CN106146796A - 氨基甲酸乙酯分散剂 - Google Patents
氨基甲酸乙酯分散剂 Download PDFInfo
- Publication number
- CN106146796A CN106146796A CN201510144172.0A CN201510144172A CN106146796A CN 106146796 A CN106146796 A CN 106146796A CN 201510144172 A CN201510144172 A CN 201510144172A CN 106146796 A CN106146796 A CN 106146796A
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- CN
- China
- Prior art keywords
- dispersant
- compound
- independently selected
- diisocyanate
- 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.)
- Pending
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- 239000002270 dispersing agent Substances 0.000 title claims abstract description 73
- 150000003673 urethanes Chemical class 0.000 title description 8
- 150000001875 compounds Chemical class 0.000 claims abstract description 54
- 239000005056 polyisocyanate Substances 0.000 claims abstract description 25
- 229920001228 polyisocyanate Polymers 0.000 claims abstract description 25
- 239000000049 pigment Substances 0.000 claims abstract description 22
- 229920000768 polyamine Polymers 0.000 claims abstract description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 18
- 150000001412 amines Chemical class 0.000 claims abstract description 17
- -1 Urethane ester Chemical class 0.000 claims abstract description 14
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000006185 dispersion Substances 0.000 claims abstract description 10
- 239000012634 fragment Substances 0.000 claims abstract description 4
- 238000002360 preparation method Methods 0.000 claims abstract description 4
- 239000000203 mixture Substances 0.000 claims description 53
- 239000012948 isocyanate Substances 0.000 claims description 33
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 21
- 150000002513 isocyanates Chemical class 0.000 claims description 20
- 239000007787 solid Substances 0.000 claims description 18
- 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 13
- 150000002148 esters Chemical class 0.000 claims description 10
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 claims description 10
- 239000013638 trimer Substances 0.000 claims description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 9
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 9
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 claims description 9
- 239000005057 Hexamethylene diisocyanate Substances 0.000 claims description 8
- 239000007788 liquid Substances 0.000 claims description 8
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical class NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 claims description 7
- 125000005442 diisocyanate group Chemical group 0.000 claims description 7
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 claims description 7
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims description 6
- 239000005058 Isophorone diisocyanate Substances 0.000 claims description 6
- 229920000728 polyester Polymers 0.000 claims description 6
- OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical compound NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 claims description 5
- 125000000219 ethylidene group Chemical group [H]C(=[*])C([H])([H])[H] 0.000 claims description 5
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 claims description 4
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 claims description 4
- 239000012860 organic pigment Substances 0.000 claims description 4
- 239000000843 powder Substances 0.000 claims description 4
- 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 3
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 3
- 150000007824 aliphatic compounds Chemical class 0.000 claims description 3
- 150000001491 aromatic compounds Chemical class 0.000 claims description 3
- 150000001991 dicarboxylic acids Chemical class 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 239000001023 inorganic pigment Substances 0.000 claims description 3
- LSHROXHEILXKHM-UHFFFAOYSA-N n'-[2-[2-[2-(2-aminoethylamino)ethylamino]ethylamino]ethyl]ethane-1,2-diamine Chemical compound NCCNCCNCCNCCNCCN LSHROXHEILXKHM-UHFFFAOYSA-N 0.000 claims description 3
- 229960001124 trientine Drugs 0.000 claims description 3
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 claims description 2
- 150000001334 alicyclic compounds Chemical class 0.000 claims description 2
- 150000002466 imines Chemical class 0.000 claims description 2
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 claims description 2
- 229920000083 poly(allylamine) Polymers 0.000 claims description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims 1
- 239000005977 Ethylene Substances 0.000 claims 1
- WVIIMZNLDWSIRH-UHFFFAOYSA-N cyclohexylcyclohexane Chemical group C1CCCCC1C1CCCCC1 WVIIMZNLDWSIRH-UHFFFAOYSA-N 0.000 claims 1
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 claims 1
- QVTVDJWJGGEOGX-UHFFFAOYSA-N urea;cyanide Chemical compound N#[C-].NC(N)=O QVTVDJWJGGEOGX-UHFFFAOYSA-N 0.000 claims 1
- 125000001261 isocyanato group Chemical group *N=C=O 0.000 description 26
- 238000006243 chemical reaction Methods 0.000 description 25
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 22
- 150000005217 methyl ethers Chemical class 0.000 description 15
- 239000000376 reactant Substances 0.000 description 12
- 238000012544 monitoring process Methods 0.000 description 11
- 229910052757 nitrogen Inorganic materials 0.000 description 11
- 238000004448 titration Methods 0.000 description 11
- 229920001223 polyethylene glycol Polymers 0.000 description 10
- 239000004814 polyurethane Substances 0.000 description 10
- 229920002635 polyurethane Polymers 0.000 description 10
- 229910052799 carbon Inorganic materials 0.000 description 9
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical group NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- 238000009736 wetting Methods 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- 239000011230 binding agent Substances 0.000 description 6
