CN1694807B - 涂覆在塑料基底上的粘合层 - Google Patents
涂覆在塑料基底上的粘合层 Download PDFInfo
- Publication number
- CN1694807B CN1694807B CN038248689A CN03824868A CN1694807B CN 1694807 B CN1694807 B CN 1694807B CN 038248689 A CN038248689 A CN 038248689A CN 03824868 A CN03824868 A CN 03824868A CN 1694807 B CN1694807 B CN 1694807B
- Authority
- CN
- China
- Prior art keywords
- alkenyl
- cyclosiloxane
- adhesive layer
- goods
- substrates
- 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.)
- Expired - Fee Related
Links
- 239000000758 substrate Substances 0.000 title claims abstract description 58
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- 239000004033 plastic Substances 0.000 title abstract description 6
- 238000000034 method Methods 0.000 claims abstract description 27
- 239000012790 adhesive layer Substances 0.000 claims description 37
- -1 polyethylene Polymers 0.000 claims description 27
- 239000010410 layer Substances 0.000 claims description 25
- 238000006243 chemical reaction Methods 0.000 claims description 15
- 125000003342 alkenyl group Chemical group 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- 229920002554 vinyl polymer Polymers 0.000 claims description 10
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 8
- 238000000151 deposition Methods 0.000 claims description 8
- 230000008021 deposition Effects 0.000 claims description 8
- 229910052710 silicon Inorganic materials 0.000 claims description 8
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- 229920005989 resin Polymers 0.000 claims description 7
- 239000011347 resin Substances 0.000 claims description 7
- 229920001187 thermosetting polymer Polymers 0.000 claims description 7
- 238000005229 chemical vapour deposition Methods 0.000 claims description 6
- 229920000728 polyester Polymers 0.000 claims description 6
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 5
- 239000012467 final product Substances 0.000 claims description 5
- 239000000047 product Substances 0.000 claims description 5
- 239000004642 Polyimide Substances 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 229920001577 copolymer Polymers 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
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- 239000004814 polyurethane Substances 0.000 claims description 4
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- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 3
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- 239000004698 Polyethylene Substances 0.000 claims description 3
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- 229910010413 TiO 2 Inorganic materials 0.000 claims description 3
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 3
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 claims description 3
- JJRDHFIVAPVZJN-UHFFFAOYSA-N cyclotrisiloxane Chemical compound O1[SiH2]O[SiH2]O[SiH2]1 JJRDHFIVAPVZJN-UHFFFAOYSA-N 0.000 claims description 3
- 239000011737 fluorine Substances 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 238000000465 moulding Methods 0.000 claims description 3
- 229920002492 poly(sulfone) Polymers 0.000 claims description 3
- 239000004584 polyacrylic acid Substances 0.000 claims description 3
- 229920002239 polyacrylonitrile Polymers 0.000 claims description 3
- 229920002647 polyamide Polymers 0.000 claims description 3
- 229920000570 polyether Polymers 0.000 claims description 3
- 229920000573 polyethylene Polymers 0.000 claims description 3
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- 239000004800 polyvinyl chloride Substances 0.000 claims description 3
- 229920000915 polyvinyl chloride Polymers 0.000 claims description 3
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- 239000004416 thermosoftening plastic Substances 0.000 claims description 3
- 238000009616 inductively coupled plasma Methods 0.000 claims description 2
