CN104693414A - 亚氨基噁二嗪二酮多异氰酸酯 - Google Patents
亚氨基噁二嗪二酮多异氰酸酯 Download PDFInfo
- Publication number
- CN104693414A CN104693414A CN201410749977.3A CN201410749977A CN104693414A CN 104693414 A CN104693414 A CN 104693414A CN 201410749977 A CN201410749977 A CN 201410749977A CN 104693414 A CN104693414 A CN 104693414A
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- CN
- China
- Prior art keywords
- polyisocyanates
- carbon atom
- groups
- zirconium
- catalyzer
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- 239000005056 polyisocyanate Substances 0.000 title claims abstract description 60
- 229920001228 polyisocyanate Polymers 0.000 title claims abstract description 60
- PJMDLNIAGSYXLA-UHFFFAOYSA-N 6-iminooxadiazine-4,5-dione Chemical compound N=C1ON=NC(=O)C1=O PJMDLNIAGSYXLA-UHFFFAOYSA-N 0.000 title abstract 3
- 238000000034 method Methods 0.000 claims abstract description 42
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 claims abstract description 32
- 229910052726 zirconium Inorganic materials 0.000 claims abstract description 28
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 claims abstract description 27
- 239000012948 isocyanate Substances 0.000 claims abstract description 27
- 150000002513 isocyanates Chemical class 0.000 claims abstract description 27
- 229910052735 hafnium Inorganic materials 0.000 claims abstract description 18
- VBJZVLUMGGDVMO-UHFFFAOYSA-N hafnium atom Chemical compound [Hf] VBJZVLUMGGDVMO-UHFFFAOYSA-N 0.000 claims abstract description 17
- 239000010936 titanium Substances 0.000 claims abstract description 16
- 229910052719 titanium Inorganic materials 0.000 claims abstract description 16
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims abstract description 15
- 229920002396 Polyurea Polymers 0.000 claims abstract description 4
- -1 isocyanuric acid ester Chemical class 0.000 claims description 48
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 claims description 34
- 238000006243 chemical reaction Methods 0.000 claims description 28
- 125000004432 carbon atom Chemical group C* 0.000 claims description 25
- 229910052799 carbon Inorganic materials 0.000 claims description 23
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 22
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 18
- 125000001931 aliphatic group Chemical group 0.000 claims description 16
- 150000001875 compounds Chemical class 0.000 claims description 16
- 229910052757 nitrogen Inorganic materials 0.000 claims description 14
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 11
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 10
- 229910052760 oxygen Inorganic materials 0.000 claims description 10
- 239000001301 oxygen Substances 0.000 claims description 10
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 9
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 8
- 239000005864 Sulphur Substances 0.000 claims description 8
- 229920006395 saturated elastomer Polymers 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 125000005842 heteroatom Chemical group 0.000 claims description 6
- 125000000623 heterocyclic group Chemical group 0.000 claims description 6
- 239000003153 chemical reaction reagent Substances 0.000 claims description 5
- 125000004429 atom Chemical group 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 3
