CA2950651C - Fluoroalkyl silanes - Google Patents
Fluoroalkyl silanes Download PDFInfo
- Publication number
- CA2950651C CA2950651C CA2950651A CA2950651A CA2950651C CA 2950651 C CA2950651 C CA 2950651C CA 2950651 A CA2950651 A CA 2950651A CA 2950651 A CA2950651 A CA 2950651A CA 2950651 C CA2950651 C CA 2950651C
- Authority
- CA
- Canada
- Prior art keywords
- fluorosilane
- group
- fluoroalkyl
- represented
- silane
- 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.)
- Expired - Fee Related
Links
- -1 Fluoroalkyl silanes Chemical class 0.000 title abstract description 27
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims abstract description 19
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 18
- XPBBUZJBQWWFFJ-UHFFFAOYSA-N fluorosilane Chemical compound [SiH3]F XPBBUZJBQWWFFJ-UHFFFAOYSA-N 0.000 claims description 43
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 35
- 150000003512 tertiary amines Chemical class 0.000 claims description 16
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 10
- 125000000962 organic group Chemical group 0.000 claims description 9
- 239000005977 Ethylene Substances 0.000 claims description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
- 239000001301 oxygen Substances 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 229910000077 silane Inorganic materials 0.000 abstract description 52
- 150000001412 amines Chemical class 0.000 abstract description 19
- 150000001875 compounds Chemical class 0.000 abstract description 7
- 125000001153 fluoro group Chemical group F* 0.000 abstract description 6
- 238000000576 coating method Methods 0.000 abstract description 4
- 230000002209 hydrophobic effect Effects 0.000 abstract description 4
- 125000005647 linker group Chemical group 0.000 abstract description 4
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 abstract description 3
- 230000007062 hydrolysis Effects 0.000 abstract description 3
- 238000006460 hydrolysis reaction Methods 0.000 abstract description 3
- 229910052710 silicon Inorganic materials 0.000 abstract description 3
- 125000003636 chemical group Chemical group 0.000 abstract description 2
- 239000011248 coating agent Substances 0.000 abstract description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract description 2
- 230000004048 modification Effects 0.000 abstract description 2
- 238000012986 modification Methods 0.000 abstract description 2
- 150000002894 organic compounds Chemical class 0.000 abstract description 2
- 239000012756 surface treatment agent Substances 0.000 abstract description 2
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 49
- 239000012948 isocyanate Substances 0.000 description 39
- 150000002513 isocyanates Chemical class 0.000 description 39
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 35
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 33
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 25
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 23
- 239000000203 mixture Substances 0.000 description 23
- FRGPKMWIYVTFIQ-UHFFFAOYSA-N triethoxy(3-isocyanatopropyl)silane Chemical compound CCO[Si](OCC)(OCC)CCCN=C=O FRGPKMWIYVTFIQ-UHFFFAOYSA-N 0.000 description 23
- 238000005160 1H NMR spectroscopy Methods 0.000 description 22
- 125000003709 fluoroalkyl group Chemical group 0.000 description 22
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 21
- 239000002904 solvent Substances 0.000 description 20
