CN114075122A - 一种亲水性偶氮化合物及其用途 - Google Patents
一种亲水性偶氮化合物及其用途 Download PDFInfo
- Publication number
- CN114075122A CN114075122A CN202010823974.5A CN202010823974A CN114075122A CN 114075122 A CN114075122 A CN 114075122A CN 202010823974 A CN202010823974 A CN 202010823974A CN 114075122 A CN114075122 A CN 114075122A
- Authority
- CN
- China
- Prior art keywords
- azo compound
- polymer
- blue light
- acrylate
- materials
- 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.)
- Granted
Links
- -1 azo compound Chemical class 0.000 title claims abstract description 54
- 239000000463 material Substances 0.000 claims abstract description 49
- 229920000642 polymer Polymers 0.000 claims abstract description 34
- 239000002537 cosmetic Substances 0.000 claims abstract description 8
- 238000000576 coating method Methods 0.000 claims abstract description 5
- 150000001875 compounds Chemical class 0.000 claims description 29
- 239000000178 monomer Substances 0.000 claims description 24
- 239000002202 Polyethylene glycol Substances 0.000 claims description 21
- 229920001223 polyethylene glycol Polymers 0.000 claims description 21
- 238000001914 filtration Methods 0.000 claims description 19
- 239000006096 absorbing agent Substances 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 239000003999 initiator Substances 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- 239000003431 cross linking reagent Substances 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 239000011737 fluorine Substances 0.000 claims description 4
- 150000002431 hydrogen Chemical group 0.000 claims description 4
- 239000012567 medical material Substances 0.000 claims description 4
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000003827 glycol group Chemical group 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000006232 ethoxy propyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 2
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 claims description 2
- 239000000976 ink Substances 0.000 claims description 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 239000005060 rubber Substances 0.000 claims description 2
- 125000003107 substituted aryl group Chemical group 0.000 claims description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 239000006097 ultraviolet radiation absorber Substances 0.000 claims description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims 1
- 210000000554 iris Anatomy 0.000 claims 1
- 230000005693 optoelectronics Effects 0.000 claims 1
- 239000007858 starting material Substances 0.000 claims 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims 1
- 229920002554 vinyl polymer Polymers 0.000 claims 1
- 230000031700 light absorption Effects 0.000 abstract description 10
- 230000000052 comparative effect Effects 0.000 description 14
- 238000002834 transmittance Methods 0.000 description 13
- 238000004140 cleaning Methods 0.000 description 10
- 230000002209 hydrophobic effect Effects 0.000 description 10
- 231100000135 cytotoxicity Toxicity 0.000 description 9
- 230000003013 cytotoxicity Effects 0.000 description 9
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 8
- 230000003595 spectral effect Effects 0.000 description 8
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 7
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 7
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical group COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 6
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Substances CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 239000002861 polymer material Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 description 5
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- DBCAQXHNJOFNGC-UHFFFAOYSA-N 4-bromo-1,1,1-trifluorobutane Chemical compound FC(F)(F)CCCBr DBCAQXHNJOFNGC-UHFFFAOYSA-N 0.000 description 4
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 4
- 238000004090 dissolution Methods 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 238000001228 spectrum Methods 0.000 description 4
- NUXLDNTZFXDNBA-UHFFFAOYSA-N 6-bromo-2-methyl-4h-1,4-benzoxazin-3-one Chemical compound C1=C(Br)C=C2NC(=O)C(C)OC2=C1 NUXLDNTZFXDNBA-UHFFFAOYSA-N 0.000 description 3
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 3
- 239000012964 benzotriazole Substances 0.000 description 3
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 3
- KBLWLMPSVYBVDK-UHFFFAOYSA-N cyclohexyl prop-2-enoate Chemical compound C=CC(=O)OC1CCCCC1 KBLWLMPSVYBVDK-UHFFFAOYSA-N 0.000 description 3
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 description 3
- 239000010408 film Substances 0.000 description 3
- 230000001988 toxicity Effects 0.000 description 3
- 231100000419 toxicity Toxicity 0.000 description 3
- PSGCQDPCAWOCSH-UHFFFAOYSA-N (4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl) prop-2-enoate Chemical compound C1CC2(C)C(OC(=O)C=C)CC1C2(C)C PSGCQDPCAWOCSH-UHFFFAOYSA-N 0.000 description 2
