GB2496708A - Solvent-borne scratch resistant coating compositions containing polymetallosiloxanes - Google Patents
Solvent-borne scratch resistant coating compositions containing polymetallosiloxanes Download PDFInfo
- Publication number
- GB2496708A GB2496708A GB1211240.5A GB201211240A GB2496708A GB 2496708 A GB2496708 A GB 2496708A GB 201211240 A GB201211240 A GB 201211240A GB 2496708 A GB2496708 A GB 2496708A
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- United Kingdom
- Prior art keywords
- text
- solvent
- silicone resin
- metal
- thermoplastic
- 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.)
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- 239000000203 mixture Substances 0.000 title claims abstract description 40
- 239000006120 scratch resistant coating Substances 0.000 title claims description 3
- 238000000576 coating method Methods 0.000 claims abstract description 37
- 229920002050 silicone resin Polymers 0.000 claims abstract description 31
- 229910052751 metal Inorganic materials 0.000 claims abstract description 25
- 239000002184 metal Substances 0.000 claims abstract description 25
- 239000011248 coating agent Substances 0.000 claims abstract description 24
- -1 IIIA Group element Inorganic materials 0.000 claims abstract description 20
- 229920001169 thermoplastic Polymers 0.000 claims abstract description 19
- 239000002904 solvent Substances 0.000 claims abstract description 17
- 239000004416 thermosoftening plastic Substances 0.000 claims abstract description 17
- 229910052796 boron Inorganic materials 0.000 claims abstract description 14
- 229920001971 elastomer Polymers 0.000 claims abstract description 14
- 239000005060 rubber Substances 0.000 claims abstract description 14
- 229920001187 thermosetting polymer Polymers 0.000 claims abstract description 13
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000000463 material Substances 0.000 claims abstract description 12
- 239000000376 reactant Substances 0.000 claims abstract description 11
- 229910052710 silicon Inorganic materials 0.000 claims abstract description 11
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims abstract description 9
- 238000005299 abrasion Methods 0.000 claims abstract description 9
- 238000000034 method Methods 0.000 claims abstract description 9
- 229920000620 organic polymer Polymers 0.000 claims abstract description 9
- 239000010703 silicon Substances 0.000 claims abstract description 9
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 claims abstract description 8
- 150000002739 metals Chemical class 0.000 claims abstract description 6
- 239000003960 organic solvent Substances 0.000 claims abstract description 6
- SCPYDCQAZCOKTP-UHFFFAOYSA-N silanol Chemical compound [SiH3]O SCPYDCQAZCOKTP-UHFFFAOYSA-N 0.000 claims abstract description 6
- 229910052718 tin Inorganic materials 0.000 claims abstract description 6
- 239000004327 boric acid Substances 0.000 claims abstract description 5
- 230000007704 transition Effects 0.000 claims abstract description 5
- 229910052726 zirconium Inorganic materials 0.000 claims abstract description 5
- 238000002360 preparation method Methods 0.000 claims abstract description 4
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 claims abstract description 3
- 150000003839 salts Chemical class 0.000 claims abstract description 3
- 239000000758 substrate Substances 0.000 claims description 20
- BOTDANWDWHJENH-UHFFFAOYSA-N Tetraethyl orthosilicate Chemical group CCO[Si](OCC)(OCC)OCC BOTDANWDWHJENH-UHFFFAOYSA-N 0.000 claims description 8
- 235000010338 boric acid Nutrition 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 229910015444 B(OH)3 Inorganic materials 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- BFXIKLCIZHOAAZ-UHFFFAOYSA-N methyltrimethoxysilane Chemical compound CO[Si](C)(OC)OC BFXIKLCIZHOAAZ-UHFFFAOYSA-N 0.000 claims description 3
- CPUDPFPXCZDNGI-UHFFFAOYSA-N triethoxy(methyl)silane Chemical compound CCO[Si](C)(OCC)OCC CPUDPFPXCZDNGI-UHFFFAOYSA-N 0.000 claims description 3
- JKWMSGQKBLHBQQ-UHFFFAOYSA-N diboron trioxide Chemical compound O=BOB=O JKWMSGQKBLHBQQ-UHFFFAOYSA-N 0.000 claims description 2
- ZHXTWWCDMUWMDI-UHFFFAOYSA-N dihydroxyboron Chemical compound O[B]O ZHXTWWCDMUWMDI-UHFFFAOYSA-N 0.000 claims description 2
- 230000003647 oxidation Effects 0.000 claims description 2
- 238000007254 oxidation reaction Methods 0.000 claims description 2
- 102220347004 c.89G>A Human genes 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 26
- 229920005989 resin Polymers 0.000 description 16
- 239000011347 resin Substances 0.000 description 16
- 239000011521 glass Substances 0.000 description 14
- 239000000243 solution Substances 0.000 description 14
- 229920000642 polymer Polymers 0.000 description 12
