CN112940559A - High-toughness resin coating internal crosslinking dispersant and preparation method thereof - Google Patents
High-toughness resin coating internal crosslinking dispersant and preparation method thereof Download PDFInfo
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- CN112940559A CN112940559A CN202110176389.5A CN202110176389A CN112940559A CN 112940559 A CN112940559 A CN 112940559A CN 202110176389 A CN202110176389 A CN 202110176389A CN 112940559 A CN112940559 A CN 112940559A
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- sodium
- polyether
- internal crosslinking
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- 239000002270 dispersing agent Substances 0.000 title claims abstract description 62
- 239000011347 resin Substances 0.000 title claims abstract description 28
- 229920005989 resin Polymers 0.000 title claims abstract description 28
- 238000000576 coating method Methods 0.000 title claims abstract description 27
- 239000011248 coating agent Substances 0.000 title claims abstract description 26
- 238000004132 cross linking Methods 0.000 title claims abstract description 23
- 238000002360 preparation method Methods 0.000 title abstract description 14
- 239000004721 Polyphenylene oxide Substances 0.000 claims abstract description 37
- 229920000570 polyether Polymers 0.000 claims abstract description 37
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 28
- 239000000178 monomer Substances 0.000 claims abstract description 19
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 15
- 239000003054 catalyst Substances 0.000 claims abstract description 7
- 125000002091 cationic group Chemical group 0.000 claims abstract description 7
- 239000012986 chain transfer agent Substances 0.000 claims abstract description 7
- 239000003638 chemical reducing agent Substances 0.000 claims abstract description 7
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 7
- 239000003999 initiator Substances 0.000 claims abstract description 7
- 230000003472 neutralizing effect Effects 0.000 claims abstract description 7
- 125000004122 cyclic group Chemical group 0.000 claims abstract description 5
- 238000006243 chemical reaction Methods 0.000 claims description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 12
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 12
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 claims description 12
- 238000010438 heat treatment Methods 0.000 claims description 11
- PAWSVPVNIXFKOS-UHFFFAOYSA-N 2-Amino-2-butenoic acid Natural products CC=C([NH3+])C([O-])=O PAWSVPVNIXFKOS-UHFFFAOYSA-N 0.000 claims description 10
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims description 10
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 10
- 238000001816 cooling Methods 0.000 claims description 10
- BYLSIPUARIZAHZ-UHFFFAOYSA-N 2,4,6-tris(1-phenylethyl)phenol Chemical compound C=1C(C(C)C=2C=CC=CC=2)=C(O)C(C(C)C=2C=CC=CC=2)=CC=1C(C)C1=CC=CC=C1 BYLSIPUARIZAHZ-UHFFFAOYSA-N 0.000 claims description 8
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 claims description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
- 239000001301 oxygen Substances 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- KWSLGOVYXMQPPX-UHFFFAOYSA-N 5-[3-(trifluoromethyl)phenyl]-2h-tetrazole Chemical compound FC(F)(F)C1=CC=CC(C2=NNN=N2)=C1 KWSLGOVYXMQPPX-UHFFFAOYSA-N 0.000 claims description 6
- 229910015900 BF3 Inorganic materials 0.000 claims description 6
- 239000004342 Benzoyl peroxide Substances 0.000 claims description 6
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 claims description 6
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 6
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 6
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 claims description 6
- 235000019400 benzoyl peroxide Nutrition 0.000 claims description 6
- 238000007599 discharging Methods 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 claims description 6
- 229910001379 sodium hypophosphite Inorganic materials 0.000 claims description 6
- 229940001584 sodium metabisulfite Drugs 0.000 claims description 6
- 235000010262 sodium metabisulphite Nutrition 0.000 claims description 6
- 238000003756 stirring Methods 0.000 claims description 6
- -1 aryl sulfonic acid Chemical compound 0.000 claims description 5
- 239000002994 raw material Substances 0.000 claims description 5
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 claims description 4
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 claims description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 4
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 4
- BWJUFXUULUEGMA-UHFFFAOYSA-N propan-2-yl propan-2-yloxycarbonyloxy carbonate Chemical compound CC(C)OC(=O)OOC(=O)OC(C)C BWJUFXUULUEGMA-UHFFFAOYSA-N 0.000 claims description 4
- DKIDEFUBRARXTE-UHFFFAOYSA-N 3-mercaptopropanoic acid Chemical compound OC(=O)CCS DKIDEFUBRARXTE-UHFFFAOYSA-N 0.000 claims description 3
- 230000032683 aging Effects 0.000 claims description 3
- 229910001870 ammonium persulfate Inorganic materials 0.000 claims description 3
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 claims description 3
- 239000012153 distilled water Substances 0.000 claims description 3
- DNJIEGIFACGWOD-UHFFFAOYSA-N ethyl mercaptane Natural products CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 claims description 3
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 claims description 3
