CN101508852B - Glass-hard organosilicon protective coating, preparation and uses thereof - Google Patents
Glass-hard organosilicon protective coating, preparation and uses thereof Download PDFInfo
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- CN101508852B CN101508852B CN2009100380090A CN200910038009A CN101508852B CN 101508852 B CN101508852 B CN 101508852B CN 2009100380090 A CN2009100380090 A CN 2009100380090A CN 200910038009 A CN200910038009 A CN 200910038009A CN 101508852 B CN101508852 B CN 101508852B
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- 239000011253 protective coating Substances 0.000 title claims abstract description 14
- 238000002360 preparation method Methods 0.000 title claims abstract description 10
- -1 hydroxyalkyl acrylate Chemical compound 0.000 claims abstract description 30
- 239000000203 mixture Substances 0.000 claims abstract description 25
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims abstract description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 12
- 229910052710 silicon Inorganic materials 0.000 claims abstract description 11
- 239000010703 silicon Substances 0.000 claims abstract description 11
- 229910052751 metal Inorganic materials 0.000 claims abstract description 6
- 239000002184 metal Substances 0.000 claims abstract description 6
- 230000001681 protective effect Effects 0.000 claims abstract description 6
- 125000003158 alcohol group Chemical group 0.000 claims abstract description 4
- 238000005538 encapsulation Methods 0.000 claims abstract description 4
- 239000011521 glass Substances 0.000 claims abstract description 4
- 239000004033 plastic Substances 0.000 claims abstract description 4
- 229920003023 plastic Polymers 0.000 claims abstract description 4
- 239000004567 concrete Substances 0.000 claims abstract description 3
- 239000004575 stone Substances 0.000 claims abstract description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- CERQOIWHTDAKMF-UHFFFAOYSA-N alpha-methacrylic acid Natural products CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 16
- BFXIKLCIZHOAAZ-UHFFFAOYSA-N methyltrimethoxysilane Chemical compound CO[Si](C)(OC)OC BFXIKLCIZHOAAZ-UHFFFAOYSA-N 0.000 claims description 14
- 125000005395 methacrylic acid group Chemical group 0.000 claims description 13
- 238000002444 silanisation Methods 0.000 claims description 12
- 239000000463 material Substances 0.000 claims description 10
- GILMNGUTRWPWSY-UHFFFAOYSA-N 2-hydroxypropyl prop-2-enoate;2-methylprop-2-enoic acid Chemical compound CC(=C)C(O)=O.CC(O)COC(=O)C=C GILMNGUTRWPWSY-UHFFFAOYSA-N 0.000 claims description 9
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 8
- YYLGKUPAFFKGRQ-UHFFFAOYSA-N dimethyldiethoxysilane Chemical compound CCO[Si](C)(C)OCC YYLGKUPAFFKGRQ-UHFFFAOYSA-N 0.000 claims description 8
- CPUDPFPXCZDNGI-UHFFFAOYSA-N triethoxy(methyl)silane Chemical compound CCO[Si](C)(OCC)OCC CPUDPFPXCZDNGI-UHFFFAOYSA-N 0.000 claims description 8
- YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical compound CO[SiH](OC)OC YUYCVXFAYWRXLS-UHFFFAOYSA-N 0.000 claims description 8
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 7
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 7
- 229910000077 silane Inorganic materials 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- SBRXLTRZCJVAPH-UHFFFAOYSA-N ethyl(trimethoxy)silane Chemical compound CC[Si](OC)(OC)OC SBRXLTRZCJVAPH-UHFFFAOYSA-N 0.000 claims description 6
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 6
- 150000003377 silicon compounds Chemical class 0.000 claims description 6
- DENFJSAFJTVPJR-UHFFFAOYSA-N triethoxy(ethyl)silane Chemical compound CCO[Si](CC)(OCC)OCC DENFJSAFJTVPJR-UHFFFAOYSA-N 0.000 claims description 6
- LDHQCZJRKDOVOX-UHFFFAOYSA-N 2-butenoic acid Chemical compound CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 claims description 5
- SXPLZNMUBFBFIA-UHFFFAOYSA-N butyl(trimethoxy)silane Chemical compound CCCC[Si](OC)(OC)OC SXPLZNMUBFBFIA-UHFFFAOYSA-N 0.000 claims description 5
- XQSFXFQDJCDXDT-UHFFFAOYSA-N hydroxysilicon Chemical compound [Si]O XQSFXFQDJCDXDT-UHFFFAOYSA-N 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- 239000003921 oil Substances 0.000 claims description 5
- KMNCBSZOIQAUFX-UHFFFAOYSA-N 2-ethoxy-1,2-diphenylethanone Chemical group C=1C=CC=CC=1C(OCC)C(=O)C1=CC=CC=C1 KMNCBSZOIQAUFX-UHFFFAOYSA-N 0.000 claims description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 4
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 claims description 4
- 239000012965 benzophenone Substances 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 4
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 229920002545 silicone oil Polymers 0.000 claims description 4
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Natural products CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 claims description 3
- PXLDRBQDIXLCEK-UHFFFAOYSA-N C(=O)P(C1=CC=CC=C1)(C1=CC=CC=C1)=O.CC1=CC=CC=C1 Chemical compound C(=O)P(C1=CC=CC=C1)(C1=CC=CC=C1)=O.CC1=CC=CC=C1 PXLDRBQDIXLCEK-UHFFFAOYSA-N 0.000 claims description 3
