WO2005047277A1 - Pyrannes a fusion photochromique substitues par phenyle portant un groupe uree ou carbamyle - Google Patents

Pyrannes a fusion photochromique substitues par phenyle portant un groupe uree ou carbamyle Download PDF

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Publication number
WO2005047277A1
WO2005047277A1 PCT/US2004/034978 US2004034978W WO2005047277A1 WO 2005047277 A1 WO2005047277 A1 WO 2005047277A1 US 2004034978 W US2004034978 W US 2004034978W WO 2005047277 A1 WO2005047277 A1 WO 2005047277A1
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Prior art keywords
group
carbon atoms
linear
branched alkyl
alkyl group
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PCT/US2004/034978
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English (en)
Inventor
Olivier Breyne
You-Ping Chan
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Corning Incorporated
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Priority claimed from EP03292764A external-priority patent/EP1529780B1/fr
Application filed by Corning Incorporated filed Critical Corning Incorporated
Priority to JP2006539536A priority Critical patent/JP4745978B2/ja
Publication of WO2005047277A1 publication Critical patent/WO2005047277A1/fr

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    • 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
    • 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

Definitions

  • the present invention relates to benzo-, naphtho- and phenanthropyran type organic compounds having photochromic properties, preparation thereof and photochromic composition, and articles containing them.
  • the present invention relates to such photochromic compounds substituted by carbamated or ureated phenyls, preparation thereof and photocliromic compositions and articles containing them.
  • the present invention is useful, for example, in the manufacture of ophthalmic lenses, optical devices and window panes.
  • Photochromic compounds are those capable of reversible color change under the influence of electromagnetic radiation at certain wavelengths.
  • certain photochromic compounds may exhibit a different color when exposed to ultraviolet (UV) radiation or sunlight, and return to their initial colors when the such exposure ceases. Such returning to the initial color may be effected alternatively by thermal treatment and/or exposure to an electromagnetic radiation at a different wavelength.
  • Photochromic compounds find application in various fields, for example, for the manufacture of photochromic ophthalmic lenses, contact lenses, solar protection glasses, filters, camera optics or photographic apparatus optics or other optical devices and observation devices, glazing, decorative objects, bill elements or even for information storage by optical inscription (coding).
  • the photochromic compounds sometimes referred to as photochromic dyes, confer photochromic properties to these manufactured articles.
  • a photochromic lens comprising one or more photochromic compounds has the following traits: a high transmission in the absence of ultraviolet light; a low transmission (high colorability) under solar irradiation; acceptable coloration and discoloration kinetics; a tint desired by the consumer (preferably grey or brown) with preferably a maintenance of the chosen tint during the coloration and discoloration of the lens; maintenance of the performance and properties within a temperature range of 0-40°C; and a significant durability, as they are sophisticated and expensive products.
  • the coloration and discoloration kinetics of the (two or more) supplementary photochromic dyes may be advantageously essentially identical.
  • photochromic compounds have the following reduced formulae (FI), (FT) and (FI"):
  • United States Patent No. 5,645,767 describes naphthopyrans (F2) having an indeno group linked to the 5- and 6-carbons of the 2H-naphthopyran skeleton: (F2) [0009] United States Patent No. 5,651,923 describes 2H-naphthopyrans (F3, F4) having a naphthofurano or benzo group linked to the 5- and 6-carbons of the 2H-naphthopyran skeleton:
  • United States Patent No. 5,783,116 describes derivatives of 2H-naphthopyrans (F5, F6) having a non-substituted alicyclic group:
  • WO 01/36406 discloses 3H-naphthopyran derivatives (F7, F8) having a benzo 5- or 6-membered aliphatic ring linked to the 5- and 6-carbon of the 3H-naphthopyran skeleton:
  • United States Patent No. 6,506,538 describes a group of photochromic 2H- naphthopyran compounds having the following general formula (F9) wherein the annelated ring (A) can be (F9-1), (F9-2), (F9-3), (F9-4) and (F9-5):
  • Japanese Patent Application Publication No. 2001-114775 describes compounds where the group ⁇ R ⁇ is a phenyl substituted on the para position by an amine substituted by electro-attracting groups such as sulphonyls or acetyls.
  • An example compound as disclosed in this document has the following formula (F10):
  • the inventors of the present invention discovered a group of new compounds having a combination of the desired bathochromic shift in their absorption bands compared with analogous compounds having alkoxy, and, unexpectedly, advantageous photochromic properties, notably more rapid discoloration than those having sulphonyls or acetyls.
  • Ri represents a group
  • R 5 represent linear or branched alkyl group having 1 to 12 carbon atoms, a benzyl, naphthyl or phenyl group optionally substituted by at least one linear or branched alkyl group having 1 to 6 carbon atoms;
  • R 2 and R 3 are defined as follows: (A)R represents one of the following groups: (Al) a hydrogen; (A2) a linear or branched alkyl group having 1 to 12 carbon atoms, advantageously 1 to 6 carbon atoms; (A3) a cycloalkyl group having 3 to 12 carbon atoms; (A4) a phenyl or benzyl group, optionally substituted; (A5) a linear or branched alkoxy group having 1 to 12 carbon atoms, advantageously 1 to 6 carbon atoms; and (A6) a group
  • R 3 represents one of the following groups: (Bl) a hydrogen; (B2) a linear or branched alkyl group having 1 to 12 carbon atoms, advantageously 1 to 6 carbon atoms; (B3) a cycloalkyl group having 3 to 12 carbon atoms; (B4) a phenyl or benzyl group, optionally substituted; and (B5) a linear or branched alkoxy group having 1 to 12 carbon atoms, advantageously 1 to 6 carbon atoms; or (C) the R 2 and R groups, taken together, form an aromatic or non-aromatic cyclic group having one ring or two annelated rings which can comprise at least one heteroatom selected from the group consisting of: oxygen, sulfur and nitrogen; the aromatic or non-aromatic rings being independently 5 to 7-membered; and (3) the group
  • R in formula (I) is hydrogen.
  • branched alkyl and alkoxy groups as defined herein should comprise sufficient number of carbon atoms in order that they can be branched.
  • the compound of the present invention can be benzo-, 2H-naphtho-, 3H-naphtho- or phenanthropyran type compounds.
  • the group must not comprise groups that prevent the, opening of the pyran ring which imparts the photochromic properties to the compounds.
  • the compound of the present invention has one of the following general formulae (I a ), (l b ), (I c ) and (I d ):
  • Ri, R 2 and R 3 have the same definition as given supra in relation to formula (I);
  • R 6 represents: (bl) a hydroxy;
  • (b2) a linear or branched alkyl comprising 1 to 6 carbon atoms;
  • (b3) a linear or branched alkoxy group comprising 1 to 6 carbon atoms;
  • R' and R identical or different, independently represent a linear or branched alkyl group comprising 1 to 6 carbon atoms, a phenyl group optionally substituted with at least one linear or branched alkyl group comprising 1 to 6 carbon atoms, or together with the nitrogen atom to which they are bound represent a 5- to 7-membered ring which can comprise at least one other heteroatom selected from oxygen, sulfur and nitrogen, said nitrogen being optionally substituted with an R'" group, which is a linear or branched alkyl group comprising 1 to 6 carbon atoms;
  • R 7 represents: (cl) a halogen, and notably fluorine, chlorine or bromine; (c2) a hydroxy; (c3) a linear or branched alkyl group comprising 1 to 12 carbon atoms (advantageously 1 to 6 carbon atoms); (c4) a cycloalkyl having 1-12 carbon atoms; (c5) a linear or branched alkoxy group comprising
  • R ⁇ — '' group where R' and R", identical or different, represent independently a linear or branched alkyl group comprising 1 to 6 carbon atoms, a phenyl group optionally substituted with at least one linear or branched alkyl group comprising 1 to 6 carbon atoms, or together with the nitrogen atom to which they are bound represent a 5- to 7-membered ring which can comprise at least one other heteroatom selected from oxygen, sulfur and nitrogen, said nitrogen being optionally substituted with an R'" group, which is a linear or branched alkyl group comprising 1 to 6 carbon atoms; (c7.12) a methacryloyl group or an acryloyl group; (c8) an aralkyl or heteroaralkyl group, wherein the alkyl group, which is linear or branched, comprises 1 to 4 carbon atoms, and the aryl and heteroaryl groups have the same definition as those given supra in (c7);
