D3/02—Inorganic compounds ; Elemental compounds
- C11D3/12—Water-insoluble compounds
- C11D3/1206—Water-insoluble compounds free metals, e.g. aluminium grit or flakes
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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
- C11D3/20—Organic compounds containing oxygen
- C11D3/2003—Alcohols; Phenols
- C11D3/2065—Polyhydric alcohols
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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
- C11D3/38—Products with no well-defined composition, e.g. natural products
- C11D3/386—Preparations containing enzymes, e.g. protease or amylase
- C11D3/38618—Protease or amylase in liquid compositions only
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- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/40—Dyes ; Pigments
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Abstract
The invention discloses a macromolecular dye which is prepared from the following raw materials in parts by weight: 30-70 parts of macromolecular diol, 15-50 parts of diisocyanate, 6-15 parts of hydrophilic chain extender, 0.1-11 parts of diol chain extender, 0.1-11 parts of reactive dye, 0.01-0.08 part of catalyst, 20-200 parts of acetone, 2-11 parts of end-capping agent, 4-11 parts of neutralizer and 400 parts of water 200-. Also discloses a preparation method of the macromolecular dye and application of the macromolecular dye in super-concentrated efficient bacteriostatic laundry beads. The prepared super-concentrated efficient antibacterial laundry gel bead is rich in color and bright in color light, the molecular weight of the modified dye exceeds more than ten thousand, no harm is caused to organisms, and meanwhile, the macromolecular dye prepared by the waterborne polyurethane synthesis technology has high water solubility.
Description
Technical Field
The invention relates to the technical field of daily chemical industry, in particular to a macromolecular dye, a preparation method thereof and application thereof in an ultra-concentrated efficient antibacterial laundry bead.
Background
The cleaning of clothes and textiles is always a problem in people's life, and with the development of living standard and economy, the clothes washing products are continuously upgraded from the initial washing soap to washing powder to the washing liquid to the current washing condensation beads, so as to improve the demands of consumers, reduce the waste of resources and reduce the environmental pollution. The traditional washing powder uses anhydrous sodium sulphate as a filler in a large amount, has no effect and wastes resources. The appearance of the laundry detergent replaces anhydrous sodium sulphate with water, so that resources are saved, and the production process of the laundry detergent is simple. However, the decontamination and sterilization effects of the laundry detergent are difficult, too much addition is not beneficial to the cost saving of consumers, too little addition can not achieve the decontamination effect, so that the laundry detergent can be condensed into a laundry detergent with several times, the use amount is small, the operation is simple, one bead can be used for washing one barrel of clothes, and the washing process is convenient and fast. However, most of the clothes cleaning and caring in the market add coloring agent to mask the color of the clothes or play a role in attracting the eyes of consumers. These colors are typically small molecule dyes or fluorescent dyes.
The small molecular dye usually migrates to clothes to dye the clothes, so the addition amount in daily use chemicals is extremely low, and meanwhile, the small molecular dye can cause harm to water bodies to cause the risks of death of water body organisms and the like. Therefore, there is a need to develop a non-staining, highly water-soluble and bio-environmentally friendly dye to solve the above problems.
Disclosure of Invention
The invention aims to solve the technical problem of providing a macromolecular dye and an application thereof in a super-concentrated high-efficiency antibacterial laundry gel bead, wherein the prepared super-concentrated high-efficiency antibacterial laundry gel bead is rich in color and bright in color light, the molecular weight of the modified dye exceeds more than ten thousand, no harm is caused to organisms, and the macromolecular dye prepared by the waterborne polyurethane synthesis technology has high water solubility.
In order to solve the technical problems, the invention adopts a technical scheme that: the macromolecular dye is prepared from the following raw materials in parts by weight: 30-70 parts of macromolecular diol, 15-50 parts of diisocyanate, 6-15 parts of hydrophilic chain extender, 0.1-11 parts of diol chain extender, 0.1-11 parts of reactive dye, 0.01-0.08 part of catalyst, 20-200 parts of acetone, 2-11 parts of end-capping agent, 4-11 parts of neutralizer and 400 parts of water 200-.
