CN116515052A - Water-soluble dispersing agent and preparation method and application thereof - Google Patents
Water-soluble dispersing agent and preparation method and application thereof Download PDFInfo
- Publication number
- CN116515052A CN116515052A CN202310527883.0A CN202310527883A CN116515052A CN 116515052 A CN116515052 A CN 116515052A CN 202310527883 A CN202310527883 A CN 202310527883A CN 116515052 A CN116515052 A CN 116515052A
- Authority
- CN
- China
- Prior art keywords
- water
- polyether
- parts
- dispersing agent
- sultone
- 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.)
- Granted
Links
- 239000002270 dispersing agent Substances 0.000 title claims abstract description 61
- 238000002360 preparation method Methods 0.000 title claims abstract description 48
- 239000004721 Polyphenylene oxide Substances 0.000 claims abstract description 87
- 229920000570 polyether Polymers 0.000 claims abstract description 87
- 229920000642 polymer Polymers 0.000 claims abstract description 68
- 239000000178 monomer Substances 0.000 claims abstract description 59
- NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical compound OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 claims abstract description 32
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims abstract description 28
- 229920002647 polyamide Polymers 0.000 claims abstract description 21
- 239000002994 raw material Substances 0.000 claims abstract description 16
- 239000004952 Polyamide Substances 0.000 claims abstract description 14
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims abstract description 8
- 229920001577 copolymer Polymers 0.000 claims abstract description 5
- 229920001519 homopolymer Polymers 0.000 claims abstract description 3
- 238000006243 chemical reaction Methods 0.000 claims description 37
- 238000003756 stirring Methods 0.000 claims description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 16
- -1 alkyl sultone Chemical class 0.000 claims description 14
- 238000004321 preservation Methods 0.000 claims description 11
- 239000008367 deionised water Substances 0.000 claims description 10
- 229910021641 deionized water Inorganic materials 0.000 claims description 10
- 238000010438 heat treatment Methods 0.000 claims description 10
- 239000003999 initiator Substances 0.000 claims description 10
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 9
- WUMMIJWEUDHZCL-UHFFFAOYSA-N 3-prop-2-enyloxolane-2,5-dione Chemical compound C=CCC1CC(=O)OC1=O WUMMIJWEUDHZCL-UHFFFAOYSA-N 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 7
- FSSPGSAQUIYDCN-UHFFFAOYSA-N 1,3-Propane sultone Chemical compound O=S1(=O)CCCO1 FSSPGSAQUIYDCN-UHFFFAOYSA-N 0.000 claims description 6
- WTFAGPBUAGFMQX-UHFFFAOYSA-N 1-[2-[2-(2-aminopropoxy)propoxy]propoxy]propan-2-amine Chemical compound CC(N)COCC(C)OCC(C)OCC(C)N WTFAGPBUAGFMQX-UHFFFAOYSA-N 0.000 claims description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 6
- 239000003377 acid catalyst Substances 0.000 claims description 6
- 238000001816 cooling Methods 0.000 claims description 6
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 6
- 239000011261 inert gas Substances 0.000 claims description 6
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 6
- 150000001412 amines Chemical class 0.000 claims description 5
- 239000001273 butane Substances 0.000 claims description 5
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 4
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- 239000006185 dispersion Substances 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 238000002156 mixing Methods 0.000 claims description 4
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 claims description 3
- NVZWEEGUWXZOKI-UHFFFAOYSA-N 1-ethenyl-2-methylbenzene Chemical compound CC1=CC=CC=C1C=C NVZWEEGUWXZOKI-UHFFFAOYSA-N 0.000 claims description 3
- JZHGRUMIRATHIU-UHFFFAOYSA-N 1-ethenyl-3-methylbenzene Chemical compound CC1=CC=CC(C=C)=C1 JZHGRUMIRATHIU-UHFFFAOYSA-N 0.000 claims description 3
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 claims description 3
- QZPSOSOOLFHYRR-UHFFFAOYSA-N 3-hydroxypropyl prop-2-enoate Chemical compound OCCCOC(=O)C=C QZPSOSOOLFHYRR-UHFFFAOYSA-N 0.000 claims description 3
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 claims description 3
- BJSKBZUMYQBSOQ-UHFFFAOYSA-N Jeffamine M-600 Chemical compound COCCOCC(C)OCC(C)OCC(C)OCC(C)OCC(C)OCC(C)OCC(C)OCC(C)OCC(C)N BJSKBZUMYQBSOQ-UHFFFAOYSA-N 0.000 claims description 3
- 229920001531 copovidone Polymers 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 229930015698 phenylpropene Natural products 0.000 claims description 3
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 claims description 3
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 claims description 3
- 235000019260 propionic acid Nutrition 0.000 claims description 3
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims description 3
- OGMSGZZPTQNTIK-UHFFFAOYSA-N 1-methyl-2-prop-1-en-2-ylbenzene Chemical compound CC(=C)C1=CC=CC=C1C OGMSGZZPTQNTIK-UHFFFAOYSA-N 0.000 claims description 2
- IEVADDDOVGMCSI-UHFFFAOYSA-N 2-hydroxybutyl 2-methylprop-2-enoate Chemical compound CCC(O)COC(=O)C(C)=C IEVADDDOVGMCSI-UHFFFAOYSA-N 0.000 claims description 2
- GNSFRPWPOGYVLO-UHFFFAOYSA-N 3-hydroxypropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCO GNSFRPWPOGYVLO-UHFFFAOYSA-N 0.000 claims description 2
- VWEYDBUEGDKEHC-UHFFFAOYSA-N 3-methyloxathiolane 2,2-dioxide Chemical compound CC1CCOS1(=O)=O VWEYDBUEGDKEHC-UHFFFAOYSA-N 0.000 claims description 2
- ZZLCFHIKESPLTH-UHFFFAOYSA-N 4-Methylbiphenyl Chemical compound C1=CC(C)=CC=C1C1=CC=CC=C1 ZZLCFHIKESPLTH-UHFFFAOYSA-N 0.000 claims description 2
- NDWUBGAGUCISDV-UHFFFAOYSA-N 4-hydroxybutyl prop-2-enoate Chemical compound OCCCCOC(=O)C=C NDWUBGAGUCISDV-UHFFFAOYSA-N 0.000 claims description 2
- YGTVWCBFJAVSMS-UHFFFAOYSA-N 5-hydroxypentyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCCCO YGTVWCBFJAVSMS-UHFFFAOYSA-N 0.000 claims description 2
- INRQKLGGIVSJRR-UHFFFAOYSA-N 5-hydroxypentyl prop-2-enoate Chemical compound OCCCCCOC(=O)C=C INRQKLGGIVSJRR-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 2
- QROGIFZRVHSFLM-QHHAFSJGSA-N [(e)-prop-1-enyl]benzene Chemical compound C\C=C\C1=CC=CC=C1 QROGIFZRVHSFLM-QHHAFSJGSA-N 0.000 claims description 2
- 238000007334 copolymerization reaction Methods 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- MHYFEEDKONKGEB-UHFFFAOYSA-N oxathiane 2,2-dioxide Chemical compound O=S1(=O)CCCCO1 MHYFEEDKONKGEB-UHFFFAOYSA-N 0.000 claims description 2
- 238000006116 polymerization reaction Methods 0.000 claims description 2
- 239000001294 propane Substances 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
- 230000035484 reaction time Effects 0.000 claims description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 2
- 229920002554 vinyl polymer Polymers 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 239000002245 particle Substances 0.000 abstract description 19
- 239000002002 slurry Substances 0.000 abstract description 9
- 238000000227 grinding Methods 0.000 abstract description 6
- 238000009736 wetting Methods 0.000 abstract description 5
- 230000002633 protecting effect Effects 0.000 abstract description 4