- 239000004202 carbamide Chemical group 0.000 description 5
- 235000013877 carbamide Nutrition 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 229920000233 poly(alkylene oxides) Polymers 0.000 description 4
- 230000003381 solubilizing effect Effects 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 239000003381 stabilizer Substances 0.000 description 3
- VZXPHDGHQXLXJC-UHFFFAOYSA-N 1,6-diisocyanato-5,6-dimethylheptane Chemical compound O=C=NC(C)(C)C(C)CCCCN=C=O VZXPHDGHQXLXJC-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- OZJPLYNZGCXSJM-UHFFFAOYSA-N 5-valerolactone Chemical compound O=C1CCCCO1 OZJPLYNZGCXSJM-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 2
- 229920002873 Polyethylenimine Polymers 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- 238000005352 clarification Methods 0.000 description 2
- 239000008199 coating composition Substances 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 description 2
- 239000013530 defoamer Substances 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 229910052738 indium Inorganic materials 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229940043265 methyl isobutyl ketone Drugs 0.000 description 2
- 239000003973 paint Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 150000003141 primary amines Chemical group 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 150000003335 secondary amines Chemical class 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- MTZUIIAIAKMWLI-UHFFFAOYSA-N 1,2-diisocyanatobenzene Chemical compound O=C=NC1=CC=CC=C1N=C=O MTZUIIAIAKMWLI-UHFFFAOYSA-N 0.000 description 1
- KCZQSKKNAGZQSZ-UHFFFAOYSA-N 1,3,5-tris(6-isocyanatohexyl)-1,3,5-triazin-2,4,6-trione Chemical compound O=C=NCCCCCCN1C(=O)N(CCCCCCN=C=O)C(=O)N(CCCCCCN=C=O)C1=O KCZQSKKNAGZQSZ-UHFFFAOYSA-N 0.000 description 1
- QKOWXXDOHMJOMQ-UHFFFAOYSA-N 1,3,5-tris(6-isocyanatohexyl)biuret Chemical compound O=C=NCCCCCCNC(=O)N(CCCCCCN=C=O)C(=O)NCCCCCCN=C=O QKOWXXDOHMJOMQ-UHFFFAOYSA-N 0.000 description 1
- VOZKAJLKRJDJLL-UHFFFAOYSA-N 2,4-diaminotoluene Chemical compound CC1=CC=C(N)C=C1N VOZKAJLKRJDJLL-UHFFFAOYSA-N 0.000 description 1
- CCTFMNIEFHGTDU-UHFFFAOYSA-N 3-methoxypropyl acetate Chemical compound COCCCOC(C)=O CCTFMNIEFHGTDU-UHFFFAOYSA-N 0.000 description 1
- WJIOHMVWGVGWJW-UHFFFAOYSA-N 3-methyl-n-[4-[(3-methylpyrazole-1-carbonyl)amino]butyl]pyrazole-1-carboxamide Chemical compound N1=C(C)C=CN1C(=O)NCCCCNC(=O)N1N=C(C)C=C1 WJIOHMVWGVGWJW-UHFFFAOYSA-N 0.000 description 1
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical group NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- OWIKHYCFFJSOEH-UHFFFAOYSA-N Isocyanic acid Chemical compound N=C=O OWIKHYCFFJSOEH-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 1
- ISKQADXMHQSTHK-UHFFFAOYSA-N [4-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=C(CN)C=C1 ISKQADXMHQSTHK-UHFFFAOYSA-N 0.000 description 1
