CN113574129A - 聚氨酯水分散体以及涂布剂 - Google Patents
聚氨酯水分散体以及涂布剂 Download PDFInfo
- Publication number
- CN113574129A CN113574129A CN202080021174.XA CN202080021174A CN113574129A CN 113574129 A CN113574129 A CN 113574129A CN 202080021174 A CN202080021174 A CN 202080021174A CN 113574129 A CN113574129 A CN 113574129A
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- CN
- China
- Prior art keywords
- mass
- urethane prepolymer
- polyol
- parts
- aqueous polyurethane
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
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- 229920003009 polyurethane dispersion Polymers 0.000 title claims abstract description 45
- 239000011248 coating agent Substances 0.000 title claims abstract description 19
- 229920005862 polyol Polymers 0.000 claims abstract description 69
- 150000003077 polyols Chemical class 0.000 claims abstract description 68
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims abstract description 62
- 229920002635 polyurethane Polymers 0.000 claims abstract description 43
- 239000004814 polyurethane Substances 0.000 claims abstract description 43
- 239000005056 polyisocyanate Substances 0.000 claims abstract description 33
- 229920001228 polyisocyanate Polymers 0.000 claims abstract description 30
- 239000004970 Chain extender Substances 0.000 claims abstract description 24
- 239000004202 carbamide Substances 0.000 claims abstract description 13
- 238000004132 cross linking Methods 0.000 claims abstract description 11
- 239000006185 dispersion Substances 0.000 claims abstract description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000002253 acid Substances 0.000 claims description 18
- 229920005906 polyester polyol Polymers 0.000 claims description 10
- 150000002009 diols Chemical class 0.000 claims description 9
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 8
- 229920000515 polycarbonate Polymers 0.000 claims description 8
- 239000004417 polycarbonate Substances 0.000 claims description 8
- 229920000570 polyether Polymers 0.000 claims description 8
- 125000000129 anionic group Chemical group 0.000 claims description 5
- 229920000768 polyamine Polymers 0.000 claims description 5
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 abstract description 11
- 238000000576 coating method Methods 0.000 abstract description 7
- 230000000704 physical effect Effects 0.000 abstract description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 29
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 20
- -1 cyclic ester compound Chemical class 0.000 description 14
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 13
- 150000001875 compounds Chemical class 0.000 description 12
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 12
- 239000002904 solvent Substances 0.000 description 12
- 125000000524 functional group Chemical group 0.000 description 10
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 9
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 8
- 239000002994 raw material Substances 0.000 description 8
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 7