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- 229920000515 polycarbonate Polymers 0.000 claims 4
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- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 15
- 239000000463 material Substances 0.000 description 13
- 238000007598 dipping method Methods 0.000 description 11
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 8
- 239000011787 zinc oxide Substances 0.000 description 8
- GCSJLQSCSDMKTP-UHFFFAOYSA-N ethenyl(trimethyl)silane Chemical compound C[Si](C)(C)C=C GCSJLQSCSDMKTP-UHFFFAOYSA-N 0.000 description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- UHUUYVZLXJHWDV-UHFFFAOYSA-N trimethyl(methylsilyloxy)silane Chemical compound C[SiH2]O[Si](C)(C)C UHUUYVZLXJHWDV-UHFFFAOYSA-N 0.000 description 6
- JJQZDUKDJDQPMQ-UHFFFAOYSA-N dimethoxy(dimethyl)silane Chemical group CO[Si](C)(C)OC JJQZDUKDJDQPMQ-UHFFFAOYSA-N 0.000 description 5
- UQEAIHBTYFGYIE-UHFFFAOYSA-N hexamethyldisiloxane Chemical compound C[Si](C)(C)O[Si](C)(C)C UQEAIHBTYFGYIE-UHFFFAOYSA-N 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 4
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 4
- TVIDDXQYHWJXFK-UHFFFAOYSA-N dodecanedioic acid Chemical compound OC(=O)CCCCCCCCCCC(O)=O TVIDDXQYHWJXFK-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 4
- 229960001296 zinc oxide Drugs 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
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- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
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- 229920000305 Nylon 6,10 Polymers 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 235000011037 adipic acid Nutrition 0.000 description 2
- 239000001361 adipic acid Substances 0.000 description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
- 238000005336 cracking Methods 0.000 description 2
- QSAWQNUELGIYBC-UHFFFAOYSA-N cyclohexane-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCCCC1C(O)=O QSAWQNUELGIYBC-UHFFFAOYSA-N 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 230000003301 hydrolyzing effect Effects 0.000 description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- 238000002454 metastable transfer emission spectrometry Methods 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 125000005375 organosiloxane group Chemical group 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 230000002269 spontaneous effect Effects 0.000 description 2
- CPUDPFPXCZDNGI-UHFFFAOYSA-N triethoxy(methyl)silane Chemical compound CCO[Si](C)(OCC)OCC CPUDPFPXCZDNGI-UHFFFAOYSA-N 0.000 description 2
- JZLWSRCQCPAUDP-UHFFFAOYSA-N 1,3,5-triazine-2,4,6-triamine;urea Chemical compound NC(N)=O.NC1=NC(N)=NC(N)=N1 JZLWSRCQCPAUDP-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 1
- GTACSIONMHMRPD-UHFFFAOYSA-N 2-[4-[2-(benzenesulfonamido)ethylsulfanyl]-2,6-difluorophenoxy]acetamide Chemical compound C1=C(F)C(OCC(=O)N)=C(F)C=C1SCCNS(=O)(=O)C1=CC=CC=C1 GTACSIONMHMRPD-UHFFFAOYSA-N 0.000 description 1
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 1
- XDLMVUHYZWKMMD-UHFFFAOYSA-N 3-trimethoxysilylpropyl 2-methylprop-2-enoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C(C)=C XDLMVUHYZWKMMD-UHFFFAOYSA-N 0.000 description 1
- NDWUBGAGUCISDV-UHFFFAOYSA-N 4-hydroxybutyl prop-2-enoate Chemical compound OCCCCOC(=O)C=C NDWUBGAGUCISDV-UHFFFAOYSA-N 0.000 description 1
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- 101710130081 Aspergillopepsin-1 Proteins 0.000 description 1
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 description 1
- IJLWNXNUUHIUCT-UHFFFAOYSA-N C[SiH](O[SiH2]O[SiH2]O[SiH3])C=C Chemical class C[SiH](O[SiH2]O[SiH2]O[SiH3])C=C IJLWNXNUUHIUCT-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- 102100031007 Cytosolic non-specific dipeptidase Human genes 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 1