- BDAHDQGVJHDLHQ-UHFFFAOYSA-N [2-(1-hydroxycyclohexyl)phenyl]-phenylmethanone Chemical compound C=1C=CC=C(C(=O)C=2C=CC=CC=2)C=1C1(O)CCCCC1 BDAHDQGVJHDLHQ-UHFFFAOYSA-N 0.000 claims description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Substances CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 3
- XGZGKDQVCBHSGI-UHFFFAOYSA-N butyl(triethoxy)silane Chemical compound CCCC[Si](OCC)(OCC)OCC XGZGKDQVCBHSGI-UHFFFAOYSA-N 0.000 claims description 3
- SCPWMSBAGXEGPW-UHFFFAOYSA-N dodecyl(trimethoxy)silane Chemical compound CCCCCCCCCCCC[Si](OC)(OC)OC SCPWMSBAGXEGPW-UHFFFAOYSA-N 0.000 claims description 3
- 230000000694 effects Effects 0.000 claims description 3
- 230000007062 hydrolysis Effects 0.000 claims description 3
- 238000006460 hydrolysis reaction Methods 0.000 claims description 3
- MSRJTTSHWYDFIU-UHFFFAOYSA-N octyltriethoxysilane Chemical compound CCCCCCCC[Si](OCC)(OCC)OCC MSRJTTSHWYDFIU-UHFFFAOYSA-N 0.000 claims description 3
- 229960003493 octyltriethoxysilane Drugs 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 238000000576 coating method Methods 0.000 abstract description 21
- 239000011248 coating agent Substances 0.000 abstract description 20
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract description 9
- 150000001875 compounds Chemical class 0.000 abstract description 8
- 239000000758 substrate Substances 0.000 abstract description 2
- 239000000919 ceramic Substances 0.000 abstract 1
- 239000007888 film coating Substances 0.000 abstract 1
- 238000009501 film coating Methods 0.000 abstract 1
- 239000002023 wood Substances 0.000 abstract 1
- 238000003756 stirring Methods 0.000 description 11
- 239000007788 liquid Substances 0.000 description 9
- 238000001723 curing Methods 0.000 description 8
- 238000002329 infrared spectrum Methods 0.000 description 6
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 5
- 238000010521 absorption reaction Methods 0.000 description 5
- 238000009835 boiling Methods 0.000 description 5
- 239000002609 medium Substances 0.000 description 5
- 239000003973 paint Substances 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 4
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 4
- 229910052753 mercury Inorganic materials 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical compound [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 0.000 description 4
- 102100026735 Coagulation factor VIII Human genes 0.000 description 3
- 101000911390 Homo sapiens Coagulation factor VIII Proteins 0.000 description 3
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 3
- 229910018557 Si O Inorganic materials 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 238000002454 metastable transfer emission spectrometry Methods 0.000 description 3
- LIVNPJMFVYWSIS-UHFFFAOYSA-N silicon monoxide Inorganic materials [Si-]#[O+] LIVNPJMFVYWSIS-UHFFFAOYSA-N 0.000 description 3
- 238000010792 warming Methods 0.000 description 3
- QNODIIQQMGDSEF-UHFFFAOYSA-N (1-hydroxycyclohexyl)-phenylmethanone Chemical compound C=1C=CC=CC=1C(=O)C1(O)CCCCC1 QNODIIQQMGDSEF-UHFFFAOYSA-N 0.000 description 2
- KWVGIHKZDCUPEU-UHFFFAOYSA-N 2,2-dimethoxy-2-phenylacetophenone Chemical compound C=1C=CC=CC=1C(OC)(OC)C(=O)C1=CC=CC=C1 KWVGIHKZDCUPEU-UHFFFAOYSA-N 0.000 description 2
- VHSHLMUCYSAUQU-UHFFFAOYSA-N 2-hydroxypropyl methacrylate Chemical compound CC(O)COC(=O)C(C)=C VHSHLMUCYSAUQU-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000008199 coating composition Substances 0.000 description 2
- 230000006837 decompression Effects 0.000 description 2
- 230000007812 deficiency Effects 0.000 description 2
- 238000004134 energy conservation Methods 0.000 description 2
- 238000009413 insulation Methods 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 239000013307 optical fiber Substances 0.000 description 2
- 238000000016 photochemical curing Methods 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 230000005855 radiation Effects 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- JMXKSZRRTHPKDL-UHFFFAOYSA-N titanium ethoxide Chemical group [Ti+4].CC[O-].CC[O-].CC[O-].CC[O-] JMXKSZRRTHPKDL-UHFFFAOYSA-N 0.000 description 2
- VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 description 2
- 230000007704 transition Effects 0.000 description 2
- PWBHRVGYSMBMIO-UHFFFAOYSA-M tributylstannanylium;acetate Chemical compound CCCC[Sn](CCCC)(CCCC)OC(C)=O PWBHRVGYSMBMIO-UHFFFAOYSA-M 0.000 description 2
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 1
- RIWRBSMFKVOJMN-UHFFFAOYSA-N 2-methyl-1-phenylpropan-2-ol Chemical compound CC(C)(O)CC1=CC=CC=C1 RIWRBSMFKVOJMN-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- 206010020751 Hypersensitivity Diseases 0.000 description 1
- 229910002656 O–Si–O Inorganic materials 0.000 description 1
- 206010034972 Photosensitivity reaction Diseases 0.000 description 1
- 229910002808 Si–O–Si Inorganic materials 0.000 description 1
