EP2337810A1 - Polydialkylsiloxanverbrückte biphotochrome moleküle - Google Patents
Polydialkylsiloxanverbrückte biphotochrome moleküleInfo
- Publication number
- EP2337810A1 EP2337810A1 EP09784948A EP09784948A EP2337810A1 EP 2337810 A1 EP2337810 A1 EP 2337810A1 EP 09784948 A EP09784948 A EP 09784948A EP 09784948 A EP09784948 A EP 09784948A EP 2337810 A1 EP2337810 A1 EP 2337810A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- dms
- photochromic
- molecule according
- photochromic molecule
- alkyl
- 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.)
- Withdrawn
Links
- 229920006294 polydialkylsiloxane Polymers 0.000 claims abstract description 33
- 239000000463 material Substances 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 29
- 125000000217 alkyl group Chemical group 0.000 claims description 23
- 125000005647 linker group Chemical group 0.000 claims description 19
- -1 polydimethylsiloxane Polymers 0.000 claims description 17
- 239000004205 dimethyl polysiloxane Substances 0.000 claims description 9
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 claims description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 125000004122 cyclic group Chemical group 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- MGADZUXDNSDTHW-UHFFFAOYSA-N 2H-pyran Chemical compound C1OC=CC=C1 MGADZUXDNSDTHW-UHFFFAOYSA-N 0.000 claims description 5
- BCHZICNRHXRCHY-UHFFFAOYSA-N 2h-oxazine Chemical compound N1OC=CC=C1 BCHZICNRHXRCHY-UHFFFAOYSA-N 0.000 claims description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
- 150000001602 bicycloalkyls Chemical group 0.000 claims description 5
- 239000001301 oxygen Substances 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 4
- 125000005036 alkoxyphenyl group Chemical group 0.000 claims description 4
- 125000003282 alkyl amino group Chemical group 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 125000001188 haloalkyl group Chemical group 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- QFDWOYKAKOTQGY-UHFFFAOYSA-N [2,2-bis(4-methoxyphenyl)-6-methylbenzo[h]chromen-5-yl]methanol Chemical compound C1=CC(OC)=CC=C1C1(C=2C=CC(OC)=CC=2)C=CC(C(CO)=C(C)C=2C3=CC=CC=2)=C3O1 QFDWOYKAKOTQGY-UHFFFAOYSA-N 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 239000005864 Sulphur Substances 0.000 claims description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000005037 alkyl phenyl group Chemical group 0.000 claims description 2
- JYNZIOFUHBJABQ-UHFFFAOYSA-N allyl-{6-[3-(4-bromo-phenyl)-benzofuran-6-yloxy]-hexyl-}-methyl-amin Chemical compound C=1OC2=CC(OCCCCCCN(C)CC=C)=CC=C2C=1C1=CC=C(Br)C=C1 JYNZIOFUHBJABQ-UHFFFAOYSA-N 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 2
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000003435 aroyl group Chemical group 0.000 claims description 2
- 125000001769 aryl amino group Chemical group 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 2
- 125000004986 diarylamino group Chemical group 0.000 claims description 2
- 125000004982 dihaloalkyl group Chemical group 0.000 claims description 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 2
- 125000001072 heteroaryl group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000005113 hydroxyalkoxy group Chemical group 0.000 claims description 2
- 125000003003 spiro group Chemical group 0.000 claims description 2
- 125000004385 trihaloalkyl group Chemical group 0.000 claims description 2
- GFSXWQUSLTVUBW-UHFFFAOYSA-N 10bh-benzo[h]chromene Chemical compound C1=CC=C2C3OC=CC=C3C=CC2=C1 GFSXWQUSLTVUBW-UHFFFAOYSA-N 0.000 claims 3
- WIFWCSTVYGGLAE-UHFFFAOYSA-N 4ah-benzo[f]chromene Chemical compound C1=CC=C2C3=CC=COC3C=CC2=C1 WIFWCSTVYGGLAE-UHFFFAOYSA-N 0.000 claims 3
- 238000000034 method Methods 0.000 claims 2
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 87
- 239000000203 mixture Substances 0.000 description 30
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 25
- 239000000243 solution Substances 0.000 description 24
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 16
- 239000004417 polycarbonate Substances 0.000 description 16
- 238000004809 thin layer chromatography Methods 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- 239000007858 starting material Substances 0.000 description 10
- 235000019439 ethyl acetate Nutrition 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 8
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 8
