CA2730989A1 - Fluorinated ether silanes and methods of using the same - Google Patents
Fluorinated ether silanes and methods of using the same Download PDFInfo
- Publication number
- CA2730989A1 CA2730989A1 CA2730989A CA2730989A CA2730989A1 CA 2730989 A1 CA2730989 A1 CA 2730989A1 CA 2730989 A CA2730989 A CA 2730989A CA 2730989 A CA2730989 A CA 2730989A CA 2730989 A1 CA2730989 A1 CA 2730989A1
- Authority
- CA
- Canada
- Prior art keywords
- chf
- group
- hydrocarbon
- composition
- fluorinated
- 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.)
- Abandoned
Links
- 238000000034 method Methods 0.000 title claims abstract description 123
- -1 Fluorinated ether silanes Chemical class 0.000 title description 49
- 230000015572 biosynthetic process Effects 0.000 claims abstract description 141
- 150000001875 compounds Chemical class 0.000 claims abstract description 138
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 119
- 239000004215 Carbon black (E152) Substances 0.000 claims abstract description 106
- 239000000203 mixture Substances 0.000 claims description 162
- 150000002430 hydrocarbons Chemical group 0.000 claims description 117
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 98
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 67
- 239000012267 brine Substances 0.000 claims description 67
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 claims description 67
- 125000004432 carbon atom Chemical group C* 0.000 claims description 66
- 239000002904 solvent Substances 0.000 claims description 60
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 56
- 239000007789 gas Substances 0.000 claims description 44
- 125000000217 alkyl group Chemical group 0.000 claims description 38
- 239000012530 fluid Substances 0.000 claims description 37
- DCAYPVUWAIABOU-UHFFFAOYSA-N hexadecane Chemical compound CCCCCCCCCCCCCCCC DCAYPVUWAIABOU-UHFFFAOYSA-N 0.000 claims description 34
- 239000007788 liquid Substances 0.000 claims description 34
- 230000035699 permeability Effects 0.000 claims description 32
- 125000002947 alkylene group Chemical group 0.000 claims description 29
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 24
- 229910000077 silane Inorganic materials 0.000 claims description 20
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 18
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 17
- 239000002253 acid Substances 0.000 claims description 17
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 16
- 239000004576 sand Substances 0.000 claims description 16
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 claims description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 14
- 125000003545 alkoxy group Chemical group 0.000 claims description 13
- 230000000052 comparative effect Effects 0.000 claims description 12
- 239000007859 condensation product Substances 0.000 claims description 12
- 125000004423 acyloxy group Chemical group 0.000 claims description 11
- 125000003118 aryl group Chemical group 0.000 claims description 11
- 125000000524 functional group Chemical group 0.000 claims description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
- 150000002576 ketones Chemical class 0.000 claims description 11
- 125000004104 aryloxy group Chemical group 0.000 claims description 10
- 150000002148 esters Chemical class 0.000 claims description 10
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 9
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 239000002245 particle Substances 0.000 claims description 9
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 8
- 235000019738 Limestone Nutrition 0.000 claims description 8
- 150000001412 amines Chemical class 0.000 claims description 8
- 150000004820 halides Chemical group 0.000 claims description 8
- 239000006028 limestone Substances 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 6
- 230000001965 increasing effect Effects 0.000 claims description 6
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 6
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 5
- 125000000732 arylene group Chemical group 0.000 claims description 5
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 5
