TWI394765B - 難燃水性聚胺基甲酸酯分散液 - Google Patents
難燃水性聚胺基甲酸酯分散液 Download PDFInfo
- Publication number
- TWI394765B TWI394765B TW097148467A TW97148467A TWI394765B TW I394765 B TWI394765 B TW I394765B TW 097148467 A TW097148467 A TW 097148467A TW 97148467 A TW97148467 A TW 97148467A TW I394765 B TWI394765 B TW I394765B
- Authority
- TW
- Taiwan
- Prior art keywords
- flame retardant
- glycol
- polyurethane dispersion
- aqueous polyurethane
- dispersion according
- Prior art date
Links
- 239000003063 flame retardant Substances 0.000 title claims description 65
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 title claims description 64
- 229920003009 polyurethane dispersion Polymers 0.000 title claims description 27
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 34
- 229920005862 polyol Polymers 0.000 claims description 23
- 150000003077 polyols Chemical class 0.000 claims description 23
- 229910052739 hydrogen Inorganic materials 0.000 claims description 18
- 239000001257 hydrogen Substances 0.000 claims description 18
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 14
- -1 diisopropyl 4,4 '- diphenylmethane ester Chemical class 0.000 claims description 13
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 12
- 125000005442 diisocyanate group Chemical group 0.000 claims description 12
- 125000000524 functional group Chemical group 0.000 claims description 11
- 229910052698 phosphorus Inorganic materials 0.000 claims description 11
- 239000011574 phosphorus Substances 0.000 claims description 11
- 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 claims description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 claims description 8
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 claims description 7
- JVYDLYGCSIHCMR-UHFFFAOYSA-N 2,2-bis(hydroxymethyl)butanoic acid Chemical compound CCC(CO)(CO)C(O)=O JVYDLYGCSIHCMR-UHFFFAOYSA-N 0.000 claims description 6
- 239000004970 Chain extender Substances 0.000 claims description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 6
- 239000002202 Polyethylene glycol Substances 0.000 claims description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 6
- 229920001223 polyethylene glycol Polymers 0.000 claims description 6
- 229920001451 polypropylene glycol Polymers 0.000 claims description 6
- 229920000909 polytetrahydrofuran Polymers 0.000 claims description 6
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 5
- VYZKQGGPNIFCLD-UHFFFAOYSA-N 3,3-dimethylhexane-2,2-diol Chemical compound CCCC(C)(C)C(C)(O)O VYZKQGGPNIFCLD-UHFFFAOYSA-N 0.000 claims description 4
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 4
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- ALQLPWJFHRMHIU-UHFFFAOYSA-N 1,4-diisocyanatobenzene Chemical compound O=C=NC1=CC=C(N=C=O)C=C1 ALQLPWJFHRMHIU-UHFFFAOYSA-N 0.000 claims description 3
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 claims description 3
- PTBDIHRZYDMNKB-UHFFFAOYSA-N 2,2-Bis(hydroxymethyl)propionic acid Chemical compound OCC(C)(CO)C(O)=O PTBDIHRZYDMNKB-UHFFFAOYSA-N 0.000 claims description 3
