CN114773558A - High-solid printing resin for flexible material and preparation method thereof - Google Patents
High-solid printing resin for flexible material and preparation method thereof Download PDFInfo
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- CN114773558A CN114773558A CN202210462586.8A CN202210462586A CN114773558A CN 114773558 A CN114773558 A CN 114773558A CN 202210462586 A CN202210462586 A CN 202210462586A CN 114773558 A CN114773558 A CN 114773558A
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- 239000007787 solid Substances 0.000 title claims abstract description 82
- 229920005989 resin Polymers 0.000 title claims abstract description 65
- 239000011347 resin Substances 0.000 title claims abstract description 65
- 238000007639 printing Methods 0.000 title claims abstract description 58
- 239000000463 material Substances 0.000 title claims abstract description 37
- 238000002360 preparation method Methods 0.000 title description 7
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 32
- 229920005749 polyurethane resin Polymers 0.000 claims abstract description 27
- 239000003054 catalyst Substances 0.000 claims abstract description 21
- 229920005862 polyol Polymers 0.000 claims abstract description 21
- 150000003077 polyols Chemical class 0.000 claims abstract description 21
- 239000002904 solvent Substances 0.000 claims abstract description 19
- 125000005442 diisocyanate group Chemical group 0.000 claims abstract description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 11
- 150000004985 diamines Chemical class 0.000 claims abstract description 10
- 230000002194 synthesizing effect Effects 0.000 claims abstract description 6
- 238000000034 method Methods 0.000 claims description 13
- RNLHGQLZWXBQNY-UHFFFAOYSA-N 3-(aminomethyl)-3,5,5-trimethylcyclohexan-1-amine Chemical compound CC1(C)CC(N)CC(C)(CN)C1 RNLHGQLZWXBQNY-UHFFFAOYSA-N 0.000 claims description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical group CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 7
- 239000005058 Isophorone diisocyanate Substances 0.000 claims description 6
- -1 alcohol ethers Chemical class 0.000 claims description 6
- 238000001816 cooling Methods 0.000 claims description 6
- 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 6
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 4
- 229920001610 polycaprolactone Polymers 0.000 claims description 4
- 239000004632 polycaprolactone Substances 0.000 claims description 4
- 150000005846 sugar alcohols Polymers 0.000 claims description 4
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 3
- 230000003111 delayed effect Effects 0.000 claims description 3
- 150000002576 ketones Chemical class 0.000 claims description 3
- 229920000515 polycarbonate Polymers 0.000 claims description 3
- 239000004417 polycarbonate Substances 0.000 claims description 3
- 229920005906 polyester polyol Polymers 0.000 claims description 3
- 229920000570 polyether Polymers 0.000 claims description 3
- 239000013557 residual solvent Substances 0.000 claims description 3
- 150000001298 alcohols Chemical class 0.000 claims description 2
- 150000002009 diols Chemical class 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 10
- 238000012545 processing Methods 0.000 abstract description 9
- 238000006243 chemical reaction Methods 0.000 abstract description 6
- 229920002635 polyurethane Polymers 0.000 abstract description 5
- 239000004814 polyurethane Substances 0.000 abstract description 5
- 238000003854 Surface Print Methods 0.000 abstract description 3
- 238000010438 heat treatment Methods 0.000 abstract description 3
- 238000002156 mixing Methods 0.000 abstract description 3
- 230000002349 favourable effect Effects 0.000 abstract 1
- 239000000047 product Substances 0.000 description 39
- 238000001723 curing Methods 0.000 description 26
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 17
- 230000000052 comparative effect Effects 0.000 description 15
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 8
- 238000007646 gravure printing Methods 0.000 description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- 229920002614 Polyether block amide Polymers 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000006757 chemical reactions by type Methods 0.000 description 4
- VPRUMANMDWQMNF-UHFFFAOYSA-N phenylethane boronic acid Chemical compound OB(O)CCC1=CC=CC=C1 VPRUMANMDWQMNF-UHFFFAOYSA-N 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 239000011230 binding agent Substances 0.000 description 3
- 239000011256 inorganic filler Substances 0.000 description 3
- 239000012766 organic filler Substances 0.000 description 3
