CN116589654A - Comb-type water-based polyurethane dispersing agent for disperse dye and preparation method thereof - Google Patents
Comb-type water-based polyurethane dispersing agent for disperse dye and preparation method thereof Download PDFInfo
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- CN116589654A CN116589654A CN202310551211.3A CN202310551211A CN116589654A CN 116589654 A CN116589654 A CN 116589654A CN 202310551211 A CN202310551211 A CN 202310551211A CN 116589654 A CN116589654 A CN 116589654A
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- 239000002270 dispersing agent Substances 0.000 title claims abstract description 47
- 239000004814 polyurethane Substances 0.000 title claims abstract description 40
- 229920002635 polyurethane Polymers 0.000 title claims abstract description 40
- 239000000986 disperse dye Substances 0.000 title claims abstract description 22
- 238000002360 preparation method Methods 0.000 title claims abstract description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 title claims description 36
- QWXYZCJEXYQNEI-OSZHWHEXSA-N intermediate I Chemical compound COC(=O)[C@@]1(C=O)[C@H]2CC=[N+](C\C2=C\C)CCc2c1[nH]c1ccccc21 QWXYZCJEXYQNEI-OSZHWHEXSA-N 0.000 claims abstract description 14
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims abstract description 12
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims abstract description 12
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000002202 Polyethylene glycol Substances 0.000 claims abstract description 10
- 239000004721 Polyphenylene oxide Substances 0.000 claims abstract description 10
- 229920000570 polyether Polymers 0.000 claims abstract description 10
- 229920001223 polyethylene glycol Polymers 0.000 claims abstract description 10
- YFMUPHJGWWRKLX-UHFFFAOYSA-N boric acid;propane-1,2-diol Chemical compound OB(O)O.CC(O)CO YFMUPHJGWWRKLX-UHFFFAOYSA-N 0.000 claims abstract description 9
- 229960004063 propylene glycol Drugs 0.000 claims abstract description 9
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000005058 Isophorone diisocyanate Substances 0.000 claims abstract description 7
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 claims abstract description 7
- 239000004327 boric acid Substances 0.000 claims abstract description 7
- 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 abstract description 7
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims abstract description 6
- 238000006243 chemical reaction Methods 0.000 claims description 64
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 30
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 30
- 238000010992 reflux Methods 0.000 claims description 30
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 20
- 230000001105 regulatory effect Effects 0.000 claims description 17
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 15
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 15
- 239000008367 deionised water Substances 0.000 claims description 13
- 229910021641 deionized water Inorganic materials 0.000 claims description 13
- 238000003756 stirring Methods 0.000 claims description 13
- 238000009833 condensation Methods 0.000 claims description 12
- 230000005494 condensation Effects 0.000 claims description 12
- 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 12
- 238000001816 cooling Methods 0.000 claims description 10
- 238000010438 heat treatment Methods 0.000 claims description 10
- PTBDIHRZYDMNKB-UHFFFAOYSA-N 2,2-Bis(hydroxymethyl)propionic acid Chemical compound OCC(C)(CO)C(O)=O PTBDIHRZYDMNKB-UHFFFAOYSA-N 0.000 claims description 7
- 238000004821 distillation Methods 0.000 claims description 7
- 238000001914 filtration Methods 0.000 claims description 6
- WHIVNJATOVLWBW-UHFFFAOYSA-N n-butan-2-ylidenehydroxylamine Chemical compound CCC(C)=NO WHIVNJATOVLWBW-UHFFFAOYSA-N 0.000 claims description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical class [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 5
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 claims description 5
- 239000012975 dibutyltin dilaurate Substances 0.000 claims description 5
- 239000000706 filtrate Substances 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- 229920001451 polypropylene glycol Polymers 0.000 claims description 5
- 239000012295 chemical reaction liquid Substances 0.000 claims description 4
- 238000004321 preservation Methods 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 2
- 239000000975 dye Substances 0.000 abstract description 14
- 239000002245 particle Substances 0.000 abstract description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract description 8
- -1 polyoxyethylene side chains Polymers 0.000 abstract description 7
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 abstract description 6
- 235000013772 propylene glycol Nutrition 0.000 abstract description 6
- 238000004873 anchoring Methods 0.000 abstract description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract description 4
- 238000001179 sorption measurement Methods 0.000 abstract description 4
- 230000002194 synthesizing effect Effects 0.000 abstract description 4
- 239000007791 liquid phase Substances 0.000 abstract description 3
- 230000000694 effects Effects 0.000 abstract description 2
