ZA200508177B - Indeno-fused photochromic naphthopyrans, naphthols and photochromic articles - Google Patents
Indeno-fused photochromic naphthopyrans, naphthols and photochromic articles Download PDFInfo
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- ZA200508177B ZA200508177B ZA200508177A ZA200508177A ZA200508177B ZA 200508177 B ZA200508177 B ZA 200508177B ZA 200508177 A ZA200508177 A ZA 200508177A ZA 200508177 A ZA200508177 A ZA 200508177A ZA 200508177 B ZA200508177 B ZA 200508177B
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- South Africa
- Prior art keywords
- alkyl
- chosen
- mono
- phenyl
- alkoxy
- Prior art date
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- 150000004780 naphthols Chemical class 0.000 title description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 380
- -1 benzothien~2-yl Chemical group 0.000 claims description 223
- 125000003545 alkoxy group Chemical group 0.000 claims description 198
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 179
- 229910052739 hydrogen Inorganic materials 0.000 claims description 133
- 239000001257 hydrogen Substances 0.000 claims description 133
- 239000000463 material Substances 0.000 claims description 103
- 125000003118 aryl group Chemical group 0.000 claims description 88
- 150000002431 hydrogen Chemical class 0.000 claims description 80
- 125000001624 naphthyl group Chemical group 0.000 claims description 74
- 125000001424 substituent group Chemical group 0.000 claims description 69
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 64
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 53
- 150000001875 compounds Chemical class 0.000 claims description 50
- 125000001153 fluoro group Chemical group F* 0.000 claims description 49
- 125000003282 alkyl amino group Chemical group 0.000 claims description 44
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 44
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 28
- VCMLCMCXCRBSQO-UHFFFAOYSA-N 3h-benzo[f]chromene Chemical compound C1=CC=CC2=C(C=CCO3)C3=CC=C21 VCMLCMCXCRBSQO-UHFFFAOYSA-N 0.000 claims description 27
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 25
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 24
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 24
- 238000000576 coating method Methods 0.000 claims description 23
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 22
- 239000011248 coating agent Substances 0.000 claims description 22
- 229910052760 oxygen Inorganic materials 0.000 claims description 22
- 239000001301 oxygen Substances 0.000 claims description 22
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 22
- 150000001412 amines Chemical class 0.000 claims description 21
- 229920000642 polymer Polymers 0.000 claims description 21
- 125000001544 thienyl group Chemical group 0.000 claims description 21
- 125000004104 aryloxy group Chemical group 0.000 claims description 20
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 19
- 239000000203 mixture Substances 0.000 claims description 19
- 239000000178 monomer Substances 0.000 claims description 19
- 229910052757 nitrogen Inorganic materials 0.000 claims description 19
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 18
- 125000004965 chloroalkyl group Chemical group 0.000 claims description 18
- 229920006395 saturated elastomer Polymers 0.000 claims description 18
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 17
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 claims description 17
- 150000002430 hydrocarbons Chemical group 0.000 claims description 17
- 125000006413 ring segment Chemical group 0.000 claims description 17
- 125000004171 alkoxy aryl group Chemical group 0.000 claims description 16
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 16
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 15
- 125000004244 benzofuran-2-yl group Chemical group [H]C1=C(*)OC2=C([H])C([H])=C([H])C([H])=C12 0.000 claims description 14
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 14
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 14
- 150000002829 nitrogen Chemical class 0.000 claims description 14
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 13
- 125000004532 benzofuran-3-yl group Chemical group O1C=C(C2=C1C=CC=C2)* 0.000 claims description 12