- 150000004703 alkoxides Chemical class 0.000 claims description 3
- 230000000737 periodic effect Effects 0.000 claims description 2
- 230000000717 retained effect Effects 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 abstract description 16
- 239000004814 polyurethane Substances 0.000 abstract description 6
- 229920002635 polyurethane Polymers 0.000 abstract description 4
- 230000008569 process Effects 0.000 abstract description 3
- 239000000203 mixture Substances 0.000 description 41
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 40
- 239000002904 solvent Substances 0.000 description 32
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 30
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 239000011541 reaction mixture Substances 0.000 description 16
- 125000005594 diketone group Chemical group 0.000 description 15
- 239000000243 solution Substances 0.000 description 15
- 150000002148 esters Chemical class 0.000 description 13
- 239000000178 monomer Substances 0.000 description 12
- AVWRKZWQTYIKIY-UHFFFAOYSA-N urea-1-carboxylic acid Chemical compound NC(=O)NC(O)=O AVWRKZWQTYIKIY-UHFFFAOYSA-N 0.000 description 12
- 239000002253 acid Substances 0.000 description 10
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 10
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 10
- FDQSRULYDNDXQB-UHFFFAOYSA-N benzene-1,3-dicarbonyl chloride Chemical compound ClC(=O)C1=CC=CC(C(Cl)=O)=C1 FDQSRULYDNDXQB-UHFFFAOYSA-N 0.000 description 9
- 231100000614 poison Toxicity 0.000 description 9
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 8
- 239000004202 carbamide Substances 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 7
- 239000002574 poison Substances 0.000 description 7
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical class CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 238000004821 distillation Methods 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000003973 paint Substances 0.000 description 5
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 235000011187 glycerol Nutrition 0.000 description 4
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 4
- BPYXFMVJXTUYRV-UHFFFAOYSA-J octanoate;zirconium(4+) Chemical class [Zr+4].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O.CCCCCCCC([O-])=O.CCCCCCCC([O-])=O BPYXFMVJXTUYRV-UHFFFAOYSA-J 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 239000008199 coating composition Substances 0.000 description 3
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical group CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 3
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- BZJTUOGZUKFLQT-UHFFFAOYSA-N 1,3,5,7-tetramethylcyclooctane Chemical group CC1CC(C)CC(C)CC(C)C1 BZJTUOGZUKFLQT-UHFFFAOYSA-N 0.000 description 2
- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 2
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 2
- RWLALWYNXFYRGW-UHFFFAOYSA-N 2-Ethyl-1,3-hexanediol Chemical compound CCCC(O)C(CC)CO RWLALWYNXFYRGW-UHFFFAOYSA-N 0.000 description 2
- IXQGCWUGDFDQMF-UHFFFAOYSA-N 2-Ethylphenol Chemical compound CCC1=CC=CC=C1O IXQGCWUGDFDQMF-UHFFFAOYSA-N 0.000 description 2
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 2