- 239000000975 dye Substances 0.000 description 31
- 230000000052 comparative effect Effects 0.000 description 15
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 238000012360 testing method Methods 0.000 description 10
- 239000011259 mixed solution Substances 0.000 description 9
- 238000004043 dyeing Methods 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 238000001556 precipitation Methods 0.000 description 8
- 239000000986 disperse dye Substances 0.000 description 7
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000011534 incubation Methods 0.000 description 3
- 229920005610 lignin Polymers 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- 125000000542 sulfonic acid group Chemical group 0.000 description 3
- 239000002351 wastewater Substances 0.000 description 3
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 description 2
- WFUGQJXVXHBTEM-UHFFFAOYSA-N 2-hydroperoxy-2-(2-hydroperoxybutan-2-ylperoxy)butane Chemical compound CCC(C)(OO)OOC(C)(CC)OO WFUGQJXVXHBTEM-UHFFFAOYSA-N 0.000 description 2
- 239000004342 Benzoyl peroxide Substances 0.000 description 2
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 2
- 235000019400 benzoyl peroxide Nutrition 0.000 description 2
- 238000004044 disperse dyeing Methods 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000010526 radical polymerization reaction Methods 0.000 description 2
- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 229920001732 Lignosulfonate Polymers 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 1
- 229920006221 acetate fiber Polymers 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 238000004873 anchoring Methods 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000021615 conjugation Effects 0.000 description 1
- 230000001276 controlling effect Effects 0.000 description 1
- 238000012937 correction Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-M naphthalene-1-sulfonate Chemical compound C1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-M 0.000 description 1
- 238000010606 normalization Methods 0.000 description 1
- 239000003002 pH adjusting agent Substances 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- XFTALRAZSCGSKN-UHFFFAOYSA-M sodium;4-ethenylbenzenesulfonate Chemical compound [Na+].[O-]S(=O)(=O)C1=CC=C(C=C)C=C1 XFTALRAZSCGSKN-UHFFFAOYSA-M 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
Classifications
-
- 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
- C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
- C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
- C08F290/06—Polymers provided for in subclass C08G
- C08F290/062—Polyethers
-
- 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
- C08F212/06—Hydrocarbons
- C08F212/08—Styrene
-
- 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
- C08F212/06—Hydrocarbons
- C08F212/12—Monomers containing a branched unsaturated aliphatic radical or a ring substituted by an alkyl radical
-
- 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
- C08F220/10—Esters
- C08F220/38—Esters containing sulfur
- C08F220/382—Esters containing sulfur and containing oxygen, e.g. 2-sulfoethyl (meth)acrylate
-
- 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
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
- C09B67/0084—Dispersions of dyes
- C09B67/0085—Non common dispersing agents
- C09B67/009—Non common dispersing agents polymeric dispersing agent
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/16—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using dispersed, e.g. acetate, dyestuffs
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/44—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders
- D06P1/52—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders using compositions containing synthetic macromolecular substances
- D06P1/5207—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
- D06P1/5214—Polymers of unsaturated compounds containing no COOH groups or functional derivatives thereof
- D06P1/5242—Polymers of unsaturated N-containing compounds
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/44—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders
- D06P1/52—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders using compositions containing synthetic macromolecular substances
- D06P1/5207—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
- D06P1/525—Polymers of unsaturated carboxylic acids or functional derivatives thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Dispersion Chemistry (AREA)
- Macromonomer-Based Addition Polymer (AREA)
Abstract
The invention provides a water-soluble dispersing agent, a preparation method and application thereof, wherein the water-soluble dispersing agent comprises a polyether modified polymer A and a polyamide high-molecular polymer B; the preparation raw materials of the polyether modified polymer A comprise vinyl benzene monomers, vinyl sulfonic acid monomers and active macromonomer polyether; the polyamide high molecular polymer B comprises a homopolymer of vinyl pyrrolidone and/or a copolymer of vinyl pyrrolidone. The water-soluble dispersing agent provided by the invention improves the wetting and protecting effects of the dispersing agent on dispersing dye particles, so that the grinding efficiency of the dispersing dye, the proportion of the dye particles in the slurry and the stability of the slurry are all improved.
Description
Technical Field
The invention belongs to the technical field of color paste additives, and relates to a water-soluble dispersing agent, a preparation method and application thereof.
Background
The disperse dye is a dye with smaller molecules and no water-soluble groups on the structure, has complete color spectrum, and the dyed product has bright color and excellent indexes, so the disperse dye is widely applied to dyeing of various synthetic fibers, acetate fibers and blended fabrics. It is necessary to disperse the dye uniformly in the dye liquor by means of the dispersing agent during dyeing to dye the fiber such as polyester.
With the rapid development of the industrial printing and dyeing industry in China, the wastewater discharge and pollution degree in the printing and dyeing industry are greatly increased, and the diversification of printing and dyeing products also makes the components in the printing and dyeing wastewater more complex and the treatment more difficult. The traditional disperse dye is added with a large amount of lignin salt, naphthalene sulfonate and other dispersing aids during dispersion, so that the grinding efficiency in the production process is low, the addition amount of the dispersing agent is between 70 and 150 percent of that of the dye, and the high-proportion dispersing agent causes that the printing and dyeing wastewater contains a large amount of organic matters, the treatment process is complicated and has great harm to the environment; and the liquid disperse dyeing paddle is short in stability period and difficult to store for a long time, and the liquid disperse dyeing paddle is required to be sprayed to dry, so that the existing commercial dye in the market is prepared to improve the storage time of the commercial dye.