- 229920000642 polymer Polymers 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 239000003921 oil Substances 0.000 description 6
- 235000019198 oils Nutrition 0.000 description 6
- 239000012994 photoredox catalyst Substances 0.000 description 6
- 230000009102 absorption Effects 0.000 description 5
- 238000010521 absorption reaction Methods 0.000 description 5
- 238000004587 chromatography analysis Methods 0.000 description 5
- 150000004893 oxazines Chemical class 0.000 description 5
- 239000003208 petroleum Substances 0.000 description 5
- ADFXKUOMJKEIND-UHFFFAOYSA-N 1,3-dicyclohexylurea Chemical compound C1CCCCC1NC(=O)NC1CCCCC1 ADFXKUOMJKEIND-UHFFFAOYSA-N 0.000 description 4
- 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 4
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- 238000004040 coloring Methods 0.000 description 4
- 238000003818 flash chromatography Methods 0.000 description 4
- 150000004880 oxines Chemical class 0.000 description 4
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 230000006872 improvement Effects 0.000 description 3
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 2
- 235000019502 Orange oil Nutrition 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 239000000539 dimer Substances 0.000 description 2
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 2
- 150000002148 esters Chemical group 0.000 description 2
- 239000010502 orange oil Substances 0.000 description 2
- 229920000515 polycarbonate Polymers 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 230000002441 reversible effect Effects 0.000 description 2
- 238000012552 review Methods 0.000 description 2
- 229940014800 succinic anhydride Drugs 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- MLGCXEBRWGEOQX-UHFFFAOYSA-N tetradifon Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)C1=CC(Cl)=C(Cl)C=C1Cl MLGCXEBRWGEOQX-UHFFFAOYSA-N 0.000 description 2
- 230000007704 transition Effects 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 description 1
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- BQYPERTZJDZBIR-UHFFFAOYSA-N 2,4,6,8-tetramethyl-1,3,5,7,2,4,6,8-tetraoxatetrasilocane Chemical group C[SiH]1O[SiH](C)O[SiH](C)O[SiH](C)O1 BQYPERTZJDZBIR-UHFFFAOYSA-N 0.000 description 1
- BLGIPLYGIJZEPP-UHFFFAOYSA-N 2-[4-(6-morpholin-4-yl-3-phenylbenzo[f]chromen-3-yl)phenoxy]ethanol Chemical compound C1=CC(OCCO)=CC=C1C1(C=2C=CC=CC=2)C=CC2=C3C=CC=CC3=C(N3CCOCC3)C=C2O1 BLGIPLYGIJZEPP-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- RBBDBQLRFBOGQZ-UHFFFAOYSA-N [2-methoxy-3-[(9-methoxy-2H-benzo[h]chromen-2-yl)methyl]-4-phenyl-4-(4-pyrrolidin-1-ylphenyl)cyclohexa-1,5-dien-1-yl]methanol Chemical compound N1(CCCC1)C1=CC=C(C=C1)C1(C(CC2C=CC3=C(O2)C2=CC(=CC=C2C=C3)OC)C(=C(C=C1)CO)OC)C1=CC=CC=C1 RBBDBQLRFBOGQZ-UHFFFAOYSA-N 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- QUZSUMLPWDHKCJ-UHFFFAOYSA-N bisphenol A dimethacrylate Chemical compound C1=CC(OC(=O)C(=C)C)=CC=C1C(C)(C)C1=CC=C(OC(=O)C(C)=C)C=C1 QUZSUMLPWDHKCJ-UHFFFAOYSA-N 0.000 description 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
- 239000013626 chemical specie Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000005670 electromagnetic radiation Effects 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 125000003827 glycol group Chemical group 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 238000012430 stability testing Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/38—Polysiloxanes modified by chemical after-treatment
- C08G77/382—Polysiloxanes modified by chemical after-treatment containing atoms other than carbon, hydrogen, oxygen or silicon
- C08G77/388—Polysiloxanes modified by chemical after-treatment containing atoms other than carbon, hydrogen, oxygen or silicon containing nitrogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/06—Peri-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C03—GLASS; MINERAL OR SLAG WOOL
- C03C—CHEMICAL COMPOSITION OF GLASSES, GLAZES OR VITREOUS ENAMELS; SURFACE TREATMENT OF GLASS; SURFACE TREATMENT OF FIBRES OR FILAMENTS MADE FROM GLASS, MINERALS OR SLAGS; JOINING GLASS TO GLASS OR OTHER MATERIALS
- C03C4/00—Compositions for glass with special properties
- C03C4/04—Compositions for glass with special properties for photosensitive glass
- C03C4/06—Compositions for glass with special properties for photosensitive glass for phototropic or photochromic glass
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/045—Polysiloxanes containing less than 25 silicon atoms