- KIBKSNLNGHPFTB-UHFFFAOYSA-L [acetyloxy(diethyl)stannyl] acetate Chemical compound CC([O-])=O.CC([O-])=O.CC[Sn+2]CC KIBKSNLNGHPFTB-UHFFFAOYSA-L 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
- 238000010521 absorption reaction Methods 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 125000004450 alkenylene group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000001118 alkylidene group Chemical group 0.000 description 1
- 125000004419 alkynylene group Chemical group 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 238000004873 anchoring Methods 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052797 bismuth Inorganic materials 0.000 description 1
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 1
- 239000001055 blue pigment Substances 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 125000005587 carbonate group Chemical group 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- JBFHTYHTHYHCDJ-UHFFFAOYSA-N gamma-caprolactone Chemical compound CCC1CCC(=O)O1 JBFHTYHTHYHCDJ-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 229920001600 hydrophobic polymer Polymers 0.000 description 1
- 150000001261 hydroxy acids Chemical group 0.000 description 1
- 125000001841 imino group Chemical group [H]N=* 0.000 description 1
- 239000000976 ink Substances 0.000 description 1
- 150000002527 isonitriles Chemical class 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 150000003951 lactams Chemical class 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
- 239000005416 organic matter Substances 0.000 description 1
- 238000010422 painting Methods 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 229940059574 pentaerithrityl Drugs 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920001495 poly(sodium acrylate) polymer Polymers 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- NNMHYFLPFNGQFZ-UHFFFAOYSA-M sodium polyacrylate Chemical compound [Na+].[O-]C(=O)C=C NNMHYFLPFNGQFZ-UHFFFAOYSA-M 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 125000001302 tertiary amino group Chemical group 0.000 description 1
- 239000012974 tin catalyst Substances 0.000 description 1
- 125000004417 unsaturated alkyl group Chemical group 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 229910052726 zirconium Inorganic materials 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
- C08G18/70—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
- C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
- C08G18/7614—Polyisocyanates or polyisothiocyanates cyclic aromatic containing only one aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
- C09K23/16—Amines or polyamines
-
- 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
- C08G18/283—Compounds containing ether groups, e.g. oxyalkylated monohydroxy compounds
-
- 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
- C08G18/3225—Polyamines
- C08G18/3228—Polyamines acyclic
-