- FPZWZCWUIYYYBU-UHFFFAOYSA-N 2-(2-ethoxyethoxy)ethyl acetate Chemical group CCOCCOCCOC(C)=O FPZWZCWUIYYYBU-UHFFFAOYSA-N 0.000 description 2
- DAVVKEZTUOGEAK-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethyl 2-methylprop-2-enoate Chemical compound COCCOCCOC(=O)C(C)=C DAVVKEZTUOGEAK-UHFFFAOYSA-N 0.000 description 2
- XFCMNSHQOZQILR-UHFFFAOYSA-N 2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOC(=O)C(C)=C XFCMNSHQOZQILR-UHFFFAOYSA-N 0.000 description 2
- FWWXYLGCHHIKNY-UHFFFAOYSA-N 2-ethoxyethyl prop-2-enoate Chemical compound CCOCCOC(=O)C=C FWWXYLGCHHIKNY-UHFFFAOYSA-N 0.000 description 2
- ILZXXGLGJZQLTR-UHFFFAOYSA-N 2-phenylethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCC1=CC=CC=C1 ILZXXGLGJZQLTR-UHFFFAOYSA-N 0.000 description 2
- HPSGLFKWHYAKSF-UHFFFAOYSA-N 2-phenylethyl prop-2-enoate Chemical compound C=CC(=O)OCCC1=CC=CC=C1 HPSGLFKWHYAKSF-UHFFFAOYSA-N 0.000 description 2
- KUDUQBURMYMBIJ-UHFFFAOYSA-N 2-prop-2-enoyloxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOC(=O)C=C KUDUQBURMYMBIJ-UHFFFAOYSA-N 0.000 description 2
- JHWGFJBTMHEZME-UHFFFAOYSA-N 4-prop-2-enoyloxybutyl prop-2-enoate Chemical compound C=CC(=O)OCCCCOC(=O)C=C JHWGFJBTMHEZME-UHFFFAOYSA-N 0.000 description 2
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- OKKRPWIIYQTPQF-UHFFFAOYSA-N Trimethylolpropane trimethacrylate Chemical compound CC(=C)C(=O)OCC(CC)(COC(=O)C(C)=C)COC(=O)C(C)=C OKKRPWIIYQTPQF-UHFFFAOYSA-N 0.000 description 2
- 239000002250 absorbent Substances 0.000 description 2
- 230000002745 absorbent Effects 0.000 description 2
- 230000004075 alteration Effects 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical group C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 210000004087 cornea Anatomy 0.000 description 2
- 238000012937 correction Methods 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- GMSCBRSQMRDRCD-UHFFFAOYSA-N dodecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCOC(=O)C(C)=C GMSCBRSQMRDRCD-UHFFFAOYSA-N 0.000 description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 2
- 239000007943 implant Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000013508 migration Methods 0.000 description 2
- 230000005012 migration Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 208000001491 myopia Diseases 0.000 description 2
- 230000004379 myopia Effects 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- BOQSSGDQNWEFSX-UHFFFAOYSA-N propan-2-yl 2-methylprop-2-enoate Chemical compound CC(C)OC(=O)C(C)=C BOQSSGDQNWEFSX-UHFFFAOYSA-N 0.000 description 2
- 210000001525 retina Anatomy 0.000 description 2
- 239000012453 solvate Substances 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 238000010998 test method Methods 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- BWTMTZBMAGYMOD-UHFFFAOYSA-N (2,2,3,3,4,4,5,5-octafluoro-6-prop-2-enoyloxyhexyl) prop-2-enoate Chemical compound C=CC(=O)OCC(F)(F)C(F)(F)C(F)(F)C(F)(F)COC(=O)C=C BWTMTZBMAGYMOD-UHFFFAOYSA-N 0.000 description 1
- LGPAKRMZNPYPMG-UHFFFAOYSA-N (3-hydroxy-2-prop-2-enoyloxypropyl) prop-2-enoate Chemical compound C=CC(=O)OC(CO)COC(=O)C=C LGPAKRMZNPYPMG-UHFFFAOYSA-N 0.000 description 1
- IMNBHNRXUAJVQE-UHFFFAOYSA-N (4-benzoyl-3-hydroxyphenyl) 2-methylprop-2-enoate Chemical compound OC1=CC(OC(=O)C(=C)C)=CC=C1C(=O)C1=CC=CC=C1 IMNBHNRXUAJVQE-UHFFFAOYSA-N 0.000 description 1
- NOBYOEQUFMGXBP-UHFFFAOYSA-N (4-tert-butylcyclohexyl) (4-tert-butylcyclohexyl)oxycarbonyloxy carbonate Chemical compound C1CC(C(C)(C)C)CCC1OC(=O)OOC(=O)OC1CCC(C(C)(C)C)CC1 NOBYOEQUFMGXBP-UHFFFAOYSA-N 0.000 description 1
- FMQPBWHSNCRVQJ-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-yl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(C(F)(F)F)C(F)(F)F FMQPBWHSNCRVQJ-UHFFFAOYSA-N 0.000 description 1
- MYWOJODOMFBVCB-UHFFFAOYSA-N 1,2,6-trimethylphenanthrene Chemical compound CC1=CC=C2C3=CC(C)=CC=C3C=CC2=C1C MYWOJODOMFBVCB-UHFFFAOYSA-N 0.000 description 1
- VDYWHVQKENANGY-UHFFFAOYSA-N 1,3-Butyleneglycol dimethacrylate Chemical compound CC(=C)C(=O)OC(C)CCOC(=O)C(C)=C VDYWHVQKENANGY-UHFFFAOYSA-N 0.000 description 1
- HOQBNIVJRDBYIG-UHFFFAOYSA-N 1,3-diethoxypropan-2-yl 2-methylprop-2-enoate Chemical compound CCOCC(COCC)OC(=O)C(C)=C HOQBNIVJRDBYIG-UHFFFAOYSA-N 0.000 description 1
- UTKGUZSDIUZTIW-UHFFFAOYSA-N 1,3-diethoxypropan-2-yl prop-2-enoate Chemical compound CCOCC(COCC)OC(=O)C=C UTKGUZSDIUZTIW-UHFFFAOYSA-N 0.000 description 1
- OJBFUNPJMOYSOQ-UHFFFAOYSA-N 1,3-dimethoxypropan-2-yl 2-methylprop-2-enoate Chemical compound COCC(COC)OC(=O)C(C)=C OJBFUNPJMOYSOQ-UHFFFAOYSA-N 0.000 description 1
- WDEIYXBQLBYVBO-UHFFFAOYSA-N 1,3-dimethoxypropan-2-yl prop-2-enoate Chemical compound COCC(COC)OC(=O)C=C WDEIYXBQLBYVBO-UHFFFAOYSA-N 0.000 description 1