- 229920001187 thermosetting polymer Polymers 0.000 description 3
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 230000000903 blocking effect Effects 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 230000001627 detrimental effect Effects 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229910000000 metal hydroxide Inorganic materials 0.000 description 2
- 150000004692 metal hydroxides Chemical class 0.000 description 2
- 238000006452 multicomponent reaction Methods 0.000 description 2
- 238000011056 performance test Methods 0.000 description 2
- 238000012216 screening Methods 0.000 description 2
- 230000001235 sensitizing effect Effects 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 238000004383 yellowing Methods 0.000 description 2
- BJZYYSAMLOBSDY-QMMMGPOBSA-N (2s)-2-butoxybutan-1-ol Chemical compound CCCCO[C@@H](CC)CO BJZYYSAMLOBSDY-QMMMGPOBSA-N 0.000 description 1
- FKTHNVSLHLHISI-UHFFFAOYSA-N 1,2-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC=C1CN=C=O FKTHNVSLHLHISI-UHFFFAOYSA-N 0.000 description 1
- VEORPZCZECFIRK-UHFFFAOYSA-N 3,3',5,5'-tetrabromobisphenol A Chemical compound C=1C(Br)=C(O)C(Br)=CC=1C(C)(C)C1=CC(Br)=C(O)C(Br)=C1 VEORPZCZECFIRK-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 229920002396 Polyurea Polymers 0.000 description 1
- KXBFLNPZHXDQLV-UHFFFAOYSA-N [cyclohexyl(diisocyanato)methyl]cyclohexane Chemical compound C1CCCCC1C(N=C=O)(N=C=O)C1CCCCC1 KXBFLNPZHXDQLV-UHFFFAOYSA-N 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000008199 coating composition Substances 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- ZGFPVHRIZJQTOM-UHFFFAOYSA-N disodium diisocyanate Chemical compound [N-]=C=O.[N-]=C=O.[Na+].[Na+] ZGFPVHRIZJQTOM-UHFFFAOYSA-N 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- 229910003475 inorganic filler Inorganic materials 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000013008 moisture curing Methods 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000005056 polyisocyanate Substances 0.000 description 1
- 229920001228 polyisocyanate Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000036632 reaction speed Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 230000002226 simultaneous effect Effects 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical class CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- 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
- C08G18/08—Processes
- C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction 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
- C08G18/30—Low-molecular-weight compounds
- C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
- C08G18/3203—Polyhydroxy compounds
- C08G18/3206—Polyhydroxy compounds aliphatic
-
- 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
-
- 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
- C08G18/4236—Polycondensates having carboxylic or carbonic ester groups in the main chain containing only aliphatic groups
- C08G18/4238—Polycondensates having carboxylic or carbonic ester groups in the main chain containing only aliphatic groups derived from dicarboxylic acids and dialcohols
-
- 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
- C08G18/4804—Two or more polyethers of different physical or chemical nature
-
- 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
- C08G18/4833—Polyethers containing oxyethylene units
-
- 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
- C08G18/65—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
- C08G18/6633—Compounds of group C08G18/42
- C08G18/6637—Compounds of group C08G18/42 with compounds of group C08G18/32 or polyamines of C08G18/38
- C08G18/664—Compounds of group C08G18/42 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/3203
-
- 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
- C08G18/667—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38
- C08G18/6681—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/32 or C08G18/3271 and/or polyamines of C08G18/38
- C08G18/6685—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/32 or C08G18/3271 and/or polyamines of C08G18/38 with compounds of group C08G18/3225 or polyamines of C08G18/38
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- 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
- C09D11/00—Inks
- C09D11/02—Printing inks
- C09D11/10—Printing inks based on artificial resins
- C09D11/102—Printing inks based on artificial resins containing macromolecular compounds obtained by reactions other than those only involving unsaturated carbon-to-carbon bonds
Abstract