  • (c9) a phenoxy or naphthoxy group optionally substituted with at least one linear or branched alkyl or alkoxy group comprising 1 to 12 carbon atoms, (clO) an amine, amide, carbamate or urea group: -NH 2 , -NHR, -NHCOR, - NR'COR, -NHCOOR, -NHCONHR, -CONH 2 , -CONHR, R ⁇ R'- " > ⁇ -N or -CO N R!' R ⁇ wherein R represents a linear or branched alkyl group comprising 1 to 6 carbon atoms, or a phenyl group optionally substituted with at least one linear or branched alkyl group comprising 1 to 6 carbon atoms; and R' and R", identical or different, represent independently a linear or branched alkyl group comprising 1 to 6 carbon atoms, a phenyl group optionally substituted with at least one linear or branched alkyl group
  • R represents a linear or branched alkyl group comprising 1 to 6 carbon atoms, or a phenyl group optionally substituted with at least one linear or branched alkyl group comprising 1 to 6 carbon atoms
  • R' and R identical or different, represent independently a linear or branched alkyl group comprising 1 to 6 carbon atoms, a phenyl group optionally substituted with at least one linear or branched alkyl group comprising 1 to 6 carbon atoms, or together with the nitrogen atom to which they are bound represent a 5- to 7-membered ring which can comprise at least one other heteroatom selected from oxygen, sulfur and nitrogen, said nitrogen being optionally substituted with an R'" group, which is a linear or branched alkyl group comprising 1 to 6 carbon atoms; (d 11 ) an -OCORi i or -OCOORi ⁇ group, Ri i representing a linear or branched alkyl group comprising 1 to 6 carbon atoms, or
  • R' and R identical or different, independently represent a linear or branched alkyl group comprising 1 to 6 carbon atoms, a phenyl group optionally substituted with at least one linear or branched alkyl group comprising 1 to 6 carbon atoms, or together with the nitrogen atom to which they are bound represent a 5- to 7-membered ring which can comprise at least one other heteroatom selected from oxygen, sulfur and nitrogen, said nitrogen being optionally substituted with an R"' group, which is a linear or branched alkyl group comprising 1 to 6 carbon atoms.
  • R' and R identical or different, independently represent a linear or branched alkyl group comprising 1 to 6 carbon atoms, a phenyl group optionally substituted with at least one linear or branched alkyl group comprising 1 to 6 carbon atoms, or together with the nitrogen atom to which they are bound represent a 5- to 7-membered ring which can comprise at least one other heteroatom selected from oxygen, sulfur and nitrogen, said nitrogen being
  • R l5 R 2 and R 3 have the same meaning as defined supra in relation to formula (I); wherein the condensation between (II) and (III) is advantageously effected in the presence of a catalyst, the catalyst being preferably selected from the group consisting of >-toluenesulfonic acid, dodecylsulfonic acid, camphorsulfonic acid or bromoacetic acid; or (2) the condensation reaction between: the formula (II) compound as defined in (i) supra in, this claim, and (iii) an aldehyde derivative corresponding to the following formula (III'):
  • R l9 R 2 and R 3 have the same meaning as defined supra in relation to formula (I); wherein the condensation reaction between (II) and (III') is advantageously effected in the presence of a metal complex, preferably a titanium complex, with titanium tetraethylate being particularly preferred.
  • the condensation reaction between compounds (II) and (III) or (IIIF) can be effected in a solvent such as toluene, xylene or tetrahydrofuran, optionally in the presence of additional catalysts.
  • a solvent such as toluene, xylene or tetrahydrofuran
  • additional catalysts for a more detailed description of the condensation between compounds (II) and (111'), one can refer to European Patent Application No. EP-A-0 562 915.
  • the present invention provides a photochromic composition comprising in part at least one photochromic compound of the present invention.