- 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
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Abstract
氨基甲酸乙酯型分散剂,其包括衍生自以下的片段:(1)一种或多种具有至少2.0个异氰酸酯基团的聚异氰酸酯,(2)具有异氰酸酯反应性官能部分的单官能化合物;以及(3)胺官能度为二或更多的聚胺。该分散剂可以在不含溶剂的制备过程中制备。该分散剂可以应用于水基颜料分散体系中。
Description
发明领域
本公开描述了基于氨基甲酸乙酯和脲键的分散剂,其用于在极性介质如研磨料、涂料和油墨中分散有机/无机颜料颗粒。具体地,该分散剂包含具有酰胺、脲和氨基甲酸乙酯基团的有效的多个锚定部分,其集中分布在分散剂分子中并且与使链结构增溶的溶剂相连。
更具体地,上文所述的化学结构适于制备颜料浓缩物,还适于稳定粘合剂、涂料、油墨组合物、塑料和聚合物混合物。作为润湿分散剂,它们降低该体系的粘度,提高储存稳定性和流体性质,并且还可以增强色强度。
背景
多种不同的氨基甲酸乙酯或聚氨酯分散剂含有聚环氧乙烷链,该链存在于与聚氨酯骨架相连的侧链和/或端链中并且搭配多功能的锚定基团。
WO97/19120考虑了水可分散的不饱和聚氨酯分散剂,其包括悬垂的不饱和烃基基团、悬垂的磺酸盐和聚环氧烷。其公开了聚氨酯适于制备疏水聚合物的稳定的水分散体和颜料分散体。
第2009/0221745A1号美国专利描述了基于聚环氧化物主链的聚环氧化物/胺型分散剂,该主链具有作为锚以与颜料表面相互作用的小的胺类分子(苄胺或乙醇胺)和作为增溶尾(solubilizing tail)以在溶剂中延伸的聚醚胺(商标,来自HUNTSMAN的)以及粘合剂介质以提供稳定机制。该润湿分散剂可以与一般粘合剂以及溶剂体系高度相容。
在该领域还有其他进展。第8017686B2号美国专利提到新型聚氨酯分散剂粘合剂,其具有含有基于悬垂的亲水和疏水聚环氧烷的侧基的聚氨酯骨架。在聚氨酯分散剂树脂中的聚环氧烷的含量为至少45%。该文献描述了颜料浓缩物可易于并入涂料组合物中,颜料固体稳定地分散于其中。此外,分散剂树脂可应用于与广谱范围内的不同颜料一起使用,特别是对于难以分散的棘手情况,如DPP red BO(Ciba)、Heliogene Blue L7101F(BASF)和Quindo Violet RV929(Bayer)。
第8664331B2号美国专利还公开了一类聚氨酯分散剂,其含有在侧链中基于聚合物总重量的35wt%至90wt%的大量的环氧乙烷重复单元。作为锚定部分的羧酸基团被并入聚氨酯骨架中。对于颜料浆或涂料组合物,这些优异的分散剂可以提供改善的功能性质,诸如研磨料粘度、光泽度和色强度。
因此,上述分散剂获得许多优异的性能、水可分散性、与粘合剂体系以及各种颜料的广泛相容性、研磨料的更低的粘度以及分散体系的长期稳定性。但是直到现在,在氨基甲酸乙酯或聚氨酯型分散剂的合成过程中一直存在有机溶剂,并且这将容易导致交联的问题,如果涉及诸如聚胺衍生物的多功能的优异的锚定基团。因此,在润湿性能和环境友好问题之间,氨基甲酸乙酯或聚氨酯型分散剂存在缺口。
聚丙烯酸(PAA)、聚丙烯酸钠(NaPAA)及相关衍生物在第3945843A号美国专利中被公开,并且第4767644A号美国专利中有用于不含有机溶剂的分散剂的另一种方法。但是对于有机颜料这类分散剂的润湿能力一直有缺陷,这是由于极性不匹配。因此,其总是与类表面活性剂分散剂组合以增强润湿效果。
这使得更加难以忽视挥发性有机物问题。环境友好问题不仅限制分散剂的应用领域而且限制其生产过程。从氨基甲酸乙酯或聚氨酯类分散剂的合成过程的角度来看,现今一直涉及大量有机溶剂:酯,例如乙酸丁酯和甲氧基丙基乙酸酯;酰胺,例如二甲基甲酰胺;内酰胺,例如N-甲基-2-吡咯烷酮;或酮,例如甲基乙基酮(MEK)和甲基异丁基酮(MIBK)。另一方面,分散剂的润湿能力被高度关注,尤其对于高表面能的情况,例如水性涂料组合物。因此,在环境友好的生产过程与分散剂的颜料润湿性能之间存在缺口。
发明概述
在一个实施方案中,本公开提供分散剂,其包括衍生自以下的片段:(1)一种或多种具有至少2个异氰酸酯基团的聚异氰酸酯,(2)具有异氰酸酯反应性官能部分的单官能化合物;以及(3)胺官能度为二或更多的聚胺。在一些实施方案中,分散剂是水溶性的。
在一些实施方案中,50%-90%当量的聚异氰酸酯的异氰酸酯基团与单官能化合物结合,并且10%-50%当量的异氰酸酯基团与聚胺结合。
在一些实施方案中,单官能化合物独立地选自脂肪族化合物、脂环族化合物和芳香族化合物,及其组合。在一些实施方案中,单官能化合物含有至少一个独立地选自以下的基团:-O-或-COO-及其组合。在一些实例中,单官能化合物的分子量为350至5000。在某些实施方案中,单官能化合物独立地选自含有60%-99%环氧乙烷基团的聚(C2-4-环氧烷)、聚酯低聚物,及其组合。在一些这类实施方案中,聚酯低聚物含有衍生自二羧酸和乙二醇的片段。
在一些实施方案中,聚异氰酸酯是二异氰酸酯,其独立地选自甲苯二异氰酸酯、异佛尔酮二异氰酸酯(IPDI)、六亚甲基二异氰酸酯、二苯甲烷-4,4'-二异氰酸酯、二环己基甲烷-4,4'-二异氰酸酯、1,4-双(2-异氰酸根(isocyanato)-2-基)苯、三甲基六亚甲基二异氰酸酯,或这些二异氰酸酯的混合物。在一些其它实施方案中,聚异氰酸酯独立地选自加合物、异氰酸酯缩二脲、异氰酸酯异氰脲酸酯或这类聚异氰酸酯的混合物。在某些实施方案中,聚异氰酸酯独立地选自甲苯二异氰酸酯和三羟甲基丙烷加合物、六亚甲基二异氰酸酯缩二脲三聚体、六亚甲基二异氰酸酯异氰脲酸酯三聚体、异佛尔酮二异氰酸酯异氰脲酸酯三聚体、六亚甲基二异氰酸酯异氰脲酸酯三聚体,和异佛尔酮二异氰酸酯异氰脲酸酯三聚体。
在一些实施方案中,异氰酸酯反应性官能部分独立地选自羟基、胺或亚胺及其组合。
在一些实施方案中,聚胺独立地选自聚乙烯亚胺(PEI)、聚乙烯胺、聚烯丙基胺低聚物、乙烯亚胺低聚物及其组合。在一些实施方案中,聚胺独立地选自二亚乙基三胺(DETA)、三亚乙基四胺(TETA)、四亚乙基五胺(TEPA)、五亚乙基六胺(PEHA),六亚乙基七胺(HEHA)及其组合。
实施方案详述
本发明提供具有末端增溶基团的分散剂组合物,其通过不含溶剂的合成过程经由氨基甲酸乙酯和脲键获得。它可以用于水基涂料和溶剂基涂料。同时,该分散剂组合物可以提供优异的润湿效力以获得具有极低的粘度以及良好的长期胶体稳定性的色浆。它包括作为分散剂的锚定部分以吸附在颜料表面上的聚胺,和单羟基化合物封端的聚异氰酸酯,以形成异氰酸酯单加合物作为溶剂增溶基团,聚异氰酸酯中仅保留一个官能度。
在一个实施方案中,本公开提供分散剂,其具有衍生自以下的片段:(1)一种或多种具有至少2个异氰酸酯基团的聚异氰酸酯,(2)具有异氰酸酯反应性官能部分的单官能化合物;以及(3)胺官能度为二或更多的聚胺。