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 7
- 239000003431 cross linking reagent Substances 0.000 description 7
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 7
- UNVGBIALRHLALK-UHFFFAOYSA-N 1,5-Hexanediol Chemical compound CC(O)CCCCO UNVGBIALRHLALK-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 6
- GHLKSLMMWAKNBM-UHFFFAOYSA-N dodecane-1,12-diol Chemical compound OCCCCCCCCCCCCO GHLKSLMMWAKNBM-UHFFFAOYSA-N 0.000 description 6
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- XSMIOONHPKRREI-UHFFFAOYSA-N undecane-1,11-diol Chemical compound OCCCCCCCCCCCO XSMIOONHPKRREI-UHFFFAOYSA-N 0.000 description 6
- 229940043375 1,5-pentanediol Drugs 0.000 description 5
- PTBDIHRZYDMNKB-UHFFFAOYSA-N 2,2-Bis(hydroxymethyl)propionic acid Chemical compound OCC(C)(CO)C(O)=O PTBDIHRZYDMNKB-UHFFFAOYSA-N 0.000 description 5
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 5
- ALQSHHUCVQOPAS-UHFFFAOYSA-N Pentane-1,5-diol Chemical compound OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 0.000 description 5
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 5
- 125000002723 alicyclic group Chemical group 0.000 description 5
- 125000001931 aliphatic group Chemical group 0.000 description 5
- 125000002947 alkylene group Chemical group 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 4
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 4
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 4
- 229940035437 1,3-propanediol Drugs 0.000 description 4
- QWGRWMMWNDWRQN-UHFFFAOYSA-N 2-methylpropane-1,3-diol Chemical compound OCC(C)CO QWGRWMMWNDWRQN-UHFFFAOYSA-N 0.000 description 4
- SXFJDZNJHVPHPH-UHFFFAOYSA-N 3-methylpentane-1,5-diol Chemical compound OCCC(C)CCO SXFJDZNJHVPHPH-UHFFFAOYSA-N 0.000 description 4
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical class C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 4
- 235000019437 butane-1,3-diol Nutrition 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000011247 coating layer Substances 0.000 description 4
- 238000011156 evaluation Methods 0.000 description 4
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 4
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 4
- 230000003472 neutralizing effect Effects 0.000 description 4
- OEIJHBUUFURJLI-UHFFFAOYSA-N octane-1,8-diol Chemical compound OCCCCCCCCO OEIJHBUUFURJLI-UHFFFAOYSA-N 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 4
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 4
- 229960004063 propylene glycol Drugs 0.000 description 4
- 235000013772 propylene glycol Nutrition 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 4
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 4
- 229940083957 1,2-butanediol Drugs 0.000 description 3
- ALVZNPYWJMLXKV-UHFFFAOYSA-N 1,9-Nonanediol Chemical compound OCCCCCCCCCO ALVZNPYWJMLXKV-UHFFFAOYSA-N 0.000 description 3
- LCZVSXRMYJUNFX-UHFFFAOYSA-N 2-[2-(2-hydroxypropoxy)propoxy]propan-1-ol Chemical compound CC(O)COC(C)COC(C)CO LCZVSXRMYJUNFX-UHFFFAOYSA-N 0.000 description 3
- DSKYSDCYIODJPC-UHFFFAOYSA-N 2-butyl-2-ethylpropane-1,3-diol Chemical compound CCCCC(CC)(CO)CO DSKYSDCYIODJPC-UHFFFAOYSA-N 0.000 description 3
