CN109354824A - A kind of aqueous photo-curing modified melamine-formaldehyde impregnating resin and preparation method thereof - Google Patents
A kind of aqueous photo-curing modified melamine-formaldehyde impregnating resin and preparation method thereof Download PDFInfo
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- CN109354824A CN109354824A CN201811148371.9A CN201811148371A CN109354824A CN 109354824 A CN109354824 A CN 109354824A CN 201811148371 A CN201811148371 A CN 201811148371A CN 109354824 A CN109354824 A CN 109354824A
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- Prior art keywords
- melamine
- parts
- formaldehyde
- resin
- curing modified
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- 238000000016 photochemical curing Methods 0.000 title claims abstract description 77
- 229920005989 resin Polymers 0.000 title claims abstract description 61
- 239000011347 resin Substances 0.000 title claims abstract description 61
- IVJISJACKSSFGE-UHFFFAOYSA-N formaldehyde;1,3,5-triazine-2,4,6-triamine Chemical class O=C.NC1=NC(N)=NC(N)=N1 IVJISJACKSSFGE-UHFFFAOYSA-N 0.000 title claims abstract description 38
- 238000002360 preparation method Methods 0.000 title claims abstract description 15
- 229920000877 Melamine resin Polymers 0.000 claims abstract description 56
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 claims abstract description 30
- 229920005749 polyurethane resin Polymers 0.000 claims abstract description 26
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 26
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims abstract description 24
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 claims abstract description 19
- 239000002994 raw material Substances 0.000 claims abstract description 17
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims abstract description 16
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims abstract description 13
- 239000000178 monomer Substances 0.000 claims abstract description 13
- AZIQALWHRUQPHV-UHFFFAOYSA-N prop-2-eneperoxoic acid Chemical compound OOC(=O)C=C AZIQALWHRUQPHV-UHFFFAOYSA-N 0.000 claims abstract description 13
- 235000019260 propionic acid Nutrition 0.000 claims abstract description 12
- 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 abstract description 12
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 11
- 125000005442 diisocyanate group Chemical group 0.000 claims abstract description 8
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 8
- 239000003054 catalyst Substances 0.000 claims abstract description 7
- 239000003112 inhibitor Substances 0.000 claims abstract description 7
- 150000005846 sugar alcohols Polymers 0.000 claims abstract description 7
- -1 neutralizer Substances 0.000 claims abstract description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 95
- 238000006243 chemical reaction Methods 0.000 claims description 32
- 230000035484 reaction time Effects 0.000 claims description 21
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 14
- 239000006185 dispersion Substances 0.000 claims description 13
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 claims description 12
- 150000002148 esters Chemical class 0.000 claims description 11
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 10
- 238000002464 physical blending Methods 0.000 claims description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 9
- 239000000839 emulsion Substances 0.000 claims description 8
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 claims description 8
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 6
- 229910052797 bismuth Inorganic materials 0.000 claims description 6
- 238000001816 cooling Methods 0.000 claims description 6
- 229920001610 polycaprolactone Polymers 0.000 claims description 6
- 239000004632 polycaprolactone Substances 0.000 claims description 6
- 229920000909 polytetrahydrofuran Polymers 0.000 claims description 6
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 claims description 5
- 150000002009 diols Chemical class 0.000 claims description 5
- 238000004945 emulsification Methods 0.000 claims description 5
- 239000012948 isocyanate Substances 0.000 claims description 5
- 229960003742 phenol Drugs 0.000 claims description 5
- 229920001223 polyethylene glycol Polymers 0.000 claims description 5
- 229920001451 polypropylene glycol Polymers 0.000 claims description 5
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
- 239000002202 Polyethylene glycol Substances 0.000 claims description 4
- 239000004372 Polyvinyl alcohol Substances 0.000 claims description 4
- HMYHKGAOZUSXKF-UHFFFAOYSA-N ethylideneurea 2-methylprop-2-enoic acid Chemical compound C(C)=NC(=O)N.C(C(=C)C)(=O)O HMYHKGAOZUSXKF-UHFFFAOYSA-N 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- 229920002451 polyvinyl alcohol Polymers 0.000 claims description 4
- OVBFMUAFNIIQAL-UHFFFAOYSA-N 1,4-diisocyanatobutane Chemical compound O=C=NCCCCN=C=O OVBFMUAFNIIQAL-UHFFFAOYSA-N 0.000 claims description 3
- XESZUVZBAMCAEJ-UHFFFAOYSA-N 4-tert-butylcatechol Chemical compound CC(C)(C)C1=CC=C(O)C(O)=C1 XESZUVZBAMCAEJ-UHFFFAOYSA-N 0.000 claims description 3
- UWHCKJMYHZGTIT-UHFFFAOYSA-N Tetraethylene glycol, Natural products OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 claims description 3
- 150000001408 amides Chemical class 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 claims description 3
- 239000005058 Isophorone diisocyanate Substances 0.000 claims description 2
- CNCOEDDPFOAUMB-UHFFFAOYSA-N N-Methylolacrylamide Chemical compound OCNC(=O)C=C CNCOEDDPFOAUMB-UHFFFAOYSA-N 0.000 claims description 2
- OMRDSWJXRLDPBB-UHFFFAOYSA-N N=C=O.N=C=O.C1CCCCC1 Chemical compound N=C=O.N=C=O.C1CCCCC1 OMRDSWJXRLDPBB-UHFFFAOYSA-N 0.000 claims description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 2