- 230000001502 supplementing effect Effects 0.000 claims description 3
- OPSWAWSNPREEFQ-UHFFFAOYSA-K triphenoxyalumane Chemical compound [Al+3].[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1 OPSWAWSNPREEFQ-UHFFFAOYSA-K 0.000 claims description 3
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 claims description 3
- AEUVIXACNOXTBX-UHFFFAOYSA-N 1-sulfanylpropan-1-ol Chemical compound CCC(O)S AEUVIXACNOXTBX-UHFFFAOYSA-N 0.000 claims description 2
- 239000005913 Maltodextrin Substances 0.000 claims description 2
- 229920002774 Maltodextrin Polymers 0.000 claims description 2
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 claims description 2
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 claims description 2
- SLINHMUFWFWBMU-UHFFFAOYSA-N Triisopropanolamine Chemical compound CC(O)CN(CC(C)O)CC(C)O SLINHMUFWFWBMU-UHFFFAOYSA-N 0.000 claims description 2
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 claims description 2
- 235000010323 ascorbic acid Nutrition 0.000 claims description 2
- 229960005070 ascorbic acid Drugs 0.000 claims description 2
- 239000011668 ascorbic acid Substances 0.000 claims description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 2
- 239000003729 cation exchange resin Substances 0.000 claims description 2
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 claims description 2
- BLCKNMAZFRMCJJ-UHFFFAOYSA-N cyclohexyl cyclohexyloxycarbonyloxy carbonate Chemical compound C1CCCCC1OC(=O)OOC(=O)OC1CCCCC1 BLCKNMAZFRMCJJ-UHFFFAOYSA-N 0.000 claims description 2
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims description 2
- 239000012433 hydrogen halide Substances 0.000 claims description 2
- 229910000039 hydrogen halide Inorganic materials 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims description 2
- 239000012280 lithium aluminium hydride Substances 0.000 claims description 2
- 229940035034 maltodextrin Drugs 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 150000002892 organic cations Chemical group 0.000 claims description 2
- 150000002903 organophosphorus compounds Chemical class 0.000 claims description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 2
- XWGJFPHUCFXLBL-UHFFFAOYSA-M rongalite Chemical compound [Na+].OCS([O-])=O XWGJFPHUCFXLBL-UHFFFAOYSA-M 0.000 claims description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 2
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 2
- 239000012260 resinous material Substances 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract description 5
- 238000001179 sorption measurement Methods 0.000 abstract description 4
- 239000008367 deionised water Substances 0.000 abstract 1
- 229910021641 deionized water Inorganic materials 0.000 abstract 1
- 239000000203 mixture Substances 0.000 description 12
- 239000003822 epoxy resin Substances 0.000 description 8
- 229920000647 polyepoxide Polymers 0.000 description 8
- 239000000049 pigment Substances 0.000 description 6
- 239000006185 dispersion Substances 0.000 description 5
- 239000002245 particle Substances 0.000 description 5
- 239000000463 material Substances 0.000 description 4
- 239000012766 organic filler Substances 0.000 description 4
- 239000003973 paint Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 230000001070 adhesive effect Effects 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 238000005452 bending Methods 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 230000007547 defect Effects 0.000 description 2
- 230000002209 hydrophobic effect Effects 0.000 description 2
- 239000012860 organic pigment Substances 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- 239000010703 silicon Substances 0.000 description 2
- 230000035882 stress Effects 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 241000233805 Phoenix Species 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 238000005189 flocculation Methods 0.000 description 1
- 230000016615 flocculation Effects 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000004377 microelectronic Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 229920000056 polyoxyethylene ether Polymers 0.000 description 1
- 229940051841 polyoxyethylene ether Drugs 0.000 description 1
- 229920002503 polyoxyethylene-polyoxypropylene Polymers 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 230000003014 reinforcing effect Effects 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 229940001607 sodium bisulfite Drugs 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 238000007614 solvation Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 229920002725 thermoplastic elastomer Polymers 0.000 description 1
- 239000004636 vulcanized rubber Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002912 waste gas Substances 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
- 238000004804 winding Methods 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/40—Additives
- C09D7/65—Additives macromolecular
-
- 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
- C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
- C08F283/06—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polyethers, polyoxymethylenes or polyacetals
- C08F283/065—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polyethers, polyoxymethylenes or polyacetals on to unsaturated polyethers, polyoxymethylenes or polyacetals
-
- 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