CN114644762a discloses a multiple modified lignin dye dispersant and a preparation method thereof, industrial alkali lignin is used as a raw material, a sulfonating reagent 1 and a sulfonating reagent 2 are used as a sulfonating reagent system under an alkaline condition, and sulfonic acid groups are simultaneously introduced at different positions, so that the content of hydrophilic group sulfonic acid groups can be greatly improved. Then selectively adding a blocking reagent to reduce the residual hydroxyl content and simultaneously increase the molecular weight. The multi-modified lignin sulfonate can be applied to dye dispersants, can be prepared into a disperse dye system with good dispersibility and excellent high-temperature stability without grinding, has extremely low staining property, has low reduction rate for diazo dye, can obviously improve the dye uptake, and can greatly reduce the production cost of the printing and dyeing industry. However, when the dispersing agent is used for dispersing dye, the adding proportion is higher, and the particle size of the color paste is still larger.
Accordingly, it is desirable in the art to develop a water-soluble dispersant for dye dispersion.
Disclosure of Invention
Aiming at the defects of the prior art, the invention aims to provide a water-soluble dispersing agent, and a preparation method and application thereof. The water-soluble dispersing agent provided by the invention improves the wetting and protecting effects of the dispersing agent on dispersing dye particles, so that the grinding efficiency of the dispersing dye, the proportion of the dye particles in the slurry and the stability of the slurry are all improved.
To achieve the purpose, the invention adopts the following technical scheme:
in a first aspect, the present invention provides a water-soluble dispersant comprising a polyether modified polymer a and a polyamide-based high molecular polymer B;
the preparation raw materials of the polyether modified polymer A comprise vinyl benzene monomers, vinyl sulfonic acid monomers and active macromonomer polyether;
the polyamide high molecular polymer B comprises a homopolymer of vinyl pyrrolidone and/or a copolymer of vinyl pyrrolidone.
The invention is characterized in that a polyether modified polymer A and a polyamide high polymer B are compounded to obtain a water-soluble dispersing agent, wherein the polyether modified polymer A is a comb-shaped polymer obtained by self-made active macromonomer polyether, self-made vinyl sulfonic acid monomer and vinyl benzene monomer through bulk free radical polymerization under the initiation of a peroxide initiator; the reactive macromonomer polyether provides a polymer side chain hydrophilic chain segment, alkyl ester chains and sulfonic acid functional groups contained in the vinyl sulfonic acid monomer endow the polymer with the effects of wetting dye particles and electrostatic repulsion, the conjugation effect of benzene rings of the vinyl benzene monomer improves the affinity of polymer anchoring groups to disperse dye groups, and the application performance of the polymer to disperse dye is regulated and controlled by controlling the proportion of each functional chain segment of the polymer to the corresponding monomer. The compound system of the polyether modified polymer A and the polar polyamide high polymer B enables the types of functional groups of the system of the water-soluble dispersing agent to be diversified, improves the wetting and protecting effects of the dispersing agent on dispersing dye particles, and improves the grinding efficiency of the dispersing dye, the proportion of dye particles in slurry and the stability of the slurry.
Preferably, the reactive macromer polyether is prepared by the following preparation method:
and adding polyether amine and allyl succinic anhydride into a reactor, heating, preserving heat until no water is distilled out in the reaction process, and obtaining the active macromonomer polyether.
Preferably, the polyether amine is a mono-primary amino polyether obtained by taking a monoalcohol as an initiator to initiate ethylene oxide self-polymerization or initiate copolymerization of ethylene oxide and propylene oxide, and the terminal hydroxyl group is converted into amine.
Preferably, the polyetheramine has a weight average molecular weight of 500 to 2500g/mol, e.g. 500g/mol, 800g/mol, 1000g/mol, 1300g/mol, 1500g/mol, 1800g/mol, 2000g/mol, 2300g/mol or 2500g/mol, etc.
Preferably, the polyetheramine comprises any one or a combination of at least two of JEFFAMINE M-2070, JEFFAMINE M-1000 or JEFFAMINE M-600.
Preferably, the molar ratio of polyetheramine to allylsuccinic anhydride is (0.5-1.5): 1, e.g. 0.5:1, 1:1 or 1.5:1, etc., preferably 1:1.
Preferably, the temperature is raised to 120 to 160 ℃, for example 120 ℃, 130 ℃, 140 ℃, 150 ℃, 160 ℃, or the like.
Preferably, the incubation time is 2 to 6 hours, for example 2 hours, 3 hours, 4 hours, 5 hours or 6 hours, etc
Preferably, the preparation of the reactive macromer polyether is carried out under inert gas protection.
Preferably, the reactive macromer polyether has the structure shown in formula I below:
wherein R is 1 Is hydrogen or methyl, R 2 Is methyl, ethyl, propyl or butylM is an integer of 10 to 60, such as 10, 15, 20, 25, 30, 35, 40, 45, 50, 55, or 60, etc., and n is an integer of 0 to 15, such as 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, or 15.
Preferably, the vinylsulfonic acid monomer is prepared by the following preparation method:
adding hydroxylated acrylic monomer and alkyl sultone into a reactor, mixing and reacting until the residual quantity of the alkyl sultone is less than 0.5%, and obtaining the vinyl sulfonic monomer.
In the present invention, the vinyl sulfonic acid monomer is obtained by ring-opening esterification of an acrylic monomer with an alkyl sultone.
Preferably, the hydroxylated acrylic monomer comprises any one or a combination of at least two of hydroxyethyl acrylate, hydroxyethyl methacrylate, hydroxypropyl acrylate, hydroxypropyl methacrylate, hydroxybutyl acrylate, hydroxybutyl methacrylate, hydroxypentyl acrylate or hydroxypentyl methacrylate.
Preferably, the alkyl sultone comprises any one or a combination of at least two of 1, 3-propane sultone, 1-methyl-1, 3-propane sultone, 2-methyl-1, 3-propane sultone, 3-methyl-1, 3-propane sultone, 1, 4-butane sultone, 1-methyl-1, 4-butane sultone, 2-methyl-1, 4-butane sultone, 3-methyl-1, 4-butane sultone or 4-methyl-1, 4-butane sultone.
Preferably, the molar ratio of hydroxylated acrylic monomer to alkyl sultone is 1:1.
Preferably, the system of the reaction also comprises an acid catalyst.
Preferably, the acid catalyst comprises any one or a combination of at least two of p-toluene sulfonic acid, sulfuric acid, propionic acid or hydrochloric acid.
Preferably, the acid catalyst is added in an amount of 0.5% to 3%, for example 0.5%, 1%, 1.5%, 2%, 2.5% or 3%, etc., of the sum of the parts by weight of hydroxylated acrylic monomer and the alkyl sultone.
Preferably, the temperature of the mixing is 60 to 90 ℃, for example 60 ℃,70 ℃, 80 ℃, or 90 ℃, etc.