- 239000004202 carbamide Substances 0.000 claims description 2
- 230000008859 change Effects 0.000 claims description 2
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 claims description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 125000002252 acyl group Chemical group 0.000 claims 1
- 150000001336 alkenes Chemical class 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 235000013877 carbamide Nutrition 0.000 claims 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims 1
- 125000003944 tolyl group Chemical group 0.000 claims 1
- 229920002635 polyurethane Polymers 0.000 description 8
- 239000004814 polyurethane Substances 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 239000004640 Melamine resin Substances 0.000 description 5
- RACKNKCHAIASIK-UHFFFAOYSA-N C(C)=NC(=O)N.C(C=C)(=O)O Chemical compound C(C)=NC(=O)N.C(C=C)(=O)O RACKNKCHAIASIK-UHFFFAOYSA-N 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- 238000007385 chemical modification Methods 0.000 description 4
- 230000004048 modification Effects 0.000 description 4
- 238000012986 modification Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 3
- JIGUICYYOYEXFS-UHFFFAOYSA-N 3-tert-butylbenzene-1,2-diol Chemical compound CC(C)(C)C1=CC=CC(O)=C1O JIGUICYYOYEXFS-UHFFFAOYSA-N 0.000 description 2
- IWLBIFVMPLUHLK-UHFFFAOYSA-N azane;formaldehyde Chemical compound N.O=C IWLBIFVMPLUHLK-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 238000013007 heat curing Methods 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- JMANVNJQNLATNU-UHFFFAOYSA-N oxalonitrile Chemical compound N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 description 2
- 239000003973 paint Substances 0.000 description 2
- 238000003847 radiation curing Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- UOFRJXGVFHUJER-UHFFFAOYSA-N 2-[bis(2-hydroxyethyl)amino]ethanol;hydrate Chemical compound [OH-].OCC[NH+](CCO)CCO UOFRJXGVFHUJER-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 238000003486 chemical etching Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 229910001947 lithium oxide Inorganic materials 0.000 description 1
- GLXDVVHUTZTUQK-UHFFFAOYSA-M lithium;hydroxide;hydrate Chemical compound [Li+].O.[OH-] GLXDVVHUTZTUQK-UHFFFAOYSA-M 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 239000009719 polyimide resin Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical group CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- 238000005829 trimerization reaction Methods 0.000 description 1
- 238000009941 weaving Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L61/00—Compositions of condensation polymers of aldehydes or ketones; Compositions of derivatives of such polymers
- C08L61/20—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen
- C08L61/32—Modified amine-aldehyde condensates
-
- 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
- C08G12/00—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen
- C08G12/02—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes
- C08G12/26—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with heterocyclic compounds
- C08G12/30—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with heterocyclic compounds with substituted triazines
- C08G12/32—Melamines
-
- 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
- C08G12/00—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen
- C08G12/02—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes
- C08G12/40—Chemically modified polycondensates
-
- 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
- C08G18/30—Low-molecular-weight compounds
- C08G18/34—Carboxylic acids; Esters thereof with monohydroxyl compounds
- C08G18/348—Hydroxycarboxylic acids
-
- 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
- C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
- C08G18/4266—Polycondensates having carboxylic or carbonic ester groups in the main chain prepared from hydroxycarboxylic acids and/or lactones
- C08G18/4269—Lactones
- C08G18/4277—Caprolactone and/or substituted caprolactone
-
- 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
- C08G18/40—High-molecular-weight compounds
- C08G18/48—Polyethers
- C08G18/4854—Polyethers containing oxyalkylene groups having four carbon atoms in the alkylene group
-
- 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
- C08G18/67—Unsaturated compounds having active hydrogen
- C08G18/671—Unsaturated compounds having only one group containing active hydrogen
- C08G18/672—Esters of acrylic or alkyl acrylic acid having only one group containing active hydrogen
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2312/00—Crosslinking
- C08L2312/06—Crosslinking by radiation
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Phenolic Resins Or Amino Resins (AREA)
- Macromonomer-Based Addition Polymer (AREA)
Abstract
The invention discloses a kind of aqueous photo-curing modified melamine-formaldehyde impregnating resins, include the following components'mass percentage, watersoluble melamine-formaldehyde resin 70-90%, photocuring waterborne polyurethane resin 10-30%；Wherein, the raw material of the watersoluble melamine-formaldehyde resin includes melamine, 37wt.% formalin, modifying agent, caprolactam, acrylate co-monomers, water；The raw material of the photocuring waterborne polyurethane resin includes diisocyanate, polyalcohol, dihydromethyl propionic acid, monohydroxy acrylate, polymerization inhibitor, catalyst, neutralizer, water.The present invention correspondingly provides a kind of preparation method of above-mentioned resin.The high combination properties such as aqueous photo-curing modified melamine-formaldehyde impregnating resin of the invention has excellent stability, surface hardness and wearability, are with a wide range of applications.