在另一个实施方案中,分散剂可以从不含有机溶剂的反应获得:(1)一种或多种具有至少2个异氰酸酯基团的聚异氰酸酯,与(2)具有异氰酸酯反应性官能部分的单官能化合物反应以形成异氰酸酯单加合中间体。异氰酸酯单加合中间体随后与(3)胺官能度为二或更多的聚胺反应。
根据本文所述的分散剂组合物,组分(1)可以为具有至少2个异氰酸酯基团的聚异氰酸酯。在一个实施方案中,聚异氰酸酯包括脂肪族异氰酸酯、脂环族异氰酸酯、芳香族异氰酸酯、杂环异氰酸酯,及其混合物。在一些实施方案中,这类聚异氰酸酯的异氰酸酯基团的个数可以为2至8、2至5,或2至4。在其它实施方案中,异氰酸酯基团的平均数为2至5。具有两个异氰酸酯官能团的聚异氰酸酯的适合的实例为二异氰酸酯,例如甲苯二异氰酸酯(TDI,80/20)、异佛尔酮二异氰酸酯(IPDI)、六亚甲基二异氰酸酯(HDI)、二苯甲烷-4,4'-二异氰酸酯(4,4'-MDI)、二环己基甲烷-4,4'-二异氰酸酯(HMDI)、1,4-双(2-异氰酸根-2-基)苯(TXMDI)、三甲基六亚甲基二异氰酸酯(“TMDI”),或这些二异氰酸酯的混合物。在一个实施方案中,聚异氰酸酯是TDI、IPDI、HMDI,和其混合物。在一个实施方案中,聚异氰酸酯是TDI。在一个实施方案中,聚异氰酸酯包括HDI异氰脲酸酯三聚体,以及IPDI异氰脲酸酯三聚体。多官能团的实例为由二异氰酸酯和多元醇的加成产物获得的Desmodur L,和由双缩脲反应获得的Desmour N,由二异氰酸酯环化获得的Desmodur IL。
进一步根据本文中所述的分散剂组合物,组分(2)可以为具有异氰酸酯反应性官能部分的单官能化合物。在一个实施方案中,单官能化合物可以为具有350g/mole至5000g/mole的分子量的脂肪族化合物、脂环族化合物、芳香族化合物,及其组合,并且可以含有一种或多种醚键、酯键及其混合物。在一些实施方案中,这类单官能化合物的分子量可以为:550g/mole至3000g/mole;550g/mole至2000g/mole或550g/mole至1000g/mole。单官能化合物的实施方案的异氰酸酯反应性官能部分独立地选自羟基、氨基或亚氨基及其组合。
在一个实施方案中,单官能化合物可以为单羟基化合物。在一个实施方案中,单羟基化合物可以为线性的、支化的,及其混合物。在一些其它实施方案中,单羟基化合物可以为饱和的或不饱和的。在某些实施方案中,单羟基化合物为饱和的。
在某一实施方案中,单官能化合物包括聚(C2-4-环氧烷)化合物。可取的是聚(C2-4-环氧烷)化合物具有低分子量使得其有效地起到作为分散剂的增溶基团的作用。在一些实施方案中,最终与分散剂结构中的锚定部分相连的聚环氧烷链的数均分子量Mn为350g/mole至5000g/mole;或350g/mole至3000g/mole或350g/mole至2000g/mole。在一个实施方案中,聚(C2-4-环氧烷)化合物的数均分子量不超过5000g/mole。在另一个实施方案中,聚(C2-4-环氧烷)化合物的数均分子量不超过3000g/mole。在又一个实施方案中,聚(C2-4-环氧烷)化合物的数均分子量不超过2000g/mole。在这类实施方案中,聚(C2-4-环氧烷)化合物的数均分子量为至少350g/mole。
在另一个实施方案中,单官能化合物可以为聚酯低聚物。聚酯低聚物可以通过已知技术获得,诸如一种或多种二羧酸、乙二醇、酸酐、羟基羧酸以及可以应用于酯化反应的任何其它材料的缩聚反应。或者,诸如δ-戊内酯和/或ε-己内酯的相应内酯的开环聚合也是合适的选择。
在一个实施方案中,单官能化合物与组分(1)反应以形成异氰酸酯单加合中间体。在一个实施方案中,具有至少2个异氰酸酯基团的聚异氰酸酯具有式(1)的结构:
其中Q为脂族基,芳族基,芳烷基或者任选地被杂原子、酰胺基、酯基、氨基甲酸酯基、碳酸酯基、脲基或其组合一次或多次中断的脂族主链或芳族主链;X是直接键、亚烷基、亚烯基、亚炔基、亚芳基、亚环烷基、亚杂环烷基、亚杂芳基、环烷基-亚烷基、亚芳基-亚烷基、亚环烷基-亚芳基,亚杂环烷基-烷基,亚杂芳基-亚烷基;以及
r是2至8的整数。
在至少一个实施方案中,通式(2)的异氰酸酯单加合中间体是通过Y-Z形式的单官能化合物与组分(1)的反应形成的:
其中,化合物Y-Z的Z为亲核基团;Y为脂族基、脂环族基、芳族基或其组合,化合物Y-Z的分子量为350g/mole至5000g/mole或350g/mole至3000g/mole或350g/mole至2000g/mole,并且可以含有一种或多种醚键、酯键或其混合物;p为化合物Y-Z的当量数;r为聚异氰酸酯中NCO基团的当量数:
Q具有以上所提供的相同的含义;并且(r-p)为未反应的NCO基团的当量数。Y-Z形式的单官能化合物与组分(1)的反应可以由方案1表示:
方案1
在另一个实施方案中,Y-Z形式的单官能化合物与组分(1)反应以形成通式(3)的异氰酸酯单加合中间体产物:
其中(r-1)是与化合物Y-Z反应的NCO的当量数(每聚异氰酸酯分子),并且(r-1)为与组分(1)反应的Y-Z的当量数;Y、Z、Q、r和X都有如式(1)中所限定的相同的含义。Y-Z形式的单官能化合物与组分(1)的反应可以由方案2表示:
方案2
在至少一个优选的实施方案中,化合物Y-Z为单羟基化合物,Y-OH,其当与组分(1)反应时形成通式(3.1)的异氰酸酯单加合中间体产物:
其中(r-1)是与化合物Y-OH反应的NCO的当量数(每聚异氰酸酯分子);Y、Q、r和X都有如式(1)中所限定的相同的含义。单羟基化合物Y-OH与组分(1)的反应可以由方案3表示:
方案3
在式(2)和式(3)的异氰酸酯单加合中间体产物的一些优选实施方案中,Z是─O─、─NH─或─NR─,其中R可以为具有1至10个碳原子的烷基、环烷基、芳基或其组合。在式(1)的化合物的至少一个实施方案中,Q衍生自缩二脲(亚氨基二碳酸二酰胺)或1,3,5-三嗪-2,4,6-三酮或其组合。
进一步根据本文所述的分散剂组合物,组分(3)可以为胺官能度为二或更多的聚胺。在一个这样的实施方案中,聚胺包括聚(C2-6-亚烷基亚胺),例如聚乙烯亚胺(PEI)和对于C2化合物的聚乙烯胺、对于C3化合物的聚烯丙基胺。在一些实施方案中,聚胺可以为线性的或支化的。示例性的脂族线性聚胺包括伯胺基和仲胺基,诸如二亚乙基三胺(DETA)、三亚乙基四胺(TETA)、四亚乙基五胺(TEPA)、五亚乙基六胺(PEHA)、六亚乙基七胺(HEHA)和相似的高级类似物。示例性的脂族支化聚胺包括伯胺基、仲胺基和叔胺基并且其具有600至30000或1000至10000的聚胺的数均分子量Mn。示例性的聚乙烯亚胺包括线性聚乙烯亚胺或支化聚乙烯亚胺。市售聚乙烯亚胺以BASF的以及Nippon Shokubai的销售。
在一个实施方案中,分散剂组合物是水溶性的。
