CN105440238A - 适合作为分散剂或防沉降剂的加合化合物 - Google Patents
适合作为分散剂或防沉降剂的加合化合物 Download PDFInfo
- Publication number
- CN105440238A CN105440238A CN201510680950.8A CN201510680950A CN105440238A CN 105440238 A CN105440238 A CN 105440238A CN 201510680950 A CN201510680950 A CN 201510680950A CN 105440238 A CN105440238 A CN 105440238A
- Authority
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- China
- Prior art keywords
- component
- addition compound
- compound
- addition
- isocyanate
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 80
- 239000003795 chemical substances by application Substances 0.000 title claims abstract description 39
- 238000004062 sedimentation Methods 0.000 title claims abstract description 13
- 239000002270 dispersing agent Substances 0.000 title abstract description 9
- 239000000049 pigment Substances 0.000 claims abstract description 25
- 239000005056 polyisocyanate Substances 0.000 claims abstract description 23
- 229920001228 polyisocyanate Polymers 0.000 claims abstract description 23
- 239000006224 matting agent Substances 0.000 claims abstract description 22
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims abstract description 13
- 239000000945 filler Substances 0.000 claims abstract description 10
- 229920000642 polymer Polymers 0.000 claims abstract description 8
- 239000006185 dispersion Substances 0.000 claims description 34
- 238000006243 chemical reaction Methods 0.000 claims description 24
- -1 amino, hydroxyl Chemical group 0.000 claims description 23
- 239000000203 mixture Substances 0.000 claims description 21
- 229920000728 polyester Polymers 0.000 claims description 17
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 claims description 16
- 239000005057 Hexamethylene diisocyanate Substances 0.000 claims description 13
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 claims description 13
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 claims description 12
- GZVHEAJQGPRDLQ-UHFFFAOYSA-N 6-phenyl-1,3,5-triazine-2,4-diamine Chemical compound NC1=NC(N)=NC(C=2C=CC=CC=2)=N1 GZVHEAJQGPRDLQ-UHFFFAOYSA-N 0.000 claims description 11
- 229920000570 polyether Polymers 0.000 claims description 11
- 238000002360 preparation method Methods 0.000 claims description 11
- 150000002148 esters Chemical class 0.000 claims description 9
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
- JIABEENURMZTTI-UHFFFAOYSA-N 1-isocyanato-2-[(2-isocyanatophenyl)methyl]benzene Chemical class O=C=NC1=CC=CC=C1CC1=CC=CC=C1N=C=O JIABEENURMZTTI-UHFFFAOYSA-N 0.000 claims description 7
- IMUDHTPIFIBORV-UHFFFAOYSA-N aminoethylpiperazine Chemical compound NCCN1CCNCC1 IMUDHTPIFIBORV-UHFFFAOYSA-N 0.000 claims description 7
- KDHWOCLBMVSZPG-UHFFFAOYSA-N 3-imidazol-1-ylpropan-1-amine Chemical class NCCCN1C=CN=C1 KDHWOCLBMVSZPG-UHFFFAOYSA-N 0.000 claims description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000001118 alkylidene group Chemical group 0.000 claims description 5