- 239000000758 substrate Substances 0.000 claims description 12
- 238000005299 abrasion Methods 0.000 claims description 11
- 125000002252 acyl group Chemical group 0.000 claims description 11
- 125000004197 benzothien-3-yl group Chemical group [H]C1=C(*)C2=C([H])C([H])=C([H])C([H])=C2S1 0.000 claims description 11
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 11
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 10
- FRIJWEQBTIZQMD-UHFFFAOYSA-N Benzo[c]fluorene Chemical compound C1=CC2=CC=CC=C2C2=C1CC1=CC=CC=C12 FRIJWEQBTIZQMD-UHFFFAOYSA-N 0.000 claims description 10
- 150000001602 bicycloalkyls Chemical group 0.000 claims description 10
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 10
- 125000002541 furyl group Chemical group 0.000 claims description 10
- 125000004534 benzothien-2-yl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 9
- 229910052736 halogen Inorganic materials 0.000 claims description 9
- 125000001246 bromo group Chemical group Br* 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 125000001072 heteroaryl group Chemical group 0.000 claims description 8
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 7
- 125000005370 alkoxysilyl group Chemical group 0.000 claims description 7
- 125000005103 alkyl silyl group Chemical group 0.000 claims description 7
- 150000002367 halogens Chemical class 0.000 claims description 7
- 230000003287 optical effect Effects 0.000 claims description 7
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 125000004986 diarylamino group Chemical group 0.000 claims description 6
- 125000001038 naphthoyl group Chemical group C1(=CC=CC2=CC=CC=C12)C(=O)* 0.000 claims description 6
- 125000004043 oxo group Chemical group O=* 0.000 claims description 6
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 claims description 6
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 claims description 6
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 claims description 6
- 230000035945 sensitivity Effects 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 239000011593 sulfur Substances 0.000 claims description 6
- 238000010521 absorption reaction Methods 0.000 claims description 5
- 125000001118 alkylidene group Chemical group 0.000 claims description 5
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 5
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 5
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 5
- 125000001041 indolyl group Chemical group 0.000 claims description 5
- 125000005956 isoquinolyl group Chemical group 0.000 claims description 5
- 229910052751 metal Inorganic materials 0.000 claims description 5
- 239000002184 metal Substances 0.000 claims description 5
- 125000005561 phenanthryl group Chemical group 0.000 claims description 5
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 5
- 125000001725 pyrenyl group Chemical group 0.000 claims description 5
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 5
- 229920002554 vinyl polymer Polymers 0.000 claims description 5
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 claims description 4
- 150000001721 carbon Chemical group 0.000 claims description 4
- 125000004407 fluoroaryl group Chemical group 0.000 claims description 4
- 125000002636 imidazolinyl group Chemical group 0.000 claims description 4
- 125000002883 imidazolyl group Chemical group 0.000 claims description 4
- UEOGLANRPZAEAC-UHFFFAOYSA-N indeno-naphthopyran Chemical compound O1C=CC=C2C3=C4C=C(C=CC=C5)C5=C4C=CC3=CC=C21 UEOGLANRPZAEAC-UHFFFAOYSA-N 0.000 claims description 4
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims description 4
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
- 238000011056 performance test Methods 0.000 claims description 4
- 125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 claims description 4
- 125000002755 pyrazolinyl group Chemical group 0.000 claims description 4
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 4
- 125000001422 pyrrolinyl group Chemical group 0.000 claims description 4
- 239000006117 anti-reflective coating Substances 0.000 claims description 3
- 150000008371 chromenes Chemical class 0.000 claims description 3