Description
Technical field
The invention belongs to coating material solidified fields more particularly to a kind of melamino-formaldehyde impregnating resin and preparation method thereof.
Background technique
Melamine resin belongs to thermosetting resin, have it is fire-retardant, water-fast, heat-resisting, ageing-resistant, resistant to chemical etching,
There are good insulation performance, glossiness and mechanical strength, is widely used in the row such as wood furniture, coating, papermaking, weaving, leather
Industry, but its stability is poor, Storage period is short, solidify after brittleness it is big the disadvantages of limit its further extensive use.
There are two ways to improving flexibility, resin stability at present: physical modification and chemical modification.Physical modification is main
Improve the toughness of melamine resin by carrying out physical blending with flexible macromolecule；Chemical modification mainly by
Be added in melamine resin pre-polymerization process alcohols, urea, amide etc. can reaction molecular, improve water-soluble, reduce first
Aldehyde improves resin stability.But either physical modification or chemical modification, it always can not be by flexibility, resin
Stability accomplishes perfectly to balance.Physical blending toughening modifying does not improve the stability of resin, and chemical modification improves tree
The stability of rouge but have lost the excellent properties that surface of the paint film height is hard, wear-resisting.If carry out physics and chemical blend simultaneously, improve
Toughness but the wearability for reducing resin.So far, melamino-formaldehyde impregnating resin is easily between embrittlement and wearability
Equilibrium problem never obtain effective solution.
Summary of the invention
The technical problem to be solved by the present invention is to overcome the shortcomings of to mention in background above technology and defect, one kind is provided
The aqueous photo-curing modified melamine-formaldehyde impregnating resin and preparation method thereof for having high tenacity, stability, wearability.For solution
Certainly above-mentioned technical problem, technical solution proposed by the present invention are as follows:
A kind of aqueous photo-curing modified melamine-formaldehyde impregnating resin, includes the following components'mass percentage, water-soluble
Property melamine formaldehyde resin 70-90%, photocuring waterborne polyurethane resin 10-30%；Wherein, the water-soluble melamine
The raw material of amine-formaldehyde resin comprises the following components in parts by weight: 20-35 parts of melamine, 30-40 parts of 37wt.% formalin,
3-6 parts of modifying agent, 1.5-3.5 parts of caprolactam, 1.5-3.5 parts of acrylate co-monomers, 25-35 parts of water；The photocuring
The raw material of waterborne polyurethane resin comprises the following components in parts by weight: 8-15 parts of diisocyanate, 10-25 parts of polyalcohol, and dihydroxy
2-5 parts of methylpropanoic acid, 5-15 parts of monohydroxy acrylate, 0.05-0.15 parts of polymerization inhibitor, 0.01-0.08 parts of catalyst, neutralizer
2-4 parts, 50-65 parts of water.The effect of photocuring aqueous polyurethane is the stability and offer toughness of one side security system；Separately
On the one hand photocured cross-linked formation interpenetrating net polymer can be carried out with melamine formaldehyde resin.Photocuring aqueous polyurethane
Additional amount can excessively reduce hardness of paint film, and additional amount can make the stability of system that cannot ensure very little, control water-soluble trimerization
Cyanogen amine-formaldehyde resin and the proportionate relationship of photocuring waterborne polyurethane resin can balance the performance of resin within the above range.