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 claims description 5
- WSGYTJNNHPZFKR-UHFFFAOYSA-N 3-hydroxypropanenitrile Chemical compound OCCC#N WSGYTJNNHPZFKR-UHFFFAOYSA-N 0.000 claims description 4
- 229920000098 polyolefin Polymers 0.000 claims description 4
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- KHUFHLFHOQVFGB-UHFFFAOYSA-N 1-aminoanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2N KHUFHLFHOQVFGB-UHFFFAOYSA-N 0.000 claims description 2
- FSWLUYQMFPBXSH-UHFFFAOYSA-N 2,4,7,9-tetramethyldec-5-yne-1,1-diol Chemical compound CC(C)CC(C)C#CC(C)CC(C)C(O)O FSWLUYQMFPBXSH-UHFFFAOYSA-N 0.000 claims description 2
- QPQKUYVSJWQSDY-CCEZHUSRSA-N 4-(phenylazo)aniline Chemical compound C1=CC(N)=CC=C1\N=N\C1=CC=CC=C1 QPQKUYVSJWQSDY-CCEZHUSRSA-N 0.000 claims description 2
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 claims description 2
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000002769 thiazolinyl group Chemical group 0.000 claims description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract description 12
- 229910052757 nitrogen Inorganic materials 0.000 abstract description 6
- 238000000576 coating method Methods 0.000 description 21
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
- 239000011248 coating agent Substances 0.000 description 18
- 239000007787 solid Substances 0.000 description 12
- 239000000126 substance Substances 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 8
- 239000003973 paint Substances 0.000 description 8
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 7
- 229940043232 butyl acetate Drugs 0.000 description 7
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 7
- QOSMNYMQXIVWKY-UHFFFAOYSA-N Propyl levulinate Chemical compound CCCOC(=O)CCC(C)=O QOSMNYMQXIVWKY-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 239000008186 active pharmaceutical agent Substances 0.000 description 5
- 238000005227 gel permeation chromatography Methods 0.000 description 5
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 4
- 239000005058 Isophorone diisocyanate Substances 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000008199 coating composition Substances 0.000 description 4
- 238000004040 coloring Methods 0.000 description 4
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 239000002609 medium Substances 0.000 description 4
- 239000004814 polyurethane Substances 0.000 description 4
- 229920002635 polyurethane Polymers 0.000 description 4
- DQFBYFPFKXHELB-UHFFFAOYSA-N Chalcone Natural products C=1C=CC=CC=1C(=O)C=CC1=CC=CC=C1 DQFBYFPFKXHELB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 3
- 235000005513 chalcones Nutrition 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 239000012948 isocyanate Substances 0.000 description 3
