EP3538583A1 - Isocyanuratpolymere mit dualer härtung - Google Patents
Isocyanuratpolymere mit dualer härtungInfo
- Publication number
- EP3538583A1 EP3538583A1 EP17794993.0A EP17794993A EP3538583A1 EP 3538583 A1 EP3538583 A1 EP 3538583A1 EP 17794993 A EP17794993 A EP 17794993A EP 3538583 A1 EP3538583 A1 EP 3538583A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- isocyanate
- component
- polymerizable composition
- groups
- acrylate
- 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
Links
- 229920000642 polymer Polymers 0.000 title claims abstract description 28
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 title description 18
- 239000000203 mixture Substances 0.000 claims abstract description 90
- 238000000034 method Methods 0.000 claims abstract description 70
- 239000012948 isocyanate Substances 0.000 claims description 103
- 150000002513 isocyanates Chemical class 0.000 claims description 102
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 79
- 239000003054 catalyst Substances 0.000 claims description 35
- 238000004132 cross linking Methods 0.000 claims description 33
- 239000003999 initiator Substances 0.000 claims description 24
- 230000008569 process Effects 0.000 claims description 20
- 238000002360 preparation method Methods 0.000 claims description 17
- 238000005829 trimerization reaction Methods 0.000 claims description 15
- 230000005855 radiation Effects 0.000 claims description 14
- 238000010526 radical polymerization reaction Methods 0.000 claims description 11
- 239000007795 chemical reaction product Substances 0.000 claims description 7
- 239000011248 coating agent Substances 0.000 claims description 5
- 238000000576 coating method Methods 0.000 claims description 5
- 238000007259 addition reaction Methods 0.000 claims description 2
- 230000007246 mechanism Effects 0.000 abstract description 7
- 238000007348 radical reaction Methods 0.000 abstract description 4
- 239000005056 polyisocyanate Substances 0.000 description 69
- 229920001228 polyisocyanate Polymers 0.000 description 69
- NIXOWILDQLNWCW-UHFFFAOYSA-M acrylate group Chemical group C(C=C)(=O)[O-] NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 53
- 125000005442 diisocyanate group Chemical group 0.000 description 28
- -1 aromatic radicals Chemical class 0.000 description 24
- 239000011541 reaction mixture Substances 0.000 description 21
- AVWRKZWQTYIKIY-UHFFFAOYSA-N urea-1-carboxylic acid Chemical compound NC(=O)NC(O)=O AVWRKZWQTYIKIY-UHFFFAOYSA-N 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 14
- PCHXZXKMYCGVFA-UHFFFAOYSA-N 1,3-diazetidine-2,4-dione Chemical compound O=C1NC(=O)N1 PCHXZXKMYCGVFA-UHFFFAOYSA-N 0.000 description 13
- OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical compound NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 description 13
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 13
- 150000001875 compounds Chemical class 0.000 description 12
- PJMDLNIAGSYXLA-UHFFFAOYSA-N 6-iminooxadiazine-4,5-dione Chemical compound N=C1ON=NC(=O)C1=O PJMDLNIAGSYXLA-UHFFFAOYSA-N 0.000 description 11
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 10
- 229910052757 nitrogen Inorganic materials 0.000 description 10
- 239000004814 polyurethane Substances 0.000 description 10
- 229920002635 polyurethane Polymers 0.000 description 10
- 229910052708 sodium Inorganic materials 0.000 description 10
- 125000001931 aliphatic group Chemical group 0.000 description 9
- HXSACZWWBYWLIS-UHFFFAOYSA-N oxadiazine-4,5,6-trione Chemical group O=C1ON=NC(=O)C1=O HXSACZWWBYWLIS-UHFFFAOYSA-N 0.000 description 9
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 8
- 239000011734 sodium Substances 0.000 description 8
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 7
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 7
- 239000000654 additive Substances 0.000 description 7
- 238000001723 curing Methods 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- 238000006116 polymerization reaction Methods 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 229910052726 zirconium Inorganic materials 0.000 description 7
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 6
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000003513 alkali Substances 0.000 description 6
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 239000000178 monomer Substances 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 229920001223 polyethylene glycol Polymers 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- 239000011521 glass Substances 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- 229920000570 polyether Polymers 0.000 description 5
- 229910052700 potassium Inorganic materials 0.000 description 5
- 239000011591 potassium Substances 0.000 description 5
- 150000003512 tertiary amines Chemical class 0.000 description 5
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 4
- VVBLNCFGVYUYGU-UHFFFAOYSA-N 4,4'-Bis(dimethylamino)benzophenone Chemical compound C1=CC(N(C)C)=CC=C1C(=O)C1=CC=C(N(C)C)C=C1 VVBLNCFGVYUYGU-UHFFFAOYSA-N 0.000 description 4
- 239000002202 Polyethylene glycol Substances 0.000 description 4
- 239000004721 Polyphenylene oxide Substances 0.000 description 4
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 4
- 229910000287 alkaline earth metal oxide Inorganic materials 0.000 description 4
- 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 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 150000007942 carboxylates Chemical class 0.000 description 4
- 239000003085 diluting agent Substances 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 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 4
- 229910052751 metal Chemical class 0.000 description 4
- 239000002184 metal Chemical class 0.000 description 4
- 150000004707 phenolate Chemical class 0.000 description 4
- 229920000582 polyisocyanurate Polymers 0.000 description 4
- 235000011056 potassium acetate Nutrition 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 125000001453 quaternary ammonium group Chemical group 0.000 description 4
- DFPJRUKWEPYFJT-UHFFFAOYSA-N 1,5-diisocyanatopentane Chemical compound O=C=NCCCCCN=C=O DFPJRUKWEPYFJT-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 229910052684 Cerium Inorganic materials 0.000 description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- 229920002565 Polyethylene Glycol 400 Polymers 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical class CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 3
- 230000000996 additive effect Effects 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 150000001340 alkali metals Chemical class 0.000 description 3
- 150000001342 alkaline earth metals Chemical class 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 229910052788 barium Inorganic materials 0.000 description 3
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 3
- 239000012965 benzophenone Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 229910052791 calcium Inorganic materials 0.000 description 3
- 239000011575 calcium Substances 0.000 description 3
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 3
- ZMIGMASIKSOYAM-UHFFFAOYSA-N cerium Chemical compound [Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce] ZMIGMASIKSOYAM-UHFFFAOYSA-N 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 229910017052 cobalt Inorganic materials 0.000 description 3
- 239000010941 cobalt Substances 0.000 description 3
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 229910052802 copper Inorganic materials 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- 150000003983 crown ethers Chemical class 0.000 description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 238000000113 differential scanning calorimetry Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 239000003063 flame retardant Substances 0.000 description 3
- 230000009477 glass transition Effects 0.000 description 3
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 3
- 150000004679 hydroxides Chemical class 0.000 description 3
- 229910052742 iron Inorganic materials 0.000 description 3
- 229910052744 lithium Inorganic materials 0.000 description 3
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 3
- 229910052759 nickel Inorganic materials 0.000 description 3
- 229920003023 plastic Polymers 0.000 description 3
- 239000004033 plastic Substances 0.000 description 3
- 239000011495 polyisocyanurate Substances 0.000 description 3
- 229920005862 polyol Polymers 0.000 description 3
- 150000003077 polyols Chemical class 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 229910052718 tin Inorganic materials 0.000 description 3
- 229910052725 zinc Inorganic materials 0.000 description 3
- 239000011701 zinc Substances 0.000 description 3
- KCZQSKKNAGZQSZ-UHFFFAOYSA-N 1,3,5-tris(6-isocyanatohexyl)-1,3,5-triazin-2,4,6-trione Chemical compound O=C=NCCCCCCN1C(=O)N(CCCCCCN=C=O)C(=O)N(CCCCCCN=C=O)C1=O KCZQSKKNAGZQSZ-UHFFFAOYSA-N 0.000 description 2
- OVBFMUAFNIIQAL-UHFFFAOYSA-N 1,4-diisocyanatobutane Chemical compound O=C=NCCCCN=C=O OVBFMUAFNIIQAL-UHFFFAOYSA-N 0.000 description 2
- RXYPXQSKLGGKOL-UHFFFAOYSA-N 1,4-dimethylpiperazine Chemical compound CN1CCN(C)CC1 RXYPXQSKLGGKOL-UHFFFAOYSA-N 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 2
- GNSFRPWPOGYVLO-UHFFFAOYSA-N 3-hydroxypropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCO GNSFRPWPOGYVLO-UHFFFAOYSA-N 0.000 description 2
- 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 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- NDWUBGAGUCISDV-UHFFFAOYSA-N 4-hydroxybutyl prop-2-enoate Chemical compound OCCCCOC(=O)C=C NDWUBGAGUCISDV-UHFFFAOYSA-N 0.000 description 2
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 239000005058 Isophorone diisocyanate Substances 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- DLRVVLDZNNYCBX-UHFFFAOYSA-N Polydextrose Polymers OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(O)C(O)O1 DLRVVLDZNNYCBX-UHFFFAOYSA-N 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- 229920002396 Polyurea Polymers 0.000 description 2
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
- IAXXETNIOYFMLW-COPLHBTASA-N [(1s,3s,4s)-4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl] 2-methylprop-2-enoate Chemical compound C1C[C@]2(C)[C@@H](OC(=O)C(=C)C)C[C@H]1C2(C)C IAXXETNIOYFMLW-COPLHBTASA-N 0.000 description 2
- 150000001242 acetic acid derivatives Chemical class 0.000 description 2
- 230000003213 activating effect Effects 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 2
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 2
- 150000008366 benzophenones Chemical class 0.000 description 2
- 235000019400 benzoyl peroxide Nutrition 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- PBAYDYUZOSNJGU-UHFFFAOYSA-N chelidonic acid Natural products OC(=O)C1=CC(=O)C=C(C(O)=O)O1 PBAYDYUZOSNJGU-UHFFFAOYSA-N 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 2
- KORSJDCBLAPZEQ-UHFFFAOYSA-N dicyclohexylmethane-4,4'-diisocyanate Chemical compound C1CC(N=C=O)CCC1CC1CCC(N=C=O)CC1 KORSJDCBLAPZEQ-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 230000009977 dual effect Effects 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 229910052735 hafnium Inorganic materials 0.000 description 2
- VBJZVLUMGGDVMO-UHFFFAOYSA-N hafnium atom Chemical compound [Hf] VBJZVLUMGGDVMO-UHFFFAOYSA-N 0.000 description 2
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 230000000977 initiatory effect Effects 0.000 description 2
- 239000011256 inorganic filler Substances 0.000 description 2
- 229910003475 inorganic filler Inorganic materials 0.000 description 2
- 229940119545 isobornyl methacrylate Drugs 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 2
- 239000001095 magnesium carbonate Substances 0.000 description 2
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 2
- 235000014380 magnesium carbonate Nutrition 0.000 description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
- 229910052753 mercury Inorganic materials 0.000 description 2
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 2
- 229910021645 metal ion Inorganic materials 0.000 description 2
- 238000006011 modification reaction Methods 0.000 description 2
- 238000000465 moulding Methods 0.000 description 2
- 125000005609 naphthenate group Chemical group 0.000 description 2
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 2
- FBUKVWPVBMHYJY-UHFFFAOYSA-N nonanoic acid Chemical compound CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 description 2
- 125000005474 octanoate group Chemical group 0.000 description 2
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 2
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- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 1
- BJQWBACJIAKDTJ-UHFFFAOYSA-N tetrabutylphosphanium Chemical compound CCCC[P+](CCCC)(CCCC)CCCC BJQWBACJIAKDTJ-UHFFFAOYSA-N 0.000 description 1
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- VBHJAIGGLJOOLJ-UHFFFAOYSA-M tetramethylphosphanium;fluoride Chemical compound [F-].C[P+](C)(C)C VBHJAIGGLJOOLJ-UHFFFAOYSA-M 0.000 description 1