- JXJPJSFDICMAFP-UHFFFAOYSA-N 1,3-diphenoxypropan-2-yl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(COC1=CC=CC=C1)COC1=CC=CC=C1 JXJPJSFDICMAFP-UHFFFAOYSA-N 0.000 description 1
- XUVCISVDXYDUTO-UHFFFAOYSA-N 1,3-diphenoxypropan-2-yl prop-2-enoate Chemical compound C=1C=CC=CC=1OCC(OC(=O)C=C)COC1=CC=CC=C1 XUVCISVDXYDUTO-UHFFFAOYSA-N 0.000 description 1
- VNQXSTWCDUXYEZ-UHFFFAOYSA-N 1,7,7-trimethylbicyclo[2.2.1]heptane-2,3-dione Chemical compound C1CC2(C)C(=O)C(=O)C1C2(C)C VNQXSTWCDUXYEZ-UHFFFAOYSA-N 0.000 description 1
- PZIQHPMKQHKTEI-UHFFFAOYSA-N 1-phenylpropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(CC)C1=CC=CC=C1 PZIQHPMKQHKTEI-UHFFFAOYSA-N 0.000 description 1
- KCDCJGROIOFZCN-UHFFFAOYSA-N 1-phenylpropyl prop-2-enoate Chemical compound C=CC(=O)OC(CC)C1=CC=CC=C1 KCDCJGROIOFZCN-UHFFFAOYSA-N 0.000 description 1
- QEDJMOONZLUIMC-UHFFFAOYSA-N 1-tert-butyl-4-ethenylbenzene Chemical compound CC(C)(C)C1=CC=C(C=C)C=C1 QEDJMOONZLUIMC-UHFFFAOYSA-N 0.000 description 1
- QRIMLDXJAPZHJE-UHFFFAOYSA-N 2,3-dihydroxypropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(O)CO QRIMLDXJAPZHJE-UHFFFAOYSA-N 0.000 description 1
- OWPUOLBODXJOKH-UHFFFAOYSA-N 2,3-dihydroxypropyl prop-2-enoate Chemical compound OCC(O)COC(=O)C=C OWPUOLBODXJOKH-UHFFFAOYSA-N 0.000 description 1
- WFTWWOCWRSUGAW-UHFFFAOYSA-N 2-(2-ethoxyethoxy)ethyl 2-methylprop-2-enoate Chemical compound CCOCCOCCOC(=O)C(C)=C WFTWWOCWRSUGAW-UHFFFAOYSA-N 0.000 description 1
- FTALTLPZDVFJSS-UHFFFAOYSA-N 2-(2-ethoxyethoxy)ethyl prop-2-enoate Chemical compound CCOCCOCCOC(=O)C=C FTALTLPZDVFJSS-UHFFFAOYSA-N 0.000 description 1
- RWXMAAYKJDQVTF-UHFFFAOYSA-N 2-(2-hydroxyethoxy)ethyl prop-2-enoate Chemical compound OCCOCCOC(=O)C=C RWXMAAYKJDQVTF-UHFFFAOYSA-N 0.000 description 1
- HZMXJTJBSWOCQB-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethyl prop-2-enoate Chemical compound COCCOCCOC(=O)C=C HZMXJTJBSWOCQB-UHFFFAOYSA-N 0.000 description 1
- JJBFVQSGPLGDNX-UHFFFAOYSA-N 2-(2-methylprop-2-enoyloxy)propyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(C)COC(=O)C(C)=C JJBFVQSGPLGDNX-UHFFFAOYSA-N 0.000 description 1
- GJKGAPPUXSSCFI-UHFFFAOYSA-N 2-Hydroxy-4'-(2-hydroxyethoxy)-2-methylpropiophenone Chemical compound CC(C)(O)C(=O)C1=CC=C(OCCO)C=C1 GJKGAPPUXSSCFI-UHFFFAOYSA-N 0.000 description 1
- WYGWHHGCAGTUCH-UHFFFAOYSA-N 2-[(2-cyano-4-methylpentan-2-yl)diazenyl]-2,4-dimethylpentanenitrile Chemical compound CC(C)CC(C)(C#N)N=NC(C)(C#N)CC(C)C WYGWHHGCAGTUCH-UHFFFAOYSA-N 0.000 description 1
- RBFPEAGEJJSYCX-UHFFFAOYSA-N 2-[2-(2-ethoxyethoxy)ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CCOCCOCCOCCOC(=O)C(C)=C RBFPEAGEJJSYCX-UHFFFAOYSA-N 0.000 description 1
- WPDXVLVDHUDHPC-UHFFFAOYSA-N 2-[2-(2-ethoxyethoxy)ethoxy]ethyl prop-2-enoate Chemical compound CCOCCOCCOCCOC(=O)C=C WPDXVLVDHUDHPC-UHFFFAOYSA-N 0.000 description 1
- VETIYACESIPJSO-UHFFFAOYSA-N 2-[2-(2-hydroxyethoxy)ethoxy]ethyl prop-2-enoate Chemical compound OCCOCCOCCOC(=O)C=C VETIYACESIPJSO-UHFFFAOYSA-N 0.000 description 1
- NMLCFUMBGQIRJX-UHFFFAOYSA-N 2-[2-(2-methoxyethoxy)ethoxy]ethyl prop-2-enoate Chemical compound COCCOCCOCCOC(=O)C=C NMLCFUMBGQIRJX-UHFFFAOYSA-N 0.000 description 1
- HWSSEYVMGDIFMH-UHFFFAOYSA-N 2-[2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOCCOC(=O)C(C)=C HWSSEYVMGDIFMH-UHFFFAOYSA-N 0.000 description 1
- VCYCUECVHJJFIQ-UHFFFAOYSA-N 2-[3-(benzotriazol-2-yl)-4-hydroxyphenyl]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCC1=CC=C(O)C(N2N=C3C=CC=CC3=N2)=C1 VCYCUECVHJJFIQ-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
- IJOUWMMZJISKHY-UHFFFAOYSA-N 2-hydroxypropan-2-yl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(C)(C)O IJOUWMMZJISKHY-UHFFFAOYSA-N 0.000 description 1
- OLPSPGUBQWMHJZ-UHFFFAOYSA-N 2-hydroxypropan-2-yl prop-2-enoate Chemical compound CC(C)(O)OC(=O)C=C OLPSPGUBQWMHJZ-UHFFFAOYSA-N 0.000 description 1
- CTHJQRHPNQEPAB-UHFFFAOYSA-N 2-methoxyethenylbenzene Chemical compound COC=CC1=CC=CC=C1 CTHJQRHPNQEPAB-UHFFFAOYSA-N 0.000 description 1
- YXYJVFYWCLAXHO-UHFFFAOYSA-N 2-methoxyethyl 2-methylprop-2-enoate Chemical compound COCCOC(=O)C(C)=C YXYJVFYWCLAXHO-UHFFFAOYSA-N 0.000 description 1
- HFCUBKYHMMPGBY-UHFFFAOYSA-N 2-methoxyethyl prop-2-enoate Chemical compound COCCOC(=O)C=C HFCUBKYHMMPGBY-UHFFFAOYSA-N 0.000 description 1
- RUMACXVDVNRZJZ-UHFFFAOYSA-N 2-methylpropyl 2-methylprop-2-enoate Chemical compound CC(C)COC(=O)C(C)=C RUMACXVDVNRZJZ-UHFFFAOYSA-N 0.000 description 1
- CFVWNXQPGQOHRJ-UHFFFAOYSA-N 2-methylpropyl prop-2-enoate Chemical compound CC(C)COC(=O)C=C CFVWNXQPGQOHRJ-UHFFFAOYSA-N 0.000 description 1
- CEXQWAAGPPNOQF-UHFFFAOYSA-N 2-phenoxyethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOC1=CC=CC=C1 CEXQWAAGPPNOQF-UHFFFAOYSA-N 0.000 description 1
- RZVINYQDSSQUKO-UHFFFAOYSA-N 2-phenoxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOC1=CC=CC=C1 RZVINYQDSSQUKO-UHFFFAOYSA-N 0.000 description 1