  • the photochromic composition may comprise one of the following: (1) a compound of the present invention, described supra; (2) a mixture of at least two compounds of the present invention, described supra; (3) a mixture of at least one compound of the present invention, described supra, and at least one other type of photochromic compound and/or at least one non-photochromic colorant; and (4) a linear or reticulated (co)polymer obtained by polymerization and or reticulation and/or grafting of at least one compound of the present invention, described supra.
  • the photocliromic composition of the present invention may constitute the chromenes having formula (I) as described supra, used separately or in combination with other chromenes of the present invention and/or with at least one other type of photochromic compound and/or with at least one non-photochromic colorant.
  • the photochromic composition of the present invention can comprise the compound (I) of the present invention as defied supra, and/or at least one linear or reticulated (co)polymer containing in the structure at least one compound (I) of the present invention.
  • This photochromic composition may comprise other type of photochromic compounds and/or at least one non-photochromic colorant and/or at least one stabilizer.
  • One skilled in the art can choose the photochromic compounds of another type, non-photochromic colorants and stabilizers to obtain desired properties of the composition once the photochromic compound of the present invention and the polymer are chosen.
  • combinations of photocliromic compounds of the present invention and or combinations of photochromic compounds of the present invention and photochromic compounds of another type according to the prior art are particularly recommended. Such combinations are interesting in that they may be suitable for generating grey or brown tints, which are particularly desired by consumers of applications such as ophthalmic spectacles or solar spectacles.
  • Those complementary photochromic compounds can be those known to one skilled in the art and described in the prior art, for example, chromenes (United States Patent Nos. 3,567,605; 5,238,981;
  • the photochromic composition according to the present invention can also comprise at least one of the following: - non-photochromic compounds for the adjustment of tint; - one or more stabilizers, for example, antioxidants; one or more anti-UV agents; one or more free radical scavengers; and - one or more photochromic excited state deactivators.
  • a photochromic solution can be obtained by dissolving at least one of the said compounds or compositions in an organic solvent such as toluene, dichloromethane, tetrahydrofuran or ethanol.
  • the solutions obtained are in general colorless and transparent. When exposed to sunlight, they develop a strong coloration and regain the colorless state when they are placed in an area of less exposure to the solar radiation or, in other words, when they are no longer subject to UV radiation.
  • a very low concentration of product is sufficient to obtain an intense coloration.
  • the compounds and photochromic compositions of the present invention are furthermore compatible with supporting matrices of organic polymer or of inorganic material, in a form included in said matrices as well as in the form of a coating on said matrices. These matrices may constitute part of the photochromic composition of the present invention.
  • the compounds of the invention are in fact those photocliromic compositions of the present invention in which the photochromic agents are dispersed within, near or on the surface of a matrix formed by a polymer, and/or copolymer and/or mixture of (co)polymers.
  • the photochromic agents including the compounds of the present invention, may be dispersed uniformly within the matrix, or distributed only in part of the matrix, such as the part near the surface uniformly or unevenly.
  • the compounds (I) of the present invention included in a polymer matrix are colorless or slightly colored in the initial un-darkened state and rapidly develop an intense coloration under UV radiation (365 nm) or under a light source similar to the solar radiation. They return to the initial coloration after the irradiation ceases to exit.
  • the method of implementation envisaged to obtain such a matrix varies widely.
  • the diffusion in the (co)polymer, from a suspension or solution of the photochromic compound, in a silicone oil, in an aliphatic or aromatic hydrocarbon, or in a glycol, or from another polymer matrix can be cited as examples.
