CN111518504B - High-refraction high-transparency light path glue special for optical communication device - Google Patents
High-refraction high-transparency light path glue special for optical communication device Download PDFInfo
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- CN111518504B CN111518504B CN202010230650.0A CN202010230650A CN111518504B CN 111518504 B CN111518504 B CN 111518504B CN 202010230650 A CN202010230650 A CN 202010230650A CN 111518504 B CN111518504 B CN 111518504B
- Authority
- CN
- China
- Prior art keywords
- polythioether
- fluorene
- alcohol
- naphthyl
- optical communication
- 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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- 230000003287 optical effect Effects 0.000 title claims abstract description 56
- 238000004891 communication Methods 0.000 title claims abstract description 17
- 239000003292 glue Substances 0.000 title description 21
- -1 naphthyl fluorene Chemical compound 0.000 claims abstract description 82
- 229920006295 polythiol Polymers 0.000 claims abstract description 79
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 78
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims abstract description 69
- 239000003054 catalyst Substances 0.000 claims abstract description 46
- 239000000853 adhesive Substances 0.000 claims abstract description 29
- 230000001070 adhesive effect Effects 0.000 claims abstract description 29
- 239000003822 epoxy resin Substances 0.000 claims abstract description 24
- 229920000647 polyepoxide Polymers 0.000 claims abstract description 24
- 125000002723 alicyclic group Chemical group 0.000 claims abstract description 23
- 239000003085 diluting agent Substances 0.000 claims abstract description 23
- 150000001412 amines Chemical class 0.000 claims abstract description 22
- 239000003381 stabilizer Substances 0.000 claims abstract description 22
- 150000003573 thiols Chemical class 0.000 claims abstract description 14
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 51
- 239000002904 solvent Substances 0.000 claims description 34
- 238000006243 chemical reaction Methods 0.000 claims description 25
- DYOPVXMHYSXHNG-UHFFFAOYSA-N 6-[9-(6-hydroxynaphthalen-2-yl)fluoren-9-yl]naphthalen-2-ol Chemical compound C1=C(O)C=CC2=CC(C3(C4=CC=CC=C4C4=CC=CC=C43)C3=CC4=CC=C(C=C4C=C3)O)=CC=C21 DYOPVXMHYSXHNG-UHFFFAOYSA-N 0.000 claims description 19
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 18
- 239000000203 mixture Substances 0.000 claims description 15
- VOVUARRWDCVURC-UHFFFAOYSA-N thiirane Chemical compound C1CS1 VOVUARRWDCVURC-UHFFFAOYSA-N 0.000 claims description 14
- 125000003700 epoxy group Chemical group 0.000 claims description 12
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 claims description 9
- ZHUWXKIPGGZNJW-UHFFFAOYSA-N 6-methylheptyl 3-sulfanylpropanoate Chemical compound CC(C)CCCCCOC(=O)CCS ZHUWXKIPGGZNJW-UHFFFAOYSA-N 0.000 claims description 8
- 238000002156 mixing Methods 0.000 claims description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 8
- 238000004821 distillation Methods 0.000 claims description 7
- 238000000746 purification Methods 0.000 claims description 7
- 238000005406 washing Methods 0.000 claims description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 6
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 6
- XFUOBHWPTSIEOV-UHFFFAOYSA-N bis(oxiran-2-ylmethyl) cyclohexane-1,2-dicarboxylate Chemical compound C1CCCC(C(=O)OCC2OC2)C1C(=O)OCC1CO1 XFUOBHWPTSIEOV-UHFFFAOYSA-N 0.000 claims description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 6
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims description 6
- KYVBNYUBXIEUFW-UHFFFAOYSA-N 1,1,3,3-tetramethylguanidine Chemical compound CN(C)C(=N)N(C)C KYVBNYUBXIEUFW-UHFFFAOYSA-N 0.000 claims description 4
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 claims description 4
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 claims description 4
- JOBBTVPTPXRUBP-UHFFFAOYSA-N [3-(3-sulfanylpropanoyloxy)-2,2-bis(3-sulfanylpropanoyloxymethyl)propyl] 3-sulfanylpropanoate Chemical compound SCCC(=O)OCC(COC(=O)CCS)(COC(=O)CCS)COC(=O)CCS JOBBTVPTPXRUBP-UHFFFAOYSA-N 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 4
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 claims description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 3
- BRRSNXCXLSVPFC-UHFFFAOYSA-N 2,3,4-Trihydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C(O)=C1O BRRSNXCXLSVPFC-UHFFFAOYSA-N 0.000 claims description 3
- OJPDDQSCZGTACX-UHFFFAOYSA-N 2-[n-(2-hydroxyethyl)anilino]ethanol Chemical compound OCCN(CCO)C1=CC=CC=C1 OJPDDQSCZGTACX-UHFFFAOYSA-N 0.000 claims description 3
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 claims description 3
- 239000011668 ascorbic acid Substances 0.000 claims description 3
- 235000010323 ascorbic acid Nutrition 0.000 claims description 3
- 229960005070 ascorbic acid Drugs 0.000 claims description 3
- HNYOPLTXPVRDBG-UHFFFAOYSA-N barbituric acid Chemical compound O=C1CC(=O)NC(=O)N1 HNYOPLTXPVRDBG-UHFFFAOYSA-N 0.000 claims description 3
- ZFLIKDUSUDBGCD-UHFFFAOYSA-N parabanic acid Chemical compound O=C1NC(=O)C(=O)N1 ZFLIKDUSUDBGCD-UHFFFAOYSA-N 0.000 claims description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 3
- XZZNDPSIHUTMOC-UHFFFAOYSA-N triphenyl phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 XZZNDPSIHUTMOC-UHFFFAOYSA-N 0.000 claims description 3
- JJSYPAGPNHFLML-UHFFFAOYSA-N 2-ethyl-2-(hydroxymethyl)propane-1,3-diol;3-sulfanylpropanoic acid Chemical compound OC(=O)CCS.OC(=O)CCS.OC(=O)CCS.CCC(CO)(CO)CO JJSYPAGPNHFLML-UHFFFAOYSA-N 0.000 claims description 2
- ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 claims description 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 2
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims description 2
- 239000001099 ammonium carbonate Substances 0.000 claims description 2
- 235000012501 ammonium carbonate Nutrition 0.000 claims description 2
- DJUWPHRCMMMSCV-UHFFFAOYSA-N bis(7-oxabicyclo[4.1.0]heptan-4-ylmethyl) hexanedioate Chemical compound C1CC2OC2CC1COC(=O)CCCCC(=O)OCC1CC2OC2CC1 DJUWPHRCMMMSCV-UHFFFAOYSA-N 0.000 claims description 2
- KIKYOFDZBWIHTF-UHFFFAOYSA-N bis(oxiran-2-ylmethyl) cyclohex-3-ene-1,2-dicarboxylate Chemical compound C1CC=CC(C(=O)OCC2OC2)C1C(=O)OCC1CO1 KIKYOFDZBWIHTF-UHFFFAOYSA-N 0.000 claims description 2
- 229960004106 citric acid Drugs 0.000 claims description 2
- 235000015165 citric acid Nutrition 0.000 claims description 2
- 239000004973 liquid crystal related substance Substances 0.000 claims description 2
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 claims description 2
- 229960004889 salicylic acid Drugs 0.000 claims description 2
- 238000001308 synthesis method Methods 0.000 claims description 2
- 230000002194 synthesizing effect Effects 0.000 claims description 2
- 239000011975 tartaric acid Substances 0.000 claims description 2
- 235000002906 tartaric acid Nutrition 0.000 claims description 2
- 229960001367 tartaric acid Drugs 0.000 claims description 2
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 claims description 2
- XMLYCEVDHLAQEL-UHFFFAOYSA-N 2-hydroxy-2-methyl-1-phenylpropan-1-one Chemical compound CC(C)(O)C(=O)C1=CC=CC=C1 XMLYCEVDHLAQEL-UHFFFAOYSA-N 0.000 claims 1
- 229920005989 resin Polymers 0.000 abstract description 5
- 239000011347 resin Substances 0.000 abstract description 5
- 238000012360 testing method Methods 0.000 description 13
- 239000000463 material Substances 0.000 description 11
- 238000003786 synthesis reaction Methods 0.000 description 11
- 230000015572 biosynthetic process Effects 0.000 description 10
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 9
- 238000001723 curing Methods 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- LRWZZZWJMFNZIK-UHFFFAOYSA-N 2-chloro-3-methyloxirane Chemical compound CC1OC1Cl LRWZZZWJMFNZIK-UHFFFAOYSA-N 0.000 description 5
- 229920001296 polysiloxane Polymers 0.000 description 5
- 239000011521 glass Substances 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical group C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 239000004593 Epoxy Substances 0.000 description 3
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 3
- 238000003848 UV Light-Curing Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 238000004806 packaging method and process Methods 0.000 description 3
- 239000000565 sealant Substances 0.000 description 3
- 229910052710 silicon Inorganic materials 0.000 description 3
- 239000010703 silicon Substances 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- 238000002834 transmittance Methods 0.000 description 3
- IMQFZQVZKBIPCQ-UHFFFAOYSA-N 2,2-bis(3-sulfanylpropanoyloxymethyl)butyl 3-sulfanylpropanoate Chemical compound SCCC(=O)OCC(CC)(COC(=O)CCS)COC(=O)CCS IMQFZQVZKBIPCQ-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- KTPIWUHKYIJBCR-UHFFFAOYSA-N bis(oxiran-2-ylmethyl) cyclohex-4-ene-1,2-dicarboxylate Chemical compound C1C=CCC(C(=O)OCC2OC2)C1C(=O)OCC1CO1 KTPIWUHKYIJBCR-UHFFFAOYSA-N 0.000 description 2
- 230000003139 buffering effect Effects 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- 239000011353 cycloaliphatic epoxy resin Substances 0.000 description 2
- 230000007547 defect Effects 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- TYQCGQRIZGCHNB-JLAZNSOCSA-N l-ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(O)=C(O)C1=O TYQCGQRIZGCHNB-JLAZNSOCSA-N 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 239000004814 polyurethane Substances 0.000 description 2
- 238000004382 potting Methods 0.000 description 2
- 230000000630 rising effect Effects 0.000 description 2
- 229920002379 silicone rubber Polymers 0.000 description 2
- 239000004945 silicone rubber Substances 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- 239000004925 Acrylic resin Substances 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- 229930185605 Bisphenol Natural products 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical group CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 239000004841 bisphenol A epoxy resin Substances 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000004568 cement Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000013007 heat curing Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- VYKXQOYUCMREIS-UHFFFAOYSA-N methylhexahydrophthalic anhydride Chemical compound C1CCCC2C(=O)OC(=O)C21C VYKXQOYUCMREIS-UHFFFAOYSA-N 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000005304 optical glass Substances 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 230000005693 optoelectronics Effects 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 229920005749 polyurethane resin Polymers 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000007348 radical reaction Methods 0.000 description 1
- 238000003303 reheating Methods 0.000 description 1
- 230000008054 signal transmission Effects 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 150000004819 silanols Chemical class 0.000 description 1
- 239000002210 silicon-based material Substances 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- TXDNPSYEJHXKMK-UHFFFAOYSA-N sulfanylsilane Chemical compound S[SiH3] TXDNPSYEJHXKMK-UHFFFAOYSA-N 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 238000001029 thermal curing Methods 0.000 description 1