- SVTBMSDMJJWYQN-UHFFFAOYSA-N 2-methylpentane-2,4-diol Chemical compound CC(O)CC(C)(C)O SVTBMSDMJJWYQN-UHFFFAOYSA-N 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- HXDOZKJGKXYMEW-UHFFFAOYSA-N 4-ethylphenol Chemical compound CCC1=CC=C(O)C=C1 HXDOZKJGKXYMEW-UHFFFAOYSA-N 0.000 description 2
- YPIFGDQKSSMYHQ-UHFFFAOYSA-N 7,7-dimethyloctanoic acid Chemical compound CC(C)(C)CCCCCC(O)=O YPIFGDQKSSMYHQ-UHFFFAOYSA-N 0.000 description 2
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical group NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 239000005058 Isophorone diisocyanate Substances 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
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 230000000996 additive effect Effects 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
- 239000012752 auxiliary agent Substances 0.000 description 2
- 235000019445 benzyl alcohol Nutrition 0.000 description 2
- 229960004217 benzyl alcohol Drugs 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 229910052797 bismuth Inorganic materials 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 2
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 2
- 230000009849 deactivation Effects 0.000 description 2
- 229940028356 diethylene glycol monobutyl ether Drugs 0.000 description 2
- 229940075557 diethylene glycol monoethyl ether Drugs 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 2
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 2
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 2
- 235000019439 ethyl acetate Nutrition 0.000 description 2
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 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 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 229940043265 methyl isobutyl ketone Drugs 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- ZWRUINPWMLAQRD-UHFFFAOYSA-N nonan-1-ol Chemical compound CCCCCCCCCO ZWRUINPWMLAQRD-UHFFFAOYSA-N 0.000 description 2
- RZJRJXONCZWCBN-UHFFFAOYSA-N octadecane Chemical compound CCCCCCCCCCCCCCCCCC RZJRJXONCZWCBN-UHFFFAOYSA-N 0.000 description 2
- VRQWWCJWSIOWHG-UHFFFAOYSA-J octadecanoate;zirconium(4+) Chemical class [Zr+4].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O VRQWWCJWSIOWHG-UHFFFAOYSA-J 0.000 description 2
- 238000006384 oligomerization reaction Methods 0.000 description 2
- JCGNDDUYTRNOFT-UHFFFAOYSA-N oxolane-2,4-dione Chemical compound O=C1COC(=O)C1 JCGNDDUYTRNOFT-UHFFFAOYSA-N 0.000 description 2
- 230000007096 poisonous effect Effects 0.000 description 2
- 229920000768 polyamine Polymers 0.000 description 2
- 108010064470 polyaspartate Proteins 0.000 description 2
- 229920005862 polyol Polymers 0.000 description 2
- 150000003077 polyols Chemical class 0.000 description 2
- 229920001451 polypropylene glycol Polymers 0.000 description 2
- 239000011527 polyurethane coating Substances 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- 238000004448 titration Methods 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- OBETXYAYXDNJHR-SSDOTTSWSA-M (2r)-2-ethylhexanoate Chemical compound CCCC[C@@H](CC)C([O-])=O OBETXYAYXDNJHR-SSDOTTSWSA-M 0.000 description 1
- UNMJLQGKEDTEKJ-UHFFFAOYSA-N (3-ethyloxetan-3-yl)methanol Chemical compound CCC1(CO)COC1 UNMJLQGKEDTEKJ-UHFFFAOYSA-N 0.000 description 1
