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WO2010020770A1 - Molécules bi-photochromiques pontées par polydialkylsiloxane - Google Patents

Molécules bi-photochromiques pontées par polydialkylsiloxane Download PDF

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WO2010020770A1
WO2010020770A1 PCT/GB2009/002010 GB2009002010W WO2010020770A1 WO 2010020770 A1 WO2010020770 A1 WO 2010020770A1 GB 2009002010 W GB2009002010 W GB 2009002010W WO 2010020770 A1 WO2010020770 A1 WO 2010020770A1
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photochromic
molecule according
photochromic molecule
alkyl
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Steven Michael Partington
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James Robinson Speciality Ingredients Ltd
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James Robinson Ltd
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Priority to US12/737,795 priority Critical patent/US20110190455A1/en
Priority to CN2009801389160A priority patent/CN102171274A/zh
Priority to EP09784948A priority patent/EP2337810A1/fr
Priority to BRPI0912910A priority patent/BRPI0912910A2/pt
Publication of WO2010020770A1 publication Critical patent/WO2010020770A1/fr
Anticipated expiration legal-status Critical
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    • 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
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B69/00—Dyes not provided for by a single group of this subclass
    • C09B69/10—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B69/00—Dyes not provided for by a single group of this subclass
    • C09B69/10—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds
    • C09B69/103—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds containing a diaryl- or triarylmethane dye
    • 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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Abstract

L'invention porte sur une molécule bi-photochromique comprenant deux fractions photochromiques reliées par un oligomère de type polydialkylsiloxane. L'invention porte également sur une lentille ophtalmique comprenant la molécule bi-photochromique. L'invention porte également sur une matière hôte polymère comprenant la molécule bi-photochromique.
PCT/GB2009/002010 2008-08-18 2009-08-18 Molécules bi-photochromiques pontées par polydialkylsiloxane Ceased WO2010020770A1 (fr)

Priority Applications (4)

Application Number Priority Date Filing Date Title
US12/737,795 US20110190455A1 (en) 2008-08-18 2009-08-18 Polydialkylsiloxane-bridged bi-photochromic molecules
CN2009801389160A CN102171274A (zh) 2008-08-18 2009-08-18 聚二烷基硅氧烷桥接的双光致变色分子
EP09784948A EP2337810A1 (fr) 2008-08-18 2009-08-18 Molécules bi-photochromiques pontées par polydialkylsiloxane
BRPI0912910A BRPI0912910A2 (pt) 2008-08-18 2009-08-18 molécula bifotocromática, lente oftálmica, material hospedeiro polimérico e método para manufaturar uma molécula bifotocromática

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GBGB0815109.4A GB0815109D0 (en) 2008-08-18 2008-08-18 Polydialkylsiloxane-bridged bi-photochromic molecules
GB0815109.4 2008-08-18