- 229920000388 Polyphosphate Polymers 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 239000003431 cross linking reagent Substances 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims description 3
- 239000001205 polyphosphate Substances 0.000 claims description 3
- 235000011176 polyphosphates Nutrition 0.000 claims 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 claims description 2
- XPFCZYUVICHKDS-UHFFFAOYSA-N 3-methylbutane-1,3-diol Chemical compound CC(C)(O)CCO XPFCZYUVICHKDS-UHFFFAOYSA-N 0.000 claims description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 claims description 2
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical group OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 claims description 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 claims description 2
- XMUZQOKACOLCSS-UHFFFAOYSA-N [2-(hydroxymethyl)phenyl]methanol Chemical compound OCC1=CC=CC=C1CO XMUZQOKACOLCSS-UHFFFAOYSA-N 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- 239000004305 biphenyl Substances 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 150000007942 carboxylates Chemical group 0.000 claims description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- PDXRQENMIVHKPI-UHFFFAOYSA-N cyclohexane-1,1-diol Chemical compound OC1(O)CCCCC1 PDXRQENMIVHKPI-UHFFFAOYSA-N 0.000 claims description 2
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 claims description 2
- 125000001188 haloalkyl group Chemical group 0.000 claims description 2
- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 claims description 2
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- OEIJHBUUFURJLI-UHFFFAOYSA-N octane-1,8-diol Chemical compound OCCCCCCCCO OEIJHBUUFURJLI-UHFFFAOYSA-N 0.000 claims description 2
- 229920000058 polyacrylate Polymers 0.000 claims description 2
- 229920001610 polycaprolactone Polymers 0.000 claims description 2
- 239000004632 polycaprolactone Substances 0.000 claims description 2
- 239000004417 polycarbonate Substances 0.000 claims description 2
- 229920000515 polycarbonate Polymers 0.000 claims description 2
- 229920005906 polyester polyol Polymers 0.000 claims description 2
- 229920000570 polyether Polymers 0.000 claims description 2
- HFSADXQVUOSLTK-UHFFFAOYSA-M sodium;3-[bis(2-hydroxyethyl)amino]propane-1-sulfonate Chemical compound [Na+].OCCN(CCO)CCCS([O-])(=O)=O HFSADXQVUOSLTK-UHFFFAOYSA-M 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 239000002562 thickening agent Substances 0.000 claims description 2
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 claims description 2
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 claims 1
- VZXTWGWHSMCWGA-UHFFFAOYSA-N 1,3,5-triazine-2,4-diamine Chemical group NC1=NC=NC(N)=N1 VZXTWGWHSMCWGA-UHFFFAOYSA-N 0.000 claims 1
- 229940043375 1,5-pentanediol Drugs 0.000 claims 1
- JZUHIOJYCPIVLQ-UHFFFAOYSA-N 2-methylpentane-1,5-diamine Chemical compound NCC(C)CCCN JZUHIOJYCPIVLQ-UHFFFAOYSA-N 0.000 claims 1