- SDQROPCSKIYYAV-UHFFFAOYSA-N 2-methyloctane-1,8-diol Chemical compound OCC(C)CCCCCCO SDQROPCSKIYYAV-UHFFFAOYSA-N 0.000 description 3
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- UWHCKJMYHZGTIT-UHFFFAOYSA-N Tetraethylene glycol, Natural products OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 3
- YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 description 3
- 239000001361 adipic acid Substances 0.000 description 3
- 235000011037 adipic acid Nutrition 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- BMRWNKZVCUKKSR-UHFFFAOYSA-N butane-1,2-diol Chemical compound CCC(O)CO BMRWNKZVCUKKSR-UHFFFAOYSA-N 0.000 description 3
- OWBTYPJTUOEWEK-UHFFFAOYSA-N butane-2,3-diol Chemical compound CC(O)C(C)O OWBTYPJTUOEWEK-UHFFFAOYSA-N 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- FOTKYAAJKYLFFN-UHFFFAOYSA-N decane-1,10-diol Chemical compound OCCCCCCCCCCO FOTKYAAJKYLFFN-UHFFFAOYSA-N 0.000 description 3
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 3
- 229940113120 dipropylene glycol Drugs 0.000 description 3
- 235000011187 glycerol Nutrition 0.000 description 3
- SXCBDZAEHILGLM-UHFFFAOYSA-N heptane-1,7-diol Chemical compound OCCCCCCCO SXCBDZAEHILGLM-UHFFFAOYSA-N 0.000 description 3
- OHMBHFSEKCCCBW-UHFFFAOYSA-N hexane-2,5-diol Chemical compound CC(O)CCC(C)O OHMBHFSEKCCCBW-UHFFFAOYSA-N 0.000 description 3
- 239000012948 isocyanate Substances 0.000 description 3
- 150000002513 isocyanates Chemical class 0.000 description 3
- CRVGTESFCCXCTH-UHFFFAOYSA-N methyl diethanolamine Chemical compound OCCN(C)CCO CRVGTESFCCXCTH-UHFFFAOYSA-N 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 125000000542 sulfonic acid group Chemical group 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- FKTHNVSLHLHISI-UHFFFAOYSA-N 1,2-bis(isocyanatomethyl)benzene Chemical class O=C=NCC1=CC=CC=C1CN=C=O FKTHNVSLHLHISI-UHFFFAOYSA-N 0.000 description 2
- CDMDQYCEEKCBGR-UHFFFAOYSA-N 1,4-diisocyanatocyclohexane Chemical compound O=C=NC1CCC(N=C=O)CC1 CDMDQYCEEKCBGR-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
- WMYINDVYGQKYMI-UHFFFAOYSA-N 2-[2,2-bis(hydroxymethyl)butoxymethyl]-2-ethylpropane-1,3-diol Chemical compound CCC(CO)(CO)COCC(CC)(CO)CO WMYINDVYGQKYMI-UHFFFAOYSA-N 0.000 description 2
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical compound C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 2
- HVBSAKJJOYLTQU-UHFFFAOYSA-N 4-aminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
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- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- OPKOKAMJFNKNAS-UHFFFAOYSA-N N-methylethanolamine Chemical compound CNCCO OPKOKAMJFNKNAS-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 2
- KXBFLNPZHXDQLV-UHFFFAOYSA-N [cyclohexyl(diisocyanato)methyl]cyclohexane Chemical compound C1CCCCC1C(N=C=O)(N=C=O)C1CCCCC1 KXBFLNPZHXDQLV-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 238000005452 bending Methods 0.000 description 2
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 2