Preferably, the reaction time is 5 to 20 hours, for example 5 hours, 6 hours, 7 hours, 8 hours, 9 hours, 10 hours, 11 hours, 12 hours, 13 hours, 14 hours, 15 hours, 16 hours, 17 hours, 18 hours, 19 hours, 20 hours, or the like.
Preferably, the preparation process of the vinylsulfonic acid monomer is carried out under the protection of inert gas.
Preferably, the residual quantity of the alkyl sultone is tested by a gas chromatograph, and the sample is detected by a flame ionization detector after being gasified and quantified by a correction area normalization method.
Preferably, the vinylbenzene monomer includes any one or a combination of at least two of styrene, beta-methylstyrene, allylbenzene, 3-methylstyrene, 2-methylstyrene or 2-isopropenyltoluene.
Preferably, the mass ratio of the vinylbenzene monomer, the vinylsulfonic acid monomer and the reactive macromer polyether is (3-10): (10-20): (20-50), such as 3:10:20, 10:20:50, 3:20:20 or 10:10:20, etc.
Preferably, the polyether modified polymer A is prepared from a raw material further comprising an initiator.
Preferably, the initiator comprises any one or a combination of at least two of benzoyl peroxide, t-butyl benzoyl peroxide, methyl ethyl ketone peroxide, dicumyl peroxide, di-t-butyl peroxide or 2, 2-bis (t-butyl peroxide) butane.
Preferably, the polyether modified polymer A is prepared from the following raw materials in parts by weight:
preferably, the raw materials for preparing the polyether modified polymer A are 6 parts, 7 parts, 8 parts, 9 parts, 10 parts, 11 parts, 12 parts, 13 parts, 14 parts, 15 parts, 16 parts, 17 parts, 18 parts, 19 parts or 20 parts by weight of vinyl benzene monomers.
Preferably, the raw materials for preparing the polyether modified polymer A are 20 parts, 21 parts, 22 parts, 23 parts, 24 parts, 25 parts, 26 parts, 27 parts, 28 parts, 29 parts, 30 parts, 31 parts, 32 parts, 33 parts, 34 parts, 35 parts, 36 parts, 37 parts, 38 parts, 39 parts or 40 parts, etc. by weight.
Preferably, the polyether modified polymer A is prepared from 40 parts, 45 parts, 50 parts, 55 parts, 60 parts, 65 parts, 70 parts, 75 parts, 80 parts, 85 parts, 90 parts, 95 parts or 100 parts of active macromonomer polyether by weight.
Preferably, the polyether modified polymer A is prepared from the raw materials in parts by weight, and the initiator can be used in an amount of 0.5 part, 1 part or 1.5 parts, etc.
Preferably, the polyether modified polymer A has a weight average molecular weight of 50000 to 200000g/mol, for example 50000g/mol, 80000g/mol, 100000g/mol, 130000g/mol, 150000g/mol, 180000g/mol or 200000g/mol, etc., preferably 50000 to 100000g/mol.
Preferably, the weight average molecular weight of the polyamide-based high molecular polymer B is 2000 to 100000g/mol, for example 2000g/mol, 5000g/mol, 8000g/mol, 10000g/mol, 30000g/mol, 50000g/mol, 80000g/mol, 100000g/mol, or the like, preferably 10000 to 50000g/mol.
Preferably, the copolymer of vinylpyrrolidone comprises a copolymer of vinylpyrrolidone and vinyl acetate.
Preferably, the polyamide-based high molecular polymer B includes any one or a combination of at least two of PVPK25, PVPK30, PVPK35 or copovidone VA 64.
Preferably, the mass ratio of the polyether modified polymer A to the polyamide-based high molecular polymer B is (60-160) (40-70), such as 60:40, 60:60, 60:70, 100:40, 100:60, 100:70, 160:40, 160:60 or 160:70.
Preferably, deionized water and a pH regulator are also included in the water-soluble dispersing agent.
Preferably, the pH adjuster comprises any one or a combination of at least two of sodium hydroxide, potassium hydroxide, monoethanolamine, diethanolamine or triethanolamine.
Preferably, the water-soluble dispersing agent comprises the following raw materials in parts by weight:
preferably, the polyether modified polymer A is used in an amount of 60 parts, 70 parts, 80 parts, 90 parts, 100 parts, 110 parts, 120 parts, 130 parts, 140 parts, 150 parts or 160 parts by weight of the preparation raw materials of the water-soluble dispersing agent.
Preferably, the water-soluble dispersing agent is prepared from 40 parts by weight, 45 parts by weight, 50 parts by weight, 55 parts by weight, 60 parts by weight, 65 parts by weight or 70 parts by weight of the polyamide high molecular polymer B.
Preferably, the water-soluble dispersing agent is prepared from 100 parts by weight, 110 parts by weight, 120 parts by weight, 130 parts by weight, 140 parts by weight, 150 parts by weight, 160 parts by weight, 170 parts by weight, 180 parts by weight, 190 parts by weight or 200 parts by weight, and the like.
In a second aspect, the present invention provides a method for preparing the water-soluble dispersant of the first aspect, the method comprising the steps of:
(1) Adding reactive macromonomer polyether with formula amount into a reactor, heating, then adding vinyl benzene monomer, vinyl sulfonic acid monomer and optional initiator, and carrying out heat preservation reaction to obtain polyether modified polymer A;
(2) And (3) cooling the polyether modified polymer A obtained in the step (1), then adding optional deionized water and polyamide high molecular polymer B, then adding optional pH regulator, and stirring to obtain the water-soluble dispersing agent.
Preferably, the temperature of step (1) is raised to 100 to 150 ℃, for example, 100 ℃, 110 ℃, 120 ℃, 130 ℃, 140 ℃, 150 ℃, or the like.
Preferably, when the vinylbenzene monomer, the vinylsulfonic acid monomer, and the optional initiator are added in the step (1), the three raw materials are prepared into a mixed solution, and then the mixed solution is added dropwise, and the dropwise adding time is controlled to be 5-15 hours, for example, 5 hours, 6 hours, 7 hours, 8 hours, 9 hours, 10 hours, 11 hours, 12 hours, 13 hours, 14 hours, 15 hours, and the like.
Preferably, the temperature of the incubation reaction in step (1) is 100 to 150 ℃, for example 100 ℃, 110 ℃, 120 ℃, 130 ℃, 140 ℃, 150 ℃, etc., and the incubation reaction is 1 to 3 hours, for example 1 hour, 2 hours, 3 hours, etc.
Preferably, both step (1) and step (2) are carried out under inert gas protection.
