WO2014167388A1 - A surface protection material and a production method thereof - Google Patents
A surface protection material and a production method thereof Download PDFInfo
- Publication number
- WO2014167388A1 WO2014167388A1 PCT/IB2013/052927 IB2013052927W WO2014167388A1 WO 2014167388 A1 WO2014167388 A1 WO 2014167388A1 IB 2013052927 W IB2013052927 W IB 2013052927W WO 2014167388 A1 WO2014167388 A1 WO 2014167388A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- alkoxy silane
- ammonium compound
- surface protection
- protection material
- functional
- Prior art date
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- 239000000463 material Substances 0.000 title claims abstract description 37
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 30
- -1 alkoxy silane Chemical compound 0.000 claims abstract description 43
- 229910000077 silane Inorganic materials 0.000 claims abstract description 42
- 150000003868 ammonium compounds Chemical class 0.000 claims abstract description 36
- 125000000524 functional group Chemical group 0.000 claims abstract description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 15
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims abstract description 12
- 229910052710 silicon Inorganic materials 0.000 claims abstract description 12
- 239000010703 silicon Substances 0.000 claims abstract description 12
- 238000005809 transesterification reaction Methods 0.000 claims abstract description 11
- 230000015572 biosynthetic process Effects 0.000 claims abstract description 5
- 230000002194 synthesizing effect Effects 0.000 claims abstract description 5
- 241000233866 Fungi Species 0.000 claims abstract description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract 2
- 229910052799 carbon Inorganic materials 0.000 claims abstract 2
- 125000000217 alkyl group Chemical group 0.000 claims description 21
- 125000004432 carbon atom Chemical group C* 0.000 claims description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
- 150000001412 amines Chemical class 0.000 claims description 9
- 239000004593 Epoxy Substances 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 239000012948 isocyanate Substances 0.000 claims description 7
- 150000002513 isocyanates Chemical class 0.000 claims description 7
- 239000003054 catalyst Substances 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 claims description 6
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 6
- 229920002554 vinyl polymer Polymers 0.000 claims description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 5
- 230000003301 hydrolyzing effect Effects 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 4
- MSRJTTSHWYDFIU-UHFFFAOYSA-N octyltriethoxysilane Chemical compound CCCCCCCC[Si](OCC)(OCC)OCC MSRJTTSHWYDFIU-UHFFFAOYSA-N 0.000 claims description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 230000000845 anti-microbial effect Effects 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- 150000003512 tertiary amines Chemical class 0.000 claims description 3
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 claims description 3
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 claims description 2
- KKYDYRWEUFJLER-UHFFFAOYSA-N 1,1,2,2,3,3,4,4,5,5,6,6,7,7,10,10,10-heptadecafluorodecyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)CCC(F)(F)F KKYDYRWEUFJLER-UHFFFAOYSA-N 0.000 claims description 2
- AWWLLLDRXYQXCS-UHFFFAOYSA-N 2-methyl-3-sulfanylprop-2-enoic acid Chemical compound SC=C(C)C(O)=O AWWLLLDRXYQXCS-UHFFFAOYSA-N 0.000 claims description 2
- DOYKFSOCSXVQAN-UHFFFAOYSA-N 3-[diethoxy(methyl)silyl]propyl 2-methylprop-2-enoate Chemical compound CCO[Si](C)(OCC)CCCOC(=O)C(C)=C DOYKFSOCSXVQAN-UHFFFAOYSA-N 0.000 claims description 2
- LZMNXXQIQIHFGC-UHFFFAOYSA-N 3-[dimethoxy(methyl)silyl]propyl 2-methylprop-2-enoate Chemical compound CO[Si](C)(OC)CCCOC(=O)C(C)=C LZMNXXQIQIHFGC-UHFFFAOYSA-N 0.000 claims description 2
- ZPZDIFSPRVHGIF-UHFFFAOYSA-N 3-aminopropylsilicon Chemical compound NCCC[Si] ZPZDIFSPRVHGIF-UHFFFAOYSA-N 0.000 claims description 2
- URDOJQUSEUXVRP-UHFFFAOYSA-N 3-triethoxysilylpropyl 2-methylprop-2-enoate Chemical compound CCO[Si](OCC)(OCC)CCCOC(=O)C(C)=C URDOJQUSEUXVRP-UHFFFAOYSA-N 0.000 claims description 2
- SJECZPVISLOESU-UHFFFAOYSA-N 3-trimethoxysilylpropan-1-amine Chemical compound CO[Si](OC)(OC)CCCN SJECZPVISLOESU-UHFFFAOYSA-N 0.000 claims description 2