- 239000002994 raw material Substances 0.000 abstract 2
- 238000004945 emulsification Methods 0.000 abstract 1
- 230000001376 precipitating effect Effects 0.000 abstract 1
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 12
- 239000006185 dispersion Substances 0.000 description 8
- 238000010521 absorption reaction Methods 0.000 description 6
- 238000002329 infrared spectrum Methods 0.000 description 6
- 238000000227 grinding Methods 0.000 description 5
- 238000002835 absorbance Methods 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 150000008064 anhydrides Chemical class 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 238000005452 bending Methods 0.000 description 3
- 238000005119 centrifugation Methods 0.000 description 3
- 230000001276 controlling effect Effects 0.000 description 3
- 238000009413 insulation Methods 0.000 description 3
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000007614 solvation Methods 0.000 description 3
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- YDEXUEFDPVHGHE-GGMCWBHBSA-L disodium;(2r)-3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfonatopropyl)phenoxy]propane-1-sulfonate Chemical compound [Na+].[Na+].COC1=CC=CC(C[C@H](CS([O-])(=O)=O)OC=2C(=CC(CCCS([O-])(=O)=O)=CC=2)OC)=C1O YDEXUEFDPVHGHE-GGMCWBHBSA-L 0.000 description 2
- NVVZQXQBYZPMLJ-UHFFFAOYSA-N formaldehyde;naphthalene-1-sulfonic acid Chemical compound O=C.C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 NVVZQXQBYZPMLJ-UHFFFAOYSA-N 0.000 description 2
- SLGWESQGEUXWJQ-UHFFFAOYSA-N formaldehyde;phenol Chemical compound O=C.OC1=CC=CC=C1 SLGWESQGEUXWJQ-UHFFFAOYSA-N 0.000 description 2
- 229920001568 phenolic resin Polymers 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 2
- 239000006228 supernatant Substances 0.000 description 2
- AIARLPIXVMHZLJ-UHFFFAOYSA-N 4,8-diamino-2-bromo-1,5-dihydroxyanthracene-9,10-dione Chemical compound O=C1C2=C(N)C=C(Br)C(O)=C2C(=O)C2=C1C(O)=CC=C2N AIARLPIXVMHZLJ-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 229920001730 Moisture cure polyurethane Polymers 0.000 description 1
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000003795 desorption Methods 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 238000005189 flocculation Methods 0.000 description 1
- 230000016615 flocculation Effects 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 239000012038 nucleophile Substances 0.000 description 1
- 125000003544 oxime group Chemical group 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000013112 stability test Methods 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 239000004753 textile Substances 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
- 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
- C08G18/08—Processes
- C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
- C08G18/12—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step using two or more compounds having active hydrogen in the first polymerisation step
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/2805—Compounds having only one group containing active hydrogen
- C08G18/2815—Monohydroxy compounds
- C08G18/283—Compounds containing ether groups, e.g. oxyalkylated monohydroxy compounds
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/48—Polyethers
- C08G18/4825—Polyethers containing two hydroxy groups
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- 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
- C08G18/6692—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/34
-
- 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
- D06P1/5264—Macromolecular compounds obtained otherwise than by reactions involving only unsaturated carbon-to-carbon bonds
- D06P1/5285—Polyurethanes; Polyurea; Polyguanides
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Dispersion Chemistry (AREA)
- Polyurethanes Or Polyureas (AREA)
Abstract
The invention discloses a comb-type waterborne polyurethane dispersing agent for disperse dye and a preparation method thereof. Synthesizing an intermediate I by taking polyethylene glycol monomethyl ether and trimellitic anhydride as raw materials, synthesizing 1, 2-propanediol borate by taking boric acid and 1, 2-propanediol as raw materials, and synthesizing an intermediate II; and then, reacting isophorone diisocyanate, polyether glycol and an intermediate II, and carrying out chain extension, end capping and high-speed emulsification to obtain the comb-type waterborne polyurethane dispersing agent, wherein the block structure of the comb-type waterborne polyurethane dispersing agent contains phenyl and polyoxyethylene side chains, the phenyl is used as an anchoring group to provide an adsorption site for the dispersing agent to adsorb disperse dye, and the dispersing agent carries out multipoint anchoring through intermolecular acting force and pi-pi stacking effect. The polyoxyethylene side chains act as solvated chains and extend in the liquid phase to form solvated layers providing steric hindrance. Meanwhile, carboxyl groups on polyurethane molecular chains are ionized, an electric double layer is formed on the surfaces of the dye particles, and the electric double layer and steric hindrance cooperate to prevent the dye particles from agglomerating and precipitating.