In a preferred embodiment of the present invention, the macrodiol is selected from one or more of polyethylene glycol (PEG), polytetrahydrofuran ether glycol (PTMG), polypropylene glycol (PPG), polyethylene glycol adipate diol (PEA), poly-1, 4-butylene glycol adipate diol (PBA), poly-neopentyl glycol adipate diol (PMA), polycaprolactone diol (PCL), polycarbonate diol (PCDL).
In a preferred embodiment of the present invention, the diisocyanate is selected from one or more of isophorone diisocyanate (IPDI), Toluene Diisocyanate (TDI), Hexamethylene Diisocyanate (HDI), diphenylmethane diisocyanate (MDI), 4' -dicyclohexylmethane diisocyanate (HMDI).
In a preferred embodiment of the present invention, the hydrophilic chain extender is one of N-Methyldiethanolamine (MDEA), 2-dimethylolpropionic acid (DMPA) and 2, 2-dimethylolbutyric acid (DMBA).
In a preferred embodiment of the present invention, the glycol chain extender is selected from one or more of Ethylene Glycol (EG), 1, 2-propylene glycol (MPD), 1, 4-Butanediol (BDO), neopentyl glycol (NPG), 1, 6-Hexanediol (HDO), diethylene glycol (DEG).
In a preferred embodiment of the present invention, the reactive DYE monomer is selected from one or a combination of several of the following structural formulas DYE 1-DYE 3:
DYE 1: azo compounds;
DYE 2: anthraquinones;
DYE 3: triarylmethanes.
Further, R1 is CH3、Cl、OCH3、NaSO3R2 is CH3One of Cl, R3 and R4 are OH and CH3And CN.
In a preferred embodiment of the invention, the catalyst is selected from the group consisting of organotins, organobismuth species, and preferably dibutyltin dilaurate.
In a preferred embodiment of the present invention, the blocking agent is selected from one or more of Methyl Ethyl Ketoxime (MEKO), Phenol (PH), and sodium bisulfite (SHS).
In a preferred embodiment of the invention, the neutralizing agent is selected from amine neutralizing agents, such as triethylamine.
In order to solve the technical problem, the invention adopts another technical scheme that: the preparation method of the super-concentrated high-efficiency antibacterial macromolecular dye for the laundry gel bead comprises the following steps:
step 1: dehydrating the macromolecular diol at the temperature of 100-120 ℃ for 0.5-1.5 hours;
step 2: adding reactive dye and diisocyanate, and reacting at 80-90 deg.C for 2-4 hr;
and step 3: adding a micromolecular dihydric alcohol chain extender, a catalyst and a solvent acetone, and reacting for 1-4 hours at 70-80 ℃;
and 4, step 4: cooling to 40-50 ℃, and dropwise adding an acetone solution of a hydrophilic chain extender into the reaction solution; controlling the dripping time to be 0.5-1 hour, and keeping the temperature of 50-70 ℃ for reacting for 2-5 hours after dripping; adding a blocking agent to react for 0.5 to 4 hours at the temperature of between 40 and 85 ℃;
and 5: cooling to 0-40 deg.C, adding neutralizer for neutralization, reacting for 1-5 min, adding water under high-speed shearing and stirring (rotation speed up to 1200r/min) for emulsification, stirring for reaction for 5-30 min, and removing acetone under vacuum condition of 40-50 deg.C and 0.01MPa to obtain macromolecular dye.
The invention also provides an application of the macromolecular dye in the super-concentrated efficient antibacterial laundry bead.
In a preferred embodiment of the invention, the super-concentrated high-efficiency bacteriostatic laundry bead comprises the following components in percentage by mass:
further, the surfactant comprises one or more of fatty alcohol-polyoxyethylene ether, modified thickening fatty alcohol-polyoxyethylene ether, lauramidopropyl amine oxide and coconut oil fatty acid diethanolamide. The surfactant is classified as anionic, cationic and nonionic, and has different action mechanisms on different kinds of dirt, so that the synergistic action is larger than that of a single surfactant.
Further, the polyol is one of ethylene glycol, glycerol or sorbitol.
Furthermore, the enzyme is a mixture of more than two of protease, amylase, lipase or cellulase in equal mass ratio.
Further, the preservative is cason.
Further, the colorant is the macromolecular dye prepared by the invention.