- 125000004367 cycloalkylaryl group Chemical group 0.000 claims description 3
- 125000001188 haloalkyl group Chemical group 0.000 claims description 3
- 150000004893 oxazines Chemical class 0.000 claims description 3
- 125000004076 pyridyl group Chemical group 0.000 claims description 3
- 125000003107 substituted aryl group Chemical group 0.000 claims description 3
- DLJVUTFKAYMOEJ-UHFFFAOYSA-N 3,4-dimethoxy-7,7-dimethyl-9-morpholin-4-ylbenzo[c]fluoren-5-ol Chemical compound C1=C2C(C)(C)C=3C=C(O)C4=C(OC)C(OC)=CC=C4C=3C2=CC=C1N1CCOCC1 DLJVUTFKAYMOEJ-UHFFFAOYSA-N 0.000 claims description 2
- UMIZKYJCPNWCHW-UHFFFAOYSA-N 3-methoxy-4-methyl-9-morpholin-4-yl-7-phenylbenzo[c]fluorene-5,7-diol Chemical compound C1=2C=C(O)C3=C(C)C(OC)=CC=C3C=2C2=CC=C(N3CCOCC3)C=C2C1(O)C1=CC=CC=C1 UMIZKYJCPNWCHW-UHFFFAOYSA-N 0.000 claims description 2
- XCNQTONOKLXXAF-UHFFFAOYSA-N 7,7-dimethyl-9-morpholin-4-ylbenzo[c]fluoren-5-ol Chemical compound C=1C=C2C(C3=CC=CC=C3C(O)=C3)=C3C(C)(C)C2=CC=1N1CCOCC1 XCNQTONOKLXXAF-UHFFFAOYSA-N 0.000 claims description 2
- OHHLHSVEZFJHIV-UHFFFAOYSA-N 9-fluoro-7,7-dimethylbenzo[c]fluoren-5-ol Chemical compound C1=C(O)C2=CC=CC=C2C2=C1C(C)(C)C1=CC(F)=CC=C12 OHHLHSVEZFJHIV-UHFFFAOYSA-N 0.000 claims description 2
- 125000003865 brosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Br)S(*)(=O)=O 0.000 claims description 2
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 2
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 13
- 229920001187 thermosetting polymer Polymers 0.000 claims 13
- 229920001169 thermoplastic Polymers 0.000 claims 10
- 239000004416 thermosoftening plastic Substances 0.000 claims 10
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 claims 5
- MGADZUXDNSDTHW-UHFFFAOYSA-N 2H-pyran Chemical compound C1OC=CC=C1 MGADZUXDNSDTHW-UHFFFAOYSA-N 0.000 claims 5
- 239000008199 coating composition Substances 0.000 claims 4
- 239000011368 organic material Substances 0.000 claims 4
- 229920002635 polyurethane Polymers 0.000 claims 4
- 239000004814 polyurethane Substances 0.000 claims 4
- 125000005493 quinolyl group Chemical group 0.000 claims 4
- 239000012815 thermoplastic material Substances 0.000 claims 4
- 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 claims 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 2
- 229920002732 Polyanhydride Polymers 0.000 claims 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims 2
- 229920003180 amino resin Polymers 0.000 claims 2
- 239000000919 ceramic Substances 0.000 claims 2
- 229920001577 copolymer Chemical compound 0.000 claims 2
- 239000003822 epoxy resin Substances 0.000 claims 2
- 239000011521 glass Substances 0.000 claims 2
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 claims 2
- 239000000123 paper Substances 0.000 claims 2
- 229920000548 poly(silane) polymer Polymers 0.000 claims 2
- 229920002401 polyacrylamide Polymers 0.000 claims 2
- 229920000515 polycarbonate Polymers 0.000 claims 2
- 239000004417 polycarbonate Substances 0.000 claims 2
- 229920000647 polyepoxide Polymers 0.000 claims 2
- 229920005989 resin Polymers 0.000 claims 2
- 239000011347 resin Substances 0.000 claims 2
- 239000007787 solid Substances 0.000 claims 2
- 239000004753 textile Substances 0.000 claims 2
- 239000002023 wood Substances 0.000 claims 2
- HIACAHMKXQESOV-UHFFFAOYSA-N 1,2-bis(prop-1-en-2-yl)benzene Chemical compound CC(=C)C1=CC=CC=C1C(C)=C HIACAHMKXQESOV-UHFFFAOYSA-N 0.000 claims 1
- SKESERDUDQOXKM-UHFFFAOYSA-N 2-methylprop-2-enoic acid;phenol Chemical class CC(=C)C(O)=O.CC(=C)C(O)=O.OC1=CC=CC=C1 SKESERDUDQOXKM-UHFFFAOYSA-N 0.000 claims 1
- OOXMQACSWCZQLX-UHFFFAOYSA-N 3,9-bis(ethenyl)-2,4,8,10-tetraoxaspiro[5.5]undecane Chemical compound C1OC(C=C)OCC21COC(C=C)OC2 OOXMQACSWCZQLX-UHFFFAOYSA-N 0.000 claims 1
- WOLHQSJQOGFFTI-UHFFFAOYSA-N 3-methoxy-4,7,7-trimethyl-9-morpholin-4-ylbenzo[c]fluoren-5-ol Chemical compound C1=C2C(C)(C)C=3C=C(O)C4=C(C)C(OC)=CC=C4C=3C2=CC=C1N1CCOCC1 WOLHQSJQOGFFTI-UHFFFAOYSA-N 0.000 claims 1
- MHRURIFLERCMBX-UHFFFAOYSA-N 4-(1-thiomorpholin-4-yl-3,4-dihydro-2H-quinolin-2-yl)morpholine Chemical compound O1CCN(CC1)C1N(C2=CC=CC=C2CC1)N1CCSCC1 MHRURIFLERCMBX-UHFFFAOYSA-N 0.000 claims 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 1