- KHJAQZWRONYRPZ-UHFFFAOYSA-N 2-phenylpropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(C)C1=CC=CC=C1 KHJAQZWRONYRPZ-UHFFFAOYSA-N 0.000 description 1
- FNIWUDWOOTVEKP-UHFFFAOYSA-N 2-phenylpropyl prop-2-enoate Chemical compound C=CC(=O)OCC(C)C1=CC=CC=C1 FNIWUDWOOTVEKP-UHFFFAOYSA-N 0.000 description 1
- KXYAVSFOJVUIHT-UHFFFAOYSA-N 2-vinylnaphthalene Chemical compound C1=CC=CC2=CC(C=C)=CC=C21 KXYAVSFOJVUIHT-UHFFFAOYSA-N 0.000 description 1
- HTWRFCRQSLVESJ-UHFFFAOYSA-N 3-(2-methylprop-2-enoyloxy)propyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCOC(=O)C(C)=C HTWRFCRQSLVESJ-UHFFFAOYSA-N 0.000 description 1
- GNSFRPWPOGYVLO-UHFFFAOYSA-N 3-hydroxypropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCO GNSFRPWPOGYVLO-UHFFFAOYSA-N 0.000 description 1
- QZPSOSOOLFHYRR-UHFFFAOYSA-N 3-hydroxypropyl prop-2-enoate Chemical compound OCCCOC(=O)C=C QZPSOSOOLFHYRR-UHFFFAOYSA-N 0.000 description 1
- FQMIAEWUVYWVNB-UHFFFAOYSA-N 3-prop-2-enoyloxybutyl prop-2-enoate Chemical compound C=CC(=O)OC(C)CCOC(=O)C=C FQMIAEWUVYWVNB-UHFFFAOYSA-N 0.000 description 1
- GFLJTEHFZZNCTR-UHFFFAOYSA-N 3-prop-2-enoyloxypropyl prop-2-enoate Chemical compound C=CC(=O)OCCCOC(=O)C=C GFLJTEHFZZNCTR-UHFFFAOYSA-N 0.000 description 1
- BESKSSIEODQWBP-UHFFFAOYSA-N 3-tris(trimethylsilyloxy)silylpropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCC[Si](O[Si](C)(C)C)(O[Si](C)(C)C)O[Si](C)(C)C BESKSSIEODQWBP-UHFFFAOYSA-N 0.000 description 1
- XOJWAAUYNWGQAU-UHFFFAOYSA-N 4-(2-methylprop-2-enoyloxy)butyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCCOC(=O)C(C)=C XOJWAAUYNWGQAU-UHFFFAOYSA-N 0.000 description 1
- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 description 1
- SAPGBCWOQLHKKZ-UHFFFAOYSA-N 6-(2-methylprop-2-enoyloxy)hexyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCCCCOC(=O)C(C)=C SAPGBCWOQLHKKZ-UHFFFAOYSA-N 0.000 description 1
- NQSLZEHVGKWKAY-UHFFFAOYSA-N 6-methylheptyl 2-methylprop-2-enoate Chemical compound CC(C)CCCCCOC(=O)C(C)=C NQSLZEHVGKWKAY-UHFFFAOYSA-N 0.000 description 1
- DXPPIEDUBFUSEZ-UHFFFAOYSA-N 6-methylheptyl prop-2-enoate Chemical compound CC(C)CCCCCOC(=O)C=C DXPPIEDUBFUSEZ-UHFFFAOYSA-N 0.000 description 1
- FIHBHSQYSYVZQE-UHFFFAOYSA-N 6-prop-2-enoyloxyhexyl prop-2-enoate Chemical compound C=CC(=O)OCCCCCCOC(=O)C=C FIHBHSQYSYVZQE-UHFFFAOYSA-N 0.000 description 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
- COCLLEMEIJQBAG-UHFFFAOYSA-N 8-methylnonyl 2-methylprop-2-enoate Chemical compound CC(C)CCCCCCCOC(=O)C(C)=C COCLLEMEIJQBAG-UHFFFAOYSA-N 0.000 description 1
- LVGFPWDANALGOY-UHFFFAOYSA-N 8-methylnonyl prop-2-enoate Chemical compound CC(C)CCCCCCCOC(=O)C=C LVGFPWDANALGOY-UHFFFAOYSA-N 0.000 description 1
- OZAIFHULBGXAKX-VAWYXSNFSA-N AIBN Substances N#CC(C)(C)\N=N\C(C)(C)C#N OZAIFHULBGXAKX-VAWYXSNFSA-N 0.000 description 1
- UUEYEUDSRFNIQJ-UHFFFAOYSA-N CCOC(N)=O.CCOC(N)=O.CC(=C)C(O)=O.CC(=C)C(O)=O Chemical compound CCOC(N)=O.CCOC(N)=O.CC(=C)C(O)=O.CC(=C)C(O)=O UUEYEUDSRFNIQJ-UHFFFAOYSA-N 0.000 description 1
- 102100026735 Coagulation factor VIII Human genes 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 208000010412 Glaucoma Diseases 0.000 description 1
- 101000911390 Homo sapiens Coagulation factor VIII Proteins 0.000 description 1
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 1
- JFZHPFOXAAIUMB-UHFFFAOYSA-N Phenylethylmalonamide Chemical compound CCC(C(N)=O)(C(N)=O)C1=CC=CC=C1 JFZHPFOXAAIUMB-UHFFFAOYSA-N 0.000 description 1
- DAKWPKUUDNSNPN-UHFFFAOYSA-N Trimethylolpropane triacrylate Chemical compound C=CC(=O)OCC(CC)(COC(=O)C=C)COC(=O)C=C DAKWPKUUDNSNPN-UHFFFAOYSA-N 0.000 description 1
- IAXXETNIOYFMLW-COPLHBTASA-N [(1s,3s,4s)-4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl] 2-methylprop-2-enoate Chemical compound C1C[C@]2(C)[C@@H](OC(=O)C(=C)C)C[C@H]1C2(C)C IAXXETNIOYFMLW-COPLHBTASA-N 0.000 description 1
- XXRPVRKDBVYBAT-UHFFFAOYSA-N [2,2,3,3,4,4-hexafluoro-5-(2-methylprop-2-enoyloxy)hexyl] 2-methylprop-2-enoate Chemical compound C(C(=C)C)(=O)OCC(C(C(C(C)OC(C(=C)C)=O)(F)F)(F)F)(F)F XXRPVRKDBVYBAT-UHFFFAOYSA-N 0.000 description 1
- UHPPAPGGMSFXNF-UHFFFAOYSA-N [2-hydroxy-3-[[propyl-bis(trimethylsilyloxy)silyl]methoxy]propyl] 2-methylprop-2-enoate Chemical compound CCC[Si](O[Si](C)(C)C)(O[Si](C)(C)C)COCC(O)COC(=O)C(C)=C UHPPAPGGMSFXNF-UHFFFAOYSA-N 0.000 description 1
- UKMBKKFLJMFCSA-UHFFFAOYSA-N [3-hydroxy-2-(2-methylprop-2-enoyloxy)propyl] 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(CO)OC(=O)C(C)=C UKMBKKFLJMFCSA-UHFFFAOYSA-N 0.000 description 1
- GUCYFKSBFREPBC-UHFFFAOYSA-N [phenyl-(2,4,6-trimethylbenzoyl)phosphoryl]-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C(=O)C1=C(C)C=C(C)C=C1C GUCYFKSBFREPBC-UHFFFAOYSA-N 0.000 description 1
- DMLAVOWQYNRWNQ-UHFFFAOYSA-N azobenzene Chemical compound C1=CC=CC=C1N=NC1=CC=CC=C1 DMLAVOWQYNRWNQ-UHFFFAOYSA-N 0.000 description 1
- CHIHQLCVLOXUJW-UHFFFAOYSA-N benzoic anhydride Chemical compound C=1C=CC=CC=1C(=O)OC(=O)C1=CC=CC=C1 CHIHQLCVLOXUJW-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 description 1
