JP2007515460A - アルコキシシラン官能基を有するビウレット及びイソシアネートの合成、それらを含む配合物及びそれらの利用 - Google Patents
アルコキシシラン官能基を有するビウレット及びイソシアネートの合成、それらを含む配合物及びそれらの利用 Download PDFInfo
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- JP2007515460A JP2007515460A JP2006546229A JP2006546229A JP2007515460A JP 2007515460 A JP2007515460 A JP 2007515460A JP 2006546229 A JP2006546229 A JP 2006546229A JP 2006546229 A JP2006546229 A JP 2006546229A JP 2007515460 A JP2007515460 A JP 2007515460A
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- Prior art keywords
- isocyanate
- advantageously
- units
- functional groups
- biuret
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims abstract description 124
- 125000000524 functional group Chemical group 0.000 title claims abstract description 63
- 239000012948 isocyanate Substances 0.000 title claims description 67
- 150000002513 isocyanates Chemical class 0.000 title claims description 48
- 230000015572 biosynthetic process Effects 0.000 title description 16
- 238000003786 synthesis reaction Methods 0.000 title description 8
- 238000009472 formulation Methods 0.000 title description 5
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims abstract description 89
- 150000001875 compounds Chemical class 0.000 claims abstract description 86
- 238000000034 method Methods 0.000 claims abstract description 39
- 239000005056 polyisocyanate Substances 0.000 claims abstract description 25
- 229920001228 polyisocyanate Polymers 0.000 claims abstract description 25
- OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical compound NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 claims description 67
- 239000000178 monomer Substances 0.000 claims description 50
- -1 uretidinedione Chemical compound 0.000 claims description 42
- 125000001931 aliphatic group Chemical group 0.000 claims description 27
- 150000001412 amines Chemical group 0.000 claims description 19
- 125000003118 aryl group Chemical group 0.000 claims description 17
- 125000004432 carbon atom Chemical group C* 0.000 claims description 15
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 13
- 229910052710 silicon Inorganic materials 0.000 claims description 13
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 12
- 238000004519 manufacturing process Methods 0.000 claims description 11
- 239000010703 silicon Substances 0.000 claims description 11
- 230000008569 process Effects 0.000 claims description 10
- 125000005842 heteroatom Chemical group 0.000 claims description 9
- 125000002947 alkylene group Chemical group 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 5
- AVWRKZWQTYIKIY-UHFFFAOYSA-N urea-1-carboxylic acid Chemical compound NC(=O)NC(O)=O AVWRKZWQTYIKIY-UHFFFAOYSA-N 0.000 claims description 5
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- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- RADWEERUPCRDRI-UHFFFAOYSA-N 4-amino-1h-1,3-diazet-2-one Chemical group N=C1NC(=O)N1 RADWEERUPCRDRI-UHFFFAOYSA-N 0.000 claims description 2
- YSKUZVBSHIWEFK-UHFFFAOYSA-N ammelide Chemical compound NC1=NC(O)=NC(O)=N1 YSKUZVBSHIWEFK-UHFFFAOYSA-N 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
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- 150000001787 chalcogens Chemical class 0.000 claims description 2
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- 150000001343 alkyl silanes Chemical group 0.000 claims 1
- WPRDEDGZJLTOFJ-UHFFFAOYSA-N oxadiazin-4-imine Chemical compound N=C1C=CON=N1 WPRDEDGZJLTOFJ-UHFFFAOYSA-N 0.000 claims 1
- 238000000576 coating method Methods 0.000 abstract description 8
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- 125000004427 diamine group Chemical group 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 description 45
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 41
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 39
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 29
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- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 14
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- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 13
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- 239000000047 product Substances 0.000 description 13
- SJECZPVISLOESU-UHFFFAOYSA-N 3-trimethoxysilylpropan-1-amine Chemical compound CO[Si](OC)(OC)CCCN SJECZPVISLOESU-UHFFFAOYSA-N 0.000 description 12
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- 125000002723 alicyclic group Chemical group 0.000 description 9
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- 238000004821 distillation Methods 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 239000003960 organic solvent Substances 0.000 description 7
- 150000003335 secondary amines Chemical group 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 125000005442 diisocyanate group Chemical group 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- AYLRODJJLADBOB-QMMMGPOBSA-N methyl (2s)-2,6-diisocyanatohexanoate Chemical compound COC(=O)[C@@H](N=C=O)CCCCN=C=O AYLRODJJLADBOB-QMMMGPOBSA-N 0.000 description 6
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- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 4
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- 239000002253 acid Substances 0.000 description 4
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 4
- 238000006384 oligomerization reaction Methods 0.000 description 4
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 239000010409 thin film Substances 0.000 description 4
- 231100000331 toxic Toxicity 0.000 description 4
- 230000002588 toxic effect Effects 0.000 description 4
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 3
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- 240000005428 Pistacia lentiscus Species 0.000 description 3
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- 238000009833 condensation Methods 0.000 description 3
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- 150000002009 diols Chemical class 0.000 description 3
- 238000005227 gel permeation chromatography Methods 0.000 description 3
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 3
- 239000012038 nucleophile Substances 0.000 description 3
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- QXRRAZIZHCWBQY-UHFFFAOYSA-N 1,1-bis(isocyanatomethyl)cyclohexane Chemical compound O=C=NCC1(CN=C=O)CCCCC1 QXRRAZIZHCWBQY-UHFFFAOYSA-N 0.000 description 2
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 2
- QFGCFKJIPBRJGM-UHFFFAOYSA-N 12-[(2-methylpropan-2-yl)oxy]-12-oxododecanoic acid Chemical compound CC(C)(C)OC(=O)CCCCCCCCCCC(O)=O QFGCFKJIPBRJGM-UHFFFAOYSA-N 0.000 description 2
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- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 1
- QLMCMYJQWTUURP-UHFFFAOYSA-N [dimethoxy(propyl)silyl]oxymethylurea Chemical compound CCC[Si](OC)(OC)OCNC(N)=O QLMCMYJQWTUURP-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- 150000001241 acetals Chemical class 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000002318 adhesion promoter Substances 0.000 description 1
- 150000001334 alicyclic compounds Chemical class 0.000 description 1
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 1
- 150000001414 amino alcohols Chemical class 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 125000000732 arylene group Chemical group 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- JGCWKVKYRNXTMD-UHFFFAOYSA-N bicyclo[2.2.1]heptane;isocyanic acid Chemical compound N=C=O.N=C=O.C1CC2CCC1C2 JGCWKVKYRNXTMD-UHFFFAOYSA-N 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 239000004567 concrete Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- PDXRQENMIVHKPI-UHFFFAOYSA-N cyclohexane-1,1-diol Chemical compound OC1(O)CCCCC1 PDXRQENMIVHKPI-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 238000001514 detection method Methods 0.000 description 1
- 239000012975 dibutyltin dilaurate Substances 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- JXCHMDATRWUOAP-UHFFFAOYSA-N diisocyanatomethylbenzene Chemical compound O=C=NC(N=C=O)C1=CC=CC=C1 JXCHMDATRWUOAP-UHFFFAOYSA-N 0.000 description 1
- 239000000806 elastomer Substances 0.000 description 1
- 239000012156 elution solvent Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002170 ethers Chemical group 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000007306 functionalization reaction Methods 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 description 1
- 239000008240 homogeneous mixture Substances 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- KDZAVFKRKQMGQY-UHFFFAOYSA-N imidazolidine;triethoxy(propyl)silane Chemical compound C1CNCN1.CCC[Si](OCC)(OCC)OCC KDZAVFKRKQMGQY-UHFFFAOYSA-N 0.000 description 1
- VVIKDFVENYHCQW-UHFFFAOYSA-N imidazolidine;trimethoxy(propyl)silane Chemical compound C1CNCN1.CCC[Si](OC)(OC)OC VVIKDFVENYHCQW-UHFFFAOYSA-N 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 150000002466 imines Chemical class 0.000 description 1
- 125000001841 imino group Chemical group [H]N=* 0.000 description 1
- ULNRRNBMNIIOJK-UHFFFAOYSA-N isocyanatourea Chemical compound NC(=O)NN=C=O ULNRRNBMNIIOJK-UHFFFAOYSA-N 0.000 description 1
- VKSCZTWQDPUHIK-UHFFFAOYSA-N isocyanic acid;trimethoxy(propyl)silane Chemical compound N=C=O.CCC[Si](OC)(OC)OC VKSCZTWQDPUHIK-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000003951 lactams Chemical class 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 150000002634 lipophilic molecules Chemical class 0.000 description 1
- 150000002668 lysine derivatives Chemical class 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 239000013521 mastic Substances 0.000 description 1
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 1
- CXHHBNMLPJOKQD-UHFFFAOYSA-M methyl carbonate Chemical compound COC([O-])=O CXHHBNMLPJOKQD-UHFFFAOYSA-M 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
- CQDGTJPVBWZJAZ-UHFFFAOYSA-N monoethyl carbonate Chemical compound CCOC(O)=O CQDGTJPVBWZJAZ-UHFFFAOYSA-N 0.000 description 1
- WHIVNJATOVLWBW-UHFFFAOYSA-N n-butan-2-ylidenehydroxylamine Chemical compound CCC(C)=NO WHIVNJATOVLWBW-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- HNHVTXYLRVGMHD-UHFFFAOYSA-N n-butyl isocyanate Chemical compound CCCCN=C=O HNHVTXYLRVGMHD-UHFFFAOYSA-N 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- UMRZSTCPUPJPOJ-KNVOCYPGSA-N norbornane Chemical compound C1C[C@H]2CC[C@@H]1C2 UMRZSTCPUPJPOJ-KNVOCYPGSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- HXSACZWWBYWLIS-UHFFFAOYSA-N oxadiazine-4,5,6-trione Chemical compound O=C1ON=NC(=O)C1=O HXSACZWWBYWLIS-UHFFFAOYSA-N 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 description 1
- 230000036961 partial effect Effects 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920000162 poly(ureaurethane) Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920002578 polythiourethane polymer Polymers 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 150000003217 pyrazoles Chemical class 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 239000006254 rheological additive Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- SCPYDCQAZCOKTP-UHFFFAOYSA-N silanol Chemical compound [SiH3]O SCPYDCQAZCOKTP-UHFFFAOYSA-N 0.000 description 1
- 125000005372 silanol group Chemical group 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- 238000002798 spectrophotometry method Methods 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- NBXZNTLFQLUFES-UHFFFAOYSA-N triethoxy(propyl)silane Chemical group CCC[Si](OCC)(OCC)OCC NBXZNTLFQLUFES-UHFFFAOYSA-N 0.000 description 1
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229940005605 valeric acid Drugs 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000012855 volatile organic compound Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
- C08L75/04—Polyurethanes
- C08L75/12—Polyurethanes from compounds containing nitrogen and active hydrogen, the nitrogen atom not being part of an isocyanate group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/10—Compounds having one or more C—Si linkages containing nitrogen having a Si-N linkage
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Polyurethanes Or Polyureas (AREA)
- Silicon Polymers (AREA)
- Paints Or Removers (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0315410A FR2864537B1 (fr) | 2003-12-24 | 2003-12-24 | Synthese de biurets et d'isocyanates a fonctions alcoxysilanes, formulations en contenant et leurs applications |
| PCT/FR2004/003261 WO2005070942A2 (fr) | 2003-12-24 | 2004-12-16 | Synthese de biurets et d'isocyanates a fonctions alcoxysilanes, formulations en contenant et leurs applications |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012115663A Division JP2012177133A (ja) | 2003-12-24 | 2012-05-21 | ポリイソシアネート組成物 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2007515460A true JP2007515460A (ja) | 2007-06-14 |
| JP2007515460A5 JP2007515460A5 (enExample) | 2009-05-28 |
Family
ID=34639616
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006546229A Pending JP2007515460A (ja) | 2003-12-24 | 2004-12-16 | アルコキシシラン官能基を有するビウレット及びイソシアネートの合成、それらを含む配合物及びそれらの利用 |
| JP2012115663A Pending JP2012177133A (ja) | 2003-12-24 | 2012-05-21 | ポリイソシアネート組成物 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012115663A Pending JP2012177133A (ja) | 2003-12-24 | 2012-05-21 | ポリイソシアネート組成物 |
Country Status (9)
| Country | Link |
|---|---|
| US (2) | US7875693B2 (enExample) |
| EP (1) | EP1711506B1 (enExample) |
| JP (2) | JP2007515460A (enExample) |
| KR (1) | KR100803890B1 (enExample) |
| CN (1) | CN100526320C (enExample) |
| ES (1) | ES2521618T3 (enExample) |
| FR (1) | FR2864537B1 (enExample) |
| PL (1) | PL1711506T3 (enExample) |
| WO (1) | WO2005070942A2 (enExample) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2340756B1 (es) * | 2010-01-18 | 2011-07-21 | Antonio Oliva Gurgui | Compuesto para la fabricacion de una marca al agua en un material laminar textil y composicion, material, procedimiento y uso correspondientes. |
| CA2898297C (en) * | 2013-03-14 | 2022-03-22 | The Government Of The United States Of America, As Represented By The Secretary Of The Navy | Single-component moisture-curable coatings based on n-substituted urea polymers with extended chains and terminal alkoxysilanes |
| US10190020B2 (en) | 2014-10-22 | 2019-01-29 | The United States Of America, As Represented By The Secretary Of The Navy | Siloxane-based coatings containing polymers with urea linkages and terminal alkoxysilanes |
| CA2960413C (en) * | 2014-10-22 | 2023-01-24 | Erick B. Iezzi | Two-component siloxane-based coatings containing polymers with urea linkages and terminal alkoxysilanes |
| EP3085720A1 (de) | 2015-04-21 | 2016-10-26 | Covestro Deutschland AG | Hydrophil modifizierter polyisocyanuratkunststoff und verfahren zu dessen herstellung |
| EP3162827B1 (de) * | 2015-10-29 | 2018-06-06 | Evonik Degussa GmbH | Beschichtungsmittel mit monoallophanaten auf basis von alkoxysilanalkylisocyanaten |
| JP6729320B2 (ja) * | 2016-11-21 | 2020-07-22 | 信越化学工業株式会社 | 有機ケイ素化合物を含む組成物並びにこれを含む塗料および接着剤 |
| CN110128624B (zh) * | 2018-02-08 | 2021-06-18 | 旭化成株式会社 | 多异氰酸酯组合物、涂料组合物、涂膜的制造方法及涂膜 |
| CN110003417A (zh) * | 2018-12-24 | 2019-07-12 | Yj企业有限公司 | 一种异氰酸酯预聚体及其制备方法和应用 |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS57128754A (en) * | 1981-02-03 | 1982-08-10 | Nippon Polyurethan Kogyo Kk | Primer composition and its preparation |
| JPS60226889A (ja) * | 1984-03-22 | 1985-11-12 | ワツカ−−ヒエミ−・ゲゼルシヤフト・ミツト・ベシユレンクテル・ハフツング | Ｓｉｏｃ結合された脂肪族基を有するＳｉｃ結合されたビウレツト基を含有するケイ素化合物、その製法およびポリウレタンおよびラツカ−の製法 |
| JP2003252949A (ja) * | 2001-12-27 | 2003-09-10 | Yokohama Rubber Co Ltd:The | ポリウレタン組成物 |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3361783A (en) * | 1962-11-16 | 1968-01-02 | Monsanto Co | Silylureas |
| US4143060A (en) * | 1971-11-06 | 1979-03-06 | Bayer Aktiengesellschaft | Process for the preparation of silyl substituted urea derivatives |
| US3933756A (en) * | 1972-08-05 | 1976-01-20 | Bayer Aktiengesellschaft | Process of preparation of synthetic resins by reacting a cross-linked isocyanate polyaddition product with low molecular weight polyisocyanate followed by reaction with an amino alkyl silane |
| DE2243628A1 (de) * | 1972-09-06 | 1974-03-14 | Bayer Ag | Polymere mit alkoxysilyl-substituierten biuretgruppen und verfahren zu ihrer herstellung |
| DE3263070D1 (en) * | 1981-02-03 | 1985-05-23 | Rhone Poulenc Spec Chim | Process for obtaining compounds containing isocyanuric groups by catalytic cyclotrimerization of isocyanates by means of compounds having aminosilyl groups, isocyanurates obtained by elaborating the process |
| CA1204720A (en) * | 1982-09-30 | 1986-05-20 | Hajimu Kitahara | Packing materials for chromatographic use and a method for analysis of an enantiomer mixture using the same |
| JPH0784574B2 (ja) * | 1986-04-22 | 1995-09-13 | ナトコペイント株式会社 | 塗料組成物 |
| US5393910A (en) | 1993-10-20 | 1995-02-28 | Osi Specialties, Inc. | Process for making isocyanatoorganosilanes |
| US5574122A (en) * | 1995-09-29 | 1996-11-12 | Bayer Corporation | Low surface energy polyisocyanates and their use in one- or two-component coating compositions |
| DE10013628A1 (de) * | 2000-03-18 | 2001-09-20 | Degussa | Stabile 1:1-Monoaddukte aus sekundären Aminoalkylalkoxysilanen und Diisocyanaten sowie ein Verfahren zu ihrer Herstellung |
| EP1373353B1 (fr) * | 2001-03-27 | 2010-03-10 | Rhodia Chimie | Composition polyisocyanate de faible viscosite possedant une fonctionnalite elevee et procede de preparation |
| DE10159803A1 (de) * | 2001-12-05 | 2003-07-03 | Degussa | Katalysatoren und Verfahren zur Herstellung von Isocyanuratgruppen enthaltenden Polyisocyanaten und deren Verwendung |
-
2003
- 2003-12-24 FR FR0315410A patent/FR2864537B1/fr not_active Expired - Lifetime
-
2004
- 2004-12-16 JP JP2006546229A patent/JP2007515460A/ja active Pending
- 2004-12-16 ES ES04816401.6T patent/ES2521618T3/es not_active Expired - Lifetime
- 2004-12-16 CN CNB2004800357070A patent/CN100526320C/zh not_active Expired - Lifetime
- 2004-12-16 EP EP04816401.6A patent/EP1711506B1/fr not_active Expired - Lifetime
- 2004-12-16 US US10/579,808 patent/US7875693B2/en not_active Expired - Lifetime
- 2004-12-16 KR KR1020067012661A patent/KR100803890B1/ko not_active Expired - Lifetime
- 2004-12-16 PL PL04816401T patent/PL1711506T3/pl unknown
- 2004-12-16 WO PCT/FR2004/003261 patent/WO2005070942A2/fr not_active Ceased
-
2010
- 2010-11-23 US US12/952,866 patent/US8173742B2/en not_active Expired - Lifetime
-
2012
- 2012-05-21 JP JP2012115663A patent/JP2012177133A/ja active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS57128754A (en) * | 1981-02-03 | 1982-08-10 | Nippon Polyurethan Kogyo Kk | Primer composition and its preparation |
| JPS60226889A (ja) * | 1984-03-22 | 1985-11-12 | ワツカ−−ヒエミ−・ゲゼルシヤフト・ミツト・ベシユレンクテル・ハフツング | Ｓｉｏｃ結合された脂肪族基を有するＳｉｃ結合されたビウレツト基を含有するケイ素化合物、その製法およびポリウレタンおよびラツカ−の製法 |
| JP2003252949A (ja) * | 2001-12-27 | 2003-09-10 | Yokohama Rubber Co Ltd:The | ポリウレタン組成物 |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2005070942A2 (fr) | 2005-08-04 |
| FR2864537A1 (fr) | 2005-07-01 |
| JP2012177133A (ja) | 2012-09-13 |
| US20070015895A1 (en) | 2007-01-18 |
| EP1711506B1 (fr) | 2014-10-08 |
| WO2005070942A3 (fr) | 2005-11-17 |
| US7875693B2 (en) | 2011-01-25 |
| PL1711506T3 (pl) | 2015-02-27 |
| EP1711506A2 (fr) | 2006-10-18 |
| US8173742B2 (en) | 2012-05-08 |
| ES2521618T3 (es) | 2014-11-13 |
| KR100803890B1 (ko) | 2008-02-14 |
| FR2864537B1 (fr) | 2006-02-17 |
| KR20060105028A (ko) | 2006-10-09 |
| US20110065957A1 (en) | 2011-03-17 |
| CN1890250A (zh) | 2007-01-03 |
| CN100526320C (zh) | 2009-08-12 |
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