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/26—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds
- C08G65/2603—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen
- C08G65/2606—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen containing hydroxyl groups
- C08G65/2612—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen containing hydroxyl groups containing aromatic or arylaliphatic hydroxyl groups
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Polymers & Plastics (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
- Polyethers (AREA)
- Paints Or Removers (AREA)
Abstract
The invention provides a high-toughness resin coating inner crosslinking type dispersing agent and a preparation method thereof, wherein the dispersing agent is mainly prepared from the following components: 36.70-38.63 parts of polyether alcohol head, 257.74-271.67 parts of cyclic monomer, 0.5-1.2 parts of catalyst, 76.56-80.70 parts of cationic monomer, 1.5-3.9 parts of reducing agent, 2.4-5.8 parts of initiator, 2.2-6.1 parts of neutralizing agent, 0.5-2.7 parts of chain transfer agent and the balance of deionized water. According to the invention, polyether is used as a dispersant branched chain to prepare the high-toughness resin internal crosslinking dispersant with short side chains, the short side chains are used for improving the adsorption performance of the dispersant, and the acid-ether ratio is reduced, so that the space density of the short side chains is improved to improve the steric hindrance effect of the dispersant.
Description
Technical Field
The invention belongs to the technical field of dispersing agents, and particularly relates to a high-toughness resin coating inner crosslinking dispersing agent and a preparation method thereof.
Background
The epoxy resin adhesive has the characteristics of excellent bonding performance, electric insulation performance, chemical corrosion resistance, low curing shrinkage rate and the like, is widely applied to the fields of aerospace, automobiles, microelectronics, precision machinery and the like, but has the defects of large internal stress, brittle quality and the like after curing, so that the wider application of the epoxy resin adhesive is limited. Aiming at the brittleness of an epoxy resin system, the most effective toughening method is to toughen and modify the epoxy resin.
Patent CN110229341A discloses an organosilicon resin-based nonionic hyperdispersant, which relates to an organosilicon resin-based nonionic hyperdispersant and a preparation method thereof, and the organosilicon resin-based nonionic hyperdispersant is prepared by mixing epoxy-terminated silicone oil and single-ended amino polyether according to the mass ratio of 1: 1.1-1.1: 1, and reacting for 2-6 hours at the temperature of 80-140 ℃. The hydrophobic part of the organic silicon resin-based nonionic hyperdispersant is organic silicon resin, and the hydrophilic part is single-end amino polyoxyethylene ether or single-end amino polyoxyethylene polyoxypropylene ether. The water-based paint prepared by the dispersant has high solid content, good fluidity, high stability and bright color; the reaction can be carried out at a lower temperature, waste water and waste gas are basically not discharged, but horizontal adsorption in the dispersant is more, so that the utilization rate of the solvation chain segment is greatly reduced.
Patent CN104334265A discloses a nonaqueous dispersant for resin layers having excellent water resistance and a method for producing the same. The invention provides a nonaqueous dispersant which has excellent dispersibility and dispersion stability and can form a resin layer with excellent water resistance. But the bonding on the surface of the particles with lower polarity or non-polar particles is not firm, and the particles are easy to desorb, so that the dispersed particles are re-flocculated.
Patent CN110540639A discloses a parallel-connection type high-molecular water-based organic pigment dispersant, and preparation and application thereof. The invention provides a parallel-connection type high-molecular water-based pigment dispersant, which has a comb-shaped branched structure and comprises a naphthalene ring and a peripheral ethylene oxide/propylene oxide polymer long chain, wherein the structural formula is as follows: in the structural formula, n is 26-38, x is 15-22, and y is 44-63. The invention also provides a preparation method and application of the parallel-connection type high-molecular water-based pigment dispersant. The parallel-connection type high-molecular water-based pigment dispersing agent has excellent dispersion stability, storage stability and redissolution property on organic pigments, high grinding efficiency, strong viscosity reduction property and good color development property; the pigment has strong universality, is suitable for various inorganic, organic and mixed pigments, and is particularly suitable for the fields of high-solid pigment-containing color pastes, water-based paint systems, printing ink, electronic ink jet and the like. The hydrophobic color paste can maintain that the aqueous color paste does not flocculate and deposit for a long time (as long as 30 days), so that the good stability of a system is ensured, but the oleophilic group does not have enough carbon chain length and cannot generate enough steric hindrance effect in a non-aqueous dispersion system.