- 239000004417 polycarbonate Substances 0.000 description 11
- 229920000515 polycarbonate Polymers 0.000 description 7
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 239000004698 Polyethylene Substances 0.000 description 4
- 239000004743 Polypropylene Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- XECAHXYUAAWDEL-UHFFFAOYSA-N acrylonitrile butadiene styrene Chemical compound C=CC=C.C=CC#N.C=CC1=CC=CC=C1 XECAHXYUAAWDEL-UHFFFAOYSA-N 0.000 description 3
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 3
- 239000004676 acrylonitrile butadiene styrene Substances 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000003822 epoxy resin Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
- 239000012994 photoredox catalyst Substances 0.000 description 3
- 229920000647 polyepoxide Polymers 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 239000010936 titanium Substances 0.000 description 3
- 229910052719 titanium Inorganic materials 0.000 description 3
- YEYKMVJDLWJFOA-UHFFFAOYSA-N 2-propoxyethanol Chemical compound CCCOCCO YEYKMVJDLWJFOA-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- 244000043261 Hevea brasiliensis Species 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 229910002808 Si–O–Si Inorganic materials 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 2
- TUVYSBJZBYRDHP-UHFFFAOYSA-N acetic acid;methoxymethane Chemical compound COC.CC(O)=O TUVYSBJZBYRDHP-UHFFFAOYSA-N 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 229920003052 natural elastomer Polymers 0.000 description 2
- 229920001194 natural rubber Polymers 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
- 229920001155 polypropylene Polymers 0.000 description 2
- 229920001296 polysiloxane Polymers 0.000 description 2
- 239000011550 stock solution Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 229920005992 thermoplastic resin Polymers 0.000 description 2
- 229910052723 transition metal Inorganic materials 0.000 description 2
- 150000003624 transition metals Chemical class 0.000 description 2
- 229920006337 unsaturated polyester resin Polymers 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- 229910015446 B(OCH3)3 Inorganic materials 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- 229910002923 B–O–B Inorganic materials 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 229920002292 Nylon 6 Polymers 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 229910008048 Si-S Inorganic materials 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- 229910006336 Si—S Inorganic materials 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 229940043232 butyl acetate Drugs 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000008199 coating composition Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 239000006184 cosolvent Substances 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- OLLFKUHHDPMQFR-UHFFFAOYSA-N dihydroxy(diphenyl)silane Chemical group C=1C=CC=CC=1[Si](O)(O)C1=CC=CC=C1 OLLFKUHHDPMQFR-UHFFFAOYSA-N 0.000 description 1
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 229940093499 ethyl acetate Drugs 0.000 description 1
- 235000019439 ethyl acetate Nutrition 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 229960004279 formaldehyde Drugs 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 229910052733 gallium Inorganic materials 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000006459 hydrosilylation reaction Methods 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- 229910052909 inorganic silicate Inorganic materials 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 229910052752 metalloid Inorganic materials 0.000 description 1
- 150000002738 metalloids Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229920003986 novolac Polymers 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- PARWUHTVGZSQPD-UHFFFAOYSA-N phenylsilane Chemical compound [SiH3]C1=CC=CC=C1 PARWUHTVGZSQPD-UHFFFAOYSA-N 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000004626 polylactic acid Substances 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000003014 reinforcing effect Effects 0.000 description 1
- 229910052706 scandium Inorganic materials 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 125000005372 silanol group Chemical class 0.000 description 1
- 229910052990 silicon hydride Inorganic materials 0.000 description 1
- 229920005573 silicon-containing polymer Polymers 0.000 description 1
- 235000015096 spirit Nutrition 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- AJSTXXYNEIHPMD-UHFFFAOYSA-N triethyl borate Chemical compound CCOB(OCC)OCC AJSTXXYNEIHPMD-UHFFFAOYSA-N 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/02—Polysilicates
-
- 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