- 239000013543 active substance Substances 0.000 claims 1
- RRTCFFFUTAGOSG-UHFFFAOYSA-N benzene;phenol Chemical compound C1=CC=CC=C1.OC1=CC=CC=C1 RRTCFFFUTAGOSG-UHFFFAOYSA-N 0.000 claims 1
- 235000010290 biphenyl Nutrition 0.000 claims 1
- WCVRQHFDJLLWFE-UHFFFAOYSA-N pentane-1,2-diol Chemical compound CCCC(O)CO WCVRQHFDJLLWFE-UHFFFAOYSA-N 0.000 claims 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims 1
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 claims 1
- 239000004814 polyurethane Substances 0.000 description 24
- 229920002635 polyurethane Polymers 0.000 description 23
- 238000006243 chemical reaction Methods 0.000 description 16
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- 239000006185 dispersion Substances 0.000 description 9
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 230000000704 physical effect Effects 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 239000002994 raw material Substances 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- 150000002334 glycols Chemical class 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 239000012796 inorganic flame retardant Substances 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000000779 smoke Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- RJPZIYPLGIHCHR-UHFFFAOYSA-N C(O)C(C(C(=O)O)(CO)CO)CO Chemical compound C(O)C(C(C(=O)O)(CO)CO)CO RJPZIYPLGIHCHR-UHFFFAOYSA-N 0.000 description 1
- DIBLUMFNEOKXMN-UHFFFAOYSA-N C1(=CC=CC=C1)O.C1(=CC=CC=C1)O.C1(=CC=CC=C1)C Chemical compound C1(=CC=CC=C1)O.C1(=CC=CC=C1)O.C1(=CC=CC=C1)C DIBLUMFNEOKXMN-UHFFFAOYSA-N 0.000 description 1
- KSSJBGNOJJETTC-UHFFFAOYSA-N COC1=C(C=CC=C1)N(C1=CC=2C3(C4=CC(=CC=C4C=2C=C1)N(C1=CC=C(C=C1)OC)C1=C(C=CC=C1)OC)C1=CC(=CC=C1C=1C=CC(=CC=13)N(C1=CC=C(C=C1)OC)C1=C(C=CC=C1)OC)N(C1=CC=C(C=C1)OC)C1=C(C=CC=C1)OC)C1=CC=C(C=C1)OC Chemical compound COC1=C(C=CC=C1)N(C1=CC=2C3(C4=CC(=CC=C4C=2C=C1)N(C1=CC=C(C=C1)OC)C1=C(C=CC=C1)OC)C1=CC(=CC=C1C=1C=CC(=CC=13)N(C1=CC=C(C=C1)OC)C1=C(C=CC=C1)OC)N(C1=CC=C(C=C1)OC)C1=C(C=CC=C1)OC)C1=CC=C(C=C1)OC KSSJBGNOJJETTC-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- AMEDKBHURXXSQO-UHFFFAOYSA-N azonous acid Chemical class ONO AMEDKBHURXXSQO-UHFFFAOYSA-N 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 239000013065 commercial product Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000011258 core-shell material Substances 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 150000002366 halogen compounds Chemical class 0.000 description 1
- 238000007689 inspection Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 239000005416 organic matter Substances 0.000 description 1
- UWJJYHHHVWZFEP-UHFFFAOYSA-N pentane-1,1-diol Chemical compound CCCCC(O)O UWJJYHHHVWZFEP-UHFFFAOYSA-N 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 150000003018 phosphorus compounds Chemical class 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920000120 polyethyl acrylate Polymers 0.000 description 1