- XDLMVUHYZWKMMD-UHFFFAOYSA-N 3-trimethoxysilylpropyl 2-methylprop-2-enoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C(C)=C XDLMVUHYZWKMMD-UHFFFAOYSA-N 0.000 claims description 2
- KBQVDAIIQCXKPI-UHFFFAOYSA-N 3-trimethoxysilylpropyl prop-2-enoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C=C KBQVDAIIQCXKPI-UHFFFAOYSA-N 0.000 claims description 2
- BESKSSIEODQWBP-UHFFFAOYSA-N 3-tris(trimethylsilyloxy)silylpropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCC[Si](O[Si](C)(C)C)(O[Si](C)(C)C)O[Si](C)(C)C BESKSSIEODQWBP-UHFFFAOYSA-N 0.000 claims description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 claims description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims description 2
- 229910019142 PO4 Inorganic materials 0.000 claims description 2
- 108010009736 Protein Hydrolysates Proteins 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 2
- PSDYQSWHANEKRV-UHFFFAOYSA-N [S]N Chemical compound [S]N PSDYQSWHANEKRV-UHFFFAOYSA-N 0.000 claims description 2
- GXDZOSLIAABYHM-UHFFFAOYSA-N [diethoxy(methyl)silyl]methyl 2-methylprop-2-enoate Chemical compound CCO[Si](C)(OCC)COC(=O)C(C)=C GXDZOSLIAABYHM-UHFFFAOYSA-N 0.000 claims description 2
- YBUIRAZOPRQNDE-UHFFFAOYSA-N [dimethoxy(methyl)silyl]methyl 2-methylprop-2-enoate Chemical compound CO[Si](C)(OC)COC(=O)C(C)=C YBUIRAZOPRQNDE-UHFFFAOYSA-N 0.000 claims description 2
- 150000001450 anions Chemical class 0.000 claims description 2
- XGZGKDQVCBHSGI-UHFFFAOYSA-N butyl(triethoxy)silane Chemical compound CCCC[Si](OCC)(OCC)OCC XGZGKDQVCBHSGI-UHFFFAOYSA-N 0.000 claims description 2
- SXPLZNMUBFBFIA-UHFFFAOYSA-N butyl(trimethoxy)silane Chemical compound CCCC[Si](OC)(OC)OC SXPLZNMUBFBFIA-UHFFFAOYSA-N 0.000 claims description 2
- BAAAEEDPKUHLID-UHFFFAOYSA-N decyl(triethoxy)silane Chemical compound CCCCCCCCCC[Si](OCC)(OCC)OCC BAAAEEDPKUHLID-UHFFFAOYSA-N 0.000 claims description 2
- KQAHMVLQCSALSX-UHFFFAOYSA-N decyl(trimethoxy)silane Chemical compound CCCCCCCCCC[Si](OC)(OC)OC KQAHMVLQCSALSX-UHFFFAOYSA-N 0.000 claims description 2
- VJYNTADJZPKUAF-UHFFFAOYSA-N diethoxy-methyl-(3,3,3-trifluoropropyl)silane Chemical compound CCO[Si](C)(OCC)CCC(F)(F)F VJYNTADJZPKUAF-UHFFFAOYSA-N 0.000 claims description 2
- OTARVPUIYXHRRB-UHFFFAOYSA-N diethoxy-methyl-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](C)(OCC)CCCOCC1CO1 OTARVPUIYXHRRB-UHFFFAOYSA-N 0.000 claims description 2
- DIJRHOZMLZRNLM-UHFFFAOYSA-N dimethoxy-methyl-(3,3,3-trifluoropropyl)silane Chemical compound CO[Si](C)(OC)CCC(F)(F)F DIJRHOZMLZRNLM-UHFFFAOYSA-N 0.000 claims description 2
- WHGNXNCOTZPEEK-UHFFFAOYSA-N dimethoxy-methyl-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](C)(OC)CCCOCC1CO1 WHGNXNCOTZPEEK-UHFFFAOYSA-N 0.000 claims description 2
- GOIPELYWYGMEFQ-UHFFFAOYSA-N dimethoxy-methyl-octylsilane Chemical compound CCCCCCCC[Si](C)(OC)OC GOIPELYWYGMEFQ-UHFFFAOYSA-N 0.000 claims description 2
- YGUFXEJWPRRAEK-UHFFFAOYSA-N dodecyl(triethoxy)silane Chemical compound CCCCCCCCCCCC[Si](OCC)(OCC)OCC YGUFXEJWPRRAEK-UHFFFAOYSA-N 0.000 claims description 2
- SCPWMSBAGXEGPW-UHFFFAOYSA-N dodecyl(trimethoxy)silane Chemical compound CCCCCCCCCCCC[Si](OC)(OC)OC SCPWMSBAGXEGPW-UHFFFAOYSA-N 0.000 claims description 2
- PELGKMTVNFFDDL-UHFFFAOYSA-N dodecyl-dimethoxy-methylsilane Chemical compound CCCCCCCCCCCC[Si](C)(OC)OC PELGKMTVNFFDDL-UHFFFAOYSA-N 0.000 claims description 2
- FWDBOZPQNFPOLF-UHFFFAOYSA-N ethenyl(triethoxy)silane Chemical compound CCO[Si](OCC)(OCC)C=C FWDBOZPQNFPOLF-UHFFFAOYSA-N 0.000 claims description 2
- NKSJNEHGWDZZQF-UHFFFAOYSA-N ethenyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)C=C NKSJNEHGWDZZQF-UHFFFAOYSA-N 0.000 claims description 2
- JEWCZPTVOYXPGG-UHFFFAOYSA-N ethenyl-ethoxy-dimethylsilane Chemical compound CCO[Si](C)(C)C=C JEWCZPTVOYXPGG-UHFFFAOYSA-N 0.000 claims description 2
- WOXXJEVNDJOOLV-UHFFFAOYSA-N ethenyl-tris(2-methoxyethoxy)silane Chemical compound COCCO[Si](OCCOC)(OCCOC)C=C WOXXJEVNDJOOLV-UHFFFAOYSA-N 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 238000009472 formulation Methods 0.000 claims description 2
- RSKGMYDENCAJEN-UHFFFAOYSA-N hexadecyl(trimethoxy)silane Chemical compound CCCCCCCCCCCCCCCC[Si](OC)(OC)OC RSKGMYDENCAJEN-UHFFFAOYSA-N 0.000 claims description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 2
- 239000011707 mineral Substances 0.000 claims description 2
- 235000010755 mineral Nutrition 0.000 claims description 2