- MBGJMPVJFJFLFX-UHFFFAOYSA-N 7,7-dimethyl-9-piperidin-1-ylbenzo[c]fluoren-5-ol Chemical compound C=1C=C2C(C3=CC=CC=C3C(O)=C3)=C3C(C)(C)C2=CC=1N1CCCCC1 MBGJMPVJFJFLFX-UHFFFAOYSA-N 0.000 claims 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims 1
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- 229920002284 Cellulose triacetate Polymers 0.000 claims 1
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- NNLVGZFZQQXQNW-ADJNRHBOSA-N [(2r,3r,4s,5r,6s)-4,5-diacetyloxy-3-[(2s,3r,4s,5r,6r)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6s)-4,5,6-triacetyloxy-2-(acetyloxymethyl)oxan-3-yl]oxyoxan-2-yl]methyl acetate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](OC(C)=O)[C@H]1OC(C)=O)O[C@H]1[C@@H]([C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](COC(C)=O)O1)OC(C)=O)COC(=O)C)[C@@H]1[C@@H](COC(C)=O)O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O NNLVGZFZQQXQNW-ADJNRHBOSA-N 0.000 claims 1
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- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- UHESRSKEBRADOO-UHFFFAOYSA-N ethyl carbamate;prop-2-enoic acid Chemical compound OC(=O)C=C.CCOC(N)=O UHESRSKEBRADOO-UHFFFAOYSA-N 0.000 claims 1
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- QIWKUEJZZCOPFV-UHFFFAOYSA-N phenyl 2-methylprop-2-enoate Chemical class CC(=C)C(=O)OC1=CC=CC=C1 QIWKUEJZZCOPFV-UHFFFAOYSA-N 0.000 claims 1
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- 238000006243 chemical reaction Methods 0.000 description 35
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- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- FAQVDANXTSFXGA-UHFFFAOYSA-N 2,3-dihydro-1h-benzo[g]indole Chemical compound C1=CC=CC2=C(NCC3)C3=CC=C21 FAQVDANXTSFXGA-UHFFFAOYSA-N 0.000 description 3
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 3
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 239000012965 benzophenone Substances 0.000 description 3
- 150000008366 benzophenones Chemical class 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- 229960001701 chloroform Drugs 0.000 description 3
- 238000005859 coupling reaction Methods 0.000 description 3
- 150000004795 grignard reagents Chemical class 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 229910052744 lithium Inorganic materials 0.000 description 3
- 229910003002 lithium salt Inorganic materials 0.000 description 3
- 159000000002 lithium salts Chemical class 0.000 description 3
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 3
- 229910052753 mercury Inorganic materials 0.000 description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 230000005855 radiation Effects 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 238000002834 transmittance Methods 0.000 description 3
- SJJCQDRGABAVBB-UHFFFAOYSA-N 1-hydroxy-2-naphthoic acid Chemical compound C1=CC=CC2=C(O)C(C(=O)O)=CC=C21 SJJCQDRGABAVBB-UHFFFAOYSA-N 0.000 description 2
- KYNSBQPICQTCGU-UHFFFAOYSA-N Benzopyrane Chemical compound C1=CC=C2C=CCOC2=C1 KYNSBQPICQTCGU-UHFFFAOYSA-N 0.000 description 2
- MUXOBHXGJLMRAB-UHFFFAOYSA-N Dimethyl succinate Chemical compound COC(=O)CCC(=O)OC MUXOBHXGJLMRAB-UHFFFAOYSA-N 0.000 description 2
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 2
- 239000007818 Grignard reagent Substances 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- 238000006600 Stobbe condensation reaction Methods 0.000 description 2
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 150000001562 benzopyrans Chemical class 0.000 description 2
- 238000006210 cyclodehydration reaction Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- VGKONPUVOVVNSU-UHFFFAOYSA-N naphthalen-1-yl acetate Chemical class C1=CC=C2C(OC(=O)C)=CC=CC2=C1 VGKONPUVOVVNSU-UHFFFAOYSA-N 0.000 description 2
- 150000004880 oxines Chemical class 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000002952 polymeric resin Substances 0.000 description 2
- 229920001451 polypropylene glycol Polymers 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 2
- 239000011253 protective coating Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 230000002441 reversible effect Effects 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- 239000001384 succinic acid Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 229920003002 synthetic resin Polymers 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- YBHMXCZRJHSLKK-UHFFFAOYSA-N 10-methoxy-7,7-dimethyl-9-morpholin-4-ylbenzo[c]fluoren-5-ol Chemical compound COC1=CC(C2=C3C=CC=CC3=C(O)C=C2C2(C)C)=C2C=C1N1CCOCC1 YBHMXCZRJHSLKK-UHFFFAOYSA-N 0.000 description 1