- NLQMSBJFLQPLIJ-UHFFFAOYSA-N (3-methyloxetan-3-yl)methanol Chemical compound OCC1(C)COC1 NLQMSBJFLQPLIJ-UHFFFAOYSA-N 0.000 description 1
- NMRPBPVERJPACX-UHFFFAOYSA-N (3S)-octan-3-ol Natural products CCCCCC(O)CC NMRPBPVERJPACX-UHFFFAOYSA-N 0.000 description 1
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 1
- CQXDDVVZHUFGSJ-KVVVOXFISA-N (z)-octadec-9-enoic acid;zirconium Chemical compound [Zr].CCCCCCCC\C=C/CCCCCCCC(O)=O CQXDDVVZHUFGSJ-KVVVOXFISA-N 0.000 description 1
- VNMOIBZLSJDQEO-UHFFFAOYSA-N 1,10-diisocyanatodecane Chemical compound O=C=NCCCCCCCCCCN=C=O VNMOIBZLSJDQEO-UHFFFAOYSA-N 0.000 description 1
- ZWVMLYRJXORSEP-UHFFFAOYSA-N 1,2,6-Hexanetriol Chemical compound OCCCCC(O)CO ZWVMLYRJXORSEP-UHFFFAOYSA-N 0.000 description 1
- FKTHNVSLHLHISI-UHFFFAOYSA-N 1,2-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC=C1CN=C=O FKTHNVSLHLHISI-UHFFFAOYSA-N 0.000 description 1
- CIISBYKBBMFLEZ-UHFFFAOYSA-N 1,2-oxazolidine Chemical compound C1CNOC1 CIISBYKBBMFLEZ-UHFFFAOYSA-N 0.000 description 1
- OHTRJOZKRSVAOX-UHFFFAOYSA-N 1,3-diisocyanato-2-methylcyclohexane Chemical compound CC1C(N=C=O)CCCC1N=C=O OHTRJOZKRSVAOX-UHFFFAOYSA-N 0.000 description 1
- OVBFMUAFNIIQAL-UHFFFAOYSA-N 1,4-diisocyanatobutane Chemical compound O=C=NCCCCN=C=O OVBFMUAFNIIQAL-UHFFFAOYSA-N 0.000 description 1
- CDMDQYCEEKCBGR-UHFFFAOYSA-N 1,4-diisocyanatocyclohexane Chemical compound O=C=NC1CCC(N=C=O)CC1 CDMDQYCEEKCBGR-UHFFFAOYSA-N 0.000 description 1
- OUJCKESIGPLCRN-UHFFFAOYSA-N 1,5-diisocyanato-2,2-dimethylpentane Chemical compound O=C=NCC(C)(C)CCCN=C=O OUJCKESIGPLCRN-UHFFFAOYSA-N 0.000 description 1
- DFPJRUKWEPYFJT-UHFFFAOYSA-N 1,5-diisocyanatopentane Chemical compound O=C=NCCCCCN=C=O DFPJRUKWEPYFJT-UHFFFAOYSA-N 0.000 description 1
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Abstract
本发明涉及亚氨基噁二嗪二酮多异氰酸酯,具体涉及用于制备多异氰酸酯的方法,其包括在钛、锆和/或铪的单-或多核配合物作为催化剂存在下使异氰酸酯组分反应得到具有的亚氨基噁二嗪二酮基团含量基于异氰脲酸酯与亚氨基噁二嗪二酮基团总量计≥20mol%的多异氰酸酯。本发明还提供了通过根据本发明的方法可得的多异氰酸酯和通过使所述多异氰酸酯分别与至少一种羟基官能或氨基官能的组分反应可得的聚氨酯和聚脲。
Description
技术领域
本发明涉及用于制备多异氰酸酯的方法。本发明进一步涉及通过所述方法可得的多异氰酸酯和由所述多异氰酸酯可得的聚氨酯和聚脲。
背景技术
用于制备具有高含量脲基甲酸酯和异氰脲酸酯基团的多异氰酸酯的方法公开在JP-A
61-151179中。使用的反应催化剂例如是丁醇锆。
JP-A
61-151179没有描述在所述多异氰酸酯中具有高含量亚氨基噁二嗪二酮基团的多异氰酸酯。然而,该类多异氰酸酯是有利的,因为它们显示出非常低的粘度结合高的异氰酸酯官能度和例如适合用于涂敷体系。
HDI通过催化低聚作用的不对称三聚体合成是众所周知的和可以通过使用(多)氟化氢(EP-A 0789 299),尤其是四烷基铵-或四烷基鏻-多氟化氢(EP-A 0896 009和EP-A
0 962 455)作为催化剂进行。
这些催化剂不是市购可得的且难以制备。其合成要求使用有毒且非常腐蚀性的氢氟酸并且只能通过使用特殊的反应器和在强保护下进行。
另外,在不含溶剂的形式中这些催化剂是固体的且在它们可以用于异氰酸酯的三聚反应之前必须溶解在合适的溶剂中。通常使用低分子的单醇作为溶剂。低用量的工业规模的催化剂的高浓缩溶液的计量是困难的。但是如果使用多氟化物作为催化剂,则使用的溶剂的量必须尽可能低,因为在羟基存在下与不对称三聚体形成有关的选择性降低非常多,使得形成亚氨基噁二嗪二酮基团的趋势明显降低。
发明内容
本发明的目的是提供用于制备具有高含量亚氨基噁二嗪二酮基团的多异氰酸酯的方法。
在根据本发明的方法中此目的通过如下实现:在钛、锆和/或铪的单-或多核配合物作为催化剂存在下使异氰酸酯组分反应得到具有的亚氨基噁二嗪二酮基团含量基于异氰脲酸酯与亚氨基噁二嗪二酮基团总量计≥ 20
mol%的多异氰酸酯。
根据本发明的第一个优选的实施方案,所述配合物可以包含至少一个选自钛、锆和铪的中心原子M,其中一个或多个配体与所述中心原子M经由元素周期表的第15和/或16族元素配位,优选经氮、氧和/或硫和更优选经氧配位。这些配合物的一个优点在于它们制备简单。
这里,特别优选使用通式(I)的至少一种醇盐作为催化剂,
其中
M是钛、锆或铪,
R1、R2、R3和R4是相同或不同的基团和各自为饱和的或不饱和的、线性的或支化的、任选地取代的脂族、环脂族、芳族或芳脂族,优选脂族或环脂族基团,其可包含1-18个碳原子,优选1-8个碳原子,和任选地最多3个选自氧、硫、氮的杂原子,优选最多3个氧原子,和其中R1、R2、R3和R4也可以相互以任意组合与M和至少两个氧原子和任选地另外氮原子或氧原子一起形成具有3-6个碳原子的杂环。
可用作催化剂的醇盐的实例包括:四甲醇钛、四乙醇钛、四正丙醇钛、四异丙醇钛、四正丁醇钛、四异丁醇钛、四仲丁醇钛、四叔丁醇钛、四-2-乙基己醇钛、四辛醇钛、四环己醇钛、四硬质醇钛、四(甲氧基乙醇)钛、四(乙氧基乙醇)钛、四苯甲醇钛、四苯酚钛、四甲醇锆、四乙醇锆、四正丙醇锆、四异丙醇锆、四正丁醇锆、四叔丁醇锆、四-2-甲基-2-丁醇锆、四-2-乙基己醇锆、四-2-甲氧基甲基-2-丙醇锆、四苯酚锆、四甲醇铪、四乙醇铪、四正丙醇铪、四异丙醇铪、四正丁醇铪、四叔丁醇铪、四-2-甲基-2-甲氧基丙醇铪、四-2,2-二乙基丙醇铪、四-2-乙基己醇铪和/或四辛醇铪。优选可用的是四正丁醇钛、四乙醇锆、四正丁醇锆、四-2-乙基己醇锆、四乙醇铪、四正丁醇铪和/或四-2-乙基己醇铪。
