CN103119084A - 用于制备用作交联剂的多官能的聚碳二亚胺的方法 - Google Patents
用于制备用作交联剂的多官能的聚碳二亚胺的方法 Download PDFInfo
- Publication number
- CN103119084A CN103119084A CN2011800450718A CN201180045071A CN103119084A CN 103119084 A CN103119084 A CN 103119084A CN 2011800450718 A CN2011800450718 A CN 2011800450718A CN 201180045071 A CN201180045071 A CN 201180045071A CN 103119084 A CN103119084 A CN 103119084A
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- China
- Prior art keywords
- carbodiimide
- poly
- functional group
- group
- isocyanate
- Prior art date
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Links
- 238000000034 method Methods 0.000 title claims abstract description 29
- 238000002360 preparation method Methods 0.000 title claims abstract description 13
- 239000003431 cross linking reagent Substances 0.000 title abstract 3
- 150000001718 carbodiimides Chemical class 0.000 claims abstract description 72
- 125000000524 functional group Chemical group 0.000 claims abstract description 31
- 229920001228 polyisocyanate Polymers 0.000 claims abstract description 21
- 239000005056 polyisocyanate Substances 0.000 claims abstract description 21
- 239000000203 mixture Substances 0.000 claims abstract description 19
- 238000006243 chemical reaction Methods 0.000 claims abstract description 17
- 238000000576 coating method Methods 0.000 claims abstract description 9
- 239000011248 coating agent Substances 0.000 claims abstract description 8
- 239000003960 organic solvent Substances 0.000 claims abstract description 5
- 239000000463 material Substances 0.000 claims abstract description 4
- -1 Aryl olefin Chemical class 0.000 claims description 57
- 150000001875 compounds Chemical class 0.000 claims description 34
- 150000002148 esters Chemical class 0.000 claims description 26
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 21
- 239000003795 chemical substances by application Substances 0.000 claims description 16
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 16
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 16
- 239000000126 substance Substances 0.000 claims description 15
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 14
- 239000004902 Softening Agent Substances 0.000 claims description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 13
- 239000002904 solvent Substances 0.000 claims description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
- 239000012948 isocyanate Substances 0.000 claims description 10
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 230000015572 biosynthetic process Effects 0.000 claims description 9
- 150000008065 acid anhydrides Chemical class 0.000 claims description 8
- 150000001299 aldehydes Chemical class 0.000 claims description 8
- 150000002576 ketones Chemical class 0.000 claims description 8
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 8
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 7
- 229920000570 polyether Polymers 0.000 claims description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- 150000004985 diamines Chemical class 0.000 claims description 6
- 150000002513 isocyanates Chemical class 0.000 claims description 6
- YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical compound CO[SiH](OC)OC YUYCVXFAYWRXLS-UHFFFAOYSA-N 0.000 claims description 6
- AOWPVIWVMWUSBD-RNFRBKRXSA-N [(3r)-3-hydroxybutyl] (3r)-3-hydroxybutanoate Chemical compound C[C@@H](O)CCOC(=O)C[C@@H](C)O AOWPVIWVMWUSBD-RNFRBKRXSA-N 0.000 claims description 4