The invention provides a high-solid printing resin for a flexible material, which comprises the following components in parts by weight: 15-40 parts of polyol, 15-40 parts of diisocyanate, 0-20 parts of dihydric alcohol, 0-15 parts of diamine, 20-60 parts of solvent, 10-50 parts of enclosed curing agent and 0.01-3 parts of heat-sensitive catalyst. The high-solid printing resin for the flexible material utilizes polyurethane to provide elongation and soft hand feeling, and the closed curing agent can increase solid content and dry and comfortable surface, and is favorable for the characteristics of printing and processing; the high-solid printing resin meeting the performance is prepared by synthesizing polyurethane resin, mixing the polyurethane resin with a closed curing agent, printing, and heating to perform deblocking reaction on the curing agent. The high-solid printing resin for the flexible material is a mixture of polyurethane and an enclosed curing agent, has proper printing viscosity, is soft but not sticky, has high solid content, is suitable for surface printing of the flexible material, and has strong stereoscopic impression, soft hand feeling and stretchability.
Description
Technical Field
The invention relates to the technical field of high polymer materials, in particular to a high-solid printing resin for a flexible material and a preparation method thereof.
Background
A high-solid printing resin for gravure printing ink is used to impart a concave-convex feeling to the surface of a material to be processed. For this purpose, the resin materials used are firstly high in solids content and secondly low in processing viscosity. At present, most of the materials are single-component or multi-component reaction type resins, which have long reaction time, high crosslinking density after curing and low elongation, so that the materials cannot adapt to flexible materials, and especially cannot be applied to flexible materials needing stretching or folding.
Since most of the high-solid printing resins are of a two-component reaction type, such as a moisture curing reaction type or a light curing reaction type, patents and documents of a one-component reaction type are rarely reported, and a soft one-component high-solid printing resin is less common.
In chinese patent publication No. CN100572509C, lubulizol, ohio, usa, a high solids dispersion is disclosed, wherein a dispersion composition comprises (a) a metal base selected from the group consisting of (i) a metal hydroxide having a solids content greater than about 51% by weight of the composition, (ii) a metal base other than a metal hydroxide having a solids content greater than about 15% by weight of the composition, and (iii) mixtures thereof; (b) a surfactant; and (c) an organic medium having a water content of less than about 2 wt%. The method for preparing the composition and the method for applying the composition are also provided, wherein the solid content is increased by inorganic substances, and the film formation cannot be supposed to be realized and a certain elongation is realized.
Passion coatings, Inc. also discloses high solids coatings and methods of application, and in particular, a high solids coating composition having excellent rheological properties and appearance, comprising (a) a thermosetting binder, (b) from about 0.1 to 10 wt%, based on binder solids, of solid polyurea particles, prepared by reacting a polyisocyanate with a mixture of amino reactants comprising a primary or secondary monoamine which optionally has a hydroxyl or ether group or both, and (c) about 5 to 20 wt% cellulose mixed ester based on binder solids, having a number average molecular weight of about 1000-, therefore, the method discloses a multi-component reaction type thermosetting material which has complex ingredients during processing, low stretching length of a thermosetting product and can not apply flexibility and materials.
Polyurethane is a resin which can be designed to have high softness, and can be applied to surface printing of flexible materials, but the application of high-solid printing (gravure printing) has some problems: firstly, a film can be formed and the surface is not sticky until a certain molecular weight is reached, but the viscosity is increased along with the increase of the molecular weight, and the too high viscosity cannot be applied to gravure printing; if the viscosity is reduced by adding a solvent for dilution, the solid content is reduced, and the original surface of a high-solid product cannot be provided with concave-convex feeling; if a polyurethane resin with high solid content and low viscosity is directly synthesized, the molecular weight is too low, and film formation and surface stickiness are affected due to the low molecular weight.
