KR20150140408A - 플루오로알킬 실란 - Google Patents
플루오로알킬 실란 Download PDFInfo
- Publication number
- KR20150140408A KR20150140408A KR1020157034132A KR20157034132A KR20150140408A KR 20150140408 A KR20150140408 A KR 20150140408A KR 1020157034132 A KR1020157034132 A KR 1020157034132A KR 20157034132 A KR20157034132 A KR 20157034132A KR 20150140408 A KR20150140408 A KR 20150140408A
- Authority
- KR
- South Korea
- Prior art keywords
- group
- fluorosilane
- fluoroalkylsilanes
- 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.)
- Ceased
Links
- -1 Fluoroalkyl silanes Chemical class 0.000 title description 27
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims abstract description 18
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 11
- 125000001153 fluoro group Chemical group F* 0.000 claims abstract description 8
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 5
- XPBBUZJBQWWFFJ-UHFFFAOYSA-N fluorosilane Chemical compound [SiH3]F XPBBUZJBQWWFFJ-UHFFFAOYSA-N 0.000 claims description 37
- 125000000743 hydrocarbylene group Chemical group 0.000 claims description 24
- 229910052799 carbon Inorganic materials 0.000 claims description 14
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 125000000962 organic group Chemical group 0.000 claims description 9
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 6
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 5
- 239000005977 Ethylene Substances 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
- 150000002431 hydrogen Chemical class 0.000 claims description 5
- 239000001301 oxygen Substances 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 abstract description 17
- 150000001875 compounds Chemical class 0.000 abstract description 7
- 238000000576 coating method Methods 0.000 abstract description 6
- 230000004048 modification Effects 0.000 abstract description 4
- 238000012986 modification Methods 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
- 125000005647 linker group Chemical group 0.000 abstract description 3
- 125000003636 chemical group Chemical group 0.000 abstract description 2
- 239000011248 coating agent Substances 0.000 abstract description 2
- 230000002209 hydrophobic effect Effects 0.000 abstract description 2
- 125000002887 hydroxy group Chemical group [H]O* 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 44
- 229910000077 silane Inorganic materials 0.000 description 44
- 239000012948 isocyanate Substances 0.000 description 36
- 150000002513 isocyanates Chemical class 0.000 description 35
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 26
- 238000005481 NMR spectroscopy Methods 0.000 description 26
- FRGPKMWIYVTFIQ-UHFFFAOYSA-N triethoxy(3-isocyanatopropyl)silane Chemical compound CCO[Si](OCC)(OCC)CCCN=C=O FRGPKMWIYVTFIQ-UHFFFAOYSA-N 0.000 description 25
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 23
- 239000000203 mixture Substances 0.000 description 20
- 239000002904 solvent Substances 0.000 description 20
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 19
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 18
- 150000003512 tertiary amines Chemical class 0.000 description 18
- 125000003709 fluoroalkyl group Chemical group 0.000 description 16
- 239000003921 oil Substances 0.000 description 16
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 15
- 239000012975 dibutyltin dilaurate Substances 0.000 description 15
- 230000015572 biosynthetic process Effects 0.000 description 13
- 238000003786 synthesis reaction Methods 0.000 description 13
- RNLWPKPXXVJKNI-UHFFFAOYSA-N F[SiH3].C(N)(O)=O Chemical compound F[SiH3].C(N)(O)=O RNLWPKPXXVJKNI-UHFFFAOYSA-N 0.000 description 11
- BFIQGHWJERJARE-UHFFFAOYSA-N F[SiH3].NC(N)=O Chemical compound F[SiH3].NC(N)=O BFIQGHWJERJARE-UHFFFAOYSA-N 0.000 description 11
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 239000003054 catalyst Substances 0.000 description 9
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
- 150000003573 thiols Chemical class 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- 239000004202 carbamide Substances 0.000 description 8
- 150000002148 esters Chemical class 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- 150000003568 thioethers Chemical class 0.000 description 8
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 7
- OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 7
- 238000005160 1H NMR spectroscopy Methods 0.000 description 6
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 6
- 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 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 150000002540 isothiocyanates Chemical class 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 5
- 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 5
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=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
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 4