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 4
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 claims description 4
- 125000000304 alkynyl group Chemical group 0.000 claims description 4
- 150000001733 carboxylic acid esters Chemical class 0.000 claims description 4
- 125000005594 diketone group Chemical group 0.000 claims description 4
- 150000004252 dithioacetals Chemical class 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 150000002466 imines Chemical class 0.000 claims description 4
- 150000002825 nitriles Chemical class 0.000 claims description 4
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 4
- 150000002923 oximes Chemical class 0.000 claims description 4
- 229920000728 polyester Polymers 0.000 claims description 4
- 229910000077 silane Inorganic materials 0.000 claims description 4
- 125000002769 thiazolinyl group Chemical group 0.000 claims description 4
- QQQSFSZALRVCSZ-UHFFFAOYSA-N triethoxysilane Chemical compound CCO[SiH](OCC)OCC QQQSFSZALRVCSZ-UHFFFAOYSA-N 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- 239000005864 Sulphur Substances 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 3
- 125000000468 ketone group Chemical group 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 239000000758 substrate Substances 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 2
- JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 claims description 2
- PKTOVQRKCNPVKY-UHFFFAOYSA-N dimethoxy(methyl)silicon Chemical compound CO[Si](C)OC PKTOVQRKCNPVKY-UHFFFAOYSA-N 0.000 claims description 2
- 150000003014 phosphoric acid esters Chemical group 0.000 claims description 2
- 239000000725 suspension Substances 0.000 claims description 2
- 239000004721 Polyphenylene oxide Substances 0.000 claims 4
- 229920000768 polyamine Polymers 0.000 claims 3
- 150000001335 aliphatic alkanes Chemical class 0.000 claims 2
- 229920005862 polyol Polymers 0.000 claims 2
- 229920002292 Nylon 6 Polymers 0.000 claims 1
- XYYQWMDBQFSCPB-UHFFFAOYSA-N dimethoxymethylsilane Chemical compound COC([SiH3])OC XYYQWMDBQFSCPB-UHFFFAOYSA-N 0.000 claims 1
- 150000002118 epoxides Chemical class 0.000 claims 1
- 125000000160 oxazolidinyl group Chemical group 0.000 claims 1
- 229920000515 polycarbonate Polymers 0.000 claims 1
- 239000004417 polycarbonate Substances 0.000 claims 1
- 229920005906 polyester polyol Polymers 0.000 claims 1
- 150000003077 polyols Chemical class 0.000 claims 1
- 239000003054 catalyst Substances 0.000 abstract description 5
- 239000004014 plasticizer Substances 0.000 abstract 1
- 125000004122 cyclic group Chemical group 0.000 description 14
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 125000001118 alkylidene group Chemical group 0.000 description 8
- 150000003254 radicals Chemical class 0.000 description 6
- ZUHZGEOKBKGPSW-UHFFFAOYSA-N tetraglyme Chemical compound COCCOCCOCCOCCOC ZUHZGEOKBKGPSW-UHFFFAOYSA-N 0.000 description 6
- 125000002877 alkyl aryl group Chemical group 0.000 description 5
- 239000006185 dispersion Substances 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- OROGUZVNAFJPHA-UHFFFAOYSA-N 3-hydroxy-2,4-dimethyl-2H-thiophen-5-one Chemical compound CC1SC(=O)C(C)=C1O OROGUZVNAFJPHA-UHFFFAOYSA-N 0.000 description 4
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 4