根据另一个优选的实施方案,使用通式(II)或(III)的至少一种羧酸盐作为催化剂,
其中
M是钛、锆或铪,
R5、R6、R7和R8是相同或不同的基团和各自是饱和或不饱和的、线性或支化的脂族或环脂族的、任选地取代的芳族或芳脂族基团,其可包含1-18个碳原子和任选地最多3个选自氧、硫、氮的杂原子,优选是相同或不同的基团和各自是饱和的或不饱和的、线性或支化的脂族或环脂族基团,其可包含1-18个碳原子和任选地最多3个选自氧、硫、氮的杂原子,和更优选是相同的基团和各自是饱和的或不饱和的、线性或支化的脂族或环脂族基团,其可包含1-8个碳原子和任选地最多3个氧原子,和其中式(II)中R5、R6、R7和R8和式(III)中R5和R6
也可以相互以任意组合与M和至少两个氧原子和任选地另外氮原子或氧原子一起形成具有3-6个碳原子的杂环,和优选可以与M和两个氧原子一起形成具有2或3个碳原子的杂环。
特别优选的通式(II)的羧酸盐是:四-2-乙基己酸钛、四硬脂酸钛、四丙烯酸钛、四苯甲酸钛、四乙酸锆、四丙酸锆、四丁酸锆、四辛酸锆、四-2-乙基己酸锆、四新癸酸锆、四硬脂酸锆、草酸锆、羟基乙酸锆、乳酸锆、四丙烯酸锆、四甲基丙烯酸锆、四环烷酸锆、四乙酸铪、草酸铪、四辛酸铪、 四-2-乙基己酸铪和/或四新癸酸铪。
特别优选的通式(III)的羧酸盐是:乙酸钛、丙酸钛、丁酸钛、戊酸钛、己酸钛、2-乙基己酸钛、辛酸钛、乙酸锆、辛酸锆、癸酸锆、十二烷酸锆、十四烷酸锆、十五烷酸锆、硬脂酸锆、二甲基丙烯酸锆、环戊烷甲酸锆、环己烷甲酸锆、亚油酸锆、亚麻酸锆、油酸锆、苯甲酸锆和/或二苯基乙酸锆。
通常,这里使用的催化剂的一大优点是它们是容易处理的无害化合物。
所述催化剂基于所述异氰酸酯组分计通常以0.0005重量%-2.0重量%,优选0.0010重量%-1.0重量%和更优选0.0015重量%-0.5重量%的量使用。所述催化剂可以本体使用。这具有的优点是由于不使用任何催化剂溶剂而使获得的多异氰酸酯不包含杂质。
然而,所述催化剂也可以作为所述催化剂与催化剂溶剂,优选与有机催化剂溶剂的混合物使用。这里,所述催化剂溶液的稀释倍数可以在非常宽的限度内自由选择。具有0.01重量%以上浓度的溶液是催化活性的。
有用的催化剂溶剂是,例如异氰酸酯惰性的溶剂,例如己烷、甲苯、二甲苯、氯苯、乙酸乙酯、乙酸丁酯、二乙二醇二甲醚、二丙二醇二甲醚、乙二醇单甲基或单乙基醚乙酸酯、二乙二醇乙基和丁基醚乙酸酯、丙二醇单甲基醚乙酸酯、2-乙酸1-甲氧基丙基酯、乙酸3-甲氧基-正丁基酯、二乙酸丙二醇酯、丙酮、甲基乙基酮、甲基异丁基酮、环己酮、内酯如ß-丙内酯、γ-丁内酯、ε-己内酯和ε-甲基己内酯,而且还有溶剂如N-甲基吡咯烷酮和N-甲基己内酰胺、碳酸1,2-亚丙基酯、二氯甲烷、二甲基亚砜、磷酸三乙酯或该类溶剂的任何需要的混合物。
在根据本发明的方法中,优选使用带有异氰酸酯反应性基团的和可以被引入到所述多异氰酸酯中的催化剂溶剂。该类溶剂的实例是一元-或多元简单的醇,例如甲醇、乙醇、正丙醇、异丙醇、正丁醇、正己醇、2-乙基-1-己醇、乙二醇、丙二醇、异构的丁二醇、2-乙基-1,3-己二醇或甘油;醚醇,例如1-甲氧基-2-丙醇、3-乙基-3-羟基甲基氧杂环丁烷、四氢糠醇、乙二醇单甲醚、乙二醇单乙醚、乙二醇单丁醚、二乙二醇单甲醚、二乙二醇单乙醚、二乙二醇单丁醚、二乙二醇、二丙二醇或液态较高分子量的聚乙二醇、聚丙二醇、混合的聚乙二醇/聚丙二醇及其单烷基醚;酯醇,例如乙二醇单乙酸酯、丙二醇单月硅酸酯、甘油单-和二乙酸酯、甘油单丁酸酯或2,2,4-三甲基-1,3-戊二醇单异丁酸酯;不饱和醇,例如烯丙醇、1,1-二甲基烯丙醇或油醇;芳脂族醇,例如苯甲醇;N-单取代的酰胺,例如N-甲基甲酰胺、N-甲基乙酰胺、氰基乙酰胺或2-吡咯烷酮或该类溶剂的任何需要的混合物。
就所述异氰酸酯组分而言,使用的所述异氰酸酯组分优选是至少一种脂族、环脂族或芳脂族异氰酸酯,优选是至少一种脂族或芳脂族二异氰酸酯。所述异氰酸酯组分可以通过任何需要的方法制备,例如通过光气化或通过不含光气的线路,例如通过氨基甲酸酯分裂制备。
可用作所述异氰酸酯组分的化合物包括,例如分子量范围在140-400g/mol的那些,例如1,4-二异氰酸根合丁烷、1,5-二异氰酸根合戊烷、1,6-二异氰酸根合己烷(HDI)、1,5-二异氰酸根合-2,2-二甲基戊烷、2,2,4-和2,4,4-三甲基-1,6-二异氰酸根合己烷、1,10-二异氰酸根合癸烷、1,3-和1,4-二异氰酸根合环己烷、1,4-二异氰酸根合-3,3,5-三甲基环己烷、1,3-二异氰酸根合-2-甲基环己烷、1,3-二异氰酸根合-4-甲基环己烷、1-异氰酸根合-3,3,5-三甲基-5-异氰酸根合甲基环己烷(异佛尔酮二异氰酸酯;IPDI)、1-异氰酸根合-1-甲基-4(3)-异氰酸根合甲基环己烷、2,4'-和4,4'-二异氰酸根合二环己基甲烷、1,3-和1,4-双(异氰酸根合甲基)环己烷、4,4'-二异氰酸根合-3,3'-二甲基二环己基甲烷、4,4'-二异氰酸根合-3,3',5,5'-四甲基二环己基甲烷、4,4'-二异氰酸根合-1,1'-二(环己基)、4,4'-二异氰酸根合-3,3'-二甲基-1,1'-二(环己基)、4,4'-二异氰酸根合-2,2',5,5'-四甲基-1,1'-二(环己基)、1,8-二异氰酸根合-对-薄荷烷、1,3-二异氰酸根合金刚烷、1,3-二甲基-5,7-二异氰酸根合金刚烷、1,3-和1,4-双(异氰酸根合甲基)苯(苯二亚甲基二异氰酸酯;XDI), 1,3-和1,4-双(1-异氰酸根合-1-甲基乙基)苯(TMXDI)和双(4-(1-异氰酸根合-1-甲基乙基)苯基)碳酸酯和该类二异氰酸酯的任何需要的混合物。另外同样可用的二异氰酸酯另外例如在Justus Liebigs Annalen der Chemie,第562(1949)卷,第75-136页中可找到。
非常特别优选使用的所述异氰酸酯组分是至少1,6-二异氰酸根合己烷、1,3-或1,4-双(异氰酸根合甲基)苯,其中1,6-二异氰酸根合己烷是尤其优选的。
在本发明的研发中,所述异氰酸酯组分与羟基官能的组分混合和在所述催化剂存在下反应得到所述多异氰酸酯。
在一个优选的实施方案中,使用的所述羟基官能的组分包含基于所述异氰酸酯组分计最多0.0049重量%的酚羟基官能的化合物。
适合用作酚羟基官能的化合物的化合物例如包括如下:苯酚、异构的甲酚、2-乙基苯酚、4-乙基苯酚、4-辛基苯酚、4-叔辛基苯酚、异构的壬基苯酚、1-萘酚、2-萘酚和异构的二羟基-和/或三羟基苯。
还特别优选所述羟基官能的组分不含酚羟基官能的化合物。
在一个进一步优选的实施方案中,使用的所述羟基官能的组分包含基于所述异氰酸酯组分计最多5.0重量%,优选最多2.5重量%和更优选最多0.49重量%的脂族羟基官能的化合物。
在另一个特别优选的实施方案中,所述羟基官能的组分包含至少一种线性的或支化的、任选地取代的单-、二-或三-醇,所述醇具有1-18个碳原子,优选具有1-9个碳原子和更优选具有1-6个碳原子。
在另一个非常特别优选的实施方案中,所述羟基官能的组分由线性的或支化的、任选地取代的单-、二-或三-醇组成,所述醇具有1-18个碳原子,优选具有1-9个碳原子和更优选具有1-6个碳原子。