Disclosure of Invention
In order to solve the problems in the prior art, the invention provides a high-solid printing resin for a flexible material, which is a single-component non-reactive high-solid printing resin (gravure printing ink), has the characteristics of high solid content, proper viscosity, high elongation and soft hand feeling, can be applied to the surface of the flexible material, does not shrink or diffuse after high-solid printing (gravure printing), can keep clear patterns and strong stereoscopic impression, and has the performances of stretching, soft and non-stick surface and the like.
In order to achieve the purpose, the invention provides the following technical scheme:
the high-solid printing resin for the flexible material comprises the following components in parts by weight:
15-40 parts of a polyhydric alcohol,
15-40 parts of diisocyanate, namely,
0-20 parts of dihydric alcohol,
0-15 parts of diamine, namely, urea,
20-60 parts of a solvent, namely,
10-50 parts of a closed curing agent,
0.01-3 parts of heat-sensitive catalyst.
The high-solid printing resin for the flexible material utilizes polyurethane to provide elongation and soft hand feeling, and the closed curing agent can increase solid content, ensure dryness and is beneficial to the characteristics of printing and processing; the high-solid printing resin meeting the performance is prepared by synthesizing polyurethane resin, mixing the polyurethane resin with a closed curing agent, printing, and heating to perform deblocking reaction on the curing agent.
The high-solid printing resin for the flexible material is a mixture of polyurethane and an enclosed curing agent, has proper printing viscosity, is soft but not sticky, has high solid content, is suitable for surface printing of the flexible material, and has strong stereoscopic impression, soft handfeel and stretchability.
As a further description of the technical solution of the present invention, the polyol is at least one of polyester polyol, polyether polyol, polycaprolactone polyol or polycarbonate polyol.
As a further description of the technical scheme of the invention, the polyol is difunctional and has a molecular weight of 1000-3000.
As a further description of the technical solution of the present invention, the diisocyanate comprises at least one of TDI, MDI, H12MDI, IPDI or XDI.
As a further description of the technical scheme of the invention, the dihydric alcohol is at least one of EGO, BDO or HDO.
As further description of the technical scheme of the invention, the diamine is one or two of EDA or IPDA.
As further description of the technical scheme of the invention, the solvent is DMF, ketones, esters, aromatic hydrocarbons, alcohols or alcohol ethers.
As further description of the technical scheme of the invention, the deblocking temperature of the blocked curing agent is 80-160 ℃; the heat-sensitive catalyst is a heat-sensitive delayed catalyst of Deyin company and is DY-5508.
The invention also provides a preparation method of the high-solid printing resin for the flexible material, which comprises the following steps:
s1, synthesizing polyurethane resin; according to the weight portion, taking polyol, diisocyanate and a part of solvent, and enabling the polyol and the diisocyanate to react to form a prepolymer;
s2, adding dihydric alcohol or diamine for chain extension to synthesize polyurethane resin, so that the polyurethane resin reaches the target molecular weight and has basic film forming conditions;
s3, cooling, and adding a closed curing agent;
and S4, adding the residual solvent and the thermosensitive catalyst to prepare a high-solid printing resin finished product.
In the preparation method, the prepolymer is prepared first, and then the polyurethane resin is synthesized by chain expansion, so that the polyurethane resin reaches a certain molecular weight and basic film forming conditions. Because the polyurethane resin with good film-forming property has higher viscosity or lower solid content, the viscosity and the solid content need to be strictly controlled in the synthesis process.
Then, adding a closed curing agent at the later reaction stage of the polyurethane resin, wherein the addition of the closed curing agent has little improvement on viscosity, but effectively improves the solid content; meanwhile, the blocked curing agent is deblocked when being heated, and the released NCO group reacts with the residual hydroxyl of the polyurethane resin, so that the anti-sticking performance of the product is improved; the addition of the thermosensitive catalyst can accelerate the reaction speed and ensure the stability of the product at normal temperature.