- 229960002725 isoflurane Drugs 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 229960001866 silicon dioxide Drugs 0.000 description 3
- 235000012239 silicon dioxide Nutrition 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- 238000007711 solidification Methods 0.000 description 3
- 230000008023 solidification Effects 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 239000004408 titanium dioxide Substances 0.000 description 3
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 3
- LXOFYPKXCSULTL-UHFFFAOYSA-N 2,4,7,9-tetramethyldec-5-yne-4,7-diol Chemical compound CC(C)CC(C)(O)C#CC(C)(O)CC(C)C LXOFYPKXCSULTL-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 238000007259 addition reaction Methods 0.000 description 2
- 125000002723 alicyclic group Chemical group 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 125000003368 amide group Chemical group 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000006229 carbon black Substances 0.000 description 2
- 230000008021 deposition Effects 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 150000002513 isocyanates Chemical class 0.000 description 2
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 2
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 230000001681 protective effect Effects 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 230000001105 regulatory effect Effects 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000011877 solvent mixture Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 230000000007 visual effect Effects 0.000 description 2
- MNCMBBIFTVWHIP-UHFFFAOYSA-N 1-anthracen-9-yl-2,2,2-trifluoroethanone Chemical group C1=CC=C2C(C(=O)C(F)(F)F)=C(C=CC=C3)C3=CC2=C1 MNCMBBIFTVWHIP-UHFFFAOYSA-N 0.000 description 1
- LXQOQPGNCGEELI-UHFFFAOYSA-N 2,4-dinitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O LXQOQPGNCGEELI-UHFFFAOYSA-N 0.000 description 1
- 125000003890 2-phenylbutyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003542 3-methylbutan-2-yl group Chemical group [H]C([H])([H])C([H])(*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- UIKUBYKUYUSRSM-UHFFFAOYSA-N 3-morpholinopropylamine Chemical compound NCCCN1CCOCC1 UIKUBYKUYUSRSM-UHFFFAOYSA-N 0.000 description 1
- 125000006201 3-phenylpropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 1
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- POFAUXBEMGMSAV-UHFFFAOYSA-N [Si].[Cl] Chemical compound [Si].[Cl] POFAUXBEMGMSAV-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
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000004873 anchoring Methods 0.000 description 1