- BFIQGHWJERJARE-UHFFFAOYSA-N F[SiH3].NC(N)=O Chemical compound F[SiH3].NC(N)=O BFIQGHWJERJARE-UHFFFAOYSA-N 0.000 description 18
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 17
- 239000012975 dibutyltin dilaurate Substances 0.000 description 17
- 239000003921 oil Substances 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 15
- 125000004005 formimidoyl group Chemical group [H]\N=C(/[H])* 0.000 description 12
- RNLWPKPXXVJKNI-UHFFFAOYSA-N F[SiH3].C(N)(O)=O Chemical compound F[SiH3].C(N)(O)=O RNLWPKPXXVJKNI-UHFFFAOYSA-N 0.000 description 11
- DBTDEFJAFBUGPP-UHFFFAOYSA-N Methanethial Chemical compound S=C DBTDEFJAFBUGPP-UHFFFAOYSA-N 0.000 description 11
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 11
- 239000003054 catalyst Substances 0.000 description 11
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 11
- 238000003756 stirring Methods 0.000 description 11
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 10
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 10
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 9
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 8
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 8
- 101100073357 Streptomyces halstedii sch2 gene Proteins 0.000 description 8
- 125000000743 hydrocarbylene group Chemical group 0.000 description 8
- 239000001257 hydrogen Substances 0.000 description 8
- 229910052739 hydrogen Inorganic materials 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- 238000003786 synthesis reaction Methods 0.000 description 8
- 150000003573 thiols Chemical class 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 239000004202 carbamide Substances 0.000 description 7
- 150000002148 esters Chemical class 0.000 description 7
- QWCOSMBXZZJARK-UHFFFAOYSA-N fluorosilane thiourea Chemical compound F[SiH3].NC(N)=S QWCOSMBXZZJARK-UHFFFAOYSA-N 0.000 description 7
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 6
- 101150041968 CDC13 gene Proteins 0.000 description 6
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- 229910052731 fluorine Inorganic materials 0.000 description 6
- 150000002431 hydrogen Chemical class 0.000 description 6
- 150000002540 isothiocyanates Chemical class 0.000 description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 6
- VIONGDJUYAYOPU-UHFFFAOYSA-N 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctane-1-sulfonic acid Chemical compound OS(=O)(=O)CCC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F VIONGDJUYAYOPU-UHFFFAOYSA-N 0.000 description 5
- GTPHVVCYEWPQFE-UHFFFAOYSA-N 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctane-1-thiol Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)CCS GTPHVVCYEWPQFE-UHFFFAOYSA-N 0.000 description 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 5
- WYURNTSHIVDZCO-SVYQBANQSA-N oxolane-d8 Chemical compound [2H]C1([2H])OC([2H])([2H])C([2H])([2H])C1([2H])[2H] WYURNTSHIVDZCO-SVYQBANQSA-N 0.000 description 5
- 150000003568 thioethers Chemical class 0.000 description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- JBONTXQZKUTFRB-UHFFFAOYSA-N F[SiH3].C(CCC(=O)N)(=O)O Chemical compound F[SiH3].C(CCC(=O)N)(=O)O JBONTXQZKUTFRB-UHFFFAOYSA-N 0.000 description 4
- IANKFTPPKZJKNC-UHFFFAOYSA-N N-carbamoylformamide fluorosilane Chemical compound [SiH3]F.NC(=O)NC=O IANKFTPPKZJKNC-UHFFFAOYSA-N 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 239000012230 colorless oil Substances 0.000 description 4