- C09D183/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers
- C09D183/14—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers in which at least two but not all the silicon atoms are connected by linkages other than oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/12—Polysiloxanes containing silicon bound to hydrogen
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/14—Polysiloxanes containing silicon bound to oxygen-containing groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
- C08J7/04—Coating
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
- C08J7/12—Chemical modification
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
- C08L83/02—Polysilicates
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
- C08L83/04—Polysiloxanes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
- C08L83/04—Polysiloxanes
- C08L83/06—Polysiloxanes containing silicon bound to oxygen-containing groups
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- 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
- C09D183/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers
- C09D183/02—Polysilicates
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- 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
- C09D183/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers
- C09D183/04—Polysiloxanes
-
- 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
- C09D183/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers
- C09D183/04—Polysiloxanes
- C09D183/06—Polysiloxanes containing silicon bound to oxygen-containing groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/48—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule in which at least two but not all the silicon atoms are connected by linkages other than oxygen atoms
- C08G77/56—Boron-containing linkages
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/48—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule in which at least two but not all the silicon atoms are connected by linkages other than oxygen atoms
- C08G77/58—Metal-containing linkages
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Abstract
The invention provides a method for the preparation of a solvent-borne silicone resin containing polymetallosiloxane, wherein a metal containing material is hydrolysed and condensed with a silicon containing reactant in a solvent that the polymetallosiloxane and the silicon containing reactant at least are soluble in. The metal is chosen from Transition Group metals, IIIA Group element, Zr or Sn, and the metal containing material is preferably at least one boron containing material selected from boric acid or an of its salts, boron anhydride, boronic acid, alkoxyborate or a mixture thereof. The silicon containing reactant is preferably an alkoxysilane, hydroxysilan, alkoxysiloxane or hydroxysiloxane, and the solvent is an organic solvent. The solvent-borne silicone resin itself is claimed as well as its use in a thermoplastic or thermosetting organic polymer or rubbers or blends thereof in the enhancement of the scratch and/or abrasion resistance of the composition or coating.
Description
SOLVENT-BORNE SCRATCH RESISTANT COATING COMPOSITIONS CONTAINING
POLYBOROSILOXAN ES
[0001] The invention relates to siUcone resins comprising metallosUoxane which contains Si-S 0-Metal bonds or borosiloxane containing Si-0-B bonds and potentially Si-O-Si and/or B-O-B bonds. It also relates to the preparation of such silicone resins and to their use in thermoplastic or thermosetting organic polymer or rubber or thermoplastic/rubber blends compositions to enhance scratch and/or abrasion resistance of the organic polymer compositions. It further relates to coatings made of such sUicone resins for scratch resistance enhancement.
BACKGROUND
[0002] W02008/018981 discloses silicone polymers containing boron, aluminum and/or titanium, and having silicon-bonded branched alkoxy groups.
(0003] US2O1O!01 91001 discloses a process for performing hydrolysis and condensation of an epoxy-functional silane with boric acid, the condensate formed in the reaction being based on Si-O-B and/or Si-O-Si bonds.
[0004] US4152509 discloses borosiloxane polymers produced by heating at least one of boric acid compound with phenylsilane to effect polycondensation reaction.
(0005] EP141727361 discloses a coating composition formed from linear, reactive polysiloxanes and the reaction with two additional components including a reactant and a boron containing compound.
(0006] US 20100316876 describes a borosiloxane adhesive which is said to have high resistance to moisture, high transparency, and excellent adhesion to various substrates. The borosiloxane adhesive is derived from an alkenyl functional borosiloxane, a silicon-hydride compound and a hydrosilylation catalyst.