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- 150000003606 tin compounds Chemical class 0.000 description 1
- KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical compound [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 0.000 description 1
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- GNABDJMISKSNIQ-UHFFFAOYSA-N tributyl(imidazol-1-yl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)N1C=CN=C1 GNABDJMISKSNIQ-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
- B29C64/00—Additive manufacturing, i.e. manufacturing of three-dimensional [3D] objects by additive deposition, additive agglomeration or additive layering, e.g. by 3D printing, stereolithography or selective laser sintering
- B29C64/10—Processes of additive manufacturing
- B29C64/106—Processes of additive manufacturing using only liquids or viscous materials, e.g. depositing a continuous bead of viscous material
- B29C64/112—Processes of additive manufacturing using only liquids or viscous materials, e.g. depositing a continuous bead of viscous material using individual droplets, e.g. from jetting heads
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
- B29C64/00—Additive manufacturing, i.e. manufacturing of three-dimensional [3D] objects by additive deposition, additive agglomeration or additive layering, e.g. by 3D printing, stereolithography or selective laser sintering
- B29C64/10—Processes of additive manufacturing
- B29C64/106—Processes of additive manufacturing using only liquids or viscous materials, e.g. depositing a continuous bead of viscous material
- B29C64/124—Processes of additive manufacturing using only liquids or viscous materials, e.g. depositing a continuous bead of viscous material using layers of liquid which are selectively solidified
-
- 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
- C08G18/81—Unsaturated isocyanates or isothiocyanates
- C08G18/8125—Unsaturated isocyanates or isothiocyanates having two or more isocyanate or isothiocyanate groups
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
- B29C39/00—Shaping by casting, i.e. introducing the moulding material into a mould or between confining surfaces without significant moulding pressure; Apparatus therefor
- B29C39/003—Shaping by casting, i.e. introducing the moulding material into a mould or between confining surfaces without significant moulding pressure; Apparatus therefor characterised by the choice of material
- B29C39/006—Monomers or prepolymers
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
- B29C64/00—Additive manufacturing, i.e. manufacturing of three-dimensional [3D] objects by additive deposition, additive agglomeration or additive layering, e.g. by 3D printing, stereolithography or selective laser sintering
- B29C64/10—Processes of additive manufacturing
- B29C64/106—Processes of additive manufacturing using only liquids or viscous materials, e.g. depositing a continuous bead of viscous material
- B29C64/124—Processes of additive manufacturing using only liquids or viscous materials, e.g. depositing a continuous bead of viscous material using layers of liquid which are selectively solidified
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Definitions
- the present invention relates to polymerizable compositions containing components that can be crosslinked by isocyanurate bonds as well as by a free-radical reaction mechanism. It further relates to methods by which polymers can be made from these compositions.
- WO 2015/155195 describes a composite material obtainable from a reinforcing material and a polyurethane composition consisting of at least one polyisocyanate (PIC), a PIC-reactive component consisting of at least one polyol and at least one methacrylate having OH groups, and a radical initiator.
- PIC polyisocyanate
- PIC-reactive component consisting of at least one polyol and at least one methacrylate having OH groups
- a radical initiator a radical initiator
- WO 2016/087366 describes a free-radically polymerizable composition consisting of a polyurethane which contains double bonds and a reactive diluent based on various methacrylates.
- the disadvantage here is the two-stage reaction procedure, since first a polyurethane starting from an isocyanate-containing component and a polyol prepared, and must be greatly diluted. Subsequent crosslinking takes place exclusively via a free radical polymerization in a separate step.
- WO 2016/170057, WO 2016/170059 and WO 2016/170061 describe the preparation of polyisocyanurate plastics by polyaddition of oligomeric isocyanates.
- the use of oligomeric isocyanates instead of monomeric isocyanates results in less heat of reaction being produced during the polymerization and thus rapid polymerization is possible without the reaction mixture overheating. This is particularly important in the production of moldings, since here the heat generated in the interior of the molded body can be dissipated only limited over the surface.
- the monomer-poor polyisocyanate compositions described in these applications as starting materials have the disadvantage of a high, relatively high viscosity, which may be a hindrance in some applications.
- the addition of monomeric polyisocyanates as reactive diluents is undesirable because of the above-described problem of heat of reaction.
- monomeric polyisocyanates are highly volatile and therefore should not be used for reasons of occupational safety.
- conventional organic solvents can be used to reduce the viscosity.
- these are disadvantageous for reasons of environmental protection, since they are released during or after the polymerization in the ambient air.
- the use of solvents in the production of moldings can lead to material defects, for example to the formation of voids, since the volume of the evaporating solvent is missing in the material.
- the present invention was initially based on the object of providing a reaction system with a dual curing mechanism in which the mixing ratio of the reactants can be set in a significantly wider range than in the known radiation-crosslinkable polyurethane systems.
- the present invention relates to a polymerizable composition having a ratio of isocyanate groups to isocyanate-reactive groups of at least 2.0 to 1.0 comprising a) an isocyanate component A;
- component B has at least one ethylenic double bond but no isocyanate-reactive group
- component D in a molecule has at least one isocyanate-reactive group and at least one ethylenic double bond
- the component E in a molecule has both at least one isocyanate group and at least one ethylenic double bond.
- the isocyanate component A allows the formation of a polymer formed by the addition of isocyanate groups. In particular, isocyanurate groups are formed.
- the crosslinking of the isocyanate groups contained in the isocyanate component A gives the polymer the majority of its mechanical and chemical stability.
- the crosslinking of the isocyanate groups is mediated by the trimerization catalyst C.
- Components B, D and E are each characterized by the presence of an ethylenic double bond. This double bond is prerequisite for the fact that a second crosslinking mechanism is available in addition to the polyaddition of the isocyanate groups in the polymerizable composition.
- a second crosslinking mechanism is available in addition to the polyaddition of the isocyanate groups in the polymerizable composition.
- Component B decreases the viscosity of the polymerizable composition. It can thus advantageously serve as a reactive diluent, i. it becomes part of the polymer after completion of the polymerization process. It can also serve the rapid buildup of viscosity when initially, preferably by actinic radiation, or initiation by means of a thermally activatable initiator, a radical polymerization of the ethylenic double bonds is initiated and only after the crosslinking of the isocyanate groups is performed.
- the component B is used in combination with a component D or E. It can also be used in combination with both components.
- the components D and E mediate the crosslinking of the resulting by free radical polymerization network of component B with the polyaddition of the isocyanate groups resulting polymer of the isocyanate A. They ensure that the polymer is not two separate polymer networks of components A and B, but a uniform polymer network.
- the components D and F can also be used without the addition of a component B for the construction of a polymer network by radical polymerization.
- the complete curing of the polymerizable composition according to the invention can take place separately in time in two different process steps.
- first of all the free-radical crosslinking of the components D and E initially produces viscosity which already gives the resulting product a certain degree of dimensional stability, but without further processing, for example by bending Making pressing or embossing impossible. Only subsequent cross-linking of the isocyanate groups with one another leads to complete curing, which gives the product its final stability. This results in a uniform polymer network, since the components B and D always react with the isocyanate groups of the isocyanate component A.
- the polymerizable composition contains at least one of the two components D and E, but no component B.
- composition according to the invention contains a component B and at least one of the two components D and E. Particularly preferred is the combination of B and D.
- the polymerizable composition of the present invention preferably contains the isocyanate component A and component B in an amount that has the viscosity of the undiluted isocyanate component of at most 75%, more preferably at most 50%, even more preferably at most 33% of the viscosity of an undiluted isocyanate component A. lowers.
- the presence of at least one component D or E in this embodiment is preferred, but not mandatory.
- the proportion of component A to the total amount of components B, D and E is such that the polymerizable composition has a viscosity of at most 100,000 mPas, more preferably at most 10,000 mPas, even more preferably at most 5,000 mPas and most preferably at most 2,000 mPas.
- the above conditions are particularly satisfied when the mass ratio of components A and B is in the range of 95 to 5 to 30 to 70, preferably 95 to 5 to 50 to 50, and more preferably 92.5 to 7.5 to 70 to 30.
- the molar ratio of isocyanate groups and ethylenic double bonds is preferably in a range of 1 to 10 to 10 to 1, more preferably 1 to 5 to 8 to 1, and even more preferably 1 to 3 to 5 to 1).
- the molecular ratio of these functional groups can be determined by integrating the signals of a sample in the 13 C-NM spectrum.
- the polymer obtainable by polymerization of the polymerizable composition according to the invention obtains its advantageous properties quite substantially by crosslinking of the isocyanate groups with one another. Therefore, it is essential to the invention that the ratio of isocyanate groups to the total amount of isocyanate-reactive groups in the polymerizable Composition is limited so that a significant molar excess of isocyanate groups is present.
- the molar ratio of isocyanate groups of the isocyanate component to isocyanate-reactive groups in the polymerizable composition is therefore at least 2.0 to 1.0, preferably at least 3.0 to 1.0, more preferably at least 4.0 to 1.0 and even more preferably at least 8.0 to 1.0.
- isocyanate-reactive groups are hydroxyl, thiol, carboxyl and amino groups, amides, urethanes, acid anhydrides and epoxides
- the isocyanate groups present are contained in the components A and, if present, E.
- the isocyanate-reactive groups can in principle be present in all other components with the exception of component B.
- the use of the polymerizable composition according to the invention allows greater flexibility in the selection of the proportions of the individual components.
- the molar ratio of isocyanate groups to isocyanate-reactive groups must be close to 1: 1 if possible.
- there is a significant excess of isocyanate groups which is therefore not only acceptable, but even desirable, because the resulting polymer owes its advantageous properties quite substantially to the reaction of isocyanate groups with other isocyanate groups.
- the resulting structures in particular the isocyanurate groups, lead to polymers with particular hardness and particular resistance to chemicals. Also, isocyanurate groups already intrinsically flame-retardant, so that can be omitted for many applications of the otherwise necessary addition of flame retardants.
- isocyanate component A denotes the isocyanate component in the initial reaction mixture, in other words the sum of all compounds in the initial reaction mixture which have isocyanate groups with the exception of component E.