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 125000002091 cationic group Chemical group 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 150000004985 diamines Chemical class 0.000 description 2
- 239000000539 dimer Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 239000003999 initiator Substances 0.000 description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
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- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 229920000139 polyethylene terephthalate Polymers 0.000 description 2
- 239000005020 polyethylene terephthalate Substances 0.000 description 2
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- WHOZNOZYMBRCBL-OUKQBFOZSA-N (2E)-2-Tetradecenal Chemical compound CCCCCCCCCCC\C=C\C=O WHOZNOZYMBRCBL-OUKQBFOZSA-N 0.000 description 1
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- ZWVMLYRJXORSEP-UHFFFAOYSA-N 1,2,6-Hexanetriol Chemical compound OCCCCC(O)CO ZWVMLYRJXORSEP-UHFFFAOYSA-N 0.000 description 1
- ZZXUZKXVROWEIF-UHFFFAOYSA-N 1,2-butylene carbonate Chemical compound CCC1COC(=O)O1 ZZXUZKXVROWEIF-UHFFFAOYSA-N 0.000 description 1
- VGHSXKTVMPXHNG-UHFFFAOYSA-N 1,3-diisocyanatobenzene Chemical compound O=C=NC1=CC=CC(N=C=O)=C1 VGHSXKTVMPXHNG-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- PXGZQGDTEZPERC-UHFFFAOYSA-N 1,4-cyclohexanedicarboxylic acid Chemical compound OC(=O)C1CCC(C(O)=O)CC1 PXGZQGDTEZPERC-UHFFFAOYSA-N 0.000 description 1
- ALQLPWJFHRMHIU-UHFFFAOYSA-N 1,4-diisocyanatobenzene Chemical compound O=C=NC1=CC=C(N=C=O)C=C1 ALQLPWJFHRMHIU-UHFFFAOYSA-N 0.000 description 1
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
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- C08G18/4238—Polycondensates having carboxylic or carbonic ester groups in the main chain containing only aliphatic groups derived from dicarboxylic acids and dialcohols
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
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- 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
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- C08G18/0823—Manufacture of polymers containing ionic or ionogenic groups containing anionic or anionogenic groups containing carboxylate salt groups or groups forming them
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- 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
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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Abstract
本发明提供一种可获得各种物性平衡优异、特别是自修复性优异的涂膜的聚氨酯水分散体以及含有该聚氨酯水分散体的涂布剂。本发明的聚氨酯水分散体是将使氨基甲酸酯预聚物(A)与扩链剂(B)反应而得到的聚氨酯(C)分散在水中而成,所述氨基甲酸酯预聚物(A)通过使多异氰酸酯(a)、多元醇(b)以及具有亲水性基团的多元醇(c)反应而得到,其中,所述氨基甲酸酯预聚物(A)的重均分子量为2000以上且30000以下,所述聚氨酯(C)的交联度为0.03mol/kg以上且0.15mol/kg以下,所述聚氨酯(C)的脲量为0.5mol/kg以下。
Description
相关申请的交叉引用
本申请以2019年3月26日提出的日本专利申请第2019-057542号为基础,并通过引用将其记载内容并入本文。
技术领域
本发明涉及聚氨酯水分散体以及涂布剂。
背景技术
聚氨酯水分散体广泛用作涂料及涂布剂的原料,例如航空器、汽车等的内外装饰用、住宅的外壁面及地板材料等的涂料、涂布剂的原料。因此,对于聚氨酯水分散体,根据其使用的用途及目的等而要求得到具备各种特性(例如硬度、强度、耐久性等)的涂膜。
例如,在专利文献1中,作为能够得到耐油性、耐水解性、耐候性、弯曲加工性、自修复性优异的涂膜的水分散性氨基甲酸酯预聚物以及树脂,公开了如下的水分散性氨基甲酸酯预聚物,即,为(a)有机异氰酸酯、(b)聚碳酸酯二醇和(c)具有一个亲水性中心与至少两个异氰酸酯反应性基团的化合物的反应生成物,其中,聚碳酸酯二醇(b)的规定的三种重复单元为规定的比率(摩尔比),末端伯羟基比率为95%~99.5%。