SUMMARY OF THE INVENTION
[0007] The invention provides a method for the preparation of a solvent-borne silicone resin containing polymetaUosloxane, wherein
S
a. A Metal containing material whose Metal M is chosen from Transition Group metals, lIlA Group elements, Zr and Sn b. A silicon containing reactant which is an alkoxysilane or hydroxysilane or alkoxysiloxane or hydroxysUoxane are hydrolysed and condensed in the presence of a solvent that dissolves the polymetallosiloxane and the silicon containing reactant to form rnetallosiloxane Si-O-M bonds.
[0008] Metals M as defined herein encompass transition metals (Sc, Ti, V, Cr, Mn, Fe, Co, Ni, Cu, Zn and all elements from Group lIlA (i.e. B, Al, Ga. In and TI), Zr and Sn. This comprises boron, the first element of Group lIlA which is in fact a metalloid instead of a metal.
Nevertheless for the sake of convenience boron is considered to be a Metal M in the rest of the present specification. Preferably the Metal M is chosen from Period 4 of the transition metals.
Preferably the Metal M is chosen from nickel, copper and zinc. In other preferred embodiments, the Metal M is chosen from boron, titanium and aluminum.
[0009] Preferably, the silicone resin contains boron. While borosiloxane structures or other Metal containing structures are known, most rely on in-situ reaction of a siloxane with boron particulates. No prior art suggests a solvent-borne silicone resin specifically able to improve scratch resistance when applied as a coating.
[0010] The silicone resin preferably contains T units; D; M and/orG units. The resin is characterized by a majority of successive Si-O-M units where the Si is selected from R3SiO1 (M' units), R2SiO2, (D units), RSiO3, (T units) and SiO4 (0 units). The resin further contains polyorganosiloxanes, also known as silicones, generally comprising repeating siloxane units selected from R3SiO112 (M' units), R25i0212 (ID units), RSiO3 (1 units) and SO4Q (0 units), in which each R represents an organic group or hydrogen or a hydroxyl group. Branched silicone resins contain I and/or 0 units, optionally in combination with M' and/or D units, are preferred.
In the branched silicone resins of the invention, at least 25% of the siloxane units are preferably T and/orG units. More preferably, at least 75% of the siloxane units in the branched silicone resin are T andfor 0 units.
[0011] Preferably, the Metal containing material is at least one boron containing material selected from (F) boric acid of the formula B(OH)3, any of its salts or boric anhydride, (ii) boronic acid of the formula Ri B(OH)2, (iii) alkoxyborate of formulae B(0R2)3 or Ri B(0R2)2, a mixture containing at least two or more of (I), (ii) or (iii), where Ri and R2 are independently alkyl, alkenyl, aryl or arylakyl substituents. More preferably, the boron containing material is trimethoxyborane or triethoxyborane.
[0012) Preferably, the Metal containing material has general formula M(R3)m where m ri7 depending on the oxidation state of the considered Metal, selected from i alkoxymetals where R3=OR' and R' is an alkyl group, ii metal hydroxyl where R3=OH.
[0013] Preferably, the solvent is an organic solvent. A solvent as defined herein is a liquid substance that dissolves the polymetallosiloxane and the silicon containing reactant (alkoxysilane or hydroxysilane or alkoxysiloxane or hydroxysiloxane). The metal containing reactant might not be soluble in that solvent, such as B(OH)3. The solvent can be either pure substances like ether or ethanol or mixtures, such as the paraffinic solvents such as the various petroleum ethers and white spirits, or the range of pure or mixed aromatic solvents obtained from petroleum or tar fractions. The solvent can be for example methanol, ethanol, propanol, butanol. formic acid, acetic acid, formamide, acetone, tetrahydrofuran, methyl ethyl ketone, ethylacetate, acetonitrile, dimethylformamide, dimethylsulfoxide, hexane. benzene, diethyl ether.
methylene chloride, carbon tetrachloride, butylacetate, etc. [0014) In preferred embodiments, the solvent is ethanol. This is cheap, readily available and able to dissolve the polymetallosiloxane produced as well as the silicon containing reactant.
Preferably, propyl glycol methyl ether acetate (PGMEA) is added during the synthesis as a cosolvent.