- 229910052782 aluminium Inorganic materials 0.000 claims description 4
- 239000001569 carbon dioxide Substances 0.000 claims description 4
- 229910002092 carbon dioxide Inorganic materials 0.000 claims description 4
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 4
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 3
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 3
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 claims description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 3
- 150000001408 amides Chemical class 0.000 claims description 3
- 239000004202 carbamide Substances 0.000 claims description 3
- 235000019253 formic acid Nutrition 0.000 claims description 3
- 125000001188 haloalkyl group Chemical group 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 claims description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 2
- 239000000908 ammonium hydroxide Substances 0.000 claims description 2
- YPJUNDFVDDCYIH-UHFFFAOYSA-N perfluorobutyric acid Chemical compound OC(=O)C(F)(F)C(F)(F)C(F)(F)F YPJUNDFVDDCYIH-UHFFFAOYSA-N 0.000 claims 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 claims description 2
- 125000001931 aliphatic group Chemical group 0.000 claims 3
- 150000004649 carbonic acid derivatives Chemical class 0.000 claims 1
- 238000005755 formation reaction Methods 0.000 abstract description 125
- 125000001183 hydrocarbyl group Chemical group 0.000 abstract 2
- 238000011282 treatment Methods 0.000 description 87
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 49
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 48
- 229920005862 polyol Polymers 0.000 description 35
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 33
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 31
- 150000003077 polyols Chemical class 0.000 description 31
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 27
- 206010017076 Fracture Diseases 0.000 description 23
- 208000010392 Bone Fractures Diseases 0.000 description 20
- 238000006243 chemical reaction Methods 0.000 description 20
- 238000002347 injection Methods 0.000 description 19
- 239000007924 injection Substances 0.000 description 19
- 239000000243 solution Substances 0.000 description 19
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
- 239000000463 material Substances 0.000 description 18
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 18
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 17
- 229910052757 nitrogen Inorganic materials 0.000 description 14
- 150000003839 salts Chemical class 0.000 description 14
- 239000002585 base Substances 0.000 description 13
- 239000000758 substrate Substances 0.000 description 13
- 239000000919 ceramic Substances 0.000 description 12
- 239000011521 glass Substances 0.000 description 12
- 239000003960 organic solvent Substances 0.000 description 12
- 229920000642 polymer Polymers 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 12
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 11
- 239000003921 oil Substances 0.000 description 11
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 238000001556 precipitation Methods 0.000 description 10
- 239000005871 repellent Substances 0.000 description 10
- 238000000576 coating method Methods 0.000 description 9
- 239000006185 dispersion Substances 0.000 description 9
- 150000004702 methyl esters Chemical class 0.000 description 9
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 8
- 230000008859 change Effects 0.000 description 8
- 230000006872 improvement Effects 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- 239000004575 stone Substances 0.000 description 8
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 7
- 239000011248 coating agent Substances 0.000 description 7
- 239000012141 concentrate Substances 0.000 description 7
- 238000009472 formulation Methods 0.000 description 7
- 238000010438 heat treatment Methods 0.000 description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
- 230000003068 static effect Effects 0.000 description 7
- 239000004094 surface-active agent Substances 0.000 description 7