在一个实施方案中,分散剂组合物可以在不使用有机溶剂的条件下制备,从而在反应过程中将不会释放挥发性有机化合物。因此,在反应初期应当注意热累积现象。制备聚氨酯的常用催化剂可用于在热释放之后加速反应速率,如锡催化剂。例如,可以从NITTO KASEI获得二月桂酸二丁基锡、二乙酸二丁基锡和二乙酸二乙基锡。还可以应用铋催化剂,例如市售化合物,KING INDUSTRIES公司的K-系列产品或NITTO KASEI公司的系列产品。
异氰酸酯单加合中间体与组分(3)的反应是通过已知方法进行的。通常,脲键在这些过程中形成,反应通常不使用额外的催化剂和有机溶剂。在一些实施方案中,基于聚(C2-6-亚烷基亚胺)框架的分子结构将导致星状几何形状。作为增溶部分的异氰酸酯单加合中间体将在末端位置与锚定骨架相连。
分散过程有三个主要阶段,颜料润湿、颜料崩解以及颜料稳定。润湿过程,该过程将颜料表面状态从固/气表面转变至固/液介面。为了将颜料固体引入液体介质中,高剪切力是必需的。因此,通常使用分散剂以降低这些分散力并且从而将系统所需的总能量输入和分散时间都最小化。此外,分散剂还提供稳定机制以防止再团聚。已知的分散剂通常为表面活性物质,仅将其少量直接应用于固体或加入液体介质中。在颜料团聚体完全反絮凝之后分散介质均化,在分散操作之后可以发生再团聚的情况。这样,可能产生负面效果,如液体体系中粘度的增加、浮色和发花,或者油墨和涂料的光泽的损失。
本发明化合物用作有机或无机颜料或填料的润湿分散剂。它的用量为基于在油墨和涂料组合物中待分散固体的0.5wt%至50wt%。然而,在分散条件下对于高颜料表面的情况需要更大量的分散剂。
实施例
以下实施例进一步描述并展现在本发明范围内的示例性实施方案。提供实施例仅用于示例而并不被解释为作为对本发明的限制,因为在不背离本发明的主旨和范围的情况下,多种改变是可能的。
实施例1
1000mL三口反应烧瓶装配有温度计、回流冷凝器、加热套和机械搅拌器,将50.0份甲苯二异氰酸酯(TDI)放入反应容器中并在氮气和环境温度下搅拌。将287.0份聚(乙二醇)甲醚(DME-1000)通过滴液漏斗用1.5小时逐滴加入至反应器中。将反应混合物加热至70℃,并且根据DIN 53185通过滴定法监测NCO%的降低。当NCO%降至3.6%时,将9.9份二亚乙基三胺(DETA)用1小时逐滴加入。将混合物加热至85℃并且在该温度下再搅拌3小时。去掉热源。将520.4份水加入到热的混合物中。产物是固含量为40.3%的澄清淡黄色溶液。这是分散剂1。
实施例2
与实施例1相似,将50.0份甲苯二异氰酸酯(TDI)放入反应容器中并且在氮气和环境温度下搅拌。将287.0份聚(乙二醇)甲醚(DME-1000)通过滴液漏斗用1.5小时的时间逐滴加入至反应器中。将反应混合物加热至70℃,并且通过滴定法监测NCO%的降低。当NCO%降至3.6%时,将10.5份三亚乙基四胺(TETA)用1小时的时间逐滴加入。将混合物加热至85℃并且在该温度下再搅拌3小时。去掉热源。将521.3份水加入到热的混合物中。产物是固含量为39.7%的澄清淡黄色溶液。这是分散剂2。
实施例3
与实施例1相似,将50.0份甲苯二异氰酸酯(TDI)放入反应容器中并且在氮气和环境温度下搅拌。将287.0份聚(乙二醇)甲醚(DME-1000)通过滴液漏斗用1.5小时的时间逐滴加入至反应器中。将反应混合物加热至70℃,并且通过滴定法监测NCO%的降低。当NCO%降至3.6%时,将10.9份四亚乙基五胺(TEPA)用1小时逐滴加入。将混合物加热至85℃并且在该温度下再搅拌3小时。去掉热源。将521.9份水加入到热的混合物中。产物是固含量为40.4%的澄清淡黄色溶液。这是分散剂3。
实施例4
将60.0份异佛尔酮二异氰酸酯(IPDI)以及0.02份NEOSTANNU-600(获得自NITTO KASEI CO.,LTD)放入反应容器中,并且在氮气和环境温度下搅拌。将269.9份聚(乙二醇)甲醚(DME-1000)通过滴液漏斗用1.5小时的时间逐滴加入至反应器中。将反应混合物加热至70℃,并且通过滴定法监测NCO%的降低。当NCO%降至3.4%时,将9.3份二亚乙基三胺(DETA)用1小时逐滴加入。将混合物加热至85℃并且在该温度下再搅拌3小时。去掉热源。将508.8份水加入到热的混合物中。产物是固含量为40.2%的澄清淡黄色溶液。这是分散剂4。
实施例5
与实施例4相似,将60.0份异佛尔酮二异氰酸酯(IPDI)和0.02份NEOSTANN U-600放入反应容器中,并且在氮气和环境温度下搅拌。将269.9份聚(乙二醇)甲醚(DME-1000)通过滴液漏斗用1.5小时的时间逐滴加入至反应器中。将反应混合物加热至70℃,并且通过滴定法监测NCO%的降低。当NCO%降至3.4%时,将9.9份三亚乙基四胺(TETA)用1小时的时间逐滴加入。将混合物加热至85℃并且在该温度下再搅拌3小时。去掉热源。将509.7份水加入到热的混合物中。产物是固含量为40.0%的澄清淡黄色溶液。这是分散剂5。
实施例6
与实施例4相似,将60.0份异佛尔酮二异氰酸酯(IPDI)和0.02份NEOSTANN U-600放入反应容器中,并且在氮气和环境温度下搅拌。将269.9份聚(乙二醇)甲醚(DME-1000)通过滴液漏斗用1.5小时的时间逐滴加入至反应器中。将反应混合物加热至70℃,并且通过滴定法监测NCO%的降低。当NCO%降至3.4%时,将10.2份四亚乙基五胺(TEPA)用1小时逐滴加入。将混合物加热至85℃并且在该温度下再搅拌3小时。去掉热源。将510.2份水加入到热的混合物中。产物是固含量为39.6%的澄清淡黄色溶液。这是分散剂6。
实施例7
将100份异佛尔酮二异氰酸酯(IPDI)和0.02份NEOSTANN U-600放入反应容器中,并且在氮气和环境温度下搅拌。将247.4份聚(乙二醇)甲醚(MPEG-550)通过滴液漏斗用1.5小时逐滴加入至反应器中。将反应混合物加热至70℃,并且通过滴定法监测NCO%的降低。当NCO%降至5.4%时,将15.5份二亚乙基三胺(DETA)用1小时逐滴加入。将混合物加热至85℃并且在该温度下再搅拌3小时。去掉热源。将544.4份水加入到热的混合物中。产物是固含量为40.1%的澄清淡黄色溶液。这是分散剂7。
实施例8
与实施例7相似,将100份异佛尔酮二异氰酸酯(IPDI)和0.02份NEOSTANN U-600放入反应容器中,并且在氮气和环境温度下搅拌。将247.4份聚(乙二醇)甲醚(MPEG-550)通过滴液漏斗用1.5小时的时间逐滴加入至反应器中。将反应混合物加热至70℃,并且通过滴定法监测NCO%的降低。当NCO%降至5.4%时,将16.5份三亚乙基四胺(TETA)用1小时的时间逐滴加入。将混合物加热至85℃并且在该温度下再搅拌3小时。去掉热源。将545.9份水加入到热的混合物中。产物是固含量为40.5%的澄清淡黄色溶液。这是分散剂8。
实施例9