- 229920006264 polyurethane film Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- YGSFNCRAZOCNDJ-UHFFFAOYSA-N propan-2-one Chemical compound CC(C)=O.CC(C)=O YGSFNCRAZOCNDJ-UHFFFAOYSA-N 0.000 description 1
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000000565 sealant Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000002341 toxic gas Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/0804—Manufacture of polymers containing ionic or ionogenic groups
- C08G18/0819—Manufacture of polymers containing ionic or ionogenic groups containing anionic or anionogenic groups
- C08G18/0823—Manufacture of polymers containing ionic or ionogenic groups containing anionic or anionogenic groups containing carboxylate salt groups or groups forming them
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
- C08G18/12—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step using two or more compounds having active hydrogen in the first polymerisation step
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/4009—Two or more macromolecular compounds not provided for in one single group of groups C08G18/42 - C08G18/64
- C08G18/4081—Mixtures of compounds of group C08G18/64 with other macromolecular compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/48—Polyethers
- C08G18/4804—Two or more polyethers of different physical or chemical nature
- C08G18/4808—Mixtures of two or more polyetherdiols
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/48—Polyethers
- C08G18/4854—Polyethers containing oxyalkylene groups having four carbon atoms in the alkylene group
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/64—Macromolecular compounds not provided for by groups C08G18/42 - C08G18/63
- C08G18/6461—Macromolecular compounds not provided for by groups C08G18/42 - C08G18/63 having phosphorus
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
- C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
- C08G18/7614—Polyisocyanates or polyisothiocyanates cyclic aromatic containing only one aromatic ring
- C08G18/7621—Polyisocyanates or polyisothiocyanates cyclic aromatic containing only one aromatic ring being toluene diisocyanate including isomer mixtures
-
- 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
- C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
- C09D175/04—Polyurethanes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
- C09J175/04—Polyurethanes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Polymers & Plastics (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Manufacturing & Machinery (AREA)
- Life Sciences & Earth Sciences (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Polyurethanes Or Polyureas (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Description
本發明係有關於一種水性聚胺基甲酸酯，且特別是有關於一種難燃水性聚胺基甲酸酯分散液
聚胺基甲酸酯(PU)具有優良的物性與多變的組成，適合各種不同的用途，其可作為塗料、接著劑或密封劑等，早期使用多以溶劑型PU為主，但內含之有機物揮發會危害人體健康且造成環境污染，因此目前開發主流以水性PU為主。
然而，一般PU難燃性差，遇到火源或是在高溫的環境下會產生燃燒現象，為了解決此問題，業界將難燃劑(例如鹵系化合物、磷系化合物、無機粉體等)摻混入水性PU中，以達到阻燃效果。
