JP5518889B2 - レオロジー効果を有する尿素ウレタンを有機塩中で製造する方法 - Google Patents
レオロジー効果を有する尿素ウレタンを有機塩中で製造する方法 Download PDFInfo
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- JP5518889B2 JP5518889B2 JP2011537867A JP2011537867A JP5518889B2 JP 5518889 B2 JP5518889 B2 JP 5518889B2 JP 2011537867 A JP2011537867 A JP 2011537867A JP 2011537867 A JP2011537867 A JP 2011537867A JP 5518889 B2 JP5518889 B2 JP 5518889B2
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- ion
- carbon atoms
- alkyl group
- tolylene diisocyanate
- Prior art date
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- 238000000034 method Methods 0.000 title claims description 34
- OYQYHJRSHHYEIG-UHFFFAOYSA-N ethyl carbamate;urea Chemical compound NC(N)=O.CCOC(N)=O OYQYHJRSHHYEIG-UHFFFAOYSA-N 0.000 title claims description 32
- 230000008569 process Effects 0.000 title claims description 8
- 150000003839 salts Chemical class 0.000 title description 7
- 230000000694 effects Effects 0.000 title description 3
- -1 tetrafluoroborate ion Chemical class 0.000 claims description 56
- 239000002608 ionic liquid Substances 0.000 claims description 36
- 125000004432 carbon atom Chemical group C* 0.000 claims description 25
- 239000000203 mixture Substances 0.000 claims description 24
- 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 19
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- 239000013008 thixotropic agent Substances 0.000 claims description 17
- 125000003118 aryl group Chemical group 0.000 claims description 16
- 150000004985 diamines Chemical class 0.000 claims description 15
- 239000011248 coating agent Substances 0.000 claims description 13
- 238000000576 coating method Methods 0.000 claims description 13
- 125000005843 halogen group Chemical group 0.000 claims description 13
- 125000001931 aliphatic group Chemical group 0.000 claims description 8
- 150000001450 anions Chemical class 0.000 claims description 8
- 150000001768 cations Chemical class 0.000 claims description 7
- 125000001072 heteroaryl group Chemical group 0.000 claims description 7
- 229940085991 phosphate ion Drugs 0.000 claims description 7
- 239000011541 reaction mixture Substances 0.000 claims description 7
- 239000007787 solid Substances 0.000 claims description 7
- 150000001298 alcohols Chemical class 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 239000000463 material Substances 0.000 claims description 6
- 150000002500 ions Chemical class 0.000 claims description 5
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- 125000002723 alicyclic group Chemical group 0.000 claims description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- 239000007788 liquid Substances 0.000 claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 3
- 229920006395 saturated elastomer Polymers 0.000 claims description 3
- 229910016467 AlCl 4 Inorganic materials 0.000 claims description 2
- 229910017008 AsF 6 Inorganic materials 0.000 claims description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 2
- 229910021591 Copper(I) chloride Inorganic materials 0.000 claims description 2
- 229910018286 SbF 6 Inorganic materials 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000003963 dichloro group Chemical group Cl* 0.000 claims description 2