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 150000003852 triazoles Chemical class 0.000 description 4
- ZSQMYBLYSFFHEK-UHFFFAOYSA-N 2-(3,3,5,5,6,6,7,7,8,8,8-undecafluorooctylsulfanyl)ethylazanium;chloride Chemical compound [Cl-].[NH3+]CCSCCC(F)(F)CC(F)(F)C(F)(F)C(F)(F)C(F)(F)F ZSQMYBLYSFFHEK-UHFFFAOYSA-N 0.000 description 3
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 3
- 230000020176 deacylation Effects 0.000 description 3
- 238000005947 deacylation reaction Methods 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- XGZNHFPFJRZBBT-UHFFFAOYSA-N ethanol;titanium Chemical compound [Ti].CCO.CCO.CCO.CCO XGZNHFPFJRZBBT-UHFFFAOYSA-N 0.000 description 3
- ZHNUHDYFZUAESO-UHFFFAOYSA-N formamide Substances NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 3
- HQBSTYMTGWCTLJ-UHFFFAOYSA-N isocyanic acid;triethoxy(3-isocyanatopropyl)silane Chemical compound N=C=O.CCO[Si](OCC)(OCC)CCCN=C=O HQBSTYMTGWCTLJ-UHFFFAOYSA-N 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 229940124530 sulfonamide Drugs 0.000 description 3
- 150000003456 sulfonamides Chemical class 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 229940086542 triethylamine Drugs 0.000 description 3
- 239000003039 volatile agent Substances 0.000 description 3
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 2
- BLIWNMRWJWOCKX-UHFFFAOYSA-N 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluoro-n-(2-hydroxyethyl)octane-1-sulfonamide Chemical compound OCCNS(=O)(=O)CCC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F BLIWNMRWJWOCKX-UHFFFAOYSA-N 0.000 description 2
- SQAFCSVGKMMETM-UHFFFAOYSA-N 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctane-1-sulfonamide Chemical compound NS(=O)(=O)CCC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F SQAFCSVGKMMETM-UHFFFAOYSA-N 0.000 description 2
- VPKQPPJQTZJZDB-UHFFFAOYSA-N 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl prop-2-enoate Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)CCOC(=O)C=C VPKQPPJQTZJZDB-UHFFFAOYSA-N 0.000 description 2
- SUAUZSMELAKHAC-UHFFFAOYSA-N 3,3,5,5,6,6,7,7,8,8,8-undecafluorooctane-1-thiol Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)CC(F)(F)CCS SUAUZSMELAKHAC-UHFFFAOYSA-N 0.000 description 2
- SJECZPVISLOESU-UHFFFAOYSA-N 3-trimethoxysilylpropan-1-amine Chemical compound CO[Si](OC)(OC)CCCN SJECZPVISLOESU-UHFFFAOYSA-N 0.000 description 2
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 238000006845 Michael addition reaction Methods 0.000 description 2
- 238000006957 Michael reaction Methods 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- UYMKPFRHYYNDTL-UHFFFAOYSA-N ethenamine Chemical compound NC=C UYMKPFRHYYNDTL-UHFFFAOYSA-N 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- ZQXSMRAEXCEDJD-UHFFFAOYSA-N n-ethenylformamide Chemical compound C=CNC=O ZQXSMRAEXCEDJD-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 229940014800 succinic anhydride Drugs 0.000 description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 description 1
- MRPSASLEFZGUCD-UHFFFAOYSA-N 1,1,1,2,2,3,3,4,4,6,6-undecafluoro-8-iodooctane Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)CC(F)(F)CCI MRPSASLEFZGUCD-UHFFFAOYSA-N 0.000 description 1
- WJVAPEMLIPHCJB-UHFFFAOYSA-N 1-n-methylpropane-1,2-diamine Chemical compound CNCC(C)N WJVAPEMLIPHCJB-UHFFFAOYSA-N 0.000 description 1
- JYWKEVKEKOTYEX-UHFFFAOYSA-N 2,6-dibromo-4-chloroiminocyclohexa-2,5-dien-1-one Chemical compound ClN=C1C=C(Br)C(=O)C(Br)=C1 JYWKEVKEKOTYEX-UHFFFAOYSA-N 0.000 description 1