While many inorganic or organic fillers increase solids, the simultaneous effect is either a decrease in elongation or an increase in viscosity, or both, which are detrimental to high solids printing processes and maintain softness. Through screening, the blocked curing agent used by the invention has little influence on viscosity when the solid content of the polyurethane resin is improved, and the blocked NCO group is contained, so that the blocked curing agent can be deblocked when being heated, and the released NCO group reacts with residual hydroxyl of the polyurethane resin, thereby improving the anti-sticking performance of the product.
Further, the solid content of the high-solid printing resin finished product is more than or equal to 40%, the viscosity range is 3000-10000 mPa.S/25 ℃, and the elongation is more than or equal to 200%.
The surface of the high-solid printing resin finished product is not sticky, and the surface opposite sticking test shows that: pressing 2Kg of weight on the surface of 5cm × 5cm, and facing the surface of the paste to be non-sticky and easy to separate after 50 ℃ for 4 hours without affecting the surface effect.
The finished product of the high-solid printing resin is a single-component product and is dried at the temperature of 100-150 ℃.
Based on the technical scheme, compared with the prior art, the invention has the following advantages and beneficial effects:
(1) the high-solid printing resin for the flexible material has the characteristic of high solid content, and the surface of a processed product has strong stereoscopic impression; has proper low viscosity, can meet the requirement of a gravure printing process, has high elongation and meets the requirement of flexible material performance.
(2) The high-solid printing resin is single-component high-solid printing resin (gravure processing printing ink), is simple in ingredients, free of reaction and short in processing time; the pattern is fine without deformation, keeps clear patterns and strong stereoscopic impression, and can be applied to micro-carving anti-counterfeiting printing of paper and films. The solvent is adjustable, and can be converted into an environment-friendly solvent or even an aqueous product from the traditional solvent containing non-environment-friendly aromatic hydrocarbons.
Detailed Description
In order that the invention may be more fully understood, reference will now be made to the specific embodiments illustrated. The invention provides a preferred embodiment. This invention may, however, be embodied in many different forms and should not be construed as limited to the embodiments set forth herein. Rather, these embodiments are provided so that this disclosure will be thorough and complete.
Unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs. The terminology used herein in the description of the invention is for the purpose of describing particular embodiments only and is not intended to be limiting of the invention.
The high-solid printing resin for the flexible material comprises the following components in parts by weight:
15-40 parts of a polyhydric alcohol,
15-40 parts of diisocyanate, namely, sodium diisocyanate,
0-20 parts of dihydric alcohol,
0-15 parts of diamine, namely, urea,
20-60 parts of a solvent, namely,
10-50 parts of a closed curing agent,
0.01-3 parts of heat-sensitive catalyst.
Wherein the polyol is at least one of polyester polyol, polyether polyol, polycaprolactone polyol or polycarbonate polyol.
Wherein the polyhydric alcohol is difunctional and has a molecular weight of 1000-3000.
Wherein the diisocyanate comprises TDI, MDI and H12At least one of MDI, IPDI or XDI.
TDI: toluene diisocyanate, which has two isomers of 2, 4-toluene diisocyanate and 2, 6-toluene diisocyanate;
MDI: diphenylmethane diisocyanate;
H12MDI: dicyclohexylmethane diisocyanate;
IPDI: isophorone diisocyanate;
XDI: xylylene diisocyanate;
wherein the dihydric alcohol is at least one of EGO, BDO or HDO.
EGO: ethylene glycol;
BDO: 1, 4-butanediol;
HDO: 1, 6-hexanediol.
Wherein, the diamine is one or two of EDA or IPDA.
EDA: ethylene diamine;
IPDA: isophorone diamine;
wherein the solvent is DMF, ketone, ester, aromatic hydrocarbon, alcohol or alcohol ether solvent.
Wherein the deblocking temperature of the blocked curing agent is 80-160 ℃; the heat-sensitive catalyst is a heat-sensitive delayed catalyst of Deyin company and is in a model number DY-5508.
