JP2023507360A - 貯蔵安定性ポリイソシアネート組成物及び調製方法 - Google Patents
貯蔵安定性ポリイソシアネート組成物及び調製方法 Download PDFInfo
- Publication number
- JP2023507360A JP2023507360A JP2022536899A JP2022536899A JP2023507360A JP 2023507360 A JP2023507360 A JP 2023507360A JP 2022536899 A JP2022536899 A JP 2022536899A JP 2022536899 A JP2022536899 A JP 2022536899A JP 2023507360 A JP2023507360 A JP 2023507360A
- Authority
- JP
- Japan
- Prior art keywords
- polyisocyanate composition
- storage
- diisocyanate
- groups
- group
- 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
Links
- 239000005056 polyisocyanate Substances 0.000 title claims abstract description 56
- 229920001228 polyisocyanate Polymers 0.000 title claims abstract description 56
- 239000000203 mixture Substances 0.000 title claims abstract description 44
- 238000000034 method Methods 0.000 title claims abstract description 32
- 238000003860 storage Methods 0.000 title claims abstract description 18
- 238000002360 preparation method Methods 0.000 title abstract description 5
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims abstract description 40
- PCHXZXKMYCGVFA-UHFFFAOYSA-N 1,3-diazetidine-2,4-dione Chemical group O=C1NC(=O)N1 PCHXZXKMYCGVFA-UHFFFAOYSA-N 0.000 claims abstract description 33
- 125000005442 diisocyanate group Chemical group 0.000 claims abstract description 19
- AVWRKZWQTYIKIY-UHFFFAOYSA-N urea-1-carboxylic acid Chemical group NC(=O)NC(O)=O AVWRKZWQTYIKIY-UHFFFAOYSA-N 0.000 claims abstract description 16
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical group OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 claims abstract description 14
- -1 alcohol compound Chemical class 0.000 claims abstract description 11
- 238000006243 chemical reaction Methods 0.000 claims description 44
- 239000003054 catalyst Substances 0.000 claims description 27
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 claims description 27
- 239000005057 Hexamethylene diisocyanate Substances 0.000 claims description 26
- XYFCBTPGUUZFHI-UHFFFAOYSA-N phosphine group Chemical group P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 26
- 230000035484 reaction time Effects 0.000 claims description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 15
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims description 13
- 150000001875 compounds Chemical class 0.000 claims description 11
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 9
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 6
- RWLALWYNXFYRGW-UHFFFAOYSA-N 2-Ethyl-1,3-hexanediol Chemical compound CCCC(O)C(CC)CO RWLALWYNXFYRGW-UHFFFAOYSA-N 0.000 claims description 5
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 claims description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 4