日本專利JP 2002235027利用PU與無機難燃劑進行摻混，達到阻燃效果。日本專利JP 2002294018製備出核－殼(core－shell)結構之星狀高分子，核為PU結構，而殼為丙烯酸(acrylic acid)結構，再加入大量之紅磷、無機難燃劑進行摻混，以達到阻燃效果。台灣專利TW 261594利用含溴界面活性劑改質之奈米級黏土作為難燃劑，使與PU原料混合後，再聚合成水性PU，使其具有耐燃效果。
然而，大多數製備難燃水性PU時，係將難燃劑摻混入水性PU中，但其經過水洗後，通常會使難燃性降低，因此需添加高含量之難燃劑，以達到阻燃效果，但難燃劑
添加量過高時，卻會造成PU塗佈困難、加工不易的問題。
因此，業界亟需開發一種難燃水性PU，其經過水洗後仍然可維持其難燃性。
本發明提供一種難燃水性聚胺基甲酸酯分散液，包括：1~50重量份之含活性氫之磷系難燃劑；10~40重量份之二異氰酸酯；30~80重量份之多元醇；以及1~15重量份之含活性氫且可形成親水性官能基之化合物。
為讓本發明之上述和其他目的、特徵、和優點能更明顯易懂，下文特舉出較佳實施例，作詳細說明如下：
本發明提供一種難燃水性聚胺基甲酸酯分散液，其包括1~50重量份、較佳5~30重量份、更佳7~20重量份之含活性氫之磷系難燃劑、10~40重量份、較佳13~35重量份、更佳15~30重量份之二異氰酸酯(diisocynate)、30~80重量份、較佳40~75重量份、更佳50~70重量份之多元醇(polyol)佔，以及1~15重量份、較佳3~10重量份、更佳4~7重量份之含活性氫且可形成親水性官能基之化合物。上述提及之”活性氫”，意指其化合物分子結構上之氫原子具有較高的反應活性(activity)，此氫原子不穩定，容易與其他化合物進行化學反應(例如取代反應)。
本發明選擇一磷系之難燃劑，其至少含有三個磷酸酯
單元之聚磷酸酯，其化學結構式如下：
其中，R1
為烷基或烷氧基，較佳為C1~C4之烷基或烷氧基，最佳為C1~C2之烷基或烷氧基；R2
為乙烯基；n為50~270之整數，較佳為80~240之整數，最佳為100~200之整數。
此處須注意的是，一般使用鹵系難燃劑，其燃燒時會產生腐蝕性與毒性氣體，且發煙量大，容易造成人體與環境之危害，而本發明所使用之磷系難燃劑，其具有低發煙量和低毒性之優點，能符合環保需求。
由於本發明使用之難燃劑中含有活性氫，其能與二異氰酸酯進行化學反應，而產生化學鍵結於合成之聚胺基甲酸酯分子主鏈上，相較於習知技術(摻混難燃劑的方式)，本發明使用之難燃劑不會因為水洗而掉落，進而可以降低難燃劑之使用量與節省製程成本。
本發明使用之二異氫酸酯，包括脂肪族二異氰酸酯或芳香族二異氰酸酯。其中較佳例如為二異氰酸甲苯酯(Toluene diisocyanate，TDI)、對－二異氰酸苯酯(p－Phenylene diisocyanate，PPDI)、二異氫酸4,4'
－二苯基甲烷酯(4,4'
－Diphenylmethane diisocyanate，MDI)、二異氫酸p,p'
－二苯基酯(p,p'
－Bisphenyl diisocyanate，BPDI)、異佛爾酮二異氰酸酯(Isophorone diisocyanate，IPDI)、1,6－亞已基二異氰酸酯(1,6－Hexamethylene diisocynate，HDI)、二環己基
甲烷－4，4－二異氰酸酯(Hudrogenate diphenylmethane－4,4'－diisocyanate，H12
MDI)。另外，此二異氰酸酯更可包括：鹵素、硝基、氰基、烷基、烷氧基、鹵烷基、羥基、羧基、醯胺基、胺基或上述組合之取代基。
本發明之多元醇包括二醇類、多醇類、醚二醇類，其分子量範圍為60~6000，其中該二醇類例如乙二醇、丙二醇、丁二醇、戊二醇、己二醇、環己二醇、環己基二甲醇(Cyclohexyldimethanol，CHDM)、辛二醇、異戊二醇(Neopentyl glycol，NPG)、三甲基戊二醇(Trimethylpentanediol，TMPD)、苯二甲醇、苯二酚、甲苯二酚或雙酚A(Bisphenol－A)、丁二醇－己二酸共聚物[Poly(butanediol－co－adipate)glycol，PBA]、聚丁二醇(Polytetramethylene glycol，PTMEG)、己二醇－己二酸共聚物[Poly(hexanediol－co－adipate)glycol，PHA]、乙二醇－己二酸共聚物[Poly(ethanediol－co－adipate)glycol，PEA]、聚丙二醇(Polypropylene glycol，PPG)、聚乙二醇(Polyethylene glycol，PEG)。而多醇類包括聚酯多元醇、聚醚多元醇、聚碳酸酯多元醇、聚己內酯多元醇、聚丙烯酸酯多元醇，例如丙三醇、三甲基醇丙烷(Trimethylolpropane)、戊四醇(Pentaerythritol)、苯三酚。而該醚二醇類例如包括二乙二醇、三乙二醇、二丙二醇、三丙二醇。多元醇之主要作用係與二異氰酸酯反應，形成一PU聚合物，此外其另可作為一物性調節劑，依照添加之多元醇分子量的不同，會決定合成產物之硬度，一般而言，低分子量之多元醇可使產
物之硬度較低。
本發明之該含活性氫且可形成親水性官能基之化合物，其主要藉由親水性官能基使合成之聚合物能夠有效分散於水中，成為一種水性PU，其中親水性官能基包括羧酸根(－COO－
)、亞硫酸根(－SO3 －2
)、銨根(－NR4 ＋
)或聚乙二醇根(－(CH2
CH2
O)－)，而此化合物例如二羥甲基丙酸(Dimethylol propionic acid，DMPA)、二羥甲基丁酸(Dimethylol butanoic acid，DMBA)、聚環氧乙二醇(Poly(ethylene oxide)glycol)、雙(羥乙基)胺(Bis(hydroxylethyl)Amine)或3－雙(羥乙基)胺基丙烷磺酸鈉(Sodium 3－bis(hydroxyethyl)aminopropanesulfonate)。
上述提及之含活性氫之磷系難燃劑、二異氰酸酯(diisocynate)、多元醇(polyol)以及含活性氫且可形成親水性官能基之化合物，此四種成份先以預聚合物混合法(prepolymer mixing process)反應生成預聚合物，之後另外可添加一鏈延長劑，使合成之聚合物之分子量不至於太低而影響其物理性質(例如抗張強度或伸長率)。
本發明之鏈延長劑包括含有雙官能基、三官能基或四官能基之胺類，例如二乙三胺(Diethylene triamine，DETA)、三乙四胺(Triethylene tetraamine，TETA)、2－甲基－1,5－戊二胺(2－Methyl－1,5－pentamethylene diamine)或結構式為H2
N－(CH2
)m
－NH2
之化合物，其中m為0~12之整數。
再者，可依製程之需要，於本發明之難燃水性聚胺基甲酸酯中加入交聯劑、增稠劑或非磷系難燃劑，用以改善
水性PU之物性。