- 229960003493 octyltriethoxysilane Drugs 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 2
- 239000010452 phosphate Substances 0.000 claims description 2
- 125000004193 piperazinyl group Chemical group 0.000 claims description 2
- 235000009518 sodium iodide Nutrition 0.000 claims description 2
- 229910021653 sulphate ion Inorganic materials 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
- ZLGWXNBXAXOQBG-UHFFFAOYSA-N triethoxy(3,3,3-trifluoropropyl)silane Chemical compound CCO[Si](OCC)(OCC)CCC(F)(F)F ZLGWXNBXAXOQBG-UHFFFAOYSA-N 0.000 claims description 2
- OYGYKEULCAINCL-UHFFFAOYSA-N triethoxy(hexadecyl)silane Chemical compound CCCCCCCCCCCCCCCC[Si](OCC)(OCC)OCC OYGYKEULCAINCL-UHFFFAOYSA-N 0.000 claims description 2
- NBXZNTLFQLUFES-UHFFFAOYSA-N triethoxy(propyl)silane Chemical compound CCC[Si](OCC)(OCC)OCC NBXZNTLFQLUFES-UHFFFAOYSA-N 0.000 claims description 2
- UDUKMRHNZZLJRB-UHFFFAOYSA-N triethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OCC)(OCC)OCC)CCC2OC21 UDUKMRHNZZLJRB-UHFFFAOYSA-N 0.000 claims description 2
- JXUKBNICSRJFAP-UHFFFAOYSA-N triethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCOCC1CO1 JXUKBNICSRJFAP-UHFFFAOYSA-N 0.000 claims description 2
- UZIAQVMNAXPCJQ-UHFFFAOYSA-N triethoxysilylmethyl 2-methylprop-2-enoate Chemical compound CCO[Si](OCC)(OCC)COC(=O)C(C)=C UZIAQVMNAXPCJQ-UHFFFAOYSA-N 0.000 claims description 2
- JLGNHOJUQFHYEZ-UHFFFAOYSA-N trimethoxy(3,3,3-trifluoropropyl)silane Chemical compound CO[Si](OC)(OC)CCC(F)(F)F JLGNHOJUQFHYEZ-UHFFFAOYSA-N 0.000 claims description 2
- NMEPHPOFYLLFTK-UHFFFAOYSA-N trimethoxy(octyl)silane Chemical compound CCCCCCCC[Si](OC)(OC)OC NMEPHPOFYLLFTK-UHFFFAOYSA-N 0.000 claims description 2
- HQYALQRYBUJWDH-UHFFFAOYSA-N trimethoxy(propyl)silane Chemical compound CCC[Si](OC)(OC)OC HQYALQRYBUJWDH-UHFFFAOYSA-N 0.000 claims description 2
- DQZNLOXENNXVAD-UHFFFAOYSA-N trimethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OC)(OC)OC)CCC2OC21 DQZNLOXENNXVAD-UHFFFAOYSA-N 0.000 claims description 2
- HLOLETUOZGAKMT-UHFFFAOYSA-N trimethoxysilyl 2-methylprop-2-enoate Chemical compound CO[Si](OC)(OC)OC(=O)C(C)=C HLOLETUOZGAKMT-UHFFFAOYSA-N 0.000 claims description 2
- UOKUUKOEIMCYAI-UHFFFAOYSA-N trimethoxysilylmethyl 2-methylprop-2-enoate Chemical compound CO[Si](OC)(OC)COC(=O)C(C)=C UOKUUKOEIMCYAI-UHFFFAOYSA-N 0.000 claims description 2
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims 1
- 238000009413 insulation Methods 0.000 abstract description 4
- 238000006243 chemical reaction Methods 0.000 description 8
- 239000007864 aqueous solution Substances 0.000 description 4
- OXYZDRAJMHGSMW-UHFFFAOYSA-N 3-chloropropyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)CCCCl OXYZDRAJMHGSMW-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 150000003961 organosilicon compounds Chemical class 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000012975 dibutyltin dilaurate Substances 0.000 description 1
- 238000007306 functionalization reaction Methods 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000012974 tin catalyst Substances 0.000 description 1
Classifications
-
- 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
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/16—Antifouling paints; Underwater paints
- C09D5/1606—Antifouling paints; Underwater paints characterised by the anti-fouling agent
- C09D5/1612—Non-macromolecular compounds
-
- 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 System
- 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
- 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
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/16—Antifouling paints; Underwater paints
- C09D5/1656—Antifouling paints; Underwater paints characterised by the film-forming substance
- C09D5/1662—Synthetic film-forming substance
- C09D5/1675—Polyorganosiloxane-containing compositions
-
- 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
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/14—Paints containing biocides, e.g. fungicides, insecticides or pesticides
Definitions
- the present invention relates to a water soluble organosilicon surface protection material, which, upon being coated on inorganic and organic surfaces, enables protection of the surface against external factors and mold and fungus formation and provides water insulation; and a production method thereof.