- DPDMMXDBJGCCQC-UHFFFAOYSA-N [Na].[Cl] Chemical compound [Na].[Cl] DPDMMXDBJGCCQC-UHFFFAOYSA-N 0.000 description 1
- 238000007171 acid catalysis Methods 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 208000026935 allergic disease Diseases 0.000 description 1
- 230000007815 allergy Effects 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- 238000005815 base catalysis Methods 0.000 description 1
- 238000004891 communication Methods 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013530 defoamer Substances 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000007599 discharging Methods 0.000 description 1
- 239000002612 dispersion medium Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000003628 erosive effect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 230000002650 habitual effect Effects 0.000 description 1
- 231100000652 hormesis Toxicity 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- PSGAAPLEWMOORI-PEINSRQWSA-N medroxyprogesterone acetate Chemical compound C([C@@]12C)CC(=O)C=C1[C@@H](C)C[C@@H]1[C@@H]2CC[C@]2(C)[C@@](OC(C)=O)(C(C)=O)CC[C@H]21 PSGAAPLEWMOORI-PEINSRQWSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229920001558 organosilicon polymer Polymers 0.000 description 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
- 239000000123 paper Substances 0.000 description 1
- 230000000149 penetrating effect Effects 0.000 description 1
- 230000036211 photosensitivity Effects 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920006254 polymer film Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000006748 scratching Methods 0.000 description 1
- 230000002393 scratching effect Effects 0.000 description 1
- 239000000565 sealant Substances 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000009941 weaving Methods 0.000 description 1
Landscapes
- Paints Or Removers (AREA)
Abstract
The invention relates to a high-hardness organic silicon protective coating, a preparation method and the application thereof. The coating consists of the following components based on the parts by weight: 100 parts of component A, 0-900 parts of component B and 0.05-5 parts of component C; wherein, the component A consists of silanized or oligomeric-siliconized (methyl) hydroxyalkyl acrylate and silicon functional organosilicone compound, proportion by weight between the silanized or oligomeric-siliconized (methyl) hydroxyalkyl acrylate and silicon functional organosilicone compound is 100-10 : 0-90; component B is alcohol or the mixture of alcohol and water; and component C is photoinitiator. The components are coated on the surface of a substrate after being evenly mixed, and a lyophobic anticorrosive film with good stick force is prepared after the coating is irradiated by ultraviolet light; the hardness of a film coating pencil is larger than or equal to 6H, so that the coating has good surface protective property and wear resisting property. The invention can be applicable to surface lyophobic protective treatment of stone, ceramics, concrete, metope, glass, metal, wood and plastic as well as cultural relic protection or surface encapsulation of electronic components.
Description
Technical field
The present invention relates to paint field, particularly a kind of glass-hard organosilicon protective coating and its production and application.
Background technology
Organosilicon material has excellent hydrophobic nature, resistant of high or low temperature, weathering resistance, erosion resistance, electric insulating quality, radiation resistance, flame retardant resistance and biocompatibility, being widely used in fields such as aerospace, building, electronic apparatus, defence and military, weaving, petrochemical complex, medicine, food-processing, daily-use chemical industry, is requisite high-tech material in the national economy all departments.Organosilicon coating is one of industrial application form of fast development wherein just, is widely used as buildings waterproof moisture-proof coating, electrical apparatus insulation protective cover, joint sealant protective cover, metal anti-corrosive paint, high-temperature resistant coating, weather-resistant coating, antiseized release coating, radiation resistant coating etc.Organosilicon coating can be divided into organic solvent type, no-solvent type and aq. type by dispersion medium, organic solvent type commonly used exists foaming, contaminate environment, shortcoming such as inflammable, there is the high deficiency of viscosity in no-solvent type, and then there are problems such as water tolerance, adhesive power and low contamination resistance in present aq. type coating.Because Si-O-Si in the polysiloxane, O-Si-O bond angle are big, molecular chain is submissive, and surface energy is little, and the glass transition temperature Tg of polymkeric substance is low, so organosilicon coating ubiquity hardness low (pencil hardness is below 2～3H), shortcoming such as intensity is little and adhesive power is low.