- 125000000524 functional group Chemical group 0.000 claims description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 230000009974 thixotropic effect Effects 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 239000002904 solvent Substances 0.000 description 13
- 239000000047 product Substances 0.000 description 10
- 238000003860 storage Methods 0.000 description 10
- 239000011230 binding agent Substances 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 8
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 229910003002 lithium salt Inorganic materials 0.000 description 6
- 159000000002 lithium salts Chemical class 0.000 description 6
- 239000003973 paint Substances 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- FDLQZKYLHJJBHD-UHFFFAOYSA-N [3-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=CC(CN)=C1 FDLQZKYLHJJBHD-UHFFFAOYSA-N 0.000 description 4
- 230000007797 corrosion Effects 0.000 description 4
- 238000005260 corrosion Methods 0.000 description 4
- 150000004820 halides Chemical class 0.000 description 4
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 4
- 238000000518 rheometry Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 239000000010 aprotic solvent Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000004202 carbamide Substances 0.000 description 3
- 238000007796 conventional method Methods 0.000 description 3
- 239000012948 isocyanate Substances 0.000 description 3
- 229910052751 metal Chemical class 0.000 description 3
- 239000002184 metal Chemical class 0.000 description 3
- 239000000049 pigment Substances 0.000 description 3
- 239000002002 slurry Substances 0.000 description 3
- 239000012855 volatile organic compound Substances 0.000 description 3
- VRFOKYHDLYBVAL-UHFFFAOYSA-M 1-ethyl-3-methylimidazol-3-ium;ethyl sulfate Chemical compound CCOS([O-])(=O)=O.CCN1C=C[N+](C)=C1 VRFOKYHDLYBVAL-UHFFFAOYSA-M 0.000 description 2
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical group CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical group OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 150000008051 alkyl sulfates Chemical class 0.000 description 2
- 230000029936 alkylation Effects 0.000 description 2
- 238000005804 alkylation reaction Methods 0.000 description 2
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 125000005442 diisocyanate group Chemical group 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 150000002513 isocyanates Chemical class 0.000 description 2
- 239000012263 liquid product Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 2
- 238000004062 sedimentation Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 125000000542 sulfonic acid group Chemical group 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 2
- 238000011179 visual inspection Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 1
- JXNPEDYJTDQORS-HZJYTTRNSA-N (9Z,12Z)-octadecadien-1-ol Chemical compound CCCCC\C=C/C\C=C/CCCCCCCCO JXNPEDYJTDQORS-HZJYTTRNSA-N 0.000 description 1
- PWGJDPKCLMLPJW-UHFFFAOYSA-N 1,8-diaminooctane Chemical compound NCCCCCCCCN PWGJDPKCLMLPJW-UHFFFAOYSA-N 0.000 description 1
- XUJLWPFSUCHPQL-UHFFFAOYSA-N 11-methyldodecan-1-ol Chemical compound CC(C)CCCCCCCCCCO XUJLWPFSUCHPQL-UHFFFAOYSA-N 0.000 description 1
- DDHUNHGZUHZNKB-UHFFFAOYSA-N 2,2-dimethylpropane-1,3-diamine Chemical compound NCC(C)(C)CN DDHUNHGZUHZNKB-UHFFFAOYSA-N 0.000 description 1
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