- An objective of the present invention is to provide a water soluble organosilicon- based surface protection material.
- Another objective of the present invention is to provide a surface protection material production method wherein transesterification process is performed for ensuring stability during preparation of aqueous solutions of organosilicons.
- a further objective of the present invention is to provide a surface protection material production method wherein a compound obtained by transesterification reaction is functionalized by being reacted with an alkoxy silane containing a functional group.
- Another objective of the present invention is to provide a surface protection material production method wherein, by carrying out the functionalization reaction in presence of a catalyst, production time is decreased, temperature and pressure values required for the reaction are decreased and thus costs are reduced.
- Another objective of the present invention is to provide a surface protection material production method wherein hydrophobicity and antimicrobial property, adherence to the surface and hydrolytic stability are provided to the material depending on the functional group that is added.
- FIG. 1 is the view of the flowchart of the surface protection material production method.
- the surface protection material production method (100) developed to fulfill the objective of the present invention comprises the steps of
- a tertiary amine and an alkoxy silane are reacted in the presence of a catalyst and a solvent, and an alkoxy silane functional quaternized ammonium compound is obtained (101).
- methanol is used as the solvent and sodium iodide is used as the catalyst.
- synthesis (101) of a 3- chloropropyltrimethoxysilane functional quaternized ammonium compound is performed by reaction of a tertiary amine and 3-chloropropyltrimethoxysilane. The said reaction is as follows:
- the synthesized alkoxy silane functional quatemized ammonium compound is subjected to a transesterification reaction with glycol ether and the methoxy group within the compound is enabled to be substituted with this glycol ether (102).
- the purpose of transesterification process (102) is to enable the aqueous solutions of the final material to be stable.
- silicon quatemized ammonium is obtained and the released methanol is collected in the condenser.
- the 3-chloropropyltrimethoxysilane functional quatemized ammonium obtained in step (101) is reacted with ethylene glycol and transesterification is performed (102).
- the said reaction is as follows:
- the silicon quaternized ammonium compound obtained in step (102) is functionalized by being reacted with a functional alkoxy silane (103).
- a functional alkoxy silane 103
- an alkyl, amine, epoxy, mercapto, methacrylate, vinyl, isocyanate or flouro functional alkoxy silane is used.
- the silicon quaternized ammonium compound obtained as a result has the following formulation
- Ri is an alkyl group containing one to four carbon atoms
- R 2 is an alkyl group containing one to twenty two carbon atoms
- x has a value of from two to ten and R V1 is a perflluoroalkyl radical having one to twelve carbon atoms,
- R 3 is an alkyl group containing one to twenty two carbon atoms
- R4 is an alkyl group containing one to four carbon atoms
- R5 is an alkyl group containing one to four carbon atoms
- a is a value of zero, one or two
- R 6 is an alkoxy group containing one to four carbon atoms
- - b is a value of zero, one or two
- R 7 is (OCH 2 CH 2 )n or (OC 3 Hs)n radical where n has a value of one through ten,
- Rg is an alkyl group containing one to four carbon atoms
- d is a value of zero to three
- R9 is an alkoxy group containing one to four carbon atoms
- E is a value of zero to three
- - Rio is a amino, sulphur, epoxy, isocyanate, methacryloxy, alkyl, alkoxy, vinyl, phenyl, flouro or piperazinyl functional group,
- X " is chloride, bromide, fluoride, iodide, acetate, tosylate, sulphate, phosphate or other anion equivalent.
- 3-glycidoxypropyltriethoxysilane, 3-glycidoxypropylmethyldiethoxysilane, 3- glycidoxypropylmethyldimethoxysilane, 2-(3,4-epoxycyclohexyl)- ethyltrimethoxysilane, 2-(3,4-epoxycyclohexyl)-ethyltriethoxysilane can be used as epoxy functional alkoxy silane.
- Aminopropyltriethoxysilane, aminopropyltrimethoxysilane, aqueous 3- aminopropylsilane hydrolysate, bis[(3-triethoxysilyl)propyl]amine, bis[(3- trimethoxysilyl)propyl] amine can be used as amine functional alkoxy silane.
- 3-isocyanatepropyltrimethoxysilane, 3-isocyanatepropyltriethoxysilane can be used as isocyanate functional alkoxy silane.
- Methacryloxytrimethoxysilane 3-methacryloxypropyltrimethoxysilane, methacryloxypropyltriethoxysilane,
- methacryloxypropylmethyldiethoxysilane methacryloxymethyltrimethoxysilane, methacryloxymethyl(methyl)dimethoxysilane,
- methacryloxymethyl(methyl)diethoxysilane 3-acryloxypropyltrimethoxysilane can used as methacrylate functional alkoxy silane.
- Vinyltrimethoxysilane, vinyltriethoxysilane, vinyltris(2-methoxyethoxy) silane, vinyldimethylethoxysilane, vinylmetyhldiethoxysilane can be used as vinyl functional alkoxy silane.