Description
Technical Field
The invention relates to the technical field of textile printing and dyeing auxiliary synthesis, in particular to a comb-type water-based polyurethane dispersing agent for disperse dye and a preparation method thereof.
Background
The disperse dye has small molecules and is in a nonionic state with extremely low solubility in water, and in order to ensure that the dye is better dispersed in the water, dye particles must be ground to a certain fineness (generally below 2 μm) and a uniform and stable suspension is formed by the action of a dispersing agent. The small molecular dispersant cannot generate enough adsorption sites and solvated chains with enough length, and is only dependent on an electrostatic stabilization mechanism and smaller steric hindrance, so that the adsorption force on the particle surface is weaker, and desorption is easy. The polymer dispersant has higher molecular weight and more anchoring sites, can form a solvated chain with enough length, further provides steric hindrance and has higher adsorption efficiency. The polymeric dispersants commonly used for dye dispersion are mostly sodium lignin sulfonate, naphthalene sulfonic acid formaldehyde condensate and phenol formaldehyde condensate sulfonate. These dispersants also have problems such as poor water solubility of sodium lignin sulfonate and staining of some fibers; naphthalene sulfonic acid formaldehyde condensate and phenol formaldehyde condensate sulfonate contain free formaldehyde and are reducing to partial dye.
Disclosure of Invention
Aiming at the defects of the prior art, the invention provides a comb-type waterborne polyurethane dispersing agent capable of effectively dispersing disperse dye and improving storage stability and a preparation method thereof.
The technical scheme of the invention also provides a preparation method for the comb-type water-based polyurethane dispersing agent, which comprises the following steps:
(1) Adding 40-60 parts of polyethylene glycol monomethyl ether, 14-17 parts of trimellitic anhydride and 40-60 parts of ethyl acetate into a reaction vessel with a stirrer and a condensation reflux device, starting the condensation reflux device and the stirrer, reacting for 3-4 hours at the temperature of 80-90 ℃, regulating the temperature to 50-60 ℃ and the pressure to minus 0.08-minus 0.1MPa, and removing and recycling the ethyl acetate by reduced pressure distillation to obtain an intermediate I;
(2) Adding 3-5 parts of boric acid and 10-16 parts of 1, 2-propylene glycol into a reaction vessel with a stirrer, and reacting for 2-3 hours at the temperature of 120-130 ℃ under the stirring condition to obtain 1, 2-propylene glycol borate; adding 11-13 parts of 1, 2-propylene glycol borate, 40-60 parts of intermediate I and 0.5-0.75 part of p-toluenesulfonic acid into a reaction vessel with a stirrer, and reacting for 2-3 h under the stirring condition at the temperature of 130-140 ℃; cooling the reaction liquid to below 90 ℃, adding 6080 parts of deionized water, adding a condensing reflux device, starting condensing reflux, adjusting the temperature to 95-100 ℃, reacting for 2 hours under the condition of keeping the temperature, cooling to 20-30 ℃, and adding 80-110 parts of saturated sodium carbonate solution; regulating the temperature to 60-70 ℃ and the pressure to minus 0.08-minus 0.1MPa, distilling under reduced pressure to remove water, dissolving with absolute methanol, filtering, heating the filtrate to 30-40 ℃, distilling under reduced pressure to remove recovered methanol under the condition that the pressure is minus 0.08-minus 0.1MPa, and obtaining an intermediate II;
(3) Adding 40-60 parts of intermediate II, 40-60 parts of acetone, 18 parts of polyether glycol and 0.06-0.12 part of dibutyltin dilaurate into a reaction vessel with a stirrer, a condensing reflux device and a dropping funnel; starting a condensing reflux device and a stirrer, heating to 70-80 ℃, gradually adding 32 parts of isophorone diisocyanate, and reacting for 2-3 hours under the condition of keeping the temperature at 70-80 ℃ after finishing dropwise addition within 50-80 min; 4-7 parts of 2, 2-dimethylolpropionic acid is completely dissolved in 5-8 parts of N, N-dimethylformamide, then added into a reaction vessel, the temperature is regulated to 80-90 ℃ to react for 1.5-2 hours under the condition of keeping the temperature, and then 5-9 parts of methyl ethyl ketoxime are added into the reaction vessel to continuously react for 1-1.5 hours under the condition of keeping the temperature; after the reaction liquid is cooled to 40-50 ℃, 3-5 parts of triethylamine is added into a reaction container, the reaction is carried out for 0.5-1 h under the temperature condition of 40-50 ℃, the pressure is regulated to be minus 0.08-minus 0.1Mpa, after the recovered acetone is removed by reduced pressure distillation, 250-290 parts of deionized water is added, and the mixture is stirred for 0.5-1 h at a high speed at the rotating speed of 1500-3000 r/min, thus obtaining the comb-type water-based polyurethane dispersing agent.