- AOJOEFVRHOZDFN-UHFFFAOYSA-N benzyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC1=CC=CC=C1 AOJOEFVRHOZDFN-UHFFFAOYSA-N 0.000 description 1
- GCTPMLUUWLLESL-UHFFFAOYSA-N benzyl prop-2-enoate Chemical compound C=CC(=O)OCC1=CC=CC=C1 GCTPMLUUWLLESL-UHFFFAOYSA-N 0.000 description 1
- 229930006711 bornane-2,3-dione Natural products 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- YQHLDYVWEZKEOX-UHFFFAOYSA-N cumene hydroperoxide Chemical compound OOC(C)(C)C1=CC=CC=C1 YQHLDYVWEZKEOX-UHFFFAOYSA-N 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
- 238000002784 cytotoxicity assay Methods 0.000 description 1
- 231100000263 cytotoxicity test Toxicity 0.000 description 1
- GTBGXKPAKVYEKJ-UHFFFAOYSA-N decyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCOC(=O)C(C)=C GTBGXKPAKVYEKJ-UHFFFAOYSA-N 0.000 description 1
- FWLDHHJLVGRRHD-UHFFFAOYSA-N decyl prop-2-enoate Chemical compound CCCCCCCCCCOC(=O)C=C FWLDHHJLVGRRHD-UHFFFAOYSA-N 0.000 description 1
- 125000004386 diacrylate group Chemical group 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- VFHVQBAGLAREND-UHFFFAOYSA-N diphenylphosphoryl-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 VFHVQBAGLAREND-UHFFFAOYSA-N 0.000 description 1
- OCDWICPYKQMQSQ-UHFFFAOYSA-N docosyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCCCCCCCCCCCOC(=O)C(C)=C OCDWICPYKQMQSQ-UHFFFAOYSA-N 0.000 description 1
- KHAYCTOSKLIHEP-UHFFFAOYSA-N docosyl prop-2-enoate Chemical compound CCCCCCCCCCCCCCCCCCCCCCOC(=O)C=C KHAYCTOSKLIHEP-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- CCOSOBKLKCHGNO-UHFFFAOYSA-N ethoxy-(2,4,6-trimethylbenzoyl)phosphinic acid Chemical compound C(C)OP(O)(=O)C(C1=C(C=C(C=C1C)C)C)=O CCOSOBKLKCHGNO-UHFFFAOYSA-N 0.000 description 1
- 231100001156 grade 3 toxicity Toxicity 0.000 description 1
- PAIQEFSJYGYULU-UHFFFAOYSA-N heptadecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCCCCCCOC(=O)C(C)=C PAIQEFSJYGYULU-UHFFFAOYSA-N 0.000 description 1
- KVILQFSLJDTWPU-UHFFFAOYSA-N heptadecyl prop-2-enoate Chemical compound CCCCCCCCCCCCCCCCCOC(=O)C=C KVILQFSLJDTWPU-UHFFFAOYSA-N 0.000 description 1
- LNCPIMCVTKXXOY-UHFFFAOYSA-N hexyl 2-methylprop-2-enoate Chemical compound CCCCCCOC(=O)C(C)=C LNCPIMCVTKXXOY-UHFFFAOYSA-N 0.000 description 1
- LNMQRPPRQDGUDR-UHFFFAOYSA-N hexyl prop-2-enoate Chemical compound CCCCCCOC(=O)C=C LNMQRPPRQDGUDR-UHFFFAOYSA-N 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- 150000002433 hydrophilic molecules Chemical class 0.000 description 1
- 238000002513 implantation Methods 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 229940119545 isobornyl methacrylate Drugs 0.000 description 1
- PBOSTUDLECTMNL-UHFFFAOYSA-N lauryl acrylate Chemical compound CCCCCCCCCCCCOC(=O)C=C PBOSTUDLECTMNL-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 231100001224 moderate toxicity Toxicity 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- AJDUTMFFZHIJEM-UHFFFAOYSA-N n-(9,10-dioxoanthracen-1-yl)-4-[4-[[4-[4-[(9,10-dioxoanthracen-1-yl)carbamoyl]phenyl]phenyl]diazenyl]phenyl]benzamide Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2NC(=O)C(C=C1)=CC=C1C(C=C1)=CC=C1N=NC(C=C1)=CC=C1C(C=C1)=CC=C1C(=O)NC1=CC=CC2=C1C(=O)C1=CC=CC=C1C2=O AJDUTMFFZHIJEM-UHFFFAOYSA-N 0.000 description 1
- PNLUGRYDUHRLOF-UHFFFAOYSA-N n-ethenyl-n-methylacetamide Chemical compound C=CN(C)C(C)=O PNLUGRYDUHRLOF-UHFFFAOYSA-N 0.000 description 1
- RQAKESSLMFZVMC-UHFFFAOYSA-N n-ethenylacetamide Chemical compound CC(=O)NC=C RQAKESSLMFZVMC-UHFFFAOYSA-N 0.000 description 1
- 231100001083 no cytotoxicity Toxicity 0.000 description 1
- NZIDBRBFGPQCRY-UHFFFAOYSA-N octyl 2-methylprop-2-enoate Chemical compound CCCCCCCCOC(=O)C(C)=C NZIDBRBFGPQCRY-UHFFFAOYSA-N 0.000 description 1
- ANISOHQJBAQUQP-UHFFFAOYSA-N octyl prop-2-enoate Chemical compound CCCCCCCCOC(=O)C=C ANISOHQJBAQUQP-UHFFFAOYSA-N 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- FZUGPQWGEGAKET-UHFFFAOYSA-N parbenate Chemical compound CCOC(=O)C1=CC=C(N(C)C)C=C1 FZUGPQWGEGAKET-UHFFFAOYSA-N 0.000 description 1
- QIWKUEJZZCOPFV-UHFFFAOYSA-N phenyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1=CC=CC=C1 QIWKUEJZZCOPFV-UHFFFAOYSA-N 0.000 description 1
- WRAQQYDMVSCOTE-UHFFFAOYSA-N phenyl prop-2-enoate Chemical compound C=CC(=O)OC1=CC=CC=C1 WRAQQYDMVSCOTE-UHFFFAOYSA-N 0.000 description 1
- 229920001483 poly(ethyl methacrylate) polymer Polymers 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- FBCQUCJYYPMKRO-UHFFFAOYSA-N prop-2-enyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC=C FBCQUCJYYPMKRO-UHFFFAOYSA-N 0.000 description 1
- QTECDUFMBMSHKR-UHFFFAOYSA-N prop-2-enyl prop-2-enoate Chemical compound C=CCOC(=O)C=C QTECDUFMBMSHKR-UHFFFAOYSA-N 0.000 description 1
- LYBIZMNPXTXVMV-UHFFFAOYSA-N propan-2-yl prop-2-enoate Chemical compound CC(C)OC(=O)C=C LYBIZMNPXTXVMV-UHFFFAOYSA-N 0.000 description 1