适合用作脂族的羟基官能的化合物的化合物例如包括如下:甲醇、乙醇、正丙醇、异丙醇、正丁醇、异丁醇、 仲丁醇、异构的戊醇、己醇、辛醇和壬醇、正癸醇、正十二烷醇、正十四烷醇、正十六烷醇、正十八烷醇、环己醇、异构的甲基环己醇、羟基甲基环己烷、3-甲基-3-羟基甲基氧杂环丁烷、1,2-乙二醇、1,2-和1,3-丙二醇、异构的丁二醇、戊二醇、己二醇、庚二醇和辛二醇、1,10-癸二醇、1,2-和1,4-环己二醇、1,4-环己烷二甲醇、4,4'-(1-甲基乙叉)双环己醇、1,2,3-丙三醇、1,1,1-三羟甲基乙烷、1,2,6-己三醇、1,1,1-三羟甲基丙烷、2,2-双(羟基甲基)-1,3-丙二醇、双(2-羟基乙基)氢醌、1,2,4-和1,3,5-三羟基环己烷或1,3,5-三(2-羟基乙基)异氰脲酸酯而且还有简单的酯醇或醚醇,例如2-羟基丙酸乙酯、2-羟基丙酸正丁酯、乙二醇单甲醚、乙二醇单乙醚、乙二醇单丁醚、二乙二醇单甲醚、二乙二醇单乙醚、二乙二醇单丁醚、新戊二醇羟基新戊酸酯、二乙二醇和二丙二醇或该类醇的任何需要的混合物。在一个优选的实施方案中,用于实施根据本发明的方法的所述异氰酸酯组分可以任选地在惰性气体例如氮气下,和任选地在溶剂存在下,在0℃-120℃,优选20℃-100℃,更优选40℃-100℃的温度下最初加入。这里,溶剂特别应当理解为是指选自前面所述的作为异氰酸酯惰性的催化剂溶剂的溶剂。
一旦已经初始加入所述异氰酸酯组分,所述催化剂或所述催化剂与所述催化剂溶剂的混合物可以以上文所述的量加入。所述催化剂在整个反应过程中可以例如借助合适的计量泵一批或多批加入或者连续加入。
还优选在加入所述催化剂之前向所述异氰酸酯组分中加入任选地使用的羟基官能的组分。
在一个进一步优选的实施方案中,使用的所述羟基官能的催化剂溶剂和脂族羟基官能的化合物合计基于所述异氰酸酯组分计最多5.0重量%,优选最多2.5重量%和更优选最多0.49重量%。
在一个进一步优选的实施方案中,所述反应在40℃-150℃,优选85℃-135℃和更优选105℃-125℃之间的温度下进行。
与反应类型无关,当使用羟基官能的组分时,所述反应通常可以进行到超出相应于完全脲基甲酸酯化的转化率至根据本发明的所述方法产物具有脲基甲酸酯基团的含量基于脲基甲酸酯、异氰脲酸酯和亚氨基噁二嗪二酮基团的总量计不超过70mol%,优选不超过60mol%,更优选不超过50%的程度。
在本发明情况下,反应混合物应当理解为是指包含所述异氰酸酯组分、所述催化剂、任何其它的起始材料和形成的所述多异氰酸酯的混合物。
在根据本发明的方法中,亚氨基噁二嗪二酮、异氰脲酸酯、脲二酮和/或脲基甲酸酯基团的比率可以例如通过所述反应混合物或所得的多异氰酸酯的NMR光谱分析测定。这里优选可以使用13C NMR光谱,优选质子去偶的,因为所述亚氨基噁二嗪二酮、异氰脲酸酯、脲二酮和/或脲基甲酸酯基团产生特征信号。
在本申请中给出的关于在根据本发明的方法的条件下形成的所述亚氨基噁二嗪二酮、异氰脲酸酯、脲二酮和/或脲基甲酸酯基团的说明(mol%)由13C NMR谱计算和各自基于所述异氰脲酸酯、亚氨基噁二嗪二酮、脲二酮和根据具体情况而定,存在的脲基甲酸酯基团的总和计。
在一个进一步优选的实施方案中,在根据本发明的方法中反应的进程通过所述反应混合物中异氰酸酯基团含量的降低进行监测。所述反应混合物中异氰酸酯基团的含量和同样通过根据本发明的方法得到的所述多异氰酸酯的异氰酸酯基团的含量可以例如通过滴定法测定。异氰酸酯基团的含量下文描述为NCO含量。
在一个进一步优选的实施方案中,所述反应进行到所述反应混合物显示10%-40%,优选15%-30%的低聚度的程度。在本发明的情况下,所述“低聚度”是在根据本发明的反应过程中消耗的在所述起始混合物中初始存在的所述异氰酸酯基团的百分比。低聚度百分比可以使用下式计算:
低聚度 = (NCO 开始 – NCO 结束) /
NCO 开始 x
100 。
所述反应可以例如在达到目标低聚度时终止。通常在30分钟-8小时,优选1-6小时的反应时间后达到此低聚度。
所述反应可以例如通过将所述反应混合物冷却到室温而终止。然而,所述反应通常通过加入催化剂毒物和接着任选地短时间加热所述反应混合物例如至超过80℃的温度而停止。
可用的催化剂毒物是,例如无机酸如盐酸、亚磷酸或磷酸、酰氯如乙酰氯、苯甲酰氯或间苯二酰氯、磺酸和磺酸酯,例如甲磺酸、对-甲苯磺酸、三氟甲磺酸、全氟丁烷磺酸、十二烷基苯磺酸、对-甲苯磺酸甲酯和对-甲苯磺酸乙酯、磷酸单烷基酯和二烷基酯如磷酸单十三烷基酯、磷酸二丁酯和磷酸二辛酯而且还有甲硅烷基化的酸如甲磺酸三甲基甲硅烷基酯、三氟甲磺酸三甲基甲硅烷基酯、磷酸三(三甲基甲硅烷基)酯和磷酸二乙基三甲基甲硅烷基酯。
停止所述反应要求的催化剂毒物的量取决于使用的催化剂的量;通常基于开始使用的催化剂计使用等量的催化剂毒物。然而,如果考虑在反应过程中可能发生的催化剂损失,基于初始使用的所述催化剂的量计甚至20-80%(以当量计)的所述催化剂毒物可能就足以停止所述反应。
提及的所述催化剂毒物可以本体使用或溶解在合适的溶剂中使用。合适的溶剂是,例如,上文作为可能的催化剂溶剂或其混合物已经描述的溶剂。所述稀释因子可以在非常宽的限度内自由选择和例如具有10重量%或以上浓度的溶液是可用的。
除了提及的溶剂之外,当所述毒物是充分的异氰酸酯惰性的并因此允许制备储存稳定的溶液的时候,在根据本发明的方法中上述异氰酸酯组分也可用作用于所述催化剂毒物的溶剂。
所述反应一旦停止,优选将所述反应混合物通过薄膜蒸发在减压下,例如在小于1.0mbar,优选小于0.5mbar,更优选小于0.2mbar的压力下,在非常温和的条件下,优选在100℃-200℃,优选120℃-180℃的温度下除去挥发性成分(过量的单体异氰酸酯组分和使用的任何溶剂)。
在根据本发明的方法的一个另外的实施方案中,提及的挥发性成分通过用合适的异氰酸酯惰性的溶剂(例如脂族或环脂族烃如戊烷、己烷、庚烷、环戊烷或环己烷)萃取而从所述多异氰酸酯中除去。
在一个进一步优选的实施方案中,所述催化剂保留在多异氰酸酯中,因为这样可以避免昂贵不方便的除去同时根据本发明的多异氰酸酯的性能保持不变且非常好。
与后处理的特征无关,所得到的根据本发明的方法的产物是透明的通常实际上无色的多异氰酸酯,其具有的亚氨基噁二嗪二酮基团含量分别基于异氰脲酸酯和亚氨基噁二嗪二酮基团的总量计为至少20mol%,优选至少25mol%,更优选至少30mol%。
还优选的是得到的所述多异氰酸酯具有的NCO含量为17.0重量%-24.5重量%,优选18.0重量%-24.0重量%,更优选20.0重量%-23.5重量%。
本发明进一步提供了通过根据本发明的方法可得的多异氰酸酯。
根据本发明的多异氰酸酯突出地可用作用于双组分聚氨酯涂料的固化剂,所述聚氨酯涂料包含常规的聚醚多元醇、聚酯多元醇、聚碳酸酯多元醇和/或聚丙烯酸酯多元醇作为用于所述多异氰酸酯的羟基官能的组分共反应物。
因为它们的低粘度,所以根据本发明的多异氰酸酯可以以不含溶剂的形式使用,但是如果要求的话也可以用常规的溶剂例如前面提及的在根据本发明的方法中任选地使用的异氰酸酯惰性的溶剂进行稀释而并无浑浊。用根据本发明的多异氰酸酯配制的涂料组合物甚至在室温干燥时通常也具有良好的涂覆性能,在所述组合物中可以任选地掺入涂料领域中常规的助剂和添加剂,例如流动性控制助剂、着色颜料、填料或消光剂。然而,它们当然也可以在强制条件下在升高的温度或通过在最高260℃的温度下烘干而干燥。
为了控制固化速率,配制所述涂料组合物时可以使用合适的催化剂,例如异氰酸酯化学中常规的催化剂,例如叔胺如三乙胺、吡啶、甲基吡啶、苄基二甲基胺、N,N-桥亚乙基哌嗪、N-甲基哌啶、五甲基二亚乙基三胺、N,N-二甲基氨基环己烷、N,N'-二甲基哌嗪或金属盐如氯化铁(III)、氯化锌、2-乙基己酸锌、辛酸锌(II)、乙基己酸锌(II)、二月桂基二丁基锡(IV)、2-乙基己酸铋(III)、辛酸铋(III)或羟基乙酸钼。