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- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- 241001597008 Nomeidae Species 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- 229920012266 Poly(ether sulfone) PES Polymers 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 229910006404 SnO 2 Inorganic materials 0.000 description 1
- BOTDANWDWHJENH-UHFFFAOYSA-N Tetraethyl orthosilicate Chemical compound CCO[Si](OCC)(OCC)OCC BOTDANWDWHJENH-UHFFFAOYSA-N 0.000 description 1
- ORLQHILJRHBSAY-UHFFFAOYSA-N [1-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1(CO)CCCCC1 ORLQHILJRHBSAY-UHFFFAOYSA-N 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 239000004676 acrylonitrile butadiene styrene Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000004411 aluminium Substances 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 230000000712 assembly Effects 0.000 description 1
- 238000000429 assembly Methods 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
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- 229940106691 bisphenol a Drugs 0.000 description 1
- OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical compound NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 239000011469 building brick Substances 0.000 description 1
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 1
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 229910000420 cerium oxide Inorganic materials 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 239000011247 coating layer Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- 150000007973 cyanuric acids Chemical class 0.000 description 1
- OIWOHHBRDFKZNC-UHFFFAOYSA-N cyclohexyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1CCCCC1 OIWOHHBRDFKZNC-UHFFFAOYSA-N 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 230000032798 delamination Effects 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- MNFGEHQPOWJJBH-UHFFFAOYSA-N diethoxy-methyl-phenylsilane Chemical compound CCO[Si](C)(OCC)C1=CC=CC=C1 MNFGEHQPOWJJBH-UHFFFAOYSA-N 0.000 description 1
- AHUXYBVKTIBBJW-UHFFFAOYSA-N dimethoxy(diphenyl)silane Chemical compound C=1C=CC=CC=1[Si](OC)(OC)C1=CC=CC=C1 AHUXYBVKTIBBJW-UHFFFAOYSA-N 0.000 description 1
- CVQVSVBUMVSJES-UHFFFAOYSA-N dimethoxy-methyl-phenylsilane Chemical compound CO[Si](C)(OC)C1=CC=CC=C1 CVQVSVBUMVSJES-UHFFFAOYSA-N 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- FALCQDAWENTNHF-UHFFFAOYSA-N ethenyl(2-methoxyethoxy)silane Chemical class COCCO[SiH2]C=C FALCQDAWENTNHF-UHFFFAOYSA-N 0.000 description 1
- FWDBOZPQNFPOLF-UHFFFAOYSA-N ethenyl(triethoxy)silane Chemical class CCO[Si](OCC)(OCC)C=C FWDBOZPQNFPOLF-UHFFFAOYSA-N 0.000 description 1
- XZFFGKZBTQABBO-UHFFFAOYSA-N ethoxy(dimethyl)silane Chemical compound CCO[SiH](C)C XZFFGKZBTQABBO-UHFFFAOYSA-N 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
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- 229920002313 fluoropolymer Polymers 0.000 description 1
- 239000004811 fluoropolymer Substances 0.000 description 1
- 238000011010 flushing procedure Methods 0.000 description 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- 125000006038 hexenyl group Chemical group 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 125000004464 hydroxyphenyl group Chemical group 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- MRNHPUHPBOKKQT-UHFFFAOYSA-N indium;tin;hydrate Chemical compound O.[In].[Sn] MRNHPUHPBOKKQT-UHFFFAOYSA-N 0.000 description 1
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000002648 laminated material Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 210000001161 mammalian embryo Anatomy 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000009740 moulding (composite fabrication) Methods 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
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- 229920001558 organosilicon polymer Polymers 0.000 description 1
- BMMGVYCKOGBVEV-UHFFFAOYSA-N oxo(oxoceriooxy)cerium Chemical compound [Ce]=O.O=[Ce]=O BMMGVYCKOGBVEV-UHFFFAOYSA-N 0.000 description 1