Preferably, the cooling in step (2) is to a temperature of 50 to 60 ℃, for example 50 ℃, 55 ℃,60 ℃ or the like.
In a third aspect, the present invention provides the use of a water-soluble dispersant as described in the first aspect in dye dispersion.
Compared with the prior art, the invention has at least the following beneficial effects:
according to the invention, the vinyl benzene monomer, the vinyl sulfonic acid monomer and the active macromonomer polyether are subjected to bulk free radical polymerization to obtain the polyether modified polymer A, the polyether modified polymer A and the polyamide high-molecular polymer B are compounded to obtain the water-soluble dispersing agent, the types of functional groups in the water-soluble dispersing agent system are diversified, the wetting and protecting effects of the dispersing agent on dispersing dye particles are improved, and the grinding efficiency of the dispersing dye, the proportion of dye particles in slurry and the slurry stability are all improved.
Detailed Description
The technical scheme of the invention is further described by the following specific embodiments. It will be apparent to those skilled in the art that the examples are merely to aid in understanding the invention and are not to be construed as a specific limitation thereof.
Preparation example 1
In this preparation example, an active macromer polyether is provided, the preparation method comprising the steps of:
to N 2 200g of polyetheramine JEFFAMINE M-2070 and 14g of allyl succinic anhydride are added into a protected reaction flask, the temperature is raised to 130 ℃, the temperature is kept for 4 hours, no water is distilled out in the reaction process, and the active macromonomer polyether is obtained and is marked as a 1 。
Preparation example 2
In this preparation example, an active macromer polyether is provided, the preparation method comprising the steps of:
to N 2 200g of polyetheramine JEFFAMINE M-1000 and 28g of allyl succinic anhydride are added into a protected reaction flask, the temperature is raised to 140 ℃, the temperature is kept for 3 hours, no water is distilled out in the reaction process, and the active macromonomer polyether is obtained and is marked as a 2 。
Preparation example 3
In this preparation example, an active macromer polyether is provided, the preparation method comprising the steps of:
to N 2 180g of polyetheramine JEFFAMINE M-600 and 42g of allyl succinic anhydride are added into a protected reaction flask, the temperature is raised to 160 ℃, the temperature is kept for 2.5 hours, no water is distilled out in the reaction process, and active macromonomer polyether is prepared and is marked as a 3 。
Preparation example 4
In the preparation example, a vinylsulfonic acid monomer is provided, and the preparation method comprises the following steps:
to N 2 Adding 50g of hydroxyethyl acrylate and 52.6g of 1, 3-propane sultone into a protected reaction flask, uniformly stirring at 60 ℃, then adding 0.6g of p-toluenesulfonic acid, stirring and reacting for 5 hours until the residual quantity of the 1, 3-propane sultone is 0.2%, obtaining the vinyl sulfonic acid monomer, and marking as b 1 。
Preparation example 5
In the preparation example, a vinylsulfonic acid monomer is provided, and the preparation method comprises the following steps:
to N 2 The protected reaction flask was charged with 50g of hydroxypropyl acrylate and 52.3g of 1, 4-butanesulfonic acid lactone, stirring uniformly at 80 ℃, then adding 1g of propionic acid, stirring and reacting for 12 hours until the residual quantity of the 1, 4-butanesulfonic acid lactone is 0.3%, obtaining the vinyl sulfonic acid monomer, and marking as b 2 。
Preparation example 6
In the preparation example, a vinylsulfonic acid monomer is provided, and the preparation method comprises the following steps:
to N 2 Adding 50g of hydroxyethyl methacrylate and 46.9g of 1, 3-propane sultone into a protected reaction flask, uniformly stirring at 90 ℃, adding 2.9g of hydrochloric acid, stirring and reacting for 5 hours until the residual quantity of the 1, 3-propane sultone is 0.4%, obtaining the vinyl sulfonic acid monomer, and marking as b 3 。
Comparative preparation example 1
The comparative preparation differs from preparation 1 only in that allyl succinic anhydride is replaced by an equimolar amount of maleic anhydride, and the polyether obtained is designated D-a 1 。
Example 1
In this embodiment, a water-soluble dispersant is provided, and the preparation method includes the following steps:
(1) To N 2 40 parts by weight of reactive macromer polyether a were added to a protected reaction flask 1 Stirring and heating to 105 ℃; uniformly dropwise adding 20 parts of styrene and 30 parts of vinylsulfonic acid monomer b 1 0.5 part of benzoyl peroxide mixed solution, and after the dropwise addition is completed within 5 hours, carrying out heat preservation reaction for 1.5 hours at 110 ℃ to obtain polyether modified polymer A;
(2) To N 2 And (3) adding 80 parts of the polyether modified polymer A obtained in the step (1) in parts by weight into a protected reaction flask, cooling to 60 ℃, then adding 200 parts of deionized water and 70 parts of PVPK30, then adding potassium hydroxide to adjust the pH value of the system to 7.5, and uniformly stirring to obtain the water-soluble dispersing agent.
Example 2
In this embodiment, a water-soluble dispersant is provided, and the preparation method includes the following steps:
(1) To N 2 60 parts by weight of reactive macromer polyether a were added to a protected reaction flask 2 Stirring and heating to 115 ℃; uniformly dropwise adding 6 parts of styrene and 20 parts of vinylsulfonic acid monomer b 2 0.6 part of mixed solution of benzoyl tert-butyl peroxide, and after the dripping is finished within 15 hours, carrying out heat preservation reaction for 2 hours at 115 ℃ to obtain polyether modified polymer A;
(2) To N 2 60 parts of polyether modified polymer A obtained in the step (1) is added into a protected reaction flask, the mixture is cooled to 60 ℃, 100 parts of deionized water and 40 parts of PVPK35 are added, then sodium hydroxide is added to adjust the pH value of the system to 10, and the mixture is stirred uniformly to obtain the water-soluble dispersing agent.
Example 3
In this embodiment, a water-soluble dispersant is provided, and the preparation method includes the following steps:
(1) To N 2 100 parts by weight of reactive macromer polyether a are weighed into a protected reaction flask 3 Stirring and heating to 140 ℃; uniformly dropwise adding 14 parts of 3-methylstyrene and 40 parts of vinylsulfonic acid monomer b 3 1.5 parts of mixed solution of methyl ethyl ketone peroxide, dropwise adding the mixed solution within 12 hours, and carrying out heat preservation reaction for 2.5 hours at 140 ℃ after the dropwise adding is finished to obtain a polyether modified polymer A;
(2) To N 2 160 parts of the polyether modified polymer A obtained in the step (1) is added into a protected reaction flask, the mixture is cooled to 60 ℃, then 150 parts of deionized water and 50 parts of copovidone VA64 are added, then potassium hydroxide is added to adjust the pH value of the system to 8.0, and the mixture is stirred uniformly to obtain the water-soluble dispersing agent.