现有技术文献
专利文献
专利文献1:日本特开2013-18805号公报
发明内容
发明欲解决的技术问题
然而,虽然能够得到耐油性、耐水解性、耐候性、柔软性等物性平衡优异的涂膜,但是尚不存在能够得到具有足够的弯曲加工性及自修复性的涂膜的聚氨酯水分散体。
本发明是基于以上情况而完成,其课题在于,提供一种能够得到各种物性平衡优异、特别是自修复性优异的涂膜的聚氨酯水分散体以及含有该聚氨酯水分散体的涂布剂。
用于解决问题的技术手段
本发明包括以下[1]至[13]。
[1]一种聚氨酯水分散体,其特征在于,上述聚氨酯水分散体为将使氨基甲酸酯预聚物(A)与扩链剂(B)反应而得到的聚氨酯(C)分散于水中而成,上述氨基甲酸酯预聚物(A)通过使多异氰酸酯(a)、多元醇(b)以及具有亲水性基团的多元醇(c)反应而得到,上述氨基甲酸酯预聚物(A)的重均分子量为2000以上且30000以下,上述聚氨酯(C)的交联度为0.03mol/kg以上且0.15mol/kg以下,上述聚氨酯(C)的脲键量为0.5mol/kg以下。
[2]在上述聚氨酯水分散体中,也可以是,上述氨基甲酸酯预聚物(A)的重均分子量为5000以上且15000以下。
[3]在上述聚氨酯水分散体中,也可以是,上述聚氨酯(C)的交联度为0.05mol/kg以上且0.10mol/kg以下。
[4]在上述聚氨酯水分散体中,也可以是,上述聚氨酯(C)的脲键量为0.1mol/kg以上且0.25mol/kg以下。
[5]在上述聚氨酯水分散体中,也可以是,上述多异氰酸酯(a)包含脂环族多异氰酸酯。
[6]在上述聚氨酯水分散体中,也可以是,上述多元醇(b)包含从由聚酯多元醇、聚碳酸酯二醇、聚醚多元醇构成的组中选出的至少一种。
[7]在上述聚氨酯水分散体中,也可以是,上述多元醇(b)的数平均分子量为400以上且3000以下。
[8]在上述聚氨酯水分散体中,也可以是,上述具有亲水性基团的多元醇(c)的亲水性基团为阴离子性亲水基。
[9]在上述聚氨酯水分散体中,也可以是,上述聚氨酯(C)的酸值为10mgKOH/g以上且45mgKOH/g以下。
[10]在上述聚氨酯水分散体中,也可以是,上述氨基甲酸酯预聚物(A)在100质量份的上述氨基甲酸酯预聚物(A)中含有15质量份以上且45质量份以下的上述多异氰酸酯(a)。
[11]在上述聚氨酯水分散体中,也可以是,上述氨基甲酸酯预聚物(A)在100质量份的上述氨基甲酸酯预聚物(A)中含有50质量份以上且80质量份以下的上述多元醇(b)。
[12]在上述聚氨酯水分散体中,也可以是,上述氨基甲酸酯预聚物(A)在100质量份的上述氨基甲酸酯预聚物(A)中含有1质量份以上且10质量份以下的上述具有亲水性基团的多元醇(c)。
[13]在上述聚氨酯水分散体中,也可以是,上述扩链剂(B)含有多胺。
[14]在上述聚氨酯水分散体中,也可以是,上述聚氨酯(C)中,相对于100质量份的上述氨基甲酸酯预聚物(A)而含有0.4质量份以上且1.0质量份以下的上述扩链剂(B)。
[15]一种涂布剂,其特征在于,含有上述[1]~[14]中的聚氨酯水分散体。
发明效果
根据本发明,能够提供一种可得到各种物性平衡优异、特别是自修复性优异的涂膜的聚氨酯水分散体以及含有该聚氨酯水分散体的涂布剂。
具体实施方式
本发明的聚氨酯水分散体是将使多异氰酸酯(a)、多元醇(b)和具有亲水性基团的多元醇(c)反应而得到的氨基甲酸酯预聚物(A)与扩链剂(B)反应而得到的聚氨酯(C)分散在水中而成。即,本发明的聚氨酯水分散体是将使氨基甲酸酯预聚物(A)与扩链剂(B)反应而得到的聚氨酯(C)分散在水中而成。该氨基甲酸酯预聚物(A)通过使多异氰酸酯(a)、多元醇(b)以及具有亲水性基团的多元醇(c)反应而得到。
上述多异氰酸酯(a)没有特别限制,可使用本技术领域中通常使用的多异氰酸酯。具体而言,可以举出:脂肪族多异氰酸酯、脂环族多异氰酸酯、芳香族多异氰酸酯、芳香脂肪族多异氰酸酯。
作为脂肪族多异氰酸酯,可以列举:四亚甲基二异氰酸酯、十二亚甲基二异氰酸酯、六亚甲基二异氰酸酯、2,2,4-三甲基六亚甲基二异氰酸酯、2,4,4-三甲基六亚甲基二异氰酸酯、赖氨酸二异氰酸酯、2-甲基戊烷-1,5-二异氰酸酯、3-甲基戊烷-1,5-二异氰酸酯等。
作为脂环族多异氰酸酯,可以列举:异佛尔酮二异氰酸酯、氢化亚二甲苯基二异氰酸酯、4,4'-二环己基甲烷二异氰酸酯、1,4-环己烷二异氰酸酯、甲基亚环己基二异氰酸酯、1,3-双(异氰酸酯甲基)环己烷等。另外,4,4'-二环己基甲烷二异氰酸酯也简称为二环己基甲烷二异氰酸酯。
作为芳香族多异氰酸酯,可以列举:甲苯二异氰酸酯(TDI)、2,2'-二苯基甲烷二异氰酸酯、2,4'-二苯基甲烷二异氰酸酯、4,4'-二苯基甲烷二异氰酸酯(MDI)、4,4'-二苄基二异氰酸酯、1,5-亚萘基二异氰酸酯、亚二甲苯基二异氰酸酯、1,3-亚苯基二异氰酸酯、1,4-亚苯基二异氰酸酯等。
作为芳香脂肪族多异氰酸酯,可以列举:二烷基二苯基甲烷二异氰酸酯、四烷基二苯基甲烷二异氰酸酯、α,α,α,α-四甲基亚二甲苯基二异氰酸酯等。
另外,可以举出这些多异氰酸酯的二聚体、三聚体或缩二脲化异氰酸酯等改性体。这些多异氰酸酯(a)可单独使用或者并用两种以上而使用。
上述多异氰酸酯中,从耐损伤性及耐溶剂性的观点出发,优选为脂环族多异氰酸酯,特别优选为4,4'-二环己基甲烷二异氰酸酯、1,4-环己烷二异氰酸酯。
本发明的氨基甲酸酯预聚物(A)中的多异氰酸酯(a)的含量没有特别限制。对于氨基甲酸酯预聚物(A),在100质量份的氨基甲酸酯预聚物(A)中,优选含有10质量份以上的多异氰酸酯(a),更优选含有15质量份以上,进一步优选含有20质量份以上,特别优选含有25质量份以上。另外,对于氨基甲酸酯预聚物(A),在100质量份的氨基甲酸酯预聚物(A)中,优选含有50质量份以下的多异氰酸酯(a),更优选含有45质量份以下,进一步优选含有50质量份以下,特别优选含有25质量份以下。例如,对于氨基甲酸酯预聚物(A),在100质量份的氨基甲酸酯预聚物(A)中,可以含有15质量份以上且45质量份以下的多异氰酸酯(a)。
作为上述多元醇(b),例如可使用(b1)聚酯多元醇、(b2)聚碳酸酯二醇、(b3)聚醚多元醇等。上述多元醇(b)可以含有从由(b1)聚酯多元醇、(b2)聚碳酸酯二醇、(b3)聚醚多元醇构成的组中选出的至少一种。
作为上述(b1)聚酯多元醇,例如可使用使低分子量的多元醇与多元羧酸进行酯化反应而得到的化合物、使ε-己内酯、γ-戊内酯等环状酯化合物进行开环聚合反应而得到的化合物、以及它们的共聚聚酯等。
作为上述低分子量的多元醇,例如可以使用:乙二醇、二乙二醇、三乙二醇、四乙二醇、1,2-丙二醇、1,3-丙二醇、二丙二醇、三丙二醇、1,2-丁二醇、1,3-丁二醇、1,4-丁二醇、2,3-丁二醇、1,5-戊二醇、1,5-己二醇、1,6-己二醇、2,5-己二醇、1,7-庚二醇、1,8-辛二醇、1,9-壬二醇、1,10-癸二醇、1,11-十一烷二醇、1,12-十二烷二醇、2-甲基-1,3-丙二醇、新戊二醇、2-丁基-2-乙基-1,3-丙二醇、3-甲基-1,5-戊二醇、2-乙基-1,3-己二醇、2-甲基-1,8-辛二醇、甘油、三羟甲基丙烷、二三羟甲基丙烷、三三羟甲基丙烷、季戊四醇等脂肪族多元醇;1,4-环己烷二甲醇、氢化双酚A等含脂肪族环式结构的多元醇;以及双酚A、双酚A的环氧烷加成物、双酚S、双酚S的环氧烷加成物等双酚型多元醇。其中,就耐损伤性及耐溶剂性方面而言,优选使用脂肪族多元醇。