- GFSXWQUSLTVUBW-UHFFFAOYSA-N 10bh-benzo[h]chromene Chemical compound C1=CC=C2C3OC=CC=C3C=CC2=C1 GFSXWQUSLTVUBW-UHFFFAOYSA-N 0.000 description 1
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 description 1
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 1
- QEQVCPKISCKMOQ-UHFFFAOYSA-N 3h-benzo[f][1,2]benzoxazine Chemical class C1=CC=CC2=C(C=CNO3)C3=CC=C21 QEQVCPKISCKMOQ-UHFFFAOYSA-N 0.000 description 1
- BKHIDUNUWRNKCF-UHFFFAOYSA-N 7,7-dimethyl-9-phenylsulfanylbenzo[c]fluoren-5-ol Chemical compound C=1C=C2C(C3=CC=CC=C3C(O)=C3)=C3C(C)(C)C2=CC=1SC1=CC=CC=C1 BKHIDUNUWRNKCF-UHFFFAOYSA-N 0.000 description 1
- 101100273639 Carassius auratus ccna1 gene Proteins 0.000 description 1
- BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- QPFYXYFORQJZEC-FOCLMDBBSA-N Phenazopyridine Chemical compound NC1=NC(N)=CC=C1\N=N\C1=CC=CC=C1 QPFYXYFORQJZEC-FOCLMDBBSA-N 0.000 description 1
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 description 1
- 150000001266 acyl halides Chemical class 0.000 description 1
- DCBMHXCACVDWJZ-UHFFFAOYSA-N adamantylidene Chemical group C1C(C2)CC3[C]C1CC2C3 DCBMHXCACVDWJZ-UHFFFAOYSA-N 0.000 description 1
- 230000002152 alkylating effect Effects 0.000 description 1
- 230000003667 anti-reflective effect Effects 0.000 description 1
- 238000005808 aromatic amination reaction Methods 0.000 description 1
- 150000008378 aryl ethers Chemical class 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 125000005605 benzo group Chemical class 0.000 description 1
- 150000005130 benzoxazines Chemical class 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical class ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- OOSCHYDNHHSIKU-UHFFFAOYSA-N bicyclo[4.3.2]undecane Chemical compound C1CC2CCCC1CCCC2 OOSCHYDNHHSIKU-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000004556 carbazol-9-yl group Chemical group C1=CC=CC=2C3=CC=CC=C3N(C12)* 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000000295 complement effect Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000005538 encapsulation Methods 0.000 description 1
- YLQWCDOCJODRMT-UHFFFAOYSA-N fluoren-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C2=C1 YLQWCDOCJODRMT-UHFFFAOYSA-N 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000003574 free electron Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 125000001475 halogen functional group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002390 heteroarenes Chemical class 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- AFRJJFRNGGLMDW-UHFFFAOYSA-N lithium amide Chemical class [Li+].[NH2-] AFRJJFRNGGLMDW-UHFFFAOYSA-N 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- SFDZETWZUCDYMD-UHFFFAOYSA-N monosodium acetylide Chemical compound [Na+].[C-]#C SFDZETWZUCDYMD-UHFFFAOYSA-N 0.000 description 1
- 238000007339 nucleophilic aromatic substitution reaction Methods 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 125000001979 organolithium group Chemical group 0.000 description 1
- 238000005691 oxidative coupling reaction Methods 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- PNNRZXFUPQQZSO-UHFFFAOYSA-N pyran Chemical compound [CH]1OC=CC=C1 PNNRZXFUPQQZSO-UHFFFAOYSA-N 0.000 description 1
- 229940070891 pyridium Drugs 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000012260 resinous material Substances 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 238000007655 standard test method Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/78—Ring systems having three or more relevant rings
- C07D311/92—Naphthopyrans; Hydrogenated naphthopyrans
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/15—Heterocyclic compounds having oxygen in the ring
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K9/00—Tenebrescent materials, i.e. materials for which the range of wavelengths for energy absorption is changed as a result of excitation by some form of energy
- C09K9/02—Organic tenebrescent materials
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31551—Of polyamidoester [polyurethane, polyisocyanate, polycarbamate, etc.]