The above patents still have the defects of insufficient adsorption capacity of the dispersing agent, easy flocculation generation, insufficient steric hindrance, general dispersing effect and the like.
Disclosure of Invention
The invention aims to provide a crosslinking dispersant in a high-toughness resin coating and a preparation method thereof.
The invention concept of the invention is as follows: the invention discloses a cross-linking dispersing agent in a high-toughness resin coating and a preparation method thereof. According to the invention, styrenated phenol is reacted with ethylene oxide and propylene oxide to generate a polyether monomer with a weight average molecular weight of 1200, the prepared polyether monomer is reacted with 2-amino-2-butenoic acid to generate a dispersant molecule, and then the dispersant molecule is used as a branched chain of the dispersant molecule, and as the alcohol head is provided with a benzene ring and the prepared polyether has a molecular weight of 1200, the main chain of the molecular chain has rigidity, the problem that the molecular chain of the dispersant is too flexible and easy to wind can be effectively solved, and the adaptability of the dispersant is enhanced.
The technical scheme of the invention is as follows:
the cross-linking type dispersing agent in the high-toughness resin coating is prepared from the following components in parts by weight, wherein the total mass of the raw materials is 1000 parts, and the components comprise:
36.70-38.63 parts of polyether alcohol head;
257.74-271.67 parts of cyclic monomer;
0.5-1.2 parts of a catalyst;
76.56-80.70 parts of cationic monomer;
1.5-3.9 parts of a reducing agent;
2.4-5.8 parts of an initiator;
0.5-2.7 parts of a chain transfer agent;
2.2-6.1 parts of a neutralizing agent;
the balance of water.
Further, the solid content of the crosslinking type dispersing agent in the high-toughness resin coating is 38-42%, and the optimal solid content is 40%.
Preferably, the polyether alcohol head is styrenated phenol.
Preferably, the cyclic monomers are ethylene oxide and propylene oxide.
Preferably, the catalyst is one or more of anhydrous aluminum chloride, boron trifluoride, concentrated sulfuric acid, hydrogen halide, aryl sulfonic acid, an organic phosphorus compound, carboxylic acid, organic cation exchange resin, aluminum phenoxide, sodium hydroxide, potassium hydroxide, sodium cyanide, lithium aluminum hydride, boron trifluoride vinyl ether and DMC, and the most preferred is a composition of the aryl sulfonic acid and the aluminum phenoxide with the mass ratio of 1:1.
Preferably, the cationic monomer is 2-amino-2-butenoic acid.
Preferably, the acid ether (molar ratio) is 3.1: 1.
Preferably, the reducing agent is one or more of sodium hydrosulfite, ascorbic acid, sodium formaldehyde sulfoxylate, maltodextrin, sodium bisulfite, sodium metabisulfite and sodium hypophosphite, and the most preferred is a composition of sodium metabisulfite and sodium hypophosphite with the mass ratio of 1: 2.
Preferably, the initiator is one or more of ammonium persulfate, azobisisobutyronitrile, diisopropyl peroxydicarbonate, Benzoyl Peroxide (BPO), di-tert-butyl peroxide (DTBP) and dicyclohexyl peroxydicarbonate, and a composition of ammonium persulfate and benzoyl peroxide in a mass ratio of 3:1 is most preferred.
Preferably, the chain transfer agent is one or more of thioglycolic acid, mercaptopropionic acid, mercaptoethanol and mercaptopropanol, and most preferably a composition of the mercaptopropionic acid and the mercaptoethanol with the mass ratio of 2: 3.
Preferably, the neutralizing agent is one or more of sodium hydroxide, potassium hydroxide, sodium carbonate, sodium bicarbonate, potassium carbonate, sodium methoxide, sodium ethoxide, ethanolamine, diethanolamine, triethanolamine and triisopropanolamine, and the most preferred is a composition of sodium methoxide and ethanolamine with the mass ratio of 3: 4.