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
- 230000008901 benefit Effects 0.000 description 4
- 238000004132 cross linking Methods 0.000 description 4
- 229910052710 silicon Inorganic materials 0.000 description 4
- 239000010703 silicon Substances 0.000 description 4
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- OGYGFUAIIOPWQD-UHFFFAOYSA-N 1,3-thiazolidine Chemical compound C1CSCN1 OGYGFUAIIOPWQD-UHFFFAOYSA-N 0.000 description 3
- WYNCHZVNFNFDNH-UHFFFAOYSA-N Oxazolidine Chemical compound C1COCN1 WYNCHZVNFNFDNH-UHFFFAOYSA-N 0.000 description 3
- YSMRWXYRXBRSND-UHFFFAOYSA-N TOTP Chemical compound CC1=CC=CC=C1OP(=O)(OC=1C(=CC=CC=1)C)OC1=CC=CC=C1C YSMRWXYRXBRSND-UHFFFAOYSA-N 0.000 description 3
- 125000006226 butoxyethyl group Chemical group 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 125000000753 cycloalkyl group Chemical group 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 229920003009 polyurethane dispersion Polymers 0.000 description 3
- OTPDWCMLUKMQNO-UHFFFAOYSA-N 1,2,3,4-tetrahydropyrimidine Chemical compound C1NCC=CN1 OTPDWCMLUKMQNO-UHFFFAOYSA-N 0.000 description 2
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 2
- CXWGKAYMVASWDQ-UHFFFAOYSA-N 1,2-dithiane Chemical compound C1CCSSC1 CXWGKAYMVASWDQ-UHFFFAOYSA-N 0.000 description 2
- DKYBVKMIZODYKL-UHFFFAOYSA-N 1,3-diazinane Chemical compound C1CNCNC1 DKYBVKMIZODYKL-UHFFFAOYSA-N 0.000 description 2
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 description 2
- IMLSAISZLJGWPP-UHFFFAOYSA-N 1,3-dithiolane Chemical compound C1CSCS1 IMLSAISZLJGWPP-UHFFFAOYSA-N 0.000 description 2
- SLYRGJDSFOCAAI-UHFFFAOYSA-N 1,3-thiazolidin-2-one Chemical compound O=C1NCCS1 SLYRGJDSFOCAAI-UHFFFAOYSA-N 0.000 description 2
- YNGDWRXWKFWCJY-UHFFFAOYSA-N 1,4-Dihydropyridine Chemical compound C1C=CNC=C1 YNGDWRXWKFWCJY-UHFFFAOYSA-N 0.000 description 2
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- QWDQYHPOSSHSAW-UHFFFAOYSA-N 1-isocyanatooctadecane Chemical compound CCCCCCCCCCCCCCCCCCN=C=O QWDQYHPOSSHSAW-UHFFFAOYSA-N 0.000 description 2
- OXBLVCZKDOZZOJ-UHFFFAOYSA-N 2,3-Dihydrothiophene Chemical compound C1CC=CS1 OXBLVCZKDOZZOJ-UHFFFAOYSA-N 0.000 description 2
- JKTCBAGSMQIFNL-UHFFFAOYSA-N 2,3-dihydrofuran Chemical compound C1CC=CO1 JKTCBAGSMQIFNL-UHFFFAOYSA-N 0.000 description 2
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical compound O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 description 2
- IMSODMZESSGVBE-UHFFFAOYSA-N 2-Oxazoline Chemical compound C1CN=CO1 IMSODMZESSGVBE-UHFFFAOYSA-N 0.000 description 2
- RBGOQHAJHRGWJA-UHFFFAOYSA-N 2-oxooxolane-3-sulfonic acid Chemical compound S(=O)(=O)(O)C1C(=O)OCC1 RBGOQHAJHRGWJA-UHFFFAOYSA-N 0.000 description 2
- VSWICNJIUPRZIK-UHFFFAOYSA-N 2-piperideine Chemical compound C1CNC=CC1 VSWICNJIUPRZIK-UHFFFAOYSA-N 0.000 description 2
- RSEBUVRVKCANEP-UHFFFAOYSA-N 2-pyrroline Chemical compound C1CC=CN1 RSEBUVRVKCANEP-UHFFFAOYSA-N 0.000 description 2
- ATVJJNGVPSKBGO-UHFFFAOYSA-N 3,4-dihydro-2h-thiopyran Chemical compound C1CSC=CC1 ATVJJNGVPSKBGO-UHFFFAOYSA-N 0.000 description 2
- XKTYXVDYIKIYJP-UHFFFAOYSA-N 3h-dioxole Chemical compound C1OOC=C1 XKTYXVDYIKIYJP-UHFFFAOYSA-N 0.000 description 2
- BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 description 2
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 2
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 2
- 241000534944 Thia Species 0.000 description 2