In above-mentioned aqueous photo-curing modified melamine-formaldehyde impregnating resin, it is preferred that the modifying agent is diethylene glycol (DEG), four
One of glycol, polyethylene glycol and polyvinyl alcohol are a variety of.
In above-mentioned aqueous photo-curing modified melamine-formaldehyde impregnating resin, it is preferred that the acrylate co-monomers
For acrylamide, hydroxymethyl acrylamide, methacrylic acid ethylidene-urea ethoxylated ester and acrylic acid ethylidene-urea ethoxylated ester
One of or it is a variety of.Above-mentioned monomer has many advantages, such as that reactivity is high.Acrylate co-monomers main function is by altogether
It is poly- that the active group with photocuring is introduced into melamine resin, it is special with photocuring to assign melamine resin
Property；The crosslink density that will excessively reduce melamine is added, influences hardness, toughness, very few, the photocuring spy of melamine is added
Property is unobvious.
In above-mentioned aqueous photo-curing modified melamine-formaldehyde impregnating resin, it is preferred that the diisocyanate is toluene
Diisocyanate, isophorone diisocyanate, dicyclohexyl methyl hydride diisocyanate, cyclohexane diisocyanate and four methylenes
One of group diisocyanate is a variety of.
In above-mentioned aqueous photo-curing modified melamine-formaldehyde impregnating resin, it is preferred that the polyalcohol is polycaprolactone
Dihydric alcohol 1000, polycaprolactone diols 2000, polytetrahydrofuran dihydric alcohol 2000, polytetrahydrofuran dihydric alcohol 1000, poly- third
One of glycol 2000 and polypropylene glycol 1000 are a variety of.
In above-mentioned aqueous photo-curing modified melamine-formaldehyde impregnating resin, it is preferred that the polymerization inhibitor be hydroquinone,
One of p methoxy phenol, para hydroxybenzene ether and p-tert-Butylcatechol are a variety of.
In above-mentioned aqueous photo-curing modified melamine-formaldehyde impregnating resin, it is preferred that the catalyst be organotin and
One or both of organo-bismuth；The neutralizer is one of lithium hydroxide, triethanolamine and triethylamine or a variety of.It neutralizes
The alkalinity of agent influences greatly water solubility, and alkalinity can be such that by force very much photocuring aqueous polyurethane hydrolyzes and unstable, alkaline weak, melamine
The decline of polyimide resin stability.
As a general technical idea, the present invention also provides a kind of above-mentioned aqueous photo-curing modified melamine-formaldehydes
The preparation method of impregnating resin, comprising the following steps:
(1) by formaldehyde, water, modifying agent and melamine hybrid reaction, caprolactam, acrylate co-monomers are added
Reaction, obtains watersoluble melamine-formaldehyde resin；
(2) diisocyanate, polyalcohol, dihydromethyl propionic acid, catalyst are mixed, heating carries out prepolymerization, so
Monohydroxy acrylate, polymerization inhibitor end capping reaction are added afterwards, the water dispersion emulsification containing neutralizer is added after cooling, obtains photocuring
Waterborne polyurethane resin；
(3) by watersoluble melamine-formaldehyde resin, photocuring aqueous polyurethane obtained in step (1) and step (2)
Resin carries out physical blending conjunction, obtains the aqueous photo-curing modified melamine-formaldehyde impregnating resin.
Watersoluble melamine-formaldehyde resin structural formula obtained in step (1) is as follows:
Wherein, R1Indicate the glycol ether segment of modifying agent, R2Indicate acrylate co-monomers segment, R3It indicates in oneself
Amide segment.
In above-mentioned preparation method, it is preferred that in the step (1), formaldehyde, water, modifying agent and melamine are mixed anti-
At once, control reaction temperature is 90-95 DEG C, pH 8-9, reaction time 30-120min；Caprolactam, acrylate is added
When comonomer reacts, it is first cooled to 70-80 DEG C, then under conditions of pH is 9-9.5, it is total that caprolactam, acrylate is added
Polycondensation monomer reacts 60-120min.
In above-mentioned preparation method, it is preferred that in the step (2), when prepolymerization, control reaction temperature is 75-80
DEG C, reaction time 3-4h；When end capping reaction, the control reaction time is 80-85 DEG C, reaction time 3-4h；When dispersion and emulsion,
It is first cooled at 20-40 DEG C, dispersion and emulsion 1-1.5h.