- 230000001476 alcoholic effect Effects 0.000 claims description 4
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 claims description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 4
- NMRPBPVERJPACX-UHFFFAOYSA-N (3S)-octan-3-ol Natural products CCCCCC(O)CC NMRPBPVERJPACX-UHFFFAOYSA-N 0.000 claims description 2
- LTOVZUHVYHATET-UHFFFAOYSA-N 1,2-diisocyanatoethylcyclohexane Chemical compound O=C=NCC(N=C=O)C1CCCCC1 LTOVZUHVYHATET-UHFFFAOYSA-N 0.000 claims description 2
- QGLRLXLDMZCFBP-UHFFFAOYSA-N 1,6-diisocyanato-2,4,4-trimethylhexane Chemical compound O=C=NCC(C)CC(C)(C)CCN=C=O QGLRLXLDMZCFBP-UHFFFAOYSA-N 0.000 claims description 2
- WOFPPJOZXUTRAU-UHFFFAOYSA-N 2-Ethyl-1-hexanol Natural products CCCCC(O)CCC WOFPPJOZXUTRAU-UHFFFAOYSA-N 0.000 claims description 2
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 claims description 2
- KXBFLNPZHXDQLV-UHFFFAOYSA-N [cyclohexyl(diisocyanato)methyl]cyclohexane Chemical compound C1CCCCC1C(N=C=O)(N=C=O)C1CCCCC1 KXBFLNPZHXDQLV-UHFFFAOYSA-N 0.000 claims description 2
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- DTGZJGZYPXAZTG-UHFFFAOYSA-N bicyclo[2.2.1]heptane;1,2-diisocyanatoethane Chemical compound C1CC2CCC1C2.O=C=NCCN=C=O DTGZJGZYPXAZTG-UHFFFAOYSA-N 0.000 claims description 2
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 230000008859 change Effects 0.000 claims description 2
- 150000002009 diols Chemical class 0.000 claims description 2
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 claims description 2
- 235000011187 glycerol Nutrition 0.000 claims description 2
- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 claims description 2
- 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 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- OEIJHBUUFURJLI-UHFFFAOYSA-N octane-1,8-diol Chemical compound OCCCCCCCCO OEIJHBUUFURJLI-UHFFFAOYSA-N 0.000 claims description 2
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 claims 1
- 239000005058 Isophorone diisocyanate Substances 0.000 claims 1
- 238000005227 gel permeation chromatography Methods 0.000 description 13
- 239000012948 isocyanate Substances 0.000 description 10
- 150000002513 isocyanates Chemical class 0.000 description 10
- 230000008569 process Effects 0.000 description 9
- 239000000178 monomer Substances 0.000 description 8
- 208000012839 conversion disease Diseases 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000003153 chemical reaction reagent Substances 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 5
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 5