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 2
- 238000013019 agitation Methods 0.000 description 2
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 description 2
- 125000003180 beta-lactone group Chemical group 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 229930188620 butyrolactone Natural products 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
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- SHQSVMDWKBRBGB-UHFFFAOYSA-N cyclobutanone Chemical compound O=C1CCC1 SHQSVMDWKBRBGB-UHFFFAOYSA-N 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- LOZWAPSEEHRYPG-UHFFFAOYSA-N dithiane Natural products C1CSCCS1 LOZWAPSEEHRYPG-UHFFFAOYSA-N 0.000 description 2
- 230000005611 electricity Effects 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 239000005357 flat glass Substances 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 150000002240 furans Chemical class 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 2
- 239000010985 leather Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- OOFGXDQWDNJDIS-UHFFFAOYSA-N oxathiolane Chemical compound C1COSC1 OOFGXDQWDNJDIS-UHFFFAOYSA-N 0.000 description 2
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- 229910052698 phosphorus Inorganic materials 0.000 description 2
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- USPWKWBDZOARPV-UHFFFAOYSA-N pyrazolidine Chemical compound C1CNNC1 USPWKWBDZOARPV-UHFFFAOYSA-N 0.000 description 2
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- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 2
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- 230000035484 reaction time Effects 0.000 description 2
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- RINCXYDBBGOEEQ-UHFFFAOYSA-N succinic anhydride Chemical compound O=C1CCC(=O)O1 RINCXYDBBGOEEQ-UHFFFAOYSA-N 0.000 description 2
- 229960002317 succinimide Drugs 0.000 description 2
- 150000003527 tetrahydropyrans Chemical class 0.000 description 2
- RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 description 2
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- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical group CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 2
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 2
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- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 1
- JHPBZFOKBAGZBL-UHFFFAOYSA-N (3-hydroxy-2,2,4-trimethylpentyl) 2-methylprop-2-enoate Chemical compound CC(C)C(O)C(C)(C)COC(=O)C(C)=C JHPBZFOKBAGZBL-UHFFFAOYSA-N 0.000 description 1
- HFSKWPUHEMGYMQ-UHFFFAOYSA-N 1,3-dioxolan-2-one Chemical compound O=C1OCCO1.O=C1OCCO1 HFSKWPUHEMGYMQ-UHFFFAOYSA-N 0.000 description 1
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 1
- GPNSPIGRLLHVCN-UHFFFAOYSA-N 1-cyclohexylazetidin-3-ol Chemical compound C1C(O)CN1C1CCCCC1 GPNSPIGRLLHVCN-UHFFFAOYSA-N 0.000 description 1
- SXJYSIBLFGQAND-UHFFFAOYSA-N 1-isocyanato-3-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC(N=C=O)=C1 SXJYSIBLFGQAND-UHFFFAOYSA-N 0.000 description 1
- IUUONVQOMMQAEH-UHFFFAOYSA-N 1-methyl-2,3-dihydro-1$l^{5}-phosphole 1-oxide Chemical compound CP1(=O)CCC=C1 IUUONVQOMMQAEH-UHFFFAOYSA-N 0.000 description 1
- ZHKJHQBOAJQXQR-UHFFFAOYSA-N 1H-azirine Chemical compound N1C=C1 ZHKJHQBOAJQXQR-UHFFFAOYSA-N 0.000 description 1