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/38—Polysiloxanes modified by chemical after-treatment
-
- 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
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
- G03C1/00—Photosensitive materials
- G03C1/685—Compositions containing spiro-condensed pyran compounds or derivatives thereof, as photosensitive substances
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
- G03C1/00—Photosensitive materials
- G03C1/72—Photosensitive compositions not covered by the groups G03C1/005 - G03C1/705
- G03C1/73—Photosensitive compositions not covered by the groups G03C1/005 - G03C1/705 containing organic compounds
- G03C1/733—Photosensitive compositions not covered by the groups G03C1/005 - G03C1/705 containing organic compounds with macromolecular compounds as photosensitive substances, e.g. photochromic
-
- 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
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1011—Condensed systems
-
- 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
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/14—Macromolecular compounds
- C09K2211/1441—Heterocyclic
- C09K2211/145—Heterocyclic containing oxygen as the only heteroatom
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
- G03C1/00—Photosensitive materials
- G03C1/72—Photosensitive compositions not covered by the groups G03C1/005 - G03C1/705
- G03C1/73—Photosensitive compositions not covered by the groups G03C1/005 - G03C1/705 containing organic compounds
Definitions
- the present invention relates to photochromic molecules, in particular bi-photochromic molecules comprising a polydialkylsiloxane oligomer linker, and to products comprising them.
- Photochromism is a well known physical phenomenon, which is defined as "a reversible transformation of a single chemical species being induced in one or both directions by electromagnetic radiation between two states having different distinguishable absorption spectra".
- a detailed discussion of this phenomenon can be found in "Photochromism : Molecules and Systems", revised edition, edited by H. Durr and H. Bouas-Laurent, Elsevier, 2003.
- a review of the major classes of organic photochromic molecules can be found in Organic Photochromic and Thermochromic Compounds, Volume 1 , Main Photochromic Families", edited by J. Crano and R. Guglielmetti, Plenum Press, 1999.
- a detailed review of photochromic naphthopyrans can be found in "Functional Dyes", edited by Sung-Hoon Kim, pages 85-137, Elsevier, Amsterdam, 2006.
- Polymerisable groups have been attached to oxazines (US 5821287, National Science Council Taiwan). Polymerisable polyalkoxylated pyrans have been claimed by PPG (WO 00/15629) and Transitions (WO 03/56390).
- Rodenstock (EP 0686685) have linked pyrans by means of a -CH 2 CH 2 - bridge which, it is taught, does not affect the photochromic properties of the photochromic moieties: it is therefore clear that this bridge does not give any advantages in terms of improved properties such as fade rate or colour intensity.
- Zhao and Carreira JACS 2002, 124, 8, p1582 have prepared bis-naphthopyrans linked by a bis-thiophene, by phenyl groups (Organic Letters, 2006, VoI 8 No. 1 , p99) and by oligothiophenes (Chenn. Eur. J.
- Coelho et al (Tetrahedron, 2005, 61 , p11730) have linked pyrans by means of phenyl, phenyl-O- phenyl, and phenyl-CH 2 CH 2 -phenyl bridges.
- Great Lakes (WO 00/39245) claim a trimeric species where three oxazines are attached to a central triazine.
- Great Lakes (WO 00/05325 and WO 00/21968) also claim compounds where two, three or four oxazines are linked to a central tetramethylcyclotetrasiloxane ring.
- a bi- photochromic molecule comprising two photochromic moieties linked via a polydialkylsiloxane oligomer.
- bi-photochromic molecule having the structure set out in claim 4.
- an ophthalmic lens comprising a bi-photochromic molecule according to the invention.
- the invention provides a polymeric host material comprising a bi- photochromic molecule according to the invention.
- the molecules exhibit a considerable improvement in the rate of fade in polymer matrices compared to the parent photochromic molecules.
- the compounds of the invention often exhibit increased strength of photochromic colour compared to the parent photochromic molecule, allowing for molecular weight and the number of photochromic units present.