- NHARPDSAXCBDDR-UHFFFAOYSA-N propyl 2-methylprop-2-enoate Chemical compound CCCOC(=O)C(C)=C NHARPDSAXCBDDR-UHFFFAOYSA-N 0.000 description 1
- PNXMTCDJUBJHQJ-UHFFFAOYSA-N propyl prop-2-enoate Chemical compound CCCOC(=O)C=C PNXMTCDJUBJHQJ-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 231100000004 severe toxicity Toxicity 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- SJMYWORNLPSJQO-UHFFFAOYSA-N tert-butyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(C)(C)C SJMYWORNLPSJQO-UHFFFAOYSA-N 0.000 description 1
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
- KEROTHRUZYBWCY-UHFFFAOYSA-N tridecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCCOC(=O)C(C)=C KEROTHRUZYBWCY-UHFFFAOYSA-N 0.000 description 1
- XOALFFJGWSCQEO-UHFFFAOYSA-N tridecyl prop-2-enoate Chemical compound CCCCCCCCCCCCCOC(=O)C=C XOALFFJGWSCQEO-UHFFFAOYSA-N 0.000 description 1
- 238000000870 ultraviolet spectroscopy Methods 0.000 description 1
- 239000001043 yellow dye Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C245/00—Compounds containing chains of at least two nitrogen atoms with at least one nitrogen-to-nitrogen multiple bond
- C07C245/02—Azo compounds, i.e. compounds having the free valencies of —N=N— groups attached to different atoms, e.g. diazohydroxides
- C07C245/06—Azo compounds, i.e. compounds having the free valencies of —N=N— groups attached to different atoms, e.g. diazohydroxides with nitrogen atoms of azo groups bound to carbon atoms of six-membered aromatic rings
- C07C245/08—Azo compounds, i.e. compounds having the free valencies of —N=N— groups attached to different atoms, e.g. diazohydroxides with nitrogen atoms of azo groups bound to carbon atoms of six-membered aromatic rings with the two nitrogen atoms of azo groups bound to carbon atoms of six-membered aromatic rings, e.g. azobenzene
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/20—Esters of polyhydric alcohols or phenols, e.g. 2-hydroxyethyl (meth)acrylate or glycerol mono-(meth)acrylate
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
- C08F220/30—Esters containing oxygen in addition to the carboxy oxygen containing aromatic rings in the alcohol moiety
- C08F220/301—Esters containing oxygen in addition to the carboxy oxygen containing aromatic rings in the alcohol moiety and one oxygen in the alcohol moiety
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Materials For Medical Uses (AREA)
Abstract
本发明提出了一种亲水性偶氮化合物及其用途,以及包含所述偶氮化合物的聚合物及用途。该苯偶氮化合物具备优异的亲水性、蓝光吸收功能和生物相容性,且包含可聚合基团,不易在聚合物中发生迁移、溶出和扩散,可用于眼科材料、化妆品材料和涂料等材料。
Description
技术领域
本发明涉及一种亲水性(甲基)丙烯酸酯类型的偶氮化合物,适合用于制备蓝光过滤眼镜材料、蓝光过滤型隐形眼镜材料、蓝光过滤型人工晶状体材料、光电子薄膜、化妆品和功能丙烯酸酯涂料材料。
背景技术
偶氮化合物可以吸收蓝光使化合物本身显黄色,既可以作为蓝光吸收剂用于制备具有蓝光吸收功能的材料,又能作为黄色染料用于制备需要颜色调控的材料。小分子偶氮化合物通常具有一定的生物毒性,通过物理混合填充到材料中将从材料中扩散、迁移或溶解,将降低材料的蓝光吸收功能稳定性,降低材料的颜色稳定和产生生物安全性隐患。而含有(甲基)丙烯酸酯官能化的偶氮化合物可以与其它可聚合单体共聚形成稳定的聚合物材料,所以偶氮单体不会从材料中扩散迁移,使材料保持稳定的蓝光吸收能力、保持颜色稳定性和生物安全性。蓝光对视网膜造成损伤已经越来越受到关注,用蓝光吸收剂制备的光电子屏幕蓝光过滤膜、蓝光过滤眼镜、蓝光过滤隐形眼镜材料和蓝光过滤型眼科植入物可以保护眼内视网膜受到蓝光的损伤。然而目前使用的蓝光吸收剂大部分为疏水性蓝光吸收剂,而亲水性的蓝光吸收剂种类较少,限制了在亲水性的蓝光过滤材料以及在湿性环境下材料中的应用,所以非常有必要发展具有亲水性的蓝光吸收剂,另外提高蓝光吸收剂的生物安全性有利于拓展其在生物医用材料中的应用。
发明内容
本发明提出一种包含聚乙二醇烷氧基结构的(甲基)丙烯酸酯类型的偶氮化合物,具备蓝光吸收功能和可聚合性质,所述偶氮化合物可以与其它可聚合单体共聚以共价键的方式形成聚合物材料,使偶氮化合物能稳定存在于材料中,降低偶氮化合物从材料中迁移扩散或溶解。
另外,本发明提出的偶氮化合物,通过引入亲水性的烷氧基和聚乙二醇片段增强化合物的本体亲水性,可以增强与其它亲水性(甲基)丙烯酸酯单体或化合物的相容性,拓展在亲水材料以及在水性环境下使用的聚合物材料的用途,特别地适合用于制备蓝光过滤眼镜、蓝光过滤隐形眼镜材料、蓝光过滤近视矫正眼内植入物、蓝光过滤型人工晶状体、功能光电材料、化妆品和涂料。另外,结构中包含的聚乙二醇片段又能使材料具有良好的生物安全性。
一方面,本发明提出一种亲水性偶氮化合物,其为式(a)所示化合物或为式(a)所示化合物的立体异构体、几何异构体、互变异构体、对映异构体、氮氧化物、水合物、溶剂化物,
其中:
R1为氢或烷基;
n=1-500;
R2为氢或烷基;
R3、R4、R5、R6、R7、R8、R9、R10和R11分别独立地为氢、氟、氯、溴、碘、羟基、氨基、硝基、氰基、烷基、烷氧基、芳香基或取代芳香基。
在一些实施方案中,式(a)中的R1为氢或甲基。
在一些实施方案中,式(a)中的R2为甲基、乙基或正丙基。
在一些实施方案中,式(a)中的n等于1、2、3或4,或聚乙二醇片段相对分子量范围选自200至20000。
在一些实施方案中,式(a)中的R3、R4、R5、R6、R7、R8、R9、R10和R11分别独立地为氢、氟、氯、溴、碘、-OH、-NH2、甲基、乙基、正丙基、异丙基、正丁基、异丁基、叔丁基、甲氧基、乙氧基、正丙氧基、异丙氧基、正丁氧基、异丁氧基、正己氧基、甲氧基甲基、甲氧基乙基、乙氧基甲基、乙氧基乙基、乙氧基丙基、苯基和苯氧基。
以通式(a)表示的本发明的偶氮化合物没有特别限定,然而作为优选实施例可以优选具有以下结构的化合物:
或它们的立体异构体、几何异构体、互变异构体、对映异构体、氮氧化物、水合物以及溶剂化物。满足以上式(1)至式(26)所示通式的化合物具有较为理想的蓝光吸收功能,可作为蓝光吸收剂使用,即可降低材料对蓝光的透过率,化合物中的聚乙二醇烷氧基结构单元既可以增强化合物的亲水性,增强与亲水单体的相容性,又不影响化合物与疏水单体的相容性,上述所述偶氮单体化合物既可以在其它亲水性单体中溶解,也可以在其它疏水性单体中溶解。此外,聚乙二醇具有良好的生物相容性,上述化合物结构中包含的聚乙二醇结构有利于提高化合物的生物相容性。本发明提出的偶氮化合物带有可聚合性的(甲基)丙烯酸酯基团,可与其它可聚合单体发生共聚反应形成共价键连接,如此不会出现偶氮化合物从聚合物中迁移、溶出的现象。
本发明的另一方面提出一种聚合物,构成所述聚合物的原料包括本体单体和蓝光吸收剂,所述蓝光吸收剂即本发明提出的偶氮化合物,上述偶氮化合物既能与亲水单体共聚,又能与疏水单体共聚,也能与亲水和疏水单体同时共聚,获得具有蓝光过滤效果的亲水或疏水眼科医用材料,而且偶氮化合物不会从聚合物材料中迁移扩散。上述聚合物可用于蓝光过滤型眼镜、蓝光过滤型隐形眼镜材料、蓝光过滤矫正近视植入材料、蓝光过滤型人工晶状体、蓝光过滤型光电子薄膜、化妆品和涂料材料。