It is in the present invention, step (1) and watersoluble melamine-formaldehyde resin obtained in step (2), photocuring is aqueous
When polyurethane resin carries out physical blending conjunction, the two will not react, when in use, can be solid by heat cure and radiation
Change mode is post-processed, and cross-linked network is formed, and assigns the good toughness of resin, hardness, wear-resisting in multiple modified mode
And stability.
Compared with the prior art, the advantages of the present invention are as follows:
1, aqueous photo-curing modified melamine-formaldehyde impregnating resin of the invention has good flexibility, stable storing
Property (can store 6 months at room temperature).Copolymer acrylate monomer is introduced into molecular backbone by chemical copolymerization modification, is assigning resin
Except photocuring activity, also reduction watersoluble melamine-formaldehyde resin initial stage crosslink density improves flexibility, and water-soluble
The physical blending of property melamine formaldehyde resin and photocuring waterborne polyurethane resin, can be improved the stability of system, when use
By the way that the toughness of resin can be improved after solidifying, resin is made still to obtain good stability, Er Qieke under the premise of keeping toughness
To improve the mobility of resin cured later.
2, in the present invention, watersoluble melamine-formaldehyde resin and photocuring waterborne polyurethane resin all have photocuring
Activity, therefore the aqueous photo-curing modified melamine-formaldehyde impregnating resin being finally prepared also has good radiation curing
Performance, after heat cure and radiation curing, watersoluble melamine-formaldehyde resin passes through with photocuring waterborne polyurethane resin
Multiple cross-linked formation cross-linked network makes the resin after solidifying have excellent surface hardness and wearability.
Specific embodiment
To facilitate the understanding of the present invention, present invention work more comprehensively, is meticulously described below in conjunction with preferred embodiment,
But the protection scope of the present invention is not limited to the following specific embodiments.
Unless otherwise defined, all technical terms used hereinafter and the normally understood meaning of those skilled in the art
It is identical.
Technical term used herein is intended merely to the purpose of description specific embodiment, is not intended to and limits this hair
Bright protection scope.
Unless otherwise specified, various raw material, reagent, the instrument and equipment etc. used in the present invention can pass through city
Field is commercially available or can be prepared by existing method.
Embodiment 1:
A kind of aqueous photo-curing modified melamine-formaldehyde impregnating resin, includes the following components'mass percentage, water-soluble
Property melamine formaldehyde resin 70%, photocuring waterborne polyurethane resin 30%.
Wherein, watersoluble melamine-formaldehyde resin raw material comprises the following components in parts by weight: 25 parts of melamine,
36 parts of 37wt.% formalin, 3 parts of polyethylene glycol, 3 parts of caprolactam, 2.5 parts of acrylamide, 35 parts of water.
The raw material of photocuring waterborne polyurethane resin comprises the following components in parts by weight: 10 parts of toluene di-isocyanate(TDI), gathering
200015 parts of caprolactone dihydric alcohol, 5 parts of dihydromethyl propionic acid, 8 parts of monohydroxy acrylate, 0.1 part of hydroquinone, organotin
0.1 part, 3 parts of triethanolamine, 50 parts of water.
The preparation method of above-mentioned aqueous photo-curing modified melamine-formaldehyde impregnating resin, comprising the following steps:
(1) by formaldehyde, water, polyethylene glycol and melamine hybrid reaction, controlling reaction temperature is 92 DEG C, pH 9, reaction
Time is 80min；70 DEG C are cooled to, then under conditions of pH is 9.5, caprolactam, acrylamide is added, 80min is reacted, obtains
To watersoluble melamine-formaldehyde resin；
(2) by toluene di-isocyanate(TDI), polycaprolactone diols 2000, dihydromethyl propionic acid, organotin mix, heat into
Row prepolymerization, control reaction temperature are 80 DEG C, reaction time 3.5h；Then monohydroxy acrylate is added, to benzene two
Phenol end capping reaction, control reaction time are 85 DEG C, reaction time 3.5h；The moisture containing triethanolamine is added after at 30 DEG C of cooling
Emulsification is dissipated, dispersion and emulsion 1h obtains photocuring waterborne polyurethane resin；
(3) by watersoluble melamine-formaldehyde resin, photocuring aqueous polyurethane obtained in step (1) and step (2)
Resin carries out physical blending conjunction, obtains above-mentioned aqueous photo-curing modified melamine-formaldehyde impregnating resin.