Ultraviolet-curing paint is a kind of coating of environment-friendly and energy-efficient, it has does not have or low VOC discharging, energy-conservation, advantage such as curing speed is fast, production efficiency is high, be fit to streamline production, solidification value is low, fields such as chemical industry, machinery, electronics, light industry, communication have been widely used in developed country, not only used in a large number at timber, metal, plastics, paper, leather, and on materials such as optical fiber, printed circuit plate, electronic devices and components encapsulation successful Application.The vinyl monomer that ultraviolet-curing paint is commonly used mainly contains polyester type (methyl) esters of acrylic acid, epoxy type (methyl) esters of acrylic acid, polyurethane-type (methyl) esters of acrylic acid in the market, these used main component oligopolymer of ultraviolet-curing paint generally all have higher viscosity, when coating, must add thinner to regulate its viscosity and rheological, and promotion film forming and curing, improve the performance of cured film etc., the thinner that is added comprises reactive monomer, organic solvent and other polyfunctional group (methyl) esters of acrylic acid etc.But habitual at present (methyl) esters of acrylic acid reactive thinner or linking agent have stronger hormesis to eyes, and skin contact also easily causes allergy, influences the healthy of operator.
The ultraviolet curing type organosilicon material has excellent physics and chemical property, curing speed is fast, can not need organic solvent, be particularly suitable for heat sensitive occasion is used, applied research mainly concentrates on from aspects such as shape coating, optical fiber coatings, printed-wiring board (PWB) conformal coating or moisture-proof coating, semi-conductive coating, electronic package material, planography, mould materials, but also ubiquity intensity difference, shortcoming such as hardness is little, sticking power is little.
Summary of the invention
The objective of the invention is to overcome the deficiency that prior art exists, a kind of ultraviolet light polymerization glass-hard organosilicon protective coating is provided.
Another object of the present invention provides a kind of preparation method of ultraviolet light polymerization glass-hard organosilicon protective coating, will be composite modified with it with the good silicoorganic compound of photosensitivity organosilicon oligopolymer consistency, can improve the flowability of composition, significantly improve the organosilyl hardness of photocuring, intensity and sticking power again, reduce the stimulation and the infringement of other reactive thinner.
Glass-hard organosilicon protective coating of the present invention, it is composed as follows: by weight, be made up of for 0.05～5 part 100 parts of A components, 0～900 part of B component, C component; Wherein the A component is silanization or oligosiloxaneization (methyl) acrylic acid hydroxy alkyl ester and functionalized silicon organic silicon compound composition, and its weight ratio is 100～10: 0～90; The B component is alcohol or alcohol-water mixture; The C component is a light trigger.
The preparation method of glass-hard organosilicon protective coating of the present invention solidifies above-mentioned each component to obtain after mixing under 15～50 ℃ under action of ultraviolet light.
Described alcohol is ethanol, propyl alcohol, Virahol or their mixture.
Described light trigger is Benzoin ethyl ether, α, alpha, alpha-dimethyl oxygen base-α-phenyl methyl phenyl ketone DMPA (Irgacure 651), 2-hydroxy-2-methyl-1-phenyl-1-acetone HMPP (Darocur 1173), 1-hydroxyl-cyclohexyl benzophenone HCPK (Irgacure 184), benzophenone, 2,4,6-Three methyl Benzene formyl diphenyl phosphine oxide TPO or two aryl phosphine oxide compound BAPO (Irgacure 819DW), the commercial disignation of this material of textual representation in the bracket.
Described functionalized silicon organic silicon compound is a Union carbide A-162, methyltrimethoxy silane, ethyl triethoxysilane, ethyl trimethoxy silane, propyl-triethoxysilicane, propyl trimethoxy silicane, the butyl triethoxyl silane, butyl trimethoxy silane, octyltri-ethoxysilane, the octyl group Trimethoxy silane, the dodecyl Trimethoxy silane, dimethyldiethoxysilane, dimethyldimethoxysil,ne, gamma-methyl allyl acyloxypropyl trimethoxysilane, gamma-methyl allyl acyloxypropyl three (trimethylsiloxy group) silane, γ-An Bingjisanyiyangjiguiwan, the low polycondensate of γ-glycidoxypropyltrime,hoxysilane and above-mentioned one or more silane, or hydroxy silicon oil, containing hydrogen silicone oil, or their mixture.