本發明之難燃水性聚胺基甲酸酯分散液係利用預聚合物混合法(prepolymer mixing process)製得，其合成步驟如下：(A)首先取1~50重量份之含活性氫之磷系難燃劑、30~80重量份之多元醇(polyol)，以及1~15重量份之含活性氫且可形成親水性官能基之化合物，將上述起始物溶於溶劑中，例如丙酮或N－甲基吡咯酮(N－methyl pyrrolidone；NMP)中，並於充滿氮氣之反應槽中均勻攪拌；(B)待上述反應物攪拌至均一相時，於反應槽中加入10~40重量份之二異氰酸酯(diisocynate)，於溫度40~90℃下反應4~6小時；(C)將反應槽溫度降至約30~50℃，接著添加一鹼性溶液，例如三乙胺，以進行中和反應約15~20分鐘；(D)將上述產物加入水中進行分散，接著加入0.1~5重量份之鏈延長劑，即可得到本發明之難燃水性聚胺基甲酸酯分散液。
另外，可將上述之分散液於室溫下乾燥成膜，接著再將薄膜置於80~110℃烘箱內烘乾，即可製得一難燃水性聚胺基甲酸酯乾膜。
本發明之難燃水性聚胺基甲酸酯分散液，具有下述優點：
(1)由於含活性氫之難燃劑與聚胺基甲酸酯形成化學
鍵結，因此，難燃劑經過水洗不易掉落，仍具阻燃效果且能減少難燃劑含量，進而節省製程成本。
(2)本發明合成之分散液，不需添加任何成膜助劑、可塑劑或交聯劑的狀態下，即可乾燥成膜，製程簡易，可節省製程成本與時間。
(3)本發明之難燃水性聚胺基甲酸酯乾膜可達UL 94 V0的檢驗標準，未來極有潛力成為市售商品。
實施例1
將10.36 g之二羥甲基丁酸(Dimethylol butionic acid；DMBA)、20g之磷系難燃劑，其結構式如下：
將此分散液倒入培養皿中，在室溫下放置成膜，再將薄膜於100℃烘乾半天，即可得厚度約為0.4±0.2 mm的薄膜。將所得之乾膜進行UL 94難燃規範測試，其結果如表1。
實施例2
將10.95 g之二羥甲基丁酸(Dimethylol butionic acid；DMBA)、20g之磷系難燃劑，其結構式如下：
將此分散液倒入培養皿中，在室溫下放置成膜，再將薄膜於100℃烘乾半天，即可得厚度約為0.4±0.2 mm的薄膜。將所得之乾膜進行UL 94難燃規範測試，其結果如表2。
實驗結果顯示，本發明之難燃水性PU薄膜經過浸水或洗衣粉水溶液處理後，其仍然可以維持其難燃性，皆可
達UL 94難燃規範的最高等級V0。
雖然本發明已以數個較佳實施例揭露如上，然其並非用以限定本發明，任何所屬技術領域中具有通常知識者，在不脫離本發明之精神和範圍內，當可作任意之更動與潤飾，因此本發明之保護範圍當視後附之申請專利範圍所界定者為準。
Claims (19)
- 一種難燃水性聚胺基甲酸酯分散液，包括：1~50重量份之含活性氫之磷系難燃劑，其中該含活性氫之磷系難燃劑為至少含有三個磷酸酯單元之聚磷酸酯；10~40重量份之二異氰酸酯；30~80重量份之多元醇，其中該多元醇包括二醇類、多醇類或醚二醇類；以及1~15重量份之含活性氫且可形成親水性官能基之化合物，其中該含活性氫且可形成親水性官能基之化合物之親水性官能基包括羧酸根(-COO- )、亞硫酸根(-SO3 -2 )、銨根(-NR4 + )或聚乙二醇根(-(CH2 CH2 O)-)。
- 如申請專利範圍第1項所述之難燃水性聚胺基甲酸酯分散液，其中更包括0.1~5重量份之鏈延長劑。
- 如申請專利範圍第1項所述之難燃水性聚胺基甲酸酯分散液，其中該聚磷酸酯之結構式如下：
- 如申請專利範圍第3項所述之難燃水性聚胺基甲酸酯分散液，其中R1 為C1~C4之烷基或烷氧基。
- 如申請專利範圍第3項所述之難燃水性聚胺基甲 酸酯分散液，其中R1 為C1~C2之烷基或烷氧基。
- 如申請專利範圍第3項所述之難燃水性聚胺基甲酸酯分散液，其中n為80~240之整數。
- 如申請專利範圍第3項所述之難燃水性聚胺基甲酸酯分散液，其中n為100~200之整數。
- 如申請專利範圍第1項所述之難燃水性聚胺基甲酸酯分散液，其中該二異氰酸酯包括芳香族二異氰酸酯或脂肪族二異氰酸酯。
- 如申請專利範圍第8項所述之難燃水性聚胺基甲酸酯分散液，其中該二異氰酸酯包括二異氰酸甲苯酯(Toluene diisocyanate，TDI)、對-二異氰酸苯酯(p-Phenylene diisocyanate，PPDI)、二異氫酸4,4' -二苯基甲烷酯(4,4' -Diphenylmethane diisocyanate，MDI)或二異氫酸p,p' -二苯基酯(p,p' -Bisphenyl diisocyanate，BPDI)、異佛爾酮二異氰酸酯(Isophorone diisocyanate，IPDI)、1,6-亞已基二異氰酸酯(1,6-Hexamethylene diisocynate，HDI)或二環己基甲烷-4，4-二異氰酸酯(Hudrogenate diphenylmethane-4,4'-diisocyanate，H12 MDI)。
- 如申請專利範圍第1項所述之難燃水性聚胺基甲酸酯分散液，其中該二異氰酸酯更包括：鹵素、硝基、氰基、烷基、烷氧基、鹵烷基、羥基、羧基、醯胺基、胺基或上述組合之取代基。
- 如申請專利範圍第1項所述之難燃水性聚胺基甲酸酯分散液，其中該二醇類包括乙二醇、丙二醇、丁二醇、 戊二醇、己二醇、環己二醇、環己基二甲醇(Cyclohexyldimethanol，CHDM)、辛二醇、異戊二醇(Neopentyl glycol，NPG)、三甲基戊二醇(Trimethylpentanediol，TMPD)、苯二甲醇、苯二酚、甲苯二酚或雙酚A(Bisphenol-A)、丁二醇-己二酸共聚物[Poly(butanediol-co-adipate)glycol，PBA]、聚丁二醇(Polytetramethylene glycol，PTMEG)、己二醇-己二酸共聚物[Poly(hexanediol-co-adipate)glycol，PHA]、乙二醇-己二酸共聚物[Poly(ethanediol-co-adipate)glycol，PEA]、聚丙二醇(Polypropylene glycol，PPG)或聚乙二醇(Polyethylene glycol，PEG)。
- 如申請專利範圍第1項所述之難燃水性聚胺基甲酸酯分散液，其中該多醇類包括聚酯多元醇、聚醚多元醇、聚碳酸酯多元醇、聚己內酯多元醇或聚丙烯酸酯多元醇。
- 如申請專利範圍第12項所述之難燃水性聚胺基甲酸酯分散液，其中該多醇類包括丙三醇、三甲基醇丙烷(trimethylolpropane)、戊四醇(Pentaerythritol)或苯三酚。
- 如申請專利範圍第1項所述之難燃水性聚胺基甲酸酯分散液，其中該醚二醇類包括二乙二醇、三乙二醇、二丙二醇或三丙二醇。
- 如申請專利範圍第1項所述之難燃水性聚胺基甲酸酯分散液，其中該多元醇之分子量範圍為60~6000。
- 如申請專利範圍第1項所述之難燃水性聚胺基甲酸酯分散液，其中該含活性氫且可形成親水性官能基之化 合物包括二羥甲基丙酸(Dimethylol propionic acid，DMPA)、二羥甲基丁酸(Dimethylol butanoic acid，DMBA)、聚環氧乙二醇(Poly(ethylene oxide)glycol)、雙(羥乙基)胺(Bis(hydroxylethyl)Amine)或3-雙(羥乙基)胺基丙烷磺酸鈉(Sodium 3-bis(hydroxyethyl)aminopropanesulfonate)。