作为上述多元羧酸,例如可以将琥珀酸、己二酸、辛二酸、壬二酸、癸二酸、十二烷二羧酸、二聚酸等脂肪族多元羧酸;1,4-环己烷二羧酸或环己烷三羧酸等脂环族多元羧酸;邻苯二甲酸、间苯二甲酸、对苯二甲酸、1,4-萘二羧酸、2,3-萘二羧酸、2,6-萘二羧酸、联苯二羧酸、偏苯三甲酸、均苯四甲酸等芳香族多元羧酸;以及它们的酸酐或酯衍生物单独使用或者将2种以上并用而使用,其中,就耐损伤性及耐溶剂性的方面而言,优选使用脂肪族多元羧酸。
作为上述(b2)聚碳酸酯二醇,例如可以使用使碳酸酯及/或光气与后述的多元醇反应而得到的物质。作为上述碳酸酯,例如可使用碳酸二甲酯、碳酸二乙酯、碳酸甲乙酯、碳酸亚乙酯、碳酸亚丙酯、碳酸亚丁酯、碳酸二苯酯、碳酸二萘酯、碳酸苯基萘酯等。
作为用于得到上述(b2)聚碳酸酯二醇的上述多元醇,例如可使用:乙二醇、二乙二醇、三乙二醇、四乙二醇、1,2-丙二醇、1,3-丙二醇、二丙二醇、三丙二醇、1,2-丁二醇、1,3-丁二醇、1,4-丁二醇、2,3-丁二醇、1,5-戊二醇、1,5-己二醇、1,6-己二醇、2,5-己二醇、1,7-庚二醇、1,8-辛二醇、1,9-壬二醇、1,10-癸二醇、1,11-十一烷二醇、1,12-十二烷二醇、2-甲基-1,3-丙二醇、新戊二醇、2-丁基-2-乙基-1,3-丙二醇、3-甲基-1,5-戊二醇、2-乙基-1,3-己二醇、2-甲基-1,8-辛二醇、1,4-环己烷二甲醇、对苯二酚、间苯二酚、双酚A、双酚F、4,4'-联苯酚等低分子量的二羟基化合物;聚乙二醇、聚丙二醇、聚丁二醇等聚醚多元醇;聚六亚甲基己二酸酯、聚六亚甲基琥珀酸酯、聚己内酯等聚酯多元醇等。
作为上述(b3)聚醚多元醇,例如可以使用以具有2个以上活性氢原子的化合物的一种或两种以上作为引发剂地使环氧烷加成聚合而成的物质。作为上述(b3)聚醚多元醇,例如可以使用聚乙二醇、聚丙二醇、聚丁二醇等。
作为上述引发剂,例如可以使用:水、乙二醇、二乙二醇、三乙二醇、四乙二醇、1,2-丙二醇、1,3-丙二醇、二丙二醇、三丙二醇、1,2-丁二醇、1,3-丁二醇、1,4-丁二醇、2,3-丁二醇、1,5-戊二醇、1,5-己二醇、1,6-己二醇、2,5-己二醇、1,7-庚二醇、1,8-辛二醇、1,9-壬二醇、1,10-癸二醇、1,11-十一烷二醇、1,12-十二烷二醇、2-甲基-1,3-丙二醇、新戊二醇、2-丁基-2-乙基-1,3-丙二醇、3-甲基-1,5-戊二醇、2-甲基-1,3-己二醇、2-甲基-1,8-辛二醇、甘油、二甘油、三羟甲基丙烷、二三羟甲基丙烷、三三羟甲基丙烷、1,2,6-己三醇、三乙醇胺、三异丙醇胺、季戊四醇、二季戊四醇、山梨糖醇、蔗糖、乙二胺、N-乙基二亚乙基三胺、1,2-二氨基丙烷、1,3-二氨基丙烷、1,2-二氨基丁烷、1,3-二氨基丁烷、1,4-二氨基丁烷、二亚乙基三胺、磷酸、酸性磷酸酯等。
作为上述环氧烷,例如可以列举:环氧乙烷、环氧丙烷、环氧丁烷、氧化苯乙烯、表氯醇、四氢呋喃等。
在本发明中,上述(b)多元醇中可以含有数均分子量为400以下的多元醇。
作为上述数均分子量为400以下的多元醇,是上述的低分子量的多元醇中的以下记载的多元醇。即,乙二醇、二乙二醇、三乙二醇、1,2-丙二醇、1,3-丙二醇、新戊二醇、1,3-丁二醇、1,4-丁二醇、3-甲基戊二醇、1,6-己二醇、1,8-辛二醇、2-甲基-1,3-丙二醇、双酚A、氢化双酚A、环己烷二甲醇、甘油或三羟甲基丙烷等。
这些多元醇(b)可以单独使用或将2种以上并用地使用。
本发明的氨基甲酸酯预聚物(A)中的多元醇(b)的含量没有特别限制。对于氨基甲酸酯预聚物(A),在100质量份的氨基甲酸酯预聚物(A)中,优选含有45质量份以上的多元醇(b),更优选含有50质量份以上,进一步优选含有55质量份以上,特别优选含有60质量份以上。另外,对于氨基甲酸酯预聚物(A),在100质量份的氨基甲酸酯预聚物(A)中,优选含有85质量份以下的多元醇(b),更优选含有80质量份以下,进一步优选含有75质量份以下,特别优选含有70质量份以下。例如,对于氨基甲酸酯预聚物(A),在100质量份的氨基甲酸酯预聚物(A)中,可以含有50质量份以上且80质量份以下的多元醇(b)。
本发明的氨基甲酸酯预聚物(A)中的多元醇(b)的数均分子量没有特别限制。多元醇(b)的数均分子量优选为400以上,更优选600以上,进一步优选800以上。多元醇(b)的数均分子量优选为3000以下,更优选2500以下,进一步优选2000以下。例如,多元醇(b)的数均分子量可以为400以上且3000以下。
上述具有亲水性基团的多元醇(c)的亲水性基团可以列举:阴离子性亲水基、阳离子性亲水基、非离子性亲水基,具体而言,作为阴离子性亲水基,可以列举:羧基及其盐、磺酸基及其盐;作为阳离子性亲水基,可以列举:叔铵盐、季铵盐;作为非离子性亲水基,可以列举:包含环氧乙烷重复单元的基团、包含环氧乙烷重复单元和其他环氧烷重复单元的基团等。
作为上述具有羧基的多元醇,例如可以列举:2,2-二羟甲基丙酸、2,2-二羟甲基丁酸、2,2-二羟甲基戊酸、二氧基马来酸、2,6-二氧基苯甲酸、3,4-二氨基苯甲酸等含羧酸的化合物及它们的衍生物及它们的盐,除此之外,还可以列举使用它们而得的聚酯多元醇。进一步地,还可以列举:丙氨酸、氨基丁酸、氨基己酸、甘氨酸、谷氨酸、天冬氨酸、组氨酸等氨基酸类,琥珀酸、己二酸、马来酸酐、邻苯二甲酸、偏苯三甲酸酐等羧酸类。另外,2,2-二羟甲基丙酸也简称为二羟甲基丙酸。
作为上述具有磺酸基及其盐的多元醇,例如可以列举:2-氧乙烷磺酸、苯酚磺酸、磺基苯甲酸、磺基琥珀酸、5-磺基间苯二甲酸、对氨基苯磺酸、1,3-苯二氨基-4,6-二磺酸、2,4-二氨基甲苯-5-磺酸等含磺酸的化合物及它们的衍生物以及将它们共聚得到的聚酯多元醇、聚酰胺多元醇、聚酰胺聚酯多元醇等。
这些羧基或磺酸基可以通过中和而成盐,从而使最终得到的聚氨酯成为水分散性。作为这种情况下的中和剂,例如可以列举:氢氧化钠、氢氧化钾等不挥发性碱,三甲胺、三乙胺、二甲基乙醇胺、甲基二乙醇胺、三乙醇胺等叔胺类,氨等挥发性碱等。中和可在氨基甲酸酯化反应前、反应中或反应后中的任何一个时间点进行。
作为上述具有叔铵盐的多元醇,可以举出甲基氨基乙醇、甲基二乙醇胺等烷醇胺。通过用甲酸、乙酸等有机羧酸、盐酸、硫酸等无机酸对它们进行中和而成为盐,从而可以使聚氨酯成为水分散性。中和可以在氨基甲酸酯化反应前、反应中或反应后的任意中进行。
作为上述具有季铵盐的多元醇,是利用氯甲基、溴甲基等卤化烷基、二甲基硫酸等二烷基硫酸对上述甲基氨基乙醇、甲基二乙醇胺等烷醇胺进行季铵化而得的化合物。
上述具有非离子性亲水基的多元醇没有特别限制,优选含有至少30重量%以上的环氧乙烷重复单元且数均分子量为300~20000的化合物,例如可以列举:聚氧乙二醇或聚氧乙烯-聚氧丙烯共聚物二醇、聚氧乙烯-聚氧丁烯共聚物二醇、聚氧乙烯-聚氧亚烷基共聚物二醇或其单烷基醚等含非离子性基团的化合物、或者将它们共聚而得的聚酯聚醚多元醇。
上述具有亲水性基团的多元醇(c)可分别单独使用,也可以组合使用。