在本发明的实施方案中,构成上述聚合物所述的疏水单体选自如下化合物至少之一:甲基丙烯酸甲酯、丙烯酸甲酯、甲基丙烯酸乙酯、丙烯酸乙酯、甲基丙烯酸正丙酯、丙烯酸正丙酯、甲基丙烯酸异丙酯、丙烯酸异丙酯、甲基丙烯酸正丁酯、丙烯酸正丁酯、甲基丙烯酸异丁酯、丙烯酸异丁酯、甲基丙烯酸叔丁酯、丙烯酸叔丁酯、甲基丙烯酸正己酯、丙烯酸正己酯、甲基丙烯酸正辛酯、丙烯酸正辛酯、甲基丙烯酸异辛酯、丙烯酸异辛酯、甲基丙烯酸正癸酯、丙烯酸正癸酯、甲基丙烯酸异癸酯、丙烯酸异癸酯、甲基丙烯酸月桂酯、丙烯酸月桂酯、甲基丙烯酸十三烷基酯、丙烯酸十三烷基酯、甲基丙烯酸十七烷基酯、丙烯酸十七烷基酯、甲基丙烯酸二十二烷基酯、丙烯酸二十二烷基酯、甲基丙烯酸环己酯、丙烯酸环己酯、甲基丙烯酸异冰片酯、丙烯酸异冰片酯、甲基丙烯酸-2-甲氧基乙基酯、丙烯酸-2-甲氧基乙基酯、甲基丙烯酸-2-乙氧基乙基酯、丙烯酸-2-乙氧基乙基酯、甲基丙烯酸-2-(2-甲氧基乙氧基)乙基酯、丙烯酸-2-(2-甲氧基乙氧基)乙基酯、甲基丙烯酸-2-(2-乙氧基乙氧基)乙基酯、丙烯酸-2-(2-乙氧基乙氧基)乙基酯、甲基丙烯酸-2-[2-(2-甲氧基乙氧基)乙氧基]乙基酯、丙烯酸-2-[2-(2-甲氧基乙氧基)乙氧基]乙基酯、甲基丙烯酸-2-[2-(2-乙氧基乙氧基)乙氧基]乙基酯、丙烯酸-2-[2-(2-乙氧基乙氧基)乙氧基]乙基酯、1,3-二甲氧基-2-丙醇甲基丙烯酸酯、1,3-二甲氧基-2-丙醇丙烯酸酯、1,3-二乙氧基-2-丙醇甲基丙烯酸酯、1,3-二乙氧基-2-丙醇丙烯酸酯、甲基丙烯酸苯基酯、丙烯酸苯基酯、甲基丙烯酸苯甲醇酯、丙烯酸苯甲醇酯、2-苯基乙基甲基丙烯酸酯、2-苯基乙基丙烯酸酯、甲基丙烯酸-2-苯氧乙酯、丙烯酸-2-苯氧乙酯、1-苯基-1-丙醇甲基丙烯酸酯、1-苯基-1-丙醇丙烯酸酯、2-苯基-1-丙醇甲基丙烯酸酯、2-苯基-1-丙醇丙烯酸酯、1,3-二苯氧基-2-丙醇甲基丙烯酸酯、1,3-二苯氧基-2-丙醇丙烯酸酯、1,3-二苯甲氧基-2-丙醇甲基丙烯酸酯、1,3-二苯甲氧基-2-丙醇丙烯酸酯、苯乙烯、甲基苯乙烯、甲氧基苯乙烯、4-叔丁基苯乙烯、2-乙烯基萘、甲基丙稀酸六氟异丙酯和甲基丙烯酰氧丙基三(三甲基硅氧烷基)硅烷。
在本发明的实施方案中,构成上述聚合物上述所述的亲水单体选自如下化合物至少之一:甲基丙烯酸羟基乙酯、丙烯酸羟基乙酯、甲基丙烯酸羟基正丙酯、丙烯酸羟基正丙酯、甲基丙烯酸羟基异丙酯、丙烯酸羟基异丙酯、甲基丙烯酸甘油酯、丙烯酸甘油酯、1-乙烯基-2-吡咯烷酮、甲氧基封端聚乙二醇甲基丙烯酸酯(聚乙二醇分子量1000至20000)、甲氧基封端聚乙二醇丙烯酸酯(聚乙二醇分子量1000至20000)、乙氧基封端聚乙二醇甲基丙烯酸酯(聚乙二醇分子量1000至20000)、乙氧基封端聚乙二醇丙烯酸酯(聚乙二醇分子量1000至20000)、甲基丙烯酸γ-甲氧基-β-羟丙酯、丙烯酸γ-甲氧基-β-羟丙酯、甲基丙烯酸γ-乙氧基-β-羟丙酯、丙烯酸γ-乙氧基-β-羟丙酯、甲基丙烯酸γ-丙氧基-β-羟丙酯和丙烯酸γ-丙氧基-β-羟丙酯、、N,N-二甲基丙烯酰胺、N-甲基-N-乙烯基乙酰胺、N-乙烯基乙酰胺和[3-(甲基丙烯酰氧基)-2-羟基丙氧基]丙基双(三甲基硅氧基)甲基硅烷。
构成上述提出的聚合物原料中,还可以进一步包括交联剂、紫外吸收剂和引发剂。在本发明的实施方案中,交联剂包括但不限于甲基丙烯酸烯丙酯、丙烯酸烯丙酯、乙二醇二甲基丙烯酸酯、乙二醇二丙烯酸酯、二甲基丙烯酸二甘醇酯、丙烯酸二甘醇酯、二甲基丙烯酸三甘醇酯、丙烯酸三甘醇酯、聚乙二醇二甲基丙烯酸酯(聚乙二醇分子量200至20000)、聚乙二醇二丙烯酸酯(聚乙二醇分子量200至20000)、1,3-丙二醇二甲基丙烯酸酯、1,3-丙二醇二丙烯酸酯、1,3-丁二醇二甲基丙烯酸酯、1,3-丁二醇二丙烯酸酯、1,4-丁二醇二甲基丙烯酸酯、1,4-丁二醇二丙烯酸酯、1,6-己二醇二甲基丙烯酸酯、1,6-己二醇二丙烯酸酯、二甲基丙烯酸甘油酯、二丙烯酸甘油酯、三羟甲基丙烷三甲基丙烯酸酯、季戊四醇四丙烯酸酯、二脲烷基二甲基丙烯酸酯、1,5-二(甲基丙烯酰氧基)-2,2,3,3,4,4-六氟己烷以及1,6-二(丙烯酰氧基)-2,2,3,3,4,4,5,5-八氟己烷的至少之一。紫外吸收剂为包含苯并三唑结构或苯甲酮结构的可共聚的化合物,紫外吸收剂包括但不限于2-(2'-羟基-3'-甲代烯丙基-5'-甲基苯基)苯并三唑、2-[2-羟基-5-[2-(甲基丙烯酰氧)乙基]苯基]-2H-苯并三唑、2-(3-烯丙基-2-羟基-5-甲基苯基)-2H-苯并三唑、2-羟基-4-(甲基丙烯酰氧基)二苯甲酮和2-丙烯酸2-(4-苯甲酰-3-羟基苯氧基)乙基酯。;引发剂包括热引发剂和光引发剂,热引发剂包括但不限于氧化苯甲酰、叔丁基过氧化氢、异丙苯基过氧化氢、双(4-叔丁基环己基)过氧化二碳酸酯、偶氮二异丁腈以及偶氮双(2,4-二甲基戊腈)的至少之一;光引发剂包括但不限于2,4,6-三甲基苯甲酰基-二苯基氧化膦、苯基双(2,4,6-三甲基苯甲酰基)氧化膦、2,4,6-三甲基苯甲酰基膦酸乙酯、樟脑醌、二苯甲酮、4-二甲基氨基苯甲酸乙酯和2-羟基-4'-(2-羟乙氧基)-2-甲基苯丙酮的至少之一。
在本发明中,基于合成聚合物所用单体的总重量,本发明所述偶氮化合物的用量可以为0.001%-10%重量,优选0.001%-3%;交联剂的用量可以为0.1%~10%重量,优选1-6%重量;紫外吸收剂用量可以为0.1%-5%重量,优选0.1-2%重量;引发剂的用量可以为0.1%-5%重量,优选0.1%-1%重量。
本发明提出的可聚合的偶氮化合物在蓝光线(波长400-480nm范围)具有优良的吸收特性,而本发明提出的聚合物包含具备上述性能的偶氮化合物,因此,本发明的聚合物同样在波长400-480nm范围区域具有优良的吸收性能,可以通过表征聚合物材料在光谱450nm和480nm处的透过率说明材料的蓝光吸收能力,材料在波长450nm和480nm出光谱透过率越低则说明材料对蓝光吸收越多。此外,本发明提出的偶氮化合物带有亲水性的聚乙二醇烷氧基结构片段,可增强其亲水性,使化合物既能与亲水化合物相容,又能与疏水化合物相容,增强其在亲水材料和疏水材料中的应用范围,另外可以调节偶氮化合物中聚乙二醇结构片段的分子量调节其结构的柔顺性以及提高生物相容性,使本发明的偶氮化合物可应用于医用材料中,非常适合用于制作特定功能的眼部医疗器件以及用于亲水性的化妆品中。
上述眼部医疗器件可以用于人工晶状体体、眼内透镜、接触透镜、角膜修正物、角膜内透镜、角膜嵌入物、角膜环或青光眼滤光装置等材料制备。更为优选地,可将本发明的聚合物作为亲水性人工晶体、疏水性人工晶状体、隐形眼镜和化妆品的材料。
在本发明的又一方面,本发明所提出的偶氮化合物及其聚合物,除了可将其添加到制作眼部医疗器件和化妆品的材料中外,还可以将其添加至涂料、油墨、橡胶或树脂材料中,使上述材料具备蓝光吸收功能或者调节颜色的功能。
具体实施方式
在本说明书的描述中,除非另外说明,本发明所使用的所有科技术语具有与本发明所属领域技术人员的通常理解相同的含义。本发明涉及的所有专利和公开出版物通过引用方式整体并入本发明。术语“包含”或“包括”为开放式表达,即包括本发明所指明的内容,但并不排除其他方面的内容。在本发明中,无论是否使用“大约”或“约”等字眼,所有在此公开了的数字均为近似值。每一个数字的数值有可能会出现10%以下的差异或者本领域人员认为的合理的差异,如1%、2%、3%、4%或5%的差异。下面将结合实施例对本发明的方案进行解释。本领域技术人员将会理解,下面的实施例仅用于说明本发明,而不应视为限定本发明的范围,本领域的普通技术人员在本发明的范围内可以对所述实施方案和实施例进行变化、修改、替换和变型。实施例中未注明具体技术或条件的,按照本领域内的文献所描述的技术或条件或者按照产品说明书进行。本发明上述偶氮化合物均可使用本领域已知的有机合成方法制备得到,特别地,在本发明中上述偶氮化合物由委托外部供应商定制购买得到。
实施例1偶氮化合物的亲水性及其比较
分别考察偶氮化合物在水中和亲水单体甲基丙烯羟乙酯中的溶解情况。具体方法:在单口瓶中加入10mL水或甲基丙烯酸羟乙酯,然后加入1g偶氮化合物,超声溶解五分钟混合均匀再静置10分钟,然后观察溶液情况。溶液显示黄色澄清,瓶底无沉淀,则说明易溶解,记录溶解性A级;溶液显示黄色澄清,瓶底只有少量沉淀,则说明大部分溶解,记录溶解性B级;溶液显示黄色澄清,瓶底有大量沉淀,则说明少部分溶解,记录溶解性C级;溶液只显示浑浊或固体全部沉入底部,则说明难熔解,记录溶解性D级,上述溶解性能力排序为A级>B级>C级>D级,对比化合物为D-1、D-2、D-3和D-4,结果如下表1所示。
表1:
对比化合物结构说明
实施例2聚合物P-1、P-2、P-3、P-4、P-5以及对比例聚合物dp-1和dp-2的制备
(1)聚合物P-1的制备方法:依次称量0.8g甲基丙烯酸羟乙酯、0.2g甲基丙烯酸-2-乙氧基乙基酯、0.035g乙二醇二甲基丙烯酸酯、0.015g2-(2'-羟基-3'-甲代烯丙基-5'-甲基苯基)苯并三唑、0.0001g式(1)偶氮化合物和0.005g偶氮二异丁腈,并混合均匀,然后将混和液加入长20mm、宽10mm和厚0.4mm的空腔玻璃模具中,再将充满混合液体的模具放入鼓风烘箱中在100摄氏度下保温48小时,后取出得到聚合后的薄片材料,厚度为0.4mm、长度为20mm,宽为10mm。
(2)聚合物P-2、P-3、P-4和P-5制备方法与P-1相同,各组分用量如下表2所示。
(3)对比例聚合物dp-1为不含偶氮化合物的聚合物,对比例聚合物dp-2为使用不可聚合的偶氮化合物的聚合物,对比例聚合物dp-3为使用其它已公开可聚合偶氮化合物制备的聚合物,dp-1、dp-2和dp-3的制备方法与P-1制备方法相同,组成成分如下表2所示。
表2:
原料简写说明
HEMA:甲基丙烯酸羟乙酯
EOEMA:甲基丙烯酸-2-乙氧基乙基酯
MMA:甲基丙烯酸甲酯
PEA:2-苯基乙基丙烯酸酯
PEMA:2-苯基乙基甲基丙烯酸酯
BDDA:1,4-丁二醇二丙烯酸酯
EGDMA:乙二醇二甲基丙烯酸酯
TMPTA:三羟甲基丙烷三甲基丙烯酸酯
UA:2-(2'-羟基-3'-甲代烯丙基-5'-甲基苯基)苯并三唑
Y-1:偶氮苯,CAS号103-33-3
Y-2:结构式为:
AIBN:偶氮二异丁腈
实施例3聚合物光谱透过率测定
(1)测试方法:室温下在空气中使用安捷伦Cary60紫外可见分光光度计分别测试聚合物薄片P-1、P-2、P-3、P-4、P-5、dp-1和dp-2在200-800nm范围内的光谱透过率;然后将上述薄片材料使用无水乙醇索氏回流清洗24小时,之后在60摄氏度下真空干燥24小时,再测试清洗干燥后的聚合物薄片在200-800nm范围内的光谱透过率。分别对比上述薄片清洗前后在蓝光450nm和480nm处的光谱透过率变化,以及材料清洗前后的最大光谱透过率值。上述材料在波长450nm和480nm处光谱透过率越低则说明材料对蓝光吸收越多。
(2)结果:P-1、P-2、P-3、P-4和P-5在清洗前后的光谱透过率保持一直,均吸收蓝光,在蓝光处变现出较低的透过率。对比例聚合物dp-1清洗前后均无蓝光吸收,蓝光光谱部分全部透过;对比例聚合物dp-2清洗前后蓝光部分吸收明显小于清洗前,即清洗后dp-2在蓝光光谱部分透过率增大;对比例dp-3清洗前后光谱透过率保持不变,但蓝光吸收能力弱于P-1、P-2、P-3、P-4和P-5,即在450nm和480nm光谱处dp-3对蓝光的透过率更大,结果如下表3所示。
表3:
实施例3偶氮化合物生物相容性测试
(1)测试方法:细胞毒性按照标准GB/T 16886.5-2017附录C中MTT细胞毒性试验方法检测偶氮化合物的细胞毒性。
(2)结果如下表4所示,细胞毒性结果分级按照标准GB/T 16886.5-2017中8.5的判定方法,0级为无细胞毒性,1级为轻微毒性,2级为轻度毒性,3级为中度毒性,4级为重度毒性。医用材料细胞毒性要求不低于3级。结果显示本发明所述偶氮化合物具有较低的细胞毒性,而且比对比例化合物具有更低的细胞毒性。
表4:
偶氮化合物 | 细胞毒性分级 | 偶氮化合物 | 细胞毒性 | 偶氮化合物 | 细胞毒性 |
式(1) | 2级 | 式(15) | 0级 | 式(23) | 0级 |