- the compounds of the invention are particularly useful for use in photochromic ophthalmic lenses. It has also unexpectedly been found that these molecules have improved heat stability when incorporated into polymers, compared to the individual photochromic molecules which are not linked by the bridging group. This allows the molecules of the invention to be incorporated into polymers which require higher processing temperatures than are compatible with the unlinked photochromic molecules.
- the molecules of this invention also have the beneficial property of a lower yellowness index compared to the individual photochromic molecules which are not linked via a polydialkylsiloxane oligomer when processed at the same temperature in the same polymer.
- the compounds of the invention have advantages of improved fade rate, improved photochromic colour strength, increased heat stability and reduced yellowness index when compared to the known bi-photochromic compounds comprising bridging groups.
- two photochromic molecules are linked by means of a bridge which comprises a linking group at each end of a central polydialkylsiloxane (PDAS) chain to provide novel polydialkylsiloxane bridged bi- photochromic molecules.
- PDAS polydialkylsiloxane
- the bridge consists of a linking group at each end of a central PDAS chain.
- the photochromic units may be the same or different, allowing for the possibility of different chromophores with different fade rates to be present in the same molecule.
- the molecules of the invention comprise two photochromic moieties or molecules linked via a polydialkylsiloxane chain.
- the polydialkylsiloxane bridge, or linker comprises a linking group at each end.
- the bridge, or linker consists of a linking group at each end of a central polydialkylsiloxane chain. Any suitable polydialkylsiloxane chain and linking groups may be employed.
- the compounds are of the general formula: PC-L-PDAS-U-PC wherein PC and PC represent a photochromic moiety; PDAS represents a polydialkylsiloxane chain; and L and L' represent linking groups.
- PC and PC may be the same or different. It is particularly preferred that PC and PC independently represent photochromic moieties of general structure I to IV:
- R1 and R2 independently represent hydrogen, linear or branched C 1-10 alkyl, linear or branched Ci- I0 alkoxy, C 1 . 10 hydroxyalkoxy, C-MO alkoxy(Ci_io)alkoxy, phenyl, Ci-io alkoxyphenyl, halogen, C 1 . 5 haloalkyl, C 1 - 5 alkylamino, Ci -5 dialkylamino, arylamino, diarylamino, aryl C 1 . 5 alkylamino, or a cyclic amino group;
- R3 represents hydrogen, linear or branched C 1-10 alkyl, C 3 -C20 cycloalkyl, C 6 -C 2 O bicycloalkyl, linear or branched C 2- io alkenyl, linear or branched C 1-10 alkoxy, C 1-10 hydroxyalkyl, C 1-10 aminoalkyl, linear or branched Ci -20 alkoxycarbonyl, carboxyl, halogen, aryloxycarbonyl, formyl, acetyl or aroyl;
- R4 represents phenyl, C 1- - I0 alkoxyphenyl, Ci- 10 dialkoxyphenyl, C 1 - I0 alkylphenyl, Ci- 10 dialkylphenyl, in addition to those groups specified for R3;
- R5, R6, R7, R8, R9, R10, R14, R15, R16 are as defined above for R1 and R2;
- R11 represents linear or branched Ci_ 2 o alkyl, C3-C2 0 cycloalkyl, C 6 -C2o bicycloalkyl, (Ci -5 alkyl)aryl, (Ci -5 alkyl)cycloalkyl, (Ci -5 alkyl) bicycloalkyl, Ci -5 haloalkyl, Ci -5 dihaloalkyl or Ci -5 trihaloalkyl;
- R12 and R13 represent C-M O alkyl, Ci -5 alkyl alkoxycarbonyl, or together form a C 5-7 ring;
- R17 and R18 represent linear or branched C-MO alkyl, Ci_i 0 hydroxyalkyl, or together form a C 5-7 ring.
- L and L' which may be the same or different, represent a linking group. Any suitable linking group may be used. It is preferred that L and L' represent a linking group of the form
- Y is independently oxygen or sulphur
- R19 is hydrogen or C-i-io linear or branched alkyl
- R20 is Ci-i 0 linear or branched alkyl
- p is an integer from 1 to 15
- r is an integer from 0 to 10
- Q is linear or branched Ci-i 0 alkyl, C-M O alkenyl or 1 ,2-, 1 ,3, or 1 ,4-substituted aryl, or substituted heteroaryl.
- Y is oxygen.