[0015] The invention further provides a solvent-borne silicone resin comprising at east one polymetallosiloxane which contains Si-D-M bonds whose Metal M is chosen from Transition Group metals, lIlA Group elements and Sn, at least one solvent that can dissolve the polymetallosiloxane. Preferably, the molar ratio of Metal atom to Si atom ranges from 0.01 to 6, S preferably 0.1 to 2.
(0016] In a possible synthesis approach, alkoxysiloxane or hydroxysiloxane resins can be used as raw material, provided they can be dissolved in a solvent. Monoalkoxysilanes or hydroxysilanes when hydrolysed and condensed will form M' groups in the silicone resin and dialkoxysilanes when hydrolysed and condensed will form D groups in the silicone resin. A monoalkoxysilane or dialkoxysilane can be reacted with trialkoxysilanes and/or tetraalkoxysilanes to form a branched silicone resin.
[0017] The ailcoxysilane or hydroxysilane is preferably selected from i) tetra(alkoxysilane) Si(0R3)4, (ii) trialkoxysilane R6S1(0R3)3, (iii) dialkoxysilane R6RTSi(0R3)2 or (iv) monoalkoxysilane R6R7R8SiOR3, a mixture containing two or more of (i), (ii), (Ui) or (iv), where R3 is aOl to 010 alkyl group and R6, R7 and RB are independently alkyl, alkenyl, aryl, arylalkyl, bearing or not organic functionalities such as but not limited to glycidoxy, methacryloxy, acryloxy, and R is an alkyl group. Example of suitable hydroxysilane is diphenyl(dihydroxy)silane. A tetra(alkoxysilane) readily available and which can be used in the present invention is tetraethyl orthosilicate TEOS. In other preferred embodiments, trialkoxysilane like methyltriethoxysilane or methyltrimethoxysilane is used, which can be mixed or not with tetra(alkoxysilane) like TEOS.
[0018] Addition of water during the synthesis is possible but not required. Water loading is calculated minimum to consume partially the alkoxies and preferably the whole alkoxies present in the system. Preferably, the whole mixture is refluxed at a temperature preferably ranging from to 160°C in the presence or not of an organic solvent. Then the alcohol and organic solvent are stripped and possible remaining water are distilled off from the resin through, for example, azeotropic mixture water! alcohol. The obtained product can be further dried under vacuum at high temperature (ranging from 50 to 100°C) to remove remaining traces of solvents, alcohols or water. These resins can be used as additives in polymers or coatings formulations to improve scratch and/or abrasion resistance.
[0019] The invention keeps to a certain extent the transparency of the host matrix, i.e. the new resin allows to keep the transparency of the polymer it is blended with or the coating made up with the resin is transparent.
S
[0020] The silicone resins of the invention can be blended with a wide range of thermoplastic resins, for example polycarbonates, ABS (acrylonitrile butadiene styrene) resins, polycarbonatelABS blends, polyesters, polystyrene, or polyolefins such as polypropylene or polyethylene. The silicone resins of the invention can also be blended with thermosetting resins, for example epoxy resins of the type used in electronics applications, which are subsequently thermoset, or unsaturated polyester resin.
[0021] The thermoplastic polymer can be chosen from the carbonate family (e.g. Polycarbonate PC), polyamides (e.g. Polyamide 6 and 6.6), polyester (e.g. polyethyleneterephtalate). The thermoplastic polymer can be chosen from the polyoletin family (e.g. polypropylene PP or polyethylene PE).The thermoplastic resin can be a bio-sourced thermoplastic rnatrice such as polylactic acid (PLA) or polyhydroxybutadiene (PHB) or bio-sourced PP or PE. The polymer can be chosen from thermoplastic! rubbers blends from the family of natural rubber or Acrylonitrile / styrene 1 butadiene ABS. The polymer can be chosen from rubber made of a diene, preferably natural rubber. The polymer can be chosen from thermoset from the Novolac family (phenol-formol) or epoxy resin.
[0022] These above polymers can optionally be reinforced with, for example, glass fibres.
Applications include but are not limited to transportation vehicles, construction, electrical application, printed circuits boards and textiles. Unsaturated polyester resins, or epoxy are moulded for use in, for example, the nacelle of wind turbine devices. Normally, they are reinforced with glass (or carbon) fibre cloth.