- IGSBHTZEJMPDSZ-UHFFFAOYSA-N 4-[(4-amino-3-methylcyclohexyl)methyl]-2-methylcyclohexan-1-amine Chemical compound C1CC(N)C(C)CC1CC1CC(C)C(N)CC1 IGSBHTZEJMPDSZ-UHFFFAOYSA-N 0.000 description 1
- DZIHTWJGPDVSGE-UHFFFAOYSA-N 4-[(4-aminocyclohexyl)methyl]cyclohexan-1-amine Chemical compound C1CC(N)CCC1CC1CCC(N)CC1 DZIHTWJGPDVSGE-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- RAXXELZNTBOGNW-UHFFFAOYSA-O Imidazolium Chemical compound C1=C[NH+]=CN1 RAXXELZNTBOGNW-UHFFFAOYSA-O 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical group CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- 239000005922 Phosphane Substances 0.000 description 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 1
- 229920001944 Plastisol Polymers 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- RWRDLPDLKQPQOW-UHFFFAOYSA-O Pyrrolidinium ion Chemical compound C1CC[NH2+]C1 RWRDLPDLKQPQOW-UHFFFAOYSA-O 0.000 description 1
- AWMVMTVKBNGEAK-UHFFFAOYSA-N Styrene oxide Chemical group C1OC1C1=CC=CC=C1 AWMVMTVKBNGEAK-UHFFFAOYSA-N 0.000 description 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-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
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 230000002152 alkylating effect Effects 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical class O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical group OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- 229940063013 borate ion Drugs 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Chemical group 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- XLJKHNWPARRRJB-UHFFFAOYSA-N cobalt(2+) Chemical compound [Co+2] XLJKHNWPARRRJB-UHFFFAOYSA-N 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 1
- JMLPVHXESHXUSV-UHFFFAOYSA-N dodecane-1,1-diamine Chemical compound CCCCCCCCCCCC(N)N JMLPVHXESHXUSV-UHFFFAOYSA-N 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 238000001879 gelation Methods 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 238000007037 hydroformylation reaction Methods 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- JXNPEDYJTDQORS-UHFFFAOYSA-N linoleyl alcohol Natural products CCCCCC=CCC=CCCCCCCCCO JXNPEDYJTDQORS-UHFFFAOYSA-N 0.000 description 1
- 150000002642 lithium compounds Chemical class 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 229940055577 oleyl alcohol Drugs 0.000 description 1
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Chemical compound [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- CTYRPMDGLDAWRQ-UHFFFAOYSA-N phenyl hydrogen sulfate Chemical compound OS(=O)(=O)OC1=CC=CC=C1 CTYRPMDGLDAWRQ-UHFFFAOYSA-N 0.000 description 1
- NIXKBAZVOQAHGC-UHFFFAOYSA-N phenylmethanesulfonic acid Chemical group OS(=O)(=O)CC1=CC=CC=C1 NIXKBAZVOQAHGC-UHFFFAOYSA-N 0.000 description 1
- 229910000064 phosphane Inorganic materials 0.000 description 1
- 150000004714 phosphonium salts Chemical class 0.000 description 1
- 239000004999 plastisol Substances 0.000 description 1
- 238000007747 plating Methods 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229920000728 polyester Chemical group 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000003405 preventing effect Effects 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 150000003138 primary alcohols Chemical class 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 1