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 239000012230 colorless oil Substances 0.000 description 4
- 239000011737 fluorine Substances 0.000 description 4
- 150000004756 silanes Chemical class 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 4
- SJECZPVISLOESU-UHFFFAOYSA-N 3-trimethoxysilylpropan-1-amine Chemical compound CO[Si](OC)(OC)CCCN SJECZPVISLOESU-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 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
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 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 3
- JOWMUPQBELRFRZ-UHFFFAOYSA-N n-carbamoylformamide Chemical compound NC(=O)NC=O JOWMUPQBELRFRZ-UHFFFAOYSA-N 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 239000003039 volatile agent Substances 0.000 description 3
- 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 2
- 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 2
- SMUQAHYSAIQWNW-UHFFFAOYSA-N 2-[3,3,4,4-tetrafluoro-4-(1,1,2,2,3,3,3-heptafluoropropoxy)butyl]sulfanylethanamine Chemical compound NCCSCCC(F)(F)C(F)(F)OC(F)(F)C(F)(F)C(F)(F)F SMUQAHYSAIQWNW-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
- 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
- 238000006845 Michael addition reaction Methods 0.000 description 2
- GZYPCIXZZAFVRD-UHFFFAOYSA-N N-[2-(3,3,5,5,6,6,7,7,8,8,8-undecafluorooctylsulfanyl)ethyl]formamide Chemical compound [H]N(C([H])=O)C([H])([H])C([H])([H])SC([H])([H])C([H])([H])C(F)(F)C([H])([H])C(F)(F)C(F)(F)C(F)(F)C(F)(F)F GZYPCIXZZAFVRD-UHFFFAOYSA-N 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
- 229920000840 ethylene tetrafluoroethylene copolymer Polymers 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N formamide Substances NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- FBAFATDZDUQKNH-UHFFFAOYSA-M iron chloride Chemical compound [Cl-].[Fe] FBAFATDZDUQKNH-UHFFFAOYSA-M 0.000 description 2
- 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 2
- 238000000034 method Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- ZQXSMRAEXCEDJD-UHFFFAOYSA-N n-ethenylformamide Chemical compound C=CNC=O ZQXSMRAEXCEDJD-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 229940124530 sulfonamide Drugs 0.000 description 2
- 150000003456 sulfonamides Chemical class 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
- 150000003852 triazoles Chemical class 0.000 description 2
- NFJJZDSLZRMSQT-UHFFFAOYSA-N 1,1,1,2,2,3,3,4,4,5,5,6,6-tridecafluoro-8-(2-isocyanatoethylsulfanyl)octane Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)CCSCCN=C=O NFJJZDSLZRMSQT-UHFFFAOYSA-N 0.000 description 1
- SKRWRXWNQFQGRU-UHFFFAOYSA-N 1,1,1,2,2,3,3,4,4,5,5,6,6-tridecafluorooctane Chemical compound CCC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F SKRWRXWNQFQGRU-UHFFFAOYSA-N 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
- 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
- FSCQZUXYTLYEIR-UHFFFAOYSA-N 2-(3-triethoxysilylpropyl)butanedioic acid Chemical compound CCO[Si](OCC)(OCC)CCCC(CC(O)=O)C(O)=O FSCQZUXYTLYEIR-UHFFFAOYSA-N 0.000 description 1
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 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 1
- 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 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
- 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
- FJDSYLLKAHIODS-UHFFFAOYSA-N 3-(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctylsulfanyl)oxolan-2-one Chemical compound FC(CCSC1C(OCC1)=O)(C(C(C(C(C(F)(F)F)(F)F)(F)F)(F)F)(F)F)F FJDSYLLKAHIODS-UHFFFAOYSA-N 0.000 description 1
- AZRRZGIBBLWSSQ-UHFFFAOYSA-N 4-ethyl-7-phenyl-3,5-diazabicyclo[2.2.2]octane-2,6-dione Chemical compound N1C(=O)C2C(=O)NC1(CC)CC2C1=CC=CC=C1 AZRRZGIBBLWSSQ-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000005697 Dodecan-1-ol Substances 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- WZSSJPURPHWAPH-UHFFFAOYSA-N F[SiH3].C(N)(O)=S Chemical compound F[SiH3].C(N)(O)=S WZSSJPURPHWAPH-UHFFFAOYSA-N 0.000 description 1
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 1
- 238000006957 Michael reaction Methods 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
- NOHQTLHHNIKWBA-UHFFFAOYSA-N [SiH4].NC(=O)N Chemical compound [SiH4].NC(=O)N NOHQTLHHNIKWBA-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
- GHWVXCQZPNWFRO-UHFFFAOYSA-N butane-2,3-diamine Chemical compound CC(N)C(C)N GHWVXCQZPNWFRO-UHFFFAOYSA-N 0.000 description 1
- PHDSHKDUDPVVGU-UHFFFAOYSA-N carbamic acid;2h-triazole Chemical compound NC(O)=O.C=1C=NNN=1 PHDSHKDUDPVVGU-UHFFFAOYSA-N 0.000 description 1
- GNVMUORYQLCPJZ-UHFFFAOYSA-N carbamothioic s-acid Chemical compound NC(S)=O GNVMUORYQLCPJZ-UHFFFAOYSA-N 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000020176 deacylation Effects 0.000 description 1
- 238000005947 deacylation reaction Methods 0.000 description 1
- AYOHIQLKSOJJQH-UHFFFAOYSA-N dibutyltin Chemical compound CCCC[Sn]CCCC AYOHIQLKSOJJQH-UHFFFAOYSA-N 0.000 description 1