- 125000002078 anthracen-1-yl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C([*])=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 125000000748 anthracen-2-yl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C([H])=C([*])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 230000008033 biological extinction Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 238000012937 correction Methods 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- AYOHIQLKSOJJQH-UHFFFAOYSA-N dibutyltin Chemical compound CCCC[Sn]CCCC AYOHIQLKSOJJQH-UHFFFAOYSA-N 0.000 description 1
- 239000002612 dispersion medium Substances 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- KSCFJBIXMNOVSH-UHFFFAOYSA-N dyphylline Chemical group O=C1N(C)C(=O)N(C)C2=C1N(CC(O)CO)C=N2 KSCFJBIXMNOVSH-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000013467 fragmentation Methods 0.000 description 1
- 238000006062 fragmentation reaction Methods 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- CBFCDTFDPHXCNY-UHFFFAOYSA-N icosane Chemical compound CCCCCCCCCCCCCCCCCCCC CBFCDTFDPHXCNY-UHFFFAOYSA-N 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- RUDCBGCNXOSCTI-UHFFFAOYSA-N n-methoxy-4-[4-(methoxyamino)phenyl]aniline Chemical compound C1=CC(NOC)=CC=C1C1=CC=C(NOC)C=C1 RUDCBGCNXOSCTI-UHFFFAOYSA-N 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- FGFWCOVNCKWNLU-UHFFFAOYSA-N oxalic acid;tin Chemical compound [Sn].OC(=O)C(O)=O FGFWCOVNCKWNLU-UHFFFAOYSA-N 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000004848 polyfunctional curative Substances 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- TVDSBUOJIPERQY-UHFFFAOYSA-N prop-2-yn-1-ol Chemical compound OCC#C TVDSBUOJIPERQY-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000010008 shearing Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000007962 solid dispersion Substances 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000003351 stiffener Substances 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 239000012974 tin catalyst Substances 0.000 description 1
- 150000003606 tin compounds Chemical class 0.000 description 1
- 238000005829 trimerization reaction Methods 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—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
-
- 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
- C08G18/2805—Compounds having only one group containing active hydrogen
- C08G18/2815—Monohydroxy compounds
-
- C—CHEMISTRY; METALLURGY
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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Abstract
本发明公开了作为尤其适用于颜料、填料和消光剂的分散剂或防沉降剂的加合化合物。所述化合物通过平均官能度2-6的多异氰酸酯与带有聚合物链和异氰酸酯反应性基团的化合物,以及具有杂环氮和异氰酸酯反应性基团的化合物,以及优选地,带有异氰酸酯反应性基团和颜料亲和基团的化合物反应而制备。
Description
技术领域
本发明涉及加合化合物,制备这些加合化合物的方法,以及这些加合化合物作为分散剂或防沉降剂的用途,特别是用于颜料、填料和消光剂。
背景技术
在涂料中,存在与配制品中的固体颗粒通常包括用于着色的颜料、用作填料的补充剂,和/或用于特殊目的的其它固体材料如消光剂。分散剂是一种通过降低固体颗粒与液体介质这两种组分间的表面张力而促进这些固体颗粒分散并稳定在液体介质中的物质。分散剂通常是具有阳离子、阴离子或非离子结构的表面活性物质。分散剂的存在大大降低了分散所需要的能量并且使分散时间最小化。分散剂,以相对小的量,或直接施加给固体颗粒,或加入到液体介质中。分散剂的用量取决于要分散的固体颗粒的尺寸和表面类型。例如,炭黑相较于二氧化钛需要更多的量的分散剂以获得尽可能小的通常在纳米范围的颗粒尺寸。然而,对于消光剂如通常具有高密度的二氧化硅而言,挑战在于使其分散和稳定。