- KHSFYUBENHDUNX-UHFFFAOYSA-N 2-(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctylsulfanyl)ethanamine Chemical compound NCCSCCC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F KHSFYUBENHDUNX-UHFFFAOYSA-N 0.000 description 1
- ZSSGQKVHSWOMGP-UHFFFAOYSA-N 3,3,4,4,7,7,8,8,11,11,12,12,12-tridecafluorododecan-1-ol Chemical compound OCCC(F)(F)C(F)(F)CCC(F)(F)C(F)(F)CCC(F)(F)C(F)(F)F ZSSGQKVHSWOMGP-UHFFFAOYSA-N 0.000 description 1
- BUDDZPPXEIFGAO-UHFFFAOYSA-N 3,3,4,4-tetrafluoro-4-(1,1,2,2,3,3,3-heptafluoropropoxy)butan-1-ol Chemical compound OCCC(F)(F)C(F)(F)OC(F)(F)C(F)(F)C(F)(F)F BUDDZPPXEIFGAO-UHFFFAOYSA-N 0.000 description 1
- NGXUXFLLVFJYTP-UHFFFAOYSA-N 3,3,4,4-tetrafluoro-4-(1,1,2,2,3,3,3-heptafluoropropoxy)butane-1-thiol Chemical compound FC(F)(F)C(F)(F)C(F)(F)OC(F)(F)C(F)(F)CCS NGXUXFLLVFJYTP-UHFFFAOYSA-N 0.000 description 1
- KOBXALIFCZVTOJ-UHFFFAOYSA-N 3,3,5,5,6,6,7,7,8,8,8-undecafluorooctan-1-ol Chemical compound OCCC(F)(F)CC(F)(F)C(F)(F)C(F)(F)C(F)(F)F KOBXALIFCZVTOJ-UHFFFAOYSA-N 0.000 description 1
- KLWJTFZEDMRNFZ-UHFFFAOYSA-N 3,3,5,5,6,6,7,7,8,8,8-undecafluorooctyl prop-2-enoate Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)CC(F)(F)CCOC(=O)C=C KLWJTFZEDMRNFZ-UHFFFAOYSA-N 0.000 description 1
- VMNVRPMXVRBLGV-UHFFFAOYSA-N 3,3,5,5,7,7,8,8,9,9,10,10,10-tridecafluorodecyl prop-2-enoate Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)CC(F)(F)CC(F)(F)CCOC(=O)C=C VMNVRPMXVRBLGV-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 1
- CZSIUELLPAWVKH-UHFFFAOYSA-N [3,3,4,4-tetrafluoro-4-(1,1,2,2,3,3,3-heptafluoropropoxy)butyl] prop-2-enoate Chemical compound FC(F)(F)C(F)(F)C(F)(F)OC(F)(F)C(F)(F)CCOC(=O)C=C CZSIUELLPAWVKH-UHFFFAOYSA-N 0.000 description 1
- ZRVIMDQCIXXVBA-UHFFFAOYSA-N [N].NC(N)=S Chemical compound [N].NC(N)=S ZRVIMDQCIXXVBA-UHFFFAOYSA-N 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 125000000732 arylene group Chemical group 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- AXTPGQHJFRSSQJ-UHFFFAOYSA-N dichloro-ethoxy-methylsilane Chemical compound CCO[Si](C)(Cl)Cl AXTPGQHJFRSSQJ-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- 229920000840 ethylene tetrafluoroethylene copolymer Polymers 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 150000004658 ketimines Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000005055 methyl trichlorosilane Substances 0.000 description 1
- JLUFWMXJHAVVNN-UHFFFAOYSA-N methyltrichlorosilane Chemical compound C[Si](Cl)(Cl)Cl JLUFWMXJHAVVNN-UHFFFAOYSA-N 0.000 description 1
- HGUJTFZRHBSOJZ-UHFFFAOYSA-N n-[2-(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctylsulfanyl)ethyl]formamide Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)CCSCCNC=O HGUJTFZRHBSOJZ-UHFFFAOYSA-N 0.000 description 1
- JOWMUPQBELRFRZ-UHFFFAOYSA-N n-carbamoylformamide Chemical compound NC(=O)NC=O JOWMUPQBELRFRZ-UHFFFAOYSA-N 0.000 description 1
- 235000011837 pasties Nutrition 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical compound [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- JDVPQXZIJDEHAN-UHFFFAOYSA-N succinamic acid Chemical compound NC(=O)CCC(O)=O JDVPQXZIJDEHAN-UHFFFAOYSA-N 0.000 description 1
- 150000003673 urethanes Chemical class 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
-
- 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