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Cited By (28)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2011096643A1 (fr) * 2010-01-06 2011-08-11 Korea University Research And Business Foundation Matière photochrome
WO2011102599A1 (fr) * 2010-02-17 2011-08-25 Korea University Research And Business Foundation Matériau photochrome
CN102965095A (zh) * 2011-09-01 2013-03-13 中国科学院福建物质结构研究所 一种无机/有机杂化光致变色材料及其制备方法与应用
WO2013078086A1 (fr) * 2011-11-22 2013-05-30 Transitions Optical, Inc. Composés photochromes ayant au moins deux fractions photochromes
WO2015016364A1 (fr) 2013-08-02 2015-02-05 三井化学株式会社 Procédé de production pour matériau optique photochromique
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WO2015115648A1 (fr) 2014-02-03 2015-08-06 三井化学株式会社 Composition polymérisable pour matériau optique et matériau optique et lentille en plastique obtenue à partir de ladite composition
US9139552B2 (en) 2005-04-08 2015-09-22 Transitions Optical, Inc. Indeno-fused naphthopyrans having ethylenically unsaturated groups
US9522921B2 (en) 2015-04-13 2016-12-20 Sabic Global Technologies, B.V. Photochromic spirooxazine compounds
WO2018062385A1 (fr) 2016-09-30 2018-04-05 三井化学株式会社 Lentille photochromique et composition polymérisable
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WO2020230882A1 (fr) 2019-05-16 2020-11-19 三井化学株式会社 Composition polymérisable pour matériau optique et son utilisation
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US9028728B2 (en) 2005-04-08 2015-05-12 Transitions Optical, Inc. Photochromic materials that include indeno-fused naphthopyrans
US8647538B2 (en) 2005-04-08 2014-02-11 Transitions Optical, Inc. Photochromic compounds having at least two photochromic moieties
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
WO2011096643A1 (fr) * 2010-01-06 2011-08-11 Korea University Research And Business Foundation Matière photochrome
US8801976B2 (en) 2010-01-06 2014-08-12 Korea University Research And Business Foundation Photochromic material
WO2011102599A1 (fr) * 2010-02-17 2011-08-25 Korea University Research And Business Foundation Matériau photochrome
US8287775B2 (en) 2010-02-17 2012-10-16 Korea University Research And Business Foundation Photochromic material
CN102965095A (zh) * 2011-09-01 2013-03-13 中国科学院福建物质结构研究所 一种无机/有机杂化光致变色材料及其制备方法与应用
WO2013078086A1 (fr) * 2011-11-22 2013-05-30 Transitions Optical, Inc. Composés photochromes ayant au moins deux fractions photochromes
WO2015016363A1 (fr) 2013-08-02 2015-02-05 三井化学株式会社 Composition polymérisable pour matériau optique photochromique
WO2015016364A1 (fr) 2013-08-02 2015-02-05 三井化学株式会社 Procédé de production pour matériau optique photochromique
WO2015115648A1 (fr) 2014-02-03 2015-08-06 三井化学株式会社 Composition polymérisable pour matériau optique et matériau optique et lentille en plastique obtenue à partir de ladite composition
US9522921B2 (en) 2015-04-13 2016-12-20 Sabic Global Technologies, B.V. Photochromic spirooxazine compounds
KR20180039099A (ko) 2015-09-16 2018-04-17 미쯔이가가꾸가부시끼가이샤 광학 재료용 중합성 조성물, 당해 조성물로부터 얻어지는 광학 재료 및 플라스틱 렌즈
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US10711078B2 (en) 2015-09-16 2020-07-14 Mitsui Chemicals, Inc. Polymerizable composition, process for producing organic glass using the composition, and organic glass
US10921489B2 (en) 2015-09-16 2021-02-16 Mitsui Chemicals, Inc. Polymerizable composition for optical material, optical material obtained from the composition, and plastic lens
WO2018062385A1 (fr) 2016-09-30 2018-04-05 三井化学株式会社 Lentille photochromique et composition polymérisable
WO2019009230A1 (fr) 2017-07-03 2019-01-10 三井化学株式会社 Composition polymérisable pour matériaux optiques, et corps moulé
WO2019018625A1 (fr) * 2017-07-19 2019-01-24 The Procter & Gamble Company Polymères de siloxane fonctionnalisés et compositions comprenant ces polymères
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US12129332B2 (en) * 2018-01-25 2024-10-29 Nanogate Se Self-supporting photochromic polyurethane film, method of manufacturing the film, article comprising said film
WO2019156143A1 (fr) 2018-02-09 2019-08-15 三井化学株式会社 Verre et procédé de fabrication de verre
WO2019163728A1 (fr) 2018-02-23 2019-08-29 株式会社トクヤマ Corps multicouche fonctionnel et lentille fonctionnelle utilisant un corps multicouche fonctionnel
WO2019194281A1 (fr) 2018-04-05 2019-10-10 株式会社トクヤマ Composition adhésive photochromique, corps stratifié photochromique et article optique utilisant ledit corps stratifié photochromique
WO2019198664A1 (fr) 2018-04-12 2019-10-17 株式会社トクヤマ Article optique photochromique et son procédé de fabrication
WO2020158813A1 (fr) 2019-01-30 2020-08-06 三井化学株式会社 Procédé de production d'une composition polymérisable destinée à un matériau optique
WO2020204176A1 (fr) 2019-04-03 2020-10-08 株式会社トクヤマ Article optique photochromique et procédé pour sa fabrication
US11542353B2 (en) 2019-05-13 2023-01-03 Alcon Inc. Method for producing photochromic contact lenses
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KR101614824B1 (ko) 2016-04-22
EP2337810A1 (fr) 2011-06-29
KR20110084496A (ko) 2011-07-25
BRPI0912910A2 (pt) 2015-10-06
CN102171274A (zh) 2011-08-31

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