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- 238000009832 plasma treatment Methods 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920005668 polycarbonate resin Polymers 0.000 description 1
- 239000004431 polycarbonate resin Substances 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 229920006389 polyphenyl polymer Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000003252 repetitive effect Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003856 thermoforming Methods 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
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- JCVQKRGIASEUKR-UHFFFAOYSA-N triethoxy(phenyl)silane Chemical compound CCO[Si](OCC)(OCC)C1=CC=CC=C1 JCVQKRGIASEUKR-UHFFFAOYSA-N 0.000 description 1
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 1
- 238000007666 vacuum forming Methods 0.000 description 1
Classifications
-
- 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
- C08J7/123—Treatment by wave energy or particle radiation
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B27/00—Layered products comprising a layer of synthetic resin
- B32B27/36—Layered products comprising a layer of synthetic resin comprising polyesters
-
- B—PERFORMING OPERATIONS; TRANSPORTING
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Abstract
含有塑料基底和等离子体聚合的具有选择性不饱和的环硅氧烷粘合层的制品及其成型方法。
Description
技术领域
本发明总体上涉及在硅原子上具有至少一个链烯基取代基的环硅氧烷作为塑料基底的粘合层、含有它制品、和制造这种制品的方法。
背景技术
已经发现塑料可广泛地用作大量的和不同定位的基底材料。其原因是塑料通常质轻、延展性高且具有高的可见光透过度。某些塑料，例如聚碳酸酯(PC)，具有高冲击强度的额外优势。塑料基底的应用包括，但不限于，用作汽车窗、前灯和车身镶板、建筑窗、显示器、太阳能电池和收集器、飞机窗和顶盖、及仪表。在大多数应用中，塑料基底配有一个或多个功能性涂层。例如，汽车窗至少需要紫外线(UV)过滤涂层以保护它们不受阳光暴晒，并需要耐磨涂层以防止它们擦伤。此外，汽车窗需要具有红外(IR)反射涂层用作加热器栅格的透明导电涂层、和/或电镀铬涂层。氧和水的阻隔涂层对于显示器、太阳能电池和双格窗(dual-pane window)是重要的。
涂层虽然具有必要的功能，但内在的特性终究被证实对其最终的层状制品往往是不利的。例如，很多涂层具有显著不同于下层塑料基底的模数和热膨胀系数(CTE)。这种性能上的不匹配在热循环和暴露于高湿度或浸于水期间，会在涂层中以及层界面上引起大的应变。这就导致涂层的分层和/或开裂。
已经开发出一些解决这一问题的方法。一种方法是通过使用分层的界面使基底和涂层之间具有贴合性。例如，美国专利4927704公开了通过等离子体增强的化学气相沉积(PECVD)形成分层界面，从而提供贴合性。在该方法中，使用乙烯基三甲基硅烷(VTMS)或六甲基二硅氧烷(HMDSO)，且从基底的性能到涂层的性能逐层不同。该方法虽然有所帮助，但只是在沉积速度慢的方法中使用才有效。为了降低成本，高沉积速度的方法在工业上是受欢迎的，但这种方法经济上是不可取的。
另一种试图获得贴合性的方法是使用单粘合层。例如，美国专利5154582公开了美国专利4224378描述的通式R1 nSiZ(4-n)和美国专利4242381描述的R2Si(OH)3的有机硅氧烷的使用。在这些预期的特定化合物中包括六甲基二硅氮烷(HMDZ)、HMDSO、VTMS和辛甲基环丁硅氧烷(D4)。
在美国专利5718967中，公开了一种层压材料，其中第一粘合促进层为二甲氧基二甲基硅烷(DMDMS)、甲基三甲氧基硅烷、四甲氧基硅烷、甲基三乙氧基硅烷、二乙氧基二甲基硅烷、甲基三乙氧基硅烷、三乙氧基乙烯基硅烷、四乙氧基硅烷、二甲氧基甲基苯基硅烷、苯基三甲氧基硅烷、3-环氧丙氧基丙基三甲氧基硅烷、3-甲基丙烯酰氧基丙基三甲氧基硅烷、二乙氧基甲基苯基硅烷、三(2-甲氧基乙氧基)乙烯基硅烷、苯基三乙氧基硅烷、二甲氧基二苯基硅烷、四甲基二硅氧烷(TMDSO)、HMDSO、HMDZ和四甲基硅氮烷的等离子体聚合的有机硅聚合物。
虽然进行了这些努力，但仍需要提供有改善贴合性的粘合层用来获得更有效的热循环和水解稳定性。
发明概述
本发明涉及包含塑料基底和在所述塑料基底表面上的粘合层的制品，所述粘合层含有等离子体反应的环硅氧烷，所述环硅氧烷具有至少一个连接到硅原子的C2-C10链烯基；及其成型方法。在一个实施方式中，环硅氧烷为七甲基(乙烯基)四硅氧烷。
发明详述
塑料基底：
对于塑料基底没有限制，包括含有热塑性聚合物和热固性聚合物的那些。只是举例来说，该基底，一般含有聚合物树脂。例如，基底可以含有聚碳酸酯。适于成型基底的聚碳酸酯是本领域公知的且通常含有下式的重复单元：
其中R1为用于聚合物生成反应的二羟酚的二价芳香族基团(例如，2，2-双(4-羟苯基)-丙烷基团，又称双酚A)；或有机多羧酸(例如，对苯二甲酸、间苯二甲酸、六氢化邻苯二甲酸、己二酸、癸二酸、十二烷二酸等)。这些聚碳酸酯树脂为芳香族碳酸酯聚合物，其可以通过一个或多个二羟酚与碳酸酯前体(例如光气、卤代甲酸酯或碳酸酯)的反应来制备。在本发明中可以用作塑料基底的聚碳酸酯的一个例子为由General Electric Company制造。
芳香族碳酸酯聚合物可以通过本领域公知的方法进行制备，这些方法例如在美国专利3,161,615；3,220,973；3,312,659；3,312,660；3,313,777；3,666,614；3,989,672；4,200,681；4,842,941；和4,210,699中进行了描述。
该塑料基底还可以含有聚酯碳酸酯，其可以通过碳酸酯前体、二羟酚和二羧酸或其成酯衍生物进行反应来制备。聚酯碳酸酯的例子，在美国专利4,454,275；5,510,448；4,194,038；和5,463,013中进行了描述。
塑料基底还可以含有热塑性或热固性材料。适宜的热塑性材料的例子包括聚乙烯、聚丙烯、聚苯乙烯、聚醋酸乙烯酯、聚乙烯醇；聚乙烯醇缩乙醛、聚甲基丙烯酸酯、聚丙烯酸、聚醚、聚酯、聚碳酸酯、纤维素树脂(cellulousresin)、聚丙烯腈、聚酰胺、聚酰亚胺、聚氯乙烯、含氟树脂和聚砜。适宜的热固性材料的例子包括环氧和脲蜜胺。
本领域还公知，丙烯酸聚合物为另一种可以形成塑料基底的材料。丙烯酸聚合物可以由单体制备，这些单体例如丙烯酸甲酯、丙烯酸、甲基丙烯酸、甲基丙烯酸甲酯、甲基丙烯酸丁酯、甲基丙烯酸环己基酯等。还可以使用取代的丙烯酸酯和甲基丙烯酸酯，例如丙烯酸羟乙基酯，丙烯酸羟丁基酯，丙烯酸2-乙基己基酯和丙烯酸正丁酯。
还可以使用聚酯来形成塑料基底。聚酯是本领域公知的，可以通过有机多羧酸(例如，苯二甲酸、六氢化邻苯二甲酸、己二酸、马来酸、对苯二甲酸、间苯二甲酸、癸二酸、十二烷二酸等)或它们的酸酐与含有伯或仲羟基的有机多元醇(例如，乙二醇、丁二醇、新戊二醇和环己烷二甲醇)的聚酯化作用来制备。
聚氨酯是可用来形成塑料基底的另一类材料.聚氨酯是本领域公知的，其一般通过聚异氰酸酯和多元醇的反应来制备.可用的聚异氰酸酯的例子包括六亚甲基二异氰酸酯、甲苯二异氰酸脂、异佛尔酮二异氰酸酯，和这些二异氰酸酯的缩二脲和三异氰脲酸酯.可用的多元醇的例子包括低分子量脂肪族多元醇、聚酯多元醇、聚醚多元醇、脂肪醇等.
其它可形成基底的材料的例子包括丙烯腈-丁二烯-苯乙烯、(聚苯二甲酸丁二醇酯，由General Electric Co.生产)、
(
和
的共混物，由General Electric Co.生产)等。在本发明的各种实施方式中，基底含有清澈的聚合材料，例如聚碳酸酯(PC)(由General ElectricCompany销售，商标为
)、聚酯碳酸酯(PPC)、聚醚砜(PES)(由Amoco销售，商标为)、聚醚酰亚胺(PEI或聚酰亚胺)(由General ElectricCompany销售，商标为)和丙烯酸类。
塑料基底可以用常规方法来形成，例如通过注射模塑、挤出、冷成型、真空成型、吹塑、压模、转移模塑、热成型等。制品可以为任意形状且不需为最终的商品，即，其可以为能够切割或剪切(sized)或机械成型为最终制品的片材或膜。基底可以透明或不透明。基底可以为刚性或柔性。也可以预期是上述材料相互之间的共混物，及与添加剂例如填料、增塑剂、染色剂(tint)、着色剂等的共混物。
优选的基底由聚碳酸酯形成。这里所用的术语聚碳酸酯还包括聚碳酸酯与其它材料例如聚酯和抗冲改性剂的共混物。
如本领域人员所知道的，用作基底的塑料的选择和基底自身的厚度是设定制品用途的函数。基底的厚度没有限定，一般不低于0.05mm；在其他实践中，厚度为约4mm-约6mm。
粘合层：
粘合层(BL)含有等离子体反应的环硅氧烷，其中所述环硅氧烷具有至少一个连接到硅原子的C2-C10链烯基。在一个实施方式中，环硅氧烷可以为未取代的；在另一个实施方式中，其可以为以一个或多个C1-C3低级烷基的有机基取代，即环硅氧烷可以由一个或多个甲基、乙基、丙基和/或异丙基或其组合进行取代。在具体实践中，环硅氧烷的结构为环三聚体(或环丙硅氧烷)；环四聚体(或环丁硅氧烷)；或环五聚体(或环戊硅氧烷)。至少一个具有2-10个碳原子的链烯基直接连接到环硅氧烷的硅原子上。在具体实施方式中，仅有一个这种链烯基被这样连接。对于链烯基具有3个或多个碳原子的实施方式中，双键可以位于该部分中的任意位置。在另一个实施方式中，这里的链烯基具有末端碳-碳双键。链烯基的例子包括乙烯基、烯丙基、己烯基等。
本发明预期的具体的环硅氧烷具有如下结构，但并不限于此结构：
其中每个R独立地为氢、甲基或乙基，只要至少一个R为C2-C10链烯基即可，且n为2-8的整数。
在本发明实践的一个实施方式中，至少一个R为C2-C6链烯基；且n为3、4或5。在本发明实践的另一个实施方式中，每个R为甲基，只要仅有一个R为C2-C6链烯基，例如，乙烯基，且n为4。在本发明的一个具体实施方式中，环硅氧烷为七甲基(乙烯基)环丁硅氧烷(乙烯基-D4)。
可以通过本领域已知的等离子体沉积法，将环硅氧烷粘合层施加到塑料基底，例如通过等离子体增强的化学气相沉积(PECVD)(如美国专利6,420,032所述)，通过感应耦合等离子体(ICP)、电子回旋加速器谐振(ECR)等，或通过膨胀热等离子体(ETP)，特别是在线(in-line)ETP(如共同所有的(commonly-owned)美国专利6,397,776所述).在沉积环硅氧烷之前，以已知的方式清洁塑料基底，例如通过如异丙醇的醇溶剂来进行清洗.
粘合层的厚度取决于为上述制品设定用途的塑料基底和性质。对于设定的用途没有限定，包括优选作为交通工具窗，例如轿车、卡车、摩托车、拖拉机、船或飞机窗的那些用途。基底还可以包括显示屏，例如电视屏、LCD屏、计算机监视器屏、等离子体显示屏或用于计算机监视器的强光防护。这些屏幕涂以UV吸收层和IR反射层以利于防止屏幕变黄和防止显示器内电子组件受UV照射和热的破坏。基底还可以包括电子器件基底，例如太阳能电池或液晶显示器(LCD)基底。对粘合层的厚度没有限定，通常不低于10nm。在各种实践中，粘合层厚度为约20nm-约100nm。对于其它实践，粘合层厚度为约200nm-约500nm。
在粘合层已通过等离子体反应沉积后，根据需要，可以在其上面涂覆其它涂层。例如，可以涂覆一个或多个UV吸收层，通常是但不必须是金属氧化物。优选的金属氧化物，只是举例来说，包括本领域已知的氧化锌(ZnO)、掺杂的氧化锌例如铟掺杂氧化锌(IZO)和铝掺杂氧化锌(AZO)、二氧化钛(TiO2)、氧化铈(Ce2O3)等。其它涂层包括透明导电涂层，其由本领域已知的材料例如氧化铟锡(ITO)、氧化锡(SnO2)等形成。
在又一个实践中，可以任选地使用一个或多个耐磨涂层，例如，这种涂层可以涂覆在UV吸收层上。这里的耐磨层包括本领域已知的那些，例如由等离子体反应形成的那些和氧化的有机硅材料例如D4、HMDSO、TMDSO等。
还可以任选地使用IR反射涂层。如本领域已知的，这些包括但不限于金属例如银(Ag)和铝(Al)，和IR反射氧化物例如ITO；且包括多层层叠例如，但不限于，TiO2/Ag/TiO2；ZnO/Ag/ZnO；IZO/Ag/IzO；和AZO/Ag/AZO及其组合。
本发明通常是用于任何需要在塑料基底上使用涂层的应用。更具体地说，其可用作粘合层，用于例如汽车窗、前灯和车身镶板、建筑窗、显示器、太阳能电池和收集器、飞机窗和顶盖及仪表。最特别的应用为汽车上釉。
下列实施例仅用于说明而不是限定本发明的范围。
实施例
在聚碳酸酯(PC)基底上的七甲基(乙烯基)环丁硅氧烷(乙烯基-D4)的等离子体反应可用作UV过滤和耐磨涂层的粘合层，以改善它们对热循环的耐受力和水解稳定性。在如美国专利6,397,776所描述的在线结构中，使用膨胀热等离子体(ETP)进行所有沉积。每一层使用分离的ETP。用异丙醇清洗PC片材、冲洗、风干，然后在80-100℃真空中烘过夜。将基底置于负载锁定(loadlock)的支架上，一般抽气至1mT，然后放入在线涂布机中。通过一系列ETP的转移来涂覆基底。一般地，第一站为红外(IR)加热器，用以在粘合层沉积前将PC的表面温度提高到所需的水平。
对使用各种有机硅氧烷形成相似的粘合层进行比较，例如辛甲基环丁硅氧烷(D4)、二甲基二甲氧基硅烷(DMDMS)、乙烯基三甲基硅烷(VTMS)和四甲基二硅氧烷(TMDSO)。比较的标准是通过测试划格带(cross hatch tape)(使用具有1巴(B)-5巴(B)单元的额定体系的ASTM1044)或张力测试而测定的对PC的初始粘合力，在65℃的水中浸渍3天后的粘合力(“WS adh”)，及-50至135℃的10次热循环后的粘合力或开裂。
通过在由PC/BL/UV吸收层和4个耐磨层的6层体系上重复这些测试来对作为粘合层的涂层的性能进行评价。UV吸收层含有如美国专利6,420,032所述的ZnO。每个耐磨层都由等离子体聚合和氧化的D4构成。表1比较了这些BL材料的性能。对于初始粘合力和在水中浸渍后的粘合力，组件的性能标记为“P-adh”和“P-WS adh”。在热循环期间，所有研究的材料具有良好的层叠贴合性，从而使6层组件在热循环测试后，没有降低粘合力或发生开裂。对于单独涂层和6层结构的粘合层，关键区别为初始沉积时的粘合力和在水中浸渍后的粘合力。如表1所显示的，对于单独涂层和6层结构的粘合层，V-D4具有优异的初始粘合力和在水中浸渍后的粘合力。对于V-D4，在水中浸渍前、后，对总计34个样品进行评价。初始平均粘合方和标准偏差为3377和1617，且在水中浸渍后为2838和1243，表示在水中浸渍后没有统计上的显著变差。
对该组件还进行热循环后和在水中浸渍后的划格测试(5巴粘合力)。对一些样品还进行6天的浸渍。为了进一步强化粘合层，将PC涂层的厚度从100增加到600nm。对于V-D4，没有观察到性能上的区别。在比较中，没有乙烯基的D4具有极低的粘合力，即使是极薄的涂层，在水中浸渍后粘合力也降低了。约300nm或更厚的涂层在水中浸渍后失效。在水中浸渍3天，具有薄D4粘合层的组件其粘合力的典型值降低至2-3巴，且几个1巴的样品自发地层离。DMDMS的性能稍优于初始粘合力改善的D4，即1787绝对压强(Psia)，但水浸性能差，即316绝对压强(Psia)。D4组件的性能通常为具有良好初始粘合力但水浸性能差，典型值为2-3巴，而几个具有自发层离的样品为1巴。VTMS具有良好的初始粘合力但水浸性能也差。然而，在水浸期间，大多数具有VTMS粘合层的组件在浸水后自发层离。TMDSO具有差的初始粘合力且水浸性能差。V-D4粘合层的其它特性在于PC基底不需要经等离子体处理，从而省去了一个处理步骤及相关成本。
而且，对于加入氧的等离子体的实践，本发明的实践提供了改善的坚固性。例如，在迄今为止的实践中，当加氧到等离子体中时，使用例如D4或DMDMS作为硬层，较薄的涂层厚度(例如大约300nm)就发生层离。相反地，本发明，例如非限定地具体V-D4作为粘合层时，即使在较厚的涂层(例如600nm)中，也可以向等离子体中加入约0.2升每分钟(LPM)至约0.06LPM的添加氧，同时保持粘合力。
表1
Claims (28)
1.一种制品，其含有：
塑料基底；和
在所述塑料基底表面上的粘合层，所述粘合层含有等离子体反应的环硅氧烷，所述环硅氧烷具有至少一个连接到硅原子的C2-C10链烯基。
2.权利要求1的制品，其中所述环硅氧烷具有如下结构：
其中每个R独立地为氢、甲基或乙基，只要至少一个R为C2-C6链烯基即可；且n为2-8的整数。
3.权利要求2的制品，其中至少一个R为C2-C6链烯基；且n为3、4或5。
4.权利要求3的制品，其中每个R为甲基，只要仅有一个R为C2-C6链烯基即可。
5.权利要求4的制品，其中所述链烯基具有末端碳-碳双键。
6.权利要求5的制品，其中所述链烯基为乙烯基；且n为4。
7.权利要求1的制品，其中所述塑料基底含有热塑性或热固性聚合物。
8.权利要求6的制品，其中所述塑料基底选自聚乙烯、聚丙烯、聚苯乙烯、聚乙烯醇、聚乙烯醇缩乙醛；聚甲基丙烯酸酯、聚丙烯酸、聚醚、聚酯、聚碳酸酯、纤维素树脂、聚丙烯腈、聚酰胺、聚酰亚胺、聚氯乙烯、含氟树脂和聚砜、丙烯酸聚合物和聚氨酯。
9.权利要求1的制品，其中所述粘合层厚度不低于10nm。
10.权利要求1的制品，在所述粘合层上还含有一个或多个附加涂层，所述附加涂层为一个或多个UV吸收层、一个或多个耐磨层、一个或多个透明导电层、或一个或多个IR反射层。
11.一种制品，其含有：
热固性或热塑性塑料基底；和
在所述基底表面上的粘合层，所述粘合层含有等离子体反应的环硅氧烷，所述环硅氧烷具有一个连接到硅原子的C2-C6链烯基，所述环硅氧烷为环丙硅氧烷、环丁硅氧烷或环戊硅氧烷。
12.权利要求11的制品，其中所述基底为热塑性；所述环硅氧烷为环丁硅氧烷；和所述链烯基为乙烯基。
13.一种多层制品，其含有：
聚碳酸酯基底；和
在所述聚碳酸酯基底表面上的粘合层，所述粘合层含有等离子体反应的七甲基(乙烯基)环丁硅氧烷。
14.成型多层制品的方法，其包含：
提供塑料基底；和
在所述塑料基底的表面上对环硅氧烷进行等离子体反应以形成粘合层，所述环硅氧烷具有至少一个连接到硅原子的C2-C10链烯基。
15.权利要求14的方法，其中所述等离子体反应通过膨胀热等离子体、等离子体增强的化学气相沉积、感应耦合等离子体或电子回旋加速器谐振来进行的。
16.权利要求14的方法，其中所述环硅氧烷具有如下结构：
其中每个R独立地为氢、甲基或乙基，只要至少一个R为C2-C6链烯基即可；且n为2-8的整数。
17.权利要求16的方法，其中至少一个R为C2-C6链烯基，且n为3、4或5。
18.权利要求17的方法，其中每个R为甲基，只要仅有一个R为C2-C6链烯基即可。
19.权利要求18的方法，其中所述链烯基具有末端碳-碳双键。
20.权利要求19的方法，其中所述链烯基为乙烯基；且n为4。
21.权利要求14的方法，其中所述塑料基底含有热塑性或热固性聚合物。
22.权利要求21的方法，其中所述塑料基底选自聚乙烯、聚丙烯、聚苯乙烯、聚乙烯醇、聚乙烯醇缩乙醛、聚甲基丙烯酸酯、聚丙烯酸、聚醚、聚酯、聚碳酸酯、纤维素树脂、聚丙烯腈、聚酰胺、聚酰亚胺、聚氯乙烯、含氟树脂和聚砜、丙烯酸聚合物和聚氨酯。
23.权利要求11的方法，其中所述粘合层沉积至约200nm-约500nm的厚度。
24.权利要求12的方法，还包含在所述粘合层上沉积UV吸收层，所述UV吸收层含有ZnO、TiO2或Ce2O3。
25.成型多层制品的方法，其包含：
提供热固性或热塑性塑料基底；和
在所述基底的表面上对环硅氧烷进行等离子体反应以形成粘合层，所述环硅氧烷具有一个连接到硅原子的C2-C6链烯基，所述环硅氧烷为环丙硅氧烷、环丁硅氧烷、或环戊硅氧烷。
26.权利要求25的方法，其中所述基底为热塑性，所述环硅氧烷为环丁硅氧烷，和所述链烯基为乙烯基。
27.制造多层制品的方法，其包含：
提供聚碳酸酯基底；和
在所述聚碳酸酯基底的表面上使七甲基(乙烯基)环丁硅氧烷进行等离子体反应以形成粘合层。
28.权利要求27的方法，还包含在所述粘合层上沉积一个或多个耐磨层。
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| CN110591471B (zh) * | 2019-09-27 | 2021-06-08 | 新恒东薄膜材料（常州）有限公司 | 一种增强透明pi基材表面附着力的预涂液及其应用方法 |
| CN113897592A (zh) * | 2020-07-06 | 2022-01-07 | 江苏菲沃泰纳米科技股份有限公司 | 透明耐磨膜层、塑料表面改性方法以及产品 |
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- 2003-07-29 KR KR1020057006227A patent/KR20050057649A/ko not_active Application Discontinuation
- 2003-07-29 DE DE60321587T patent/DE60321587D1/de not_active Expired - Lifetime
- 2003-07-29 AT AT03808041T patent/ATE398018T1/de not_active IP Right Cessation
- 2003-07-29 EP EP20030808041 patent/EP1554114B1/en not_active Expired - Lifetime
- 2003-07-29 WO PCT/US2003/023446 patent/WO2004033204A1/en active Application Filing
- 2003-07-29 AU AU2003263819A patent/AU2003263819A1/en not_active Abandoned
- 2003-07-29 JP JP2004543221A patent/JP2006502026A/ja active Pending
- 2003-07-29 CN CN038248689A patent/CN1694807B/zh not_active Expired - Fee Related
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Also Published As
| Publication number | Publication date |
|---|---|
| KR20050057649A (ko) | 2005-06-16 |
| ATE398018T1 (de) | 2008-07-15 |
| US7056584B2 (en) | 2006-06-06 |
| CN1694807A (zh) | 2005-11-09 |
| EP1554114A1 (en) | 2005-07-20 |
| EP1554114B1 (en) | 2008-06-11 |
| AU2003263819A1 (en) | 2004-05-04 |
| US20040071971A1 (en) | 2004-04-15 |
| DE60321587D1 (de) | 2008-07-24 |
| WO2004033204A1 (en) | 2004-04-22 |
| JP2006502026A (ja) | 2006-01-19 |
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