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- IBWDRPSBZYIJIU-UHFFFAOYSA-N 2-(2-ethyl-2-methyl-1,3-oxazolidin-3-yl)ethanol Chemical class CCC1(C)OCCN1CCO IBWDRPSBZYIJIU-UHFFFAOYSA-N 0.000 description 1
- OZDGMOYKSFPLSE-UHFFFAOYSA-N 2-Methylaziridine Chemical compound CC1CN1 OZDGMOYKSFPLSE-UHFFFAOYSA-N 0.000 description 1
- SJECZPVISLOESU-UHFFFAOYSA-N 3-trimethoxysilylpropan-1-amine Chemical compound CO[Si](OC)(OC)CCCN SJECZPVISLOESU-UHFFFAOYSA-N 0.000 description 1
- XYVMOLOUBJBNBF-UHFFFAOYSA-N 3h-1,3-oxazol-2-one Chemical compound OC1=NC=CO1 XYVMOLOUBJBNBF-UHFFFAOYSA-N 0.000 description 1
- YAWBIPCDUFAWQF-UHFFFAOYSA-N 4-ethyl-5h-1,3-oxazol-4-ol Chemical class CCC1(O)COC=N1 YAWBIPCDUFAWQF-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- XDSFZPURYILCRN-UHFFFAOYSA-N CP1=CCCC1 Chemical compound CP1=CCCC1 XDSFZPURYILCRN-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 description 1
- CTKINSOISVBQLD-UHFFFAOYSA-N Glycidol Chemical compound OCC1CO1 CTKINSOISVBQLD-UHFFFAOYSA-N 0.000 description 1
- 239000005058 Isophorone diisocyanate Substances 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000011149 active material Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
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Abstract
一种用于制备用作交联剂的多官能的聚碳二亚胺的方法，其中，聚碳二亚胺通过在含有一个或多个额外的活性官能团的单异氰酸酯或多异氰酸酯的存在下和在碳二亚胺催化剂的存在下使单异氰酸酯和多异氰酸酯反应并且之后使聚碳二亚胺链终止或扩链而制备。在聚碳二亚胺形成反应和/或封端反应和/或扩链反应期间、之前或之后，将0～10％的有机溶剂和/或0～30％的增塑剂和/或0～30％的表面活性组分添加到产物中。此外，本发明涉及一种其中聚碳二亚胺用作交联剂的涂料混合物并且涉及一种用所述涂料混合物得到的固化材料。
Description
背景技术
聚碳二亚胺是众所周知的用于含有羧酸官能团的水性聚合物的交联剂。聚碳二亚胺制备和应用的发展综述描述在EP1644428(US7439316)中。特别引人关注的是具有有助于交联的额外的官能团的聚碳二亚胺。
作为交联剂的多官能的聚碳二亚胺的制备和应用描述在EP0507407(US5258481)中。这些交联剂含有碳二亚胺基和至少一种其它官能团。这两种基团都有助于交联。制备方法中使用相对大量(约50％)的溶剂，否则在多官能的聚碳二亚胺交联剂的制备的第一阶段期间的粘度将变得过高。结果交联剂包含相对大量的挥发性有机化合物，由于环境原因，这些挥发性有机化合物目前是不想要的。此外，通过使用这种方法，碳二亚胺基的浓度和其它活性基团的浓度显然是相对低的，从而需要相对大量的多官能的聚碳二亚胺交联剂以对将被交联的聚合物获得良好的交联度。
在US6566437和US4118536的结论和实施例中描述了如何用具有烷氧基硅烷官能团的异氰酸酯能制备烷氧基硅烷官能的聚碳二亚胺，但是该聚碳二亚胺不含有亲水性基团并且结果将不能很好地分散在水或水性体系中。此外，在US6566437的实施例中使用了36％的有机溶剂，所以本方法的好处没有被公开。US4118536的实施例描述了如何用具有烷氧基硅烷官能的异氰酸酯能制备烷氧基硅烷官能的碳二亚胺，但在该实施例中重要的烷氧基硅烷官能的碳二亚胺以非常低的浓度被制备，从而缺少本方法的好处。
在本发明的目的是提供一种消除上述缺点的方法。
发明内容
根据本发明，提供一种用于制备用作交联剂的多官能的聚碳二亚胺的方法，所述方法包括：
A.在80～180℃下，在0.05～5wt％碳二亚胺催化剂的存在下，使单异氰酸酯和/或多异氰酸酯发生反应，其中，形成具有平均值为1～10的碳二亚胺官能团的聚碳二亚胺或异氰酸酯官能的聚碳二亚胺；
B.在聚碳二亚胺链形成期间或之后，在用含有一个或多个氨基和/或羟基官能团的化合物封端残余的异氰酸酯官能团之前，通过相对于在聚碳二亚胺链形成中未消耗的异氰酸酯官能团添加0.05～1.0当量的含有亲水性基团以及一个或多个氨基和/或羟基官能团的化合物，使异氰酸酯官能的聚碳二亚胺链终止和/或扩链，或者在聚碳二亚胺链形成期间或之后，通过相对于在聚碳二亚胺链形成中未消耗的异氰酸酯官能团添加0.05～1.0当量的含有亲水性基团以及一个或多个氨基和/或羟基官能团的化合物，使异氰酸酯官能的聚碳二亚胺链终止和/或扩链，随后用含有一个或多个氨基和/或羟基官能团的化合物封端残余的异氰酸酯官能团，其中含有一个或多个氨基和/或羟基官能团的化合物还能够包含额外的官能团，
其特征在于，在步骤A中，含有一个或多个额外的官能团的一种或多种单异氰酸酯和/或多异氰酸酯以0.5～30wt％存在，其中异氰酸酯基有助于碳二亚胺形成，并且其特征进一步在于，在碳二亚胺形成反应和/或封端反应和/或扩链反应期间、之前或之后，添加0～10％的有机溶剂和/或0～30％的增塑剂和/或0～30％的表面活性组分。
在EP0507407中，额外的官能团通过用含有该额外的官能团的羟基官能团或氨基官能团的化合物进行的异氰酸酯官能的碳二亚胺低聚物的终止反应而并入。令人惊讶地，明显在本方法中，如果额外的活性官能团没有根据在EP0507407中描述的方法而是通过碳二亚胺形成反应并入，则多官能团的聚碳二亚胺的粘度相当低。这可显著地避免或减少溶剂的使用，同时还可获得具有足够低粘度的多官能的聚碳二亚胺，从而它可容易地分散在水中。
通过碳二亚胺形成反应并入额外的活性官能团的额外优点是碳二亚胺基和额外的官能团两者的浓度都较高。其原因是，在每分子相同量的碳二亚胺官能团的情况下，产生的聚碳二亚胺的平均分子量低于其中通过终止反应并入额外的官能团的聚碳二亚胺的平均分子量。
与现有的具有额外的官能团的聚碳二亚胺相比，本发明的另一个优点是可以显著降低溶剂的量或可以完全避免使用溶剂。
在本方法中可以使用一定量的增塑剂。其原因是聚碳二亚胺与增塑剂的混合物相比聚碳二亚胺本身具有较低的粘度。这提高了易用性。优选具有一些亲水性的增塑剂，诸如磷酸三(丁氧基乙基)酯、四乙二醇二甲醚或三乙二醇单-2-己基己酸酯，以便聚碳二亚胺与增塑剂一起可以容易地分散在水或水性体系中。
根据本方法的方法制备的产品可以容易地分散在使用这些产品的水聚合物分散体或水性聚合物分散体中，因为亲水性基团已被并入聚合物中。