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si 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)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US544407P | 2007-12-04 | 2007-12-04 | |
| US61/005,444 | 2007-12-04 | ||
| US12/323,593 | 2008-11-26 | ||
| US12/323,593 US8058463B2 (en) | 2007-12-04 | 2008-11-26 | Fluorosilanes |
| CA2706614A CA2706614C (en) | 2007-12-04 | 2008-12-01 | Fluoroalkyl silanes |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2706614A Division CA2706614C (en) | 2007-12-04 | 2008-12-01 | Fluoroalkyl silanes |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2950651A1 CA2950651A1 (en) | 2009-06-11 |
| CA2950651C true CA2950651C (en) | 2018-08-28 |
Family
ID=40676432
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2950651A Expired - Fee Related CA2950651C (en) | 2007-12-04 | 2008-12-01 | Fluoroalkyl silanes |
| CA2706614A Expired - Fee Related CA2706614C (en) | 2007-12-04 | 2008-12-01 | Fluoroalkyl silanes |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2706614A Expired - Fee Related CA2706614C (en) | 2007-12-04 | 2008-12-01 | Fluoroalkyl silanes |
Country Status (9)
| Country | Link |
|---|---|
| US (3) | US8058463B2 (enExample) |
| EP (1) | EP2215098B1 (enExample) |
| JP (1) | JP5680966B2 (enExample) |
| KR (2) | KR101588470B1 (enExample) |
| CN (1) | CN101889018B (enExample) |
| AU (1) | AU2008334037B2 (enExample) |
| CA (2) | CA2950651C (enExample) |
| NZ (1) | NZ585454A (enExample) |
| WO (1) | WO2009073595A1 (enExample) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8058463B2 (en) * | 2007-12-04 | 2011-11-15 | E. I. Du Pont De Nemours And Compnay | Fluorosilanes |
| US8153834B2 (en) * | 2007-12-05 | 2012-04-10 | E.I. Dupont De Nemours And Company | Surface modified inorganic particles |
| US8258341B2 (en) * | 2009-07-10 | 2012-09-04 | E.I. Du Pont De Nemours And Company | Polyfluorosulfonamido amine and intermediate |
| JP2011105655A (ja) * | 2009-11-18 | 2011-06-02 | Institute Of Systems Information Technologies & Nanotechnologies | 化合物 |
| DE102010039704A1 (de) * | 2010-08-24 | 2012-03-01 | Wacker Chemie Ag | Emulsionen von Organopolysiloxane mit sauren und basischen Gruppen und deren Herstellung |
| JP6190572B2 (ja) * | 2011-06-24 | 2017-08-30 | 広栄化学工業株式会社 | トリアルコキシシリルアルキル基を有するオニウム塩 |
| KR101369381B1 (ko) * | 2011-11-04 | 2014-03-06 | 에스케이이노베이션 주식회사 | 함불소 화합물을 포함하는 저굴절 코팅 조성물, 이를 이용한 반사방지 필름, 이를 포함하는 편광판 및 표시장치 |
| WO2014163004A1 (ja) * | 2013-04-04 | 2014-10-09 | 旭硝子株式会社 | 含フッ素エーテル化合物、含フッ素エーテル組成物およびコーティング液、ならびに表面層を有する基材およびその製造方法 |
| WO2015113919A1 (de) * | 2014-01-31 | 2015-08-06 | Bayer Materialscience Ag | Silanmodifizierte formamide |
| JP6568087B2 (ja) * | 2014-01-31 | 2019-08-28 | コベストロ、ドイチュラント、アクチエンゲゼルシャフトＣｏｖｅｓｔｒｏ Ｄｅｕｔｓｃｈｌａｎｄ Ａｇ | シラン変性ホルムアミド |
| KR20160138993A (ko) | 2014-03-31 | 2016-12-06 | 미쓰비시 마테리알 가부시키가이샤 | 불소 함유 실란 화합물 |
| JP5731037B1 (ja) * | 2014-03-31 | 2015-06-10 | 三菱マテリアル株式会社 | 含フッ素シラン化合物 |
| US20160200953A1 (en) | 2014-04-18 | 2016-07-14 | Jason Constantinou | Methods and formulations for superhydrophic, self-cleaning, and icephobic polymer coatings and objects having coatings thereon |
| CN104292251B (zh) * | 2014-09-12 | 2017-02-15 | 苏州大学 | 一种防水剂、制备方法及其应用 |
| JP6319905B2 (ja) * | 2014-09-17 | 2018-05-09 | 三菱マテリアル株式会社 | 被膜形成用組成物及びその製造方法、並びに被膜 |
| WO2016176388A1 (en) | 2015-04-30 | 2016-11-03 | The Chemours Company Tt, Llc | Crosslinkable fluorinated inorganic oxide particle for architectural coatings |
| JP2017170629A (ja) * | 2016-03-18 | 2017-09-28 | 三菱マテリアル株式会社 | 被膜 |