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T442/00—Fabric [woven, knitted, or nonwoven textile or cloth, etc.]
- Y10T442/20—Coated or impregnated woven, knit, or nonwoven fabric which is not [a] associated with another preformed layer or fiber layer or, [b] with respect to woven and knit, characterized, respectively, by a particular or differential weave or knit, wherein the coating or impregnation is neither a foamed material nor a free metal or alloy layer
- Y10T442/259—Coating or impregnation provides protection from radiation [e.g., U.V., visible light, I.R., micscheme-change-itemave, high energy particle, etc.] or heat retention thru radiation absorption
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Materials Engineering (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Pyrane Compounds (AREA)
- Materials For Medical Uses (AREA)
- Eyeglasses (AREA)
- Optical Filters (AREA)
- Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US10/393,177 US7262295B2 (en) | 2003-03-20 | 2003-03-20 | Indeno-fused photochromic naphthopyrans, naphthols and photochromic articles |
Publications (1)
Publication Number | Publication Date |
---|---|
ZA200508177B true ZA200508177B (en) | 2007-01-31 |
Family
ID=32988076
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
ZA200508177A ZA200508177B (en) | 2003-03-20 | 2005-10-10 | Indeno-fused photochromic naphthopyrans, naphthols and photochromic articles |
Country Status (13)
Country | Link |
---|---|
US (3) | US7262295B2 (pt) |
EP (3) | EP2345647A3 (pt) |
JP (1) | JP4160980B2 (pt) |
KR (1) | KR100752834B1 (pt) |
CN (2) | CN102532088B (pt) |
AU (1) | AU2004311372B8 (pt) |
BR (1) | BRPI0408540B1 (pt) |
CA (1) | CA2512605C (pt) |
ES (2) | ES2688272T3 (pt) |
HK (1) | HK1089161A1 (pt) |
MX (1) | MXPA05009631A (pt) |
WO (1) | WO2005090327A1 (pt) |
ZA (1) | ZA200508177B (pt) |
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US20050258408A1 (en) * | 2001-12-20 | 2005-11-24 | Molock Frank F | Photochromic contact lenses and methods for their production |
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US20060227287A1 (en) * | 2005-04-08 | 2006-10-12 | Frank Molock | Photochromic ophthalmic devices made with dual initiator system |
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US8147725B2 (en) | 2005-04-08 | 2012-04-03 | Transitions Optical, Inc | Photochromic materials having extended pi-conjugated systems and compositions and articles including the same |
US9028728B2 (en) | 2005-04-08 | 2015-05-12 | Transitions Optical, Inc. | Photochromic materials that include indeno-fused naphthopyrans |
US20060226402A1 (en) * | 2005-04-08 | 2006-10-12 | Beon-Kyu Kim | Ophthalmic devices comprising photochromic materials having extended PI-conjugated systems |
US7556750B2 (en) * | 2005-04-08 | 2009-07-07 | Transitions Optical, Inc. | Photochromic materials with reactive substituents |
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US8158037B2 (en) | 2005-04-08 | 2012-04-17 | Johnson & Johnson Vision Care, Inc. | Photochromic materials having extended pi-conjugated systems and compositions and articles including the same |
US20060228557A1 (en) * | 2005-04-08 | 2006-10-12 | Beon-Kyu Kim | Photochromic materials having extended pi-conjugated systems and compositions and articles including the same |
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KR20090082258A (ko) * | 2006-10-26 | 2009-07-29 | 시바 홀딩 인크 | 광변색성 시스템을 위한 광 흡수층 |
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