- QCAHUFWKIQLBNB-UHFFFAOYSA-N 3-(3-methoxypropoxy)propan-1-ol Chemical compound COCCCOCCCO QCAHUFWKIQLBNB-UHFFFAOYSA-N 0.000 description 6
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- 238000011156 evaluation Methods 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- 239000004033 plastic Substances 0.000 description 6
- 229920003023 plastic Polymers 0.000 description 6
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 5
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 5
- 208000035874 Excoriation Diseases 0.000 description 5
- 238000005299 abrasion Methods 0.000 description 5
- 239000000654 additive Substances 0.000 description 5
- 150000001336 alkenes Chemical class 0.000 description 5
- 238000004140 cleaning Methods 0.000 description 5
- 238000006073 displacement reaction Methods 0.000 description 5
- 150000002367 halogens Chemical group 0.000 description 5
- 230000007062 hydrolysis Effects 0.000 description 5
- 238000006460 hydrolysis reaction Methods 0.000 description 5
- 150000007524 organic acids Chemical class 0.000 description 5
- 230000002940 repellent Effects 0.000 description 5
- 125000005372 silanol group Chemical group 0.000 description 5
- 238000004381 surface treatment Methods 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- 239000002023 wood Substances 0.000 description 5
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 4
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 4
- 238000004566 IR spectroscopy Methods 0.000 description 4
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 4
- 239000004721 Polyphenylene oxide Substances 0.000 description 4
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 4
- 229910000019 calcium carbonate Inorganic materials 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
- 150000001733 carboxylic acid esters Chemical class 0.000 description 4
- 150000001735 carboxylic acids Chemical class 0.000 description 4
- 238000009833 condensation Methods 0.000 description 4
- 230000005494 condensation Effects 0.000 description 4
- 238000006482 condensation reaction Methods 0.000 description 4
- 125000004122 cyclic group Chemical group 0.000 description 4
- 150000002170 ethers Chemical class 0.000 description 4
- 239000004744 fabric Substances 0.000 description 4
- 238000003682 fluorination reaction Methods 0.000 description 4
- 239000010982 man-made stone Substances 0.000 description 4
- 239000004579 marble Substances 0.000 description 4
- 238000010128 melt processing Methods 0.000 description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
- OEIJHBUUFURJLI-UHFFFAOYSA-N octane-1,8-diol Chemical compound OCCCCCCCCO OEIJHBUUFURJLI-UHFFFAOYSA-N 0.000 description 4
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 4
- 229920000570 polyether Polymers 0.000 description 4
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 4
- 239000011148 porous material Substances 0.000 description 4
- 239000000523 sample Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 229920001169 thermoplastic Polymers 0.000 description 4
- RWNUSVWFHDHRCJ-UHFFFAOYSA-N 1-butoxypropan-2-ol Chemical compound CCCCOCC(C)O RWNUSVWFHDHRCJ-UHFFFAOYSA-N 0.000 description 3
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 3
- SJECZPVISLOESU-UHFFFAOYSA-N 3-trimethoxysilylpropan-1-amine Chemical compound CO[Si](OC)(OC)CCCN SJECZPVISLOESU-UHFFFAOYSA-N 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 241000364021 Tulsa Species 0.000 description 3
- NJSVDVPGINTNGX-UHFFFAOYSA-N [dimethoxy(propyl)silyl]oxymethanamine Chemical compound CCC[Si](OC)(OC)OCN NJSVDVPGINTNGX-UHFFFAOYSA-N 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 238000000137 annealing Methods 0.000 description 3
- 239000012298 atmosphere Substances 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000007796 conventional method Methods 0.000 description 3
- 239000011222 crystalline ceramic Substances 0.000 description 3
- 229910002106 crystalline ceramic Inorganic materials 0.000 description 3
- 239000006092 crystalline glass-ceramic Substances 0.000 description 3
- 229910001873 dinitrogen Inorganic materials 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 239000000835 fiber Substances 0.000 description 3