- 如申請專利範圍第1項所述之難燃水性聚胺基甲酸酯分散液，其中該鏈延長劑包括含有雙官能基、三官能基或四官能基之胺類。
- 如申請專利範圍第1項所述之難燃水性聚胺基甲酸酯分散液，其中該鏈延長劑包括乙二胺、二乙三胺(Diethylene triamine，DETA)、三乙四胺(Triethylene tetraamine，TETA)、2-甲基-1,5-戊二胺(2-Methyl-1,5-pentamethylenediamine)或結構式為H2 N-(CH2 )m -NH2 之化合物，其中m為0~12之整數。
- 如申請專利範圍第1項所述之難燃水性聚胺基甲酸酯分散液，其中該難燃水性聚胺基甲酸酯分散液更包括交聯劑、增稠劑或非磷系難燃劑。
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| TW097148467A TWI394765B (zh) | 2008-12-12 | 2008-12-12 | 難燃水性聚胺基甲酸酯分散液 |
| US12/471,601 US20100152374A1 (en) | 2008-12-12 | 2009-05-26 | Flame-retardant waterborne polyurethane dispersion |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| TW097148467A TWI394765B (zh) | 2008-12-12 | 2008-12-12 | 難燃水性聚胺基甲酸酯分散液 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| TW201022310A TW201022310A (en) | 2010-06-16 |
| TWI394765B true TWI394765B (zh) | 2013-05-01 |
Family
ID=42241296
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW097148467A TWI394765B (zh) | 2008-12-12 | 2008-12-12 | 難燃水性聚胺基甲酸酯分散液 |
Country Status (2)
| Country | Link |
|---|---|
| US (1) | US20100152374A1 (zh) |
| TW (1) | TWI394765B (zh) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI477492B (zh) * | 2008-01-17 | 2015-03-21 | Aventis Pharma Sa | 二甲氧基多烯紫杉醇之結晶型及其製備方法 |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101885830B (zh) * | 2010-06-24 | 2012-01-25 | 同济大学 | 水性聚氨酯乳液的合成方法 |
| JP5612983B2 (ja) * | 2010-09-28 | 2014-10-22 | 株式会社Adeka | 難燃性塗工材用水系ポリウレタン樹脂組成物、及び該組成物を塗布してなる塗工品 |
| CN102212181B (zh) * | 2011-05-10 | 2012-07-04 | 丹东恒悦新材料有限公司 | 水性阻燃聚氨酯树脂及制备方法 |
| US10195342B2 (en) | 2014-04-24 | 2019-02-05 | Becton, Dickinson And Company | Cannula deployment mechanism |
| KR101756184B1 (ko) * | 2015-04-03 | 2017-07-11 | 주식회사 지엠이노텍 | 비용출부 도입 난연제 제조방법, 이에 의하여 제조된 비용출부 도입 난연제, 및 이를 포함하는 난연 수지 조성물 |
| EP3356439A1 (en) | 2015-10-01 | 2018-08-08 | DSM IP Assets B.V. | Halogen free flame retardant waterborne coating composition for textile |
| EP3239213A1 (en) | 2016-04-25 | 2017-11-01 | Henkel AG & Co. KGaA | Aqueous flame-retardant polyurethane polymeric dispersions |
| CN106589297A (zh) * | 2016-11-01 | 2017-04-26 | 北京理工大学 | 一种高效本质阻燃水性聚氨酯 |
| CN107099015B (zh) * | 2017-03-24 | 2020-02-21 | 广东科茂林产化工股份有限公司 | 一种改性水性聚氨酯分散体及其制备方法 |
| CN107417873B (zh) * | 2017-04-07 | 2020-07-31 | 中国科学院长春应用化学研究所 | 一种水性聚氨酯分散体及其无溶剂制备方法 |
| CN107082863B (zh) * | 2017-05-22 | 2020-01-07 | 昆山嘉力普制版胶粘剂油墨有限公司 | 一种高强度腰果酚基水性聚氨酯的制备方法 |
| CN107417871A (zh) * | 2017-07-14 | 2017-12-01 | 合肥思敬齐化工材料有限责任公司 | 水性聚氨酯玻璃保护胶及其制备方法 |
| CN107759763B (zh) * | 2017-11-01 | 2020-08-04 | 北京中纺化工股份有限公司 | 一种用于纺织品耐洗涤阻燃增效剂及其制备方法与应用 |
| CN109096482B (zh) * | 2018-06-08 | 2022-02-25 | 海尔智家股份有限公司 | 阻燃多元醇组合物及其制备方法、应用 |
| CN108977158A (zh) * | 2018-07-19 | 2018-12-11 | 德华兔宝宝装饰新材股份有限公司 | 一种木质防火门用阻燃胶粘剂及其制备方法 |
| CN109096532A (zh) * | 2018-08-20 | 2018-12-28 | 德清顾舒家华高分子材料有限公司 | 一种提高聚氨酯泡沫阻燃性能的方法 |