上述具有亲水性基团的多元醇(c)的亲水性基团为阴离子性亲水基时,聚氨酯(C)的酸值优选为5mgKOH/g以上,更优选为10mgKOH/g以上。另一方面,优选为50mgKOH/g以下,更优选为45mgKOH/g以下。酸值在上述范围内时,在水分散性、耐水性方面优选。聚氨酯(C)的酸值(mgKOH/g)表示根据JIS K 0070:1992而测定出的值。
本发明的氨基甲酸酯预聚物(A)中的具有亲水性基团的多元醇(c)的含量没有特别限制。对于氨基甲酸酯预聚物(A),在100质量份的氨基甲酸酯预聚物(A)中,优选含有1质量份以上的具有亲水性基团的多元醇(c),更优选含有2质量份以上,进一步优选含有4质量份以上。另外,对于氨基甲酸酯预聚物(A),在100质量份的氨基甲酸酯预聚物(A)中,优选含有10质量份以下的具有亲水性基团的多元醇(c),更优选含有8质量份以下,进一步优选含有6质量份以下。例如,对于氨基甲酸酯预聚物(A),在100质量份的氨基甲酸酯预聚物(A)中,含有1质量份以上且10质量份以下的具有亲水性基团的多元醇(c)。
扩链剂(B)可使用在该技术领域中通常使用的扩链剂。没有特别限制,具体可使用二胺或多胺。作为二胺,可以示例:乙二胺、三亚甲基二胺、哌嗪、异佛尔酮二胺等,作为多胺,可以示例:二亚乙基三胺、二亚丙基三胺、三亚乙基四胺等。这些扩链剂(B)可以单独使用,也可以将两种以上并用地使用。作为扩链剂(B),优选使用多胺。另外,在本发明中,从耐损伤性的观点出发,更优选为二亚乙基三胺。
本发明的聚氨酯(C)中的扩链剂(B)的含量没有特别限制。对于聚氨酯(C),相对于100质量份的氨基甲酸酯预聚物(A),优选含有0.1质量份以上的扩链剂(B),更优选含有0.2质量份以上,进一步优选含有0.4质量份以上,特别优选含有0.6质量份以上。另外,对于聚氨酯(C),相对于100质量份的氨基甲酸酯预聚物(A),优选含有2.0质量份以下的扩链剂(B),更优选含有1.5质量份以下,进一步优选含有1.0质量份以下,特别优选含有0.7质量份以下。例如,对于聚氨酯(C),相对于100质量份的氨基甲酸酯预聚物(A),可以含有0.4质量份以上且1.0质量份以下的扩链剂(B)。
本发明的聚氨酯水分散体的制造方法没有特别限制,一般来说,以多元醇(b)及具有亲水性基团的多元醇(c)以及扩链剂(B)中含有的羟基和氨基的合计计,使化学计量上过剩的多异氰酸酯(a)的异氰酸酯基与羟基和氨基的合计量的当量比为1:0.85~1.1,在无溶剂的条件下或在不具有活性氢的有机溶剂中反应而合成氨基甲酸酯预聚物后,进行具有亲水性基团的多元醇(c)的阴离子性亲水基或阳离子性亲水基的中和,之后在水中进行分散乳化。然后,加入使氨基甲酸酯预聚物的残留异氰酸酯基与扩链剂(B)的当量比为1:0.5~0.9的扩链剂(B),使氨基甲酸酯预聚物的残留异氰酸酯基与扩链剂(B)进行表面聚合反应而生成脲键。其后,根据需要去除使用过的溶剂,从而能够得到聚氨酯水分散体。
作为上述不具有活性氢的有机溶剂,没有特别限制,具体而言,可以列举:二恶烷、甲基乙基酮、二甲基甲酰胺、四氢呋喃、N-甲基-2-吡咯烷酮、甲苯、丙二醇单甲醚乙酸酯等。优选最终将反应中使用的这些亲水性有机溶剂除去。
上述氨基甲酸酯预聚物(A)的重均分子量为2000以上且30000以下,但从耐溶剂性及耐损伤性的观点出发,优选为3000以上,更优选为5000以上。另外,优选为20000以下,更优选为15000以下。氨基甲酸酯预聚物(A)的重均分子量(Mw)可以使用凝胶渗透色谱法在以下的条件下进行测定。
装置:东曹(株)制HLC-8120
柱:2根东曹(株)制TSK GEL GMH6
测定温度:40℃
试样溶液:0.25重量%的四氢呋喃溶液
溶液注入量:100μL
检测装置:折射率检测器
基准物质:东曹(株)制标准聚苯乙烯(TSKstandard POLYSTYREN E)12点(分子量500、1050、2800、5970、9100、18100、37900、96400、190000、355000、1090000、2890000)
上述聚氨酯(C)的交联度为0.03mol/kg以上且0.15mol/kg以下,但从耐溶剂性及耐损伤性的观点出发,优选为0.04mol/g以上,更优选为0.05mol/g以上。另一方面,优选为0.12mol/g以下,更优选为0.10mol/g以下。另外,交联度也称为交联密度。
聚氨酯(C)的交联度(mol/kg)可以根据以下的方法算出。即,能够用下述的式子算出使WA1g的分子量为MWA1及官能团数为FA1的多异氰酸酯(a)、WA2g的分子量为MWA2及官能团数为FA2的多异氰酸酯(a)、WAjg(j为1以上的整数)的分子量为MWAj及官能团数为FAj的多异氰酸酯(a)、WB1g的分子量为MWB1及官能团数为FB1的多元醇(b)、WB2g的分子量为MWB2及官能团数为FB2的多元醇(b)、WBkg(k为1以上的整数)的分子量为MWBk及官能团数为FBk的多元醇(b)、WC1g的分子量为MWC1及官能团数为FC1的具有亲水性基团的多元醇(c)、WCmg(m为1以上的整数)的分子量为MWCm及官能团数为FCm的具有亲水性基团的多元醇(c)、WD1g的分子量为MWD1及官能团数为FD1的扩链剂(B)、WDng(n为1以上的整数)的分子量为MWDn及官能团数为FDn的扩链剂(B)反应而得到聚氨酯(C)的每1000分子量的交联度。
[数1]
上述聚氨酯(C)的脲键量为0.5mol/kg以下,但从耐溶剂性和耐损伤性的观点出发,优选为0.05mol/kg以上,更优选为0.1mol/kg。另一方面,优选为0.45mol/kg以下,更优选为0.25mol/kg以下。另外,本发明中的聚氨酯(C)的脲键量大于0mol/kg。
聚氨酯(C)的脲键量(mol/kg)能够利用下述的式子计算求出。另外,在下述的式子中,j、k、m均为1以上的整数。
脲键量(mol/kg)={(WA1/MWA1×FA1+WA2/MWA2×FA2+…+WAj/MWBj×FAj)-(WB1/MWB1×FB1+WB2/MWB2×FB2+…+WBk/MWBk×FBk+WC1/MWC1×FC1+WCm/MWCm×FCm)}×10
作为本发明的涂布剂,只要不妨碍本发明的效果,可使用通常使用的各种添加剂。作为此种添加剂,可以列举:例如耐候剂、抗菌剂、抗霉剂、颜料、填充材料、防锈剂、染料、成膜助剂、无机交联剂、有机交联剂(例如封端异氰酸酯系交联剂、环氧系交联剂、碳二酰亚胺系交联剂、恶唑啉类交联剂、三聚氰胺类交联剂)、硅烷偶联剂、防粘连剂、粘度调节剂、调平剂、消泡剂、分散稳定剂、光稳定剂、抗氧化剂、紫外线吸收剂、无机或有机填充剂、增塑剂、润滑剂、抗静电剂等。
[实施例]
以下,对于实施例及比较例具体地说明本发明,但本发明并不限定于此。
<聚氨酯水分散体的合成>
[实施例1]