Described silanization or oligosiloxaneization (methyl) acrylic acid hydroxy alkyl ester is prepared by following method:
The many organoalkoxysilanes of (methyl) acrylic acid hydroxy alkyl ester and alkyl or many alkoxyl groups of alkyl oligosiloxane react under the effect at catalyzer below 20～80 ℃ with 100: 50～300 part by weight and prepared in 4～24 hours;
The many organoalkoxysilanes of wherein said alkyl are methyltrimethoxy silane, ethyl triethoxysilane, ethyl trimethoxy silane, dimethyldiethoxysilane, dimethyldimethoxysil,ne or propyl trimethoxy silicane; Described many alkoxyl groups of alkyl oligosiloxane is aforementioned one or more the low polycondensate of hydrolysis of the many organoalkoxysilanes of alkyl, and its Siliciumatom number is 2～10; Oligosiloxane can dealcoholysis under acid or base catalysis makes by many organoalkoxysilanes of alkyl and water the low viscosity polycondensate;
Wherein said (methyl) acrylic acid hydroxy alkyl ester is one or more the mixture in methacrylic acid-beta-hydroxy ethyl ester, methacrylic acid-β-hydroxypropyl acrylate, senecioate-hydroxyl ethyl ester, senecioate-hydroxyl ethyl ester, monomethyl vinylformic acid condensed ethandiol ester, the single vinylformic acid condensed ethandiol ester;
Wherein said catalyzer is organotin or titanic acid ester or their mixture, and addition is 0.1%～7% of (methyl) acrylic acid hydroxy alkyl ester weight; Organotin can be stannous octoate, dibutyl tin laurate or tributyl tin acetate; Titanic acid ester can be tetraethyl titanate, titanium isopropylate or tetra-n-butyl titanate;
And prove conclusively above-mentioned (methyl) acrylic acid hydroxy alkyl ester by following characteristic infrared spectrum data and realized silanization or oligosiloxaneization: C=C absorption peak (1640cm
-1Near), C=O absorption peak (1730cm
-1Near), Si-O absorption peak (1000～1200cm
-1).
In order further to improve the workability of coating composition, also can suitably add the auxiliary agent or the fillers such as defoamer, flow agent and promotor of trace.
Glass-hard organosilicon protective coating of the present invention not only has the characteristics of organosilicon polymer, coating composition has lower viscosity, good mobile penetrating quality, and the photocuring transparent polymer second-order transition temperature Tg that obtains is very high, coating have high rigidity (〉=6H), good adhesion performance and resistance toheat.Method of the present invention also has energy-conservation and quick-setting characteristics, has broad application prospects at the aspects such as surface encapsulation of the surface hydrophobicity protective treatment of stone material, pottery, concrete, metope, glass, metal, timber, plastics etc. and historical relic's protection, electronic devices and components.
Embodiment
The invention will be further described below in conjunction with specific embodiment, but the present invention is not limited in following embodiment.
Embodiment 1: the preparation of silanization methacrylic acid-beta-hydroxy ethyl ester
In 250 milliliters there-necked flask, add 32.5g methacrylic acid-beta-hydroxy ethyl ester (HEMA) and 44.5g methyltrimethoxy silane (MTMS), stir, the stannous octoate that adds 0.5g, stirred 24 hours under the room temperature, underpressure distillation then, remove the lower boiling micromolecular compound, get a transparent low-viscosity (mobile) liquid, identify that through infrared spectra IR it is silanization methacrylic acid-beta-hydroxy ethyl ester (spectral data: tangible absorption peak-COO-(1730cm
-1Near), C=C (1640cm
-1Near), Si-O (1000～1200cm
-1)).
Embodiment 2: the preparation of silanization methacrylic acid-β-hydroxypropyl acrylate
Methacrylic acid-β-hydroxypropyl acrylate (HPMA) 28.8g, Union carbide A-162 (MTES) 35.6g, stannous octoate 0.5g are mixed, and stirring at room is warming up to 70～75 ℃ after 1 hour, be incubated 4 hours.The lower boiling micromolecular compound is removed in underpressure distillation then, gets a transparent low-viscosity (mobile) liquid.Gained infrared spectra diagram data is similar to embodiment 1.
Embodiment 3: the preparation of oligosiloxane methacrylic acid-β-hydroxypropyl acrylate
The Polymethoxylated oligosiloxane of hydrolytie polycondensation thing methyl (MTMS low-shrinkage polycondensate with methacrylic acid-β-hydroxypropyl acrylate (HPMA) 38g and methyltrimethoxy silane, the low viscosity transparent liquid) 56.5g adds in 250 milliliters the there-necked flask, mix, adding di-n-butyltin dilaurate 0.1g under the room temperature stirred 24 hours, underpressure distillation then, remove the lower boiling micromolecular compound, get a transparent low-viscosity (mobile) liquid, identify that through infrared spectra IR it is oligosiloxane methacrylic acid-β-hydroxypropyl acrylate (infrared spectrum data: tangible absorption peak-COO-(1730cm
-1Near), C=C (1640cm
-1Near), Si-O (1000～1200cm
-1)).
Embodiment 4: the preparation of oligosiloxane methacrylic acid-beta-hydroxy ethyl ester
Raw material is methacrylic acid-beta-hydroxy ethyl ester 26g, the Polymethoxylated oligosiloxane 78g of methyl, and as catalyzer, other reaction conditions is with embodiment 3 with tetra-n-butyl titanate 1.5g.The infrared spectrum data are similar to embodiment 3.
Embodiment 5
Is a low-viscosity (mobile) liquid with the low polycondensate of 10g silanization methacrylic acid-beta-hydroxy ethyl ester (embodiment 1) and 10g KH570 (gamma-methyl allyl acyloxypropyl trimethoxysilane), 70g MTMS, 5g hydroxy silicon oil, 5g KH560 (γ-epoxypropyl Trimethoxy silane) and 0.8g light trigger TPO stirring at room after evenly, get its 10g sample and brush, under 1 kilowatt medium pressure mercury lamp UV-light, shone 3 minutes then.The relevant performance data that records sees Table 1.