In the technical scheme, the number average molecular weight of the polyethylene glycol monomethyl ether in the step (1) is 500, 550, 600, 650, 700 and 750; the polyether glycol used in the step (3) is polypropylene glycol, and the number average molecular weight is 1000.
The technical scheme of the invention also comprises a comb-type water-based polyurethane dispersing agent for disperse dye, which is obtained by the preparation method.
The synthetic reaction route for preparing the comb-type water-based polyurethane dispersing agent for the disperse dye is as follows:
(1) Synthesis of intermediate I
(2) Synthesis of intermediate II
(3) Synthesis of comb-type water-based polyurethane dispersing agent
R 1 The method comprises the following steps:
wherein k=17; n is more than or equal to 12 and less than or equal to 17; a is more than or equal to 8 and less than or equal to 14.
The principle of the invention is as follows: the carbon on the anhydride in the trimellitic anhydride has stronger positive electricity tendency, is more easily attacked by nucleophile, and the anhydride in the structure is more easily reacted with polyethylene glycol monomethyl ether compared with carboxyl. According to the difference of the reactivity of anhydride and carboxyl in trimellitic anhydride to hydroxyl, the intermediate I is synthesized through monoesterification by controlling the feeding ratio. Boric acid reacts with primary hydroxyl groups on 1, 2-propylene glycol molecules to generate 1, 2-propylene glycol boric acid ester, the 1, 2-propylene glycol boric acid ester reacts with the intermediate I under the catalysis of p-toluenesulfonic acid to perform esterification reaction, and the intermediate II is obtained through hydrolysis. The isocyanate group, the hydroxyl and the oxime group have higher reactivity; firstly, synthesizing polyurethane prepolymer with terminal isocyanate groups by controlling the ratio of polyether glycol, isophorone diisocyanate and the amount of intermediate II substances and the feeding sequence; then, the isocyanate groups in the prepolymer react with the hydroxyl groups of the 2, 2-dimethylolpropionic acid to carry out chain extension; and finally, blocking isocyanate at the tail end of the molecule by using methyl ethyl ketone oxime, and emulsifying to obtain the comb-type waterborne polyurethane dispersing agent. According to the invention, phenyl and polyoxyethylene chains are introduced into the block structure of polyurethane, and the dispersing agent is anchored at multiple points by virtue of intermolecular acting force and pi-pi stacking effect provided by the phenyl, so that the dispersing agent is firmly adsorbed on the surface of disperse dye particles; the polyoxyethylene chains extend in the liquid phase to form a solvation layer, creating steric hindrance preventing aggregation between the dye particles. The chain extension is carried out by using 2, 2-dimethylolpropionic acid, so that the water solubility of polyurethane can be enhanced, an electric double layer can be formed by ionization in water, and the metastable state among particles in a dispersion system is maintained by electrostatic repulsive force.
The comb-type waterborne polyurethane dispersing agent for disperse dyes has higher dispersing efficiency due to the comb-type structure; the polyurethane has multiple anchoring sites, is easy to modify and change the structure of a polymer chain through a long molecular chain and a solvation chain segment, and can form effective steric hindrance to prevent flocculation precipitation among particles.
Due to the application of the technical scheme, compared with the prior art, the invention has the following advantages:
1. the phenyl in the block structure of the comb-type waterborne polyurethane dispersing agent can be anchored at multiple points on the surface of disperse dye particles and fixed on the dye particles; the polyurethane dispersant has higher molecular weight and has stronger intermolecular force with dye particles; polyoxyethylene side chains provide solvation and steric hindrance that prevent reagglomeration of the dispersed particles; carboxyl groups in polyurethane molecular chains are ionized in a liquid phase to provide effective electrostatic acting force, and the metastable state of a dispersion system is realized according to the synergistic effect of electrostatic repulsion among particles and steric hindrance of solvated chains, so that the polyurethane molecular chains are good in stability and favorable for storage.
2. The comb-type water-based polyurethane dispersing agent can regulate and control the grafting density of a comb-type structure by controlling the feeding ratio of the intermediate and polyether polyol, and can obtain polyurethane dispersing agents with different side chain lengths by using polyethylene glycol monomethyl ether with different molecular weights.
