JP7422761B2 - 揮発性有機化合物を実質的に含まず、高固形分を有する水性ポリウレタン分散体を調製する方法 - Google Patents
揮発性有機化合物を実質的に含まず、高固形分を有する水性ポリウレタン分散体を調製する方法 Download PDFInfo
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- JP7422761B2 JP7422761B2 JP2021525777A JP2021525777A JP7422761B2 JP 7422761 B2 JP7422761 B2 JP 7422761B2 JP 2021525777 A JP2021525777 A JP 2021525777A JP 2021525777 A JP2021525777 A JP 2021525777A JP 7422761 B2 JP7422761 B2 JP 7422761B2
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- diisocyanate
- component
- prepolymer
- isocyanate
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- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 claims description 3
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- SBJCUZQNHOLYMD-UHFFFAOYSA-N 1,5-Naphthalene diisocyanate Chemical compound C1=CC=C2C(N=C=O)=CC=CC2=C1N=C=O SBJCUZQNHOLYMD-UHFFFAOYSA-N 0.000 claims description 2
- LFSYUSUFCBOHGU-UHFFFAOYSA-N 1-isocyanato-2-[(4-isocyanatophenyl)methyl]benzene Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=CC=C1N=C=O LFSYUSUFCBOHGU-UHFFFAOYSA-N 0.000 claims description 2
- 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 claims description 2
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- 230000002194 synthesizing effect Effects 0.000 claims description 2
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical group CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 claims description 2
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 claims description 2
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- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
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- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 7
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 6
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- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 description 5
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- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N Tetraethylene glycol, Natural products OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 1
- ORLQHILJRHBSAY-UHFFFAOYSA-N [1-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1(CO)CCCCC1 ORLQHILJRHBSAY-UHFFFAOYSA-N 0.000 description 1
- SOGYZZRPOIMNHO-UHFFFAOYSA-N [2-(hydroxymethyl)furan-3-yl]methanol Chemical compound OCC=1C=COC=1CO SOGYZZRPOIMNHO-UHFFFAOYSA-N 0.000 description 1
- FDLQZKYLHJJBHD-UHFFFAOYSA-N [3-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=CC(CN)=C1 FDLQZKYLHJJBHD-UHFFFAOYSA-N 0.000 description 1
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 1
- 238000005299 abrasion Methods 0.000 description 1
- WDJHALXBUFZDSR-UHFFFAOYSA-M acetoacetate Chemical compound CC(=O)CC([O-])=O WDJHALXBUFZDSR-UHFFFAOYSA-M 0.000 description 1
- PFLUPZGCTVGDLV-UHFFFAOYSA-N acetone azine Chemical compound CC(C)=NN=C(C)C PFLUPZGCTVGDLV-UHFFFAOYSA-N 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 150000001299 aldehydes Chemical group 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 150000001414 amino alcohols Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- UTTHLMXOSUFZCQ-UHFFFAOYSA-N benzene-1,3-dicarbohydrazide Chemical compound NNC(=O)C1=CC=CC(C(=O)NN)=C1 UTTHLMXOSUFZCQ-UHFFFAOYSA-N 0.000 description 1
- WRUAHXANJKHFIL-UHFFFAOYSA-N benzene-1,3-disulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC(S(O)(=O)=O)=C1 WRUAHXANJKHFIL-UHFFFAOYSA-N 0.000 description 1
- QPKOBORKPHRBPS-UHFFFAOYSA-N bis(2-hydroxyethyl) terephthalate Chemical compound OCCOC(=O)C1=CC=C(C(=O)OCCO)C=C1 QPKOBORKPHRBPS-UHFFFAOYSA-N 0.000 description 1
- 229910052797 bismuth Inorganic materials 0.000 description 1
- OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical compound NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 150000001718 carbodiimides Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000008199 coating composition Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000006184 cosolvent Substances 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 description 1
- 235000018417 cysteine Nutrition 0.000 description 1
- 229960002887 deanol Drugs 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 239000012975 dibutyltin dilaurate Substances 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- 125000005442 diisocyanate group Chemical group 0.000 description 1
- 239000012972 dimethylethanolamine Substances 0.000 description 1
- 239000002612 dispersion medium Substances 0.000 description 1
- 239000004815 dispersion polymer Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 206010016256 fatigue Diseases 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 231100000869 headache Toxicity 0.000 description 1
- 125000005597 hydrazone group Chemical group 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 125000003010 ionic group Chemical group 0.000 description 1
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical group OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 239000006224 matting agent Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- RTWNYYOXLSILQN-UHFFFAOYSA-N methanediamine Chemical compound NCN RTWNYYOXLSILQN-UHFFFAOYSA-N 0.000 description 1
- 230000008693 nausea Effects 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 150000003139 primary aliphatic amines Chemical class 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- KCXFHTAICRTXLI-UHFFFAOYSA-N propane-1-sulfonic acid Chemical compound CCCS(O)(=O)=O KCXFHTAICRTXLI-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 1
- VHNQIURBCCNWDN-UHFFFAOYSA-N pyridine-2,6-diamine Chemical compound NC1=CC=CC(N)=N1 VHNQIURBCCNWDN-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 150000005619 secondary aliphatic amines Chemical class 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 150000008054 sulfonate salts Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical compound [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 0.000 description 1
- VOZKAJLKRJDJLL-UHFFFAOYSA-N tolylenediamine group Chemical group CC1=C(C=C(C=C1)N)N VOZKAJLKRJDJLL-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 1
- MBYLVOKEDDQJDY-UHFFFAOYSA-N tris(2-aminoethyl)amine Chemical compound NCCN(CCN)CCN MBYLVOKEDDQJDY-UHFFFAOYSA-N 0.000 description 1
- AVWRKZWQTYIKIY-UHFFFAOYSA-N urea-1-carboxylic acid Chemical compound NC(=O)NC(O)=O AVWRKZWQTYIKIY-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052726 zirconium Inorganic materials 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
- C08G18/28—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
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- 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
- C08G18/44—Polycarbonates
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- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/0804—Manufacture of polymers containing ionic or ionogenic groups
- C08G18/0819—Manufacture of polymers containing ionic or ionogenic groups containing anionic or anionogenic groups
- C08G18/0828—Manufacture of polymers containing ionic or ionogenic groups containing anionic or anionogenic groups containing sulfonate groups or groups forming them
-
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
- C08G18/12—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step using two or more compounds having active hydrogen in the first polymerisation step