- adherence of the silicon quaternized ammonium compound to mineral or organic structured surfaces and its hydrolytic stability are enhanced by using 3-glycidoxypropyltrimethoxysilane, 3- isocyanatepropyltriethoxysilane or aminoethlyaminepropyltrimethoxysilane which have epoxy, isocyanate or amine functions respectively.
- hydrophobicity of the compound is enhanced by means of alkyl functional n-octyltriethoxysilane.
- the alkyl functional alkoxy silane and the silicon quaternized ammonium compound enter into a second transesterification reaction in the presence of tin catalyst (dibutyl tin dilaurate), and at the end of the reaction alcohol is released.
- tin catalyst dibutyl tin dilaurate
- 3-glycidoxypropyltrimethoxysilane is used as the functional alkoxy silane, and the reaction of this compound with the silicon quaternized ammonium compound takes place as follows.
- Organosilicon surface protection material which is water soluble, and which thus does not harm the environment, is produced by means of the surface protection material production method (100) of the present invention.
- Water solubility of the material enables, in addition to ease of application, use thereof by being diluted with different proportions of water. This makes water insulation and surface protection applications more economical.
- the surface protection material produced by means of the method (100) of the present invention provides the properties of hydrolytic stability, adherence to the surface, hydrophobicity and antimicrobial properties to the surface to which it is applied by means of the functional group it comprises. Additionally, due to the fact that is it water soluble, it even penetrates into very small cracks and thereby changes surface morphology at nanometer level providing a higher level of surface protection. Thus it prevents mold and fungus formation on the inorganic surfaces to which it is applied.
Abstract
The present invention relates to a water soluble organosilicon (carbon and silicon based) surface protection material, which, upon being coated on inorganic and organic surfaces, enables protection of the surface against external factors and mold and fungus formation and provides water insulation; and a production method thereof comprising the steps of synthesizing alkoxy silane functional quaternized ammonium compound (101), subjecting the synthesized quaternized ammonium compound to transesterification reaction (102), functionalizing the transesterified quaternized ammonium compound with an alkoxy silane comprising a functional group (103).
Description
A SURFACE PROTECTION MATERIAL AND A PRODUCTION
METHOD THEREOF
Field of the Invention
The present invention relates to a water soluble organosilicon surface protection material, which, upon being coated on inorganic and organic surfaces, enables protection of the surface against external factors and mold and fungus formation and provides water insulation; and a production method thereof.
Background of the Invention
Commercially available surface protection coatings generally contain hydrocarbon solvents and are emulsified. Organosilicons containing alkyltrialkoxy have been used for water insulation and surface protection for many years.
In the state of the art, preparation of aqueous solutions of organosilicons containing quatemized amine group at room conditions is difficult and stability periods of aqueous solutions are fairly short.
The United States patent document no. US2008009644, an application in the state of the art, discloses a transesterified organosilicon composition developed to overcome this stability problem. The composition of this study is used on various inorganic, organic and cellulosic surfaces imparting water repellency to these surfaces. This patent document also discloses that Si-OCH3 is exchanged with glycol ether by the transesterification reaction. Similarly, the European patent document no. EP0552875, another document in the state of the art, discloses water repellant organosilicon containing quaternary ammonium.
However at the present time, costs of the production methods are very high and furthermore, the fact that ethanol, methanol and other hydrocarbons which are easily inflammable are used in application of organosilicon containing materials on surfaces causes safety problems.
Summary of the Invention
An objective of the present invention is to provide a water soluble organosilicon- based surface protection material.
Another objective of the present invention is to provide a surface protection material production method wherein transesterification process is performed for ensuring stability during preparation of aqueous solutions of organosilicons. A further objective of the present invention is to provide a surface protection material production method wherein a compound obtained by transesterification reaction is functionalized by being reacted with an alkoxy silane containing a functional group. Another objective of the present invention is to provide a surface protection material production method wherein, by carrying out the functionalization reaction in presence of a catalyst, production time is decreased, temperature and pressure values required for the reaction are decreased and thus costs are reduced. Another objective of the present invention is to provide a surface protection material production method wherein hydrophobicity and antimicrobial property, adherence to the surface and hydrolytic stability are provided to the material depending on the functional group that is added.
Detailed Description of the Invention
The surface protection material production method developed to fulfill the objective of the present invention is illustrated in the accompanying figure, in which;
Figure 1 is the view of the flowchart of the surface protection material production method. The surface protection material production method (100) developed to fulfill the objective of the present invention comprises the steps of
- synthesizing alkoxy silane functional quaternized ammonium compound (101),
- subjecting the synthesized quaternized ammonium compound to transesterification reaction (102),
- functionalizing the transesterified quaternized ammonium compound with an alkoxy silane comprising a functional group (103).
In the method (100) of the present invention, firstly a tertiary amine and an alkoxy silane are reacted in the presence of a catalyst and a solvent, and an alkoxy silane functional quaternized ammonium compound is obtained (101). In the preferred embodiment of the invention, methanol is used as the solvent and sodium iodide is used as the catalyst. In one embodiment of the invention, synthesis (101) of a 3- chloropropyltrimethoxysilane functional quaternized ammonium compound is performed by reaction of a tertiary amine and 3-chloropropyltrimethoxysilane.