- 238000005956 quaternization reaction Methods 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- YAYGSLOSTXKUBW-UHFFFAOYSA-N ruthenium(2+) Chemical compound [Ru+2] YAYGSLOSTXKUBW-UHFFFAOYSA-N 0.000 description 1
- 239000011833 salt mixture Substances 0.000 description 1
- 238000010517 secondary reaction Methods 0.000 description 1
- 239000011265 semifinished product Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 125000002827 triflate group Chemical group FC(S(=O)(=O)O*)(F)F 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical group OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- 229920006337 unsaturated polyester resin Polymers 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- 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
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C273/00—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C273/18—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of substituted ureas
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C273/00—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
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Description
トリレンジイソシアネートの量は、好ましくは1.5〜5.0倍モル過剰、より好ましくは2.0〜4.0倍モル過剰である。
[A]n +[Y]n-
により表される。式中、nは1又は2である。アニオン[Y]n-は、テトラフルオロホウ酸イオン[BF4]-、テトラクロロホウ酸イオン[BCl4]-、リン酸イオン[PO4]3-、アルキルリン酸イオン[ROPO3]2-/[ROR'OPO2]-、ヘキサフルオロリン酸イオン[PF6]-、ヘキサフルオロアンチモン酸イオン[SbF6]-、ヘキサフルオロヒ酸イオン[AsF6]-、テトラクロロアルミン酸イオン[AlCl4]-、トリクロロ亜鉛酸イオン[ZnCl3]-、ジクロロ銅酸イオン[CuCl2]-、硫酸イオン[SO4]2-、アルキル硫酸イオン[R'−SO4]-、炭酸イオン[CO3]2-、フルオロスルホン酸イオン、[R'−COO]-、[R'−SO3]-、及び[(R'−SO2)2N]-からなる群から選ばれる。ここで、R及びR'はそれぞれ独立に炭素原子数1〜12の直鎖状又は分岐状の脂肪族又は脂環式アルキル基、C5〜C18アリール基、C5〜C18アリール−C1〜C6アルキル基、或いはC1〜C6アルキル−C5〜C18アリール基であり、これらの水素原子の全部又は一部がハロゲン原子で置換されていてもよい。上述のとおり、アニオン[Y]n-は、[F]-、[Cl]-、[Br]-、[I]-等のハロゲン化物イオンであってもよいが、この場合は、チキソトロピック剤の用途によっては上記の問題(腐食)が付随することになる。
中でも、アルキル硫酸イオン、トシル酸イオン、及び酢酸イオンが特に好ましい。
以下、典型的な実施形態を示し、本発明の方法の本質的な特徴を説明する。
15.9gのLiCl及び68gのm−キシリレンジアミンを、403gのN−メチルピロリドンに80℃で溶解する。その後、1時間以内に320gの混合物Aを計量する。添加完了後に混合物をさらに30分間攪拌し、室温に冷却する。このようにして得られる尿素ウレタン溶液は50%の固形分を有する。
68gのm−キシリレンジアミンと690gのエチル硫酸1−エチル−3−メチルイミダゾリウムとの混合物を調製し、60℃に加熱する。その後、1時間以内に472gの混合物Aを計量する。添加完了後に混合物をさらに30分間攪拌し、室温に冷却する。このようにして得られる尿素ウレタン溶液は50%の固形分を有する。透明で均質な液状生成物が得られる。
68gのm−キシリレンジアミンと238gのエチル硫酸1−エチル−3−メチルイミダゾリウムとの混合物を調製し、60℃に加熱する。その後、1時間以内に472gの混合物Aを計量する。添加完了後に混合物をさらに30分間攪拌し、室温に冷却する。このようにして得られる尿素ウレタン溶液は70%の固形分を有する。透明で均質な液状生成物が得られる。
目視検査によって、試料の外観を時間の関数として評価する。結果を表3にまとめる。
各例で調製した5mgの尿素ウレタン溶液試料を20mlヘッドスペースバイアルに入れ、気密に封をする。このバイアル(高さ7cm、直径2cmのガラス管)を、100℃で1時間平衡化し、ガスクロマトグラフィーで分析する。保持時間の経過と共に溶出したC6〜C16のピークはいずれも検討する。以下の結果が得られる。
本発明の尿素ウレタン溶液の沈降防止効果を調べるために、顔料スラリーを調製し、3週間保管した後、沈降挙動を分析した。
顔料スラリーを調製するために、まず水、ブチルグリコール、及びディスパービック(Disperbyk)192の混合物を調製する。この混合物を攪拌下でメルク社製顔料イリオジン(Iriodin)9303ロイヤルゴールドWRIIに加える。その後、ディスパーマット(Dispermat)を用いて、せん断率2m/秒で2分間、再び攪拌下で本発明の尿素ウレタン溶液を再度加える。
使用した添加剤の腐食作用を評価するために、表5に示す塗料をスズめっき缶に入れて密封した。6ヶ月後に缶を開け、缶の内壁の外観を目視検査により評価した。結果を表7に示す。
Claims (10)
- チキソトロピック剤として有効な尿素ウレタンを含有する溶液を製造する方法であって、一般構造R−OH[式中、Rは炭素原子数4〜22のn−アルキル基又はi−アルキル基、炭素原子数3〜18のアルケニル基、シクロアルキル基又はアラルキル基、或いは式CmH2m+1(O−CnH2n)x−、CmH2m+1(OOC−CvH2v)x−、又はZ−C6H4(O−CnH2n)x−の基であり、ここでm=1〜22、n=2〜4、x=1〜15、v=4又は5であり、Zは炭素原子数1〜12のアルキル基である]で表されるモノヒドロキシ化合物を1.5〜5倍過剰のトリレンジイソシアネートと反応させる工程、反応混合物から未反応の前記トリレンジイソシアネートを除去する工程、並びに得られたモノイソシアネート付加物を式H2N−R'−NH2[式中、R'は、
CoH2o(o=2〜12)、
(CpH2p−O)q−CpH2p(p=2〜4、q=1〜25)、
- まず少なくとも2種の構造的に異なるアルコール「R−OH」を混合し、その後1.5〜5倍過剰のトリレンジイソシアネートと反応させ、反応混合物から未反応の前記トリレンジイソシアネートを除去し、このようにして得られた複数の構造的に異なるモノイソシアネート付加物の混合物をイオン性液体中で前記ジアミンと反応させて、前記尿素ウレタンを形成させることを特徴とする請求項1に記載の方法。