Drawings
FIG. 1 is an infrared spectrum of a comb-type aqueous polyurethane dispersant provided in example 1 of the present invention;
FIG. 2 is an infrared spectrum of the comb-type aqueous polyurethane dispersant provided in example 2 of the present invention;
fig. 3 is an infrared spectrum of the comb-type aqueous polyurethane dispersant provided in example 3 of the present invention.
Detailed Description
The technical scheme of the invention is further described below with reference to the accompanying drawings and the specific embodiments.
Example 1
(1) Adding 20g of polyethylene glycol monomethyl ether 500, 7.69g of trimellitic anhydride and 20g of ethyl acetate into a reaction vessel with a stirrer and a condensation reflux device, starting the condensation reflux device and the stirrer, reacting for 4 hours at 80 ℃, adjusting the temperature to 50 ℃ and the pressure to minus 0.1MPa, and distilling under reduced pressure to remove and recycle the ethyl acetate to obtain an intermediate I.
(2) Adding 2.1g of boric acid and 7.61g of 1, 2-propanediol into a reaction vessel with a stirrer, starting stirring, and reacting at 120 ℃ for 3 hours to obtain 1, 2-propanediol borate; 5.54g of 1, 2-propanediol borate, 20g of intermediate I and 0.26g of p-toluenesulfonic acid are added into a reaction vessel with a stirrer, stirring is started, and the reaction is carried out for 3 hours at 130 ℃; cooling the reaction solution to below 90 ℃, adding 30g of deionized water, adding a condensing reflux device, starting condensing reflux, adjusting the temperature to 95 ℃, carrying out heat preservation reaction for 2 hours at the temperature, cooling to 25 ℃, and adding 41g of saturated sodium carbonate solution; regulating the temperature to 60 ℃ and the pressure to minus 0.1MPa, distilling under reduced pressure to remove water, dissolving with anhydrous methanol, filtering, heating the filtrate to 50 ℃, and distilling under reduced pressure to remove recovered methanol under the condition that the pressure is minus 0.1MPa to obtain an intermediate II.
(3) 21.82g of intermediate II, 20g of acetone, 9g of polypropylene glycol 1000 and 0.06g of dibutyltin dilaurate were charged into a reaction vessel equipped with a stirrer, a condensing reflux device and a dropping funnel; starting a condensing reflux device and a stirrer, heating to 70 ℃, gradually adding 16g of isophorone diisocyanate, dropwise adding within 60min, and reacting for 3h at the temperature; 3.22g of 2, 2-dimethylolpropionic acid is completely dissolved in 3.5g of N, N-dimethylformamide, then is added into a reaction vessel, the temperature is regulated to 80 ℃, the reaction is carried out for 2 hours at the temperature, and then 2.51g of methyl ethyl ketoxime is added into the reaction vessel for continuous thermal insulation reaction for 1.5 hours; after the reaction solution was cooled to 40 ℃, 2.43g of triethylamine was added into the reaction vessel, the reaction was carried out at 40 ℃ for 30 minutes while maintaining the temperature, the temperature was adjusted to 45 ℃ and the pressure was-0.1 Mpa, distillation was carried out under reduced pressure, after the recovered acetone was removed, 128.31g of deionized water was added, and stirring was carried out at a high speed at 1500r/min for 60 minutes, to obtain a comb-type aqueous polyurethane dispersant.
Referring to fig. 1, an infrared spectrum of the comb-type aqueous polyurethane dispersant in this example is shown. At 3359cm -1 、1554cm -1 Is characterized by a stretching vibration and deformation vibration peak of N-H in carbamate, 1714cm -1 The stretching vibration peak of C=O in the carbamate is shown, and the three peaks are characteristic absorption peaks of the carbamate. The asymmetric stretching vibration peak of C=N in carbamate is 1243cm -1 Where it is located. 2949cm -1 、2873cm -1 Where is-CH 3 and-CH 2 C-H stretching vibration peak of 1661cm -1 A stretching vibration peak of C=N, 1456cm -1 The position is a stretching vibration peak of C=C in benzene ring, 1361cm -1 The left and right are C-H ring skeletons in the aromatic ring to vibrate. The peak of the stretching vibration and bending vibration of C-O-C in the polyether chain is 1094cm -1 Broad peak, 947cm -1 、846cm -1 Where it is located. 2300-2250 cm -1 No characteristic absorption peak of the-NCO was found, indicating that the-NCO had reacted completely. The target product is synthesized.