The high-solid printing resin for the flexible material is prepared by the following preparation method, and specifically comprises the following steps:
s1, synthesizing polyurethane resin; according to the weight portion, taking polyol, diisocyanate and a part of solvent, and enabling the polyol and the diisocyanate to react to form a prepolymer;
s2, adding dihydric alcohol or diamine for chain extension to synthesize polyurethane resin, so that the polyurethane resin reaches the target molecular weight and has basic film forming conditions;
s3, cooling, and adding a closed curing agent;
and S4, adding the residual solvent and the thermosensitive catalyst to prepare a high-solid printing resin finished product.
When synthesizing polyurethane resin, certain molecular weight and basic film forming conditions need to be achieved; because the polyurethane resin with good film-forming property has higher viscosity or lower solid content, the viscosity and solid content need to be strictly controlled in the synthesis process.
Adding the closed curing agent at the later reaction stage of the polyurethane resin, wherein the addition of the closed curing agent does not greatly improve the viscosity, but effectively improves the solid content; and the polyurethane resin contains blocked NCO groups, can be deblocked when heated, and the released NCO groups react with residual hydroxyl of the polyurethane resin, so that the anti-sticking performance of the product is improved.
While many inorganic or organic fillers can increase solids content, they can also have the effect of either decreasing elongation or increasing viscosity, or both, which can be detrimental to high solids printing processes and maintain softness.
Through screening, the blocked curing agent contains blocked NCO groups while improving the solid content, can be unblocked when heated, and has the characteristics of reaction of the released NCO groups and residual hydroxyl groups of polyurethane resin, improvement of the anti-sticking performance of products and the like.
The solid content of the high-solid printing resin finished product prepared by the method is more than or equal to 40 percent, the viscosity range is 3000-10000 mPa.S/25 ℃, and the elongation is more than or equal to 200 percent.
Example 1
TOL250g, PEBA 2000200 g and TDI 175.8g are taken to react for 2 hours at 80 ℃ to obtain NCO prepolymer; to this prepolymer, 45g of BDO was slowly added until the viscosity rose to 30000mpa.s/75 ℃ which consumed about 50-80% of the BDO; after the viscosity reached the standard, 1.5 times of the remaining BDO amount is added in one time to ensure that NCO is consumed.
And (3) cooling to below 50 ℃, adding a blocked TDI curing agent BL 1100100 g to completely disperse, and then heating 5g of a photosensitive catalyst and a terminal solvent MEK150g to obtain a high-solid printing resin finished product, wherein NV: 57 percent; and (5) VIS: 8000mpa.s/25 ℃. The resin has low cost, does not absorb water, can be used for screen printing besides gravure printing, and has the processing temperature of 140 ℃.
Example 2
Taking 250g of PMA, 2000100 g g of PPG, 100050 g g of PTMG and 100g of IPDI, reacting for 3 hours at 90 ℃ to obtain a prepolymer with NCO content of 1.4mmol/g, cooling to 50 ℃, slowly dropping 59.6g of IPDA to extend the chain until the viscosity reaches 30000mpa.s/50 ℃, stopping with excessive IPDA, adding 80X 100g of blocked curing agent TPA-B, adding 8g of thermal sensitive catalyst, and uniformly mixing to obtain a high-solid printing resin finished product, wherein NV: 60 percent; VIS: 5000mpa.s/25 ℃. The resin product is yellowing-resistant environment-friendly high-solid printing resin, and has proper viscosity, good processability and processing temperature of 110-.
Example 3
Taking 350g of DMF, 1000200 g g of PBA and 31g of EG, adding 175g of MDI step by step, polymerizing until the viscosity rises to 30000pa.s/75 ℃, cooling to below 50 ℃, adding a closed curing agent BL 1100150 g, dispersing uniformly, and adding 5g of a thermal catalyst and MEK150g to obtain a high-solid printing resin finished product, wherein NV: 53 percent; VIS: 9000mpa.s/25 ℃. The resin product is MDI type, has good film forming property and stable pattern, can be applied to micro-engraving high-solid printing, and has the processing temperature of 140 ℃.