The preparation method of the high-toughness resin coating internal crosslinking dispersant comprises the following operation steps in sequence:
the method comprises the following steps: 35.70-37.63 parts of polyether alcohol head and 0.5-1.2 parts of catalyst are added into a high-pressure reaction kettle provided with a stirrer and a thermometer, after 3 times of nitrogen replacement, vacuumizing is started to gauge pressure of-0.098 MPa, then the temperature is raised to 110 plus materials and 120 ℃, dehydration is started for 1-1.5h, the oxygen content is measured, after the oxygen content is qualified (the oxygen content is less than 5ppm), the temperature is reduced to 105 ℃, 257.74-271.67 parts of annular monomer are continuously introduced, the gauge pressure is controlled to be less than 0.6MPa, after the introduction is finished, the temperature is kept at 135 ℃ for 1.5-3h, aging is carried out to negative pressure, the temperature is reduced, and discharging is carried out, thus obtaining the crude polyether.
Step two: placing the crude polyether in a reaction kettle, replacing for 3 times by nitrogen under negative pressure, heating to 110-plus-material temperature of 120 ℃, stirring for 1-2h, cooling to 80-90 ℃, adding distilled water, stirring for 1-2h, heating to 115-plus-material temperature while vacuumizing, cooling and discharging to obtain the finished polyether.
Step three: adding the prepared finished polyether into a reaction kettle, heating to 40-50 ℃ by adopting water bath, reacting for 2-3 hours, and then preserving heat for 1-2 hours. Preparing solution A from 1.5-3.9 parts of reducing agent, 2.4-5.8 parts of initiator, 0.5-2.7 parts of chain transfer agent and water, preparing solution B from 76.56-80.70 parts of cationic monomer, 0.5-1.0 part of polyether alcohol head and water, and dripping A, B liquid into a reaction kettle by using a dripping pump, wherein the solution A is dripped for 0.5-1 hour, and the solution B is dripped for 1-2 hours to prepare the polyether dispersant.
Step four: adding 2.2-6.1 parts of neutralizing agent into the prepared coating dispersant, and supplementing water until the total mass is 1000 to obtain the required polyether dispersant solution.
Compared with the prior art, the invention has the advantages and beneficial effects that:
1. the polyether monomer is prepared as a reaction raw material, so that part of raw material cost and transportation cost are saved, and the polyether prepared by the water washing refining method has high purity and is beneficial to reaction.
2. According to the invention, styrenated phenol is used as an alcohol head to synthesize polyether, a benzene ring group is introduced on a branched chain of the dispersing agent, and the benzene ring group is used as a rigid group to limit the swinging of a main chain of the dispersing agent, so that the molecules of the dispersing agent are prevented from winding, and the adaptability of the dispersing agent is improved. And the alcohol head has 2 double bonds, and is easy to crosslink during polymerization to form a net structure, so that when the alcohol head is used as a dispersing agent in the organic filler, the alcohol head also has a certain reinforcing effect to enhance toughness.
3. The molecular weight of the polyether prepared by the invention is 1200, and the short branch chain length enables the dispersant molecule to have excellent adsorption performance, so that the coating particles can be well coated, and a good dispersion effect is achieved, thereby enhancing the toughness.
Drawings
FIG. 1 SEM examination of a coating sample prepared from the dispersant and epoxy resin of example 1.
FIG. 2 SEM examination of coating samples prepared from SN5040 oleo coating dispersant and epoxy resin.
Detailed Description
The applicant will make further detailed descriptions of technical solutions and advantages of the present invention with reference to specific examples, but it should be understood that the following examples should not be construed as limiting the scope of the claims of the present application in any way.
Example 1
A high-toughness resin coating inner cross-linking dispersant and a preparation method thereof are polymerized by the following components:
36.89 parts of styrenated phenol;
181.26 parts of ethylene oxide;
79.31 parts of propylene oxide;
0.6 part of boron trifluoride;
76.98 parts of 2-amino-2-butenoic acid;
1.7 parts of a composition of sodium metabisulfite and sodium hypophosphite in a mass ratio of 1: 2;
3.6 parts of a composition of diisopropyl peroxydicarbonate and benzoyl peroxide in a mass ratio of 1: 1;
1.1 parts of mercaptoacetic acid;
4.2 parts of a composition of sodium methoxide and ethanolamine with the mass ratio of 3: 4;
the balance of water, the total mass is 1000 parts.