Embodiment 6
30g silanization methacrylic acid-beta-hydroxy ethyl ester (embodiment 1) is even with 25g KH570,2g KH550 (γ-An Bingjisanyiyangjiguiwan), the low polycondensate of 25g MTES (Union carbide A-162), 18g containing hydrogen silicone oil and light trigger benzophenone 2.5g stirring at room, get a low viscosity transparent liquid, get its 10g sample and brush, under UV-light, shone 5 minutes then.The relevant performance data that records sees Table 1.
Embodiment 7
Two aryl phosphine oxide compound Irgacure 819DW mix with 15g oligosiloxane methacrylic acid-β-hydroxypropyl acrylate (embodiment 3) and 5g KH570,10g TTMSPM (gamma-methyl allyl acyloxypropyl three (trimethylsiloxy group) silane), 50g MTMS, 15g BTMS (butyl trimethoxy silane), 5g DMDES (dimethyldiethoxysilane) and 500g Virahol, 400g water and 1.5g light trigger, 40 ℃ of following stirrings are got its 100g sample after 8 hours and are brushed, and shine 2 minutes under UV-light after 2 hours.The relevant performance data that records sees Table 1.
Embodiment 8
35g oligosiloxane methacrylic acid-beta-hydroxy ethyl ester (embodiment 4) is mixed with 5g KH560 (γ-glycidoxypropyltrime,hoxysilane), 50g MTES, 10g hydroxy silicon oil and 100g ethanol and 0.8g light trigger Darocur 1173,40 ℃ of following stirrings were got its 20g sample in 8 hours and are brushed, and shone 3 minutes under UV-light after half an hour.The relevant performance data that records sees Table 1.
Embodiment 9
The low polycondensate 34g of HEMA32.5g and MTMS joined in 250 milliliters the there-necked flask, mix, add stannous octoate 0.1g and titanium isopropylate 0.5g stirring 24 hours under the room temperature, get a transparent low-viscosity (mobile) liquid oligosiloxane methacrylic acid-beta-hydroxy ethyl ester (infrared data is similar to embodiment 3).Get its 10g, add the light trigger Irgacure651 of 20mg, brush after stirring at room is even, under 1 kilowatt medium pressure mercury lamp UV-light, shone 4 minutes then.The relevant performance data that records sees Table 1.
Embodiment 10
HEMA 26g and MTMS 27.2g joined in 250 milliliters the there-necked flask, mix, adding dibutyl tin laurate 0.2g under the room temperature stirred 12 hours, be warming up to 60～65 ℃ then, drip the HEMA of 26g, insulation reaction 6 hours, low-boiling compound is removed in decompression then, gets a transparent liquid silicon alkanisation methacrylic acid-beta-hydroxy ethyl ester (infrared data is similar to embodiment 3).Get its 5g, add the light trigger Irgacure 184 of 2.5g octyl group Trimethoxy silane, 2.5g KH570 and ethanol 49g, water 1g and 30mg, brush after stirring at room is even, under 1 kilowatt medium pressure mercury lamp UV-light, shone 3 minutes then.The relevant performance data that records sees Table 1.
Embodiment 11
Propyl trimethoxy silicane (PTMS) mixed at room temperature of monomethyl vinylformic acid one condensed ethandiol ester 34.8g and 32.8g is even, the tributyl tin acetate that adds 0.15g, be warming up to 70～75 ℃ of reactions 6 hours under stirring, cooling then, low-boiling compound is removed in decompression, gets transparent liquid silicon alkanisation monomethyl vinylformic acid one a condensed ethandiol ester (infrared data is similar to embodiment 3).Get its 8g, add the light trigger Benzoin ethyl ether of 1g KH570,1gMTMS and ethanol 19.5g, water 0.5g and 0.4g, brush after stirring at room is even, under 1 kilowatt medium pressure mercury lamp UV-light, shone 3 minutes then.The relevant performance data that records sees Table 1.
Some experiment test results that table 1: embodiment 5～11 photocureable polymers are filmed
The testing method of above-mentioned performance is as follows:
The transparency: leave standstill and observed the transparency in one day;
Water contact angle: measure water droplet and stopped on the film surface 1 minute
StaticContact angle;
Pencil hardness: by the pencil hardness (scratching) behind the GB/T6739-1996 measurement curing of coating;
Sticking power: by film sticking power on different substrate materials (unorganic glass, polished tile, monolithic metal, transite plate, plank) of GB/T1720-1989 measurement;
Chemical reagent resistance: (Party A's method of 3% sodium-chlor is adopted in the resistance to salt water test to the chemical reagent resistance of filming by the GB1763-79 measurement, and the medium of resistance to acids and bases is the sulfuric acid of 0.1mol/L and the sodium hydroxide of 0.1mol/L; Soak time is 3 days);
Tg: with the second-order transition temperature of differential scanning instrument test polymer film.