- Particularly preferred linker groups L and L' are:
- PDAS represents a polydialkylsiloxane chain.
- PDAS represents an oligomer of the form
- R19 is C-i.-to alkyl, and n is an integer of from 4 to 75.
- Polydialkylsiloxane oligomers are commercially available, for example from Gelest Inc, Shin-Etsu Chemical Co. Ltd; Chisso Corp; Toshiba Silicone Co. Ltd; and Toray-Dow Corning Co. Ltd.
- Suitable polydialkylsiloxane oligomers include, but are not limited to, polydimethylsiloxane oligomers, such that R19 is preferably methyl.
- n is between 6 and 30 inclusively.
- R19 is methyl and n is an integer of from 6 to 30.
- Preferred polydimethylsiloxane oligomers include the oligomers DMS-B12, DMS-C15, DMS-C16, DMS-C21, DMS-A11, DMS-A12, DMS-A15, DMS-A21 , DMS-A211 and DMS-A214 available from Gelest Inc; KF-6001, KF-6002, KF-6003, KF-8010, X-22- 160AS, X-22-162A, X-22-161A, X-22-161B and X-22-162C from Shin-Etsu; and Silaplane FM-44 from Chisso.
- oligomers DMS-B 12, DMS- C15, DMS-C16, DMS-C21, DMS-A11, DMS-A12, DMS-A15, DMS-A21 , DMS-A211 and DMS-A214 from Gelest are quoted as having the following structures and approximate molecular weight or molecular weight ranges.
- the Gelest nomenclature is used to name the following polydimethylsiloxane oligomers, rather than the cumbersome (and not strictly accurate, as the oligomers are mixtures) systematic names.
- DMS-A12 Molecular weight range 900 - 1000 NH 2 - (CH 2 ) 3 —Si- ⁇ -f-Si-o-h ⁇ ii-(CH 2 ) 3 — NH 2
- polydimethylsiloxane oligomers are generally supplied either with an average molecular weight or a molecular weight range, and any number quoted as the number of repeat units of the dimethylsiloxane is to be interpreted as an average value.
- the parent photochromic compounds may be prepared as described in US 5,650,098 (1 ,2-b naphthopyrans), US 5,623,005 (2,1-b naphthopyrans), US 5,446,151 (2,1-b naphthoxazines), and US 6,303,673 (1 ,2-b naphthoxazines).
- linking group is attached to the commercially available oligomer, if required, and this reagent is then reacted with the parent photochromic compound to give the polydialkylsiloxane-bridged bi-photochromic molecule.
- the linking group may also be attached to the parent photochromic compound, which is then reacted with the commercially available oligomer to give the polydialkylsiloxane-bridged bi-photochromic molecule. Suitable reaction conditions will be apparent to the skilled person.
- polydimethylsiloxane oligomers are supplied either with an average molecular weight or a molecular weight range, and any number quoted as the number of repeat units of the dimethylsiloxane is to be interpreted as an average value. Accordingly, any yields quoted in the following Examples are inevitably approximate.
- the oligomers DMS-B12, DMS-C15, DMS-C16 and DMS-A214 are available from Gelest Inc. and are quoted as having the following structures and approximate molecular weight or molecular weight ranges.
- the reagent bis-phthaloyl-DMS-C15 was prepared in analogous fashion to bis-succinyl- DMS-C15 in Example 1 , using an equivalent quantity of phthalic anhydride in place of succinic anhydride.
- Example 5 (1.3-Dihvdro-3,3-dimethyl-1-neopentyl-6'-(4"-N-ethyl, N- (succinvlethvl)anilino)spiror2H-indole-2,3'-3H-naphtho ⁇ ,2-biM ,41oxazine) ? - DMS-C 15
- TLC thin layer chromatography
- Example 7 (1.3-Dihvdro-3,3-dimethyl-1-isobutyl-9'-succinyl-spiror2H-indole-2,3'-3H- naphthor2,1-bi ⁇ ,41oxazine)g-DMS-C16
- Dicyclohexyl carbodiimide (0.90 g) was added, and the mixture stirred for 2 hours at room temperature. TLC (5:1 toluene:EtOAc) indicated that the two starting material photochromies had been consumed. The mixture was filtered to remove dicyclohexyl urea, which was washed with toluene (5 ml). The solution was used for chromatography, eluting with a mixture of toluene and ethyl acetate.