Example 4
Taking 350g of DMF, 1000200 g of polycaprolactone and 31g of EG, and adding H step by step12182g MDI is polymerized until the viscosity is increased to 20000pa.s/75 ℃, the temperature is reduced below 50 ℃, a closed curing agent TPA-B80X 200g is added, the mixture is stirred evenly, and 8g of thermal catalyst and MEK150g are added to obtain a finished product of the high-solid printing resin, wherein, NV: 52 percent; and (5) VIS: the product has good film forming property, yellowing resistance and weather resistance, and is suitable for outdoor and other occasions with high requirements at 8000mpa.s/25 ℃.
Comparative example 5
The resin product was prepared as in example 1 except that the prepolymer was prepared at a viscosity of 5500mpa.s/75 ℃ to give a final resin product having a VIS: 2500mpa.s/25 ℃.
Comparative example 6
The procedure for the preparation of the resin product was the same as in example 1 except that the prepolymer was prepared while controlling the viscosity at 30000mpa.s/75 ℃ to obtain a resin product whose VIS: 9500mpa.s/25 ℃.
Comparative example 7
The resin product was prepared as in example 1 except that the prepolymer was prepared while controlling the viscosity to 55000mpa.s/75 ℃ to obtain a resin product whose VIS: 33000mpa.s/25 ℃.
The resin products of examples 1 to 4, and comparative examples 5 to 7 were tested, and the test results are shown in tables 1 and 2.
TABLE 1 results of the resin product Performance test of examples 1 to 4
TABLE 2 results of the property test of the resin products of comparative examples 5 to 7
Surface to surface adhesion test: a2 Kg weight was pressed on a 5cm X5 cm surface, and the plates were faced to each other at 50 ℃ for 4 hours.
Comparative example 1
TOL250g, PEBA 2000200 g and TDI 175.8g are taken to react for 2 hours at 80 ℃ to obtain NCO prepolymer; to this prepolymer, 45g of BDO was slowly added until the viscosity rose to 10000mpa.s/75 ℃ consuming about 50-80% of BDO; after the viscosity reached the standard, 1.5 times of the remaining BDO amount is added in one time to ensure that NCO is consumed.
The temperature is reduced to below 50 ℃, 100g of chlorinated polypropylene is added to be completely dispersed, and then 5g of a thermosensitive catalyst and a terminal solvent MEK150g are heated to obtain a resin finished product of comparative example 1.
Comparative example 2
TOL250g, PEBA 2000200 g and TDI 175.8g are taken to react for 2 hours at 80 ℃ to obtain NCO prepolymer; to this prepolymer, 45g of BDO was slowly added until the viscosity rose to 10000mpa.s/75 ℃ consuming about 50-80% of BDO; after the viscosity reached the standard, 1.5 times of the remaining BDO amount was added in one time to consume the NCO.
The temperature is reduced to below 50 ℃, 100g of silicon dioxide is added to be completely dispersed, and then 5g of a sensitizing catalyst and a terminal solvent MEK150g are heated to obtain a resin finished product of comparative example 2.
Comparative example 3
TOL250g, PEBA 2000200 g and TDI 175.8g are taken to react for 2 hours at 80 ℃ to obtain NCO prepolymer; to this prepolymer, 45g of BDO was slowly added until the viscosity rose to 10000mpa.s/75 ℃ consuming about 50-80% of BDO; after the viscosity reached the standard, 1.5 times of the remaining BDO amount is added in one time to ensure that NCO is consumed.
The temperature is reduced to below 50 ℃, 100g of calcium carbonate is added to be completely dispersed, and then 5g of a sensitizing catalyst and a terminal solvent MEK150g are heated to obtain a resin finished product of comparative example 3.