为了提供用于各种固体颗粒,特别是用于颜料、填料和消光剂的有效的分散剂以使涂料组合物能对再附聚和沉降稳定,已经进行了许多努力。使用消光剂的一个常见问题是在涂料配制品中以及以浓缩物的形式中为获得消光效果所需的重的和相对大的颗粒的沉降。这些沉淀物中更复杂的是可能形成坚硬的沉淀物,相比于柔软的沉淀物,其不能通过振摇或搅拌而再次分散,而是需要强剪切力去破碎,例如使用研磨、碾制或分散步骤。
例如,基于多官能异氰酸酯的聚合分散剂、带有分散性基团的聚合物化合物和化合物是长期以来人们所熟知的,并且例如描述于US4647647、US5425900、US6506899、US7741404、US8362300等中。
US4647647公开了由平均官能度为2.5-6的多异氰酸酯与单羟基聚醚和/或聚酯化合物以及具有至少一个叔氨基或一个不带氢原子的在基础环(basicring)上的氮的异氰酸酯反应性化合物反应而制备的分散剂。
US6506899公开了由异氰酸酯与亲水性聚(乙二醇)烷基醚、疏水性聚酯或聚丙烯酸酯和含有伯胺和叔胺的二胺反应制备的聚合的颜料分散剂。
US7741404描述了含有固体颗粒消光剂、有机介质和聚氨酯分散剂的非水性组合物,所述聚氨酯分散剂具有基本上线型的骨架并且侧面连接溶剂可溶解的聚酯、聚醚、聚丙烯酸酯或聚烯烃的侧链,包括这些侧链的混合物。
US8362300描述了由a)一种或多种含有脲二酮基团的多异氰酸酯与b)一种或多种式Y-(XH)n的化合物反应,并且随后与c)一种或多种通式为Z-NHR的化合物反应制备得到的加合化合物。在式中,XH是异氰酸酯反应性基团,Y是含有一个或多个不与异氰酸酯反应的脂肪族、脂环族、芳脂族和/或芳香族基团的单体或聚合的基团,n为1、2或3,R为氢或烷基并且Z是脂肪族、脂环族和/或芳香族基础基团(basicradical)。
现有技术的产品包含所谓的锚定基团,其吸收在被分散的固体颗粒上并且也有与分散介质相容的聚合物链。存在大量的商购可得的聚氨酯分散剂。但是,它们仅部分解决所遇到的问题。
在一些分散剂的制备中,可能发生副反应并且最终产物是高度复杂并且难于确定的反应混合物,其可能难以重现,这导致了性能的不一致。还存在其它问题,例如,这些分散剂制备中的一些需要在极端的反应条件下进行,例如非常高的反应温度和长的反应时间。这增加了生产成本并且导致最终的涂料使用受限。因此,存在着增长的对用于固体颗粒的分散剂的需求,该分散剂相较于现有技术中可获得的分散剂表现出改进的性能并且能够更有效地生产。
本发明的目的是提供适合作为有效稳定颜料、填料、消光剂等的分散剂或防沉降剂的加合化合物。本发明的另一个目的是形成涂料配制品或可以用于涂料配制品中的分散物质的浓缩物,其是稳定且不需要再分散或再研磨就可使用的。
发明概述
本发明提供通过下面的组分反应来制备的加合化合物:
a)一种或多种平均官能度为2-6的多异氰酸酯;
b)一种或多种包含至少一条选自聚酯、聚醚、聚丙烯酸酯、聚氨酯、聚烯烃及其组合的链和至少一个异氰酸酯反应性基团的化合物,其中所述至少一个异氰酸酯反应性基团是氨基;以及
c)一种或多种选自N-(3-氨基丙基)咪唑(API)、苯胍胺(BGA)和N-(2-氨基乙基)哌嗪(AEP)的化合物。
优选地,该加合化合物通过进一步与下面的组分反应来制备;
d)一种或多种包含至少一个异氰酸酯反应性基团和至少一个颜料亲和基团的化合物,其中组分d)不同于组分c)。
本发明进一步提供通过组分a)、b)、c)和任选的d)相继反应来制备所述加合化合物的方法。
本发明进一步提供所述加合化合物作为分散剂或防沉降剂的用途。
本发明进一步提供颜料、填料或消光剂组合物,其包含颜料、填料或消光剂和至少一种加合化合物。
发明详述
组分a)
为制备本发明的加合化合物可以使用该技术领域中已知的任意多异氰酸酯。这些多异氰酸酯可具有2-6的平均官能度,优选为2-5,并且更优选为2.5-4。特别优选地,它们包括基于甲苯二异氰酸酯(TDI)、六亚甲基二异氰酸酯(HDI)、亚甲基二苯基二异氰酸酯(MDI)、异氟尔酮二异氰酸酯(IPDI)的多异氰酸酯以及基于甲苯二异氰酸酯(TDI)、六亚甲基二异氰酸酯(HDI)、亚甲基二苯基二异氰酸酯(MDI)和异氟尔酮二异氰酸酯(IPDI)中的两种或多种的混合物的多异氰酸酯,优选基于甲苯二异氰酸酯(TDI)和六亚甲基二异氰酸酯(HDI)的混合物的多异氰酸酯。
这些化合物是商购可得的,并且通常并非以纯的形式存在并包含具有类似结构的化合物的混合物。术语“官能度”的使用指的是“平均官能度”,意为就异氰酸酯基团而言,该商购产品具有给定的官能度。例如,“官能度2”的意思是,一分子中包含平均2个游离的异氰酸酯基团。平均官能度可以通过测定数均分子量(Mn)来实验测定。另外,测量NCO数并且由此计算NCO当量重量。平均官能度是由数均分子量(Mn)和NCO当量重量形成的比率。
商购可得的基于六亚甲基二异氰酸酯/甲苯二异氰酸酯(HDI/TDI)的多异氰酸酯例如为商品名为的那些,基于甲苯二异氰酸酯(TDI)的多异氰酸酯例如为来自Bayer的商品名为的那些,基于亚甲基二苯基二异氰酸酯(MDI)的多异氰酸酯例如为来自Huntsman的商品名为的那些,和三聚异氟尔酮二异氰酸酯(IPDI)例如是来自EvonikIndustriesAG的它们具有下述简化的结构或类似结构。
在这些多异氰酸酯中,优选基于六亚甲基二异氰酸酯/甲苯二异氰酸酯(HDI/TDI)的多异氰酸酯或基于亚甲基二苯基二异氰酸酯(MDI)的那些。这些多异氰酸酯尤其适用于生产用于颜料的分散剂,因为它们提供了更好的相容性。基于亚甲基二苯基二异氰酸酯(MDI)的多异氰酸酯尤其适用于生产分散和/或稳定二氧化硅消光剂的分散剂。
组分b)
组分b)可以是一种或多种包含至少一条选自聚酯、聚醚、聚丙烯酸酯、聚氨酯、聚烯烃及其组合的链的化合物。所述至少一条选自聚酯、聚醚、聚丙烯酸酯、聚氨酯、聚烯烃及其组合的链包含至少一个异氰酸酯反应性基团,其中所述至少一个异氰酸酯反应性基团是氨基。优选该至少一条链包含一个单独的异氰酸酯反应性基团,其中所述一个单独的异氰酸酯反应性基团是氨基。
所述组合可以是物理性质的(即在合成中使用聚合物的混合物)或化学性质的(即无规或嵌段共聚物,基团的交替或链段聚合物)。
优选组分b)具有至少300g/mol的数均分子量(Mn),优选300-10000g/mol,1000-10000g/mol并且最优选为1000-2500g/mol,通过凝胶渗透色谱法测定。
凝胶渗透色谱法(GPC)是一种提供聚合物的重均和数均分子量以及整体分子量分布的方法。测定聚合物的Mn和Mw值的技术是众所周知的并且在众多书籍和文章中进行了描述。例如,在W.W.Yan,J.J.Kirkland和D.D.Bly,“M/odernSizeExclusionLiquidChromatographs”,JohnWiley&Sons,Inc.,1979中描述了测定聚合物的Mn和分子量分布的方法。