与实施例7相似,将100份异佛尔酮二异氰酸酯(IPDI)和0.02份NEOSTANN U-600放入反应容器中,并且在氮气和环境温度下搅拌。将247.4份聚(乙二醇)甲醚(MPEG-550)通过滴液漏斗用1.5小时的时间逐滴加入反应器中。将反应混合物加热至70℃,并且根据DIN 53185通过滴定法监测NCO%的降低。当NCO%降至5.4%时,将17.0份四亚乙基五胺(TEPA)用1小时的时间逐滴加入。将混合物加热至85℃并且在该温度下再搅拌3小时。去掉热源。将546.6份水加入到热的混合物中。产物是固含量为40.2%的澄清淡黄色溶液。这是分散剂9。
实施例10
将60份Desmodur N 100(Bayer,官能度=3.8)和0.02份NEOSTANNU-600放入反应容器中,并且在氮气和环境温度下搅拌。将231.66份聚(乙二醇)甲醚(MPEG-1000)通过滴液漏斗用1.5小时的时间逐滴加入至反应器中。将反应混合物加热至70℃,并且根据DIN 53185通过滴定法监测NCO%的降低。当NCO%降至1.19%时,将2.84份二亚乙基三胺(DETA)用1小时的时间逐滴加入。将混合物加热至85℃并且在该温度下再搅拌3小时。去掉热源。将441.78份水加入到热的混合物中。产物是固含量为40.0%的澄清淡黄色溶液。这是分散剂10。
实施例11
将60份由季戊四醇和六亚甲基二异氰酸酯制备的聚异氰酸酯(第4,670,068号美国专利实施例1,具有4.5的官能度)和0.02份NEOSTANN U-600放入反应容器中,并且在氮气和环境温度下搅拌。将215.4份聚(乙二醇)甲醚(MPEG-1000)通过滴液漏斗用1.5小时的时间逐滴加入至反应器中。将反应混合物加热至70℃,并且根据DIN53185通过滴定法监测NCO%的降低。当NCO%降至0.93%时,将2.1份二亚乙基三胺(DETA)用1小时的时间逐滴加入。将混合物加热至85℃并且在该温度下再搅拌3小时。去掉热源。将416.28份水加入到热的混合物中。产物是固含量为40.0%的澄清淡黄色溶液。这是分散剂11。
对照实施例
FX 365为购自Elementis Specialties的润湿剂
FX 600为购自Elementis Specialties的分散剂
性能评估
为了揭示实施例1-9中所述的分散剂的性能,通过将分散剂以表1中的浓度加入至150mL玻璃瓶中来制备不含粘合剂的颜料浓缩物。测量润湿效果和粘度。
表1
DF 665为购自Elementis Specialties的消泡剂
DF 7620为购自Elementis Specialties的消泡剂
将混合物与200份直径为2mm的锆(zicronium)珠合并。还使用了Carbon Black MA 100和Heliogen Blue D 7079。用负载有25%的颜料的黑色颜料浓缩物以及负载有30%的颜料的蓝色颜料浓缩物制备水性分散剂。
将玻璃瓶置于Scandex分散器中并且将内含物通过振荡摇晃研磨直至粒径小于5μm。用细度计测定细度。在剪切速率范围内用锥板几何结构在Brookfield粘度计上测量分散液的粘度。细度和粘度数据在表2和表3中示出。
表2
表3
在不背离本公开的主旨或本质属性的情况下,本公开可以以其它具体形式实施。因此,应参考所附权利要求,而不是前述说明书来表示本公开的范围。尽管前述的描述涉及本公开的优选实施方案,但是应当注意的是其它的改变和修改对于本领域技术人员而言将是显而易见的,并且可以在不背离本公开的精神或范围的情况下做出。
Claims (15)
1.分散剂,其包括衍生自以下的片段:
(1)一种或多种具有至少2个异氰酸酯基团的聚异氰酸酯,
(2)具有异氰酸酯反应性官能部分的单官能化合物;以及
(3)胺官能度为二或更多的聚胺。
2.根据权利要求1所述的分散剂,其中50%-90%当量的所述聚异氰酸酯的异氰酸酯基团与所述单官能化合物结合,并且10%-50%当量的所述异氰酸酯基团与所述聚胺结合。
3.根据权利要求1和2中任一项所述的分散剂,其中所述单官能化合物独立地选自脂肪族化合物、脂环族化合物和芳香族化合物,及其组合,所述单官能化合物具有350至5000的分子量,并且所述单官能化合物含有至少一个独立地选自以下的基团:-O-或-COO-及其组合。
4.根据权利要求3所述的分散剂,其中所述异氰酸酯反应性官能部分独立地选自羟基、胺或亚胺及其组合。
5.根据权利要求4所述的分散剂,其中所述单官能化合物独立地选自含有60%-99%的环氧乙烷基团的聚(C2-4-环氧烷)、聚酯低聚物,及其组合。
6.根据权利要求5所述的分散剂,其中所述聚酯低聚物含有衍生自二羧酸和乙二醇的片段。
7.根据权利要求3至6中任一项所述的分散剂,其中所述聚异氰酸酯是二异氰酸酯,其独立地选自甲苯二异氰酸酯、异佛尔酮二异氰酸酯(IPDI)、六亚甲基二异氰酸酯、二苯甲烷-4,4'-二异氰酸酯、二环己基甲烷-4,4'-二异氰酸酯、1,4-双(2-异氰酸根-2-基)苯、三甲基六亚甲基二异氰酸酯,或这些二异氰酸酯的混合物。
8.根据权利要求3至6中任一项所述的分散剂,其中所述聚异氰酸酯独立地选自异氰酸酯加合物、异氰酸酯缩二脲、异氰酸酯异氰脲酸酯或这类聚异氰酸酯的混合物。
9.根据权利要求7或8中任一项所述的分散剂,其中所述聚异氰酸酯独立地选自甲苯二异氰酸酯和三羟甲基丙烷加合物、六亚甲基二异氰酸酯缩二脲三聚体、六亚甲基二异氰酸酯异氰脲酸酯三聚体、异佛尔酮二异氰酸酯异氰脲酸酯三聚体、六亚甲基二异氰酸酯异氰脲酸酯三聚体,和异佛尔酮二异氰酸酯异氰脲酸酯三聚体。
10.根据权利要求3至9中任一项所述的分散剂,其中所述聚胺独立地选自聚乙烯亚胺(PEI)、聚乙烯胺、聚烯丙基胺低聚物、乙烯亚胺低聚物,及其组合。
11.根据权利要求10所述的分散剂,其中所述聚胺独立地选自二亚乙基三胺(DETA)、三亚乙基四胺(TETA)、四亚乙基五胺(TEPA)、五亚乙基六胺(PEHA),六亚乙基七胺(HEHA)及其组合。
12.根据权利要求3至11中任一项所述的分散剂,其中所述分散剂是水溶性的。
13.根据权利要求1至12中任一项所述的分散剂的制备方法,其中所述聚异氰酸酯与所述单官能化合物反应以形成异氰酸酯单加合中间体。
14.根据权利要求13所述的分散剂的制备方法,其中所述异氰酸酯单加合中间体与所述聚胺反应以形成所述分散剂。
15.分散体,其包含(i)独立地选自有机颜料固体、无机颜料固体及其组合的颜料,(ii)极性液体介质,以及(iii)根据权利要求3至12中任一项所述的分散剂。
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CN112724349A (zh) * | 2019-10-28 | 2021-04-30 | 立邦涂料(中国)有限公司 | 新型聚合物及其用途 |
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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