Example 2
(1) 23g of polyethylene glycol monomethyl ether 550, 8.03g of trimellitic anhydride and 30g of ethyl acetate are added into a reaction vessel with a stirrer and a condensation reflux device, the condensation reflux device and the stirrer are started, the temperature is regulated to 55 ℃ and the pressure is regulated to minus 0.09MPa after the reaction is carried out for 3 hours at 90 ℃, and the ethyl acetate is distilled off under reduced pressure to obtain an intermediate I.
(2) 1.75g of boric acid and 6.09g of 1, 2-propanediol were added into a reaction vessel equipped with a stirrer, stirring was started, and after 2.5 hours of reaction at 125 ℃,1, 2-propanediol borate was obtained; 6.3g of 1, 2-propanediol borate, 25g of intermediate I and 0.31g of p-toluenesulfonic acid are added into a reaction vessel with a stirrer, stirring is started, and the reaction is carried out for 2 hours at 140 ℃; cooling the reaction solution to below 90 ℃, adding 35g of deionized water, adding a condensing reflux device, starting condensing reflux, adjusting the temperature to 100 ℃, carrying out heat preservation reaction for 2 hours at the temperature, cooling to 20 ℃, and adding 47g of saturated sodium carbonate solution; adjusting the temperature to 65 ℃ and the pressure to minus 0.09MPa, distilling under reduced pressure to remove water, dissolving with absolute methanol, filtering, heating the filtrate to 55 ℃, and distilling under reduced pressure to remove recovered methanol under the condition that the pressure is minus 0.09MPa to obtain an intermediate II.
(3) 23.16g of intermediate II, 25g of acetone, 9g of polypropylene glycol 1000 and 0.08g of dibutyltin dilaurate were charged into a reaction vessel equipped with a stirrer, a condensation reflux apparatus and a dropping funnel; starting a condensing reflux device and a stirrer, heating to 75 ℃, gradually adding 16g of isophorone diisocyanate, dropwise adding within 60min, and reacting at the temperature for 2.5h; 2.6g of 2, 2-dimethylolpropionic acid is completely dissolved in 3.0g of N, N-dimethylformamide, then is added into a reaction vessel, the temperature is regulated to 85 ℃, the reaction is carried out for 1.8 hours at the temperature, and 3.35g of methyl ethyl ketoxime is added into the reaction vessel for continuous thermal insulation reaction for 1.3 hours; after the reaction solution is cooled to 50 ℃, 1.96g of triethylamine is added into a reaction vessel, the temperature is adjusted to 55 ℃ and the pressure is minus 0.09Mpa after the reaction is carried out for 30min at the temperature of 50 ℃, 131.44g of deionized water is added after the recovered acetone is removed by reduced pressure distillation, and the comb-shaped water-based polyurethane dispersing agent is obtained after stirring at a high speed for 30min at the rotating speed of 3000 r/min.
Referring to fig. 2, an infrared spectrum of the comb-type aqueous polyurethane dispersant in this example is shown. At 3337cm -1 、1538cm -1 Is characterized by a stretching vibration and deformation vibration peak of N-H in carbamate (1710 cm) -1 Is the stretching vibration peak of C=O in the carbamate, and the three peaks are the characteristic absorption of the carbamateA peak. The asymmetric stretching vibration peak of C=N in carbamate is 1237cm -1 Where it is located. 2967cm -1 、2869cm -1 Where is-CH 3 and-CH 2 C-H stretching vibration peak of 1641cm -1 A stretching vibration peak of C=N, 1457cm -1 The position is a stretching vibration peak of C=C in benzene ring, 1373cm -1 The left and right are C-H ring skeletons in the aromatic ring to vibrate. The peak of the stretching vibration and bending vibration of C-O-C in the polyether chain is 1094cm -1 Broad peak 926cm -1 、868cm -1 Where it is located. 2300-2250 cm -1 No characteristic absorption peak of the-NCO was found, indicating that the-NCO had reacted completely. The target product is synthesized.
Example 3
(1) 28g of polyethylene glycol monomethyl ether 750, 7.17g of trimellitic anhydride and 35g of ethyl acetate are added into a reaction vessel with a stirrer and a condensation reflux device, the condensation reflux device and the stirrer are started, the temperature is regulated to 60 ℃ and the pressure is regulated to minus 0.08MPa after the reaction is carried out for 3.5 hours at 85 ℃, and the ethyl acetate is removed by reduced pressure distillation to obtain an intermediate I.