[0023] The silicone resins of the invention frequently have further advantages including but not limited to transparency, higher impact strength, toughness, increased adhesion between two surfaces, increased surface adhesion, scratch and/or abrasion resistance and improved tensile and flexural mechanical properties. The resins can be added to polymer compositions to improve mechanical properties such as impact strength, toughness and tensile, flexural mechanical properties and scratch and/or abrasion resistance. The resins can be used to treat reinforcing fibres used in polymer matrices to improve adhesion at the fibre polymer interface.
The resins can be used at the surface of polymer compositions to improve adhesion to paints.
The resins can be used to form coatings on a substrate.
S
[0024] The silicone resins of the invention can for example be present in thermoplastic or thermoset or rubber or thermoplasticlrubber blends organic polymer compositions or in blend of thermoplastic or blend of thermoset in amounts ranging from 0.1 or 0.5% by weight up to 50 or 75%. Preferred amounts may range from 0.1 to 25% by weight silicone resin in thermoplastic compositions such as polycarbonates, and from 0.2 to 75% by weight in thermosetting compositions such as epoxy resins.
[0025] The invention also provides the use of a silicone resin as defined herein above as a fire-or scratch-andlor abrasion resistant coating on a substrate. The substrate can be for example, a polymer like polycarbonate or an inorganic substrate like glass.
(0026] The invention further provides a thermoplastic or thermoset or rubber or thermoplastic!rubber blends organic polymer composition comprising a thermoplastic or thermoset organic polymer and a silicone resin as defined herein above.
EXAMPLES
[0027] Scratch resistance test is non-standard. Steel wool (000') was pressed against the substrate (-1.5Kg force) and scratch back and forth for 200 cycles. Make visual observation of the coating surface. Rating: excellent means no scratch, good means a few scratch (hardly seen), poor means many scratches (surface hazy).
Example I
[0028] 106.6g tetraethyl orthosilicate (TEOS) was mixed with 108.7g ethanol and 23.Og 0.03 M HCI. H20/Si = 2.5. The whole was stirred at Room Temperature for 65 hours. This mixture solution was denoted as solution A and used as a stock solution.
Example 2
[0029] Drop-casted solution A on glass substrate. A clear hard coating was formed after dry at ST for 24hrs. The coating was heat treated at 120°C for 10-20 minutes. Scratch resistance was poor.
Example 3
[0030] 11.9g solution A and 0.90g B(OMe)3 i.e. B(OCH3)3 were mixed at RI. BISF-1/3. The mixture was aged 24 hrs at RT. Drop casted a coating on glass substrate. A clear hard coating was formed after dry at RI for 24hrs. The coating was heat treated at 120°C for 10-20 minutes.
Scratch resistance was excellent.
Example 4
[0031] 11.9g solution A and 0.53g B(OMe)3 were mixed at PT. BlSh---115. The mixture was aged 24 hrs at RT. Drop casted a coating on glass substrate, A clear hard coating was formed after dry at RT for 24hrs. The coating was heat treated at 120°C for 10-20 minutes. Scratch resistance was excellent.
Example 5
[0032] 1 05.4g methyltrimethoxysilane was mixed with 111.4g ethanol, 20.9g H20, and 2.Og acetic acid. H20/Si = 1.5. the whole was stirred at RI for 71 hours. This mixture solution was denoted as solution B and used as a stock solution.
Example 6
[0033] Solution B was drop-casted on glass substrate. A clear hard coating was formed after dry at ST for 24hrs. The coating was heat treated at 120°C for 10-20 minutes. Scratch resistance was poor.
Example 7
[0034] 12.Og solution B and 4.Og B(CMe)3 were mixed at RT. B1Si---1/3. The mixture was aged 1-24 hrs at RT. Drop casted coatings on glass substrate. Clear hard coating was formed after thy at RT for 24hrs. The coating was heat treated at 120°C for 10-20 minutes. Scratch resistance was good.
Example B
(0035] 12.Og solution Band 2.42g B(OMe)3 were mixed at RT. B(Si=-1/5. The mixture was aged 1-24 hrs at RT. Drop casted coatings on glass substrate. A clear hard coating was formed after dry at RT for 24hrs. The coating was heat treated at 120°C for 10-20 minutes. Scratch resistance was good.