  • the diffusion is commonly carried out at a temperature of 50 to 200°C for a period of time of 15 minutes to several hours, according to the nature of the polymer matrix.
  • Another implementation technique consists in mixing the photochromic compounds in a formulation of polymerizable mixture, depositing this mixture on a surface or in a mould, and then carrying out the copolymerization to form the matrix.
  • Polymers comprised of or selected from the following may be mentioned as examples of preferred polymer materials for forming matrices and/or the photochromic composition of the present invention which are useful in optical applications of the photochromic compounds according to the present invention:
  • the photochromic compounds of the present invention are used with resins which have a nanobiphasic structure and which are obtained by copolymerizing at least two different, specific difunctional monomers.
  • resins have been described in the French Patent Publication No. FR-A-2 762 845.
  • the amount of the photochromic compounds in the (co)polymer matrix depends upon the properties of the compounds and matrix, and, the degree of darkening desired.
  • the photochromic agents may be dispersed uniformly within the body of the polymeric matrix, or may be distributed only in part of the matrix, such as in the near-surface parts. Or alternatively, the photochromic composition of the present invention may form a surface coating on the polymer matrix. Preferably, the photochromic agents, including the compounds of the present invention, are distributed uniformly within the polymer matrix.
  • Still another aspect of the present invention in relation to the formula (I) photochromic compounds is optical articles, such as ophthalmic or solar spectacles, comprising the photochromic compositions of the present invention, described supra.
  • the optical articles may comprise: at least one compound (I) according to the present invention; and/or at least one (co)polymer and/or reticulate formed, at least in part, from compound(s) of the present invention; and/or at least one matrix, as described supra, or an organic polymer material or of an inorganic material, or even of a hybrid inorganic-organic material, said matrix initially optionally comprising at least one compound of the present invention.
  • the articles which are more particularly covered by the present invention are ophthalmic lenses or photochromic solar lenses, window panes (such as those for buildings, locomotion engines and automobile vehicles), optical devices, decorative articles, solar protection articles, information storage, etc.
  • Example 8 (Comparative Example ⁇ : Synthesis of Compound fC2 ⁇
  • Example 9 (Comparative Example): Synthesis of Compound (C3)
  • Example 10 (Comparative Example): Synthesis of Compound CC4)
  • ⁇ ⁇ denotes the shortest wavelength of the absorption band on the visible spectrum of the solution of the compound after exposure to UV radiation
  • ⁇ denotes the longest wavelength of the absorption band on the visible spectrum of the solution of the compound after exposure to UV radiation
  • T ⁇ / denotes the discoloration time corresponding to 50% reduction of absorption at ⁇ 2 at 21°C.
  • ⁇ 2 of compound (1) is +5 nm higher than that of (C2); ⁇ 2 of compound (2) is +6 nm higher than that of (C4); ⁇ 2 of compound (5) is +11 nm higher than that of (C2); and ⁇ 2 of compound (6) is +12 nm higher than that of (C4).
  • ⁇ ⁇ and ⁇ 2 of compound (4) are +8 nm and +2 nm liigher, respectively. These values are small when compared to the gain observed for analogous compound (CI) having morpholino over (C2), which is +33 nm.
  • the compounds (1) and (2) of the present invention have similar absorption band (compounds (1) and (C3) have the same ⁇ ; ⁇ of compound (2) is +2 nm higher than that of (C5); ⁇ 2 of compound (5) is +6 nm higher than that of (C3); and ⁇ of compound (6) is +8 nm higher than that of compound (C5)).
  • the T 2 data clearly show that compounds (1) and (2) of the present invention are much more rapid in terms of discoloration than (C3) and (C5), and their discoloration kinetics are much closer to those analogous compounds having alkoxy ((C2) and (C4)).
  • Compounds (5) and (6) having urea functions also show more rapid discoloration than compounds (C2) and (C4) having acetamidos, respectively.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)