- HAZBEBARJSJLFQ-UHFFFAOYSA-N dichloro(ethoxymethyl)silane Chemical compound CCOC[SiH](Cl)Cl HAZBEBARJSJLFQ-UHFFFAOYSA-N 0.000 description 1
- XWBDWHCCBGMXKG-UHFFFAOYSA-N ethanamine;hydron;chloride Chemical compound Cl.CCN XWBDWHCCBGMXKG-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
- 229920002313 fluoropolymer Polymers 0.000 description 1
- 239000004811 fluoropolymer Substances 0.000 description 1
- QWCOSMBXZZJARK-UHFFFAOYSA-N fluorosilane thiourea Chemical class F[SiH3].NC(N)=S QWCOSMBXZZJARK-UHFFFAOYSA-N 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 235000019256 formaldehyde Nutrition 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000010977 jade Substances 0.000 description 1
- 150000004658 ketimines Chemical class 0.000 description 1
- 229940070765 laurate Drugs 0.000 description 1
- 239000007788 liquid Substances 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
- QHJABUZHRJTCAR-UHFFFAOYSA-N n'-methylpropane-1,3-diamine Chemical compound CNCCCN QHJABUZHRJTCAR-UHFFFAOYSA-N 0.000 description 1
- SFUCAQIVQHAVSK-UHFFFAOYSA-N n-[2-(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctylsulfanyl)ethyl]acetamide Chemical compound CC(=O)NCCSCCC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F SFUCAQIVQHAVSK-UHFFFAOYSA-N 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 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
- 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
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
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D4/00—Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (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 |
| PCT/US2008/085109 WO2009073595A1 (en) | 2007-12-04 | 2008-12-01 | Fluoroalkyl silanes |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020107014617A Division KR101588470B1 (ko) | 2007-12-04 | 2008-12-01 | 플루오로알킬 실란 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20150140408A true KR20150140408A (ko) | 2015-12-15 |
Family
ID=40676432
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020157034132A Ceased KR20150140408A (ko) | 2007-12-04 | 2008-12-01 | 플루오로알킬 실란 |
| KR1020107014617A Expired - Fee Related KR101588470B1 (ko) | 2007-12-04 | 2008-12-01 | 플루오로알킬 실란 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020107014617A Expired - Fee Related KR101588470B1 (ko) | 2007-12-04 | 2008-12-01 | 플루오로알킬 실란 |
Country Status (9)
| Country | Link |
|---|---|
| US (3) | US8058463B2 (enExample) |
| EP (1) | EP2215098B1 (enExample) |
| JP (1) | JP5680966B2 (enExample) |
| KR (2) | KR20150140408A (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 |
| CN105102505B (zh) * | 2013-04-04 | 2017-04-05 | 旭硝子株式会社 | 含氟醚化合物、含氟醚组合物及涂布液，以及具有表面层的基材及其制造方法 |
| ES2651918T3 (es) * | 2014-01-31 | 2018-01-30 | Covestro Deutschland Ag | Formamidas modificadas con silanos |
| ES2652324T3 (es) * | 2014-01-31 | 2018-02-01 | Covestro Deutschland Ag | Formamidas modificadas con silanos |
| EP3127910B1 (en) | 2014-03-31 | 2018-08-29 | Mitsubishi Materials Corporation | Fluorine-containing silane compound |
| 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 |
| CN109476130A (zh) | 2016-07-29 | 2019-03-15 | 大金工业株式会社 | 表面处理剂和包括由该表面处理剂形成的层的物品 |
| 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 |
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| 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 KR KR1020157034132A patent/KR20150140408A/ko not_active Ceased
- 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 WO PCT/US2008/085109 patent/WO2009073595A1/en not_active Ceased
- 2008-12-01 JP JP2010537004A patent/JP5680966B2/ja not_active Expired - Fee Related
- 2008-12-01 EP EP08857672.3A patent/EP2215098B1/en not_active Not-in-force
- 2008-12-01 CA CA2706614A patent/CA2706614C/en not_active Expired - Fee Related
- 2008-12-01 AU AU2008334037A patent/AU2008334037B2/en not_active Ceased
- 2008-12-01 CN CN200880119435.0A patent/CN101889018B/zh not_active Expired - Fee Related
- 2008-12-01 NZ NZ585454A patent/NZ585454A/en not_active IP Right Cessation
-
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 |
|---|---|
| US20120022267A1 (en) | 2012-01-26 |
| US20090143598A1 (en) | 2009-06-04 |
| CA2950651A1 (en) | 2009-06-11 |
| US8058463B2 (en) | 2011-11-15 |
| WO2009073595A1 (en) | 2009-06-11 |
| KR20100101625A (ko) | 2010-09-17 |
| HK1150610A1 (en) | 2012-01-06 |
| AU2008334037B2 (en) | 2013-09-12 |
| EP2215098B1 (en) | 2014-08-20 |
| JP5680966B2 (ja) | 2015-03-04 |
| JP2011505422A (ja) | 2011-02-24 |
| NZ585454A (en) | 2012-05-25 |
| CA2706614C (en) | 2017-08-22 |
| EP2215098A1 (en) | 2010-08-11 |
| US8420826B2 (en) | 2013-04-16 |
| CA2706614A1 (en) | 2009-06-11 |
| US8501952B2 (en) | 2013-08-06 |
| CA2950651C (en) | 2018-08-28 |
| AU2008334037A1 (en) | 2009-06-11 |
| US20120022266A1 (en) | 2012-01-26 |
| CN101889018A (zh) | 2010-11-17 |
| KR101588470B1 (ko) | 2016-01-25 |
| CN101889018B (zh) | 2014-05-14 |
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