Example 9
[0036] 207.89 tetraethyl orthosilicate was mixed with 108.Og ethanol, 9.Og 0.1 M HCI, and 27.Og H20. H2OtSi =2.0. The whole was stirred at RT for 17 hours. Then added 25.88g B(OMe)3. B/Si = %. Then it was stirred at RI for 5 his. 50 g propyl glycol methyl ether acetate (PGMEA) was added, the solution was drop-casted on polycarbonate and glass substrates.
Clear hard coatings were formed after dry at RI for 24hrs. The coatings were heat treated at 120°C for 10-20 minutes. Scratch resistance was excellent for both coatings on PC and glass substrates.
Example 10
(0037] 156.25 g tetraethyl orthosilicate and I 33.73g methyltriethoxysilane were mixed with 144.99g ethanol, 13.5g 0.1 M HCI, and 40.5g H20. H20/Si = 2.0. It was stirred at RT for 6 hours. Then 38.97g B(OMe)3 were added. B/Si = 1A. The whole was stirred at RT for 17 hrs. 40 g propyl glycol methyl ethei acetate (PGMEA) was added, the solution was drop-casted on polycarbonate and glass substrates. Clear hard coatings were formed after dry at RI for 24hrs.
The coatings were heat treated at 120°C for 10-20 minutes. Scratch resistance was excellent for bath coatings on PC and glass substrates.
Example 11
[0038] 12.Og DC 2403 resin (methyl T)was mixed with 12.09 ethanol, 050g 0.025 MHCI, and 1.7g B(OH)3, stir at RI for 24 hrs, formed a clear solution. Ihe solution was drop-casted on polycarbonate and glass substrates. Clear hard coatings were formed after dry at RI tor 24hrs.
The coating was heat treated at 120°C for 10-20 minutes. Scratch resistance was excellent for both coatings on PC and glass substrates.
Claims (2)
- <claim-text>CLAIMS1. Method for the preparation of a solvent-borne silicone resin containing polymetallosiloxane, wherein a. A Metal containing material whose Metal M is chosen from Transition Group metals, lilA Group elements, Zr and Sn b. A silicon containing reactant which is an alkoxysilane or hydroxysilane or alkoxysiloxane or hydroxysiloxane are hydrolysed and condensed in the presence of a solvent that dissolves the polymetallosiloxane and the silicon containing reactant to form metallosiloxane Si-O-M bonds.</claim-text> <claim-text>2. Method according to claim 1 wherein the Metal containing material is at least one boron containing material selected from (i) boric acid of the formula B(OH)3, any of its salts or boric anhydride, (H) boronic acid of the formula Si B(OH)2, (Vi) aikoxyborate of formula B(0R2)3 or R1B(0R2)2, a mixture containing at least two or more of (I), (ii) or (Hi), where Si and 52 are independently alkyl, alkenyl, aryl or arylalkyl substituents.</claim-text> <claim-text>3. Method according to claim 1 wherein the Metal containing material has the general formula M(R3)m where m =17 depending on the oxidation state of the considered Metal, selected from alkoxymetals where R3OR' and R' is an alkyl group, ii metal hydroxyl where R30H.</claim-text> <claim-text>4. The method according to any of claims 1 to 3 wherein an alkoxysilane is used.</claim-text> <claim-text>5. The method according to claim 4 wherein the alkoxysilane is tetraethyl orthosilicate, methyltriethoxysilane or methyltrimethoxysilane or a mixture of them.</claim-text> <claim-text>6. The method according to any of claims Ito 5 wherein the solvent is an organic solvent.</claim-text> <claim-text>7. A solvent-borne silicone resin comprising a. at least one polymetaflosiloxane which contains Si-O-M bonds whose Metal M is chosen from Transition Group metals, lIlA Group elements, Zr and Sn, b. at least one solvent that can dissolve the polymetallosiloxane.</claim-text> <claim-text>8. The silicone resin according to claim 7 which contains T units; D; M' and/or Q units.</claim-text> <claim-text>9. The silicone resin according to claim 7 or 8 wherein the Metal M is boron.</claim-text> <claim-text>10. The silicone resin according to any of claims 7 to 9 wherein the molar ratio of Metal atom to Si atom ranges from 0.01 to 6, preferably 0.1 to