The said reaction is as follows:
Sod
In one embodiment of the invention, the 3-chloropropyltrimethoxysilane functional quatemized ammonium obtained in step (101) is reacted with ethylene glycol and transesterification is performed (102). The said reaction is as follows:
In the last step, the silicon quaternized ammonium compound obtained in step (102) is functionalized by being reacted with a functional alkoxy silane (103). In the preferred embodiment of the invention; an alkyl, amine, epoxy, mercapto, methacrylate, vinyl, isocyanate or flouro functional alkoxy silane is used.
The silicon quaternized ammonium compound obtained as a result has the following formulation
Ri is an alkyl group containing one to four carbon atoms,
R2 is an alkyl group containing one to twenty two carbon atoms,
- -CH2C6H5,-CH2CH2OH and -(CH2)xNHC(0)Rvi wherein x has a value of from two to ten and RV1 is a perflluoroalkyl radical having one to twelve carbon atoms,
- R3 is an alkyl group containing one to twenty two carbon atoms,
R4 is an alkyl group containing one to four carbon atoms,
R5 is an alkyl group containing one to four carbon atoms,
a is a value of zero, one or two,
R6 is an alkoxy group containing one to four carbon atoms,
- b is a value of zero, one or two,
- a+b < 2,
R7 is (OCH2CH2)n or (OC3Hs)n radical where n has a value of one through ten,
- c = 3- (a+b),
- Rg is an alkyl group containing one to four carbon atoms,
d is a value of zero to three,
R9 is an alkoxy group containing one to four carbon atoms,
E is a value of zero to three,
- d+e < 3,
- Rio is a amino, sulphur, epoxy, isocyanate, methacryloxy, alkyl, alkoxy, vinyl, phenyl, flouro or piperazinyl functional group,
- f =3-(d-e),
X" is chloride, bromide, fluoride, iodide, acetate, tosylate, sulphate, phosphate or other anion equivalent. 3-glycidoxypropyltriethoxysilane, 3-glycidoxypropylmethyldiethoxysilane, 3- glycidoxypropylmethyldimethoxysilane, 2-(3,4-epoxycyclohexyl)- ethyltrimethoxysilane, 2-(3,4-epoxycyclohexyl)-ethyltriethoxysilane can be used as epoxy functional alkoxy silane.
Aminopropyltriethoxysilane, aminopropyltrimethoxysilane, aqueous 3- aminopropylsilane hydrolysate, bis[(3-triethoxysilyl)propyl]amine, bis[(3- trimethoxysilyl)propyl] amine can be used as amine functional alkoxy silane. 3-isocyanatepropyltrimethoxysilane, 3-isocyanatepropyltriethoxysilane can be used as isocyanate functional alkoxy silane.
Methacryloxytrimethoxysilane, 3-methacryloxypropyltrimethoxysilane, methacryloxypropyltriethoxysilane,
methacryloxypropyltris(trimethylsiloxy)silane,
methacryloxymethyltriethoxysilane,
methacryloxypropylmethyldimethoxysilane,
methacryloxypropylmethyldiethoxysilane, methacryloxymethyltrimethoxysilane, methacryloxymethyl(methyl)dimethoxysilane,
methacryloxymethyl(methyl)diethoxysilane, 3-acryloxypropyltrimethoxysilane can used as methacrylate functional alkoxy silane.
Heptadecafluorodecyltrimethoxysilane, (3,3,3- trifluoropropyl)methyldimethoxysilane, 3- perfluorooctylsulfonylaminopropyltriethoxysilane, (3,3,3- trifluoropropyl)methyldiethoxysilane, (3,3,3-trifluoropropyl)trimethoxysilane, (3,3,3-trifluoropropyl)triethoxysilane can be used as fluoro functional alkoxy silane.
N-decyltrimethoxysilane, n-decyltriethoxysilane, dodecyltrimethoxysilane, dodecyltriethoxysilane, dodecylmethyldimethoxysilane, hexadecyltrimethoxysilane, hexadecyltriethoxysilane, octodecyltrimethoxysilane, octodecyltriethoxysilane, octodecylmethyldimethoxysilane, n- octyltrimethoxysilane, n-octyltriethoxysilane, octylmethyldiethoxysilane, i- octyltrimethoxysilane, i-octyltriethoxysilane, propyltrimethoxysilane, propyltriethoxysilane, n-butyltrimethoxysilane, n-butyltriethoxysilane, i-
butyltrimethoxysilane, i-butyltriethoxysilane can be used as alkyl functional alkoxy silane.
Vinyltrimethoxysilane, vinyltriethoxysilane, vinyltris(2-methoxyethoxy) silane, vinyldimethylethoxysilane, vinylmetyhldiethoxysilane can be used as vinyl functional alkoxy silane.
Different properties can be provided to the compound depending on the functional group of the added alkoxy silane.
In one embodiment of the invention, adherence of the silicon quaternized ammonium compound to mineral or organic structured surfaces and its hydrolytic stability are enhanced by using 3-glycidoxypropyltrimethoxysilane, 3- isocyanatepropyltriethoxysilane or aminoethlyaminepropyltrimethoxysilane which have epoxy, isocyanate or amine functions respectively.
In another embodiment of the invention, hydrophobicity of the compound is enhanced by means of alkyl functional n-octyltriethoxysilane. The alkyl functional alkoxy silane and the silicon quaternized ammonium compound enter into a second transesterification reaction in the presence of tin catalyst (dibutyl tin dilaurate), and at the end of the reaction alcohol is released.