(2) 1.54g of boric acid and 5.32g of 1, 2-propanediol are added into a reaction vessel with a stirrer, stirring is started, and after 2.5 hours of reaction at 125 ℃,1, 2-propanediol borate is obtained; 6.01g of 1, 2-propanediol borate, 30g of intermediate I and 0.36g of p-toluenesulfonic acid are added into a reaction vessel with a stirrer, stirring is started, and the reaction is carried out for 2.5 hours at 135 ℃; cooling the reaction solution to below 90 ℃, adding 40g of deionized water, adding a condensing reflux device, starting condensing reflux, adjusting the temperature to 98 ℃, carrying out heat preservation reaction for 2 hours at the temperature, cooling to 30 ℃, and adding 55g of saturated sodium carbonate solution; regulating the temperature to 70 ℃ and the pressure to-0.08 MPa, distilling under reduced pressure to remove water, dissolving with anhydrous methanol, filtering, heating the filtrate to 50 ℃, and distilling under reduced pressure to remove recovered methanol under the condition that the pressure is-0.08 MPa to obtain an intermediate II.
(3) 28.56g of intermediate II, 30g of acetone, 9g of polypropylene glycol 1000 and 0.12g of dibutyltin dilaurate are added into a reaction vessel with a stirrer, a condensation reflux device and a dropping funnel; starting a condensing reflux device and a stirrer, heating to 80 ℃, gradually adding 16g of isophorone diisocyanate, dropwise adding within 60min, and reacting for 2h at the temperature; 2.07g of 2, 2-dimethylolpropionic acid is completely dissolved in 2.5g of N, N-dimethylformamide, then is added into a reaction vessel, the temperature is regulated to 90 ℃, the reaction is carried out for 1.5 hours at the temperature, and after the reaction is carried out at the temperature for 1 hour, 4.31g of methyl ethyl ketoxime is added into the reaction vessel for continuous thermal insulation reaction for 1 hour; after the reaction solution is cooled to 45 ℃, 1.56g of triethylamine is added into a reaction vessel, the temperature is adjusted to 55 ℃ and the pressure is minus 0.08Mpa after the reaction is carried out for 30min at the temperature of 45 ℃, 144g of deionized water is added after the recovered acetone is removed by reduced pressure distillation, and the comb-shaped water-based polyurethane dispersing agent is obtained after stirring for 40min at a high speed at the rotating speed of 2000 r/min.
Referring to fig. 3, an infrared spectrum of the comb-type aqueous polyurethane dispersant in this example is shown. At 3337cm -1 、1538cm -1 Is characterized by a stretching vibration and deformation vibration peak of N-H in carbamate, 1707cm -1 The stretching vibration peak of C=O in the carbamate is shown, and the three peaks are characteristic absorption peaks of the carbamate. The asymmetric stretching vibration peak of C=N in carbamate is 1259cm -1 Where it is located. 2965cm -1 、2874cm -1 Where is-CH 3 and-CH 2 C-H stretching vibration peak of 1650cm -1 A stretching vibration peak of C=N, 1454cm -1 The position is a stretching vibration peak of C=C in benzene ring, 1373cm -1 The left and right are C-H ring skeletons in the aromatic ring to vibrate. The peak of the stretching vibration and bending vibration of C-O-C in the polyether chain is 1093cm -1 Broad peak, 928cm -1 、865cm -1 Where it is located. 2300-2250 cm -1 No characteristic absorption peak of the-NCO was found, indicating that the-NCO had reacted completely. The target product is synthesized.
Example 4
This example takes c.i. disperse blue 56 as an example, and the comb-type aqueous polyurethane dispersants for disperse dyes prepared by using examples 1,2 and 3 of the present invention were subjected to a dispersion performance test.
1. Grinding process
The specific grinding process comprises the following steps: the first step: adding deionized water, a dispersing agent and disperse dye with the formula dosage into a container, and pre-dispersing by using a stirrer; and a second step of: adding disperse dye, dispersant and deionized water in the amount of formula into a grinding cup, wherein zirconium beads account for 4/5 of the whole system, grinding for 2 hours by using a ball mill, and filtering to obtain dye dispersion.
Wherein, the specific formula (mass percent) of the disperse dye dispersoid is as follows:
disperse dye: 20 percent of
Dispersing agent: 8%
Deionized water: 72 percent of
2. Centrifugal stability test
And (3) centrifuging the dye dispersion diluted 2000 times at different rotation speeds by using a high-speed centrifuge, and evaluating the centrifugal stability according to the absorbance difference of the dye liquor at the upper layer and the lower layer, wherein the larger the centrifugal stability value is, the stronger the centrifugal stability is. Centrifugal stability of dye dispersion R is measured by the absorbance ratio A before and after centrifugation according to the formula x /A 0 The representation is:
R/％＝A x /A 0 ×100
wherein: a is that x -maximum absorbance of supernatant after centrifugation, L/(g.cm); a is that 0 Maximum absorbance of supernatant before centrifugation, L/(g.cm).