- RMZAYIKUYWXQPB-UHFFFAOYSA-N trioctylphosphane Chemical compound CCCCCCCCP(CCCCCCCC)CCCCCCCC RMZAYIKUYWXQPB-UHFFFAOYSA-N 0.000 description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- SNAMIIGIIUQQSP-UHFFFAOYSA-N bis(6-methylheptyl) hydrogen phosphate Chemical compound CC(C)CCCCCOP(O)(=O)OCCCCCC(C)C SNAMIIGIIUQQSP-UHFFFAOYSA-N 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 239000004814 polyurethane Substances 0.000 description 4
- 229920002635 polyurethane Polymers 0.000 description 4
- 238000010998 test method Methods 0.000 description 4
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- AFVFQIVMOAPDHO-UHFFFAOYSA-M Methanesulfonate Chemical compound CS([O-])(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 description 3
- 150000001721 carbon Chemical group 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 239000008199 coating composition Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000003973 paint Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 239000010409 thin film Substances 0.000 description 3
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
- FFWSICBKRCICMR-UHFFFAOYSA-N 5-methyl-2-hexanone Chemical compound CC(C)CCC(C)=O FFWSICBKRCICMR-UHFFFAOYSA-N 0.000 description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 238000006471 dimerization reaction Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 230000007774 longterm Effects 0.000 description 2
- VUQUOGPMUUJORT-UHFFFAOYSA-N methyl 4-methylbenzenesulfonate Chemical compound COS(=O)(=O)C1=CC=C(C)C=C1 VUQUOGPMUUJORT-UHFFFAOYSA-N 0.000 description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
- 238000001225 nuclear magnetic resonance method Methods 0.000 description 2
- 238000011056 performance test Methods 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- YWWDBCBWQNCYNR-UHFFFAOYSA-N trimethylphosphine Chemical group CP(C)C YWWDBCBWQNCYNR-UHFFFAOYSA-N 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 description 1
- IUYYVMKHUXDWEU-UHFFFAOYSA-N 2,2,4-trimethylpentane-1,1-diol Chemical compound CC(C)CC(C)(C)C(O)O IUYYVMKHUXDWEU-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- MGTYKFIRHPNYPG-UHFFFAOYSA-N 4,4-dicyclopentylbutylphosphane Chemical compound C1CCCC1C(CCCP)C1CCCC1 MGTYKFIRHPNYPG-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- JYFHYPJRHGVZDY-UHFFFAOYSA-N Dibutyl phosphate Chemical compound CCCCOP(O)(=O)OCCCC JYFHYPJRHGVZDY-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- FYXKZNLBZKRYSS-UHFFFAOYSA-N benzene-1,2-dicarbonyl chloride Chemical compound ClC(=O)C1=CC=CC=C1C(Cl)=O FYXKZNLBZKRYSS-UHFFFAOYSA-N 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- WTHDANPEBBZWQC-UHFFFAOYSA-N benzyl(dimethyl)phosphane Chemical compound CP(C)CC1=CC=CC=C1 WTHDANPEBBZWQC-UHFFFAOYSA-N 0.000 description 1