In another embodiment of the invention, 3-glycidoxypropyltrimethoxysilane is used as the functional alkoxy silane, and the reaction of this compound with the silicon quaternized ammonium compound takes place as follows.
Organosilicon surface protection material, which is water soluble, and which thus does not harm the environment, is produced by means of the surface protection material production method (100) of the present invention. Water solubility of the material enables, in addition to ease of application, use thereof by being diluted with different proportions of water. This makes water insulation and surface protection applications more economical.
In the said production method (100), reduction of the temperature and pres; values required for the reaction by means of use of catalyst also reduces costs.
The surface protection material produced by means of the method (100) of the present invention provides the properties of hydrolytic stability, adherence to the surface, hydrophobicity and antimicrobial properties to the surface to which it is applied by means of the functional group it comprises.
Additionally, due to the fact that is it water soluble, it even penetrates into very small cracks and thereby changes surface morphology at nanometer level providing a higher level of surface protection. Thus it prevents mold and fungus formation on the inorganic surfaces to which it is applied.
Claims
1. A surface protection material production method (100) comprising the steps of
- synthesizing alkoxy silane functional quaternized ammonium compound (101),
- subjecting the synthesized quaternized ammonium compound to transesterification reaction (102), and characterized by the step of
- functionalizing the transesterified quaternized ammonium compound with an alkoxy silane comprising a functional group (103).
2. A surface protection material production method (100) according to Claim 1, characterized by the step of synthesizing alkoxy silane functional quaternized ammonium compound (101) by reacting a tertiary amine and an alkoxy silane in the presence of a catalyst and a solvent.
3. A surface protection material production method (100) according to any one of the preceding claims, characterized by the step of synthesizing alkoxy silane functional quaternized ammonium compound (101) wherein methanol is used as the solvent and sodium iodide is used as the catalyst.
4. A surface protection material production method (100) according to any one of the preceding claims, characterized by the step of transesterification (102) wherein the synthesized alkoxy silane functional quaternized ammonium compound is reacted with glycol ether, the methoxy group within the compound is substituted by this glycol ether, and transesterified quaternized ammonium compound is obtained.
5. A surface protection material production method (100) according to any one of the preceding claims, characterized by the step of functionalizing the transesterified quaternized ammonium compound with an alkoxy
silane comprising a functional group (103), wherein silicon quaternized ammonium compound is obtained which has the following formulation
Ri is an alkyl group containing one to four carbon atoms,
R2 is an alkyl group containing one to twenty two carbon atoms,
- -CH2C6H5,-CH2CH2OH and -(CH2)xNHC(0)Rvi wherein x has a value of from two to ten and RV1 is a perflluoroalkyl radical having one to twelve carbon atoms,
R3 is an alkyl group containing one to twenty two carbon atoms,
R4 is an alkyl group containing one to four carbon atoms,
R5 is an alkyl group containing one to four carbon atoms,
a is a value of zero, one or two,
- R6 is an alkoxy group containing one to four carbon atoms,
b is a value of zero, one or two,
- a+b < 2,
R7 is (OCH2CH2)n or (OC3Hs)n radical where n has a value of one through ten,
- c = 3- (a+b),
Rg is an alkyl group containing one to four carbon atoms,
d is a value of zero to three,
R9 is an alkoxy group containing one to four carbon atoms,
E is a value of zero to three,
- d+e < 3,
Rio is an amino, sulphur, epoxy, isocyanate, methacryloxy, alkyl, alkoxy, vinyl, phenyl, flouro or piperazinyl functional group,
- f =3-(d-e),
X" is chloride, bromide, fluoride, iodide, acetate, tosylate, sulphate, phosphate or other anion equivalent.
6. A surface protection material production method (100) according to any one of the preceding claims, characterized by the step of functionalizing the transesterified silicon quaternized ammonium compound (103) by reacting it with an alkyl, amine, epoxy, mercapto, methacrylate, vinyl, isocyanate or flouro functional alkoxy silane.
7. A surface protection material production method (100) according to Claim 6, characterized by the step of functionalizing the transesterified quaternized ammonium compound with an alkoxy silane comprising a functional group (103), wherein 3-glycidoxypropyltriethoxysilane, 3- glycidoxypropylmethyldiethoxysilane, 3- glycidoxypropylmethyldimethoxysilane, 2-(3,4-epoxycyclohexyl)- ethyltrimethoxysilane or 2-(3,4-epoxycyclohexyl)-ethyltriethoxysilane is used as the epoxy functional alkoxy silane.
8. A surface protection material production method (100) according to Claim 6, characterized by the step of functionalizing the transesterified quaternized ammonium compound with an alkoxy silane comprising a functional group (103), wherein aminopropyltriethoxysilane, aminopropyltrimethoxysilane, aqueous 3-aminopropylsilane hydrolysate, bis [(3-triethoxysilyl)propyl] amine or bis [(3-trimethoxysilyl)propyl] amine is used as the amine functional alkoxy silane.
A surface protection material production method (100) according to Claim 6, characterized by the step of functionalizing the transesterified
quaternized ammonium compound with an alkoxy silane comprising a functional group (103), wherein 3-isocyanatepropyltrimethoxysilane or 3- isocyanatepropyltriethoxysilane is used as the isocyanate functional alkoxy silane.