- 238000009408 flooring Methods 0.000 description 3
- 239000010438 granite Substances 0.000 description 3
- 230000003993 interaction Effects 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 3
- 235000005985 organic acids Nutrition 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 229920001451 polypropylene glycol Polymers 0.000 description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- 238000005086 pumping Methods 0.000 description 3
- 150000004756 silanes Chemical class 0.000 description 3
- 229910000033 sodium borohydride Inorganic materials 0.000 description 3
- 239000012279 sodium borohydride Substances 0.000 description 3
- 238000005507 spraying Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000004416 thermosoftening plastic Substances 0.000 description 3
- FRGPKMWIYVTFIQ-UHFFFAOYSA-N triethoxy(3-isocyanatopropyl)silane Chemical compound CCO[Si](OCC)(OCC)CCCN=C=O FRGPKMWIYVTFIQ-UHFFFAOYSA-N 0.000 description 3
- JLGLQAWTXXGVEM-UHFFFAOYSA-N triethylene glycol monomethyl ether Chemical compound COCCOCCOCCO JLGLQAWTXXGVEM-UHFFFAOYSA-N 0.000 description 3
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 3
- 239000000341 volatile oil Substances 0.000 description 3
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
- DQKFYZUPDCUPFE-UHFFFAOYSA-N 2-butoxyethanol;ethanol Chemical compound CCO.CCCCOCCO DQKFYZUPDCUPFE-UHFFFAOYSA-N 0.000 description 2
- BOZRCGLDOHDZBP-UHFFFAOYSA-N 2-ethylhexanoic acid;tin Chemical compound [Sn].CCCCC(CC)C(O)=O BOZRCGLDOHDZBP-UHFFFAOYSA-N 0.000 description 2
- OXYZDRAJMHGSMW-UHFFFAOYSA-N 3-chloropropyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)CCCCl OXYZDRAJMHGSMW-UHFFFAOYSA-N 0.000 description 2
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 2
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical group NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- 241001251094 Formica Species 0.000 description 2
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- BOTDANWDWHJENH-UHFFFAOYSA-N Tetraethyl orthosilicate Chemical compound CCO[Si](OCC)(OCC)OCC BOTDANWDWHJENH-UHFFFAOYSA-N 0.000 description 2
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 229910001570 bauxite Inorganic materials 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 230000000903 blocking effect Effects 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 239000001110 calcium chloride Substances 0.000 description 2
- 229910001628 calcium chloride Inorganic materials 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000004568 cement Substances 0.000 description 2
- 239000004927 clay Substances 0.000 description 2
- 239000004567 concrete Substances 0.000 description 2
- 239000010779 crude oil Substances 0.000 description 2
- 230000006324 decarbonylation Effects 0.000 description 2
- 238000006606 decarbonylation reaction Methods 0.000 description 2
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- 150000003254 radicals Chemical class 0.000 description 1
- 239000012713 reactive precursor Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000003134 recirculating effect Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 239000011819 refractory material Substances 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 239000002455 scale inhibitor Substances 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 239000010454 slate Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 230000007480 spreading Effects 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 229910001631 strontium chloride Inorganic materials 0.000 description 1
- AHBGXTDRMVNFER-UHFFFAOYSA-L strontium dichloride Chemical compound [Cl-].[Cl-].[Sr+2] AHBGXTDRMVNFER-UHFFFAOYSA-L 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 125000003698 tetramethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- LFQCEHFDDXELDD-UHFFFAOYSA-N tetramethyl orthosilicate Chemical compound CO[Si](OC)(OC)OC LFQCEHFDDXELDD-UHFFFAOYSA-N 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 239000012815 thermoplastic material Substances 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- JMXKSZRRTHPKDL-UHFFFAOYSA-N titanium(IV) ethoxide Substances [Ti+4].CC[O-].CC[O-].CC[O-].CC[O-] JMXKSZRRTHPKDL-UHFFFAOYSA-N 0.000 description 1
- VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 description 1
- 230000001052 transient effect Effects 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- CPUDPFPXCZDNGI-UHFFFAOYSA-N triethoxy(methyl)silane Chemical compound CCO[Si](C)(OCC)OCC CPUDPFPXCZDNGI-UHFFFAOYSA-N 0.000 description 1
- FZMJEGJVKFTGMU-UHFFFAOYSA-N triethoxy(octadecyl)silane Chemical compound CCCCCCCCCCCCCCCCCC[Si](OCC)(OCC)OCC FZMJEGJVKFTGMU-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 150000004072 triols Chemical class 0.000 description 1
- 238000011144 upstream manufacturing Methods 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
- 238000005406 washing Methods 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Materials Applied To Surfaces To Minimize Adherence Of Mist Or Water (AREA)
- Lubricants (AREA)
- Treatments Of Macromolecular Shaped Articles (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US8193608P | 2008-07-18 | 2008-07-18 | |
| US61/081,936 | 2008-07-18 | ||
| US13873408P | 2008-12-18 | 2008-12-18 | |
| US61/138,734 | 2008-12-18 | ||
| PCT/US2009/050810 WO2010009296A2 (en) | 2008-07-18 | 2009-07-16 | Fluorinated ether silanes and methods of using the same |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2730989A1 true CA2730989A1 (en) | 2010-01-21 |
Family
ID=41171278
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2730989A Abandoned CA2730989A1 (en) | 2008-07-18 | 2009-07-16 | Fluorinated ether silanes and methods of using the same |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US20110124532A1 (enExample) |
| EP (1) | EP2321326A2 (enExample) |
| JP (1) | JP2011528663A (enExample) |
| CN (1) | CN102149720A (enExample) |
| BR (1) | BRPI0915959A2 (enExample) |
| CA (1) | CA2730989A1 (enExample) |
| EA (1) | EA201100051A1 (enExample) |
| MX (1) | MX2011000701A (enExample) |
| WO (1) | WO2010009296A2 (enExample) |
Families Citing this family (34)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008147796A1 (en) * | 2007-05-23 | 2008-12-04 | 3M Innovative Properties Company | Aqueous compositions of fluorinated surfactants and methods of using the same |
| EP2160421A1 (en) * | 2007-06-06 | 2010-03-10 | 3M Innovative Properties Company | Fluorinated ether compositions and methods of using the same |
| WO2009085936A1 (en) * | 2007-12-21 | 2009-07-09 | 3M Innovative Properties Company | Fluorinated polymer compositions and methods for treating hydrocarbon-bearing formations using the same |
| CN101945971A (zh) * | 2007-12-21 | 2011-01-12 | 3M创新有限公司 | 利用氟化聚合物组合物处理含烃地层的方法 |
| AU2009244574A1 (en) | 2008-05-05 | 2009-11-12 | 3M Innovative Properties Company | Methods for treating hydrocarbon-bearing formations having brine |
| WO2010009182A2 (en) * | 2008-07-18 | 2010-01-21 | 3M Innovative Properties Company | Cationic fluorinated polymer compositions and methods for treating hydrocarbon-bearing formations using the same |
| MX2011000702A (es) * | 2008-07-18 | 2011-02-24 | 3M Innovative Properties Co | Compuestos de eter fluorados y metodos para usar los mismos. |
| US20110232530A1 (en) * | 2008-11-25 | 2011-09-29 | Dams Rudolf J | Fluorinated ether urethanes and methods of using the same |
| CN102317403A (zh) | 2008-12-18 | 2012-01-11 | 3M创新有限公司 | 使含烃地层与氟化醚组合物接触的方法 |
| WO2010080353A2 (en) | 2008-12-18 | 2010-07-15 | 3M Innovative Properties Company | Method of contacting hydrocarbon-bearing formations with fluorinated phosphate and phosphonate compositions |
| WO2011005672A2 (en) | 2009-07-09 | 2011-01-13 | 3M Innovative Properties Company | Methods for treating carbonate hydrocarbon-bearing formations with fluorinated amphoteric compounds |
| BR112013015611A2 (pt) | 2010-12-20 | 2018-05-15 | 3M Innovative Properties Co | métodos para tratamento de formações contendo hidrocarboneto e carbonato com óxidos de amina fluorado. |
| EP2655544A4 (en) | 2010-12-21 | 2015-01-14 | 3M Innovative Properties Co | METHOD FOR TREATING HYDROCARBON-BASED FORMATIONS WITH FLUORINATED AMINE |
| MX350762B (es) | 2011-01-13 | 2017-09-18 | 3M Innovative Properties Co | Metodos para tratar formaciones que tienen hidrocarburo siliciclastico con oxidos de amina fluorados. |