本方法中使用的单异氰酸酯和/或二异氰酸酯组分有几种选择。单异氰酸酯可以是含有6～25个碳原子的直链或支链的烷基、亚烷基、烷基-芳基或亚烷基-芳基的异氰酸酯。例如，它可以是烷基、环烷基、烷基-芳基或芳基烷基官能的异氰酸酯，诸如己基异氰酸酯、辛基异氰酸酯、十一烷基异氰酸酯、十二烷基异氰酸酯、十六烷基异氰酸酯、十八烷基异氰酸酯、环己基异氰酸酯、苯基异氰酸酯、甲苯基异氰酸酯、2-庚基-3，4-二(9-异氰酸根合壬基)-1-戊基环己烷。
进一步的选择是，单异氰酸酯和/或多异氰酸酯是多异氰酸酯与具有4～25个碳原子的直链或支链的烷基、亚烷基、烷基-芳基或亚烷基-芳基的羟基或氨基官能的化合物的加合物。
进一步的选择是，单异氰酸酯是含有1～50个氟原子的烷基、亚烷基、烷基-芳基或亚烷基-芳基的异氰酸酯。这些单异氰酸酯的实例是氟苯基异氰酸酯、氟甲苯基异氰酸酯和3-(三氟甲基)苯基异氰酸酯。
进一步的选择是，单异氰酸酯和/或多异氰酸酯是多异氰酸酯与具有包含1～50个氟原子的烷基、亚烷基、烷基-芳基或亚烷基-芳基的羟基或氨基官能的化合物的加合物。
进一步的选择是，单异氰酸酯和/或多异氰酸酯是多异氰酸酯与羟基官能的硅或氨基官能的硅、羟基烷基官能的硅或氨基烷基官能的硅的加合物。
用于制备聚碳二亚胺的多异氰酸酯是甲苯-2，4-二异氰酸酯、甲苯-2，6-二异氰酸酯和它们的混合物，是二苯基甲烷-4，4-二异氰酸酯、1，4-亚苯基二异氰酸酯、二环己基甲烷-4，4′-二异氰酸酯、3-异氰酸酯基甲基-3，5，5-三甲基环己基异氰酸酯、1，6-己基二异氰酸酯、1，4-环己基二异氰酸酯、降冰片基二异氰酸酯或它们的混合物。优选使用的多异氰酸酯是二环己基甲烷-4，4′-二异氰酸酯或3-异氰酸酯基甲基-3，5，5-三甲基环己基异氰酸酯。
含有一个或多个额外的活性官能团并且有助于形成异氰酸酯官能的聚碳二亚胺的单异氰酸酯是具有一个或多个不是碳二亚胺的活性基团的异氰酸酯化合物、对聚合物中的官能团或在水中的聚合物分散体、乳液或溶液中的官能团具有反应性的异氰酸酯化合物，或具有水解直接或之后自缩合或自加成能力的异氰酸酯化合物。活性官能团可以是卤素；烯基；芳基烯烃；炔基；芳基炔烃(arylalkyn)；二烯烃；醛；二烷基缩醛；二硫缩醛；酮；不饱和醛；酮或羧酸酯；腈；亚胺；烷基烷氧基硅烷；烷氧基硅烷；酸酐；混合酸酐；肟保护的二异氰酸酯；二酮；酮酯；硫酮酯(thioketoester)；酮硫酯(ketothioester)；硫酮硫酯(thioketothioester)；或一种或多种这些活性基团的混合物；活性官能团也可以是活性环体系或含有这样的体系。活性环体系可以是任何可以在亲电或亲核攻击下打开的环体系。活性环体系可以是任何含有一个或多个氮和/或氧和/或硫和/或酮基和/或酮-烯醇官能团的三、四、五、六、七或八元环。这类活性环体系的实例是氮丙啶、环氧化物、硫杂丙环、环氮乙烷(azirine)、环氧乙烯、硫杂丙烯环、氮杂环丁烷、氧杂环丁烷、硫杂环丁烷、β-内酰胺、β-内酯、硫杂环丁酮(thiethanon)、呋喃、吡咯啉、二氢呋喃、二氢噻吩、吡咯烷、四氢呋喃、四氢噻吩、噁唑烷、二氧戊环、氧硫杂环戊烷、噻唑烷、咪唑啉、二硫戊环、吡唑烷、吡唑啉、噁唑啉、噻唑啉、咪唑啉、间二氧杂环戊烯、噁唑酮(oxazolon)、吡咯烷酮、丁内酯、硫代丁内酯、丁基并硫代内酯(butyrothiolactone)、硫代丁基并硫代内酯(thiobutyrothiolactone)、噁唑烷酮、二氧戊环-2-酮(dioxolane-2-on)、噻唑烷酮、二氢吡啶、四氢吡啶、吡喃、二氢吡喃、四氢吡喃、琥珀酸酐、琥珀酰亚胺、噻喃、二氢噻喃、四氢噻喃、二氢嘧啶、四氢嘧啶、六氢嘧啶、二噁烷、吗啉、硫代吗啉、二噻烷和三嗪。
含有一个或多个额外的活性官能团并有助于形成异氰酸酯官能的聚碳二亚胺的单异氰酸酯优选是含有三甲氧基硅烷基、二甲氧基甲基硅烷基或三乙氧基硅烷基的异氰酸酯化合物，因为这些烷氧基硅烷基有效地有助于通过水解直接或之后自缩合的交联反应。
含有额外的活性基团的单异氰酸酯或多异氰酸酯优选是(3-异氰酸酯基丙基)三甲氧基硅烷、(3-异氰酸酯基丙基)三乙氧基硅烷或(3-异氰酸酯基丙基)甲基二甲氧基硅烷。
本方法中使用的碳二亚胺催化剂可以是任何常规的碳二亚胺催化剂，但优选使用1-甲基磷杂环戊烯氧化物(1-methylphospholene-oxide)。
含有亲水性基团以及一个或多个氨基和/或羟基官能团的化合物是分子量为100～3000道尔顿的聚乙氧基单醇或二醇、分子量为100～3000道尔顿且乙氧基/丙氧基之比为100/0～25/75的聚乙氧基/聚丙氧基单醇或二醇、分子量为100～3000的聚乙氧基单胺或二胺、分子量为100～3000道尔顿且乙氧基/丙氧基之比为100/0～25/75的聚乙氧基/聚丙氧基单胺或二胺、含有聚烷氧基悬挂链的二醇或二胺、羟基烷基磺酸酯或氨基烷基磺酸酯、或二烷基氨基烷基醇或二烷基氨基烷基胺，或它们的混合物。
含有一个或多个氨基和/或羟基官能团以及一个或多个额外的活性官能团的化合物是具有通过例如自缩合或自加成而对聚合物中的官能团或在水中的聚合物分散体、乳液或溶液中的官能团具有反应性或对相应的基团具有反应性的一个或多个活性基团的化合物。活性官能团可以是卤素；烯基；芳基烯烃；炔基；芳基炔烃；二烯烃；醛；二烷基缩醛；二硫缩醛；酮；不饱和醛；酮或羧酸酯；腈；亚胺；烷基烷氧基硅烷；烷氧基硅烷；酸酐；混合酸酐；肟保护的二异氰酸酯；二酮；酮酯；硫酮酯；酮硫酯；硫酮硫酯；或一种或多种这些活性基团的混合物；活性官能团也可以是活性环体系或含有活性环体系。活性环体系可以是任何可以在亲电或亲核攻击下打开的环体系。活性环体系可以是任何含有一个或多个氮和/或氧和/或硫和/或酮基和/或酮-烯醇官能团的三、四、五、六、七或八元环。这类活性环体系的实例是氮丙啶、环氧化物、硫杂丙环、环氮乙烷、环氧乙烯、硫杂丙烯环、氮杂环丁烷、氧杂环丁烷、硫杂环丁烷、β-内酰胺、β-内酯、硫杂环丁酮、呋喃、吡咯啉、二氢呋喃、二氢噻吩、吡咯烷、四氢呋喃、四氢噻吩、噁唑烷、二氧戊环、氧硫杂环戊烷、噻唑烷、咪唑啉、二硫戊环、吡唑烷、吡唑啉、噁唑啉、噻唑啉、咪唑啉、间二氧杂环戊烯、噁唑酮、吡咯烷酮、丁内酯、硫代丁内酯、丁基并硫代内酯、硫代丁基并硫代内酯、噁唑烷酮、二氧戊环-2-酮、噻唑烷酮、二氢吡啶、四氢吡啶、吡喃、二氢吡喃、四氢吡喃、琥珀酸酐、琥珀酰亚胺、噻喃、二氢噻喃、四氢噻喃、二氢嘧啶、四氢嘧啶、六氢嘧啶、二噁烷、吗啉、硫代吗啉、二噻烷和三嗪。
如果该环体系含有诸如2-甲基氮丙啶、4，4-二甲基噁唑烷、噻唑烷等中的活性质子，含有活性质子的化合物可以是环体系。活性质子可存在于羟基化合物或胺化合物中。这些活性质子直接或通过诸如1-(2-羟乙基)亚乙基亚胺、缩水甘油、N-环己基-3-羟基-氮杂环丁烷、2-乙基-3-羟乙基-2-甲基-噁唑烷、4-乙基-4-羟基-噁唑啉、烯丙基醇、甲基乙基酮肟、1-氨基-3-(三乙氧基甲硅烷基)-丙烷、1-氨基-3-(三甲氧基甲硅烷基)-丙烷中可选的烷基、环烷基或芳基而连接到额外的官能团或活性环体系。进一步的选择是，活性质子存在于羟基化合物或胺化合物中而且这些活性质子直接或通过在一个或多个额外的官能团上可选的烷基、环烷基或芳基而连接到额外的官能团。实例是二(3-三甲氧基甲硅烷基丙基)胺。具有两个或更多个活性质子的化合物也可使用，诸如N-(3-三甲氧基甲硅烷基丙基)-1，2-二氨基乙烷。
增塑剂是选自邻苯二甲酸烷基酯、己二酸烷基酯、癸二酸烷基酯、十二烷酸烷基酯、聚酯、磷酸酯、聚醚、聚醚-聚酯、脂肪酸酯、普通的或改性的天然油或矿物油、磺化油、乙氧基化油、环氧化油、脂肪酸、磺酰胺、油乳液、卵磷脂或它们的混合物的组中的增塑剂。优选具有一些亲水性的增塑剂，诸如磷酸三(丁氧基乙基)酯、四乙二醇二甲醚或三乙二醇单-2-己基己酸酯，以便聚碳二亚胺与增塑剂一起可以容易地分散在水或水性体系中。
表面活性材料是在涂料工业中使用的除羟基或氨基官能类型以外的常规的离子型或非离子型表面活性剂。异氰酸酯官能的聚碳二亚胺与含有亲水性基团以及一个或多个羟基或氨基的化合物的反应可以通过在聚合物工业中使用的常规催化剂催化。