10. A surface protection material production method (100) according to Claim 6, characterized by the step of functionalizing the transesterified quaternized ammonium compound with an alkoxy silane comprising a functional group (103), wherein methacryloxytrimethoxysilane, 3- methacryloxypropyltrimethoxysilane, 3- methacryloxypropyltriethoxysilane,
methacryloxypropyltris (trimethylsiloxy) silane,
methacryloxymethyltriethoxysilane, 3- methacryloxypropylmethyldimethoxysilane, 3- methacryloxypropylmethyldiethoxysilane,
methacryloxymethyltrimethoxysilane,
methacryloxymethyl(methyl)dimethoxysilane,
methacryloxymethyl(methyl)diethoxysilane or 3- acryloxypropyltrimethoxysilane is used as the methacrylate functional alkoxy silane.
11. A surface protection material production method (100) according to Claim 6, characterized by the step of functionalizing the transesterified quaternized ammonium compound with an alkoxy silane comprising a functional group (103), wherein heptadecafluorodecyltrimethoxysilane, (3,3,3-trifluoropropyl)methyldimethoxysilane, 3- perfluorooctylsulfonylaminopropyltriethoxysilane, (3,3,3- trifluoropropyl)methyldiethoxysilane, (3,3,3- trifluoropropyl)trimethoxysilane or (3,3,3-trifluoropropyl)triethoxysilane is used as the fluoro functional alkoxy silane.
12. A surface protection material production method (100) according to Claim 6, characterized by the step of functionalizing the transesterified quaternized ammonium compound with an alkoxy silane comprising a functional group (103), wherein n-decyltrimethoxysilane, n- decyltriethoxysilane, dodecyltrimethoxysilane, dodecyltriethoxysilane, dodecylmethyldimethoxysilane, hexadecyltrimethoxysilane, hexadecyltriethoxysilane, octodecyltrimethoxysilane, octodecyltriethoxysilane, octodecylmethyldimethoxysilane, n- octyltrimethoxysilane, n-octyltriethoxysilane, octylmethyldiethoxysilane, i-octyltrimethoxysilane, i-octyltriethoxysilane, propyltrimethoxysilane, propyltriethoxysilane, n-butyltrimethoxysilane, n-butyltriethoxysilane, i- butyltrimethoxysilane or i-butyltriethoxysilane is used as the alkyl functional alkoxy silane.
13. A surface protection material production method (100) according to Claim 6, characterized by the step of functionalizing the transesterified quaternized ammonium compound with an alkoxy silane comprising a functional group (103), wherein vinyltrimethoxysilane, vinyltriethoxysilane, vinyltris(2-methoxyethoxy)silane, vinyldimethylethoxysilane or vinylmetyhldiethoxysilane is used as the vinyl functional alkoxy silane.
14. A surface protection material production method (100) according to any one of Claims 7, 8 and 9, characterized by the step of functionalizing (103) wherein adherence to mineral and organic structured surfaces and hydrolytic stability of the silicon quaternized ammonium compound is enhanced by using 3-glycidoxypropyltrimethoxysilane, 3- isocyanatepropyltriethoxysilane or aminoethlyaminepropyltrimethoxysilane.
15. A surface protection material production method (100) according to Claim 12, characterized by the step of functionalizing (103) wherein hydrophobicity of silicon quaternized ammonium compound is enhanced by alkyl functional n-octyltriethoxysilane.
16. A carbon and silicon based (organosilicon) surface protection material, which is produced by means of the method according to any one of the preceding claims, and which is water soluble and thus does not harm the environment.
17. A surface protection material according to Claim 14, which provides the properties of hydrolytic stability, adherence to the surface, hydrophobicity and antimicrobial properties to the surface to which it is applied by means of the functional group it comprises.
18. A surface protection material according to any one of Claims 14 and 15, which, due to the fact that is it water soluble, even penetrates into very small cracks and thereby changes surface morphology at nanometer level and prevents mold and fungus formation.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3697860A4 (en) * | 2017-08-14 | 2021-08-25 | Interphase Materials Inc. | Surface treatment |
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| US20080009644A1 (en) | 2006-07-07 | 2008-01-10 | Zydex Industries | Organosilicon Compounds |
| US20080181862A1 (en) * | 2007-01-08 | 2008-07-31 | Ndsu Research Foundation | Quaternary ammonium functionalized cross-linked polyalkylsiloxanes with anti-fouling activity |
| EP2439223A1 (en) * | 2010-10-11 | 2012-04-11 | BYK-Chemie GmbH | Copolymers containing polysiloxane groups with epoxy/amine as main structure and their use |
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2013
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| EP0552875A2 (en) | 1992-01-23 | 1993-07-28 | Dow Corning Corporation | Water repellents containing organosilicon compounds |
| DE19928127C1 (en) * | 1999-06-19 | 2000-05-31 | Clariant Gmbh | Production of antimicrobial formulation containing known and new trialkoxysilanyl-substituted quaternary ammonium compounds useful for treatment of surfaces e.g. textiles, glass, metals and plastics |
| EP1288246A1 (en) * | 2001-08-14 | 2003-03-05 | Wacker-Chemie GmbH | Organopolysiloxanes with quaternary ammonium groups and preparation method |
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