Furthermore, the nano-silver is an efficient bactericide, can sterilize durably, has no stimulation to skin, and cannot influence the stability of a system.
Further, the preparation steps of the super-concentrated efficient bacteriostatic laundry gel bead are as follows: stirring deionized water, surfactant and polyalcohol at 40-60 deg.C, cooling to room temperature, adding enzyme, essence, antiseptic, nano silver and colorant, stirring, filtering, detecting, and filling with machine. To obtain the washing gel bead.
The invention has the beneficial effects that:
(1) in the raw material composition and preparation of the macromolecular dye, diisocyanate is firstly utilized to react with dihydric alcohol, and a reactive dye structure is also a dihydric alcohol structure, so that the reactive dye can be used as a reactive substance to react with the diisocyanate, chain extension is carried out, and an external emulsification method is carried out after the reaction is carried out to a certain degree to obtain polyurethane emulsion, namely the macromolecular dye; by utilizing a polymer synthesis technology, the reactive small molecular dye is grafted onto a polymer system, so that on one hand, high water solubility can be realized, and on the other hand, the obtained large molecular dye is bright in color, high in permeability and free of pollution to a water body;
(2) macromolecular dye is added into the washing gel beads, so that the color is bright, the stability of the system is not influenced, the water washed out cannot pollute the water body when being discharged into a sewer, and the biological environment is protected;
(3) the washing gel bead of the invention obtains the detergency effect which is 8 times of the standard detergency effect by utilizing the synergistic principle of the surfactant, and has the effects of high-efficiency decontamination and energy saving; the synergistic principle refers to the phenomenon that after different types of surfactants are mixed with each other, the surfactants respectively play different action mechanisms, so that better washing and decontamination effects are generated compared with the effect of singly using one of the surfactants;
(4) the nano silver is added into the washing gel bead, so that the stability of the system is not influenced, and meanwhile, the washing gel bead has high-efficiency sterilization and bacteriostasis effects, and the sterilization rate is as high as more than 99%;
(5) the macromolecular dye and the washing gel bead have simple preparation process and controllable cost.
Detailed Description
The following detailed description of the preferred embodiments of the present invention is provided to enable those skilled in the art to more readily understand the advantages and features of the present invention, and to clearly and unequivocally define the scope of the present invention.
Example 1:
50 g of PEG (Mn 2000) is dehydrated at 110 ℃ for 0.5-1.5 hours, 0.9 g of yellow reactive DYE DYE1 dissolved by acetone and 28 g of IPDI are added, 0.7 g of BDO is added after the reaction at 90 ℃ for 4 hours, 1 drop of dibutyltin dilaurate (DBTDL) and 30mL of acetone are added, the reaction is carried out at 70 ℃ for 2 hours, then a mixed solution of 8.9 g of MDEA and 30mL of acetone is added dropwise at 50 ℃, the dropping is finished within 0.5-1 hour, the reaction is kept at 65 ℃ for 3 hours after the dropping is finished, 0.8 g of phenol is added for the reaction at 85 ℃ for 3 hours, then the temperature is reduced to room temperature, 4.5 g of triethylamine is added for the reaction for 1-5 minutes, 208mL of water is added under high-speed shearing, the reaction product is stirred for 5-30 minutes, the acetone solvent of the reaction product is removed under the vacuum condition of 45 ℃ and 0.01MPa, and the yellow macromolecular DYE 1.5 # is obtained.
Example 2:
50 g of PEG (Mn 2000) is dehydrated at 110 ℃ for 0.5 to 1.5 hours, 0.7 g of red reactive DYE DYE2 dissolved by acetone and 28 g of IPDI are added, 0.7 g of BDO is added after the reaction at 90 ℃ for 4 hours, 1 drop of dibutyltin dilaurate (DBTDL) and 30mL of acetone are added, the reaction is carried out at 70 ℃ for 2 hours, then a mixed solution of 8.9 g of MDEA and 30mL of acetone is added dropwise at 50 ℃, the dropping is finished within 0.5 to 1 hour, the reaction is kept at 65 ℃ for 3 hours after the dropping is finished, 0.8 g of phenol is added for reaction at 85 ℃ for 3 hours, then the temperature is reduced to room temperature, 4.5 g of triethylamine is added for reaction for 1 to 5 minutes, 208mL of water is added under high-speed shearing, after the reaction product is stirred for 5 to 30 minutes, the acetone solvent of the reaction product is removed under the vacuum condition of 45 ℃ and 0.01MPa, and the red macromolecular DYE2 is obtained.