本发明还涉及一种涂料混合物，包含分散在水中的作为交联剂的聚碳二亚胺和聚合物，其中该聚合物含有羧酸官能团，并且该涂料混合物可包含溶剂。
这些聚合物的实例是聚氨酯、丙烯酸酯或甲基丙烯酸酯的聚合物或共聚物、聚乙酸乙烯酯、乳胶。
进一步，涂料混合物可以包含有机溶剂或常规的添加剂，诸如乳化剂、着色剂、颜料、湿润剂、流平剂、硅树脂、填料、增塑剂、消光剂。
最后，本发明扩展至通过将涂料混合物涂布到基底并且蒸发水和如果存在的溶剂而得到的固化材料。
合适的基底例如为皮革、人造皮革、诸如聚氨酯、聚丙烯酸酯、聚乙烯、聚丙烯、聚氯乙烯或聚酯的塑料、纸、纸板、纺织品、无纺布、布、泡沫、木材、玻璃、金属、沥青、石头、混凝土。
具体实施方式
本发明通过下列实施例进一步说明，然而本发明并不限于此。不言而喻，可进行多种其它的实施方式，它们都在保护范围内。
实施例
实施例1～26：多官能的聚碳二亚胺的制备。
在氮气氛围下，将表1中所示的二异氰酸酯、十八烷基异氰酸酯(在下文中表示为ODIC)和具有额外的官能团的异氰酸酯以及1-甲基磷杂环戊烯-1-氧化物的混合物在搅拌下加热至140℃，并继续加热直到得到对应于如表1中所示的在聚合物中所需的理论量的碳二亚胺官能团的NCO含量。反应时间是4～8小时。然后将混合物冷却至90～100℃。添加如表1中所示的羟基官能的化合物。添加0.01wt％的二月桂酸二丁基锡或羧酸铋作为催化剂并且使该混合物在90～100℃下进一步反应直到NCO含量下降，使得此NCO含量对应于反应消耗的羟基官能的化合物。随后或同时添加如表1中所示的氨基官能的化合物。通过红外分析来检查反应的完全性。在上述过程步骤期间或之后，添加表1中所示的增塑剂。在50℃下对样品进行稳定性测试。每两周检查碳二亚胺量。产品在50℃下至少8周是稳定的。
a)IPDI是3-异氰酸酯基甲基-3，5，5-三甲基环己基异氰酸酯；
b)HMDI是二环己基甲烷-4，4′-二异氰酸酯；
c)X-NCO是具有额外的官能团的异氰酸酯，具体的进一步在脚注中指出；
d)MPEG750是具有平均分子量为750的聚乙二醇单甲醚；
e)MPEG350是具有平均分子量为350的聚乙二醇单甲醚；
f)HDA是十六烷基醇；
g)OA是1-辛醇；
h)硅烷-NH是二(3-三甲氧基甲硅烷基丙基)胺；
i)TBEP是磷酸三(丁氧基乙基)酯；
j)TG是四乙二醇二甲醚；
k)具有额外的官能团的异氰酸酯是(3-异氰酸酯基丙基)三甲氧基硅烷；
l)具有额外的官能团的异氰酸酯是(3-异氰酸酯基丙基)三乙氧基硅烷；
m)具有额外的官能团的异氰酸酯是甲基丙烯酰基异氰酸酯
实施例27：比较例：不使用含有额外的官能团的异氰酸酯的多官能的聚碳二亚胺的制备。
在氮气氛围下，将如表1中所示的二异氰酸酯和1-甲基磷杂环戊烯-1-氧化物的混合物在搅拌下加热至140℃，并继续加热直到得到对应于如表1中所示的在聚合物中所需的理论量的碳二亚胺官能团的NCO含量。反应时间是4～8小时。然后将混合物冷却至90～100℃。添加如表1中所示的羟基官能的化合物。添加0.01wt％的二月桂酸二丁基锡作为催化剂并且使该混合物在90～100℃下进一步反应直到NCO含量下降，使得此NCO含量对应于反应消耗的羟基官能的化合物。随后，添加如表1中所示的氨基官能的化合物。通过红外分析来检查反应的完全性。
实施例27的粘度与实施例1～4和10～26的粘度比较表明，在聚合物中碳二亚胺官能团的理论量相同时，实施例1～4和10～26的粘度比实施例27的粘度低得多。尽管实施例5和7中的聚合物中碳二亚胺官能团的理论量比在实施例27中的聚合物中碳二亚胺官能团的理论量高，但实施例5和7的粘度比实施例27的粘度也低得多。
实施例28：
来自实施例2、12、13、15、19、23和24的产品作为聚氨酯分散体中的交联剂与来自实施例27的产品作为比较例的测试。
将6wt％的来自实施例2、12、13、15、19、23和24的产品与RU-13-085(+StahlEurope的聚氨酯分散体)混合或与面漆配方(top coat formulation)(包含几种Stahl Europe的聚氨酯分散体的混合物)混合。在比较实施例27的情况下，首先制成在溶剂中的1∶1稀释物，以便改善可加工性，并随后将12wt％的该稀释物与RU-13-085混合或与面漆配方混合。将厚度为200μm的每种分散体涂布到玻璃片上而且将其上涂布膜的玻璃片在室温下干燥1天并且随后在烘箱中80℃下干燥1小时。用作为溶剂的乙醇或MEK(甲基乙基酮或2-丁酮)对干燥的膜样品进行溶剂吸收测试。在该测试中，将干燥且称重过的膜片浸入到乙醇或MEK中1小时并随后测定膜重量的增加。
在该溶剂吸收测试中的重量增加是交联的量度，其中较低的重量增加表示较高的交联度。另外，用MTS Synergy 200装置测量膜的机械性能和延伸率。机械性能是交联的量度，其中在一定的应变下较大的应力值表示较高的交联度。测试的结果示于表2。
结果表明，用实施例2、12、13、15、19、23和24的交联剂的交联具有与比较实施例27类似的程度，这通过当膜被拉伸时得到的膜中类似的应变以及当将膜浸入在乙醇或MEK中时类似的重量增加而证明。
表2
a)MPa是兆帕(106Nm-2)。在MTS Synergy 200装置上测量机械性能。在M-100和M-200处的值是当它们分别被拉伸为100％和200％时膜的应变。
b)延伸率是在MTS Synergy 200装置上测量的在膜断裂时刻的最大延伸率。
c)重量增加是由于浸入到乙醇中膜的重量增加％。
d)重量增加是由于浸入到MEK(甲基乙基酮或2-丁酮)中膜的重量增加％。
Claims (14)
1.一种用于制备用作交联剂的多官能的聚碳二亚胺的方法，包括：
A.在80～180℃下，在0.05～5wt％碳二亚胺催化剂的存在下使单异氰酸酯和/或多异氰酸酯发生反应，其中，形成具有平均值为1～10的碳二亚胺官能团的聚碳二亚胺或异氰酸酯官能的聚碳二亚胺；
B.在聚碳二亚胺链形成期间或之后，在用含有一个或多个氨基和/或羟基官能团的化合物封端残余的异氰酸酯官能团之前，通过相对于在聚碳二亚胺链形成中未消耗的异氰酸酯官能团添加0.05～1.0当量的含有亲水性基团以及一个或多个氨基和/或羟基官能团的化合物，使异氰酸酯官能的聚碳二亚胺链终止和/或扩链，或者在聚碳二亚胺链形成期间或之后，通过相对于在聚碳二亚胺链形成中未消耗的异氰酸酯官能团添加0.05～1.0当量的含有亲水性基团以及一个或多个氨基和/或羟基官能团的化合物，使异氰酸酯官能的聚碳二亚胺链终止和/或扩链，随后用含有一个或多个氨基和/或羟基官能团的化合物封端残余的异氰酸酯官能团，其中含有一个或多个氨基和/或羟基官能团的化合物还能够包含额外的官能团，
其特征在于，在步骤A中，含有一个或多个额外的官能团的一种或多种单异氰酸酯和/或多异氰酸酯以0.5～30wt％存在，其中异氰酸酯基有助于碳二亚胺形成，并且其特征进一步在于，在碳二亚胺形成反应和/或封端反应和/或扩链反应期间、之前或之后，添加0～10％的有机溶剂和/或0～30％的增塑剂和/或0～30％的活性表面组分。
2.根据权利要求1所述的方法，其特征在于，含有额外的官能团的单异氰酸酯和/或多异氰酸酯的所述额外的官能团是卤素；烯基；芳基烯烃；炔基；芳基炔烃；二烯烃；醛；二烷基缩醛；二硫缩醛；酮；不饱和醛；酮或羧酸酯；腈；亚胺；烷基烷氧基硅烷；烷氧基硅烷；酸酐；混合酸酐；肟保护的二异氰酸酯；二酮；酮酯；硫酮酯；酮硫酯；硫酮硫酯；或一种或多种这些活性基团的混合物。
3.根据权利要求1和2所述的方法，其特征在于，含有额外的官能团的所述单异氰酸酯和/或多异氰酸酯包含三甲氧基硅烷、二甲氧基甲基硅烷或三乙氧基硅烷作为额外的活性官能团。
4.根据权利要求1所述的方法，其特征在于，含有额外的官能团的所述单异氰酸酯和/或多异氰酸酯包含具有一个或多个氮和/或氧和/或硫和/或酮基和/或酮-烯醇官能团的三、四、五、六、七或八元环作为额外的活性官能团。