- 239000002981 blocking agent Substances 0.000 description 1
- BNMJSBUIDQYHIN-UHFFFAOYSA-N butyl dihydrogen phosphate Chemical compound CCCCOP(O)(O)=O BNMJSBUIDQYHIN-UHFFFAOYSA-N 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- UCQFCFPECQILOL-UHFFFAOYSA-N diethyl hydrogen phosphate Chemical compound CCOP(O)(=O)OCC UCQFCFPECQILOL-UHFFFAOYSA-N 0.000 description 1
- DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 description 1
- 229940008406 diethyl sulfate Drugs 0.000 description 1
- UYAAVKFHBMJOJZ-UHFFFAOYSA-N diimidazo[1,3-b:1',3'-e]pyrazine-5,10-dione Chemical compound O=C1C2=CN=CN2C(=O)C2=CN=CN12 UYAAVKFHBMJOJZ-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 230000000447 dimerizing effect Effects 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- HTDKEJXHILZNPP-UHFFFAOYSA-N dioctyl hydrogen phosphate Chemical compound CCCCCCCCOP(O)(=O)OCCCCCCCC HTDKEJXHILZNPP-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- ANNNGOUEZBONHD-UHFFFAOYSA-N ethyl phenylmethanesulfonate Chemical compound CCOS(=O)(=O)CC1=CC=CC=C1 ANNNGOUEZBONHD-UHFFFAOYSA-N 0.000 description 1
- ZJXZSIYSNXKHEA-UHFFFAOYSA-L ethyl phosphate(2-) Chemical compound CCOP([O-])([O-])=O ZJXZSIYSNXKHEA-UHFFFAOYSA-L 0.000 description 1
- 239000011552 falling film Substances 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- GFAUNYMRSKVDJL-UHFFFAOYSA-N formyl chloride Chemical compound ClC=O GFAUNYMRSKVDJL-UHFFFAOYSA-N 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000000691 measurement method Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000010606 normalization Methods 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 150000003003 phosphines Chemical class 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229940116423 propylene glycol diacetate Drugs 0.000 description 1
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000005028 tinplate Substances 0.000 description 1
- IFXORIIYQORRMJ-UHFFFAOYSA-N tribenzylphosphane Chemical compound C=1C=CC=CC=1CP(CC=1C=CC=CC=1)CC1=CC=CC=C1 IFXORIIYQORRMJ-UHFFFAOYSA-N 0.000 description 1
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 1
- DHWBYAACHDUFAT-UHFFFAOYSA-N tricyclopentylphosphane Chemical compound C1CCCC1P(C1CCCC1)C1CCCC1 DHWBYAACHDUFAT-UHFFFAOYSA-N 0.000 description 1
- RXJKFRMDXUJTEX-UHFFFAOYSA-N triethylphosphine Chemical compound CCP(CC)CC RXJKFRMDXUJTEX-UHFFFAOYSA-N 0.000 description 1
- FPZZZGJWXOHLDJ-UHFFFAOYSA-N trihexylphosphane Chemical compound CCCCCCP(CCCCCC)CCCCCC FPZZZGJWXOHLDJ-UHFFFAOYSA-N 0.000 description 1
- IGNTWNVBGLNYDV-UHFFFAOYSA-N triisopropylphosphine Chemical compound CC(C)P(C(C)C)C(C)C IGNTWNVBGLNYDV-UHFFFAOYSA-N 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- 238000005829 trimerization reaction Methods 0.000 description 1