- まず少なくとも2種の構造的に異なるアルコール「R−OH」をそれぞれ別々に1.5〜5倍過剰のトリレンジイソシアネートと反応させ、反応混合物から未反応の前記トリレンジイソシアネートを除去し、このようにして得られた複数の構造的に異なるモノイソシアネート付加物を互いに混合し、この前記複数の構造的に異なるモノイソシアネート付加物の混合物をイオン性液体中で前記ジアミンと反応させて、前記尿素ウレタンを形成させることを特徴とする請求項1に記載の方法。
- 5〜80重量%の固形分を有する溶液を製造することを特徴とする請求項1〜3のいずれかに記載の方法。
- 前記トリレンジイソシアネートの量が2〜4倍モル過剰であることを特徴とする請求項1〜4のいずれかに記載の方法。
- 50〜100重量%の2,4−異性体分率を有するトリレンジイソシアネート異性体混合物を使用することを特徴とする請求項1〜5のいずれかに記載の方法。
- 前記イオン性液体が25℃で液状であることを特徴とする請求項1〜6のいずれかに記載の方法。
- 前記イオン性液体が一般式(I):
[A]n +[Y]n-
[式中、nは1又は2であり、アニオン[Y]n-はテトラフルオロホウ酸イオン[BF4]-、テトラクロロホウ酸イオン[BCl4]-、リン酸イオン[PO4]3-、アルキルリン酸イオン[ROPO3]2-/[ROR'OPO2]-、ヘキサフルオロリン酸イオン[PF6]-、ヘキサフルオロアンチモン酸イオン[SbF6]-、ヘキサフルオロヒ酸イオン[AsF6]-、テトラクロロアルミン酸イオン[AlCl4]-、トリクロロ亜鉛酸イオン[ZnCl3]-、ジクロロ銅酸イオン[CuCl2]-、硫酸イオン[SO4]2-、アルキル硫酸イオン[R'−SO4]-、炭酸イオン[CO3]2-、フルオロスルホン酸イオン、[R'−COO]-、[R'−SO3]-、及び[(R'−SO2)2N]-からなる群から選ばれ、ここでR及びR'はそれぞれ独立に炭素原子数1〜12の直鎖状又は分岐状の脂肪族又は脂環式アルキル基、C5〜C18アリール基、C5〜C18アリール−C1〜C6アルキル基、或いはC1〜C6アルキル−C5〜C18アリール基であり、これらの水素原子の全部又は一部がハロゲン原子で置換されていてもよく、カチオン[A]+は
- 請求項1〜8のいずれかに記載の方法によって得られる前記溶液を、被覆材料にチキソトロピー性を付与するために使用する方法。
- 請求項1で定義した前記尿素ウレタンをイオン性液体中に含む溶液。
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DE2822908C2 (de) | 1978-05-26 | 1980-03-20 | Byk-Mallinckrodt Chemische Produkte Gmbh, 4230 Wesel | Thixotropiemittel für Überzugsmittel |
NL8500476A (nl) | 1985-02-20 | 1986-09-16 | Akzo Nv | Thixotrope bekledingssamenstelling. |
GB9425105D0 (en) | 1994-12-13 | 1995-02-08 | Bp Chem Int Ltd | Ionic liquids |
FR2741875B1 (fr) | 1995-11-30 | 1998-01-02 | Inst Francais Du Petrole | Procede pour l'hydroformylation des composes olefiniques |
US6617468B2 (en) * | 2000-08-16 | 2003-09-09 | Byk-Chemie Gmbh | Rheologically active urea urethane compounds |
DE10039837C2 (de) * | 2000-08-16 | 2003-03-20 | Byk Chemie Gmbh | Verfahren zur Herstellung einer lagerstabilen, rheologisch wirksamen Harnstoffurethan-Lösung mit breiter Verträglichkeit |
EP1182197A1 (de) | 2000-08-24 | 2002-02-27 | Solvent Innovation GmbH | Einstufiges Verfahren zur Darstellung ionischer Flüssigkeiten |
EP1399487A4 (en) * | 2001-03-30 | 2005-08-17 | Uab Research Foundation | PREPARATION OF POLYMERS IN ROOM TEMPERATURE LIQUID IONIC LIQUIDS |
DE102004053662A1 (de) * | 2004-11-03 | 2006-05-04 | Basf Ag | Verfahren zur Herstellung von Polyisocyanaten |
JP2006249166A (ja) * | 2005-03-09 | 2006-09-21 | Nippon Synthetic Chem Ind Co Ltd:The | 芳香族ポリイミドの製造方法 |
JP2006316041A (ja) * | 2005-04-14 | 2006-11-24 | Nippon Synthetic Chem Ind Co Ltd:The | 合成反応方法 |
KR100843594B1 (ko) | 2005-09-07 | 2008-07-03 | 주식회사 엘지화학 | 액상 산화 반응을 이용한 알데히드 화합물로부터의유기산의 제조 방법 |
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2008
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2009
- 2009-11-11 JP JP2011537867A patent/JP5518889B2/ja active Active
- 2009-11-11 WO PCT/EP2009/008043 patent/WO2010063358A1/de active Application Filing
- 2009-11-11 US US13/130,349 patent/US8956452B2/en active Active
- 2009-11-11 EP EP09767940A patent/EP2370489B1/de active Active
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US8956452B2 (en) | 2015-02-17 |
US20110265691A1 (en) | 2011-11-03 |
JP2012510434A (ja) | 2012-05-10 |
EP2370489B1 (de) | 2013-01-02 |
WO2010063358A1 (de) | 2010-06-10 |
DE102008059702A1 (de) | 2010-06-02 |
EP2370489A1 (de) | 2011-10-05 |
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