- the isocyanate component A is therefore used as starting material If “isocyanate component A” is used here, in particular "preparation of isocyanate component A”, then this means that isocyanate component A exists and is used as starting material
- the isocyanate component A preferably contains at least one polyisocyanate.
- polyurethanes e.g polyurethanes, polyureas and polyisocyanurates
- low molecular weight compounds eg those with uretdione, isocyanurate, allophanate, biuret, Iminooxadiazinedione and / or oxadiazinetrione structure.
- polyisocyanates refers to monomeric and / or oligomeric polyisocyanates alike, but to understand many aspects of the invention it is important to distinguish between monomeric diisocyanates and oligomeric polyisocyanates.
- Oligomeric polyisocyanates are referred to in this application. then it means polyisocyanates which are composed of at least two monomeric diisocyanate molecules, ie they are compounds which are or contain a reaction product of at least two monomeric diisocyanate molecules.
- oligomeric polyisocyanates from monomeric diisocyanates is also referred to herein as modifying monomeric diisocyanates.
- This "modification” as used herein means the reaction of monomeric diisocyanates to oligomeric polyisocyanates having uretdione, isocyanurate, allophanate, biuret, iminooxadiazinedione and / or oxadiazinetrione structure.
- hexamethylene diisocyanate is a "monomeric diisocyanate” because it contains two isocyanate groups and is not a reaction product of at least two polyisocyanate molecules:
- reaction products of at least two HDI molecules which still have at least two isocyanate groups are "oligomeric polyisocyanates.”
- oligomeric polyisocyanates are, for example, HDI isocyanurate and HDI starting from the monomeric HDI Biuret, each composed of three monomeric HDI building blocks:
- the weight fraction of isocyanate groups based on the total amount of isocyanate component A is at least 15% by weight.
- the isocyanate component A may consist essentially of monomeric polyisocyanates or substantially of oligomeric polyisocyanates. But it can also contain oligomeric and monomeric polyisocyanates in any mixing ratios.
- the isocyanate component A used as starting material in the trimerization is low in monomer (i.e., low in monomeric diisocyanates) and already contains oligomeric polyisocyanates.
- the terms "low in monomer” and “low in monomeric diisocyanates” are used interchangeably herein with respect to isocyanate component A.
- the isocyanate component A is a proportion of monomeric diisocyanates in the isocyanate component A of at most 20 wt .-%, in particular at most 15 wt .-% or at most 10 wt .-%, each based on the weight of the isocyanate component A, has.
- the isocyanate component A has a content of monomeric diisocyanates of at most 5 wt .-%, preferably at most 2.0 wt .-%, particularly preferably at most 1.0 wt .-%, each based on the weight of the isocyanate component A, on.
- the isocyanate component A is substantially free of monomeric diisocyanates.
- substantially free means that the content of monomeric diisocyanates is at most 0.5% by weight, based on the weight of the isocyanate component A.
- Isocyanate component A completely or at least 80, 85, 90, 95, 98, 99 or 99.5 wt .-%, each based on the weight of the isocyanate component A, of oligomeric polyisocyanates.
- a content of oligomeric polyisocyanates of at least 99 wt .-% is preferred.
- This Content of oligomeric polyisocyanates refers to the isocyanate component A as provided. That is, the oligomeric polyisocyanates are not formed during the process according to the invention as an intermediate, but are already at the beginning of the reaction in the isocyanate component used as starting material A before.
- Polyisocyanate compositions which are low in monomer or substantially free of monomeric isocyanates can be obtained by carrying out, after the actual modification reaction, in each case at least one further process step for separating off the unreacted excess monomeric diisocyanates.
- This monomer removal can be carried out in a particularly practical manner by processes known per se, preferably by thin-layer distillation under high vacuum or by extraction with suitable isocyanate-inert solvents, for example aliphatic or cycloaliphatic hydrocarbons, such as pentane, hexane, heptane, cyclopentane or cyclohexane.
- the novel isocyanate component A is obtained by modifying monomeric diisocyanates with subsequent removal of unreacted monomers.
- a low-monomer isocyanate component A contains a monomeric foreign diisocyanate.
- monomeric foreign diisocyanate means that it differs from the monomeric diisocyanates used to prepare the oligomeric polyisocyanates contained in the isocyanate component A.
- additive of monomeric foreign diisocyanate may be used to achieve special technical effects, such as e.g. be advantageous to a particular hardness. Particularly practical results are obtained when the isocyanate component A is a proportion of monomeric foreign diisocyanate in the isocyanate component A of at most 20 wt .-%, in particular at most 15 wt .-% or at most 10 wt .-%, each based on the weight of the isocyanate component A, has.
- the isocyanate component A preferably has a monomeric foreign diisocyanate content of at most 5% by weight, preferably at most 2.0% by weight, particularly preferably at most 1.0% by weight, based in each case on the weight of the isocyanate component A.
- the isocyanate component A contains monomeric monoisocyanates or monomeric isocyanates having an isocyanate functionality greater than two, ie having more than two isocyanate groups per molecule.
- monomeric monoisocyanates or monomeric isocyanates having an isocyanate functionality greater than two has been found to be advantageous for affecting the network density of the coating.
- the isocyanate component A is a proportion of monomeric monoisocyanates or monomeric Isocyanates having an isocyanate functionality greater than two in the isocyanate component A of at most 20 wt .-%, in particular at most 15 wt .-% or at most 10 wt .-%, each based on the weight of the isocyanate component A.
- the isocyanate component A has a content of monomeric monoisocyanates or monomeric isocyanates having an isocyanate functionality greater than two of at most 5 wt .-%, preferably at most 2.0 wt .-%, particularly preferably at most 1.0 wt .-%, each based on the weight of the isocyanate component A, on.
- no monomeric monoisocyanate or monomeric isocyanate with an isocyanate functionality greater than two is used.
- the oligomeric polyisocyanates may in particular have uretdione, isocyanurate, allophanate, biuret, iminooxadiazinedione and / or oxadiazinetrione structures.
- the oligomeric polyisocyanates have at least one of the following oligomeric structural types or mixtures thereof:
- an isocyanate component A is used whose Isocyanurat Modellanteil
- an isocyanate component A is used whose isocyanurate structure content is at least 50 mol%, preferably at least 60 mol%, more preferably at least 70 mol%, even more preferably at least 80 mol%, even more preferably at least 90 mol % and particularly preferably at least 95 mol% based on the sum of the oligomeric structures present from the group consisting of uretdione, isocyanurate, allophanate, biuret, Iminooxadiazindion- and Oxadiazintrion Modell in the isocyanate component A is.
- an isocyanate component A which, in addition to the isocyanurate structure, contains at least one further oligomeric polyisocyanate with uretdione, biuret, allophanate, iminooxadiazinedione and oxadiazinetrione structure and mixtures thereof.
- the proportions of uretdione, isocyanurate, allophanate, biuret, iminooxadiazinedione and / or oxadiazinetrione structure in the isocyanate component A can be determined, for example, by NM spectroscopy.
- the 13C-NMR spectroscopy preferably proton-decoupled, may preferably be used in this case since the stated oligomeric structures give characteristic signals.
- an oligomeric isocyanate component A to be used in the process according to the invention and / or the oligomeric polyisocyanates contained therein preferably has an (average) NCO Functionality of from 2.0 to 5.0, preferably from 2.3 to 4.5.
- the isocyanate component A to be used according to the invention has a content of isocyanate groups of 8.0 to 28.0% by weight, preferably from 14.0 to 25.0% by weight, in each case based on the weight of the Isocyanate component A, has.
- the isocyanate component A according to the invention is defined by containing oligomeric polyisocyanates consisting of monomeric diisocyanates, regardless of the type of modification reaction used, while maintaining a degree of oligomerization of 5 to 45%, preferably 10 to 40% preferably 15 to 30% were obtained.
- degree of oligomerization is meant the percentage of isocyanate groups originally present in the starting mixture which is consumed during the production process to form uretdione, isocyanurate, allophanate, biuret, iminooxadiazinedione and / or oxadiazinetrione structures.
- Suitable polyisocyanates for preparing the isocyanate component A to be used in the process according to the invention and the monomeric and / or oligomeric polyisocyanates contained therein are any polyisocyanates obtainable in various ways, for example by phosgenation in the liquid or gas phase or on a phosgene-free route, for example by thermal urethane cleavage , Particularly good results are obtained when the polyisocyanates are monomeric diisocyanates.
- Preferred monomeric diisocyanates are those which have a molecular weight in the range of 140 to 400 g / mol, with aliphatic, cycloaliphatic, araliphatic and / or aromatically bonded isocyanate groups, such as.
- BDI 1,4- Diisocyanatobutane
- PDI 1,5-diisocyanato-pentane
- HDI 1,6-diisocyanatohexane
- 2-methyl-1,5-diisocyanato-pentane 1,5-diisocyanato-2,2-dimethyl-pentane
- 2,2,4 or 2,4,4-trimethyl-1,6-diisocyanatohexane 1,10-diisocyanatodecane
- 1,3- and 1,4-diisocyanatocyclohexane 1,4-diisocyanato-3,3,5-trimethylcyclohexane
- l 3-diisocyanato-2-methylcyclohexane
- 1,3-diisocyanato-4-methylcyclohexane 1,isocyanato-3,3,5-trimethyl-5-isocyanatomethylcyclohexane (isophorone diiso
- Suitable monomeric monoisocyanates which can optionally be used in the isocyanate component A are, for example, n-butyl isocyanate, n-amyl isocyanate, n-hexyl isocyanate, n-heptyl isocyanate, n-octyl isocyanate, undecyl isocyanate, dodecyl isocyanate, tetradecyl isocyanate, cetyl isocyanate, stearyl isocyanate, cyclopentyl isocyanate, cyclohexyl isocyanate, 3- or 4-methylcyclohexyl isocyanate or any mixtures of such monoisocyanates.
- isocyanate component A As a monomeric isocyanate having an isocyanate functionality greater than two, which may optionally be added to the isocyanate component A, is exemplified by 4-isocyanatomethyl-l, 8-octane diisocyanate (triisocyanatononane, TIN).
- the isocyanate component A contains at most 30% by weight, in particular at most 20% by weight, at most 15% by weight, at most 10% by weight, at most 5% by weight or at most 1% by weight. %, in each case based on the weight of the isocyanate component A, of aromatic polyisocyanates.
- aromatic polyisocyanate means a polyisocyanate having at least one aromatic-bonded isocyanate group.
- aromatically bound isocyanate groups is meant isocyanate groups which are bonded to an aromatic hydrocarbon radical.
- an isocyanate component A which has exclusively aliphatically and / or cycloaliphatically bonded isocyanate groups.
- aliphatic or cycloaliphatic bound isocyanate groups is meant isocyanate groups which are bonded to an aliphatic or cycloaliphatic hydrocarbon radical.
- an isocyanate component A is used which consists of or contains one or more oligomeric polyisocyanates, the one or more oligomeric polyisocyanates having exclusively aliphatically and / or cycloaliphatically bonded isocyanate groups.