Example 4
In this embodiment, a water-soluble dispersant is provided, and the preparation method includes the following steps:
(1) To N 2 80 parts by weight of reactive macromer polyether a are added into a protected reaction flask 1 Stirring and heating to 150 ℃; uniformly dropwise adding 8 parts of 2-methyl styrene and 25 parts of vinylsulfonic acid monomer b 2 Mixed solution of 1.3 parts of methyl ethyl ketone peroxideAnd after the dripping is finished within 11 hours, carrying out heat preservation reaction for 3 hours at 150 ℃ to obtain polyether modified polymer A;
(2) To N 2 110 parts of polyether modified polymer A obtained in the step (1) is added into a protected reaction flask, the mixture is cooled to 60 ℃, 160 parts of deionized water and 60 parts of PVPK35 are added, then potassium hydroxide is added to adjust the pH value of the system to 9, and the mixture is stirred uniformly to obtain the water-soluble dispersing agent.
Example 5
In this embodiment, a water-soluble dispersant is provided, and the preparation method includes the following steps:
(1) To N 2 70 parts of active macromer polyether a which is weighed in parts by weight is added into a protected reaction flask 2 Stirring and heating to 140 ℃; uniformly dropwise adding the vinyl sulfonic acid monomer b containing 12 parts of allyl benzene and 35 parts of vinyl sulfonic acid monomer b 1 1.2 parts of dicumyl peroxide mixed solution, and after the completion of dropwise adding within 10 hours, carrying out heat preservation reaction for 1 hour at 140 ℃ to obtain polyether modified polymer A;
(2) To N 2 110 parts of polyether modified polymer A obtained in the step (1) is added into a protected reaction flask, cooled to 60 ℃, 180 parts of deionized water and 50 parts of PVPK30 are added, then sodium hydroxide is added to adjust the pH value of the system to 7.5, and the water-soluble dispersing agent is obtained after uniform stirring.
Example 6
In this embodiment, a water-soluble dispersant is provided, and the preparation method includes the following steps:
(1) To N 2 50 parts by weight of reactive macromer polyether a are added into a protected reaction flask 3 Stirring and heating to 125 ℃; uniformly dropwise adding the mixture containing 18 parts of styrene and 28 parts of vinylsulfonic acid monomer b 2 0.7 part of mixed solution of di-tert-butyl peroxide, and after the dripping is finished within 8 hours, carrying out heat preservation reaction for 1.5 hours at 125 ℃ to obtain polyether modified polymer A;
(2) To N 2 The polyether modified polymer obtained in the step (1) is added into a protected reaction flask according to the weight partsAnd (3) 90 parts of A, cooling to 60 ℃, then adding 120 parts of deionized water and 40 parts of PVPK25, then adding sodium hydroxide to adjust the pH value of the system to 8.5, and uniformly stirring to obtain the water-soluble dispersing agent.
Example 7
This example differs from example 1 only in that the reactive macromer polyether a in step (1) 1 Is 30 parts by weight.
Example 8
This example differs from example 3 only in that the reactive macromer polyether a in step (1) 1 Is 110 parts by weight.
Comparative example 1
This comparative example differs from example 1 only in that the reactive macromer polyether a of step (1) was used 1 The allyl polyether APEG2000 was replaced with an equal weight fraction.
Comparative example 2
This comparative example differs from example 1 only in that the vinylsulfonic acid-based monomer b of step (1) was used 1 Replaced with an equal weight fraction of vinylsulfonic acid.
Comparative example 3
This comparative example differs from example 1 only in that the vinylbenzene monomer (styrene) of step (1) was replaced with an equal weight part of sodium p-styrenesulfonate.
Comparative example 4
This comparative example differs from example 1 only in that the polyamide-based high molecular polymer B (PVPK 30) of step (2) was replaced with an equal weight fraction of PVPK12.
Comparative example 5
This comparative example differs from example 1 only in that the reactive macromer polyether a of step (1) was used 1 Polyether D-a prepared in comparative preparation example 1 replaced with equal parts by weight 1 。
Comparative example 6
One commercially available dispersant is MF.
Test case
Adding a dispersing agent, water and disperse dye (disperse blue 79 dye) in sequence according to the proportion by adopting a laboratory sanding mode, wherein the total amount of the slurry formula is 200 g; after stirring evenly, 400g of zirconium beads with the particle size of 0.8-1mm are added and sealed in a glass tank, and the mixture is vibrated for 12 hours and filtered to obtain color paste.
The specific formula of the color paste prepared by the invention is shown in table 1:
TABLE 1
Performance testing
(1) Viscosity: the measurement was performed using an NDJ-1B rotational viscometer, shanghai Changji geological instruments Co., ltd; wherein "-" indicates that the viscosity is too great to measure;
(2) Particle size: testing with BT-90 laser particle sizer, available from Dandong Baite instruments; wherein "\" represents precipitation or no fluidity, and cannot be tested;
(3) Storage stability: storing at 55deg.C for 7 days, observing color paste state, and retesting particle diameter and viscosity;
(4) Centrifugal precipitation rate (%): centrifuging the dye color paste for 20 minutes at 4000 rpm, washing with absolute ethyl alcohol, and baking at 90 ℃ to constant weight, and precisely weighing the precipitate weight; precipitation rate = precipitation weight ≡ (color paste dye content x sample size) ×100%; wherein "+" indicates no flowability and no testing.
The specific test results are shown in table 2:
TABLE 2
As can be seen from Table 2, the water-soluble dispersing agent prepared by compounding the polyether modified polymer A and the polyamide high-molecular polymer B has good dispersing effect (particle size D50 (initial): 189-234 nm) on dye color paste on the premise of small dosage, the viscosity of the color paste can meet the requirement (viscosity (initial): 98-125 mpa.s), the centrifugal precipitation rate is low (0.6% -2.3%), the color paste stability is good (the viscosity and the particle size of the color paste are not greatly changed when the color paste is stored at 55 ℃ for 7 days), and the storage period is long, thereby being superior to the commercially available dispersing agent.
As is clear from the comparison between the test examples 7 and 1, if the addition amount of the reactive macromonomer polyether is too small, the viscosity, the particle size and the centrifugal precipitation rate of the dye paste are greatly increased, and the stability is poor; as is clear from the comparison between test example 8 and test example 3, too much addition of the reactive macromer polyether leads to a significant increase in the viscosity, particle size and centrifugal precipitation rate of the dye paste.
As is clear from the comparison of the comparative test examples 1 to 5 with the test example 1, if any one of the preparation raw materials (vinylbenzene monomer, vinylsulfonic acid monomer and active macromonomer polyether) of the polyether modified polymer A is replaced with other components, or the polyamide high-molecular polymer B is replaced with other components, the viscosity, the particle size and the centrifugal precipitation rate of the dye color paste are obviously increased.