- 2.</claim-text> <claim-text>11. The silicone resin according to any of claims ito 10 wherein the solvent is an organic solvent.</claim-text> <claim-text>12. Use of the silicone resin as claimed in any of claims 7 to 11 in a thermoplastic or thermosetting organic polymer or rubbers or thermoplastic! rubbers blends composition to enhance scratch and/or abrasion resistance of the composition.</claim-text> <claim-text>13. Use of a silicone resin as claimed in any of claims 7 to 11 as a scratch resistant coating on a substrate.</claim-text> <claim-text>14. A thermoplastic or thermoset organic polymer or rubbers or thermoplastic / rubbers blends composition comprising a thermoplastic or thermoset organic polymer or rubbers or thermoplastic / rubbers blends and a silicone resin as claimed in any of claims 7to II.</claim-text> <claim-text>15. A scratch and!or abrasion resistant coating on a substrate wherein the coating comprises a silicone resin according to any of claims 7 to 11.</claim-text> <claim-text>16. A scratch and/or abrasion resistant coating according to claim 15 wherein the coating is transparent.</claim-text>
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
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| US201161560829P | 2011-11-17 | 2011-11-17 |
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| GB201211240D0 GB201211240D0 (en) | 2012-08-08 |
| GB2496708A true GB2496708A (en) | 2013-05-22 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1211240.5A Withdrawn GB2496708A (en) | 2011-11-17 | 2012-06-25 | Solvent-borne scratch resistant coating compositions containing polymetallosiloxanes |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113845684A (en) * | 2021-09-15 | 2021-12-28 | 安徽坤涂新材料科技有限公司 | Production process of wear-resistant PC glass plate |
| CN118460104A (en) * | 2024-05-08 | 2024-08-09 | 常州市武进虹灵化工有限公司 | Boron modified organic silicon resin high-temperature-resistant coating and preparation method thereof |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4152509A (en) * | 1976-09-30 | 1979-05-01 | The Foundation: The Research Institute For Special Inorganic Materials | Borosiloxane polymers and a method for producing the same |
| EP0327311A2 (en) * | 1988-02-02 | 1989-08-09 | Hitachi Chemical Co., Ltd. | A coating fluid for forming an oxide coating |
| WO2008018981A2 (en) * | 2006-08-04 | 2008-02-14 | Dow Corning Corporation | Silicone resin and silicone composition |
| US20100125123A1 (en) * | 1999-08-04 | 2010-05-20 | Lichtenhan Joseph D | Metallized nanostructured chemicals as cure promoters |
-
2012
- 2012-06-25 GB GB1211240.5A patent/GB2496708A/en not_active Withdrawn
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4152509A (en) * | 1976-09-30 | 1979-05-01 | The Foundation: The Research Institute For Special Inorganic Materials | Borosiloxane polymers and a method for producing the same |
| EP0327311A2 (en) * | 1988-02-02 | 1989-08-09 | Hitachi Chemical Co., Ltd. | A coating fluid for forming an oxide coating |
| US20100125123A1 (en) * | 1999-08-04 | 2010-05-20 | Lichtenhan Joseph D | Metallized nanostructured chemicals as cure promoters |
| WO2008018981A2 (en) * | 2006-08-04 | 2008-02-14 | Dow Corning Corporation | Silicone resin and silicone composition |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113845684A (en) * | 2021-09-15 | 2021-12-28 | 安徽坤涂新材料科技有限公司 | Production process of wear-resistant PC glass plate |
| CN113845684B (en) * | 2021-09-15 | 2022-11-29 | 安徽坤涂新材料科技有限公司 | Production process of wear-resistant PC glass plate |
| CN118460104A (en) * | 2024-05-08 | 2024-08-09 | 常州市武进虹灵化工有限公司 | Boron modified organic silicon resin high-temperature-resistant coating and preparation method thereof |
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| Publication number | Publication date |
|---|---|
| GB201211240D0 (en) | 2012-08-08 |
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