根据本发明的多异氰酸酯在制备水性双组分聚氨酯体系中也可用作用于具有异氰酸酯反应性基团特别是醇羟基基团的粘结剂或粘结剂组分在水中的溶液或悬浮液的交联剂组分。考虑它们的低粘度,它们可以原样使用,即:以疏水的形式使用,或者以通过例如根据EP-B
0 540 985、EP-B 0 959 087或EP-B 1 287 052已知的方法亲水改性的形式使用。
在一个优选的实施方案中,所述多异氰酸酯的部分或全部的异氰酸酯基团可已经与至少一种封端剂反应。
这些封端剂特别是本身由聚氨酯化学已知的封端剂,例如丙二酸二乙酯、乙酰乙酸乙酯、活化的环状酮例如环戊酮、2-羧甲基酯和-羧乙基酯、丙酮肟、丁酮肟、ε-己内酰胺、3,5-二甲基吡唑、1,2,4-三唑、二甲基-1,2,4-三唑、咪唑、苄基-叔丁基胺或这些封端剂的任何需要的混合物。
根据本发明的多异氰酸酯也可以与多胺组合,例如由EP-B 0 403 921已知的聚天冬氨酸衍生物或者其胺基团以封端形式存在的类型的多胺,例如聚酮亚胺、聚醛亚胺或噁唑仑(oxazolane)。在水分的影响下,这些封端的氨基形成游离的氨基和在噁唑仑的情况下,还有游离的羟基,它们通过交联与根据本发明的多异氰酸酯的异氰酸酯基团反应。
在封端的形式下,根据本发明的多异氰酸酯也可以与上面提及的涂料粘结剂或涂料粘结剂组分组合作为单组分PU烘焙体系使用。
所有的涂料组合物均以这样的量包含所述多异氰酸酯及其共反应物,所述量使得对于每个任选地封端的异氰酸酯基团来说存在0.5-3,优选0.6-2.0,更优选0.8-1.6的任选地封端的异氰酸酯反应性的基团。然而,根据本发明的多异氰酸酯也可任选地以很少量与非官能的涂料粘结剂混合以实现非常特定的性能,例如作为增粘的添加剂。
借助根据本发明的多异氰酸酯配制的涂料可以与任何基材一起使用,例如金属、木材、玻璃、石头、陶瓷材料、混凝土、硬质和柔性塑料、纺织物、皮革和纸张,在涂敷之前所述基材也可以任选地带有常规的底漆。
除了作为用于不含溶剂、含溶剂或水性的2K PU涂料的交联组分的优选用途之外,根据本发明的多异氰酸酯还突出地可用作不含溶剂或含溶剂的粘合剂或水性分散粘合剂的交联剂或者作为用于制备耐光的致密或发泡的聚氨酯成型体的合成组分。
因此,本发明进一步提供了通过使根据本发明的多异氰酸酯与至少一种羟基官能的组分反应可得的聚氨酯。
所述羟基官能的组分优选选自聚丙烯酸酯,即:(甲基)丙烯酸烷基酯的聚合物或任选地与苯乙烯或其它可共聚的烯属不饱和单体的共聚物。
本发明还进一步提供了通过使根据本发明的多异氰酸酯与至少一种氨基官能的组分反应可得的聚脲。
有用的氨基官能的组分特别是聚天冬氨酸,其例如通过EP-B 0 403 921的方法通过二胺与富马酸或马来酸酯反应可得。
下文参考实施例更特别地描述本发明。
具体实施方式
除非另外说明,所有的百分比都是重量百分比。
所述NCO含量根据DIN EN ISO 11909通过滴定法测定。
所述残余单体含量通过气相色谱用内标根据DIN EN ISO 10283测量。
所有的粘度测量都用Anton Paar Germany GmbH (DE)的Physica MCR 51流变仪根据DIN EN ISO 3219进行。
在根据本发明的方法的条件下形成的所述亚氨基噁二嗪二酮、异氰脲酸酯、脲二酮和/或脲基甲酸酯基团的含量(mol%)由积分的质子去偶13C NMR谱(在Bruker
DPX-400仪器上获得)计算和分别基于存在的所述异氰脲酸酯、亚氨基噁二嗪二酮、脲二酮和根据具体情况而定可能存在的脲基甲酸酯基团的总和计。所述每个结构要素具有下面的化学位移(以ppm表示):亚氨基噁二嗪二酮:147.8, 144.3和135.3;异氰脲酸酯:148.4;脲二酮:157.1;脲基甲酸酯:155.7和153.8。
实施例1 (本发明)
最初在115℃的温度在干燥的氮气下在搅拌下加入840 g
(5 mol)六亚甲基二异氰酸酯(HDI)并每次与0.04g作为催化剂的四正丁醇锆分别以大约40分钟的间隔混合四次。在每次催化剂添加之后立刻就可以观察到导致所述反应混合物短时间内加热至最高达118-119℃的快速降低的放热。在加入最后量的催化剂之后,所述混合物在115℃下进一步搅拌2小时直到已经达到42.5%的NCO含量。然后通过加入间苯二酰氯在HDI中的0.5g 10%浓度的溶液并随后搅拌15分钟使所述催化剂失活。最后,所述未转化的单体HDI在薄层蒸发器中在130℃的温度和0.1mbar的压力下分离出来。得到实际上无色的透明多异氰酸酯混合物,所述混合物具有下面的特征和组成:
NCO含量:
22.7%
单体HDI:
0.09%
粘度(23℃):
1450 mPas
亚氨基噁二嗪二酮基团: 32.8 mol%
异氰脲酸酯基团:
64.2 mol%
脲二酮基团:
3.0 mol%
亚氨基噁二嗪二酮/异氰脲酸酯:33.8:66.2。
实施例2 (本发明)
根据实施例1中描述的方法,通过分批加入总计0.2g的四-2-乙基己醇锆使840 g
(5 mol)HDI反应。如实施例1中描述在43.8%的NCO含量用1.4g 10%浓度的间苯二酰氯在HDI中的溶液终止反应,并通过蒸馏将所述反应混合物进行后处理。得到实际上无色的透明多异氰酸酯混合物,所述混合物具有下面的特征和组成:
NCO含量:
23.1%
单体HDI:
0.22%
粘度(23℃):
840 mPas
亚氨基噁二嗪二酮基团: 37.5 mol%
异氰脲酸酯基团:
60.4 mol%
脲二酮基团:
2.1 mol%
亚氨基噁二嗪二酮/异氰脲酸酯:38.3:61.7。
实施例3 (本发明)
根据实施例1中描述的方法,通过分批加入总计0.8 g的四乙醇锆在氯苯中的10%浓度的溶液使840 g (5 mol)HDI反应。如实施例1中描述在41.8%的NCO含量用0.6g 10%浓度的间苯二酰氯在HDI中的溶液终止反应,并通过蒸馏将所述反应混合物进行后处理。得到实际上无色的透明多异氰酸酯混合物,所述混合物具有下面的特征和组成:
NCO含量:
22.2%
单体HDI:
0.15%
粘度(23℃):
1950 mPas
亚氨基噁二嗪二酮基团: 20.4 mol%
异氰脲酸酯基团:
75.4 mol%
脲二酮基团:
4.2 mol%
亚氨基噁二嗪二酮/异氰脲酸酯:21.3:78.7。
实施例4 (本发明)
根据实施例1中描述的方法,通过分批加入总计0.24
g的四-正丁醇钛使840 g (5 mol)HDI反应。如实施例1中描述在44.5%的NCO含量用0.8g 10%浓度的间苯二酰氯在HDI中的溶液终止反应,并通过蒸馏将所述反应混合物进行后处理。得到黄色透明多异氰酸酯混合物,所述混合物具有下面的特征和组成:
NCO含量:
23.2%
单体HDI:
0.14%
粘度(23℃):
1070 mPas
亚氨基噁二嗪二酮基团: 20.1 mol%
异氰脲酸酯基团:
76.2 mol%
脲二酮基团:
3.7 mol%
亚氨基噁二嗪二酮/异氰脲酸酯:20.9:79.1。
实施例5 (本发明)
根据实施例1中描述的方法,通过分批加入总计0.2 g的四-正丁醇铪使840 g
(5 mol)HDI反应。如实施例1中描述在44.9%的NCO含量用1.1 g 10%浓度的间苯二酰氯在HDI中的溶液终止反应,并通过蒸馏将所述反应混合物进行后处理。得到无色透明的多异氰酸酯混合物,所述混合物具有下面的特征和组成:
NCO含量:
23.5%
单体HDI:
0.10%
粘度(23℃):
840 mPas
亚氨基噁二嗪二酮基团: 37.6 mol%
异氰脲酸酯基团:
59.0 mol%
脲二酮基团:
3.4 mol%
亚氨基噁二嗪二酮/异氰脲酸酯:38.9:61.1。
实施例6 (本发明)
根据实施例1中描述的方法,通过分批加入总计0.32