- the isocyanate component A is at least 70, 80, 85, 90, 95, 98 or 99 wt .-%, each based on the weight of the isocyanate component A, of polyisocyanates exclusively aliphatic and / or cycloaliphatic bound Having isocyanate groups. Practical experiments have shown that particularly good results can be achieved with isocyanate components A in which the oligomeric polyisocyanates contained therein have exclusively aliphatically and / or cycloaliphatically bonded isocyanate groups.
- a polyisocyanate A composition which consists of or contains one or more oligomeric polyisocyanates, wherein the one or more oligomeric polyisocyanates based on 1,4-diisocyanatobutane (BDI), 1,5-diisocyanatopentane (PDI), 1,6-diisocyanatohexane (HDI), isophorone diisocyanate (IPDI) or 4,4'-diisocyanatodicyclohexylmethane (H 12MDI) or mixtures thereof.
- BDI 1,4-diisocyanatobutane
- PDI 1,5-diisocyanatopentane
- HDI 1,6-diisocyanatohexane
- IPDI isophorone diisocyanate
- H 12MDI 4,4'-diisocyanatodicyclohexylmethane
- isocyanate components A having a viscosity of greater than 500 mPas and less than 200,000 mPas, preferably greater than 1,000 mPas and less than 100,000 mPas, more preferably greater than 1,000 mPas and less than 50,000 mPas and even more preferably greater than 1,000 mPas and less 25,000 mPas, measured according to DIN EN ISO 3219 at 21 ° C, used.
- component B all compounds are suitable which contain at least one ethylenic double bond.
- This ethylenic double bond is crosslinkable by a radical reaction mechanism with other ethylenic double bonds.
- This condition preferably fulfills activated double bonds located between the - and the ⁇ -carbon atom adjacent to an activating group.
- the activating group is preferably a carboxyl or carbonyl group.
- component B is an acrylate, a methacrylate, the ester of an acrylate or the esters of a methacrylate.
- the Component B no isocyanate-reactive groups as defined above in this application and no isocyanate groups.
- Preferred components B are components B1 with one, components B2 with two and components B3 with three of the ethylenic double bonds described above. Particularly preferred are Bl and / or B2.
- component B used is a mixture of at least one component B1 and at least one component B2.
- a mixture of at least one component Bl and at least one component B3 is used as component B.
- component B is a mixture of at least one component B2 and at least one component B3.
- component B a mixture of at least one component Bl, at least component B2 and at least one component B3 is used.
- a mixture of at least one component Bl with at least one component B2 is used.
- the mass ratio of the components Bl and B2 is preferably between 30: 1 and 1: 30, more preferably between 20: 1 and 1:20, even more preferably between 1:10 and 10: 1, and most preferably between 2: 1 and 1: 2.
- Preferred components Bl are methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate, iso-propyl (meth) acrylate, butyl (meth) acrylate, isobutyl (meth) acrylate, tert-butyl (meth) acrylate, hexyl (meth) acrylate, heptyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, cyclohexyl (meth) acrylate, octyl (meth) acrylate, iso-octyl (meth) acrylate, decyl (meth) acrylate, benzyl ( meth) acrylate, tetrahydrofurfuryl (meth) acrylate, octadecyl (meth) acrylate, dodecyl (meth) acrylate,
- Preferred components B2 are vinyl (meth) acrylate, tetraethylene glycol di (meth) acrylate, dipropylene glycol di (meth) acrylates, 1,6-hexanediol di (meth) acrylate, neopentyl glycol propoxylate di (meth) acrylate, tripropylene glycol di (meth) acrylate, bisphenol A ethoxylated di (meth ) acrylate, ethylene glycol di (meth) acrylate, propylene glycol di (meth) acrylate, neopentyl glycol di (meth) acrylate, hexamethylene glycol di (meth) acrylate, bisphenol A di (meth) acrylate and 4,4'-bis (2- (meth) acryloyloxyethoxy) diphenylpropane , Preferred components B3 are ethoxylated trimethylolpropane tri (meth) acrylate, propoxy
- the trimerization catalyst C may be mixed from one or more types of catalyst but contains at least one catalyst which effects the trimerization of isocyanate groups to isocyanurates or iminooxadiazinediones.
- Suitable catalysts for the process according to the invention are, for example, simple tertiary amines, such as e.g. Triethylamine, tributylamine, ⁇ , ⁇ -dimethylaniline, N ethylpiperidine or N, N'-dimethylpiperazine.
- Suitable catalysts are also the tertiary hydroxyalkylamines described in GB 2 221 465, e.g. Triethanolamine, N-methyldiethanolamine, dimethylethanolamine, N-isopropyldiethanolamine and 1- (2-hydroxyethyl) pyrrolidine, or those known from GB 2 222 161, from mixtures of tertiary bicyclic amines, e.g. DBU, with simple low molecular weight aliphatic alcohols existing catalyst systems.
- simple tertiary amines such as e.g. Triethylamine, tributylamine, ⁇ , ⁇ -dimethylani
- trimerization catalysts for the process according to the invention is a multiplicity of different metal compounds.
- Suitable examples are the octoates and naphthenates described in DE-A 3 240 613 as catalysts of manganese, iron, cobalt, nickel, copper, zinc, zirconium, cerium or lead or mixtures thereof with acetates of lithium, sodium, potassium, calcium or Barium, the known from DE-A 3 219 608 sodium and potassium salts of linear or branched alkanecarboxylic acids having up to 10 C-atoms, such as propionic acid, butyric acid, valeric acid, caproic acid, heptanoic acid, caprylic acid, pelargonic acid, capric acid and undecylic acid , the alkali metal or alkaline earth metal salts of aliphatic, cycloaliphatic or aromatic mono- and polycarboxylic acids having 2 to 20 C atoms, such as, for example, sodium or potassium benzoate, which are known from EP
- trimerization catalysts for the process according to the invention are, for example, the quaternary ammonium hydroxides known from DE-A 1 667 309, EP-A 0 013 880 and EP-A 0 047 452, such as, for example, US Pat. tetraethylammonium,
- Trimethylbenzylammonium hydroxide N, N-dimethyl-N-dodecyl-N- (2-hydroxyethyl) ammonium hydroxide, N- (2-hydroxyethyl) -N, N-dimethylN- (2,2'-dihydroxymethylbutyl) -ammonium hydroxide and (2-hydroxyethyl) -l, 4-diazabicyclo [2.2.2] octane hydroxide (monoadduct of ethylene oxide and water on 1,4-diazabicyclo [2.2.2] octane) obtained from EP-A 37 65 or EP -A 10 589 known quaternary hydroxyalkylammonium hydroxides, such as N, N, N-trimethyl-N- (2-hydroxyethyl) -ammonium hydroxide, the trialkylhydroxyalkylammonium carboxylates known from DE-A 2631733, EP-A 0 671 426, EP-A 1 5
- N, N, N-trimethyl-N-2-hydroxypropylammonium p-tert-butylbenzoate and N, N, N-trimethyl-N-2-hydroxypropylammonium 2-ethylhexanoate those known from EP-A 1 229 016 quaternary Benzylammonium carboxylates, such as N-benzyl-N, N-dimethyl-N-ethylammonium pivalate, N-benzyl-N, N-dimethyl-N-ethylammonium 2-ethylhexanoate, N-benzyl-N, N, N-tributylammonium 2-ethylhexanoate, N, N-dimethyl-N-ethyl-N- (4-methoxybenzyl) ammonium 2-ethylhexanoate or N, N, N-tributyl-N- (4-methoxybenzyl) ammonium pivalate, which are known from
- N-methyl-N, N, N-trialkylammonium fluorides with C 8 -C 10 -alkyl radicals N, N, N, N-tetra-n-butylammonium fluoride, ⁇ , ⁇ , ⁇ -trimethyl-N-benzylammonium fluoride, tetramethyl phosphonium fluoride .
- Tetraethylphosphonium fluoride or tetra-n-butylphosphonium fluoride the known from EP-A 0 798 299, EP-A 0 896 009 and EP-A 0 962 455 known quaternary ammonium and Phosphoniumpolyfluoride, such as benzyl-trimethylammoniumhydrogenpolyfluorid, from EP-A 0 668 271 known tetraalkylammonium alkyl carbonates, which are obtainable by reaction of tertiary amines with dialkyl, or betaine structurized quaternary Ammonioalkylcarbonate known from WO 1999/023128 known quaternary ammonium bicarbonates, such as choline bicarbonate, known from EP 0,102,482, from tertiary Amines and alkylating esters of acids of phosphorus available quaternary ammonium salts, such as reaction products of triethylamine, DABCO or N-
- carboxylates and phenolates with metal or ammonium ions are the anions of all aliphatic or cycloaliphatic carboxylic acids, preferably those with mono- or polycarboxylic acids having 1 to 20 C atoms.
- Suitable metal ions are derived from alkali or alkaline earth metals, manganese, iron, cobalt, nickel, copper, zinc, zirconium, cerium, tin, titanium, hafnium or lead.
- Preferred alkali metals are lithium, sodium and potassium, more preferably sodium and potassium.
- Preferred alkaline earth metals are magnesium, calcium, strontium and barium.
- sodium or potassium benzoate the alkali phenolates known from GB-PS 1 391 066 and GB-PS 1 386 399, such as.
- sodium or potassium phenolate and known from GB 809 809 alkali and alkaline earth oxides, hydroxides, carbonates, alkoxides and - phenolates.
- the trimerization catalyst C preferably contains a polyether. This is especially preferred when the catalyst contains metal ions.
- Preferred polyethers are selected from the group consisting of crown ether, diethylene glycol, polyethylene and polypropylene glycols. In the process according to the invention, it has proven to be particularly practical to use a trimerization catalyst B which contains as polyether a polyethylene glycol or a crown ether, more preferably 18-crown-6 or 15-crown-5.
- the Trimiers istskatalysator B contains a polyethylene glycol having a number average molecular weight of 100 to 1000 g / mol, preferably 300 g / mol to 500 g / mol and in particular 350 g / mol to 450 g / mol.
- Component D is a compound which defines in a molecule at least one isocyanate-reactive group as defined earlier in this application and has at least one ethylenic double bond.
- the isocyanate-reactive group of component D may also be a uretdione group.
- Ethylenic double bonds are preferably those represented by a radical reaction mechanism with other ethylenic double bonds are crosslinkable.
- Corresponding activated double bonds are defined in more detail for component B above in this application.
- Preferred components D are alkoxyalkyl (meth) acrylates having 2 to 12 carbon atoms in the hydroxyalkyl radical. Particular preference is given to 2-hydroxyethyl acrylate, the isomer mixture or 4-hydroxybutyl acrylate formed in the addition of propylene oxide onto acrylic acid.
- Component E is a compound which has both at least one isocyanate group and at least one ethylenic double bond in one molecule. It can advantageously be obtained by crosslinking a component D described in the preceding section with a monomeric or oligomeric polyisocyanate as described above in this application. This crosslinking is effected by reaction of the isocyanate-reactive groups, in this case in particular a hydroxyl, amino or thiol group, and an isocyanate group of the polyisocyanate. This is preferably catalyzed by a component G as described later in this application. But it is also any other suitable and known in the art catalyst conceivable. Also can be completely dispensed with a catalyst.
- oligomeric polyisocyanate based on hexamethylene diisocyanate or pentamethylene diisocyanate is combined with a component D selected from the group consisting of 2-hydroxyethyl acrylate, the mixture of isomers resulting from the addition of propylene oxide to acrylic acid and 4-hydroxybutyl acrylate.
- Further preferred components E are 2-isocyanatoethyl (meth) acrylate, tris (2-hydroxyethyl) isocyanate tri (meth) acrylate, vinyl isocyanate, allyl isocyanate and 3-isopropenyl, - dimethylbenzyl isocyanate
- the free-radical polymerization of the ethylenically unsaturated compounds present in the reaction mixture can be effected by actinic radiation with sufficient energy content.
- actinic radiation This is in particular UV-VIS radiation in the wave range between 200 and 500 nm.
- the polymerizable composition according to the invention need not contain any component F. However, if it is desired to dispense with the use of appropriate radiation, then the presence of at least one component F is necessary, which is suitable as an initiator of a radical polymerization of the ethylenic double bonds present in the polymerizable composition according to the invention.
- Initiators of this type have the effect, under suitable conditions, in particular on heating or the action of suitable radiation, of forming radicals which react with the ethylenic double bonds to give vinyl radicals, which in turn react in a chain reaction with further ethylenic double bonds.
- the component F contains at least one radiation-activated initiator F1 or at least one temperature-activated initiator F2. However, it may also contain a mixture of at least one radiation-activated initiator F1 and at least one temperature-activated initiator F2.
- Preferred radiation-activated initiators Fl are compounds of the unimolecular type (I) and of the bimolecular type (II).
- Suitable type (I) systems are aromatic ketone compounds, such as. As benzophenones in combination with tertiary amines, alkylbenzophenones, 4,4'-bis (dimethylamino) benzophenone (Michler's ketone), anthrone and halogenated benzophenones or mixtures of the types mentioned.
- type (II) initiators such as benzoin and its derivatives, benzil ketals, acylphosphine oxides, 2,4,6-trimethylbenzoyldiphenylphosphine oxide, bisacylphosphine oxides, phenylglyoxylic acid esters, camphorquinone, ⁇ -aminoalkylphenones, dialkoxyacetophenones and hydroxyalkylphenones.
- lrgacur ® phenyl ketone, a mixture of benzophenone and (l-hydroxycyclohexyl), Messrs.
- Ciba, Lampertheim, DE 500, Irgacure ® 819 DW (Phenylbis- (2, 4, 6-trimethylbenzoyl) phosphine oxide, Fa. Ciba, Lampertheim, DE) or Esacure ® KIP EM (oligo- [2-hydroxy-2-methyl-l- [4- (l-methylvinyl) phenyl] -propanone], Fa. Lamberti, Aldizzate, Italy) and bis ( 4-methoxybenzoyl) diethylgerman. It is also possible to use mixtures of these compounds.
- photoinitiators Care should be taken with the photoinitiators to have sufficient reactivity with the source of radiation used.
- photoinitiators There are a variety of photoinitiators known in the market. Commercially available photoinitiators cover the wavelength range in the entire UV-VIS spectrum.
- Preferred temperature-activated initiators F2 are organic azo compounds, organic peroxides and CC-cleaving initiators, such as benzpinacol silyl ethers, N, N-diacyl-hydroxylamines, O-alkylated N, N-diacyl-hydroxylamines or O-acylated N, N-diacyl-hydroxylamines. Also suitable are inorganic peroxides such as peroxodisulfates. Other suitable thermal free radical initiators are azobisisobutyronitrile (AIBN), dibenzoyl peroxide (DBPO), di-tert-butyl peroxide, dicumyl peroxide (DCP) and peroxybenzoic acid ieri-butyl ester. However, the person skilled in the art can also use all other thermal initiators known to him. Component G
- Component G is a catalyst which catalyzes the crosslinking of an isocyanate group with an isocyanate-reactive group. This is preferably a urethane group, a Thiourethanomia or a urea group.
- the polymerizable composition preferably contains a component G when a component D with at least one isocyanate-reactive group is present.
- a component G also in this case is not mandatory, since the crosslinking of isocyanate groups with isocyanate-reactive groups, the trimerization catalysts used C can be accelerated and runs well without catalysis sufficiently fast, if the reaction temperature is high enough.
- the addition of a component G can be dispensed with in particular if the crosslinking of the isocyanate groups present in the isocyanate component A is carried out at temperatures of at least 60 ° C., preferably at least 120 ° C.
- Preferred components G are the typical urethanization catalysts, as indicated, for example, in Becker / Braun, Kunststoffhandbuch Volume 7, Polyurethanes, Chapter 3.4.
- the catalyst used may in particular be a compound selected from the group of tertiary amines, tertiary amine salts, metal salts and organometallic compounds, preferably from the group of tin salts, tin organyls and bismuth organyls.
- the viscosity of the polymerizable composition according to the invention is preferably adjusted by the use of a component B in a suitable concentration. These act as reactive diluents and fundamentally make it possible to dispense with the use of additional solvents for lowering the viscosity of the isocyanate component A.
- the polymerizable composition according to the invention may contain all solvents known to those skilled in the art for the dilution of isocyanates.
- the polymerizable composition according to the invention additionally comprises at least one additive I selected from the group consisting of UV stabilizers, antioxidants, mold release agents, water scavengers, slip additives, defoamers, leveling agents, rheology additives, flame retardants and pigments.
- additives selected from the group consisting of UV stabilizers, antioxidants, mold release agents, water scavengers, slip additives, defoamers, leveling agents, rheology additives, flame retardants and pigments.
- auxiliaries and additives are usually present in an amount of at most 10% by weight, preferably at most 5% by weight and more preferably at most 3% by weight, based on the polymerizable composition of the invention.
- the polymerizable composition comprises at least one organic filler J1 and / or at least one inorganic filler J2.
- Said fillers can be present in any shape and size known to those skilled in the art.
- Preferred organic fillers J1 are wood, cellulose, paper, cardboard, tissue chips, cork, wheat chaff, polydextrose, cellulose, aramids, polyethylene, carbon, carbon nanotubes, polyesters, nylon, plexiglas, flax, hemp and sisal.
- Preferred inorganic fillers J 2 are AlOH 3 , CaCO 3 , silicon dioxide, magnesium carbonate, TiO 2 , ZnS, minerals containing silicates, sulfates, carbonates and the like, such as magnesite, barite, mica, dolomite, kaolin, talc, clay minerals, and carbon black, graphite, boron nitride , Glass, basalt, boron, ceramics and silicic acid.
- the present invention relates to the use of at least one component selected from the group consisting of components B, D and E for the preparation of a polymerizable composition having a ratio of isocyanate groups to isocyanate-reactive groups of at least 2.0 to 1.0 which is an isocyanate component A contains and is polymerizable by radical polymerization as well as by crosslinking of isocyanate groups with each other.
- At least one component B is used as defined above in this application.
- the present invention relates to a process for the preparation of a polymer comprising the steps of a) providing a polymerizable composition as described earlier in this application;
- viscosity is first built up by process step b) before the final curing of the polymer takes place in process step c).
- the two process steps do not have to follow one another directly in time. It is particularly preferred that between the two process steps, a further step takes place, in which the product of process step b) is formed.
- the polymerizable composition according to the invention does not contain a temperature-activated initiator F 2.
- a temperature-activated initiator F2 is used, since in this case the temperature increase required for the crosslinking of the isocyanate groups in process step c) also causes the crosslinking of the ethylenic double bonds in process step b).
- the method according to the invention comprises a further process step d) in which the isocyanate-reactive group of component D is crosslinked with an isocyanate group of the isocyanate component A or a reaction product of the isocyanate component A.
- Said process step d) can be carried out before process step b), it can be carried out between process steps b) and c), it can be carried out in parallel to process step b) or c) or also after process steps b) and c).
- the process step d) is preferably carried out in parallel to the process step c), since there is already an increase in temperature, which also causes the reaction of components A and D.
- the crosslinking of the ethylenic double bonds contained in the polymerizable composition according to the invention is carried out by a free-radical polymerization.
- This polymerization reaction when a radiation-activated initiator Fl is present, according to the invention by the use of radiation, which is suitable for its activation, initiated.
- a temperature-activated initiator F2 is present in the polymerizable composition used, crosslinking of the ethylenic double bonds is initiated by heating the polymerizable composition to the required temperature.
- the use of sufficiently high-energy radiation, as defined above in this application is sufficient for initiation of the free-radical polymerization in process step b), irrespective of the presence of initiators F1 or F1.
- the "crosslinking" of the isocyanate component A in process step c) is a process in which the isocyanate groups contained therein form or at least one structure selected from the group consisting of uretdione, isocyanurate, allophanate, biuret, Iminooxadiazindion- and Oxadiazintrion Modellen react with already existing urethane groups.
- the isocyanate groups originally present in the isocyanate component A are consumed.
- the monomeric and oligomeric polyisocyanates contained in isocyanate component A are combined to form a polymer network.
- the crosslinking reaction results in at most 20%, preferably at most 10%, particularly preferably at most 5%, very particularly preferably at most 2% and in particular at most 1 % of the total nitrogen content of the isocyanate component A in urethane and / or allophanate groups.
- the cured isocyanate component A is not completely free of urethane and allophanate groups. It therefore preferably contains at least 0.1% of urethane and / or allophanate groups, based on the total nitrogen content, taking into account the upper limits defined in the preceding paragraph.
- the crosslinking of the isocyanate groups present in the polymerizable composition according to the invention predominantly by cyclotrimerization of at least 50%, preferably at least 60%, more preferably at least 70%, especially at least 80% and most preferably 90% of present in the isocyanate component A.
- free isocyanate groups to Isocyanurat Modelltechniken takes place.
- corresponding proportions of the nitrogen originally contained in the isocyanate component A are bound in isocyanurate structures.
- Side reactions, especially those to uretdione, allophanate, and / or iminooxadiazinedione structures usually occur and can even be used selectively, e.g. to favorably influence the glass transition temperature (Tg) of the resulting polyisocyanurate resin.
- Tg glass transition temperature
- the content of urethane and / or allophanate groups as defined above is preferably also present in this embodiment.
- the crosslinking of the isocyanate groups is preferably carried out at temperatures between 50 ° C and 220 ° C, more preferably between 80 ° C and 200 ° C and even more preferably between 100 ° C and 200 ° C.
- the abovementioned temperatures are maintained in process step c) until at least 50%, preferably at least 75% and even more preferably at least 90% of the free isocyanate groups present in the isocyanate component A at the beginning of process step b) are consumed.
- the percentage of isocyanate groups still present can be determined by comparing the content of isocyanate groups in wt .-% in the present at the beginning of the process step b) isocyanate component A with the content of isocyanate groups in wt .-% im Reaction product, for example, by the above-mentioned comparison of the intensity of the isocyanate at about 2270 cm-1 by means of I spectroscopy determined.
- process step c) of course depends on the geometry of the workpiece to be produced, in particular the ratio of surface area and volume, since in the core of the resulting workpiece, the required temperature for the required minimum duration must be achieved. The person skilled in the art can determine these parameters by simple preliminary tests.
- crosslinking of the abovementioned proportions of free isocyanate groups is achieved if the abovementioned temperatures are kept for 1 minute to 4 hours. Particularly preferred is a period between 1 minute and 15 minutes at temperatures between 180 ° C and 220 ° C or a period of 5 minutes to 120 minutes at a temperature of 120 ° C.
- the present invention relates to a polymer obtainable by the method described above.
- the polymer is preferably present as a coating or as a shaped body.
- a “coating” is preferably characterized by being applied to a substrate, this substrate preferably being selected from the group consisting of wood, plastic, metal, natural stone, concrete, paper and glass
- the coating is particularly preferably characterized in that it has a dimension of at least 0.005 mm and at most 5 mm in one dimension and a dimension of at least 2 cm, preferably at least 2 cm, in at least one, preferably two, of the other two dimensions 3 cm.
- a "molded article” is defined as having an edge length of at least 0.5 mm, preferably at least 1 mm in at least one of the three dimensions and a dimension of at least 2 cm, preferably at least 5 cm, in at least one of the other two dimensions. It preferably has an edge length of at least 2 cm in all three dimensions.
- RT room temperature
- phase transitions were determined by means of DSC (Differential Scanning Calorimetry) using a Mettler DSC 12E (Mettler Toledo GmbH, Giessen, Germany) in accordance with DIN EN 61006. Calibration was performed by the temperature of the indium-lead melted on-set. 10 mg of substance were weighed into normal capsules. The measurement was carried out by three heats from -50 ° C to +200 ° C at a heating rate of 20 K / min with subsequent cooling at a cooling rate of 320 K / min. The cooling was carried out by liquid nitrogen. Nitrogen was used as purge gas. The given values are based on the evaluation of the 2nd heating curve. The glass transition temperature T g was obtained from the temperature at half the height of a glass transition stage.
- the infrared spectra were measured on a Bruker FT-IR spectrometer equipped with an ATR unit.
- Polyisocyanate AI HDI trimer (NCO functionality> 3) with an NCO content of 23.0 wt .-% of the company. Covestro AG. The viscosity is about 1200 mPa-s at 23 ° C (DIN EN ISO 3219 / A.3).
- Polyisocyanate A2 PDI trimer (NCO functionality> 3) with an NCO content of 21.5% by weight from Covestro AG.
- the viscosity is about 9500 mPa-s at 23 ° C (DIN EN ISO 3219 / A.3).
- Acrylate 1 hexanediol diacrylate (HDDA) was obtained with a purity of> 99% by weight from Sigma-Aldrich.
- Acrylate 2 hydroxypropyl methacrylate (HPMA) was obtained with a purity of 98 wt .-% of Fa. GmbH, but.
- IBOMA isobornyl methacrylate
- Trigonox * C peroxybenzoic acid, ieri-butyl ester
- Potassium acetate was obtained with a purity of> 99 wt .-% of the company. ACROS.
- Lucirin TPO-L is an ethyl (2,4,6-trimethylbenzoyl) phenylphosphinate from BASF obtained from the company Sigma Aldrich.
- Polyethylene glycol (PEG) 400 was obtained with a purity of> 99 wt .-% of the company. ACROS.
- Potassium acetate (5.0 g) was stirred in the PEG 400 (95.0 g) at r.t. until everything was dissolved. There was thus obtained a 5 wt .-% solution of potassium acetate in PEG 400 and used without further treatment as a catalyst.
- reaction mixture was, unless stated otherwise, by mixing polyisocyanate (A1-A2) and the acrylate / acrylates with an appropriate amount of catalyst (Kl-2), initiator and optionally additive at 23 ° C in a speed mixer DAC 150.1 FVZ Fa. Hauschild 1 and 2 minutes of mixing produced at 2750 min ". This was then either cast without further treatment for cross-linking in an appropriate shape or knife-coated onto a glass plate.
- Exemplary embodiments 1 to 20 are exemplary embodiments 1 to 20:
- the T g of the cured reaction mixtures was 70 - 128 ° C.
- the viscosities of the reaction mixtures according to the invention with polyisocyanate AI (Examples 3, 4, 6-9) were directly after preparing the mixture 0.5-0.7 Pa-s and increased over 4 h at RT to 1.0 - 2.1 Pa-s.
- the viscosity of the reaction mixture according to the invention with polyisocyanate A2 (Example 11) was 3.0 Pa-s immediately after the preparation of the mixture and increased to 5.6 Pa-s over 4 h at RT.
- Table 1 Compositions, manufacturing conditions and material properties of the embodiments 1-20.
- the reaction mixture was 250 ⁇ thick geräkelt on the tin-free side of a glass plate and then UV treated with a gallium-doped and an undoped mercury lamp. Subsequently, the samples were cured at 180 ° C for 15 min.
- Table 2 Compositions and Material Properties of Exemplary Embodiments 21-24.
- the Tg of the cured reaction mixture was 101 ° C.
- the viscosity of the comparative reaction mixtures with polyisocyanate AI was more than 2 Pa-s immediately after the preparation of the mixture and increased to more than 3.5 Pa-s within 4 h.
- the starting viscosity when mixed with acrylates was markedly lower (0.5-0.7 Pa.s) and, even after 4 h at RT, had lower values (1.0-2.0 Pa). s) as the starting viscosity of the comparative experiment.
- the material properties (for example Tg) of the materials according to the invention were of a comparable order of magnitude.
- the Tg of the cured reaction mixture was 137 ° C.
- the reaction mixture is 250 ⁇ thick geräkelt on the tin-free side of a glass plate and then UV-treated with a gallium-doped and an undoped mercury lamp, wherein the reaction mixture is not changed and a drain can be determined.
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Abstract
Description
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EP16198688 | 2016-11-14 | ||
PCT/EP2017/079209 WO2018087396A1 (de) | 2016-11-14 | 2017-11-14 | Isocyanuratpolymere mit dualer härtung |
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EP17797645.3A Active EP3538584B1 (de) | 2016-11-14 | 2017-11-14 | Verfahren zur herstellung eines gegenstandes aus einem vorläufer und verwendung eines radikalisch vernetzbaren harzes in einem additiven fertigungsverfahren |
EP17794993.0A Pending EP3538583A1 (de) | 2016-11-14 | 2017-11-14 | Isocyanuratpolymere mit dualer härtung |
EP17801426.2A Pending EP3538585A1 (de) | 2016-11-14 | 2017-11-14 | Kompositwerkstoffe basierend auf isocyanuratpolymeren mit dualer härtung |
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EP17801429.6A Pending EP3538586A1 (de) | 2016-11-14 | 2017-11-14 | Beschichtungszusammensetzungen mit dualer härtung |
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BR112017010875A2 (pt) | 2014-11-24 | 2018-01-09 | Ppg Ind Ohio Inc | método para impressão tridimensional de um objeto e objeto tridimensional |
US10434704B2 (en) | 2017-08-18 | 2019-10-08 | Ppg Industries Ohio, Inc. | Additive manufacturing using polyurea materials |
US11007711B2 (en) * | 2017-11-09 | 2021-05-18 | Covestro Deutschland Ag | Process for manufacturing an object, and use of a radically cross-linkable resin in an additive manufacturing process |
EP3743449B1 (de) * | 2017-11-14 | 2024-04-17 | Covestro Deutschland AG | Halbzeuge basierend auf dualem vernetzungsmechanismus |
GB201819984D0 (en) | 2018-12-07 | 2019-01-23 | Ge Healthcare Bio Sciences Ab | Chromatography column and method of assembling the same |
KR20210122823A (ko) | 2019-02-01 | 2021-10-12 | 바스프 에스이 | 폴리우레탄 및 이를 포함하는 uv-수분 이중 경화 pu 반응성 핫멜트 |
WO2021002479A1 (ja) * | 2019-07-04 | 2021-01-07 | 株式会社リコー | 立体造形物の製造方法及び製造装置、並びに、立体造形用硬化液、及び立体造形用キット |
US20220153910A1 (en) * | 2020-11-18 | 2022-05-19 | Covestro Llc | Polyurethane and polyisocyanurate hybrid coatings |
US20220153911A1 (en) * | 2020-11-18 | 2022-05-19 | Covestro Llc | Polyurethane and polyisocyanurate hybrid materials and method of preparing the same |
JP2024514474A (ja) | 2021-03-29 | 2024-04-02 | コベストロ、ドイチュラント、アクチエンゲゼルシャフト | ポリイソシアヌレート-プリプレグおよびそれから製造される繊維複合コンポーネント |
EP4092064A1 (de) | 2021-05-17 | 2022-11-23 | Covestro Deutschland AG | Licht- und wärmehärtbares harz zur generativen fertigung |
EP4116348A1 (de) | 2021-07-09 | 2023-01-11 | Covestro Deutschland AG | Photo- und wärmehärtbares harz zur verwendung in additiven fertigungsverfahren |
EP4166331A1 (de) * | 2021-10-12 | 2023-04-19 | Covestro Deutschland AG | Licht- und wärmehärtbares harz zur verwendung in generativen fertigungsverfahren |