| KR102339505B1 (ko) * | 2016-07-29 | 2021-12-16 | 다이킨 고교 가부시키가이샤 | 표면 처리제 및 해당 표면 처리제로 형성된 층을 포함하는 물품 |
| KR20200127351A (ko) * | 2019-05-02 | 2020-11-11 | 전남대학교산학협력단 | 초소수성을 갖는 나노입자 형성방법 |
| GB2623090A (en) | 2022-10-04 | 2024-04-10 | Sublino Ltd | Method of colouring |
| CN116903654B (zh) * | 2023-07-03 | 2025-07-22 | 南开大学 | 疏水改性剂及其制备方法、制备改性无机填料的方法 |
Family Cites Families (54)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1232959B (de) * | 1964-09-12 | 1967-01-26 | Walter Bloechl | Verfahren zur Herstellung eines aus waessriger Loesung anwendbaren Impraegniermittels |
| GB1140072A (en) | 1966-02-18 | 1969-01-15 | Ici Ltd | Fluorine-containing organosilicon compounds |
| US3420793A (en) * | 1967-03-16 | 1969-01-07 | Us Agriculture | Bis-(fluoroalkoxy)alkyl siloxanes |
| US3719698A (en) * | 1967-11-27 | 1973-03-06 | Stevens & Co Inc J P | Polyfluorinated esters of acids containing silicon and amino groups |
| FR2029262A5 (enExample) * | 1969-01-22 | 1970-10-16 | Ugine Kuhlmann | |
| FR2034142B1 (enExample) | 1969-02-11 | 1975-07-04 | Ugine Kuhlmann | |
| GB1267224A (enExample) | 1969-08-06 | 1972-03-15 | ||
| US3639156A (en) * | 1970-05-19 | 1972-02-01 | Us Agriculture | Siloxane polymers for soil-repellent and soil-release textile finishes |
| FR2097406A5 (enExample) * | 1970-07-06 | 1972-03-03 | Pechiney Saint Gobain | |
| US3646085A (en) * | 1970-09-24 | 1972-02-29 | Du Pont | Perfluoroalkyletheramidoalkyltrialkoxysilanes |
| US3666538A (en) * | 1970-10-12 | 1972-05-30 | Nalco Chemical Co | Process of rendering a solid material oil and water repellent |
| DE2107758A1 (de) * | 1971-02-18 | 1972-09-07 | Farbenfabriken Bayer Ag, 5090 Leverkusen | Perfluoralkansulfonamidomethylsiloxy 1-Verbindungen und ihre Herstellung |
| CH565736A5 (enExample) | 1972-03-16 | 1975-08-29 | Ciba Geigy Ag | |
| CH587297A5 (enExample) * | 1972-12-22 | 1977-04-29 | Ciba Geigy Ag | |
| US4070152A (en) * | 1976-01-12 | 1978-01-24 | Ciba-Geigy Corporation | Textile treating compositions for increasing water and oil repellency of textiles |
| US4171282A (en) * | 1977-12-07 | 1979-10-16 | Ciba-Geigy Corporation | Fluorinated nonionic surfactants |
| JPS60190727A (ja) * | 1984-03-09 | 1985-09-28 | Daikin Ind Ltd | 含フツ素有機シラン化合物およびその製法と用途 |
| US4645846A (en) | 1985-04-12 | 1987-02-24 | Scm Corporation | Silane compositions |
| JP2665961B2 (ja) | 1988-12-20 | 1997-10-22 | ナトコペイント株式会社 | 被膜形成方法 |
| EP0493747B1 (en) * | 1990-12-25 | 1996-07-10 | Matsushita Electric Industrial Co., Ltd. | Anti-contaminating adsorbed film and method of manufacturing the same |
| EP0629673B1 (en) | 1991-01-23 | 2002-05-02 | Matsushita Electric Industrial Co., Ltd. | Water- and oil-repelling adsorbed film |
| DE4233396A1 (de) * | 1992-10-05 | 1994-04-07 | Merck Patent Gmbh | Oberflächenmodifizierte Oxidpartikel und ihre Anwendung als Füll- und Modifizierungsmittel in Polymermaterialien |
| DE4329262A1 (de) * | 1993-08-31 | 1995-03-02 | Bayer Ag | Fluoratome enthaltende Alkoxysilanverbindungen |
| CA2161181A1 (en) | 1994-10-25 | 1996-04-26 | Frank Kropfgans | Process for the preparation of 3-halo- and -pseudohaloalkylsilane esters |
| JP3941146B2 (ja) | 1997-02-25 | 2007-07-04 | ダイキン工業株式会社 | 撥水撥油剤組成物 |
| FR2777456B1 (fr) | 1998-04-15 | 2001-04-27 | Oreal | Composition anhydre fluoree et produits cosmetiques de maquillage ou de soins la contenant |