Embodiment 2:
A kind of aqueous photo-curing modified melamine-formaldehyde impregnating resin, includes the following components'mass percentage, water-soluble
Property melamine formaldehyde resin 88%, photocuring waterborne polyurethane resin 12%.
Wherein, watersoluble melamine-formaldehyde resin raw material comprises the following components in parts by weight: 33 parts of melamine,
30 parts of 37wt.% formalin, 6 parts of polyvinyl alcohol, 1.5 parts of caprolactam, methacrylic acid ethylidene-urea ethoxylated ester 1.8
Part, 30 parts of water.
The raw material of photocuring waterborne polyurethane resin comprises the following components in parts by weight: dicyclohexyl methyl hydride diisocyanate
15 parts, 100025 parts of polypropylene glycol, 5 parts of dihydromethyl propionic acid, 8 parts of monohydroxy acrylate, 0.12 part of p methoxy phenol, have
0.12 part of machine tin, 2.5 parts of triethanolamine, 65 parts of water.
The preparation method of above-mentioned aqueous photo-curing modified melamine-formaldehyde impregnating resin, comprising the following steps:
(1) by formaldehyde, water, polyvinyl alcohol and melamine hybrid reaction, controlling reaction temperature is 95 DEG C, pH 8.8, instead
It is 40min between seasonable；70 DEG C are cooled to, then under conditions of pH is 9.0, caprolactam, methacrylic acid ethylidene-urea is added
Ethoxylated ester reacts 65min, obtains watersoluble melamine-formaldehyde resin；
(2) dicyclohexyl methyl hydride diisocyanate, polypropylene glycol 1000, dihydromethyl propionic acid, organotin are mixed, heating
Prepolymerization is carried out, control reaction temperature is 78 DEG C, reaction time 3.0h；Then monohydroxy acrylate is added, to first
Oxygroup phenol end capping reaction, control reaction time are 80 DEG C, reaction time 3.0h；It is added after at 25 DEG C of cooling and contains triethanolamine
Water dispersion emulsification, dispersion and emulsion 1h obtains photocuring waterborne polyurethane resin；
(3) by watersoluble melamine-formaldehyde resin, photocuring aqueous polyurethane obtained in step (1) and step (2)
Resin carries out physical blending conjunction, obtains above-mentioned aqueous photo-curing modified melamine-formaldehyde impregnating resin.
Embodiment 3:
A kind of aqueous photo-curing modified melamine-formaldehyde impregnating resin, includes the following components'mass percentage, water-soluble
Property melamine formaldehyde resin 80%, photocuring waterborne polyurethane resin 20%.
Wherein, watersoluble melamine-formaldehyde resin raw material comprises the following components in parts by weight: 20 parts of melamine,
40 parts of 37wt.% formalin, 3 parts of tetraethylene glycol, 2 parts of caprolactam, 3 parts of acrylic acid ethylidene-urea ethoxylated ester, 22 parts of water.
The raw material of photocuring waterborne polyurethane resin comprises the following components in parts by weight: tetramethylene diisocyanate 12
Part, 100025 parts of polytetrahydrofuran dihydric alcohol, 5 parts of dihydromethyl propionic acid, 8 parts of monohydroxy acrylate, to tert-butyl o benzene two
0.1 part of phenol, 0.1 part of organo-bismuth, 2 parts of lithium hydroxide, 55 parts of water.
The preparation method of above-mentioned aqueous photo-curing modified melamine-formaldehyde impregnating resin, comprising the following steps:
(1) by formaldehyde, water, tetraethylene glycol and melamine hybrid reaction, controlling reaction temperature is 90 DEG C, pH 8, when reaction
Between be 120min；70 DEG C are cooled to, then under conditions of pH is 9.0, caprolactam, acrylic acid ethylidene-urea ethyoxyl is added
Ester reacts 100min, obtains watersoluble melamine-formaldehyde resin；
(2) tetramethylene diisocyanate, polytetrahydrofuran dihydric alcohol 1000, dihydromethyl propionic acid, organo-bismuth are mixed,
Heating carries out prepolymerization, and control reaction temperature is 78 DEG C, reaction time 4h；Then monohydroxy acrylate, right is added
Tert-butyl catechol end capping reaction, control reaction time are 80 DEG C, reaction time 4.0h；It is added after at 30 DEG C of cooling hydrogeneous
The water dispersion of lithia emulsifies, and dispersion and emulsion 1.5h obtains photocuring waterborne polyurethane resin；
(3) by watersoluble melamine-formaldehyde resin, photocuring aqueous polyurethane obtained in step (1) and step (2)
Resin carries out physical blending conjunction, obtains above-mentioned aqueous photo-curing modified melamine-formaldehyde impregnating resin.