The crosslinking type dispersing agent in the high-toughness resin coating and the preparation method thereof are characterized in that the preparation process sequentially comprises the following operation steps:
the method comprises the following steps: adding 36.89 parts of styrenated phenol and 0.6 part of boron trifluoride into a high-pressure reaction kettle provided with a stirrer and a thermometer, performing nitrogen replacement for 3 times, vacuumizing to gauge pressure of-0.098 MPa, heating to 110 ℃, dehydrating for 1.5 hours, measuring the oxygen content, cooling to 105 ℃ after the oxygen content is qualified, continuously introducing 181.26 parts of ethylene oxide and 79.31 parts of propylene oxide, controlling the gauge pressure to be less than 0.6MPa, keeping the temperature at 129 ℃ after the introduction for 2.3 hours, aging to negative pressure, cooling and discharging to obtain the crude polyether.
Step two: and (3) placing the crude polyether into a reaction kettle, performing nitrogen negative pressure replacement for 3 times, heating to 116 ℃, stirring for 1.6h, cooling to 85 ℃, adding distilled water, stirring for 1.1h, heating to 117 ℃ while vacuumizing, cooling, and discharging to obtain the finished polyether.
Step three: adding the prepared finished polyether into a reaction kettle, heating to 42 ℃ by adopting water bath, reacting for 2.8 hours, and then preserving heat for 1.0 hour. Preparing a solution A from 1.7 parts of a composition of sodium metabisulfite and sodium hypophosphite, 3.6 parts of a composition of diisopropyl peroxydicarbonate and benzoyl peroxide, 1.1 parts of thioglycolic acid and water, and preparing a solution B from 76.98 parts of 2-amino-2-butenoic acid, 1.0 part of styrenated phenol and water, and adding A, B parts of solution A into a reaction kettle dropwise by using a dropwise adding pump for 0.6 hour and adding the solution B dropwise for 1.5 hours, wherein the mass ratio of the composition of sodium metabisulfite and sodium hypophosphite is 1: 2. To prepare the polyether dispersant.
Step four: adding 4.2 parts of the composition of sodium methoxide and ethanolamine in a mass ratio of 3:4 into the prepared coating dispersant, and supplementing water until the total mass is 1000 to obtain the required polyether dispersant solution.
The raw material components and process parameters in examples 2 to 6 are shown in tables 1 to 2, and the parts not listed are the same as in example 1.
TABLE 1
TABLE 2
The dispersant prepared in the examples and the SN5040 oily paint dispersant produced by hexacyclic chemical industry were each added to a Phoenix brand E44 epoxy resin produced by a tin-free resin factory for tensile fracture measurement with reference to "determination of tensile stress strain properties of vulcanized rubber or thermoplastic rubber" (GB/T528-one 2009).
TABLE 3 elongation at break
TABLE 4 flexural tensile Properties
The above table shows that the embodiment has better tensile strength and bending strain, obviously improved elongation at break and bending strength, and better mechanical property.
Coatings prepared from the dispersant of example 1 and the dispersant of SN5040 oily paint and epoxy resin respectively are examined by SEM to obtain figures 1 and 2.
The results show that the dispersant of example 1 allows better dispersion of the resin and thus better toughness.
In conclusion, the embodiment of the invention greatly improves the toughness of the material and simultaneously keeps higher strength.
The dispersant prepared by the invention is a cross-linking dispersant in a high-toughness resin coating and a preparation method thereof. The invention adopts styrenated phenol with better activity as alcohol head to synthesize polyether monomer, the monomer has a multi-double bond structure, and partial crosslinking can occur during polymerization reaction to form a net-shaped crosslinking structure, so that the surface adhesive property of the organic filler is improved while the dispersity of the organic filler is improved, the crosslinking capability of the polymer is improved when the performance of the polymer is improved by the organic filler, and the toughening effect is achieved.
Claims (7)
1. The high-toughness resin coating internal crosslinking dispersant is polymerized by the following components, the total mass of the raw materials is 1000 parts, and the components comprise:
36.70-38.63 parts of polyether alcohol head;
257.74-271.67 parts of cyclic monomer;
0.5-1.2 parts of a catalyst;
76.56-80.70 parts of cationic monomer;
1.5-3.9 parts of a reducing agent;
2.4-5.8 parts of an initiator;
0.5-2.7 parts of a chain transfer agent;
2.2-6.1 parts of a neutralizing agent;
the balance of water;
the polyether alcohol head is styrenated phenol;
the cyclic monomer is ethylene oxide and propylene oxide;
the cationic monomer is 2-amino-2-butenoic acid.