The applicant states that the water-soluble dispersants of the present invention, and their methods of preparation and use are described by way of the above examples, but the invention is not limited to, i.e. it is not meant that the invention must be practiced in dependence upon the above examples. It should be apparent to those skilled in the art that any modification of the present invention, equivalent substitution of raw materials for the product of the present invention, addition of auxiliary components, selection of specific modes, etc., falls within the scope of the present invention and the scope of disclosure.
Claims (10)
1. A water-soluble dispersing agent, which is characterized by comprising a polyether modified polymer A and a polyamide high-molecular polymer B;
the preparation raw materials of the polyether modified polymer A comprise vinyl benzene monomers, vinyl sulfonic acid monomers and active macromonomer polyether;
the polyamide high molecular polymer B comprises a homopolymer of vinyl pyrrolidone and/or a copolymer of vinyl pyrrolidone.
2. The water-soluble dispersant of claim 1 wherein said reactive macromer polyether is prepared by the following preparation method:
adding polyetheramine and allyl succinic anhydride into a reactor, heating, preserving heat until no water is distilled out in the reaction process, and obtaining the active macromonomer polyether;
preferably, the polyether amine is mono-primary amino polyether which is obtained by taking monoalcohol as an initiator to initiate ethylene oxide self-polymerization or initiate copolymerization of ethylene oxide and propylene oxide, and the terminal hydroxyl group is converted into amine;
preferably, the polyetheramine has a weight average molecular weight of 500 to 2500g/mol;
preferably, the polyetheramine comprises any one or a combination of at least two of JEFFAMINE M-2070, JEFFAMINE M-1000 or JEFFAMINE M-600;
preferably, the molar ratio of polyetheramine to allylsuccinic anhydride is (0.5-1.5): 1, preferably 1:1;
preferably, the temperature is raised to 120-160 ℃;
preferably, the time of heat preservation is 2-6 hours;
preferably, the preparation of the reactive macromer polyether is carried out under inert gas protection.
3. The water-soluble dispersant of claim 1 or 2 wherein the reactive macromer polyether has the structure of formula I:
wherein R is 1 Is hydrogen or methyl, R 2 Methyl, ethyl, propyl or butyl, m is 1An integer of 0 to 60, and n is an integer of 0 to 15.
4. A water-soluble dispersant according to any one of claims 1 to 3, wherein the vinylsulfonic acid-based monomer is prepared by the following preparation method:
adding hydroxylated acrylic monomers and alkyl sultone into a reactor, mixing and reacting until the residual quantity of the alkyl sultone is less than 0.5%, and obtaining the vinyl sulfonic monomers;
preferably, the hydroxylated acrylic monomer comprises any one or a combination of at least two of hydroxyethyl acrylate, hydroxyethyl methacrylate, hydroxypropyl acrylate, hydroxypropyl methacrylate, hydroxybutyl acrylate, hydroxybutyl methacrylate, hydroxypentyl acrylate or hydroxypentyl methacrylate;
preferably, the alkyl sultone comprises any one or a combination of at least two of 1, 3-propane sultone, 1-methyl-1, 3-propane sultone, 2-methyl-1, 3-propane sultone, 3-methyl-1, 3-propane sultone, 1, 4-butane sultone, 1-methyl-1, 4-butane sultone, 2-methyl-1, 4-butane sultone, 3-methyl-1, 4-butane sultone or 4-methyl-1, 4-butane sultone;
preferably, the molar ratio of hydroxylated acrylic monomer to alkyl sultone is 1:1.
5. The water-soluble dispersant according to claim 4, wherein the reaction system further comprises an acid catalyst;
preferably, the acid catalyst comprises any one or a combination of at least two of p-toluenesulfonic acid, sulfuric acid, propionic acid or hydrochloric acid;
preferably, the addition amount of the acid catalyst is 0.5-3% of the sum of the weight parts of the hydroxylated acrylic monomer and the weight parts of the alkyl sultone;
preferably, the temperature of the mixing is 60-90 ℃;
preferably, the reaction time is 5 to 20 hours;
preferably, the preparation process of the vinylsulfonic acid monomer is carried out under the protection of inert gas.
6. The water-soluble dispersant of any one of claims 1 to 5, wherein the vinylbenzene monomer comprises any one or a combination of at least two of styrene, β -methylstyrene, allylbenzene, 3-methylstyrene, 2-methylstyrene, or 2-isopropenyltoluene;
preferably, the mass ratio of the vinylbenzene monomer to the vinylsulfonic acid monomer to the active macromonomer polyether is (3-10): (10-20): (20-50);
preferably, the polyether modified polymer A is prepared from a raw material further comprising an initiator.
7. The water-soluble dispersant according to any one of claims 1 to 6, wherein the polyether modified polymer a has a weight average molecular weight of 50000 to 200000g/mol, preferably 50000 to 100000g/mol;
preferably, the weight average molecular weight of the polyamide-based high molecular polymer B is 2000-100000 g/mol, preferably 10000-50000 g/mol;
preferably, the polyamide-based high molecular polymer B comprises any one or a combination of at least two of PVPK25, PVPK30, PVPK35 and copovidone VA 64;
preferably, the mass ratio of the polyether modified polymer A to the polyamide high molecular polymer B is (60-160): 40-70;
preferably, the water-soluble dispersing agent also comprises deionized water and a pH regulator;
preferably, the water-soluble dispersing agent comprises the following raw materials in parts by weight:
8. a method of preparing the water-soluble dispersant as claimed in any one of claims 1 to 7, wherein the method comprises the steps of:
(1) Adding reactive macromonomer polyether with formula amount into a reactor, heating, then adding vinyl benzene monomer, vinyl sulfonic acid monomer and optional initiator, and carrying out heat preservation reaction to obtain polyether modified polymer A;
(2) And (3) cooling the polyether modified polymer A obtained in the step (1), then adding optional deionized water and polyamide high molecular polymer B, then adding optional pH regulator, and stirring to obtain the water-soluble dispersing agent.
9. The method according to claim 8, wherein the temperature rise in step (1) is to 100 to 150 ℃;
preferably, the temperature of the heat preservation reaction in the step (1) is 100-150 ℃, and the time of the heat preservation reaction is 1-3 hours;
preferably, both step (1) and step (2) are carried out under the protection of inert gas;
preferably, the cooling in the step (2) is to cool to 50-60 ℃.