Embodiment 4:
A kind of aqueous photo-curing modified melamine-formaldehyde impregnating resin, includes the following components'mass percentage, water-soluble
Property melamine formaldehyde resin 75%, photocuring waterborne polyurethane resin 25%.
Wherein, watersoluble melamine-formaldehyde resin raw material comprises the following components in parts by weight: 28 parts of melamine,
38 parts of 37wt.% formalin, 4.5 parts of diethylene glycol (DEG), 2 parts of caprolactam, 3 parts of acrylic acid ethylidene-urea ethoxylated ester, 25 parts of water.
The raw material of photocuring waterborne polyurethane resin comprises the following components in parts by weight: 9 parts of toluene di-isocyanate(TDI), gathering oneself
200012 parts of lactone dihydric alcohol, 4 parts of dihydromethyl propionic acid, 5 parts of monohydroxy acrylate, 0.05 part of p-tert-Butylcatechol,
0.05 part of organo-bismuth, 2 parts of lithium hydroxide, 58 parts of water.
The preparation method of above-mentioned aqueous photo-curing modified melamine-formaldehyde impregnating resin, comprising the following steps:
(1) by formaldehyde, water, diethylene glycol (DEG) and melamine hybrid reaction, controlling reaction temperature is 90 DEG C, pH 9, when reaction
Between be 100min；70 DEG C are cooled to, then under conditions of pH is 9.2, caprolactam, acrylic acid ethylidene-urea ethyoxyl is added
Ester reacts 80min, obtains watersoluble melamine-formaldehyde resin；
(2) by toluene di-isocyanate(TDI), polycaprolactone diols 2000, dihydromethyl propionic acid, organo-bismuth mix, heat into
Row prepolymerization, control reaction temperature are 75 DEG C, reaction time 3h；Then monohydroxy acrylate is added, to tert-butyl
Catechol end capping reaction, control reaction time are 82 DEG C, reaction time 3.5h；It is added after at 35 DEG C of cooling and contains lithium hydroxide
Water dispersion emulsification, dispersion and emulsion 1.5h obtains photocuring waterborne polyurethane resin；
(3) by watersoluble melamine-formaldehyde resin, photocuring aqueous polyurethane obtained in step (1) and step (2)
Resin carries out physical blending conjunction, obtains above-mentioned aqueous photo-curing modified melamine-formaldehyde impregnating resin.
After measured, the obtained aqueous photo-curing modified melamine-formaldehyde impregnating resin in embodiment 1-4 has excellent
The high combination properties such as stability, surface hardness and wearability, be with a wide range of applications.
The constituent of raw material is as shown in table 1 below in embodiment 1-4.
Table 1: the constituent of raw material in embodiment 1-4
Claims (10)
1. a kind of aqueous photo-curing modified melamine-formaldehyde impregnating resin, which is characterized in that including following mass percent
Component, watersoluble melamine-formaldehyde resin 70-90%, photocuring waterborne polyurethane resin 10-30%；Wherein, described water-soluble
The raw material of property melamine formaldehyde resin comprises the following components in parts by weight: 20-35 parts of melamine, 37wt.% formalin
30-40 parts, 3-6 parts of modifying agent, 1.5-3.5 parts of caprolactam, 1.5-3.5 parts of acrylate co-monomers, 25-35 parts of water；Institute
The raw material for stating photocuring waterborne polyurethane resin comprises the following components in parts by weight: 8-15 parts of diisocyanate, polyalcohol 10-25
Part, 2-5 parts of dihydromethyl propionic acid, 5-15 parts of monohydroxy acrylate, 0.05-0.15 parts of polymerization inhibitor, catalyst 0.01-0.08
Part, 2-4 parts of neutralizer, 50-65 parts of water.
2. aqueous photo-curing modified melamine-formaldehyde impregnating resin according to claim 1, which is characterized in that described to change
Property agent be one of diethylene glycol (DEG), tetraethylene glycol, polyethylene glycol and polyvinyl alcohol or a variety of.
3. aqueous photo-curing modified melamine-formaldehyde impregnating resin according to claim 1, which is characterized in that described third
Olefin(e) acid ester comonomer is that acrylamide, hydroxymethyl acrylamide, methacrylic acid ethylidene-urea ethoxylated ester and acrylic acid are sub-
One of ethyl carbamide ethoxylated ester is a variety of.