组分b)可优选选自氨基官能的聚醚、聚酯或聚醚-聚酯,更优选选自具有(C2-C4)亚烷基氧基重复单元的聚醚胺或聚醚二醇。进一步优选氨基在组分b)的聚合物链的末端,或其组合。
在本发明的一些实施例中,组分b)可以是两种或多种聚合物的物理或化学混合物,所述聚合物选自氨基官能的聚醚、聚酯和聚醚-聚酯,优选选自具有(C2-C4)亚烷基氧基重复单元的聚醚胺或聚醚二醇。氨基优选在聚合物链的末端。
商购可得的组分b)的一个例子包括来自Huntsman公司的商品名为的聚醚胺。
组分b)的用量可为5-90当量%,优选30-80当量%,更优选35-75当量%,基于组分a)的异氰酸酯基团计。
组分c)
组分c)是选自由N-(3-氨基丙基)咪唑(API)、苯胍胺(BGA)和N-(2-氨基乙基)哌嗪(AEP)的化合物。这些组分c)所选化合物均包含至少一个基础环上的氮和至少一个异氰酸酯反应性基团,其中所述至少一个基础环上的氮对组分a)的异氰酸酯基团呈化学惰性。对组分a)的异氰酸酯基团具有反应性的基础环上的氮也可以存在于组分c)中,只要存在至少一个对组分a)的异氰酸酯基团呈化学惰性的基础环上的氮,如N-(2-氨基乙基)哌嗪(AEP)即是这种情况。
这些化合物的结构如下所示:
化合物N-(3-氨基丙基)咪唑和苯胍胺尤其适用于形成用于生产颜料用分散剂的根据本发明的加合化合物。N-(2-氨基乙基)哌嗪尤其适用于形成用于生产消光剂用防沉降剂的根据本发明的加合化合物。
组分c)的用量可为10-90当量%,优选20-70当量%,更优选30-60当量%,基于组分a)的异氰酸酯基团计。
组分d)
组分d)是包含至少一个异氰酸酯反应性基团和至少一个颜料亲和基团的化合物,并且不同于组分c)。
此处所用的颜料亲和基团指的是在颜料表面具有强吸收力的官能团。
例子包括取代或未取代的羧基、酯、酰胺基、羟基、氨基、巯基、磺酸基(sulfonic)、酰亚胺、脲、氰基、偶氮基、氨酯基(urethane)、烷基、亚烷基、烯基、芳烷基、或芳基或它们的组合。所述取代基可以是直链或支链烷基、芳烷基或芳基,其也可进一步被取代,例如被C1-C40烷基或C6-C14芳基取代。
特别优选下面的基团:C1-C40烷基,例如甲基、乙基、正丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基、正戊基、异戊基、仲戊基、新戊基、1,2-二甲基丙基、异戊基、正己基、异己基、仲己基、正庚基、异庚基、正辛基、正壬基、正癸基、正十二烷基、正十六烷基,和正二十烷基;C6-C14芳基,例如苯基、α-萘基、β-萘基、1-蒽基、2-蒽基,和9-蒽基,C7-G13芳烷基,优选C7-C12苯基烷基,例如苄基、1-苯乙基、2-苯乙基、1-苯基丙基、2-苯基丙基、3-苯基丙基、新苯基(1-甲基-1-苯乙基)、1-苯基丁基、2-苯基丁基、3-苯基丁基,和4-苯基丁基,特别优选苄基。
优选地,组分d)的分子量(Mw)为70-300g/mol。
并且在本发明的一些实施例中,组分d)选自3-羟基丙腈(ECH)、二丁基胺(DBA)、叔丁基胺(TBA)、2,4,7,9-四甲基-5-癸炔二醇(TMDD)、氨基蒽醌、苯基萘胺、N,N-二甲基氨基乙醇、对氨基偶氮苯和二甲氧基联苯胺。
对于本发明而言组分d)是优选的并且可以以不大于60当量%,优选5-50当量%,最优选5-30当量%的量来使用,基于组分a)的异氰酸酯基团计。
本发明加合化合物的制备
本发明的加合化合物可以在10-100℃,优选为10-80℃,最优选为10-60℃的温度下,通过使组分a)、b)、c)和优选的d)相继反应,直到所有的异氰酸酯基团完全反应并且NCO的含量为0或忽略不计来制备。上面的反应可优选在惰性溶剂中进行,例如乙酸乙酯、乙酸丁酯、乙酸甲氧基丙酯和/或它们的混合物。在氨基化合物例如聚醚胺与异氰酸酯化合物反应的情况中,该反应可以在10℃的低温下进行。可任选使用加快异氰酸酯加成反应的催化剂,但是通常是不需要的。如果需要,催化剂的例子包括锡化合物,如二羧酸二丁基锡、二月桂酸二丁基锡或二乙酸锡。催化剂的用量优选为0至1重量%,基于反应混合物的总重量计。
本发明的加合化合物可通过下面的结构示意性说明。例如,基于六亚甲基二异氰酸酯/甲苯二异氰酸酯的多异氰酸酯(例如D-8中的结构I,例如可在商品名下获得)以及基于亚甲基二苯基二异氰酸酯(例如M-3中的结构II,例如可在商品名下获得)与如前所述的聚醚胺和其它胺类反应。
实施例
下文中通过实施例对发明进行说明。除非另有说明,份数为重量份。游离NCO含量和NCO加成反应的进程通过FTIR通过观察2270cm-1附近的特征NCO基团而测定,或者根据DINENISO11909来测定它们。
D-1至D-17以及M-1至M-5的组分描述在表1中。除非另有说明,表1中反应物的当量比为A部分∶B部分∶C部分∶D部分=1∶0.5∶0.4∶0.1。其中,组分c包括两部分,第一部分与第二部分的比例为3∶1,并且第二部分在C的第一部分在基于相应的NCO%反应完全后才加入。
加合化合物D-1至D-17和M-1至M-5的制备
用作对比例的加合化合物的制备借助加合化合物D-1示例性示出:
在N2保护气氛下,将106.9份(60%,在乙酸丁酯中)与551.2份乙酸甲氧基丙酯混合,形成混合物。向该混合物中经10分钟加入322.0g内部自制的聚酯中间体PE-CA2。混合物的温度增加至60℃,加入0.5份锡催化剂。反应在60℃下维持约2小时直至50%的所使用的NCO基团进行了反应。将反应温度降至低于30℃并且向反应容器中加入13.4份API。该反应在室温下维持1小时直至40%的所使用的NCO基团进行了反应。然后向反应混合物中加入6.0份二丁基胺并且搅拌直至所有的NCO基团通过反应被耗尽。所产生的在乙酸甲氧基丙酯中的产物溶液准备在下面的应用测试中用作分散剂。
其它作为对比例说明的加合化合物通过与用来制备加合化合物D-1类似的规程通过相应地改变组分和调节反应条件来制备。
根据本发明的加合化合物的制备借助加合化合物D-8示例性示出:
在N2保护气氛下,将122.8份(60%,在乙酸丁酯中)与550.9份乙酸甲氧基丙酯混合,形成混合物。向该混合物中经30分钟加入307.0份然后使该反应维持约15分钟直至50%的所使用的NCO基团进行了反应。然后向反应容器中加入15.4份API并在室温下维持该反应直至40%的所使用的NCO基团进行了反应。然后向反应混合物中加入3.97份二丁基胺并且进行搅拌直至所有的NCO基团通过反应被耗尽。所产生的在乙酸甲氧基丙酯中的产物溶液准备在下面的应用测试中用作分散剂。
其它根据本发明的加合化合物通过与用来制备加合化合物D-8类似的规程通过相应地改变组分和调节反应条件来制备。