Claims (5)
1. a glass-hard organosilicon protective coating is characterized in that: by weight, be made up of for 0.05～5 part 100 parts of A components, 0～900 part of B component, C component; Wherein the A component is silanization or oligosiloxaneization (methyl) acrylic acid hydroxy alkyl ester and functionalized silicon organic silicon compound composition, and its weight ratio is 100～10: 0～90; The B component is alcohol or alcohol-water mixture; The C component is a light trigger;
Described silanization or oligosiloxaneization (methyl) acrylic acid hydroxy alkyl ester is prepared by following method: the many organoalkoxysilanes of (methyl) acrylic acid hydroxy alkyl ester and alkyl or many alkoxyl groups of alkyl oligosiloxane react under the effect at catalyzer under 20～80 ℃ of temperature with 100: 50～300 part by weight and prepared in 4～24 hours; The many organoalkoxysilanes of described alkyl are methyltrimethoxy silane, ethyl triethoxysilane, ethyl trimethoxy silane, dimethyldiethoxysilane, dimethyldimethoxysil,ne or propyl trimethoxy silicane; Described many alkoxyl groups of alkyl oligosiloxane is aforementioned one or more the low polycondensate of hydrolysis of the many organoalkoxysilanes of alkyl, and its Siliciumatom number is 2～10; Described (methyl) acrylic acid hydroxy alkyl ester is one or more the mixture in methacrylic acid-beta-hydroxy ethyl ester, methacrylic acid-β-hydroxypropyl acrylate, senecioate-hydroxyl ethyl ester, senecioate-hydroxyl ethyl ester, monomethyl vinylformic acid condensed ethandiol ester, the single vinylformic acid condensed ethandiol ester; Described catalyzer is organotin or titanic acid ester or their mixture, and addition is 0.1%～7% of (methyl) acrylic acid hydroxy alkyl ester weight;
Described functionalized silicon organic silicon compound is a Union carbide A-162, methyltrimethoxy silane, ethyl triethoxysilane, ethyl trimethoxy silane, propyl-triethoxysilicane, propyl trimethoxy silicane, the butyl triethoxyl silane, butyl trimethoxy silane, octyltri-ethoxysilane, the octyl group Trimethoxy silane, the dodecyl Trimethoxy silane, dimethyldiethoxysilane, dimethyldimethoxysil,ne, gamma-methyl allyl acyloxypropyl trimethoxysilane, gamma-methyl allyl acyloxypropyl three (trimethylsiloxy group) silane, γ-An Bingjisanyiyangjiguiwan, the low polycondensate of γ-glycidoxypropyltrime,hoxysilane and above-mentioned one or more silane, hydroxy silicon oil, a kind of or any several mixture in the containing hydrogen silicone oil.
2. a kind of glass-hard organosilicon protective coating according to claim 1 is characterized in that: described alcohol is ethanol, propyl alcohol, Virahol or their mixture; Described light trigger is Benzoin ethyl ether, α, alpha, alpha-dimethyl oxygen base-α-phenyl methyl phenyl ketone, 2-hydroxy-2-methyl-1-phenyl-1-acetone, 1-hydroxyl-cyclohexyl benzophenone, benzophenone, 2,4,6-Three methyl Benzene formyl diphenyl phosphine oxide or two aryl phosphine oxide compound.
3. the preparation method of the described a kind of glass-hard organosilicon protective coating of claim 1, it is characterized in that: by weight, 100 parts of A components, 0～900 part of B component, C component mix under 15～50 ℃ for 0.05～5 part; Wherein the A component is silanization or oligosiloxaneization (methyl) acrylic acid hydroxy alkyl ester and functionalized silicon organic silicon compound composition, and its weight ratio is 100～10: 0～90; The B component is alcohol or alcohol-water mixture; The C component is a light trigger;
Described silanization or oligosiloxaneization (methyl) acrylic acid hydroxy alkyl ester is prepared by following method: the many organoalkoxysilanes of (methyl) acrylic acid hydroxy alkyl ester and alkyl or many alkoxyl groups of alkyl oligosiloxane react under the effect at catalyzer under 20～80 ℃ of temperature with 100: 50～300 part by weight and prepared in 4～24 hours; The many organoalkoxysilanes of described alkyl are methyltrimethoxy silane, ethyl triethoxysilane, ethyl trimethoxy silane, dimethyldiethoxysilane, dimethyldimethoxysil,ne or propyl trimethoxy silicane; Described many alkoxyl groups of alkyl oligosiloxane is aforementioned one or more the low polycondensate of hydrolysis of the many organoalkoxysilanes of alkyl, and its Siliciumatom number is 2～10; Described (methyl) acrylic acid hydroxy alkyl ester is one or more the mixture in methacrylic acid-beta-hydroxy ethyl ester, methacrylic acid-β-hydroxypropyl acrylate, senecioate-hydroxyl ethyl ester, senecioate-hydroxyl ethyl ester, monomethyl vinylformic acid condensed ethandiol ester, the single vinylformic acid condensed ethandiol ester; Described catalyzer is organotin or titanic acid ester or their mixture, and addition is 0.1%～7% of (methyl) acrylic acid hydroxy alkyl ester weight;
Described functionalized silicon organic silicon compound is a Union carbide A-162, methyltrimethoxy silane, ethyl triethoxysilane, ethyl trimethoxy silane, propyl-triethoxysilicane, propyl trimethoxy silicane, the butyl triethoxyl silane, butyl trimethoxy silane, octyltri-ethoxysilane, the octyl group Trimethoxy silane, the dodecyl Trimethoxy silane, dimethyldiethoxysilane, dimethyldimethoxysil,ne, gamma-methyl allyl acyloxypropyl trimethoxysilane, gamma-methyl allyl acyloxypropyl three (trimethylsiloxy group) silane, γ-An Bingjisanyiyangjiguiwan, the low polycondensate of γ-glycidoxypropyltrime,hoxysilane and above-mentioned one or more silane, hydroxy silicon oil, a kind of or any several mixture in the containing hydrogen silicone oil.