Example 3:
50 g of PEG (Mn 2000) is dehydrated at 110 ℃ for 0.5 to 1.5 hours, 0.7 g of acetone-dissolved blue reactive DYE DYE3 and 28 g of IPDI are added, after the reaction at 90 ℃ for 4 hours, 0.7 g of BDO is added, 1 drop of dibutyltin dilaurate (DBTDL) and 30mL of acetone are added, the reaction is carried out at 70 ℃ for 2 hours, then a mixed solution of 8.9 g of MDEA and 30mL of acetone is added dropwise at 50 ℃, the dropwise addition is completed within 0.5 to 1 hour, after the dropwise addition, the reaction is kept at 65 ℃ for 3 hours, 0.8 g of phenol is added for reaction at 85 ℃ for 3 hours, then the temperature is reduced to room temperature, 4.5 g of triethylamine is added for reaction for 1 to 5 minutes, 208mL of water is added under high-speed shearing, after the reaction product is stirred for 5 to 30 minutes, the solvent acetone is removed from the reaction product under the vacuum condition of 45 ℃ and 0.01MPa, and the blue macromolecular DYE 3..
The application example is as follows:
and (3) result and detection:
the application examples 1 to 4 of the present invention were uniformly stirred, filtered and filled to obtain laundry beads, the laundry beads were diluted 8 times with water, and then the detergency was measured by the detergency measurement method in the QB/T1224-2012 clothing liquid detergent standard, table 1 shows the detergency test results, and the results are as follows:
TABLE 1
As can be seen from Table 1, the detergent effect of the laundry bead of the present invention is 8 times that of the laundry detergent, which means that the laundry bead is a product with high detergent efficiency, and the detergent effect is 2-4 times higher than that of the laundry beads sold on the market.
Performing a sterilization experiment according to QB/T2738-: 100, the test action time is 20 minutes. Table 2 shows the results of the bactericidal effect test.
TABLE 2
| Numbering | Staphylococcus aureus | Candida albicans | Escherichia coli |
| Application example 1 | 99.1％ | 99.2％ | 99.5％ |
| Application example 2 | 99.3％ | 99.4％ | 99.5％ |
| Application example 3 | 99.5％ | 99.3％ | 99.3％ |
| Application example 4 | 99.3％ | 99.2％ | 99.3％ |
| Commercially available beads | 89％ | 85％ | 86％ |
As can be seen from Table 2, the laundry beads obtained in the application example of the present invention have good bactericidal effects on three kinds of bacteria, which indicates that the laundry beads have excellent bactericidal and antibacterial effects.
Examples 1-3 were subjected to acute oral test by OECD420-2001
The experimental steps are as follows: the mice were randomly selected and grouped, fasted for 16 hours before the test, and fed at a feeding dose of 2g/kg by a one-time limiting method, observed twice a day, weighed once every three days, and observed for 14 days in total. Table 3 shows the experimental results of acute oral toxicity of macromolecular dye to rat, which are as follows:
TABLE 3
As can be seen from Table 3, the macromolecular dye was not harmful to the oral cavity of rats. The macromolecular dye has good biological environmental protection effect.
Although the present invention has been described in detail with reference to the foregoing embodiments, it will be apparent to those skilled in the art that changes may be made in the embodiments and/or equivalents thereof without departing from the spirit and scope of the invention. Any modification, equivalent replacement, or improvement made within the spirit and principle of the present invention should be included in the protection scope of the present invention.
Claims (10)
1. The macromolecular dye is characterized by being prepared from the following raw materials in parts by weight: 30-70 parts of macromolecular diol, 15-50 parts of diisocyanate, 6-15 parts of hydrophilic chain extender, 0.1-11 parts of diol chain extender, 0.1-11 parts of reactive dye, 0.01-0.08 part of catalyst, 20-200 parts of acetone, 2-11 parts of end-capping agent, 4-11 parts of neutralizer and 400 parts of water 200-.