5.根据权利要求1～3所述的方法，其特征在于，含有额外的官能团的所述单异氰酸酯和/或多异氰酸酯是(3-异氰酸酯基丙基)三甲氧基硅烷、(3-异氰酸酯基丙基)三乙氧基硅烷或(3-异氰酸酯基丙基)甲基二甲氧基硅烷。
6.根据权利要求1所述的方法，其特征在于，所述聚碳二亚胺交联剂不包含溶剂。
7.根据权利要求1～6所述的方法，其特征在于，所述聚碳二亚胺交联剂不包含增塑剂。
8.根据权利要求1～7所述的方法，其特征在于，所述增塑剂是磷酸酯、聚醚聚酯或聚醚。
9.根据权利要求1～8所述的方法，其特征在于，含有一个或多个氨基和/或羟基官能团以及一个或多个额外的活性官能团的化合物包含额外的活性官能团，其中所述额外的活性官能团是卤素；烯基；芳基烯烃；炔基；芳基炔烃；二烯烃；醛；二烷基缩醛；二硫缩醛；酮；不饱和醛；酮或羧酸酯；腈；亚胺；烷基烷氧基硅烷；烷氧基硅烷；酸酐；混合酸酐；肟保护的二异氰酸酯；二酮；酮酯；硫酮酯；酮硫酯；硫酮硫酯；或一种或多种这些活性基团的混合物。
9、根据权利要求1～9所述的方法，其特征在于，在含有一个或多个氨基和/或羟基官能团以及一个或多个额外的活性官能团的化合物中的额外的活性官能团优选是三甲氧基硅烷基、三乙氧基硅烷基、环氧化物基、氮丙啶基或噁唑烷基。
10.根据权利要求1所述的方法，其特征在于，所述多异氰酸酯是二环己基甲烷-4，4′-二异氰酸酯或3-异氰酸酯基甲基-3，5，5-三甲基环己基异氰酸酯。
11.根据权利要求1～11所述的方法，其特征在于，所述含有亲水性基团以及一个或多个氨基和/或羟基官能团的化合物是分子量为100～3000道尔顿的聚乙氧基单醇或二醇、分子量为100～3000道尔顿且乙氧基/丙氧基之比为100/0～25/75的聚乙氧基/聚丙氧基单醇或二醇、分子量为100～3000的聚乙氧基单胺或二胺、分子量为100～3000道尔顿且乙氧基/丙氧基之比为100/0～25/75的聚乙氧基/聚丙氧基单胺或二胺、含有聚烷氧基悬挂链的二醇或二胺、羟基烷基磺酸酯或氨基烷基磺酸酯、或二烷基氨基烷基醇或二烷基氨基烷基胺，或它们的混合物。
12.根据权利要求1～12所述的方法，其特征在于，在聚碳二亚胺链形成期间、之前或之后，相对于多异氰酸酯添加0.05～0.30当量的单醇或多元醇或单胺或多胺，其中，所述单醇或多元醇或单胺或多胺是单羟基烷烃或多羟基烷烃、聚醚单醇或聚醚多元醇、聚酯多元醇、聚碳酸酯多元醇、聚己内酰胺多元醇、单氨基烷烃或多氨基烷烃，或聚醚单胺或聚醚多胺。
13.一种涂料混合物，包含在水中分散的作为交联剂的根据权利要求1～13所述的聚碳二亚胺和聚合物，其中聚合物含有羧酸官能团。
14.一种通过将根据权利要求14所述的涂料混合物涂布到基底并蒸发水和如果存在的溶剂而得到的固化材料。
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| CN1105688A (zh) * | 1993-06-11 | 1995-07-26 | 罗姆和哈斯公司 | 芳族聚碳化二亚胺交联剂 |
| EP1162237A1 (en) * | 2000-06-05 | 2001-12-12 | Rohm And Haas Company | Wear-resistant coating composition and method of producing a coating |
| CN101374876A (zh) * | 2006-02-02 | 2009-02-25 | 斯塔尔国际有限公司 | 制备交联剂水分散液的方法 |
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| CN106232667A (zh) * | 2014-02-20 | 2016-12-14 | 巴斯夫欧洲公司 | 聚异脲 |
| CN106232667B (zh) * | 2014-02-20 | 2020-01-07 | 巴斯夫欧洲公司 | 聚异脲 |
| US11028216B2 (en) | 2016-11-18 | 2021-06-08 | Nisshinbo Chemical Inc. | Polycarbodiimide copolymer |
| CN109952333A (zh) * | 2016-11-18 | 2019-06-28 | 日清纺化学株式会社 | 聚碳化二亚胺共聚物 |
| CN110461956A (zh) * | 2017-02-06 | 2019-11-15 | 巴斯夫欧洲公司 | 用于在基底上形成涂层的水性体系 |
| CN111868023A (zh) * | 2018-03-12 | 2020-10-30 | 日清纺化学株式会社 | 碳化二亚胺化合物的制备方法 |
| CN111836797A (zh) * | 2018-03-12 | 2020-10-27 | 日清纺化学株式会社 | 碳化二亚胺化合物的制备方法 |
| US12017977B2 (en) | 2018-03-12 | 2024-06-25 | Nisshinbo Chemical Inc. | Method for producing carbodiimide compound |
| US12071395B2 (en) | 2018-03-12 | 2024-08-27 | Nisshinbo Chemical Inc. | Method for producing carbodiimide compound |
| CN116143660A (zh) * | 2018-05-15 | 2023-05-23 | 旭化成株式会社 | 化合物、固化剂组合物、树脂组合物、涂料组合物和树脂固化物 |
| CN108715628A (zh) * | 2018-06-22 | 2018-10-30 | 上海朗亿功能材料有限公司 | 一种脂环族聚碳化二亚胺抗水解剂及其制备方法 |
| CN108715628B (zh) * | 2018-06-22 | 2022-04-01 | 上海朗亿功能材料有限公司 | 一种脂环族聚碳化二亚胺抗水解剂及其制备方法 |
| CN115040699A (zh) * | 2021-03-09 | 2022-09-13 | 上海硕创生物医药科技有限公司 | 热固化透明质酸钠涂层、医用导管及器械 |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2013538795A (ja) | 2013-10-17 |
| KR101811477B1 (ko) | 2017-12-26 |
| MX2013001123A (es) | 2013-06-03 |
| US9546301B2 (en) | 2017-01-17 |
| EP2598555A1 (en) | 2013-06-05 |
| KR20140004622A (ko) | 2014-01-13 |
| CN103119084B (zh) | 2014-11-19 |
| MX347005B (es) | 2017-04-07 |
| NL2005163C2 (nl) | 2012-01-31 |
| JP5883865B2 (ja) | 2016-03-15 |
| PL2598555T3 (pl) | 2015-04-30 |
| PT2598555E (pt) | 2014-11-10 |
| WO2012015295A1 (en) | 2012-02-02 |
| BR112013003650B1 (pt) | 2022-03-03 |
| ES2522550T3 (es) | 2014-11-17 |
| EP2598555B1 (en) | 2014-10-08 |
| BR112013003650A2 (pt) | 2021-04-13 |
| US20130144006A1 (en) | 2013-06-06 |
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