Comb-type aqueous polyurethane dispersant samples prepared in examples 1,2 and 3 and comparative sample were used for test results of centrifugal stability of dye dispersions prepared by grinding disperse dyes using commercially available dispersant NNO as a comparative example, see table 1.
TABLE 1
Claims (4)
1. The preparation method of the comb-type water-based polyurethane dispersing agent for the disperse dye is characterized by comprising the following steps of:
(1) Adding 40-60 parts of polyethylene glycol monomethyl ether, 14-17 parts of trimellitic anhydride and 40-60 parts of ethyl acetate into a reaction vessel with a stirrer and a condensation reflux device, starting the condensation reflux device and the stirrer, reacting at 80-90 ℃ for 3-4 h, regulating the temperature to 50-60 ℃ and the pressure to-0.08 to-0.1 MPa, and distilling under reduced pressure to remove and recycle ethyl acetate to obtain an intermediate I;
(2) Adding 3-5 parts of boric acid and 10-16 parts of 1, 2-propylene glycol into a reaction vessel with a stirrer, and reacting 2-3 h under the stirring condition at the temperature of 120-130 ℃ to obtain 1, 2-propylene glycol borate; adding 11-13 parts of 1, 2-propylene glycol borate, 40-60 parts of intermediate I and 0.5-0.75 part of p-toluenesulfonic acid into a reaction vessel with a stirrer, and reacting at 130-140 ℃ under stirring for 2-3 h; cooling the reaction liquid to below 90 ℃, adding 6080 parts of deionized water, adding a condensing reflux device, starting condensing reflux, adjusting the temperature to 95-100 ℃, reacting 2h under the condition of keeping the temperature, cooling to 20-30 ℃, and adding 80-110 parts of saturated sodium carbonate solution; regulating the temperature to 60-70 ℃ and the pressure to minus 0.08-minus 0.1MPa, distilling under reduced pressure to remove water, dissolving with absolute methanol, filtering, heating the filtrate to 30-40 ℃, distilling under reduced pressure to remove recovered methanol under the condition that the pressure is minus 0.08-minus 0.1MPa, and obtaining an intermediate II;
(3) Adding 40-60 parts of intermediate II, 40-60 parts of acetone, 18 parts of polyether glycol and 0.06-0.12 part of dibutyltin dilaurate into a reaction vessel with a stirrer, a condensing reflux device and a dropping funnel; starting a condensing reflux device and a stirrer, heating to 70-80 ℃, gradually adding 32 parts of isophorone diisocyanate, and reacting for 2-3 h under the condition of keeping the temperature at 70-80 ℃ after finishing dripping within 50-80 min; 4-7 parts of 2, 2-dimethylolpropionic acid is completely dissolved in 5-8 parts of N, N-dimethylformamide, then added into a reaction container, the temperature is regulated to 80-90 ℃ to react 1.5-2 h under the condition of keeping the temperature, and then 5-9 parts of methyl ethyl ketoxime are added into the reaction container to continuously react for 1-1.5 h under the condition of keeping the temperature; after the reaction liquid is cooled to 40-50 ℃, 3-5 parts of triethylamine is added into a reaction container, the reaction is carried out at the temperature of 40-50 ℃ under the condition of heat preservation for 0.5-1 and h, the pressure is regulated to be minus 0.08-minus 0.1Mpa, after the recovered acetone is removed by reduced pressure distillation, 250-290 parts of deionized water is added, and the mixture is stirred at a high speed for 0.5-1 h at the rotating speed of 1500-3000 r/min, thus obtaining the comb-type water-based polyurethane dispersing agent.
2. The method for preparing a comb-type aqueous polyurethane dispersant for disperse dyes according to claim 1, wherein: the number average molecular weight of the polyethylene glycol monomethyl ether in the step (1) is 500, 550, 600, 650, 700 and 750.
3. The method for preparing a comb-type aqueous polyurethane dispersant for disperse dyes according to claim 1, wherein: the polyether glycol in the step (3) is polypropylene glycol, and the number average molecular weight is 1000.
4. A comb-type aqueous polyurethane dispersant for disperse dyes obtained by the preparation method of claim 1.
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