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/34—Carboxylic acids; Esters thereof with monohydroxyl compounds
- C08G18/348—Hydroxycarboxylic acids
-
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- 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
- C08G18/4009—Two or more macromolecular compounds not provided for in one single group of groups C08G18/42 - C08G18/64
- C08G18/4018—Mixtures of compounds of group C08G18/42 with compounds of group C08G18/48
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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- 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
- C08G18/4202—Two or more polyesters of different physical or chemical nature
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- 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
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- 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
- C08G18/6625—Compounds of groups C08G18/42, C08G18/48, or C08G18/52 with compounds of group C08G18/34
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/65—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
- C08G18/66—Compounds of groups C08G18/42, C08G18/48, or C08G18/52
- C08G18/6666—Compounds of group C08G18/48 or C08G18/52
- C08G18/6692—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/34
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- 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
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/721—Two or more polyisocyanates not provided for in one single group C08G18/73 - C08G18/80
- C08G18/722—Combination of two or more aliphatic and/or cycloaliphatic polyisocyanates
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/73—Polyisocyanates or polyisothiocyanates acyclic
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- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
- C08G18/75—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic
- C08G18/751—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring
- C08G18/752—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group
- C08G18/753—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate group
- C08G18/755—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate group and at least one isocyanate or isothiocyanate group linked to a secondary carbon atom of the cycloaliphatic ring, e.g. isophorone diisocyanate
-
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- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/18—Manufacture of films or sheets
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- 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
- C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
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Description
i)アセトン又は他の溶媒の非存在下で、イソシアネート、親水基を有するポリオールを含んでもよいポリオール、ポリウレタンプレポリマー及び成分Aを含むプレポリマーを合成する工程であり、前記成分Aが、x個のヒドロキシ基及びy個のアミン基を有し(x及びyの両方が、それぞれ独立に0又は0超であることができ、x+y≧2である)、塩を形成できる追加の官能基を有する、工程と、
ii)得られたプレポリマーを水、アルカリ金属水酸化物等の1種又は複数の中和剤及び場合により乳化剤を含む水相に分散させ、ポリウレタンの分散体が少なくとも50質量パーセントの固形分を有し、アセトン又は他の溶媒を含有せず、250℃未満の沸点を有するアミン又は他の揮発性化合物を含有しないように、成分Bを含む1種又は複数の延長剤と反応させることによって、ポリウレタンを形成する工程であり、前記成分Bが、x個のヒドロキシ基及びy個のアミン基を有し(x及びyの両方が、それぞれ独立に0又は0超であることができ、x+y≧2である)、塩を形成できる追加の官能基を有する、工程と
を含む、方法を提供する。
物である。
ポリウレタン分散体の調製
窒素雰囲気下で、415gの分子量2000のポリ(テトラメチレンエーテル)グリコール、57gのヘキサンジオール由来の分子量1000のポリカーボネートジオール、及び4gのジメチロールプロパン酸の混合物を、撹拌しながら50℃に加熱した。70gの3-イソシアナトメチル-3,5,5-トリメチルシクロヘキシルイソシアネート及び25gのヘキサメチレンジイソシアネートを加え、混合物を85℃に加熱し、1.5時間攪拌してポリウレタンプレポリマーを形成した。反応物を冷却し、残留NCOの量を測定した。プレポリマーを、390gの水、15gのSynperonic PE/L62(Croda社製乳化剤)、1.2gの水酸化カリウム、及び13gのVestamin A95(Evonik社製2-[(2-アミノエチル)アミノ]エタンスルホン酸ナトリウムの溶液)からなる水相に分散させた。次いで、8gのヒドラジン水和物を加え、分散体を15分間攪拌した。分散体の固形分は、60%であった。分散体の粘度は、Brookfield LVF粘度計を使用して25℃で測定し、200mPa.sであった。