10. Use of a water-soluble dispersant as claimed in any one of claims 1 to 7 in dye dispersion.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202310527883.0A CN116515052B (en) | 2023-05-11 | 2023-05-11 | Water-soluble dispersing agent and preparation method and application thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202310527883.0A CN116515052B (en) | 2023-05-11 | 2023-05-11 | Water-soluble dispersing agent and preparation method and application thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN116515052A true CN116515052A (en) | 2023-08-01 |
| CN116515052B CN116515052B (en) | 2024-05-17 |
Family
ID=87393919
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202310527883.0A Active CN116515052B (en) | 2023-05-11 | 2023-05-11 | Water-soluble dispersing agent and preparation method and application thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN116515052B (en) |
Citations (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1242399A (en) * | 1998-07-22 | 2000-01-26 | 纳幕尔杜邦公司 | Aqueous pigmented ink jet inks for printing on vinyl type substrate |
| CN107652405A (en) * | 2017-10-10 | 2018-02-02 | 江苏苏博特新材料股份有限公司 | A kind of polycarboxylate water-reducer of acid amides/imide structure and preparation method thereof |
| JP2018177995A (en) * | 2017-04-14 | 2018-11-15 | 信越化学工業株式会社 | Adhesive composition and film formed by using the composition |
| CN110818845A (en) * | 2019-11-26 | 2020-02-21 | 上海宇昂水性新材料科技股份有限公司 | Preparation method of aqueous wetting dispersant, aqueous wetting dispersant and application |
| CN111087852A (en) * | 2019-12-20 | 2020-05-01 | 南通纺织丝绸产业技术研究院 | Ink-jet printing ink containing disperse dye and reactive dye and application thereof |
| CN112920414A (en) * | 2021-04-19 | 2021-06-08 | 传美讯电子科技（珠海）有限公司 | Comb-shaped dispersing agent, preparation method and application thereof, and water-based ink-jet color paste |
| CN113512201A (en) * | 2021-04-26 | 2021-10-19 | 传美讯电子科技（珠海）有限公司 | Comb-shaped dispersing agent, preparation method and application thereof, and weak solvent ink-jet color paste |
| CN114525044A (en) * | 2021-12-28 | 2022-05-24 | 浙江龙盛染料化工有限公司 | Sol type liquid disperse dye, preparation and application thereof |
| CN116023600A (en) * | 2022-12-30 | 2023-04-28 | 上海宇昂水性新材料科技股份有限公司 | Hyper-dispersant, and preparation method and application thereof |
-
2023
- 2023-05-11 CN CN202310527883.0A patent/CN116515052B/en active Active
Patent Citations (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1242399A (en) * | 1998-07-22 | 2000-01-26 | 纳幕尔杜邦公司 | Aqueous pigmented ink jet inks for printing on vinyl type substrate |
| JP2018177995A (en) * | 2017-04-14 | 2018-11-15 | 信越化学工業株式会社 | Adhesive composition and film formed by using the composition |
| CN107652405A (en) * | 2017-10-10 | 2018-02-02 | 江苏苏博特新材料股份有限公司 | A kind of polycarboxylate water-reducer of acid amides/imide structure and preparation method thereof |
| CN110818845A (en) * | 2019-11-26 | 2020-02-21 | 上海宇昂水性新材料科技股份有限公司 | Preparation method of aqueous wetting dispersant, aqueous wetting dispersant and application |
| CN111087852A (en) * | 2019-12-20 | 2020-05-01 | 南通纺织丝绸产业技术研究院 | Ink-jet printing ink containing disperse dye and reactive dye and application thereof |
| CN112920414A (en) * | 2021-04-19 | 2021-06-08 | 传美讯电子科技（珠海）有限公司 | Comb-shaped dispersing agent, preparation method and application thereof, and water-based ink-jet color paste |
| CN113512201A (en) * | 2021-04-26 | 2021-10-19 | 传美讯电子科技（珠海）有限公司 | Comb-shaped dispersing agent, preparation method and application thereof, and weak solvent ink-jet color paste |
| CN114525044A (en) * | 2021-12-28 | 2022-05-24 | 浙江龙盛染料化工有限公司 | Sol type liquid disperse dye, preparation and application thereof |
| CN116023600A (en) * | 2022-12-30 | 2023-04-28 | 上海宇昂水性新材料科技股份有限公司 | Hyper-dispersant, and preparation method and application thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| CN116515052B (en) | 2024-05-17 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP6074517B2 (en) | Method for producing slump retention type polycarboxylate-based high performance fluidizing agent | |
| KR101567106B1 (en) | Non-ionic water-soluble additives based on allyl ether and vinyl ether | |
| CN102993430B (en) | Intermediate of high strength water reducer, preparation method thereof and high strength water reducer prepared by intermediate | |
| CN110845672A (en) | Polycarboxylic acid series concrete gel reducing agent and preparation method thereof | |
| CN108699201A (en) | ABA block polymer, dispersant and pigment dispensing composition | |
| CN1935733A (en) | Low molecular weight copolymer dispersant and its preparing method | |
| EP3571236B1 (en) | Polymeric dispersant, dispersion therewith and printing method | |
| KR20130026426A (en) | Mixtures of fibre-reactive dyes and their use in a method for di- or trichromatic dyeing or printing | |
| CN115772347A (en) | High-molecular dispersing agent and preparation method and application thereof | |
| CN116515052B (en) | Water-soluble dispersing agent and preparation method and application thereof | |
| CN113896845A (en) | Low-sensitivity slow-release polycarboxylic slump retaining agent and preparation method thereof | |
| CN101602834B (en) | Preparation method of polycarboxylic acid concrete dispersers | |
| CN116478335A (en) | Preparation method of chlorinated polypropylene ternary graft | |
| CN111348858B (en) | Early-strength polycarboxylate superplasticizer and preparation method thereof | |
| CN116515054B (en) | Water-soluble dispersing agent and preparation method and application thereof | |
| CN116023600A (en) | Hyper-dispersant, and preparation method and application thereof | |
| CN109956697B (en) | Multi-adsorption-group intermediate, preparation method and application of polymer thereof | |
| CN110982003B (en) | Preparation method of star polymer dispersant, product and application thereof | |
| CN116535584B (en) | Polymer dispersing agent and preparation method and application thereof | |
| CN112608428A (en) | Water-reducing cement grinding aid and preparation method and application thereof | |
| CN111285953A (en) | Acrylic emulsion and preparation method thereof | |
| CN116515055B (en) | Water-soluble polymer dispersing agent and preparation method and application thereof | |
| CN114716685B (en) | Polycarboxylic acid dispersant, preparation method thereof, polycarboxylic acid dispersant and application | |
| CN116333231B (en) | Ultra-high dispersion type water reducer and preparation method thereof | |
| CN116515053B (en) | Water-soluble polymer dispersing agent and preparation method and application thereof |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |