CN1890250A - 具有烷氧基硅烷官能团的异氰酸酯和缩二脲的合成,含有它们的配制剂及其应用 - Google Patents
具有烷氧基硅烷官能团的异氰酸酯和缩二脲的合成,含有它们的配制剂及其应用 Download PDFInfo
- Publication number
- CN1890250A CN1890250A CNA2004800357070A CN200480035707A CN1890250A CN 1890250 A CN1890250 A CN 1890250A CN A2004800357070 A CNA2004800357070 A CN A2004800357070A CN 200480035707 A CN200480035707 A CN 200480035707A CN 1890250 A CN1890250 A CN 1890250A
- Authority
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- China
- Prior art keywords
- functional group
- composition
- isocyanate
- biuret
- equals
- Prior art date
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- Granted
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- 239000000203 mixture Substances 0.000 title claims abstract description 132
- 239000012948 isocyanate Substances 0.000 title claims description 51
- 150000002513 isocyanates Chemical class 0.000 title claims description 9
- 230000015572 biosynthetic process Effects 0.000 title description 5
- 238000009472 formulation Methods 0.000 title description 2
- 238000003786 synthesis reaction Methods 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 95
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims abstract description 70
- 238000000034 method Methods 0.000 claims abstract description 31
- 239000005056 polyisocyanate Substances 0.000 claims abstract description 24
- 229920001228 polyisocyanate Polymers 0.000 claims abstract description 24
- OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical compound NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 claims description 106
- 125000001261 isocyanato group Chemical group *N=C=O 0.000 claims description 54
- -1 isocyanuric acid ester Chemical class 0.000 claims description 50
- 125000000524 functional group Chemical group 0.000 claims description 48
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 46
- 239000000178 monomer Substances 0.000 claims description 46
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 41
- 229910000077 silane Inorganic materials 0.000 claims description 35
- 229910052799 carbon Inorganic materials 0.000 claims description 32
- 125000001931 aliphatic group Chemical group 0.000 claims description 29
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 239000001257 hydrogen Substances 0.000 claims description 14
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Natural products OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 claims description 13
- AVWRKZWQTYIKIY-UHFFFAOYSA-N urea-1-carboxylic acid Chemical compound NC(=O)NC(O)=O AVWRKZWQTYIKIY-UHFFFAOYSA-N 0.000 claims description 12
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 11
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- 125000003277 amino group Chemical group 0.000 claims description 10
- 125000005842 heteroatom Chemical group 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 125000001118 alkylidene group Chemical group 0.000 claims description 7
- 125000004103 aminoalkyl group Chemical group 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
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 238000006884 silylation reaction Methods 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- PJMDLNIAGSYXLA-UHFFFAOYSA-N 6-iminooxadiazine-4,5-dione Chemical compound N=C1ON=NC(=O)C1=O PJMDLNIAGSYXLA-UHFFFAOYSA-N 0.000 claims description 3
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- 239000010703 silicon Substances 0.000 claims description 3
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- 125000001183 hydrocarbyl group Chemical group 0.000 claims 4
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- 125000004427 diamine group Chemical group 0.000 abstract 1
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 64
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 64
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 10
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- 239000000463 material Substances 0.000 description 7
- 239000003960 organic solvent Substances 0.000 description 7
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- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000011248 coating agent Substances 0.000 description 6
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- 238000004821 distillation 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
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
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- 238000002360 preparation method Methods 0.000 description 5
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
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- 230000009977 dual effect Effects 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 4
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- JFCQEDHGNNZCLN-UHFFFAOYSA-N glutaric acid Chemical compound OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 4
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- ICYIIEFSHYSYRV-UHFFFAOYSA-N methylcarbamoylcarbamate Chemical compound COC(=O)NC(N)=O ICYIIEFSHYSYRV-UHFFFAOYSA-N 0.000 description 4
- 229920000768 polyamine Polymers 0.000 description 4
- 230000037452 priming Effects 0.000 description 4
- 238000012207 quantitative assay Methods 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- OQURWGJAWSLGQG-UHFFFAOYSA-N 1-isocyanatopropane Chemical compound CCCN=C=O OQURWGJAWSLGQG-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
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
- 239000005864 Sulphur Substances 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- XLJMAIOERFSOGZ-UHFFFAOYSA-N anhydrous cyanic acid Natural products OC#N XLJMAIOERFSOGZ-UHFFFAOYSA-N 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 150000001354 dialkyl silanes Chemical group 0.000 description 3
- 230000032050 esterification Effects 0.000 description 3
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- 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
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 239000013521 mastic Substances 0.000 description 3
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- GTCAXTIRRLKXRU-UHFFFAOYSA-N methyl carbamate Chemical compound COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 description 3
- 230000000269 nucleophilic effect Effects 0.000 description 3
- 239000012434 nucleophilic reagent Substances 0.000 description 3
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- 150000003141 primary amines Chemical class 0.000 description 3
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- JHPBZFOKBAGZBL-UHFFFAOYSA-N (3-hydroxy-2,2,4-trimethylpentyl) 2-methylprop-2-enoate Chemical compound CC(C)C(O)C(C)(C)COC(=O)C(C)=C JHPBZFOKBAGZBL-UHFFFAOYSA-N 0.000 description 2
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
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- AFABGHUZZDYHJO-UHFFFAOYSA-N 2-Methylpentane Chemical compound CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 2
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 2
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- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000004567 concrete Substances 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000010276 construction Methods 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
- 238000006006 cyclotrimerization reaction Methods 0.000 description 1
- 238000011157 data evaluation Methods 0.000 description 1
- 238000005034 decoration Methods 0.000 description 1
- 239000012975 dibutyltin dilaurate Substances 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- KIQKWYUGPPFMBV-UHFFFAOYSA-N diisocyanatomethane Chemical class O=C=NCN=C=O KIQKWYUGPPFMBV-UHFFFAOYSA-N 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 238000010894 electron beam technology Methods 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- WUDNUHPRLBTKOJ-UHFFFAOYSA-N ethyl isocyanate Chemical compound CCN=C=O WUDNUHPRLBTKOJ-UHFFFAOYSA-N 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000007667 floating Methods 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 239000000665 guar gum Substances 0.000 description 1
- 229960002154 guar gum Drugs 0.000 description 1
- 235000010417 guar gum Nutrition 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229940051250 hexylene glycol Drugs 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 150000002466 imines Chemical class 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 230000008595 infiltration Effects 0.000 description 1
- 238000001764 infiltration Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 239000012035 limiting reagent Substances 0.000 description 1
- 150000002668 lysine derivatives Chemical class 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 1
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical group 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
- 239000011707 mineral Substances 0.000 description 1
- 238000012544 monitoring process Methods 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
- 150000002829 nitrogen Chemical class 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
- 229920001778 nylon Polymers 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
- 239000003921 oil Substances 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 230000007096 poisonous effect Effects 0.000 description 1
- 229920002647 polyamide 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
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 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
- 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
- 150000003254 radicals Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009467 reduction 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
- 229920002545 silicone oil Polymers 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 238000012916 structural analysis Methods 0.000 description 1
- SEEPANYCNGTZFQ-UHFFFAOYSA-N sulfadiazine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NC1=NC=CC=N1 SEEPANYCNGTZFQ-UHFFFAOYSA-N 0.000 description 1
- 125000004646 sulfenyl group Chemical group S(*)* 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 150000003573 thiols Chemical group 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 230000001131 transforming effect Effects 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical compound CO[SiH](OC)OC YUYCVXFAYWRXLS-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
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000012855 volatile organic compound Substances 0.000 description 1
- 238000010792 warming Methods 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
- C07F7/10—Compounds having one or more C—Si linkages containing nitrogen having a Si-N linkage
-
- 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
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)
Abstract
Description
单元 | 单元摩尔数 | 单元wt% |
HDI单元总量 | 100 | 74.4 |
其氨基甲酸酯 | 1.3 | 1.4 |
其脲基甲酸酯 | 0.3 | 0.5 |
(EtO)3Si(CH2)3-N-单元 | 26 | 23.6 |
单元 | 化学位移 | % |
HDI/(EtO)3Si(CH2)3-N-混合缩二脲 | 7.5ppm | 49 |
真HDI缩二脲 | 7.0ppm | 39 |
脲 | 6.7ppm | 12 |
单元 | 单元摩尔数 | 单元wt% |
HDI单元总量 | 100 | 70.2 |
其氨基甲酸酯 | 4.2 | 4 |
其脲基甲酸酯 | 0.7 | 1.2 |
(EtO)3Si(CH2)3-N-单元 | 28.7 | 24.6 |
单元 | 化学位移 | % |
HDI/(EtO)3Si(CH2)3-N-混合缩二脲 | 7.5ppm | 59 |
真HDI缩二脲 | 7.0ppm | 30 |
脲 | 6.7ppm | 11 |
单元 | 单元摩尔数 | 单元wt% |
HDI单元总量 | 100 | 70.5 |
其HDI和甲基单氨基甲酸酯 | 2.7 | 2.2 |
其HDI和甲基脲基甲酸酯 | 0.6 | 0.9 |
(EtO)3Si(CH2)3-N-单元 | 29.7 | 25.5 |
单元 | 化学位移 | % |
HDI/(EtO)3Si(CH2)3-N-混合缩二脲 | 7.5ppm | 63 |
真HDI缩二脲 | 7.0ppm | 28 |
脲 | 6.7ppm | 9 |
物质 | wt% |
HDI单体和NCO-丙基三甲氧基硅烷 | 0.2 |
HDI和甲基单氨基甲酸酯 | 0.4 |
真HDI二聚物 | 1 |
HDI和甲基单脲基甲酸酯 | 0.6 |
真2HDI/1(EtO)3Si(CH2)3-NH-混合缩二脲 | 37.4 |
HDI-真2HDI/1(EtO)3Si(CH2)3-NH-混合缩二脲二聚物 | 1.8 |
混合(3HDI-2(EtO)3Si(CH2)3-NH-)双缩二脲 | 23.2 |
混合(4HDI-3(EtO)3Si(CH2)3-NH-)三缩二脲+真HDI缩二脲序列 | 16 |
混合(4HDI-3(EtO)3Si(CH2)3-NH-)重缩二脲+真HDI缩二脲序列 | 19.4 |
02CMI146002基底 | |
HDI | <0.1 |
HDI和乙基氨基甲酸酯 | 0.3 |
真HDI二聚物(痕量氨基甲酸酯) | 0.5 |
混合缩二脲(痕量三聚体官能团) | 30.0 |
混合双缩二脲(痕量二聚物和三聚体官能团) | 24.1 |
混合三缩二脲(痕量二聚物和三聚体官能团) | 16.5 |
重产物(混合四缩二脲)(痕量二聚物和三聚体官能团) | 28.6 |
02CMI145902基底 | |
HDI | <0.1 |
HDI和乙基氨基甲酸酯 | 0.3 |
真HDI二聚物 | 1.2 |
混合缩二脲(痕量三聚体官能团) | 38.4 |
混合双缩二脲(痕量二聚物和三聚体官能团) | 27.0 |
混合三缩二脲(痕量二聚物和三聚体官能团) | 14.9 |
重产物(混合四缩二脲)(痕量二聚物和三聚体官能团) | 18.2 |
物质 | wt% |
HDI单体和NCO-丙基三甲氧基硅烷 | 0.2 |
HDI和甲基单氨基甲酸酯 | 0.4 |
异氰酸丙基酯基三烷氧基硅烷和甲基单氨基甲酸酯 | 0.3 |
真HDI二聚物 | 1.8 |
HDI和甲基单脲基甲酸酯 | 2 |
真2HDI/1(EtO)3Si(CH2)3-NH-混合缩二脲和HDI的真异氰脲酸酯三聚体和HDI和异氰酸丙酯基三烷氧基硅烷的真异氰脲酸酯三聚体的混合物 | 32.3 |
HDI-真2HDI/1(EtO)3Si(CH2)3-NH-混合缩二脲二聚物 | 3.7 |
混合(3HDI-2(EtO)3Si(CH2)3-NH-)双缩二脲和混合(3HDI-2(EtO)3Si(CH2)3-NH-)缩二脲-并包含异氰脲酸酯和二聚物单元 | 19.3 |
重产物,由混合(4HDI-3(EtO)3Si(CH2)3-NH-)缩二脲和真HDI缩二脲序列组成,并包含异氰脲酸酯、二聚物、氨基甲酸酯和脲基甲酸酯单元* | 40 |
单元 | 单元摩尔数 | 单元wt% |
HDI单元总量 | 100 | 70.2 |
其HDI和甲基单氨基甲酸酯 | 4.5 | 3.7 |
其HDI和甲基脲基甲酸酯 | 2.9 | 4.5 |
其HDI异氰脲酸酯单元 | 8.4 | 5.9 |
(EtO)3Si(CH2)3-N-单元 | 16.8 | 14.4 |
由丁醇得到的单元总量(氨基甲酸酯、脲基甲酸酯) | 3.6 | 1.1 |
单元 | 化学位移 | % |
HDI/(EtO)3Si(CH2)3-N-混合缩二脲 | 7.5ppm | 39 |
真HDI缩二脲 | 7.0ppm | 50 |
脲 | 6.7ppm | 11 |
Claims (19)
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 |