4. aqueous photo-curing modified melamine-formaldehyde impregnating resin according to any one of claim 1-3, feature
It is, the diisocyanate is toluene di-isocyanate(TDI), isophorone diisocyanate, dicyclohexyl methyl hydride diisocyanate
One of ester, cyclohexane diisocyanate and tetramethylene diisocyanate are a variety of.
5. aqueous photo-curing modified melamine-formaldehyde impregnating resin according to any one of claim 1-3, feature
Be, the polyalcohol be polycaprolactone diols 1000, polycaprolactone diols 2000, polytetrahydrofuran dihydric alcohol 2000,
One of polytetrahydrofuran dihydric alcohol 1000, polypropylene glycol 2000 and polypropylene glycol 1000 are a variety of.
6. aqueous photo-curing modified melamine-formaldehyde impregnating resin according to any one of claim 1-3, feature
It is, the polymerization inhibitor is one of hydroquinone, p methoxy phenol, para hydroxybenzene ether and p-tert-Butylcatechol
Or it is a variety of.
7. aqueous photo-curing modified melamine-formaldehyde impregnating resin according to any one of claim 1-3, feature
It is, the catalyst is one or both of organotin and organo-bismuth；The neutralizer be lithium hydroxide, triethanolamine and
One of triethylamine is a variety of.
8. a kind of preparation of such as aqueous photo-curing modified melamine-formaldehyde impregnating resin of any of claims 1-7
Method, which comprises the following steps:
(1) by formaldehyde, water, modifying agent and melamine hybrid reaction, it is anti-that caprolactam, acrylate co-monomers are added
It answers, obtains watersoluble melamine-formaldehyde resin；
(2) by diisocyanate, polyalcohol, dihydromethyl propionic acid, catalyst mix, heating carry out prepolymerization, then plus
Enter monohydroxy acrylate, polymerization inhibitor end capping reaction, the water dispersion emulsification containing neutralizer is added after cooling, it is aqueous to obtain photocuring
Polyurethane resin；
(3) by watersoluble melamine-formaldehyde resin, photocuring waterborne polyurethane resin obtained in step (1) and step (2)
Physical blending is carried out, the aqueous photo-curing modified melamine-formaldehyde impregnating resin is obtained.
9. preparation method according to claim 8, which is characterized in that in the step (1), by formaldehyde, water, modifying agent and
When melamine hybrid reaction, control reaction temperature is 90-95 DEG C, pH 8-9, reaction time 30-120min；It is added in oneself
When amide, acrylate co-monomers reaction, it is first cooled to 70-80 DEG C, then under conditions of pH is 9-9.5, acyl in oneself is added
Amine, acrylate co-monomers react 60-120min.
10. preparation method according to claim 8, which is characterized in that in the step (2), when prepolymerization, control
Reaction temperature is 75-80 DEG C, reaction time 3-4h；When end capping reaction, the control reaction time is 80-85 DEG C, and the reaction time is
3-4h；It when dispersion and emulsion, is first cooled at 20-40 DEG C, dispersion and emulsion 1-1.5h.
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Address after: 410600 lanyuegu Road, Ningxiang Economic and Technological Development Zone, Changsha City, Hunan Province Applicant after: Bonfurt new materials Co.,Ltd. Address before: 410600 Hunan province Changsha city after Ningxiang County Pu Xiang Jing Pu Cun (DA Wan Ling Industrial Park) Applicant before: HUNAN BANFERT NEW-MATERIALS TECHNOLOGY Co.,Ltd. |
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| GR01 | Patent grant | ||
| GR01 | Patent grant | ||
| TR01 | Transfer of patent right | ||
| TR01 | Transfer of patent right |
Effective date of registration: 20220531 Address after: 276714 intersection of Qingshi road and Xingda West Street, Linshu County, Linyi City, Shandong Province Patentee after: Bonfort (Shandong) new materials Co.,Ltd. Address before: 410600 lanyuegu Road, Ningxiang Economic and Technological Development Zone, Changsha City, Hunan Province Patentee before: Bonfurt new materials Co.,Ltd. |
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| PE01 | Entry into force of the registration of the contract for pledge of patent right | ||
| PE01 | Entry into force of the registration of the contract for pledge of patent right |
Denomination of invention: A waterborne photocurable modified melamine formaldehyde impregnation resin and its preparation method Granted publication date: 20210525 Pledgee: China Postal Savings Bank Co.,Ltd. Linshu County Branch Pledgor: Bonfort (Shandong) new materials Co.,Ltd. Registration number: Y2024980001701 |