- Example 11 (1 ,3-Dihvdro-3,3-dimethyl-1 -neopentyl-9'-succinyl-spiror2H-indole-2,3'- 3H-naphthor2.1-biri .4loxazine1) ? -DMS-A214
- 2,2-Bis(4'-methoxyphenyl)-5-hydroxymethyl-6-methyl-2H-naphtho[1 ,2-b]pyran was mixed with bis-succinyl-DMS-C15 (2.0 g), toluene (20 ml) and dimethylaminopyridine (0.05 g). This was stirred for 2 minutes, then dicyclohexyl carbodiimide (0.51 g) was added. The mixture was stirred for 45 minutes and TLC (3:1 toluene: EtOAc) indicated a main spot for polydialkylsiloxane-bridged bi-photochromic product, with effectively no starting material remaining. The mixture was cooled in an ice bath for 1 hour, then was filtered and the dicyclohexyl urea washed with toluene (5 ml).
- the parameter "Adjusted Delta Abs” allows for the molecular weight of the polydialkylsiloxane-bridged bi-photochromic compound, the molecular weight of the unbridged comparative compound and the number of photochromic units present. This is calculated as follows:
- Adjusted Delta Abs (Delta Abs Example compound x (MoI Wt example compound)/(Mol Wt comparative compound))/Number of photochromic units present in Example compound
- Example 10 which has a different photochromic unit at each end of the chain, the absorptions from each photochromic unit are treated separately.
- the Ti # values for the tailed dimers are between 29.4% and 65.4% of the T 1/2 values of the corresponding comparative compounds.
- the T 3/ 4 values of the tailed dimers show even greater improvements, being between 13.9% and 40.0% of the T 3/4 values of the corresponding comparative compounds.
- Samples of compounds of Example 7 and Example 12 and the corresponding comparative compounds C4 and C2 were incorporated at 250 ppm into polycarbonate, and polystyrene at different processing temperatures using a Boy 35M injection moulding machine, giving rectangular chips.
- the chips were measured for absorption using the same equipment as was used for measuring lenses.
- the chips were measured for yellowness index (as ASTM D1925) using a Datacolor Spectraflash SF450 colour spectrometer.
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PCT/GB2009/002010 WO2010020770A1 (en) | 2008-08-18 | 2009-08-18 | Polydialkylsiloxane-bridged bi-photochromic molecules |
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US9139552B2 (en) | 2005-04-08 | 2015-09-22 | Transitions Optical, Inc. | Indeno-fused naphthopyrans having ethylenically unsaturated groups |
US8298453B2 (en) * | 2010-01-06 | 2012-10-30 | Korea University Research And Business Foundation | Photochromic material |
US8287775B2 (en) * | 2010-02-17 | 2012-10-16 | Korea University Research And Business Foundation | Photochromic material |
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WO2019018625A1 (en) * | 2017-07-19 | 2019-01-24 | The Procter & Gamble Company | FUNCTIONALIZED SILOXANE POLYMERS AND COMPOSITIONS COMPRISING THESE POLYMERS |
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US11866648B2 (en) | 2019-01-30 | 2024-01-09 | Mitsui Chemicals, Inc. | Process for producing polymerizable composition for optical materials |
AU2020250724A1 (en) | 2019-04-03 | 2021-10-28 | Tokuyama Corporation | Photochromic optical article and method for manufacturing same |
WO2020230016A1 (en) | 2019-05-13 | 2020-11-19 | Alcon Inc. | Method for producing photochromic contact lenses |
WO2020230882A1 (ja) | 2019-05-16 | 2020-11-19 | 三井化学株式会社 | 光学材料用重合性組成物およびその用途 |
TW202140597A (zh) | 2020-02-28 | 2021-11-01 | 日商德山股份有限公司 | 濕氣硬化型聚胺酯組成物及積層體 |
JP2023161056A (ja) | 2020-08-31 | 2023-11-06 | 三井化学株式会社 | 光学材料用重合性組成物およびフォトクロミックレンズ |
CN113388114A (zh) * | 2021-01-11 | 2021-09-14 | 浙江赢科新材料股份有限公司 | 一种双端羧烃基封端含羧醚基结构的聚硅氧烷及其制备方法 |
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CN114031594B (zh) * | 2021-09-10 | 2023-06-20 | 江苏视科新材料股份有限公司 | 一种双苯并色烯类化合物及其应用 |
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