The finished resin products of example 1 and comparative examples 1 to 3 were tested, and the test results are shown in Table 3.
TABLE 3 results of performance test of the resin products of example 1, comparative example 1 to comparative example 3
In the above comparative examples, different organic or inorganic fillers were added to increase the solid content, and it is obvious that either filler added could not be compared with the product added with the blocking curing agent, so the product added with the blocking curing agent was the most excellent product in combination.
The foregoing is illustrative and explanatory only, and is not to be construed as limiting the scope of the invention, which is defined by the appended claims. It should be noted that, for a person skilled in the art, several variations and modifications are possible without departing from the inventive concept, and such obvious alternatives fall within the scope of the invention.
Claims (10)
1. The high-solid printing resin for the flexible material is characterized by comprising the following components in parts by weight:
15-40 parts of a polyhydric alcohol,
15-40 parts of diisocyanate, namely,
0-20 parts of dihydric alcohol,
0-15 parts of diamine, namely,
20-60 parts of a solvent, namely,
10-50 parts of a closed curing agent,
0.01-3 parts of a thermosensitive catalyst.
2. The high-solid printing resin for flexible material as claimed in claim 1, wherein said polyol is at least one of polyester polyol, polyether polyol, polycaprolactone polyol and polycarbonate polyol.
3. The high-solid printing resin for flexible material as claimed in claim 2, wherein the polyol has a difunctional group and has a molecular weight of 1000-3000.
4. The high solids printing resin for flexible materials of claim 1 wherein the diisocyanate comprises TDI, MDI, H12At least one of MDI, IPDI or XDI.
5. The high-solid printing resin for flexible materials as claimed in claim 1, wherein the diol is at least one of EGO, BDO or HDO.
6. The high-solid printing resin for flexible materials as claimed in claim 1, wherein the diamine is one or both of EDA and IPDA.
7. The high-solid printing resin for flexible materials as claimed in claim 1, wherein the solvent is DMF, ketones, esters, aromatic hydrocarbons, alcohols or alcohol ethers.
8. The high-solid printing resin for flexible materials as claimed in claim 1, wherein the deblocking temperature of the blocked curing agent is 80-160 ℃; the thermosensitive catalyst is a thermosensitive delayed catalyst of Debo company and is DY-5508.
9. A method for preparing the high-solid printing resin for the flexible material according to any one of claims 1 to 8, comprising the steps of:
s1, synthesizing polyurethane resin; taking polyol, diisocyanate and part of solvent according to parts by weight, and enabling the polyol and the diisocyanate to react to form a prepolymer;
s2, adding dihydric alcohol or diamine for chain extension to synthesize polyurethane resin, so that the polyurethane resin reaches the target molecular weight and has basic film forming conditions;
s3, cooling, and adding a closed curing agent;
and S4, adding the residual solvent and the thermosensitive catalyst to prepare a high-solid printing resin finished product.
10. The method for preparing high-solid printing resin for flexible material as claimed in claim 9, wherein the solid content of the final high-solid printing resin is not less than 40%, the viscosity is 3000-10000 mPa-S/25 ℃, and the elongation is not less than 200%.
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| WO2021110087A1 (en) * | 2019-12-05 | 2021-06-10 | 广东盈通新材料有限公司 | Latent mono-component polyurethane hot melt glue, preparation method therefor and glue film |
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| CN101781453A (en) * | 2010-02-22 | 2010-07-21 | 北京高盟化工有限公司 | Method for preparing resin for latently-curable polyurethane ink |
| CN106554476A (en) * | 2016-07-15 | 2017-04-05 | 新东方油墨有限公司 | A kind of preparation method of the polyurethane resin for flexible package intaglio plate table printing ink |
| CN107383331A (en) * | 2017-08-21 | 2017-11-24 | 合肥安利聚氨酯新材料有限公司 | A kind of grease proofness isolation-type wet method polyurethane resin and preparation method thereof |
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