在具备搅拌器、冷凝回流管、温度计及氮气吹入管的四口烧瓶中,加入65.00质量份的聚酯多元醇(旭化成化学股份有限公司制,商品名“PCDL T-4671”,含有作为原料的1,4-丁二醇与1,6-己二醇。重复单元:1,4-丁二醇/1,6-己二醇=7/3(摩尔比),羟值=112.2mgKOH/g,数均分子量=1000),5.00质量份的二羟甲基丙酸(DMPA),100质量份的甲基乙基酮,充分搅拌溶解,接着,加入30.00质量份的二环己基甲烷二异氰酸酯(H12MDI),在75℃下反应直至NCO含量达到0.84%。需要说明的是,“NCO含量”是指异氰酸酯基的含量。然后,将该预聚物溶液冷却至45℃,加入作为中和剂的三乙胺(TEA)3.77质量份,使用均质混合器乳化后,添加0.65质量份的二亚乙基三胺(DETA),在30℃下进行扩链反应30分钟。将该树脂溶液在加热减压下蒸馏除去甲基乙基酮,得到固体成分25%的聚氨酯水分散体。下述表1中示出氨基甲酸酯预聚物(A)的重均分子量(PP分子量)(Mw)、聚氨酯(C)的交联度(mol/kg)、聚氨酯(C)的脲键量(mol/kg)。
[实施例2]~[实施例12]、[比较例1]~[比较例4]
各原料的种类和投料量如下述表1所示变更,除此以外,与实施例1同样地进行制造,得到各聚氨酯水分散体。需要说明的是,在表1中,1,4-CHDM是指1,4-环己烷二甲醇,EG是指乙二醇,TMP是指三羟甲基丙烷,EDA是指乙二胺。另外,1,4-CHDM、EG和TMP均相当于上述数均分子量为400以下的多元醇。
[涂布层的制作]
在聚对苯二甲酸乙二酯基材(东丽(Toray)股份有限公司制PET,型号:#100T60)上,以膜厚约为20μm的方式涂布上述聚氨酯水分散体,在80℃下干燥6小时,从而制作了涂布层。
[粘性评价]
目视观察以500g负荷将上述涂布层彼此粘贴剥离时涂布面的状态。将涂布面彼此不粘接的情况记为○,将粘贴面积的50%以上粘接的情况记为△,将全部粘接的情况记为×。
[耐溶剂评价]
用涂布层中浸入有醋酸乙酯/甲苯的混合溶剂的毛毡,以500g负荷进行10次摩擦试验,目视观察涂布面的状态。将涂布面不变化的情况记为○,将被侵蚀的情况记为△,将涂布层剥离的情况记为×。
[自修复性]
用500g负荷的黄铜丝刷(藤原产业股份有限公司制No.9)对涂布面往返摩擦5次,目视观察固化膜上的损伤情况。评价是在室温23℃下进行,将10秒以内损伤复原的记为○,将花费10秒~10分钟左右的记为△,将经过1小时仍未复原的记为×。
[表1]
*1:旭化成化学股份有限公司制、商品名“PCDL T-4671”,含有作为原料的1,4-丁二醇与1,6-己二醇。重复单元:1,4-丁二醇/1,6-己二醇=7/3(摩尔比),羟值=112.2mgKOH/g,数均分子量=1000
*2:旭化成化学股份有限公司制,商品名“PCDL T-4672”,含有作为原料的1,4-丁二醇与1,6-己二醇。重复单元:1,4-丁二醇/1,6-己二醇=7/3(摩尔比),羟值=56.1mgKOH/g,数均分子量=2000
*3:宇部兴产股份有限公司制,商品名“ETERNACOLL UH-50”,含有作为原料的1,6-己二醇。羟值=224.4mgKOH/g,数均分子量=500
*4:旭化成化学股份有限公司制,商品名“PCDL T-5651”,含有作为原料的1,5-戊二醇与1,6-己二醇。重复单元:1,5-戊二醇/1,6-己二醇=1/1(摩尔比),羟值=112.2mgKOH/g,数均分子量=1000
*5:可乐丽(Kuraray)股份有限公司制,商品名“Kuraray Polyol P-1010”,含有作为原料的3-甲基-1,5-戊二醇和己二酸。羟值=112.2mgKOH/g,数均分子量=1000
*6:三菱化学股份有限公司制,商品名“PTMG1000”,聚四亚甲基二醇,数均分子量=1000
如表1所示,可知聚氨酯水分散体的脲键量大时,自修复性变差(比较例1),氨基甲酸酯预聚物的重均分子量大时,粘性及耐溶剂性变差(比较例2)。另外,在用水进行了扩链,即脲键量为0(mol/kg)的情况下,粘性、耐溶剂性、自修复性全部恶化(比较例3及4)。
产业实用性
本发明的水分散体可用作涂布剂。特别是由于自修复性良好,并且粘性及耐溶剂性良好,因此能够适用于要求这些性能的领域。
Claims (15)
1.一种聚氨酯水分散体,其特征在于,
所述聚氨酯水分散体为将使氨基甲酸酯预聚物(A)与扩链剂(B)反应而得到的聚氨酯(C)分散于水中而成,所述氨基甲酸酯预聚物(A)通过使多异氰酸酯(a)、多元醇(b)以及具有亲水性基团的多元醇(c)反应而得到,
所述氨基甲酸酯预聚物(A)的重均分子量为2000以上且30000以下,
所述聚氨酯(C)的交联度为0.03mol/kg以上且0.15mol/kg以下,
所述聚氨酯(C)的脲键量为0.5mol/kg以下。
2.根据权利要求1所述的聚氨酯水分散体,其特征在于,
所述氨基甲酸酯预聚物(A)的重均分子量为5000以上且15000以下。
3.根据权利要求1或2所述的聚氨酯水分散体,其特征在于,
所述聚氨酯(C)的交联度为0.05mol/kg以上且0.10mol/kg以下。
4.根据权利要求1至3中任一项所述的聚氨酯水分散体,其特征在于,
所述聚氨酯(C)的脲键量为0.1mol/kg以上且0.25mol/kg以下。
5.根据权利要求1至4中任一项所述的聚氨酯水分散体,其特征在于,
所述多异氰酸酯(a)包含脂环族多异氰酸酯。
6.根据权利要求1至5中任一项所述的聚氨酯水分散体,其特征在于,
所述多元醇(b)包含从由聚酯多元醇、聚碳酸酯二醇、聚醚多元醇构成的组中选出的至少一种。
7.根据权利要求1至6中任一项所述的聚氨酯水分散体,其特征在于,
所述多元醇(b)的数平均分子量为400以上且3000以下。
8.根据权利要求1至7中任一项所述的聚氨酯水分散体,其特征在于,
所述具有亲水性基团的多元醇(c)的亲水性基团为阴离子性亲水基。
9.根据权利要求8所述的聚氨酯水分散体,其特征在于,
所述聚氨酯(C)的酸值为10mgKOH/g以上且45mgKOH/g以下。
10.根据权利要求1至9中任一项所述的聚氨酯水分散体,其特征在于,
所述氨基甲酸酯预聚物(A)在100质量份的所述氨基甲酸酯预聚物(A)中含有15质量份以上且45质量份以下的所述多异氰酸酯(a)。
11.根据权利要求1至10中任一项所述的聚氨酯水分散体,其特征在于,
所述氨基甲酸酯预聚物(A)在100质量份的所述氨基甲酸酯预聚物(A)中含有50质量份以上且80质量份以下的所述多元醇(b)。
12.根据权利要求1至11中任一项所述的聚氨酯水分散体,其特征在于,
所述氨基甲酸酯预聚物(A)在100质量份的所述氨基甲酸酯预聚物(A)中含有1质量份以上且10质量份以下的所述具有亲水性基团的多元醇(c)。
13.根据权利要求1至12中任一项所述的聚氨酯水分散体,其特征在于,
所述扩链剂(B)含有多胺。
14.根据权利要求1至13中任一项所述的聚氨酯水分散体,其特征在于,
所述聚氨酯(C)中,相对于100质量份的所述氨基甲酸酯预聚物(A)而含有0.4质量份以上且1.0质量份以下的所述扩链剂(B)。
15.一种涂布剂,其特征在于,
含有权利要求1至14中任一项所述的聚氨酯水分散体。
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US20230398770A1 (en) * | 2022-06-09 | 2023-12-14 | Stek Co., Ltd. | Exterior film of building for protecting glass |
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