| DE102018215651A1 (de) | 2018-09-14 | 2020-03-19 | Tesa Se | Elastischer flammgeschützter Polyurethanschaum, Klebeband mit einem Träger daraus sowie Herstellungsverfahren dafür |
| CN113122121A (zh) * | 2021-04-23 | 2021-07-16 | 中科院广州化学有限公司 | 具有半互穿网络结构的含磷聚氨酯-丙烯酸树脂阻燃涂料及其制法和应用 |
| CN116836620B (zh) * | 2023-08-10 | 2024-03-29 | 上海岩皇环保科技有限公司 | 一种高弹性高阻燃的改性聚氨酯涂料及其制备方法 |
| CN120888231B (zh) * | 2025-10-10 | 2025-12-02 | 南通宝利来涂料有限公司 | 一种水性聚氨酯防火涂料及其制备方法 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5688860A (en) * | 1992-06-26 | 1997-11-18 | Minnesota Mining And Manufacturing Company | Polyurethane/polyurea elastomers |
| US20080191179A1 (en) * | 2005-04-01 | 2008-08-14 | Saint-Gobain Isover | Mineral Wool, Insulating Product And Production Method |
-
2008
- 2008-12-12 TW TW097148467A patent/TWI394765B/zh active
-
2009
- 2009-05-26 US US12/471,601 patent/US20100152374A1/en not_active Abandoned
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5688860A (en) * | 1992-06-26 | 1997-11-18 | Minnesota Mining And Manufacturing Company | Polyurethane/polyurea elastomers |
| US20080191179A1 (en) * | 2005-04-01 | 2008-08-14 | Saint-Gobain Isover | Mineral Wool, Insulating Product And Production Method |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI477492B (zh) * | 2008-01-17 | 2015-03-21 | Aventis Pharma Sa | 二甲氧基多烯紫杉醇之結晶型及其製備方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| TW201022310A (en) | 2010-06-16 |
| US20100152374A1 (en) | 2010-06-17 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| TWI394765B (zh) | 難燃水性聚胺基甲酸酯分散液 | |
| CN101883803B (zh) | 水性聚氨酯树脂、亲水性树脂及膜 | |
| JP4497246B2 (ja) | アルコール可溶型ウレタン樹脂組成物の製造方法、ポリウレタン多孔体及び透湿性フィルム | |
| CN104592475A (zh) | 含有磷杂菲和/或苯基磷酸酯基的阻燃水性聚氨酯的制法 | |
| US20130197159A1 (en) | Polyurethane elastomer coatings | |
| ES2983289T3 (es) | Procedimiento para preparación de dispersiones acuosas de poliuretano que son sustancialmente libres de compuestos orgánicos volátiles y que tienen un alto contenido de sólidos | |
| CN108440735A (zh) | 含Diels-Alder键自修复阻燃聚氨酯弹性体及其制备方法 | |
| CN101597369A (zh) | 含脂环族磺酸型亲水性扩链剂的高固含量聚氨酯乳液及其制备方法 | |
| TW200418895A (en) | Polyurethane dispersion and articles prepared therefrom | |
| CN101381445A (zh) | 一种环保无卤反应型阻燃水性聚氨酯及其制备方法 | |
| JP2018104605A (ja) | カルボキシル基含有水性樹脂組成物、成形体、及びポリカルボジイミド化合物の製造方法 | |
| TWI813549B (zh) | 聚碳二亞胺共聚物 | |
| Xing et al. | Construction of a flame retardant polyurethane elastomer with degradability, high mechanical strength and shape memory | |
| CN107686547B (zh) | 阻燃聚氨酯及其制备方法 | |
| KR101649759B1 (ko) | 에폭시기를 함유한 수분산 폴리우레탄의 제조방법 | |
| JP5227561B2 (ja) | ウレア樹脂組成物 | |
| US9284458B2 (en) | Silicone backbone prepolymers for flame resistant polyurethanes | |
| JP2011157527A (ja) | カルボニル基含有ウレタンウレア樹脂の水分散体 | |
| CN116804075A (zh) | 一种可生物降解的高强度聚氨酯材料及其制备方法 | |
| CN101759842B (zh) | 阻燃水性聚氨基甲酸酯分散液 | |
| TWI819291B (zh) | 水性聚氨酯 | |
| JP5710856B2 (ja) | ウレアウレタン樹脂組成物 | |
| KR100911174B1 (ko) | 표면처리용 난연성 폴리우레탄 수지 조성물 및 그의제조방법 | |
| JP2010229224A (ja) | 水性ポリウレタン分散体及びそれを用いた水性塗料 | |
| TW202502867A (zh) | 聚胺基甲酸酯樹脂組成物、及使用其而成的透濕防水布帛、運動服、雨衣、帳篷、及衛生用品 |