4. the preparation method of a kind of glass-hard organosilicon protective coating according to claim 3, it is characterized in that: described alcohol is ethanol, propyl alcohol, Virahol or their mixture; Described light trigger is Benzoin ethyl ether, α, alpha, alpha-dimethyl oxygen base-α-phenyl methyl phenyl ketone, 2-hydroxy-2-methyl-1-phenyl-1-acetone, 1-hydroxyl-cyclohexyl benzophenone, benzophenone, 2,4,6-Three methyl Benzene formyl diphenyl phosphine oxide or two aryl phosphine oxide compound.
5. the application of the described a kind of glass-hard organosilicon protective coating of claim 1 is characterized in that: the surface encapsulation that is used as surface hydrophobicity protective treatment, historical relic's protection or the electronic devices and components of stone material, pottery, concrete, glass, metal, timber, plastics.
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| CN102311524A (en) * | 2010-06-29 | 2012-01-11 | 高雄应用科技大学 | Solidifiable composition and method for preparing workpiece with transparent protective layer by using solidifiable composition |
| CN103266737A (en) * | 2013-04-22 | 2013-08-28 | 上海龙人建设集团有限公司 | Corrosion prevention structure and corrosion prevention process for surface of building stone |
| CN104774548B (en) * | 2015-04-28 | 2017-10-03 | 重庆卡勒斯通科技有限公司 | A kind of wood surface protection nano coating and its manufacture craft |
| CN106084266A (en) * | 2016-05-30 | 2016-11-09 | 哈尔滨工业大学 | A kind of modified organic silicone resin improves the method for biaxially oriented polyester film surface performance |
| CN109161230B (en) * | 2018-07-19 | 2020-09-29 | 陕西师范大学 | Method for reinforcing soil ink mark slogan to prevent writing from falling off and application thereof |
| CN109233478A (en) * | 2018-07-27 | 2019-01-18 | 东莞环球经典新型材料有限公司 | A kind of fluorine-containing organic silicon stone protective agent and preparation method thereof |
| CN112876990A (en) * | 2021-01-19 | 2021-06-01 | 首都师范大学 | Photocuring organic silicon transparent flexible hard coating and preparation method thereof |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1478801A (en) * | 2003-07-11 | 2004-03-03 | 中国科学院广州化学研究所 | Method of modifying acrylate using organic silicone |
| CN1887972A (en) * | 2006-07-14 | 2007-01-03 | 浙江大学 | Nanometer SiO2 modifying process of ultraviolet ray cured adhesive |
| CN1903898A (en) * | 2006-07-21 | 2007-01-31 | 华南理工大学 | Siloxane containing water soluble polymer emulsion and redispersible emulsion powder and its preparation method |
| CN1974581A (en) * | 2006-12-13 | 2007-06-06 | 中国科学院广州化学研究所 | Silicon-containing (methyl) acrylate monomer and its copolymer and their prepn process |
-
2009
- 2009-03-18 CN CN2009100380090A patent/CN101508852B/en not_active Expired - Fee Related
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1478801A (en) * | 2003-07-11 | 2004-03-03 | 中国科学院广州化学研究所 | Method of modifying acrylate using organic silicone |
| CN1887972A (en) * | 2006-07-14 | 2007-01-03 | 浙江大学 | Nanometer SiO2 modifying process of ultraviolet ray cured adhesive |
| CN1903898A (en) * | 2006-07-21 | 2007-01-31 | 华南理工大学 | Siloxane containing water soluble polymer emulsion and redispersible emulsion powder and its preparation method |
| CN1974581A (en) * | 2006-12-13 | 2007-06-06 | 中国科学院广州化学研究所 | Silicon-containing (methyl) acrylate monomer and its copolymer and their prepn process |
Non-Patent Citations (1)
| Title |
|---|
| 黄月文,刘伟区.含硅（甲基）丙烯酸酯在涂料工业中的研究和应用进展.《涂料工业》.2006,第36卷(第11期), * |
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