| FR2777567B1 (fr) * | 1998-04-15 | 2000-06-23 | Oreal | Composes fluoro-silicones sous forme d'huile et leur utilisation en cosmetique |
| JP4411668B2 (ja) | 1998-08-13 | 2010-02-10 | 凸版印刷株式会社 | 防汚剤 |
| TW591097B (en) | 1998-12-10 | 2004-06-11 | Toray Industries | Optical articles and the preparation of optical articles |
| US6709504B2 (en) * | 2000-05-19 | 2004-03-23 | E. I. Du Pont De Nemours And Company | Emulsion and water-repellent composition |
| JP4126521B2 (ja) | 2000-08-04 | 2008-07-30 | 信越化学工業株式会社 | 被膜形成用組成物用フロロオルガノポリシロキサン樹脂の製造方法 |
| DE10051182A1 (de) | 2000-10-16 | 2002-05-02 | Nano X Gmbh | Nanopartikel mit hydrophoben und oleophoben Eigenschaften, deren Verarbeitung und Verwendung |
| EP1225188B1 (en) * | 2001-01-19 | 2007-03-28 | 3M Innovative Properties Company | Water soluble or water dispersible fluorochemical silanes for rendering substrates oil and water repellent. |
| EP1414831A1 (de) * | 2001-08-02 | 2004-05-06 | Clariant GmbH | Fluoralkylmodifizierte organosilane, verwendung in beschichtungszusammensetzungen |
| TW200408324A (en) * | 2002-09-19 | 2004-05-16 | Daikin Ind Ltd | Material using patterned surface as template and manufacturing method thereof |
| AU2003304346A1 (en) * | 2003-07-22 | 2005-02-04 | Canon Kabushiki Kaisha | Ink jet head and its manufacture method |
| EP1646504B1 (en) * | 2003-07-22 | 2010-04-21 | Canon Kabushiki Kaisha | Ink jet head and its manufacture method |
| US7652115B2 (en) * | 2003-09-08 | 2010-01-26 | 3M Innovative Properties Company | Fluorinated polyether isocyanate derived silane compositions |
| US7803894B2 (en) * | 2003-12-05 | 2010-09-28 | 3M Innovatie Properties Company | Coating compositions with perfluoropolyetherisocyanate derived silane and alkoxysilanes |
| US7321018B2 (en) * | 2003-12-23 | 2008-01-22 | 3M Innovative Properties Company | Compositions for aqueous delivery of fluorinated oligomeric silanes |
| KR100607716B1 (ko) | 2004-04-22 | 2006-08-01 | 한국화학연구원 | 불소계 지문방지제와 이의 제조방법 |
| US7495118B2 (en) * | 2004-12-30 | 2009-02-24 | 3M Innovative Properties Company | Compositions containing C4-swallow tail silanes |
| JP4712478B2 (ja) | 2005-02-10 | 2011-06-29 | 株式会社リコー | 画像読み取り装置および画像読み取り装置付き記録装置 |
| EP1717240B1 (de) * | 2005-04-29 | 2010-09-22 | Sika Technology AG | Organoalkoxysilane zur Verwendung in feuchtigkeitshärtenden Zusammensetzungen |
| JP5022584B2 (ja) | 2005-09-08 | 2012-09-12 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | フルオロカーボンシラン含有水性エマルジョン並びに水滴転落性および撥水撥油性の被覆物 |
| US20070066762A1 (en) | 2005-09-22 | 2007-03-22 | Acosta Erick J | Triazole-containing fluorinated polymers |
| NZ567495A (en) | 2005-10-26 | 2011-01-28 | Nanogate Ag | Compositions comprising the acid catalysed condensation product of a fluorosilane with an aminosilane |
| KR100669345B1 (ko) * | 2005-10-28 | 2007-01-16 | 삼성전자주식회사 | 비휘발성 메모리 장치 및 그 형성 방법 |
| US7473658B2 (en) * | 2006-11-13 | 2009-01-06 | E. I. Du Pont Nemours And Company | Partially fluorinated amino acid derivatives as gelling and surface active agents |
| US7745653B2 (en) * | 2007-03-08 | 2010-06-29 | 3M Innovative Properties Company | Fluorochemical compounds having pendent silyl groups |
| WO2009008380A1 (ja) * | 2007-07-06 | 2009-01-15 | Asahi Glass Company, Limited | 表面処理剤、物品、および新規含フッ素エーテル化合物 |
| US8058463B2 (en) * | 2007-12-04 | 2011-11-15 | E. I. Du Pont De Nemours And Compnay | Fluorosilanes |
| WO2009087981A1 (ja) * | 2008-01-11 | 2009-07-16 | Kri Inc. | 重合性化合物及びこの製造方法 |