表1加合化合物D-1至D-7,D-8至D-17和M-1,M-2以及M3至M5
标记为D-1至D-17的加合化合物用于分散颜料。
标记为M-1至M-5的加合化合物用于分散消光剂。
加合化合物D-1至D-7和M-1,M-2表示使用羟基官能团的组分b)制备的对比例。
加合化合物D-8至D-17和M-3至M-5表示使用氨基官能团的组分b)制备的根据本发明的实施例。
基于TDI/HMDI的多异氰酸酯,60%,在乙酸丁酯溶液中,NCO含量为10.5%,可由Bayer获得。
基于TDI的多异氰酸酯,51%,在乙酸丁酯溶液中,NCO含量为8.0%,可由Bayer获得。
基于IPDI的多异氰酸酯,70%,在乙酸丁酯溶液中,游离NCO含量为12%,可由EvonikIndustriesAG获得。
基于MDI的多异氰酸酯,具有游离NCO含量为30.5%,可由Huntsman获得。
JA2070:PO/EO摩尔比为10/31的聚醚胺;平均Mn为2000,可由Huntsman获得。
PE-CA1指的是内部自制的Mn为1500的己内酯聚酯,由聚(乙二醇)甲基醚(Mn1000)引发。
PE-CA2指的是内部自制的Mn为2410的己内酯聚酯,由辛醇引发。
PE-CA3指的是内部自制的Mn为2326的己内酯-戊内酯聚酯,由炔丙醇引发。
PE-CA4指的是内部自制的Mn为4523的己内酯-戊内酯聚酯,由辛醇引发。
PE-CA5指的是内部自制的Mn为1500的己内酯聚酯,由3-羟基丙腈(ethylencyanhydride)(ECH)引发。
对于所有的PE-CA系列聚合物,在PL凝胶柱上通过GPC测定Mn,使用二甲基乙酰胺+10g/L氯化锂作为移动相并且聚苯乙烯作为校准基准。
LJ-MA指的是内部自制的基于一元醇的聚甲基丙烯酸丁酯,78.2%,在PMA中,Mn为920,在PL凝胶柱上通过GPC测定,使用四氢呋喃+0.1%三氟醋酸作为移动相并且聚(甲基丙烯酸甲酯)作为校准基准。
API指的是N-(3-氨基丙基)咪唑,可由BASF获得。
AEP指的是N-(2-氨基乙基)哌嗪,可由Huntsman获得。
APM指的是氨基丙基吗啉,可由Huntsman获得。
BGA指的是苯胍胺,可由T.C.I.获得。
DNA指的是2,4-二硝基苯胺,可由ProlificChemical获得。
DBA指的是二丁基胺,可由Merck获得。
TBA指的是叔丁基胺,可由Merck获得。
ECH指的是3-羟基丙腈,可由EvonikIndustriesAG获得。
TMDD指的是2,4,7,9-四甲基-5-癸炔-4,7-二醇,可由BASF获得。
涂料组合物的制备
根据表2中说明的配方制备包含D-1至D-17中的任意一种加成组合物的卷材涂料组合物。
表2卷材涂料黑色涂料
*颜料上的分散剂固体为64%。
卷材涂料白色涂料也根据下表3中的配方制备,用来测试加合化合物D-1至D-17的颜色接受程度和色彩强度。
表3卷材涂料白色涂料
*颜料上的分散剂固体为1.6份;基于50份固体分散剂。
为了制备涂料,将部分聚酯树脂、溶剂、分散剂、颜料和2mm玻璃珠混合并且随后用LAUDisperserDAS200分散120分钟(针对炭黑颜料)或60分钟(针对二氧化钛)。随后用筛子从分散的膏中分离出玻璃珠。接下来,加入树脂、溶剂、流动添加剂和催化剂的剩余部分并且在LAUDisperserDAS200中均匀混合15分钟。为了制备干膜面板,滴加一滴涂料(5-10克)至锡板上,使用绕线公尺棒(awirewoundmeterbar)RK#32制备约64微米的湿涂料膜。然后将锡板在300℃(峰值金属温度224-232℃)下烘烤30秒。
包含选自M-1至M-5的加合化合物的2KPUAlkyd基木材涂料组合物根据表4中说明的配方来制备。
表42KPUAlkyd基木材涂料1:
1硬化剂:DesmodurL-75,芳香族多异氰酸酯(Bayer);醇酸涂料/DesmodurL-75/溶剂混合物的混合比率=100/32/10(溶剂混合物=二甲苯/乙酸丁酯/乙酸甲氧基丙酯=50/40/10)。
2二氧化硅上的分散剂固体为2.5%。
表4中的所有组分,除了消光剂(未处理的二氧化硅),是预先在容器中混合的。消光剂在600rpm下加入并且随后在2000rpm下完全分散至少15分钟直到其变得均匀。为了制备干膜面板,首先滴加一滴涂料/硬化剂混合物(5-10克)在黑色卡片上。然后使用绕线公尺棒RK#32沉积约64微米的湿涂料膜。然后在60℃下烘烤涂料膜15分钟。
性能测试
涂料的粘度根据ASTMD1200-10用4#Ford杯测定。
在至少8小时的静置时间后,在25℃下在10、100和1000s-1的剪切速率下使用AntonPaarMCR-301测量分散过的颜料膏的粘度。
根据ASTMD523-08使用光泽计在适当固化的涂料膜上测定涂料在60℃下的光泽度。测定了在60℃下储存1周前后的光泽度值。
根据ASTME430-91使用浊度计在适当固化的涂料膜上测定浊度。视觉评价也是需要的。
对在60℃下存储5天后的脱水收缩作用和沉积作用进行了视觉评价。
为了检查着色涂料的色彩接受度和色彩强度,将白色(二氧化钛)卷材涂料和黑色(炭黑)卷材涂料称重并使用SpeedMixerDAC150.1以2000rpm彻底混合1分钟,比例为100∶1(白色涂料∶黑色涂料)。混合后,将一滴着色涂料(5-10克)浇铸在锡板上,厚度大约为64微米。随后使用手指擦掉1/4的涂料表面以测定恒定的色彩(标准化的进行10次摩擦)。涂料膜固化后,测定擦除区域和未擦除区域的色彩的差别作为色彩接受度。在上面提到的面板的未擦除区域上通过计算Kubelka-Munk方程的修正型式中的Y值(CIE1931XYZ)测定色彩强度。
在卷材涂料体系中用作分散颜料的D系列加合化合物的应用结果总结在表5中。从BYK商购可得的聚氨酯分散剂DB163和DB170作为额外的对比例。
表5用于分散颜料的D系列加合化合物的性能1
注释:
1表中所有的性能均在60℃储存前测定。
2>95%为4分,85-95%为3分,75-85%为2分,以及<75%为1分。
30-10秒为4分,10-20秒为3分,20-30秒为2分,以及大于30秒为1分。
4<0.2为4分,0.2-0.5为3分,0.5-1为2分,以及>1为1分。
590-100为4分,80-90为3分,70-80为2分,以及<70为1分。
6<60为4分,60-70为3分,70-80为2分,以及>80为1分。
从表5可以看出,根据本发明的D-8至D-17的所有D系列加合化合物相对于对比例在色彩强度和色彩可接受度上表现出可比较的或更好的性能,并且根据本发明的D-8至D-17的所有D系列加合化合物相对于对比例表现出可比较或更好的综合性能。