g的四辛酸锆使840 g (5 mol)HDI反应。如实施例1中描述在43.6%的NCO含量用1.5 g 10%浓度的间苯二酰氯在HDI中的溶液终止反应,并通过蒸馏将所述反应混合物进行后处理。得到淡黄色的透明多异氰酸酯混合物,所述混合物具有下面的特征和组成:
NCO含量:
22.0%
单体HDI:
0.23%
粘度(23℃):
1680 mPas
亚氨基噁二嗪二酮基团: 21.5 mol%
异氰脲酸酯基团:
73.6 mol%
脲二酮基团:
4.9 mol%
亚氨基噁二嗪二酮/异氰脲酸酯:22.6:77.4。
实施例7 (本发明)
根据实施例1中描述的方法,通过分批加入总计0.40
g的辛酸锆使840 g (5 mol)HDI反应。如实施例1中描述在43.2%的NCO含量用0.9 g 10%浓度的间苯二酰氯在HDI中的溶液终止反应,并通过蒸馏将所述反应混合物进行后处理。得到淡黄色的透明多异氰酸酯混合物,所述混合物具有下面的特征和组成:
NCO含量:
22.6%
单体HDI:
0.22%
粘度(23℃):
1240 mPas
亚氨基噁二嗪二酮基团: 27.0 mol%
异氰脲酸酯基团:
67.5 mol%
脲二酮基团:
5.5 mol%
亚氨基噁二嗪二酮/异氰脲酸酯:28.6:71.4。
本发明的实施例1-7显示使用钛、锆和/或铪的单-或多核配合物作为催化剂导致所述异氰酸酯组分的非常有效的反应,得到具有基于异氰脲酸酯和亚氨基噁二嗪二酮基团的总量计至少20-大于38mol%的亚氨基噁二嗪二酮基团含量的多异氰酸酯。
实施例8 (本发明 - 与含醇基团的共反应物反应)
最初在115℃的温度在干燥的氮气下在搅拌下加入840 g
(5 mol)六亚甲基二异氰酸酯(HDI)并连续地与18.5 g(0.25 mol)的正丁醇和与作为催化剂的0.2 g的四-2-乙基己醇锆混合。基于所述反应的放热,所述混合物加热到最高118℃。在放热下降(大约30分钟)之后,所述反应混合物的NCO含量为46.5%,其与完全脲基甲酸酯化反应的计算值相关。
此时将所述混合物取样和通过13C-NMR-光谱分析测定。在所述光谱中只发现了脲基甲酸酯基团(大约98mol%)和异氰脲酸酯基团(大约2mol%)的信号,但是没有氨基甲酸酯基团或不对称三聚体的信号。
所述混合物在115℃下进一步搅拌4小时直到已经达到40.4%的NCO含量。然后通过加入间苯二酰氯在HDI中的1.4 g 10%浓度的溶液并随后搅拌15分钟使所述催化剂失活。最后,所述未转化的单体HDI在薄层蒸发器中在130℃的温度和0.1mbar的压力下分离出来。得到实际上无色的透明多异氰酸酯混合物,所述混合物具有下面的特征和组成:
NCO含量:
21.1 %
单体HDI:
0.19%
粘度(23℃):
1240 mPas
亚氨基噁二嗪二酮基团: 12.1 mol%
异氰脲酸酯基团:
44.8 mol%
脲二酮基团:
2.7 mol%
脲基甲酸酯基团:
40.4 %
亚氨基噁二嗪二酮/异氰脲酸酯:21.3:78.7。
所述实施例显示在脲基甲酸酯化反应过程中低聚物的形成仅仅是副反应。只有在羟基与中间形成的氨基甲酸酯基团完全反应之后,当时仅仅是副反应的低聚反应才变为主反应并形成越来越多的异氰脲酸酯和亚氨基噁二嗪二酮基团。
Claims (15)
1.用于制备多异氰酸酯的方法,包括在钛、锆和/或铪的单-或多核配合物作为催化剂存在下使异氰酸酯组分反应得到具有的亚氨基噁二嗪二酮基团含量基于异氰脲酸酯与亚氨基噁二嗪二酮基团总量计≥ 20 mol%的多异氰酸酯。
2.根据权利要求1的方法,其特征在于:使用的所述配合物包含至少一个选自钛、锆和铪的中心原子M,其中一个或多个配体与所述中心原子M经由元素周期表的第15和/或16族元素配位,优选经氮、氧和/或硫和更优选经氧配位。
3.根据权利要求2的方法,其特征在于:使用通式(I)的至少一种醇盐作为催化剂,
其中
M是钛、锆或铪,
R1、R2、R3和R4是相同或不同的基团和各自为饱和的或不饱和的、线性的或支化的、任选地取代的脂族、环脂族、芳族或芳脂族,优选脂族或环脂族基团,其可包含1-18个碳原子,优选1-8个碳原子,和任选地最多3个选自氧、硫、氮的杂原子,优选最多3个氧原子,和其中R1、R2、R3和R4也可以相互以任意组合与M和至少两个氧原子和任选地另外氮原子或氧原子一起形成具有3-6个碳原子的杂环。
4.根据权利要求2的方法,其特征在于:使用通式(II)或(III)的至少一种羧酸盐作为催化剂,
其中
M是钛、锆或铪,
R5、R6、R7和R8是相同或不同的基团和各自是饱和或不饱和的、线性或支化的脂族或环脂族的、任选地取代的芳族或芳脂族基团,其可包含1-18个碳原子和任选地最多3个选自氧、硫、氮的杂原子,优选是相同或不同的基团和各自是饱和的或不饱和的、线性或支化的脂族或环脂族基团,其可包含1-18个碳原子和任选地最多3个选自氧、硫、氮的杂原子,和更优选是相同的基团和各自是饱和的或不饱和的、线性或支化的脂族或环脂族基团,其可包含1-8个碳原子和任选地最多3个氧原子,和其中式(II)中R5、R6、R7和R8和式(III)中R5和R6 也可以相互以任意组合与M和至少两个氧原子和任选地另外氮原子或氧原子一起形成具有3-6个碳原子的杂环,和优选可以与M和两个氧原子一起形成具有2或3个碳原子的杂环。
5.根据权利要求1-4任一项所述的方法,其特征在于:所述催化剂基于所述异氰酸酯组分计以0.0005重量%-2.0重量%,优选0.0010重量%-1.0重量%和更优选0.0015重量%-0.5重量%的量使用。
6.根据权利要求1-5任一项所述的方法,其特征在于:使用的所述异氰酸酯组分是至少一种脂族、环脂族或芳脂族异氰酸酯,优选至少一种脂族和/或芳脂族二异氰酸酯和更优选是至少1,6-二异氰酸根合己烷、1,3-或1,4-双(异氰酸根合甲基)苯。
7.根据权利要求1-6任一项所述的方法,其特征在于:所述异氰酸酯组分与羟基官能的组分混合和在所述催化剂存在下反应得到所述多异氰酸酯。
8.根据权利要求7所述的方法,其特征在于:使用的所述羟基官能的组分包含基于所述异氰酸酯组分最多0.0049重量%的酚羟基官能的化合物和优选不含酚羟基官能的化合物。
9.根据权利要求7所述的方法,其特征在于:使用的所述脂族羟基官能的化合物包含至少一种线性的或支化的、任选地取代的单-、二-或三-醇或由其组成,所述醇具有1-18个碳原子,优选具有1-9个碳原子和更优选具有1-6个碳原子。
10.根据权利要求1-9任一项所述的方法,其特征在于:所述反应在40℃-150℃,优选85℃-135℃和更优选105℃-125℃之间的温度下进行。
11.根据权利要求1-10任一项所述的方法,其特征在于:所述催化剂保留在所述多异氰酸酯中。
12.根据权利要求1-11任一项所述的方法可得的多异氰酸酯。
13.根据权利要求12所述的多异氰酸酯,其特征在于:所述多异氰酸酯的部分或全部的异氰酸酯基团已经与至少一种封端剂反应。
14.聚氨酯,其通过使根据权利要求12和13之一的多异氰酸酯与至少一种羟基官能的组分反应可得。
15.聚脲,其通过使根据权利要求12和13之一的多异氰酸酯与至少一种氨基官能的组分反应可得。
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CN104693414B (zh) | 2022-07-08 |
EP2883895A1 (de) | 2015-06-17 |
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US9926402B2 (en) | 2018-03-27 |
US20150158966A1 (en) | 2015-06-11 |
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