2. The high toughness resin based coating internal crosslinking type dispersant of claim 1, wherein: the catalyst is composed of one or more of anhydrous aluminum chloride, boron trifluoride, concentrated sulfuric acid, hydrogen halide, aryl sulfonic acid, an organic phosphorus compound, carboxylic acid, organic cation exchange resin, aluminum phenoxide, sodium hydroxide, potassium hydroxide, sodium cyanide, lithium aluminum hydride, boron trifluoride vinyl ether and DMC.
3. The high toughness resin based coating internal crosslinking type dispersant of claim 1, wherein: the reducing agent is one or more of sodium hydrosulfite, ascorbic acid, sodium formaldehyde sulfoxylate, maltodextrin, sodium hydrosulfite, sodium metabisulfite and sodium hypophosphite.
4. The high toughness resin based coating internal crosslinking type dispersant of claim 1, wherein: the initiator is one or more of ammonium persulfate, azobisisobutyronitrile, diisopropyl peroxydicarbonate, benzoyl peroxide, di-tert-butyl peroxide and dicyclohexyl peroxydicarbonate.
5. The high toughness resin based coating internal crosslinking type dispersant of claim 1, wherein: the chain transfer agent is one or more of thioglycolic acid, mercaptopropionic acid, mercaptoethanol and mercaptopropanol.
6. The high toughness resin based coating internal crosslinking type dispersant of claim 1, wherein: the neutralizing agent is one or more of sodium hydroxide, potassium hydroxide, sodium carbonate, sodium bicarbonate, potassium carbonate, sodium methoxide, sodium ethoxide, ethanolamine, diethanolamine, triethanolamine and triisopropanolamine.
7. The process for preparing a dispersant of the internal crosslinking type for a coating of a high toughness resinous material as claimed in claim 1, which comprises the following steps in order:
the method comprises the following steps: adding 35.70-37.63 parts of polyether alcohol head and 0.5-1.2 parts of catalyst into a high-pressure reaction kettle provided with a stirrer and a thermometer, performing nitrogen replacement for 3 times, vacuumizing to gauge pressure of-0.098 MPa, heating to 110-120 ℃, dehydrating for 1-1.5h, measuring the oxygen content, cooling to 105 ℃ after the oxygen content is qualified, continuously introducing 257.74-271.67 parts of annular monomer, controlling the gauge pressure to be less than 0.6MPa, preserving the heat at 135 ℃ of 125-180 ℃ for 1.5-3h, aging to negative pressure, cooling and discharging to obtain crude polyether;
step two: placing the crude polyether in a reaction kettle, replacing for 3 times by nitrogen under negative pressure, heating to 110-90 ℃, stirring for 1-2h, cooling to 80-90 ℃, adding distilled water, stirring for 1-2h, heating to 115-125 ℃ while vacuumizing, cooling and discharging to obtain a finished polyether product;
step three: adding the prepared finished polyether into a reaction kettle, heating to 40-50 ℃ by adopting water bath, reacting for 2-3 hours, and then preserving heat for 1-2 hours; preparing 1.5-3.9 parts of reducing agent, 2.4-5.8 parts of initiator, 0.5-2.7 parts of chain transfer agent and water into solution A, preparing 76.56-80.70 parts of cationic monomer, 0.5-1.0 part of polyether alcohol head and water into solution B, dripping A, B liquid into a reaction kettle by using a dripping pump, wherein the solution A is dripped for 0.5-1 hour, and the solution B is dripped for 1-2 hours to prepare polyether dispersant;
step four: adding 2.2-6.1 parts of neutralizing agent into the prepared coating dispersant, and supplementing water until the total mass is 1000 to obtain the required polyether dispersant solution.
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| JPH0699060A (en) * | 1992-09-18 | 1994-04-12 | Kao Corp | Glycol-based dispersion of calcium carbonate |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN111875777A (en) * | 2020-07-24 | 2020-11-03 | 珠海市金团化学品有限公司 | Water-based high-molecular polyurethane dispersant and preparation method thereof |
| CN111875777B (en) * | 2020-07-24 | 2022-05-13 | 珠海市金团化学品有限公司 | Water-based high-molecular polyurethane dispersant and preparation method thereof |
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