- IWPNEBZUNGZQQQ-UHFFFAOYSA-N tripentylphosphane Chemical compound CCCCCP(CCCCC)CCCCC IWPNEBZUNGZQQQ-UHFFFAOYSA-N 0.000 description 1
- KCTAHLRCZMOTKM-UHFFFAOYSA-N tripropylphosphane Chemical compound CCCP(CCC)CCC KCTAHLRCZMOTKM-UHFFFAOYSA-N 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 210000004885 white matter Anatomy 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
- C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
- C08G18/78—Nitrogen
- C08G18/79—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates
- C08G18/798—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing urethdione groups
-
- 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
- C08G18/16—Catalysts
- C08G18/166—Catalysts not provided for in the groups C08G18/18 - C08G18/26
- C08G18/168—Organic compounds
-
- C—CHEMISTRY; METALLURGY
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Abstract
Description
貯蔵安定性ポリイソシアネート組成物は、脂肪族ジイソシアネート、脂環式ジイソシアネートから選ばれる1種以上のジイソシアネートとアルコール系化合物とを反応させて得られ、且つイソシアヌレート基、ウレトジオン基、ウレタン基及びアロファネート基を含み、
前記ポリイソシアネート組成物において、ウレタン基/(ウレトジオン基+イソシアヌレート基)のモル割合は0.01~0.2であり、好ましくは0.01~0.1である。
3C-NMRにより求められる。即ち、156ppm付近のウレタン基のカルボニル基の炭素原子の信号面積(C1)を測定し、149ppm付近のイソシアヌレート基のカルボニル基に由来する炭素原子の信号の面積(C2)を測定し、158ppm付近のウレトジオン基に由来する炭素原子の信号の面積(C3)を測定し、モル比の式に従って測定値を算出する。
前記貯蔵安定性ポリイソシアネート組成物の調製方法は、具体的には、前記ジイソシアネートをアルコール系化合物と混合反応させ、反応温度を50~160℃、好ましくは50~150℃、より好ましくは50~120℃に制御し、該温度条件下ではウレタン化反応が容易に進行する傾向があり、同時に、ウレタンを形成した後に、アロファネートに変換可能であり、反応時間を0.5~4時間、好ましくは1時間に制御し、次に三級ホスフィン触媒を加え、反応温度を60~120℃、好ましくは60~100℃に制御し、反応時間を1~12時間、好ましくは1~8時間、より好ましくは1~5時間に制御する。また、アルコール系化合物はウレトジオンを含む反応液を生成する後期に加えてもよく、即ち、まず前記ジイソシアネートを三級ホスフィン触媒と混合反応させ、反応温度を50~150℃、好ましくは50~80℃に制御し、反応時間を0.5~12時間、好ましくは1~10時間に制御し、次にアルコール系化合物を加え、反応温度を60~120℃、好ましくは80~100℃に制御し、反応時間を1~3時間、好ましくは1~2時間に制御する。ウレトジオン及びイソシアヌレートの供給源はジイソシアネートを三級ホスフィン触媒の作用下で二量化及び三量化することである。
ウレトジオンポリイソシアネートは貯蔵過程で系の粘度が著しく増加する傾向がある。本願は系におけるウレタン基/(イソシアヌレート基+ウレトジオン基)の割合を制御することにより、製品の貯蔵過程における粘度の増加を抑制し、製品の貯蔵安定性を向上させる。
(1)GPC反応変換率の測定:
ゲルクロマトグラフィー技術(LC-20AD/RID-10A、カラムはMZ-Gel SDplus 10E3A 5μm(8.0*300mm)、MZ-Gel SDplus 500A 5μm(8.0*300mm)
、MZ-Gel SDplus 100A 5μm(8.0*300mm)直列、島津;移動相:テトラヒドロフラン;流速:1.0mL/min;分析時間:40min、カラム温度:35℃)を用いてイソシアネート原料を定量し、面積正規化法で測定系における多量体及びモノマーの面積を測定し、GPC反応変換率(%)=S(モノマーのピーク面積)/S(各成分のピーク面積の和)*100%である。
(2)イソシアネート基の濃度(NCO基の含有量)テストはGB/T 12009.4に準拠した。
(3)粘度の測定方法:動的な力学粘度はBrookField DV-I Prime粘度計でS21ローターを用いて25℃で測定した。
(4)ウレタン基/(ウレトジオン基+イソシアヌレート基)の測定:
該モル比をモル比1と記し、テスト方法は13C-NMR核磁気共鳴法を使用し、使用した機器はBruker 400MHz機器であり、サンプル濃度は50質量%(CDCl3溶液)であり、テスト条件は100MHzである。
該モル比の計算方法:モル比1=156ppm付近の信号面積/(149ppm付近の信号面積/3+158ppm付近の信号面積/2)。
(5)ウレタン基/(ウレタン+アロファネート)の測定:
該モル比をモル比2と記し、テスト方法はH-NMR核磁気共鳴法を使用し、使用した機器はBruker 400MHz機器であり、サンプル濃度は5質量%(CDCl3溶液)であり、テスト条件は400MHzである。
該モル比の計算方法:モル比2=4.9ppm付近の信号面積/(8.9ppm付近の信号面積+4.9ppm付近の信号面積)。
(6)硬化性
塗料組成物をブリキにコーティングし、15分間置き、80℃で60分間ベークし、室温で15分間置き、100グリッド法で付着力をテストし、付着力のテスト値が低いほど硬化性能がよい。
以下の各実施例で使用される原料の情報は次の通りである。
ヘキサメチレンジイソシアネート:万華科学、純度>99%;
2-エチル-1,3-ヘキサンジオール:アラジン試薬、純度>99%;
トリ-n-オクチルホスフィン:シグマ試薬、純度>95%;
リン酸ジイソオクチル:アラジン試薬、純度>99%;
トリ-n-ブチルホスフィン:アラジン試薬、純度>95%;
p-トルエンスルホン酸メチル:アラジン試薬、純度>99%。
他の原料及び試薬は、特に明記しない限り、すべて市販を通じて入手できる。
1-a、1-bのサンプルのように、低粘度系製品において、系におけるウレタンの絶対含有量が比較的高く、即ち、モル比1>0.2のとき、低粘度系の粘度の増加を抑制できるが、系におけるウレタン構造の相溶性がよくなく、貯蔵過程で系における混濁現象を引き起こしやすい。2-aのサンプルは顕著な混濁が示されていないが、モル比1が臨界値に近く、且つモル比2>0.4であるため、肉眼で見える透光性が悪く、全体が不均一である現象が現れた。
Claims (14)
- ポリイソシアネート組成物であって、
脂肪族ジイソシアネート、脂環式ジイソシアネートから選ばれる1種以上のジイソシアネートとアルコール系化合物とを反応させて得られ、且つイソシアヌレート基、ウレトジオン基、ウレタン基及びアロファネート基を含み、
前記ポリイソシアネート組成物において、ウレタン基/(ウレトジオン基+イソシアヌレート基)のモル割合は0.01~0.2である、貯蔵安定性ポリイソシアネート組成物。 - ウレタン基/(アロファネート基+ウレタン基)のモル比は0.01~0.4である、請求項1に記載の貯蔵安定性ポリイソシアネート組成物。
- イソシアネート基の濃度は16~24質量%である、請求項1又は2に記載の貯蔵安定性ポリイソシアネート組成物。
- ウレタン基/(ウレトジオン基+イソシアヌレート基)のモル割合は0.01~0.1であり、
好ましくは、ウレタン基/(アロファネート基+ウレタン基)のモル比は0.01~0.3であり、
好ましくは、イソシアネート基の濃度は20~23質量%である、請求項1に記載の貯蔵安定性ポリイソシアネート組成物。 - 25℃での粘度は100~1500cpであり、好ましくは130~1000cpである、請求項3に記載の貯蔵安定性ポリイソシアネート組成物。
- 前記アルコール系化合物の相対分子量は32~200であり、好ましくは、前記アルコール系化合物はメタノール、エタノール、n-プロパノール、イソプロパノール、n-ブタノール、n-ヘキサノール、2-エチル-1-ヘキサノール、1-メトキシ-2-プロパノール、エチレングリコール、プロピレングリコール、異性化ブタンジオール、ヘキサンジオール系、オクタンジオール系、ジエチレングリコール、ジプロピレングリコール、2-エチル-1,3-ヘキサンジオール、2,2,4-トリメチルペンタンジオール、グリセリン及びトリメチロールプロパンの1種又は複数種である、請求項1~5のいずれか一項に記載の貯蔵安定性ポリイソシアネート組成物。
- 前記脂肪族ジイソシアネート及び脂環式ジイソシアネートとは、炭素骨格にNCO基に加えて4~20個の炭素原子を含む有機ジイソシアネートを指す、請求項1~6のいずれか一項に記載の貯蔵安定性ポリイソシアネート組成物。
- 前記有機ジイソシアネートは、ヘキサメチレンジイソシアネート、イソホロンジイソシアネート、シクロヘキシルジメチレンジイソシアネート、ジシクロヘキシルメタンジイソシアネート、ノルボルナンジメチレンジイソシアネート、シクロヘキシルジイソシアネート及び2,4,4-トリメチルヘキサメチレンジイソシアナートの1種又は複数種である、請求項7に記載の貯蔵安定性ポリイソシアネート組成物。
- 40℃以下で6ヶ月貯蔵した時、製品の粘度変化≦10%である、請求項1~8のいずれか一項に記載の貯蔵安定性ポリイソシアネート組成物。
- 請求項1~9のいずれか一項に記載の貯蔵安定性ポリイソシアネート組成物の調製方法であって、
前記ジイソシアネートをアルコール系化合物と混合反応させ、反応温度を50~160℃に制御し、反応時間を0.5~4時間に制御することと、次に三級ホスフィン触媒を加え、反応温度を60~120℃、反応時間を1~12時間に制御することとを含むか、
或いは、前記ジイソシアネートを三級ホスフィン触媒と混合反応させ、反応温度を50~150℃に制御し、反応時間を0.5~12時間に制御することと、次にアルコール系化合物を加え、反応温度を60~120℃、反応時間を1~3時間に制御することとを含む、貯蔵安定性ポリイソシアネート組成物の調製方法。 - 前記ジイソシアネートをアルコール系化合物と混合反応させ、反応温度を50~150℃に制御する、請求項10に記載の貯蔵安定性ポリイソシアネート組成物の調製方法。
- 前記ジイソシアネートをアルコール系化合物と混合反応させ、反応時間を1時間に制御し、
好ましくは、三級ホスフィン触媒を加えた後に、反応温度を60~100℃に制御し、
好ましくは、三級ホスフィン触媒を加えた後に、反応時間を1~8時間に制御する、請求項10に記載の貯蔵安定性ポリイソシアネート組成物の調製方法。 - 前記ジイソシアネートを三級ホスフィン触媒と混合反応させ、反応温度を50~80℃に制御し、
好ましくは、前記ジイソシアネートを三級ホスフィン触媒と混合反応させ、反応時間を1~10時間に制御し、
好ましくは、アルコール系化合物を加えた後に、反応温度を80~100℃に制御し、
好ましくは、アルコール系化合物を加えた後に、反応時間を1~2時間に制御する、請求項10に記載の貯蔵安定性ポリイソシアネート組成物の調製方法。
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