式(3) | 2级 | 式(17) | 0级 | 式(25) | 0级 |
式(5) | 2级 | 式(18) | 0级 | 式(26) | 0级 |
式(7) | 2级 | 式(19) | 0级 | 对比化合物D-1 | 3级 |
式(9) | 2级 | 式(20) | 0级 | 对比化合物D-2 | 3级 |
式(11) | 1级 | 式(21) | 0级 | 对比化合物D-3 | 3级 |
式(13) | 1级 | 式(22) | 0级 | 对比化合物D-4 | 3级 |
对于本领域技术人员显而易见的是,尽管上面已经示出和描述了本发明的实施例,可以理解的是,上述实施例是示例性的,不能理解为对本发明的限制,本领域的普通技术人员在不脱离本发明的原理和宗旨的情况下在本发明的范围内可以对上述实施例进行变化、修改、替换和变型,本发明的范围由权利要求及其等同物限定。
Claims (10)
2.根据权利要求1所述的偶氮化合物,其特征在于,所述R1为氢或甲基。
3.根据权利要求1所述的偶氮化合物,其特征在于,所述R2为甲基、乙基或正丙基。
4.根据权利要求1所述的偶氮化合物,其特征在于,所述n等于1、2、3或4,或聚乙二醇结构片段分子量为200至20000。
5.根据权利要求1所述的偶氮化合物,其特征在于,所述R3、R4、R5、R6、R7、R8、R9、R10和R11分别独立地为氢、氟、氯、溴、碘、-OH、-NH2、甲基、乙基、正丙基、异丙基、正丁基、异丁基、叔丁基、甲氧基、乙氧基、正丙氧基、异丙氧基、正丁氧基、异丁氧基、正己氧基、甲氧基甲基、甲氧基乙基、乙氧基甲基、乙氧基乙基、乙氧基丙基、苯基和苯氧基。
7.一种蓝光过滤聚合物,其特征在于,构成所述聚合物的单体包括本体单体和蓝光吸收剂,所述蓝光吸收剂为上述权利要求1-6所述的任选地偶氮化合物。
8.根据权利要求7所述聚合物,其特征在于,所述本体单体为甲基丙烯酸酯单体、丙烯酸酯类单体和乙烯基类单体的至少之一。
9.根据权利7-8所述聚合物,其特征在于,构成聚合物的原料还任选地包括交联剂、紫外吸收剂和引发剂。
10.根据权利要求1~9任一项所述的偶氮化合物及其聚合物在人工晶状体、隐形眼镜、角膜塑型触镜、人工虹膜、其它眼部器械材料、化妆品材料、光电材料、医用材料、涂料、油墨和橡胶材料中的用途。
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN202010823974.5A CN114075122B (zh) | 2020-08-17 | 2020-08-17 | 一种亲水性偶氮化合物及其用途 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN202010823974.5A CN114075122B (zh) | 2020-08-17 | 2020-08-17 | 一种亲水性偶氮化合物及其用途 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN114075122A true CN114075122A (zh) | 2022-02-22 |
CN114075122B CN114075122B (zh) | 2024-01-02 |
Family
ID=80281002
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN202010823974.5A Active CN114075122B (zh) | 2020-08-17 | 2020-08-17 | 一种亲水性偶氮化合物及其用途 |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN114075122B (zh) |
Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1371481A (zh) * | 1999-09-02 | 2002-09-25 | 爱尔康公司 | 用作外科植入物的共价键合的亲水性涂层组合物 |
US20060197067A1 (en) * | 2005-03-04 | 2006-09-07 | Erning Xia | Radiation-absorbing materials, ophthalmic compositions containing same, and method of treating ophthalmic devices |
WO2018036543A1 (zh) * | 2016-08-25 | 2018-03-01 | 广东东阳光药业有限公司 | 偶氮化合物、聚合物和制备方法及用途 |
WO2018095369A1 (zh) * | 2016-11-24 | 2018-05-31 | 广东东阳光药业有限公司 | 单体、聚合物、制备方法及其用途 |
WO2018099416A1 (zh) * | 2016-11-30 | 2018-06-07 | 东莞东阳光科研发有限公司 | 偶氮化合物、聚合物和它们的制备方法及用途 |
WO2018177329A1 (zh) * | 2017-03-29 | 2018-10-04 | 东莞东阳光科研发有限公司 | 可聚合染料化合物、制备方法、含该染料的聚合物及用途 |
-
2020
- 2020-08-17 CN CN202010823974.5A patent/CN114075122B/zh active Active
Patent Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1371481A (zh) * | 1999-09-02 | 2002-09-25 | 爱尔康公司 | 用作外科植入物的共价键合的亲水性涂层组合物 |
US20060197067A1 (en) * | 2005-03-04 | 2006-09-07 | Erning Xia | Radiation-absorbing materials, ophthalmic compositions containing same, and method of treating ophthalmic devices |
WO2018036543A1 (zh) * | 2016-08-25 | 2018-03-01 | 广东东阳光药业有限公司 | 偶氮化合物、聚合物和制备方法及用途 |
WO2018095369A1 (zh) * | 2016-11-24 | 2018-05-31 | 广东东阳光药业有限公司 | 单体、聚合物、制备方法及其用途 |
WO2018099416A1 (zh) * | 2016-11-30 | 2018-06-07 | 东莞东阳光科研发有限公司 | 偶氮化合物、聚合物和它们的制备方法及用途 |
WO2018177329A1 (zh) * | 2017-03-29 | 2018-10-04 | 东莞东阳光科研发有限公司 | 可聚合染料化合物、制备方法、含该染料的聚合物及用途 |
Non-Patent Citations (1)
Title |
---|
魏雨等: "基于聚乙二醇生物相容性涂层的构建及其释药行为研究", 化工新型材料 * |
Also Published As
Publication number | Publication date |
---|---|
CN114075122B (zh) | 2024-01-02 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
WO2007050394A2 (en) | Polymeric radiation-absorbing materials and ophthalmic devices comprising same | |
US20070092831A1 (en) | Radiation-absorbing polymeric materials and ophthalmic devices comprising same | |
EP1828270B1 (en) | Nanohybrid polymers for ophthalmic applications | |
JP6152538B2 (ja) | 光学ポリマーのための光吸収化合物 | |
JP5758407B2 (ja) | 眼科用レンズの材料のための可視光吸収剤 | |
EP1096905B1 (en) | Uv blocking lenses and material containing benzotriazoles and benzophenones | |
KR101869746B1 (ko) | 자외선 흡수제들 및 청색광 발색단들의 조합을 이용한 인공수정체들 | |
US8329842B2 (en) | Ophthalmological composition and use thereof | |
CA2945961C (en) | (meth)acrylamide polymers for contact lens and intraocular lens | |
US20060252850A1 (en) | Radiation-absorbing polymeric materials and ophthalmic devices comprising same | |
JP2011507987A (ja) | 共重合体及び眼科用組成物 | |
WO2011074501A1 (ja) | アントラキノン系色素、これを用いた眼用レンズ材料、眼用レンズ材料の製造方法及び眼用レンズ | |
US8585938B1 (en) | UV-absorbers for ophthalmic lens materials | |
JP2012532196A (ja) | 眼科用レンズ材料のための紫外線/可視光吸収剤 | |
CN105384867B (zh) | 一种制备疏水性人工晶体的聚合物 | |
CN114075122B (zh) | 一种亲水性偶氮化合物及其用途 | |
CN116836145B (zh) | 一种可聚合的光致变色化合物及其应用 | |
CN113527567B (zh) | 疏水性无闪光点高折光率眼科聚合物材料 | |
KR102499628B1 (ko) | 청색광 차단 기능을 갖는 콘택트렌즈와 이의 제조방법 | |
JPH0651101A (ja) | 光学レンズ用樹脂 | |
JPH067424A (ja) | 眼内レンズ材料 | |
WO2023076961A1 (en) | Polymers and methods for ophthalmic applications |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PB01 | Publication | ||
PB01 | Publication | ||
SE01 | Entry into force of request for substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
GR01 | Patent grant | ||
GR01 | Patent grant |