在卷材涂料体系中的2KPU体系中用于分散消光剂的M系列加合化合物的应用结果总结在表6中。来自BYK的DB103和来自BASF的Efka4010用作额外的对比例,表现出了商购可得的消光剂用分散剂的性能。
表6用于分散消光剂的M系列加合化合物的性能
注释:
1在60℃下储存7天前后,在60℃下进行测定;光泽度<70为4分,70-75为3分,75-80为2分,>80为1分,由于观察到坚硬的沉积,0=未测定。
2储存前测定;<600cP为4分,600-800cP为3分,800-1000cP为2分,以及>1000cP为1分。
3在60℃储存7天后测定;未分离为4分,1-5%为3分,5-20%为2分以及>20%分离为1分。
4在60℃下储存5天后测定;未沉积为4分,微弱沉积为3分,柔软沉积为2分以及坚硬沉积为1分。
从表6中可以看到,根据本发明的M-3至M-5的所有M系列加合化合物在光泽度和沉积作用方面相较于对比例表现出更好的性能。另外,根据本发明的M系列加合化合物相较于对比例表现出更好的综合性能。
Claims (15)
1.通过下述组分的反应制备的加合化合物:
a)一种或多种平均官能度为2-6的多异氰酸酯;
b)一种或多种包含至少一条选自聚酯、聚醚、聚丙烯酸酯、聚氨酯、聚烯烃及其组合的链以及至少一个异氰酸酯反应性基团的化合物,其中所述至少一个异氰酸酯反应性基团是氨基;以及
c)一种或多种选自N-(3-氨基丙基)咪唑(API)、苯胍胺(BGA)和N-(2-氨基乙基)哌嗪(AEP)的化合物。
2.根据权利要求1的加合化合物,其中组分c)是N-(3-氨基丙基)咪唑(API)或苯胍胺(BGA)。
3.根据权利要求1的加合化合物,其中组分c)是N-(2-氨基乙基)哌嗪(AEP)。
4.根据前述任一权利要求的加合化合物,其中
组分b)的用量为5-90当量%以及
组分c)的用量为10-90当量%;
基于组分a)的异氰酸酯基团计。
5.根据前述任一权利要求的加合化合物,其中
组分b)选自具有(C2-C4)亚烷基氧基重复单元的聚醚胺或聚醚二醇及其组合。
6.根据前述任一权利要求的加合化合物,其中组分b)的至少一个氨基在聚合物链的末端。
7.根据前述任一权利要求的加合化合物,其中该加合化合物通过进一步与组分d)反应来制备
d)包含至少一个异氰酸酯反应性基团和至少一个颜料亲和基团的一种或多种化合物,其中组分d)不同于组分c)。
8.根据权利要求7的加合化合物,其中组分d)的异氰酸酯反应性基团选自氨基、羟基和巯基,并且所述颜料亲和基团选自氰基、偶氮基、烷基、亚烷基、烯基、芳烷基和芳基。
9.根据权利要求7或8的加合化合物,其中组分d)选自叔丁基胺、二丁基胺、3-羟基丙腈(ethylencyanhydride)、2,4,7,9-四甲基-5-癸炔二醇、苯基萘胺、二甲基联苯胺、对氨基偶氮苯、N,N-二甲基氨基乙醇和氨基蒽醌。
10.根据前述任一权利要求的加合化合物,其中
组分a)选自由六亚甲基二异氰酸酯/甲苯二异氰酸酯(HDI/TDI)、亚甲基二苯基二异氰酸酯(MDI)和它们的混合物。
11.制备根据前述权利要求任一项所述的加合化合物的方法,其特征在于组分a)与组分b)、c)以及任选的d)相继反应。
12.根据权利要求1-11任一项所述的加合化合物作为用于颜料、填料和消光剂的分散剂或防沉降剂的用途。
13.根据权利要求2的加合化合物作为用于颜料的分散剂或防沉降剂的用途。
14.根据权利要求3的加合化合物作为用于消光剂的分散剂或防沉降剂的用途。
15.颜料、填料或消光剂组合物,其分别包含颜料、填料或消光剂以及至少一种根据权利要求1-11之一的加合化合物。
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US (1) | US9574044B2 (zh) |
EP (1) | EP2998017B1 (zh) |
CN (1) | CN105440238B (zh) |
BR (1) | BR102015023811A2 (zh) |
ES (1) | ES2765548T3 (zh) |
Cited By (4)
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CN106222727A (zh) * | 2016-08-27 | 2016-12-14 | 合肥普庆新材料科技有限公司 | 一种用于含银粉的装饰性电泳漆涂装过程中调整银粉效果的调整剂 |
CN107998981A (zh) * | 2017-12-05 | 2018-05-08 | 万华化学(宁波)有限公司 | 聚酯超分散剂及其制备,以及一种异氰酸酯的制备方法 |
CN109476803A (zh) * | 2016-07-11 | 2019-03-15 | 赢创德固赛有限公司 | 可用于制造聚氨酯泡沫的胺组合物 |
CN113631671A (zh) * | 2019-03-12 | 2021-11-09 | 亨斯迈石油化学有限责任公司 | 由异氰酸酯和胺制备的分散剂 |
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US20180186917A1 (en) | 2015-07-08 | 2018-07-05 | Byk-Chemie, Gmbh | Reaction products containing urethane groups and urea groups |
CN111040181A (zh) * | 2019-12-26 | 2020-04-21 | 博邦新材料科技(广州)有限公司 | 一种聚丙烯酸酯分散剂及其制备方法 |
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Also Published As
Publication number | Publication date |
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US9574044B2 (en) | 2017-02-21 |
CN105440238B (zh) | 2020-11-17 |
US20160083502A1 (en) | 2016-03-24 |
EP2998017B1 (en) | 2019-11-13 |
ES2765548T3 (es) | 2020-06-09 |
BR102015023811A2 (pt) | 2016-09-20 |
EP2998017A1 (en) | 2016-03-23 |
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