CN115160908B (zh) * | 2022-07-06 | 2023-07-07 | 海利得新材料研究(上海)有限公司 | 无溶剂uv哑光涂料及其制备方法 |
Family Cites Families (121)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB809809A (en) | 1956-11-16 | 1959-03-04 | Ici Ltd | Polymeric isocyanates and their manufacture |
GB952931A (en) | 1961-05-25 | 1964-03-18 | Ici Ltd | Improved polyisocyanate compositions |
GB966338A (en) | 1961-10-26 | 1964-08-12 | Ici Ltd | Polyurethane surface coatings |
US3211703A (en) | 1962-03-23 | 1965-10-12 | Monsanto Res Corp | Polyaliphatic polyisocyanurate laminating resin prepared in the presence of a cocatalyst system |
DE1226109B (de) | 1964-04-20 | 1966-10-06 | Bayer Ag | Verfahren zur Herstellung von Polyisocyanaten mit Isocyanuratstruktur |
CA932333A (en) | 1966-02-02 | 1973-08-21 | Farbenfabriken Bayer Aktiengesellschaft | Compounds containing the 2,4,6-triketo-1,3,5-oxadiazine ring |
DE1667309C3 (de) | 1967-01-19 | 1978-10-26 | Takeda Chemical Industries, Ltd., Osaka (Japan) | Verfahren zur Herstellung von Isocyanattrimere!! |
DE1954093C3 (de) | 1968-11-15 | 1978-12-21 | Mobay Chemical Corp., Pittsburgh, Pa. (V.St.A.) | Verfahren zur Herstellung von polymeren organischen Isocyanaten |
GB1386399A (en) | 1971-07-16 | 1975-03-05 | Ici Ltd | Isocyanurate polymers |
GB1391066A (en) | 1971-07-16 | 1975-04-16 | Ici Ltd | Urethane oils |
BE795448A (nl) * | 1972-02-24 | 1973-08-16 | Shell Int Research | Werkwijze voor de bereiding van hardbare composities |
DE2414413C3 (de) | 1974-03-26 | 1978-08-24 | Bayer Ag, 5090 Leverkusen | Verwendung von Lösungen von Polyisocyanaten mit Isocyanuratstruktur in Zweikomponenten-Polyurethan-Lacken |
DE2452532C3 (de) | 1974-11-06 | 1978-08-24 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von Polyisocyanaten mit Isocyanurat-Struktur |
US4040992A (en) | 1975-07-29 | 1977-08-09 | Air Products And Chemicals, Inc. | Catalysis of organic isocyanate reactions |
DE2641380C2 (de) | 1976-09-15 | 1989-11-23 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von Polyisocyanaten mit Isocyanuratstruktur |
DE2722400C2 (de) * | 1977-05-17 | 1985-05-30 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von wärmebeständigen, blasenfreien Isocyanuratgruppen aufweisenden Kunststoffen |
US4128537A (en) | 1977-07-27 | 1978-12-05 | Ici Americas Inc. | Process for preparing ethylenically unsaturated isocyanurates |
EP0000659B1 (de) * | 1977-07-27 | 1981-09-09 | Ici Americas Inc. | Durch Trimerisation eines isocyanatgruppenhaltigen Urethans aus einem aromatischen Polyisocyanat und einem Vinylidencarbonyloxyalkanol gebildete Isocyanurat-Zusammensetzung und daraus erhaltene Lösungen, Polymere und Laminate. |
US4145544A (en) | 1977-07-27 | 1979-03-20 | Ici Americas Inc. | Preparation of isocyanurates |
US4159376A (en) | 1977-07-27 | 1979-06-26 | Ici Americas Inc. | Isocyanurates from unsaturated monohydric alcohols and polyisocyanates |
DE2806731A1 (de) | 1978-02-17 | 1979-08-23 | Bayer Ag | Verfahren zur herstellung von isocyanuratgruppen aufweisenden polyisocyanaten |
US4232133A (en) * | 1978-07-27 | 1980-11-04 | Ici Americas Inc. | Polyisocyanurate containing molding compositions |
US4296215A (en) * | 1978-07-27 | 1981-10-20 | Ici Americas Inc. | Method to thicken dissolved thermoset resins |
CA1112243A (en) | 1978-09-08 | 1981-11-10 | Manfred Bock | Process for the preparation of polyisocyanates containing isocyanurate groups and the use thereof |
DE2901479A1 (de) | 1979-01-16 | 1980-07-24 | Bayer Ag | Neue isocyanato-isocyanurate, ein verfahren zu ihrer herstellung, sowie ihre verwendung als isocyanatkomponente in polyurethan-lacken |
CA1127644A (en) | 1980-01-28 | 1982-07-13 | Anupama Mishra | Isocyanurate products and polyurethanes therefrom |
DE3033860A1 (de) | 1980-09-09 | 1982-04-15 | Bayer Ag, 5090 Leverkusen | Neue isocyanato-isocyanurate, ein verfahren zu ihrer herstellung, sowie ihre verwendung als isocyanatkomponente in polyurethanlacken |
DE3100263A1 (de) | 1981-01-08 | 1982-08-12 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von isocyanuratgruppen aufweisenden polyisocyanaten und ihre verwendung bei der herstellung von polyurethanen |
DE3100262A1 (de) | 1981-01-08 | 1982-08-05 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von isocyanuratgruppen aufweisenden polyisocyanaten, als katalysator-komponente fuer dieses verfahren geeignete loesungen, sowie die verwendung der verfahrensprodukte als isocyanat-komponente bei der herstellung von polyurethanen |
US4352906A (en) * | 1981-08-06 | 1982-10-05 | Ici Americas Inc. | Blister resistant calcium carbonate filled polyisocyanurate resin molding compositions |
JPS58162581A (ja) | 1982-03-19 | 1983-09-27 | Nippon Polyurethan Kogyo Kk | ポリウレタン塗料用組成物 |
DE3227489A1 (de) | 1982-07-23 | 1984-01-26 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von isocyanuratgruppen aufweisenden polyisocyanaten und ihre verwendung als isocyanatkomponente zur herstellung von polyurethanen |
PT77070B (en) | 1982-07-29 | 1986-01-27 | Dsm Resins Bv | Oligomerisation of polyisocyanates |
AT375652B (de) | 1982-10-29 | 1984-08-27 | Valentina Alexandro Postnikova | Verfahren zur herstellung von arylaliphatischen polyisozyanuraten |
JPH0641501B2 (ja) * | 1984-04-30 | 1994-06-01 | 旭オーリン株式会社 | 重合体生成物の製造法 |
JPH0641500B2 (ja) * | 1984-04-30 | 1994-06-01 | 旭オーリン株式会社 | 重合体生成物の製造方法 |
DE3521618A1 (de) | 1985-06-15 | 1986-12-18 | Bayer Ag, 5090 Leverkusen | In wasser dispergierbare polyisocyanat-zubereitung und ihre verwendung als zusatzmittel fuer waessrige klebstoffe |
JPH0678418B2 (ja) | 1986-03-10 | 1994-10-05 | 大日本インキ化学工業株式会社 | 樹脂組成物 |
JP2598391B2 (ja) * | 1986-03-24 | 1997-04-09 | 三菱化学株式会社 | 磁気記録媒体の製造方法 |
DE3700209A1 (de) | 1987-01-07 | 1988-07-21 | Bayer Ag | Verfahren zur herstellung von polyisocyanaten mit biuretstruktur |
DE3737244A1 (de) | 1987-11-03 | 1989-05-18 | Bayer Ag | Verfahren zur herstellung von isocyanuratgruppen und olefinische doppelbindungen aufweisenden verbindungen und ihre verwendung als bindemittel |
DE3811350A1 (de) | 1988-04-02 | 1989-10-19 | Bayer Ag | Verfahren zur herstellung von isocyanuratpolyisocyanaten, die nach diesem verfahren erhaltenen verbindungen und ihre verwendung |
DE3814167A1 (de) | 1988-04-27 | 1989-11-09 | Bayer Ag | Verfahren zur herstellung von isocyanuratgruppen aufweisenden polyisocyanaten und ihre verwendung |
DE3819627A1 (de) | 1988-06-09 | 1989-12-14 | Bayer Ag | Uv-haertbare beschichtungen fuer polycarbonatformkoerper |
US5130402A (en) * | 1988-07-01 | 1992-07-14 | Sanyo Chemical Industries, Ltd. | Coating composition and plastisol composition, and articles coated therewith |
CA1334848C (en) | 1988-08-05 | 1995-03-21 | William E. Slack | Process for the production of polyisocyanates which contain isocyanurate groups |
CA1334849C (en) | 1988-08-24 | 1995-03-21 | Bayer Corporation | Process for the production of polyisocyanates which contain isocyanurate groups |
US4855383A (en) * | 1988-09-23 | 1989-08-08 | Ashland Oil, Inc. | In situ quaternary ammonium catalyst formation for curing polymeric isocyanates |
DE3900053A1 (de) | 1989-01-03 | 1990-07-12 | Bayer Ag | Verfahren zur herstellung von uretdion- und isocyanuratgruppen aufweisenden polyisocyanaten, die nach diesem verfahren erhaeltlichen polyisocyanate und ihre verwendung in zweikomponenten-polyurethanlacken |
DE3902078A1 (de) | 1989-01-25 | 1990-07-26 | Bayer Ag | Verfahren zur herstellung von modifizierten, isocyanuratgruppen aufweisenden polyisocyanaten und ihre verwendung |
US5091496A (en) * | 1989-05-19 | 1992-02-25 | Mitsui Toatsu Chemicals, Inc. | Polyisocyanatoalkylphenyl-isocyanurates, method for the preparation thereof and use thereof |
DE3928503A1 (de) | 1989-08-29 | 1991-03-07 | Bayer Ag | Verfahren zur herstellung von loesungen von isocyanuratgruppen aufweisenden polyisocyanaten in lackloesungsmitteln und ihre verwendung |
DE4005762A1 (de) | 1990-02-23 | 1991-08-29 | Bayer Ag | Trimerisierungskatalysatoren, ein verfahren zu ihrer herstellung und ihre verwendung bei der herstellung von isocyanuratgruppen aufweisenden polyisocyanaten |
US5234970A (en) * | 1991-07-16 | 1993-08-10 | W. R. Grace & Co.-Conn. | Dual curing composition based on isocyanate trimer and use thereof |
GB9116781D0 (en) * | 1991-08-02 | 1991-09-18 | Ici Plc | Curable compositions |
US5322861A (en) * | 1991-10-01 | 1994-06-21 | Mitsubishi Kasei Corporation | Ultraviolet-hardening urethane acrylate oligomer |
DE4136618A1 (de) | 1991-11-07 | 1993-05-13 | Bayer Ag | Wasserdispergierbare polyisocyanatgemische |
IT1255279B (it) * | 1992-05-20 | 1995-10-26 | Sir Ind Spa | Composizioni poliestere/isocianato reticolabili adatte alla preparazione di manufatti in composito particolarmente con processi ad iniezione, procedimento per la loro preparazione e loro utilizzo |