Abstract

L'invention concerne des nouveaux benzo-, naphto et phénanthrochromènes substitués par des phényles portant de l'urée ou du carbamate, de formule générale (I), dans laquelle R1 représente un groupe (ii) ou (iii). L'invention porte sur leur préparation, sur des compositions photochromiques et sur des articles les contenant. Cette famille de composés possède des propriétés photochromiques intéressantes et utiles, notamment en terme de bande d'adsorption et de vitesse de décoloration.
PCT/US2004/034978 2003-11-05 2004-10-22 Pyrannes a fusion photochromique substitues par phenyle portant un groupe uree ou carbamyle WO2005047277A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP2006539536A JP4745978B2 (ja) 2003-11-05 2004-10-22 カルバメート化または尿素化フェニルにより置換されたベンゾ−、ナフト−およびフェナントロクロメン、その調製およびそれを含有する組成物と製品

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
EP03292764.2 2003-11-05
EP03292764A EP1529780B1 (fr) 2003-11-05 2003-11-05 Pyrannes photochromes condensés substitués avec phényl portant un groupe carbamyl ou urea
US10/867,201 US7250120B2 (en) 2003-11-05 2004-06-14 Benzo-, naphtho- and phenanthrochromene substituted by carbamated or ureated phenyls, preparation thereof and compositions and articles containing them
US10/867,201 2004-06-14

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WO2005047277A1 true WO2005047277A1 (fr) 2005-05-26

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2009132842A1 (fr) * 2008-04-30 2009-11-05 Rodenstock Gmbh Naphtopyrannes photochromiques ayant un sous-motif terphényle doublement ponté
US8147726B2 (en) 2008-05-09 2012-04-03 Tokuyama Corporation Chromene compound

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2000015628A1 (fr) * 1998-09-11 2000-03-23 Corning S.A. Naphtopyranes accoles en c5-c6, leur preparation et compositions et matrices (co)polymeres les contenant
JP2001114775A (ja) * 1999-10-19 2001-04-24 Tokuyama Corp クロメン化合物
WO2001036406A1 (fr) * 1999-11-17 2001-05-25 Corning S.A. Naphtopyranes anneles en c5-c6 avec anneau de type indene ou dihydronaphtalene, et compositions et matrices renfermant lesdits composes
FR2837200A1 (fr) * 2002-03-14 2003-09-19 Corning Inc 3h-naphtopyranes anneles en c5 -c6 par un carbocycle de type dihydronaphtalene et les compositions et matrices (co)polymeres les renfermant

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2000015628A1 (fr) * 1998-09-11 2000-03-23 Corning S.A. Naphtopyranes accoles en c5-c6, leur preparation et compositions et matrices (co)polymeres les contenant
JP2001114775A (ja) * 1999-10-19 2001-04-24 Tokuyama Corp クロメン化合物
WO2001036406A1 (fr) * 1999-11-17 2001-05-25 Corning S.A. Naphtopyranes anneles en c5-c6 avec anneau de type indene ou dihydronaphtalene, et compositions et matrices renfermant lesdits composes
FR2837200A1 (fr) * 2002-03-14 2003-09-19 Corning Inc 3h-naphtopyranes anneles en c5 -c6 par un carbocycle de type dihydronaphtalene et les compositions et matrices (co)polymeres les renfermant

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
PATENT ABSTRACTS OF JAPAN vol. 2000, no. 21 3 August 2001 (2001-08-03) *

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2009132842A1 (fr) * 2008-04-30 2009-11-05 Rodenstock Gmbh Naphtopyrannes photochromiques ayant un sous-motif terphényle doublement ponté
US8486312B2 (en) 2008-04-30 2013-07-16 Rodenstock Gmbh Photochromic naphthopyrans having a double-bridged terphenyl sub-unit
US8147726B2 (en) 2008-05-09 2012-04-03 Tokuyama Corporation Chromene compound
US8308995B2 (en) 2008-05-09 2012-11-13 Tokuyama Corporation Chromene compound

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