- 239000012745 toughening agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J171/00—Adhesives based on polyethers obtained by reactions forming an ether link in the main chain; Adhesives based on derivatives of such polymers
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J181/00—Adhesives based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing sulfur, with or without nitrogen, oxygen, or carbon only; Adhesives based on polysulfones; Adhesives based on derivatives of such polymers
- C09J181/02—Polythioethers; Polythioether-ethers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2203/00—Applications
- C08L2203/20—Applications use in electrical or conductive gadgets
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2205/00—Polymer mixtures characterised by other features
- C08L2205/03—Polymer mixtures characterised by other features containing three or more polymers in a blend
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Epoxy Resins (AREA)
Abstract
The invention relates to a special high-refraction high-transparency optical path adhesive for an optical communication device, which is characterized by comprising the following components: the catalyst comprises end-ring-oxygen-naphthyl fluorene polythioether alcohol, alicyclic epoxy resin, naphthyl fluorene polythioether alcohol, a latent amine catalyst, a thiol diluent, a photoinitiator and a stabilizer. The adhesive has extremely high refractive index, and meanwhile, the main structure of the resin, namely the naphthyl fluorene structure, endows the adhesive with high modulus and rigidity, and the polythioether alcohol endows the resin with flexibility, so that the adhesive is ensured to have good rigidity and flexibility, and can be applied to optical device linkage and bonding in optical communication.
Description
Technical Field
The invention belongs to the field of optical path glue, and particularly relates to a special high-refraction high-transparency optical path glue for an optical communication device, which can be applied to the optical communication industry.
Background
In the optical communication industry, optical glue with high refraction, high bonding strength and certain buffering performance is required, the glue not only plays a role in bonding and fixing, but also needs to play an optical signal transmission function in an optical device, and therefore the glue needs excellent optical performance, such as refractive index, transmittance, Abbe index and the like.
At present, the most studied high refractive index glues in the industry are organic silicon glues, for example, the invention patents in China, namely patent number ZL201210004141.1, entitled "high refractive index and high transparency organic silicon electronic potting adhesive, and preparation method and application thereof", are that olefinic silane and silanol compounds react with mercaptosilane oligomer precursors to obtain high refractive organic silicon gel. Chinese patent No. ZL200710001733.7 entitled "curable silicone rubber composition and cured product thereof" provides a curable silicone rubber composition that can form a cured product having improved hardness, no surface tackiness, a high refractive index, and rubber-like properties such as elongation without any loss, useful for electric, electronic or optoelectronic parts. The invention relates to a Chinese invention patent with the patent number of 201210307502.X and the name of high-refraction and high-adhesion high-power LED packaging organic silicon material and a chemical synthesis method thereof, which is prepared by using vinylphenyl polysiloxane, vinylphenyl silicone oil, a polysiloxane catalyst containing platinum and a tackifier; the component B comprises: the hydrogen-containing phenyl polysiloxane, the dihydro-terminated phenyl polysiloxane, the ethylene phenyl polysiloxane and the inhibitor effectively solve the contradiction between the strength and the cracking of the cured colloid. The invention can obtain refraction 1.54, is suitable for industrialization, and completely meets the requirements of high-power LED packaging. The invention also discloses a polyurethane and epoxy resin type high-refraction pouring sealant, for example, the invention patent of China with the patent number of ZL201610244889.7 and the name of ultraviolet light curing optical adhesive for glass optical devices and a preparation method thereof, wherein the high-refraction optical adhesive is prepared from sulfur-containing polyurethane, can be rapidly cured under ultraviolet light irradiation, has stronger bonding strength to glass base materials, and simultaneously has high refractive index which is more than or equal to 1.50, can meet the bonding and fixing requirements of the glass optical devices, and solves the defects of low refractive index and the like of the adhesive for the existing glass optical devices. The invention is a Chinese patent application with the patent application number of 201910255007.0 and the name of 'high-refractive index LED epoxy pouring sealant and a preparation method thereof', and the epoxy pouring sealant prepared by mixing low-halogen bisphenol A epoxy resin, a monomer containing sulfydryl or hydroxyl, a toughening agent, a diluent, methyl hexahydrophthalic anhydride, polyhydric alcohol, a curing accelerator and the like has high refractive index, transparency, low halogen, high temperature resistance, corrosion resistance and excellent mechanical properties in LED application.
The high refractive optical cement or potting adhesive mentioned in the above patent is mainly used in the LED packaging industry, and has no high requirements for purity, refractive index and reliability in the optical communication industry.
The optical path glue used in the current optical communication industry is mainly mastered by enterprises in the United states and Japan, and domestic optical path glue cannot be replaced for a while. The optical path glue is relatively less in use amount, but is very important in the field of optical devices, and the price of the optical path glue is comparable to that of gold. The optical path glue not only requires very high transparency, but also requires the refractive index to be more than 1.5, requires the refractive index to be more than 1.65 for part of special optical devices, and simultaneously requires the glue to be capable of being quickly cured, high in bonding strength and certain in buffering performance.
The shading index can be greatly improved to more than 1.7 at most according to Lorentz-Lorenz equation, benzene ring structure, biphenyl structure, naphthalene structure, S element and the like in the communication industry, and the shading index is close to optical glass. Although there are documents of high refractive optical materials reported in the industry, for example, chinese patent application No. 201410164091.2 entitled "composition for high refractive index and high strength optical material" uses an electrodeless compound of sulfur atom, and an episulfide compound and a xylylene sulfide compound react to prepare an optical lens material with a shading index of 1.73. The present application is a chinese patent application No. 2014800443845 entitled "polymerizable composition for high refractive index optical material and method for producing high refractive index optical material", which uses acrylic resin having bisphenol fluorene structure to prepare lens material with high refractive index by radical reaction.
Although the refractive index of the material is higher, the lens is mainly prepared by adopting an injection molding process, and the material is not light path glue suitable for being used in an optical device, and the existing light path glue has a space for further improvement and optimization along with the development of the optical device.
Disclosure of Invention
In order to overcome the defects of the prior art, the invention provides the high-refraction high-transparency light path adhesive, which ensures that the resin has a very high refractive index of more than 1.7, has good structural strength and flexibility, has high bonding strength and high reliability after being cured, and can be subjected to UV curing, heating curing and UV + heat dual curing.
In order to achieve the purpose, the technical scheme of the invention is realized by the following steps of: the high-performance liquid crystal display panel comprises end-ring-oxygen-naphthalene-fluorene polythioether alcohol, alicyclic epoxy resin, naphthyl-fluorene polythioether alcohol, a latent amine catalyst, a thiol diluent, a photoinitiator and a stabilizer, wherein the mass ratio of the end-ring-oxygen-naphthalene-fluorene polythioether alcohol to the alicyclic epoxy resin to the naphthyl-fluorene polythioether alcohol to the latent amine catalyst to the thiol diluent to the photoinitiator to the stabilizer is as follows: 1: 0.1-0.5: 0.8-1.2: 0.005-0.01: 0.1-0.5: 0.1-0.3: 0.001-0.005.
In the technical scheme, the synthesis method of the naphthyl fluorene polythioether alcohol comprises the following steps: mixing 9,9-Bis (6-hydroxy-2-naphthyl) fluorene, thiirane, an alkaline catalyst and a solvent A, raising the reaction temperature to 60-120 ℃, and reacting for 2-5 hours to obtain the naphthyl fluorene polythioether alcohol, wherein the mass ratio of the 9,9-Bis (6-hydroxy-2-naphthyl) fluorene, the thiirane, the alkaline catalyst and the solvent A is 1: 0.2-10: 0.01-0.05: 10-50 parts of; the chemical reaction equation is shown as the following formula:
wherein m + n =4-20;
the method for synthesizing the end-epoxy-group-terminated naphthyl fluorene polythioether alcohol comprises the steps of dissolving the naphthyl fluorene polythioether alcohol in a solvent A, adding epichlorohydrin and sodium hydroxide, raising the reaction temperature to 60-120 ℃, reacting for 1-3 hours, washing with water, and carrying out reduced pressure distillation and purification to obtain the naphthyl fluorene polythioether alcohol with epoxy groups; wherein the mass ratio of the naphthyl fluorene polythioether alcohol to the epichlorohydrin to the sodium hydroxide to the solvent A is 1: 0.5-5: 0.1-0.5: 10-20 parts of; the chemical reaction equation is shown as the following formula:
wherein m + n =4-20;
the alkaline catalyst is one or a mixture of more of triethylamine, ammonium carbonate, sodium carbonate, potassium carbonate and sodium hydroxide, and the solvent A is one or a mixture of more of formamide, N-methyl pyrrolidone, dimethyl sulfoxide, cyclohexanone, tetramethyl ethylenediamine or dioxane.
In the technical scheme, the alicyclic epoxy resin is one or a mixture of 3, 4-epoxycyclohexylmethyl 3, 4-epoxycyclohexyl formate, tetrahydrophthalic acid diglycidyl ester, bis ((3, 4-epoxycyclohexyl) methyl) adipate, poly [ (2-oxiranyl) -1, 2-cyclohexanediol ] 2-ethyl-2- (hydroxymethyl) -1, 3-propanediol ether (3:1) and cyclohexane-1, 2-dicarboxylic acid diglycidyl ester.
In the technical scheme, the latent amine catalyst is one or a mixture of more of 1, 8-diazabicyclo [ 5.4.0 ] undec-7-ene, 1, 4-diazabicyclo (2, 2, 2) octane, triethylamine, tetramethylguanidine, N-dimethyl-p-toluidine, dihydroxyethylaniline and dialkylaniline.
In the technical scheme, the mercaptan diluent is one or a mixture of more of trimethylolpropane tris (3-mercaptopropionate), pentaerythritol tetrakis (3-mercaptopropionate) or isooctyl 3-mercaptopropionate.
In the technical scheme, the stabilizer is one or a mixture of more of barbituric acid, triphenyl phosphate, salicylic acid, tartaric acid, citric acid, ascorbic acid, trihydroxybenzoic acid or parabanic acid.
In the technical scheme, the photoinitiator is one or a mixture of 2,2' -bis (2-bromo-5-methoxyphenyl) -4,4' -5,5' -tetraphenyl-diimidazole or 2-hydroxy-methylphenylpropane-1-ketone.
Compared with the prior art, the invention has the following advantages and beneficial effects:
1. the invention develops naphthyl fluorene polythiol and naphthyl fluorene polythioether alcohol, which contain a large amount of high-refraction sulfur elements, benzene rings (each molecule contains 6 benzene rings), naphthalene groups and the like, and ensure that the resin has extremely high refractive index which is more than 1.7;
2. the invention develops a monomer of naphthyl fluorene polythioether alcohol and end-ring-oxygen naphthyl fluorene polythioether alcohol, wherein naphthyl fluorene has a rigid structure, and the naphthyl fluorene has a flexible structure, so that the adhesive based on the resin system has good structural strength and flexibility at the same time.
3. The naphthyl fluorene polythioether alcohol and the end-ring-oxygen naphthyl fluorene polythioether alcohol are subjected to cross-linking curing reaction by utilizing the chemical reaction between mercaptan and epoxy under the catalysis of an amino catalyst, finally realize curing cross-linking, and ensure high bonding strength and high reliability of the glue after curing.
4. The high-refractive-index high-light-transmittance road adhesive can be cured by UV, can be cured by heating, and can be cured by UV and heat. The glue can be fully cured under various complex conditions and various application conditions.
Detailed Description
The present invention will be described in further detail with reference to examples, but the embodiments of the present invention are not limited thereto.
Example one
(1) Synthesis of naphthyl fluorene polythioether alcohol
Adding 9,9-Bis (6-hydroxy-2-naphthyl) fluorene (CAS number: 934557-66-1), thiirane, an alkaline catalyst and a solvent A together, reacting at 60 ℃ for 2 hours to obtain the naphthyl fluorene polythioether alcohol, wherein the mass ratio of the 9,9-Bis (6-hydroxy-2-naphthyl) fluorene, the thiirane, the alkaline catalyst and the solvent A is 1: 0.2: 0.01: 10; the chemical reaction equation is shown as the following formula:
wherein m + n = 4;
wherein the basic catalyst is triethylamine, and the solvent A is formamide.
(2) Synthesis of naphthyl fluorene polythioether alcohol with terminal epoxy group
Dissolving naphthyl fluorene polythioether alcohol in a solvent A, adding epoxy chloropropane and sodium hydroxide, raising the reaction temperature to 60 ℃, reacting for 1 hour, washing with water, and carrying out reduced pressure distillation and purification to obtain the naphthyl fluorene polythioether alcohol with an epoxy group; wherein the mass ratio of the naphthyl fluorene polythioether alcohol to the epichlorohydrin to the sodium hydroxide to the solvent A is 1: 0.5: 0.1: 10; the chemical reaction equation is shown as the following formula:
wherein m + n = 4;
(3) preparation of high-refraction high-transparency light path adhesive
Mixing the end-ring-oxygen-naphthyl fluorene polythioether alcohol, alicyclic epoxy resin, naphthyl fluorene polythioether alcohol, a latent amine catalyst, a thiol diluent, a photoinitiator and a stabilizer to obtain the high-refraction high-transparency optical path adhesive. Wherein the mass ratio of the end-ring-oxygen-naphthyl fluorene polythioether alcohol, the alicyclic epoxy resin, the naphthyl fluorene polythioether alcohol, the latent amine catalyst, the mercaptan diluent, the photoinitiator and the stabilizer is as follows: 1: 0.1: 0.8: 0.005: 0.1: 0.1: 0.001;
the alicyclic epoxy resin is 3, 4-epoxycyclohexylmethyl 3, 4-epoxycyclohexyl formate, and the type of the alicyclic epoxy resin is CAS: 2386-87-0; the latent amine catalyst is 1, 8-diazabicyclo [ 5.4.0 ]; the mercaptan diluent is trimethylolpropane tri (3-mercaptopropionate) with the model of CAS: 33007-83-9; the stabilizer is barbituric acid; the photoinitiator is 2,2' -bis (2-bromo-5-methoxyphenyl) -4,4' -5,5' -tetraphenyl-diimidazole (M-HABI).
Example two
(1) Synthesis of naphthyl fluorene polythioether alcohol
Adding 9,9-Bis (6-hydroxy-2-naphthyl) fluorene (CAS number: 934557-66-1), thiirane, an alkaline catalyst and a solvent A together, reacting at 120 ℃ for 5 hours to obtain the naphthyl fluorene polythioether alcohol, wherein the mass ratio of the 9,9-Bis (6-hydroxy-2-naphthyl) fluorene, the thiirane, the alkaline catalyst and the solvent A is 1: 10: 0.05: 50; the chemical reaction equation is shown as the following formula:
wherein m + n = 20;
the alkaline catalyst is sodium hydroxide. The solvent A is dioxane.
(2) Synthesis of naphthyl fluorene polythioether alcohol with terminal epoxy group
Dissolving naphthyl fluorene polythioether alcohol in a solvent A, adding epoxy chloropropane and sodium hydroxide, raising the reaction temperature to 120 ℃, reacting for 3 hours, washing with water, and carrying out reduced pressure distillation and purification to obtain the naphthyl fluorene polythioether alcohol with an epoxy group; wherein the mass ratio of the naphthyl fluorene polythioether alcohol to the epichlorohydrin to the sodium hydroxide to the solvent A is 1: 5: 0.5: 20; the chemical reaction equation is shown as the following formula:
wherein m + n = 20.
(3) Preparation of high-refraction high-transparency light path adhesive
Mixing the end-ring-oxygen-naphthyl fluorene polythioether alcohol, alicyclic epoxy resin, naphthyl fluorene polythioether alcohol, a latent amine catalyst, a thiol diluent, a photoinitiator and a stabilizer to obtain the high-refraction high-transparency optical path adhesive, wherein the mass ratio of the end-ring-oxygen-naphthyl fluorene polythioether alcohol, the alicyclic epoxy resin, the naphthyl fluorene polythioether alcohol, the latent amine catalyst, the thiol diluent, the photoinitiator and the stabilizer is as follows: 1: 0.5: 1.2: 0.01: 0.5: 0.3: 0.005.
the alicyclic epoxy resin is diglycidyl tetrahydrophthalate, and the type of the alicyclic epoxy resin is CAS: 21544-03-6; the latent amine catalyst is dimethylaniline; the mercaptan diluent is isooctyl 3-mercaptopropionate, and the model is CAS: 30374-01-7; the stabilizer is parabanic acid; the photoinitiator is 2-hydroxy-methyl phenyl propane-1-ketone.
EXAMPLE III
(1) Synthesis of naphthyl fluorene polythioether alcohol
Adding 9,9-Bis (6-hydroxy-2-naphthyl) fluorene (CAS number: 934557-66-1), thiirane, an alkaline catalyst and a solvent A together, reacting at 100 ℃ for 3 hours to obtain naphthyl fluorene polythioether alcohol; wherein the mass ratio of the 9,9-Bis (6-hydroxy-2-naphthyl) fluorene to the thiirane to the alkaline catalyst to the solvent A is 1: 10: 0.05: 50; the chemical reaction equation is shown as the following formula:
wherein m + n = 10;
the alkaline catalyst is sodium carbonate and the solvent A is cyclohexanone.
(2) Synthesis of naphthyl fluorene polythioether alcohol with terminal epoxy group
Dissolving naphthyl fluorene polythioether alcohol in a solvent A, adding epoxy chloropropane and sodium hydroxide, raising the reaction temperature to 100 ℃, reacting for 2 hours, washing with water, and carrying out reduced pressure distillation and purification to obtain the naphthyl fluorene polythioether alcohol with an epoxy group; wherein the mass ratio of the naphthyl fluorene polythioether alcohol to the epichlorohydrin to the sodium hydroxide to the solvent A is 1: 3: 0.3: 12; the chemical reaction equation is shown as the following formula:
wherein m + n = 10.
(3) Preparation of high-refraction high-transparency light path adhesive
Mixing end-ring-epoxy-naphthyl-fluorene polythioether alcohol, alicyclic epoxy resin, naphthyl-fluorene polythioether alcohol, a latent amine catalyst, a thiol diluent, a photoinitiator and a stabilizer to obtain the high-refraction high-transparency optical path adhesive; wherein the end-ring-oxygen-naphthyl fluorene polythioether alcohol, alicyclic epoxy resin, naphthyl fluorene polythioether alcohol, latent amine catalyst, thiol diluent and photoinitiator; the mass ratio of the stabilizer is as follows: 1: 0.4: 1: 0.008: 0.3: 0.2: 0.004;
the cycloaliphatic epoxy resin is poly [ (2-oxiranyl) -1, 2-cyclohexanediol ] 2-ethyl-2- (hydroxymethyl) -1, 3-propanediol ether (3:1) with the type CAS: 244772-00-7; the latent amine catalyst is triethylamine; the mercaptan diluent is isooctyl 3-mercaptopropionate, and the model is CAS: 30374-01-7; the stabilizer is trihydroxybenzoic acid; the photoinitiator is 2-hydroxy-methyl phenyl propane-1-ketone.
Example four
(1) Synthesis of naphthyl fluorene polythioether alcohol
Adding 9,9-Bis (6-hydroxy-2-naphthyl) fluorene (CAS number: 934557-66-1), thiirane, an alkaline catalyst and a solvent A together, reacting at 80 ℃ for 4 hours to obtain the naphthyl fluorene polythioether alcohol, wherein the mass ratio of the 9,9-Bis (6-hydroxy-2-naphthyl) fluorene to the thiirane to the alkaline catalyst is 1: 5: 0.03: 25; the chemical reaction equation is shown as the following formula:
wherein m + n = 18;
the alkaline catalyst is potassium carbonate, and the solvent A is dimethyl sulfoxide.
(2) Synthesis of naphthyl fluorene polythioether alcohol with terminal epoxy group
Dissolving naphthyl fluorene polythioether alcohol in a solvent A, adding epoxy chloropropane and sodium hydroxide, raising the reaction temperature to 100 ℃, reacting for 2.5 hours, washing with water, and carrying out reduced pressure distillation and purification to obtain the naphthyl fluorene polythioether alcohol with an epoxy group; wherein the mass ratio of the naphthyl fluorene polythioether alcohol to the epichlorohydrin to the sodium hydroxide to the solvent A is 1: 3: 0.35: 15; the chemical reaction equation is shown as the following formula:
wherein m + n = 18.
(3) Preparation of high-refraction high-transparency light path adhesive
Mixing the end-ring-oxygen-naphthyl fluorene polythioether alcohol, alicyclic epoxy resin, naphthyl fluorene polythioether alcohol, a latent amine catalyst, a thiol diluent, a photoinitiator and a stabilizer to obtain the high-refraction high-transparency optical path adhesive, wherein the mass ratio of the end-ring-oxygen-naphthyl fluorene polythioether alcohol, the alicyclic epoxy resin, the naphthyl fluorene polythioether alcohol, the latent amine catalyst, the thiol diluent, the photoinitiator and the stabilizer is as follows: 1: 0.35: 1.1: 0.009: 0.45: 0.25: 0.004;
the cycloaliphatic epoxy resin is cyclohexane-1, 2-dicarboxylic acid diglycidyl ester, the type of which is CAS: 5493-45-8; the latent amine catalyst is Tetramethylguanidine (TMG); the mercaptan diluent is pentaerythritol tetrakis (3-mercaptopropionate) with the model CAS: 7575-23-7; the stabilizer is triphenyl phosphate; the photoinitiator is 2-hydroxy-methyl phenyl propane-1-ketone.
EXAMPLE five
(1) Synthesis of naphthyl fluorene polythioether alcohol
Adding 9,9-Bis (6-hydroxy-2-naphthyl) fluorene (CAS number: 934557-66-1), thiirane, an alkaline catalyst and a solvent A together, reacting at 90 ℃ for 4 hours to obtain naphthyl fluorene polythioether alcohol; wherein the mass ratio of the 9,9-Bis (6-hydroxy-2-naphthyl) fluorene to the thiirane to the alkaline catalyst to the solvent A is 1: 7: 0.03: 30, of a nitrogen-containing gas; the chemical reaction equation is shown as the following formula:
wherein m + n = 10;
the alkaline catalyst is potassium carbonate, and the solvent A is tetramethylethylenediamine.
(2) Synthesis of naphthyl fluorene polythioether alcohol with terminal epoxy group
Dissolving naphthyl fluorene polythioether alcohol in a solvent A, adding epoxy chloropropane and sodium hydroxide, raising the reaction temperature to 100 ℃, reacting for 2.5 hours, washing with water, and carrying out reduced pressure distillation and purification to obtain the naphthyl fluorene polythioether alcohol with an epoxy group; wherein the mass ratio of the naphthyl fluorene polythioether alcohol to the epichlorohydrin to the sodium hydroxide to the solvent A is 1: 3: 0.35: 15; the chemical reaction equation is shown as the following formula:
wherein m + n = 10.
(3) Preparation of high-refraction high-transparency light path adhesive
Mixing the end-ring-epoxy-naphthyl-fluorene polythioether alcohol, alicyclic epoxy resin, naphthyl fluorene polythioether alcohol, a latent amine catalyst, a thiol diluent, a photoinitiator and a stabilizer to obtain the high-refraction high-transparency optical path adhesive. Wherein the end-ring-oxygen-naphthyl fluorene polythioether alcohol, alicyclic epoxy resin, naphthyl fluorene polythioether alcohol, a latent amine catalyst, a mercaptan diluent, a photoinitiator and a stabilizer are in the following mass ratio: 1: 0.35: 0.9: 0.009: 0.35: 0.25: 0.002;
the alicyclic epoxy resin is cyclohexane-1, 2-dicarboxylic acid diglycidyl ester, and the type of the alicyclic epoxy resin is CAS: 5493-45-8; the latent amine catalyst is dihydroxyethyl aniline; the mercaptan diluent is isooctyl 3-mercaptopropionate, and the model is CAS: 30374-01-7; the stabilizer is ascorbic acid; the photoinitiator is 2-hydroxy-methyl phenyl propane-1-ketone.
The high-refractive index and high-transparency optical path adhesive obtained in the first to fifth embodiments is applied to an optical device for optical communication, and the curing method thereof may be UV curing, or thermal curing or UV reheating first.
The UV light curing conditions are as follows: the LED 365 or 405nm wave band and the power of 200-2Irradiating for 10-40 s; the heat curing conditions were: the temperature is 70-100 deg.C, and the time is 30-60 min.
The optical path glues prepared in the first to fifth examples were subjected to application testing, and the performance testing parameters are shown in table 1 below. And (3) viscosity testing: and the viscosity of the glue is tested by a rotary viscometer by referring to GB/T22235-2008.
Tg point test: DMA test is adopted, the frequency is 1Hz, the temperature rising speed is 10 ℃/min, and the temperature rising range is 25-400 ℃.
CTE test: the linear expansion coefficient was measured by TMA test with reference to JIS K7197, 10mm by 25mm test specimen, and heating rate 50 ℃/min.
And (3) testing the refractive index: with reference to GB 7962.11-2010-T, refractive index tests of the hardened coatings were performed.
And (3) transparency test: the transmittance test is carried out by referring to GB T2410-2008;
elongation at break and modulus test: referring to the method for preparing the sample in GB-T30776-. The elongation at break reflects the flexibility of the material to a certain extent, and the modulus reflects the rigidity of the material to a certain extent.
The above embodiments are preferred embodiments of the present invention, but the present invention is not limited to the above embodiments, and any other changes, modifications, substitutions, combinations, and simplifications which do not depart from the spirit and principle of the present invention should be construed as equivalents thereof, and all such changes, modifications, substitutions, combinations, and simplifications are intended to be included in the scope of the present invention.
Claims (6)
1. A special high-refraction high-transparency optical path adhesive for optical communication devices is characterized by comprising the following components: the high-performance liquid crystal display panel comprises end-ring-oxygen-naphthalene-fluorene polythioether alcohol, alicyclic epoxy resin, naphthyl-fluorene polythioether alcohol, a latent amine catalyst, a thiol diluent, a photoinitiator and a stabilizer, wherein the mass ratio of the end-ring-oxygen-naphthalene-fluorene polythioether alcohol to the alicyclic epoxy resin to the naphthyl-fluorene polythioether alcohol to the latent amine catalyst to the thiol diluent to the photoinitiator to the stabilizer is as follows: 1: 0.1-0.5: 0.8-1.2: 0.005-0.01: 0.1-0.5: 0.1-0.3: 0.001-0.005;
the synthesis method of the naphthyl fluorene polythioether alcohol comprises the following steps: mixing 9,9-Bis (6-hydroxy-2-naphthyl) fluorene, thiirane, an alkaline catalyst and a solvent A, raising the reaction temperature to 60-120 ℃, and reacting for 2-5 hours to obtain the naphthyl fluorene polythioether alcohol, wherein the mass ratio of the 9,9-Bis (6-hydroxy-2-naphthyl) fluorene, the thiirane, the alkaline catalyst and the solvent A is 1: 0.2-10: 0.01-0.05: 10-50 parts of; the chemical reaction equation is shown as the following formula:
wherein m + n =4-20;
the method for synthesizing the end-epoxy-group-terminated naphthyl fluorene polythioether alcohol comprises the steps of dissolving the naphthyl fluorene polythioether alcohol in a solvent A, adding epichlorohydrin and sodium hydroxide, raising the reaction temperature to 60-120 ℃, reacting for 1-3 hours, washing with water, and carrying out reduced pressure distillation and purification to obtain the naphthyl fluorene polythioether alcohol with epoxy groups; wherein the mass ratio of the naphthyl fluorene polythioether alcohol to the epichlorohydrin to the sodium hydroxide to the solvent A is 1: 0.5-5: 0.1-0.5: 10-20 parts of; the chemical reaction equation is shown as the following formula:
wherein m + n =4-20;
the alkaline catalyst is one or a mixture of more of triethylamine, ammonium carbonate, sodium carbonate, potassium carbonate and sodium hydroxide, and the solvent A is one or a mixture of more of formamide, N-methyl pyrrolidone, dimethyl sulfoxide, cyclohexanone, tetramethylethylenediamine and dioxane.
2. The special high-refraction high-transparency optical-path adhesive for optical communication devices according to claim 1, wherein the alicyclic epoxy resin is one or a mixture of 3, 4-epoxycyclohexylmethyl 3, 4-epoxycyclohexyl formate, diglycidyl tetrahydrophthalate, bis ((3, 4-epoxycyclohexyl) methyl) adipate, poly [ (2-oxiranyl) -1, 2-cyclohexanediol ] 2-ethyl-2- (hydroxymethyl) -1, 3-propanediol ether (3:1) and diglycidyl cyclohexane-1, 2-dicarboxylate.
3. The special high-refraction high-transparency optical-path adhesive for optical communication devices according to claim 1, wherein the latent amine catalyst is one or a mixture of 1, 8-diazabicyclo [ 5.4.0 ] undec-7-ene, 1, 4-diazabicyclo (2, 2, 2) octane, triethylamine, tetramethylguanidine, N-dimethyl-p-toluidine, dihydroxyethylaniline and dialkylaniline.
4. The special high-refraction high-transparency optical path adhesive for optical communication devices according to claim 1, wherein the thiol diluent is one or more of trimethylolpropane tri (3-mercaptopropionate), pentaerythritol tetrakis (3-mercaptopropionate), or isooctyl 3-mercaptopropionate.
5. The special high-refraction high-transparency optical path adhesive for optical communication devices as claimed in claim 1, wherein the stabilizer is one or more of barbituric acid, triphenyl phosphate, salicylic acid, tartaric acid, citric acid, ascorbic acid, trihydroxybenzoic acid or parabanic acid.
6. The special high-refraction high-transparency optical path adhesive for optical communication devices as claimed in claim 1, wherein the photoinitiator is one or more of 2,2' -bis (2-bromo-5-methoxyphenyl) -4,4' -5,5' -tetraphenyl-diimidazole or 2-hydroxy-methylphenylpropane-1-one.
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