US5370908A (en) | 1993-05-24 | 1994-12-06 | Olin Corporation | Low VOC, heat-curable, one-component and two-component coating compositions based on organic polyisocyanates |
DE4405055A1 (de) | 1994-02-17 | 1995-08-24 | Basf Ag | Verfahren zur Herstellung von Isocyanuratgruppen aufweisenden Polyisocyanaten und ihre Verwendung |
DE4405054A1 (de) | 1994-02-17 | 1995-08-24 | Basf Ag | Modifizierte (cyclo)aliphatische Polyisocyanatmischungen, Verfahren zu ihrer Herstellung und ihre Verwendung |
JPH07329191A (ja) * | 1994-06-09 | 1995-12-19 | Denken Eng Kk | 光造形法 |
DE19611849A1 (de) | 1996-03-26 | 1997-10-02 | Bayer Ag | Neue Isocyanattrimerisate und Isocyanattrimerisatmischungen, deren Herstellung und Verwendung |
AU727418B2 (en) * | 1997-04-01 | 2000-12-14 | Huntsman Ici Chemicals Llc | Polyisocyanate based xerogels |
DE19734048A1 (de) | 1997-08-06 | 1999-02-11 | Bayer Ag | Verfahren zur Herstellung von Polyisocyanaten, damit hergestellte Polyisocyanate und deren Verwendung |
ZA9810038B (en) | 1997-11-04 | 2000-05-03 | Rhodia Chimie Sa | A catalyst and a method for the trimerization of isocyanates. |
DE19818312A1 (de) * | 1998-04-23 | 1999-10-28 | Bayer Ag | Wäßriges Beschichtungssytem aus UV-härtenden Isocyanatgruppen aufweisenden Urethan(meth)acrylatisocyanaten |
ATE225777T1 (de) | 1998-06-02 | 2002-10-15 | Bayer Ag | Verfahren zur herstellung iminooxadiazindiongruppen enhaltender polyisocyanate |
DE19929064A1 (de) * | 1999-06-25 | 2000-12-28 | Bayer Ag | Verfahren zur Herstellung Uretdiongruppen aufweisender Polyadditionsverbindungen |
MXPA02003155A (es) * | 1999-09-30 | 2002-09-30 | Basf Ag | Dispersiones de poliuretano acuosas las cuales se pueden endurecer con radiacion uv y termicamente, y uso de las mismas. |
ATE321032T1 (de) * | 2000-01-20 | 2006-04-15 | Rhodia Chimie Sa | Verfahren zur herstellung von schwach gefärbten, verzweigten polyisocyanaten und daraus resultierende zusammensetzung |
DE10016194A1 (de) * | 2000-03-31 | 2001-10-04 | Bayer Ag | Beschichtungssystem enthaltend UV-härtbare, Isocyanatgruppen aufweisende Urethan(meth)acrylate und Hydroxylgruppen aufweisende Urethan(meth)acrylate |
DE10041634C2 (de) * | 2000-08-24 | 2002-10-17 | Basf Coatings Ag | Wäßrige Dispersion und ihre Verwendung zur Herstellung von thermisch und mit aktinischer Strahlung härtbaren Beschichtungsstoffen, Klebstoffen und Dichtungsmassen |
DE10065176A1 (de) | 2000-12-23 | 2002-06-27 | Degussa | Katalysator und Verfahren zur Herstellung von niedrigviskosen und farbreduzierten isocyanuratgruppenhaltigen Polyisocyanaten |
JP2004217808A (ja) * | 2003-01-16 | 2004-08-05 | Mitsubishi Chemicals Corp | 活性エネルギー線硬化性樹脂組成物並びにそれを用いた印刷インキ用バインダー及び積層シート |
MXPA05009155A (es) | 2003-02-28 | 2005-10-20 | Dow Global Technologies Inc | Preparacion de mezclas e poliisocianato conteniendo grupo de isocianurato. |
JP2004315617A (ja) | 2003-04-14 | 2004-11-11 | Mitsubishi Rayon Co Ltd | 立体造形用組成物、及び立体造形物 |
JP2005015627A (ja) | 2003-06-26 | 2005-01-20 | Jsr Corp | 光硬化性液状樹脂組成物 |
DE102004012571A1 (de) | 2004-03-12 | 2005-09-29 | Basf Ag | Verfahren zur Herstellung von Isocyanuratgruppen aufweisenden Polyisocyanaten und ihre Verwendung |
DE102004043537A1 (de) * | 2004-09-09 | 2006-03-16 | Bayer Materialscience Ag | Herstellung von neuen strahlenhärtenden Bindemitteln |
DE102004063102A1 (de) * | 2004-12-22 | 2006-07-13 | Basf Ag | Strahlungshärtbare Verbindungen |
CN101268103A (zh) * | 2005-09-22 | 2008-09-17 | 纳幕尔杜邦公司 | 在树脂基质上产生粘附涂层的方法 |
EP1941322B1 (de) * | 2005-10-27 | 2018-05-30 | 3D Systems, Inc. | Antimonfreie lichthärtbare harzzusammensetzung und dreidimensionaler artikel |
DE102005057682A1 (de) * | 2005-12-01 | 2007-06-06 | Basf Ag | Strahlungshärtbare wasserelmulgierbare Polyisocyanate |
US20070299242A1 (en) * | 2006-06-21 | 2007-12-27 | Bayer Materialscience Llc | Pendant acrylate and/or methacrylate-containing polyether monols and polyols |
DE102006051897A1 (de) * | 2006-10-31 | 2008-05-08 | Bayer Materialscience Ag | Bedruckte, verformbare Folien |
CN101284955B (zh) * | 2007-04-11 | 2011-03-30 | 比亚迪股份有限公司 | 一种双重固化涂料组合物及其制备方法 |
JP2011503309A (ja) * | 2007-11-19 | 2011-01-27 | サイテック サーフェース スペシャリティーズ、エス.エイ. | 照射硬化性組成物 |
CN102272181A (zh) * | 2008-11-10 | 2011-12-07 | 陶氏环球技术有限责任公司 | 异氰酸酯三聚催化剂体系,前体制剂,使异氰酸酯三聚的方法,由其制备的硬质聚异氰脲酸酯/聚氨酯泡沫体,和制备这种泡沫体的方法 |
JP5215897B2 (ja) * | 2009-02-06 | 2013-06-19 | 日本ビー・ケミカル株式会社 | 塗膜形成方法 |
JP4807604B2 (ja) * | 2009-03-23 | 2011-11-02 | Dic株式会社 | 保護粘着フィルム、スクリーンパネル、及び携帯電子端末 |
WO2011046243A1 (ko) * | 2009-10-16 | 2011-04-21 | 주식회사 포스코 | 방사선경화성 수지 조성물 및 이를 포함하는 내지문성 수지 조성물 |
US8372330B2 (en) * | 2009-10-19 | 2013-02-12 | Global Filtration Systems | Resin solidification substrate and assembly |
WO2011075553A1 (en) * | 2009-12-17 | 2011-06-23 | Dsm Ip Assets, B.V. | Liquid radiation curable resins for additive fabrication comprising a triaryl sulfonium borate cationic photoinitiator |
US8580887B2 (en) * | 2010-07-30 | 2013-11-12 | Basf Se | High-functionality polyisocyanates containing urethane groups |
US9157007B2 (en) * | 2011-03-09 | 2015-10-13 | 3D Systems, Incorporated | Build material and applications thereof |
CN102504174A (zh) * | 2011-12-19 | 2012-06-20 | 烟台德邦科技有限公司 | 一种聚氨酯丙烯酸酯及其制备方法以及应用 |
EP2794702B1 (de) * | 2011-12-22 | 2015-12-16 | Covestro Deutschland AG | Wässrige polyacrylat-copolymer-dispersionen mit hohen oh-gruppe-gehalt |
RU2014136188A (ru) * | 2012-02-08 | 2016-03-27 | Байер Интеллектчуал Проперти Гмбх | Способ изготовления твердой полиуретан-полиизоциануратной пены |
EP2847246B1 (de) | 2012-05-08 | 2016-04-20 | Basf Se | Herstellung von polyisocyanaten mit isocyanuratgruppen und verwendung davon |
CN102675590B (zh) * | 2012-05-25 | 2014-04-02 | 深圳职业技术学院 | 一种含脂环族环氧和双键的双重固化树脂的制备方法及应用 |
US9982146B2 (en) * | 2012-06-18 | 2018-05-29 | Ppg Industries Ohio, Inc. | Dual-cure compositions useful for coating metal substrates and processes using the compositions |
CN102977335B (zh) * | 2012-11-30 | 2015-04-22 | 深圳职业技术学院 | 一种以环氧氯丙烷为原料制备含光-热双重固化基团树脂的方法 |
CN105246953B (zh) * | 2013-02-08 | 2018-09-21 | 科思创德国股份有限公司 | 使用硬涂层的塑料基材的改进的最大加工温度 |
JP5633770B1 (ja) * | 2013-03-27 | 2014-12-03 | Dic株式会社 | 活性エネルギー線硬化性組成物、その硬化塗膜、及び該硬化塗膜を有する物品 |
EP3039048B1 (de) * | 2013-08-26 | 2018-10-24 | Basf Se | Strahlungshärtbare wasserdispergierbare polyurethan(meth)acrylate |
KR101814305B1 (ko) * | 2013-10-21 | 2018-01-02 | 미쯔이가가꾸가부시끼가이샤 | 광학 재료용 중합성 조성물 및 광학 재료 |
ES2651140T3 (es) | 2013-12-10 | 2018-01-24 | Covestro Deutschland Ag | Poliisocianatos con grupos iminooxadiacina diona |
CN104974502B (zh) | 2014-04-10 | 2019-12-27 | 科思创德国股份有限公司 | 聚氨酯复合材料及其制备方法 |
JP2016002683A (ja) | 2014-06-16 | 2016-01-12 | コニカミノルタ株式会社 | 3d造形物の製造方法、3d造形用光硬化性組成物および3d造形用インクセット |
EP2993195A1 (de) * | 2014-09-05 | 2016-03-09 | Huntsman International Llc | Verfahren zur Verbesserung der Frakturbeständigkeit von Polyisocyanurat mit Reaktionsprodukten |
CN105778005B (zh) | 2014-12-01 | 2020-04-28 | 科思创德国股份有限公司 | 可自由基聚合的聚氨酯组合物 |
JP2016135477A (ja) | 2015-01-20 | 2016-07-28 | 関西ペイント株式会社 | 基材の被膜形成方法 |
GB201501965D0 (en) * | 2015-02-05 | 2015-03-25 | Lumina Adhesives Ab | Polyurethane based switchable adhesives |
JP6381474B2 (ja) * | 2015-03-31 | 2018-08-29 | 三井化学株式会社 | 硬化性ポリウレタン樹脂組成物および硬化物 |
FR3035109B1 (fr) * | 2015-04-20 | 2017-04-28 | Arkema France | Urethanes aminoacrylate-acrylates de haute fonctionnalite derives de l'addition d'un aminoalcool a amine secondaire sur un acrylate multifonctionnel. |
KR20170139022A (ko) | 2015-04-21 | 2017-12-18 | 코베스트로 도이칠란트 아게 | 단열성 조건 하에 제조된 폴리이소시아누레이트 중합체를 기재로 하는 고형물 |
WO2016170059A1 (en) | 2015-04-21 | 2016-10-27 | Covestro Deutschland Ag | Polyisocyanurate polymers and process for the production of polyisocyanurate polymers |
WO2016170061A1 (en) | 2015-04-21 | 2016-10-27 | Covestro Deutschland Ag | Polyisocyanurate plastics having high thermal stability |
CN104830222B (zh) * | 2015-04-28 | 2017-04-12 | 中科院广州化学有限公司南雄材料生产基地 | 一种可双重固化的低表面能聚氨酯涂料及其制备方法 |
CA3035201A1 (en) | 2016-09-20 | 2018-03-29 | Covestro Deutschland Ag | Anisotropic composite materials based on polyisocyanates |
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US20190337224A1 (en) | 2019-11-07 |
WO2018087395A1 (de) | 2018-05-17 |
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EP3538585A1 (de) | 2019-09-18 |
US10449714B2 (en) | 2019-10-22 |
CN109923143A (zh) | 2019-06-21 |
US20190367665A1 (en) | 2019-12-05 |
CN109963890A (zh) | 2019-07-02 |
US11590692B2 (en) | 2023-02-28 |
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US20200190245A1 (en) | 2020-06-18 |
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US11613072B2 (en) | 2023-03-28 |
US20190367666A1 (en) | 2019-12-05 |
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US20180133953A1 (en) | 2018-05-17 |
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