FR0315410 | 2003-12-24 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN1890250A true CN1890250A (zh) | 2007-01-03 |
CN100526320C CN100526320C (zh) | 2009-08-12 |
Family
ID=34639616
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CNB2004800357070A Active CN100526320C (zh) | 2003-12-24 | 2004-12-16 | 具有烷氧基硅烷官能团的异氰酸酯和缩二脲的合成,含有它们的配制剂及其应用 |
Country Status (9)
Country | Link |
---|---|
US (2) | US7875693B2 (zh) |
EP (1) | EP1711506B1 (zh) |
JP (2) | JP2007515460A (zh) |
KR (1) | KR100803890B1 (zh) |
CN (1) | CN100526320C (zh) |
ES (1) | ES2521618T3 (zh) |
FR (1) | FR2864537B1 (zh) |
PL (1) | PL1711506T3 (zh) |
WO (1) | WO2005070942A2 (zh) |
Cited By (1)
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CN108137777A (zh) * | 2015-10-29 | 2018-06-08 | 赢创德固赛有限公司 | 包含基于烷氧基硅烷烷基异氰酸酯的单脲基甲酸酯的涂料 |
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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. |
ES2655448T3 (es) * | 2013-03-14 | 2018-02-20 | The Government Of The United States Of America, As Represented By The Secretary Of The Navy | Revestimientos de componente único curable con humedad a base de polímeros de urea N-sustituidos con cadenas extendidas y alcoxisilanos terminales |
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 |
AU2015337050B2 (en) | 2014-10-22 | 2019-10-10 | The Government Of The United States Of America, As Represented By The Secretary Of The Navy | Two-component siloxane-based coatings containing polymers with urea linkages and terminal alkoxysilanes |
EP3085719A1 (de) | 2015-04-21 | 2016-10-26 | Covestro Deutschland AG | Hydrophob modifizierter polyisocyanuratkunststoff und verfahren zu dessen herstellung |
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 |
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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 |
YU43254B (en) * | 1981-02-03 | 1989-06-30 | Rhone Poulenc Spec Chim | Process for obtaining polyizocianburate by catalytic cyclotrimerisation of izocianate |
JPS57128754A (en) * | 1981-02-03 | 1982-08-10 | Nippon Polyurethan Kogyo Kk | Primer composition and its preparation |
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 |
DE3410582A1 (de) * | 1984-03-22 | 1985-09-26 | Wacker-Chemie GmbH, 8000 München | Sic-gebundene biuretgruppen enthaltende siliciumverbindungen, verfahren zu ihrer herstellung und verwendung solcher organosiliciumverbindungen |
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 |
DE60235615D1 (de) * | 2001-03-27 | 2010-04-22 | Rhodia Chimie Sa | Niederviskose polyisocyanatzusammensetzung mit hoher funktionalität und herstellungsverfahren dafür |
DE10159803A1 (de) * | 2001-12-05 | 2003-07-03 | Degussa | Katalysatoren und Verfahren zur Herstellung von Isocyanuratgruppen enthaltenden Polyisocyanaten und deren Verwendung |
JP4053415B2 (ja) * | 2001-12-27 | 2008-02-27 | 横浜ゴム株式会社 | ポリウレタン組成物 |
-
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 active Active
- 2004-12-16 CN CNB2004800357070A patent/CN100526320C/zh active Active
- 2004-12-16 PL PL04816401T patent/PL1711506T3/pl unknown
- 2004-12-16 WO PCT/FR2004/003261 patent/WO2005070942A2/fr active Application Filing
- 2004-12-16 US US10/579,808 patent/US7875693B2/en active Active
- 2004-12-16 KR KR1020067012661A patent/KR100803890B1/ko active IP Right Grant
- 2004-12-16 EP EP04816401.6A patent/EP1711506B1/fr active Active
-
2010
- 2010-11-23 US US12/952,866 patent/US8173742B2/en active Active
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2012
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CN108137777A (zh) * | 2015-10-29 | 2018-06-08 | 赢创德固赛有限公司 | 包含基于烷氧基硅烷烷基异氰酸酯的单脲基甲酸酯的涂料 |
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Publication number | Publication date |
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US20110065957A1 (en) | 2011-03-17 |
WO2005070942A3 (fr) | 2005-11-17 |
EP1711506A2 (fr) | 2006-10-18 |
WO2005070942A2 (fr) | 2005-08-04 |
KR100803890B1 (ko) | 2008-02-14 |
CN100526320C (zh) | 2009-08-12 |
US20070015895A1 (en) | 2007-01-18 |
EP1711506B1 (fr) | 2014-10-08 |
US7875693B2 (en) | 2011-01-25 |
JP2007515460A (ja) | 2007-06-14 |
KR20060105028A (ko) | 2006-10-09 |
JP2012177133A (ja) | 2012-09-13 |
US8173742B2 (en) | 2012-05-08 |
FR2864537A1 (fr) | 2005-07-01 |
ES2521618T3 (es) | 2014-11-13 |
FR2864537B1 (fr) | 2006-02-17 |
PL1711506T3 (pl) | 2015-02-27 |
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