| JP5747699B2 (ja) * | 2011-07-12 | 2015-07-15 | 信越化学工業株式会社 | フルオロオキシアルキレン基含有ポリマー変性シラン及び該シランを含む表面処理剤並びに該表面処理剤で表面処理された物品 |
| CN104105776B (zh) * | 2011-12-21 | 2019-05-31 | 联邦科学与工业研究组织 | 对碳酸盐表面进行化学吸附的方法 |
| US10106724B2 (en) | 2012-11-19 | 2018-10-23 | 3M Innovative Properties Company | Method of contacting hydrocarbon-bearing formations with fluorinated ionic polymers |
| CN105263973B (zh) | 2012-11-19 | 2019-06-14 | 3M创新有限公司 | 包含氟化聚合物和非氟化聚合物的组合物及其制备和使用方法 |
| US20140144631A1 (en) * | 2012-11-28 | 2014-05-29 | Halliburton Energy Services, Inc | Methods of Forming Functionalized Proppant Particulates for Use in Subterranean Formation Operations |
| US9938306B2 (en) | 2013-10-04 | 2018-04-10 | 3M Innovative Properties Company | Fluoroalkylsilanes and coatings therefrom |
| WO2015115522A1 (ja) * | 2014-01-31 | 2015-08-06 | Dic株式会社 | 表面改質剤、コーティング組成物及び物品 |
| WO2016006584A1 (ja) * | 2014-07-07 | 2016-01-14 | ダイキン工業株式会社 | パーフルオロ（ポリ）エーテル変性アミドシラン化合物を含む組成物 |
| WO2017018489A1 (ja) * | 2015-07-30 | 2017-02-02 | 旭硝子株式会社 | 含フッ素化合物、硬化性組成物および硬化物 |
| WO2017022437A1 (ja) * | 2015-07-31 | 2017-02-09 | ダイキン工業株式会社 | パーフルオロ（ポリ）エーテル基含有シラン化合物 |
| KR102752864B1 (ko) | 2015-09-01 | 2025-01-09 | 에이지씨 가부시키가이샤 | 함불소 에테르 화합물, 함불소 에테르 조성물, 코팅액 및 물품 |
| WO2018078906A1 (ja) * | 2016-10-31 | 2018-05-03 | 旭硝子株式会社 | 含フッ素エーテル組成物、コーティング液および物品 |
| JP7156276B2 (ja) * | 2017-05-26 | 2022-10-19 | Ａｇｃ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、コーティング液、物品およびその製造方法 |
| KR102268922B1 (ko) * | 2018-05-16 | 2021-06-24 | 광저우 유알 매터리얼 테크놀로지 컴퍼니 리미티드 | 퍼플루오로폴리에테르기 함유 실란화합물, 이의 제조방법, 표면처리제 및 물품 |
| JP7849144B2 (ja) * | 2018-11-28 | 2026-04-21 | Ａｇｃ株式会社 | 含フッ素エーテル化合物、組成物、物品および物品の製造方法 |
| CN109370750A (zh) * | 2018-12-26 | 2019-02-22 | 合肥普庆新材料科技有限公司 | 一种环保型纯油性冷轧轧制油 |
| JP2021146713A (ja) * | 2020-03-23 | 2021-09-27 | 東芝テック株式会社 | 撥液性部材、天板及び製品 |
| JP2022115807A (ja) * | 2021-01-28 | 2022-08-09 | ダイキン工業株式会社 | フルオロポリエーテル基含有シラン化合物を含有する組成物 |
| FR3130286B1 (fr) * | 2021-12-10 | 2023-12-22 | Farevacare | Composition hydrophobe et oleophobe, sous la forme aerosol |
| CN119790105A (zh) * | 2022-09-06 | 2025-04-08 | 信越化学工业株式会社 | 含氟组合物、表面处理剂和物品 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| US6613860B1 (en) * | 2000-10-12 | 2003-09-02 | 3M Innovative Properties Company | Compositions comprising fluorinated polyether silanes for rendering substrates oil and water repellent |
| US6656258B2 (en) * | 2001-03-20 | 2003-12-02 | 3M Innovative Properties Company | Compositions comprising fluorinated silanes and compressed fluid CO2 |
| US6649272B2 (en) * | 2001-11-08 | 2003-11-18 | 3M Innovative Properties Company | Coating composition comprising fluorochemical polyether silane polycondensate and use thereof |
| US6958191B2 (en) * | 2002-08-29 | 2005-10-25 | Shin-Etsu Chemical Co., Ltd. | Lens with stain resistant surface layer |
| US8002886B2 (en) * | 2006-12-15 | 2011-08-23 | 3M Innovative Properties Company | Fluorochemical urethane compounds having pendent silyl groups used for surface treatment |
-
2009
- 2009-07-16 EP EP09790522A patent/EP2321326A2/en not_active Withdrawn
- 2009-07-16 MX MX2011000701A patent/MX2011000701A/es not_active Application Discontinuation
- 2009-07-16 CN CN2009801355018A patent/CN102149720A/zh active Pending
- 2009-07-16 US US13/054,579 patent/US20110124532A1/en not_active Abandoned
- 2009-07-16 WO PCT/US2009/050810 patent/WO2010009296A2/en not_active Ceased
- 2009-07-16 EA EA201100051A patent/EA201100051A1/ru unknown
- 2009-07-16 JP JP2011518905A patent/JP2011528663A/ja not_active Withdrawn
- 2009-07-16 CA CA2730989A patent/CA2730989A1/en not_active Abandoned
- 2009-07-16 BR BRPI0915959A patent/BRPI0915959A2/pt not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| WO2010009296A2 (en) | 2010-01-21 |
| CN102149720A (zh) | 2011-08-10 |
| EP2321326A2 (en) | 2011-05-18 |
| BRPI0915959A2 (pt) | 2019-09-24 |
| MX2011000701A (es) | 2011-02-25 |
| WO2010009296A3 (en) | 2010-07-22 |
| EA201100051A1 (ru) | 2011-08-30 |
| US20110124532A1 (en) | 2011-05-26 |
| JP2011528663A (ja) | 2011-11-24 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |
Effective date: 20130716 |