| US8071010B2 (en) * | 2008-08-14 | 2011-12-06 | King Saud University | Process for producing concrete in hot weather |
-
2008
- 2008-11-26 US US12/323,593 patent/US8058463B2/en not_active Expired - Fee Related
- 2008-12-01 NZ NZ585454A patent/NZ585454A/en not_active IP Right Cessation
- 2008-12-01 EP EP08857672.3A patent/EP2215098B1/en not_active Not-in-force
- 2008-12-01 JP JP2010537004A patent/JP5680966B2/ja not_active Expired - Fee Related
- 2008-12-01 CA CA2950651A patent/CA2950651C/en not_active Expired - Fee Related
- 2008-12-01 KR KR1020107014617A patent/KR101588470B1/ko not_active Expired - Fee Related
- 2008-12-01 CN CN200880119435.0A patent/CN101889018B/zh not_active Expired - Fee Related
- 2008-12-01 AU AU2008334037A patent/AU2008334037B2/en not_active Ceased
- 2008-12-01 KR KR1020157034132A patent/KR20150140408A/ko not_active Ceased
- 2008-12-01 CA CA2706614A patent/CA2706614C/en not_active Expired - Fee Related
- 2008-12-01 WO PCT/US2008/085109 patent/WO2009073595A1/en not_active Ceased
-
2011
- 2011-09-23 US US13/242,434 patent/US8501952B2/en not_active Expired - Fee Related
- 2011-09-23 US US13/242,365 patent/US8420826B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| US8058463B2 (en) | 2011-11-15 |
| EP2215098A1 (en) | 2010-08-11 |
| HK1150610A1 (en) | 2012-01-06 |
| US8420826B2 (en) | 2013-04-16 |
| US20120022266A1 (en) | 2012-01-26 |
| JP2011505422A (ja) | 2011-02-24 |
| CA2950651A1 (en) | 2009-06-11 |
| AU2008334037A1 (en) | 2009-06-11 |
| WO2009073595A1 (en) | 2009-06-11 |
| US20090143598A1 (en) | 2009-06-04 |
| EP2215098B1 (en) | 2014-08-20 |
| AU2008334037B2 (en) | 2013-09-12 |
| CN101889018B (zh) | 2014-05-14 |
| CA2706614C (en) | 2017-08-22 |
| KR20100101625A (ko) | 2010-09-17 |
| CN101889018A (zh) | 2010-11-17 |
| KR101588470B1 (ko) | 2016-01-25 |
| CA2706614A1 (en) | 2009-06-11 |
| JP5680966B2 (ja) | 2015-03-04 |
| KR20150140408A (ko) | 2015-12-15 |
| NZ585454A (en) | 2012-05-25 |
| US20120022267A1 (en) | 2012-01-26 |
| US8501952B2 (en) | 2013-08-06 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA2950651C (en) | Fluoroalkyl silanes | |
| US8314264B2 (en) | Photopolymerizable functional radical-containing organosilicon compound and making method | |
| EP0757033A2 (en) | Vinyl carbonate and vinyl carbamate monomers for a contact lens material | |
| EP2289898B1 (en) | Melamine-functional organosilicon compound and making method | |
| JP5497659B2 (ja) | 硫黄含有フルオロアルキルアミンおよびイソシアナート | |
| JP2011505421A5 (enExample) | ||
| HK1150610B (en) | Fluoroalkyl silanes | |
| JP3594113B2 (ja) | 含フッ素アミド化合物 | |
| US6784306B2 (en) | Fluorinated organosilicon compounds | |
| JP6319122B2 (ja) | 含硫黄アミノオルガノキシシラン化合物及びその製造方法 | |
| US6140523A (en) | Organosilicon compounds and making method | |
| KR100649511B1 (ko) | 비스-실릴 3차 아민 | |
| KR950007920B1 (ko) | 신규 4-에톡시카보닐-1-메틸피라졸-5-설폰 카바메이트 유도체 및 그의 제조방법 | |
| US20230140949A1 (en) | Method for the synthesis of isocyanates | |
| JPS62149688A (ja) | クロロプロペニルジアルコキシシラン | |
| JP2007106889A (ja) | 含フッ素硬化性組成物 | |
| KR20140141483A (ko) | 실릴기로 보호된 질소 함유 환상 화합물 및 그의 제조 방법 | |
| EP1046646A1 (en) | Bis-silyl tertiary amines | |
| WO2006037869A3 (fr) | Composes fluorophosphonocinnamiques , synthese et applications dans le traitement des troubles causés par un stress oxydatif |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request |
Effective date: 20170505 |
|
| MKLA | Lapsed |
Effective date: 20210831 |
|
| MKLA | Lapsed |
Effective date: 20191202 |