ポリウレタン分散体の調製
窒素雰囲気下で、205gの、ペンタンジオール及びヘキサンジオールに由来する分子量2000のポリカーボネートジオール、205gの、ヘキサンジオールに由来する分子量1000のポリカーボネートジオール、4gのジメチロールプロパン酸、及び14gのYmer-120(Perstorp社製直鎖状二官能ポリエチレングリコールモノメチルエーテル)の混合物を、攪拌しながら50℃に加熱した。115gの3-イソシアナトメチル-3,5,5-トリメチルシクロヘキシルイソシアネート及び30gのヘキサメチレンジイソシアネートを加え、混合物を85℃に加熱し、1.5時間攪拌してポリウレタンプレポリマーを形成した。反応物を冷却し、残留NCOの量を測定した。プレポリマーを、390gの水、15gのSynperonic PE/L62(Croda社製乳化剤)、1.8gの水酸化カリウム、6gのVestamin A95(Evonik社製2-[(2-アミノエチル)アミノ]エタンスルホン酸ナトリウムの溶液)、及び3gのヒドラジン水和物からなる水相に分散させた。次いで、13gのヒドラジン水和物を加え、分散体を15分間攪拌した。分散体の固形分は、60%であった。分散体の粘度は、Brookfield LVF粘度計を使用して25℃で測定し、200mPa.sであった。
ポリウレタン分散体の調製
窒素雰囲気下で、200gの、ペンタンジオール及びヘキサンジオールに由来する分子量2000のポリカーボネートジオール、200gの、ヘキサンジオールに由来する分子量1000のポリカーボネートジオール、4gのジメチロールプロパン酸、及び14gのYmer-120(Perstorp社製直鎖状二官能ポリエチレングリコールモノメチルエーテル)の混合物を、攪拌しながら50℃に加熱した。100gの3-イソシアナトメチル-3,5,5-トリメチルシクロヘキシルイソシアネート及び50gの2,2,4-トリメチルヘキサメチレンジイソシアネートを加えて、混合物を85℃に加熱し、1.5時間攪拌してポリウレタンプレポリマーを形成した。反応物を冷却して、残留NCOの量を測定した。プレポリマーを、390gの水、15gのSynperonic PE/L62(Croda社製乳化剤)、3.7gの水酸化カリウム、6gのVestaminA95(Evonik社製2-[(2-アミノエチル)アミノ]エタンスルホン酸ナトリウムの溶液)、及び3gのヒドラジン水和物からなる水相に分散させた。次いで、13gのヒドラジン水和物を加え、分散体を15分間攪拌した。分散体の固形分は、60%であった。分散体の粘度は、Brookfield LVF粘度計を使用して25℃で測定し、200mPa.sであった。
ポリウレタン分散体の耐溶剤性試験
実施例1~3の各分散体を、600μmの厚みのガラス板に塗布した。塗布された塗膜を伴うガラス板を室温で1日間乾燥し、次いで80℃にて8時間オーブンで乾燥した。乾燥した塗膜試料に、水、エタノール又はMEK(メチルエチルケトン又は2-ブタノン)を溶媒として、溶媒取り込み試験を施した。この試験で、乾燥し秤量された塗膜の断片を水、エタノール、又はMEKに1時間浸漬し、次いで塗膜の質量の増加を測定した。質量増加は、低い方がより良い。
VOCに対する分散体の試験
実施例1~3のポリウレタン分散体を、揮発性成分の存在に対して試験した。結果をTable 2(表2)に報告した。
Claims (17)
- 揮発性有機化合物を含まないポリウレタン分散体を調製する方法であって、
i)アセトンの非存在下で、イソシアネート、親水基を有するポリオールを含んでもよいポリオール及び成分Aから、ポリウレタンプレポリマーを合成する工程であり、前記成分Aが、x個のヒドロキシ基及びy個のアミン基を有し(x及びyの両方が、それぞれ独立に0又は0超であることができ、x+y≧2である)、塩を形成できる追加の官能基を有する、工程と、
ii)得られたプレポリマーを、他の添加剤を含む又は含まない水相に分散させる工程と、
(iii)プレポリマーを水中に分散させる前に、分散させるのと同時に、又は分散させた後に、1種又は複数の中和剤を加える工程と、
(iv)分散させる工程と同時に又はそれに続いて、ポリウレタンの分散体が少なくとも50質量パーセントの固形分を有するように、成分Bを含む1種又は複数の延長剤と反応させることによってポリウレタンを形成する工程であり、前記成分Bが、x個のヒドロキシ基及びy個のアミン基を有し(x及びyの両方が、それぞれ独立に0又は0超であることができ、x+y≧2である)、塩を形成できる追加の官能基を有する、工程と
を含む、方法。 - 前記1種又は複数の中和剤が、アルカリ金属水酸化物である、請求項1に記載の方法。
- 成分A及び/又は成分Bに存在する追加の官能基が、カルボキシレート基、スルホネート基及びホスフェート基からなる群から選択される、請求項1又は2に記載の方法。
- 成分Bが、1つ又は複数のアミノ基及び1つ又は複数のスルホネート基を含有する、請求項1から3のいずれか一項に記載の方法。
- 1つ又は複数のアミノ基及び1つ又は複数のスルホネート基を含有する、前記成分Bが、2-[(2-アミノエチル)アミノ]エタンスルホン酸ナトリウムである、請求項4に記載の方法。
- 成分Aが、カルボキシ含有ジオールである、請求項1から5のいずれか一項に記載の方法。
- イソシアネートが、脂肪族ジイソシアネート、芳香族ジイソシアネート、又は芳香族及び脂肪族ジイソシアネートの混合物である、請求項1から6のいずれか一項に記載の方法。
- 前記イソシアネートが、トルエン-2,4-ジイソシアネート、トルエン-2,6-ジイソシアネート及びそれらの混合物、ジフェニルメタン-4,4-ジイソシアネート、1,4-フェニレンジイソシアネート、ジシクロヘキシル-メタン-4,4'-ジイソシアネート、3-イソシアナトメチル-3,5,5-トリメチルシクロヘキシルイソシアネート、1,6-ヘキシルジイソシアネート、1,5-ペンチルジイソシアネート、1,3-ビス(イソシアナトメチル)シクロヘキサン、2,2,4-トリメチル-1,6-ジイソシアナトヘキサン(2,2,4-異性体、2,4,4-異性体若しくはそれらの混合物)、1,4-シクロヘキシルジイソシアネート、ノルボルニルジイソシアネート、p-キシレンジイソシアネート、2,4'-ジフェニルメタンジイソシアネート、並びに/又は1,5-ナフチレンジイソシアネートである、請求項7に記載の方法。
- ポリオールが、ポリエステルポリオール、ポリエステルアミドポリオール、ポリエーテルポリオール、ポリチオエーテルポリオール、ポリカーボネートポリオール、ポリアセタールポリオール、ポリオレフィンポリオール若しくはポリシロキサンポリオール、又はそれらの混合物、及び分子量500未満のジオール又はトリオールの群から選択される、請求項1から8のいずれか一項に記載の方法。
- 水性ポリウレタン分散体の固形分が、少なくとも55質量パーセントである、請求項1から9のいずれか一項に記載の方法。
- 前記水性ポリウレタン分散体の固形分が、少なくとも60質量パーセントである、請求項10に記載の方法。
- 成分Bの量が、プレポリマーの量中に存在するイソシアネート官能基に対して、0.05~0.50モル当量の成分Bに由来するイソシアネート反応性基が、加えられるような量であり、残留しているイソシアネート官能基が、他の延長剤によって延長され、用いられる延長剤の総量が、延長剤の総量中のイソシアネート反応性基のプレポリマー中のイソシアネート基に対する比が、0.7:1~2.0:1の範囲になるような量である、請求項1から11のいずれか一項に記載の方法。
- 前記他の延長剤が、ヒドラジン、エチレンジアミン、プロピレンジアミン、5-アミノ-1,3,3-トリメチル-シクロヘキサンメチル-アミン、又はアミン末端ポリエーテルである、請求項12に記載の方法。
- プレポリマーの総質量に基づいて計算した成分Aの量が、0.1~5質量パーセントの間である、請求項1から13のいずれか一項に記載の方法。
- 水性ポリウレタン分散体が、1000ppm未満の総VOC含有量を有する、請求項1から14のいずれか一項に記載の方法。
- 水性ポリウレタン分散体が、500ppm未満の総VOC含有量を有する、請求項15に記載の方法。
- 水性ポリウレタン分散体が、100ppm未満の総VOC含有量を有する、請求項15に記載の方法。
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