2. The macromolecular dye according to claim 1, characterized in that said macromolecular diol is selected from one or more of polyethylene glycol (PEG), polytetrahydrofuran ether glycol (PTMG), polypropylene glycol (PPG), polyethylene glycol adipate diol (PEA), poly-1, 4-butylene glycol adipate diol (PBA), poly-neopentyl glycol adipate diol (PMA), polycaprolactone diol (PCL), polycarbonate diol (PCDL).
3. Macromolecular dye according to claim 1, characterized in that said diisocyanate is selected from one or more of isophorone diisocyanate (IPDI), Toluene Diisocyanate (TDI), Hexamethylene Diisocyanate (HDI), diphenylmethane diisocyanate (MDI), 4' -dicyclohexylmethane diisocyanate (HMDI).
4. The macromolecular dye according to claim 1, characterized in that said hydrophilic chain extender is one of N-Methyldiethanolamine (MDEA), 2-dimethylolpropionic acid (DMPA) and 2, 2-dimethylolbutyric acid (DMBA).
5. The macromolecular dye according to claim 1, characterized in that said glycol chain extender is selected from one or more of Ethylene Glycol (EG), 1, 2-propylene glycol (MPD), 1, 4-Butanediol (BDO), neopentyl glycol (NPG), 1, 6-Hexanediol (HDO), diethylene glycol (DEG).
6. The macromolecular DYE according to claim 1, characterized in that said reactive DYE monomers are selected from one or a combination of several of the following structural formulae DYE 1-DYE 3:
DYE 1: azo compounds;
DYE 2: anthraquinones;
DYE 3: triarylmethanes.
7. The macromolecular dye according to claim 6, characterized in that R1 is CH3、Cl、OCH3、NaSO3And one of H, R2 is CH3One of Cl and H, R3 and R4 are OH and CH3CN and H.
8. A process for the preparation of a macromolecular dye according to any of claims 1 to 7, characterized in that it comprises the following steps:
step 1: dehydrating the macromolecular diol at the temperature of 100-120 ℃ for 0.5-1.5 hours;
step 2: adding reactive dye and diisocyanate, and reacting at 80-90 deg.C for 2-4 hr;
and step 3: adding a micromolecular dihydric alcohol chain extender, a catalyst and acetone, and reacting for 1-4 hours at 70-80 ℃;
and 4, step 4: cooling to 40-50 ℃, and dropwise adding an acetone solution of a hydrophilic chain extender into the reaction solution; controlling the dripping time to be 0.5-1 hour, and keeping the temperature of 50-70 ℃ for reacting for 2-5 hours after dripping; adding a blocking agent to react for 0.5 to 4 hours at the temperature of between 40 and 85 ℃;
and 5: cooling to 0-40 deg.C, adding neutralizer for neutralization, reacting for 1-5 min, adding water under high-speed shearing and stirring for emulsification, stirring for reaction for 5-30 min, and removing acetone at 40-50 deg.C under 0.01MPa vacuum to obtain macromolecular dye.
9. Use of a macromolecular dye according to any one of claims 1 to 7 in an ultra-concentrated high performance bacteriostatic laundry bead.
10. The use according to claim 9, wherein the ultra-concentrated high-efficiency bacteriostatic laundry bead comprises the following components in percentage by mass:
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| CN114573466A (en) * | 2022-03-02 | 2022-06-03 | 安徽大学 | Red anthraquinone compound and application thereof |
| CN115677974A (en) * | 2022-11-16 | 2023-02-03 | 南宝树脂（佛山）有限公司 | Anti-color-migration mesh surface treating agent and preparation method thereof |
| CN118638436A (en) * | 2024-08-12 | 2024-09-13 | 浙江材华科技有限公司 | Macromolecular dye compound, preparation method thereof and daily chemical product |
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| CN114573466B (en) * | 2022-03-02 | 2024-03-22 | 安徽大学 | Red anthraquinone compound and application thereof |
| CN115677974A (en) * | 2022-11-16 | 2023-02-03 | 南宝树脂（佛山）有限公司 | Anti-color-migration mesh surface treating agent and preparation method thereof |
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