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US 8,308,996 B2Granted
Chromene compound
AssigneeTokuyama Corporation
InventorsToshiaki Takahashi, Junji Takenaka, Junji Momoda, Kazuhiro Teranishi
Life of this patent
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Abstract
A photochromic chromene compound which develops a color of a neutral tint, has high color optical density, a high fading speed and high durability, and has an indeno(2,1-f)naphtho(1,2-b)pyran structure represented by the following formula as the basic skeleton, wherein a sulfur-containing substituent selected from thiol group, alkylthio group, alkoxyalkylthio group, haloalkylthio group, cycloalkylthio group, arylthio group and heteroarylthio group is bonded to the 6-position and/or 7-position carbon atom(s).
Claims8
A chromene compound having a skeleton represented by the following formula (2):
- wherein (i) R1 and R2 are each a sulfur-containing substituent selected from the group consisting of thiol group, alkylthio group, alkoxyalkylthio group, haloalkylthio group, cycloalkylthio group, arylthio group and heteroarylthio group, (ii) R1 is the above sulfur-containing substituent and R2 is a hydrogen atom, hydroxyl group, alkyl group, haloalkyl group, cycloalkyl group, alkoxy group, amino group, heterocyclic group having a ring member nitrogen atom and bonded to the benzene ring to which the heterocyclic group bonds via the nitrogen atom, cyano group, nitro group, formyl group, hydroxycarbonyl group, alkylcarbonyl group, alkoxycarbonyl group, halogen atom, aralkyl group, aralkoxy group, aryloxy group or aryl group, or (iii) R2 is the above sulfur-containing substituent and R1 is a hydrogen atom, hydroxyl group, alkyl group, haloalkyl group, cycloalkyl group, alkoxy group, amino group, aliphatic heterocyclic group having a ring member nitrogen atom and bonded to the benzene ring to which the aliphatic heterocyclic group bonds via the nitrogen atom, cyano group, nitro group, formyl group, hydroxycarbonyl group, alkylcarbonyl group, alkoxycarbonyl group, halogen atom, aralkyl group, aralkoxy group or aryloxy group;
- R3 and R4 are each independently a hydroxyl group, alkyl group, haloalkyl group, cycloalkyl group, alkoxy group, amino group, heterocyclic group having a ring member nitrogen atom and bonded to the benzene ring to which the heterocyclic group bonds via the nitrogen atom, cyano group, nitro group, formyl group, hydroxycarbonyl group, alkylcarbonyl group, alkoxycarbonyl group, halogen atom, aralkyl group, aralkoxy group, aryloxy group or aryl group;
- R5 and R6 are each independently a group represented by the following formula (3):
- wherein R9 is an aryl group or heteroaryl group, R10 is a hydrogen atom, alkyl group or halogen atom, and m is an integer of 1 to 3, group represented by the following formula (4):
- wherein R11 is an aryl group or heteroaryl group, and n is an integer of 1 to 3, aryl group, heteroaryl group or alkyl group, and R5 and R6 may form an aliphatic hydrocarbon ring together with the carbon atom to which R5 and R6 bond;
- R7 and R8 are each independently a hydrogen atom, hydroxyl group, alkyl group, haloalkyl group, cycloalkyl group, alkoxy group, alkoxyalkyl group, formyl group, hydroxycarbonyl group, alkylcarbonyl group, alkoxycarbonyl group, halogen atom, aralkyl group, aralkoxy group, aryloxy group or aryl group, and R7 and R8 are bonded together to form an aliphatic ring having 3 to 20 ring member carbon atoms, condensed poly-ring having an aromatic ring or aromatic hetero ring condensed to the aliphatic ring, hetero ring having 3 to 20 ring member atoms, or condensed poly-ring having an aromatic ring or aromatic hetero ring condensed to the hetero ring, together with the 13-position carbon atom to which R7 and R8 bond, a is an integer of 0 to 2, b is an integer of 0 to 4, when a is 2, two R3's may be the same or different, and when b is 2 to 4, a plurality of R4's may be the same or different.
3 more elements
A naphthol compound represented by the following formula (7):
- wherein (i) R1 and R2 are each a sulfur-containing substituent selected from the group consisting of thiol group, alkylthio group, alkoxyalkylthio group, haloalkylthio group, cycloalkylthio group, arylthio group and heteroarylthio group, (ii) R1 is the above sulfur-containing substituent and R2 is a hydrogen atom, hydroxyl group, alkyl group, haloalkyl group, cycloalkyl group, alkoxy group, amino group, heterocyclic group having a ring member nitrogen atom and bonded to the benzene ring to which the heterocyclic group bonds via the nitrogen atom, cyano group, nitro group, formyl group, hydroxycarbonyl group, alkylcarbonyl group, alkoxycarbonyl group, halogen atom, aralkyl group, aralkoxy group, aryloxy group or aryl group, or (iii) R2 is the above sulfur-containing substituent and R1 is a hydrogen atom, hydroxyl group, alkyl group, haloalkyl group, cycloalkyl group, alkoxy group, amino group, aliphatic heterocyclic group having a ring member nitrogen atom and bonded to the benzene ring to which the aliphatic heterocyclic group bonds via the nitrogen atom, cyano group, nitro group, formyl group, hydroxycarbonyl group, alkylcarbonyl group, alkoxycarbonyl group, halogen atom, aralkyl group, aralkoxy group or aryloxy group;
- R3 and R4 are each independently a hydroxyl group, alkyl group, haloalkyl group, cycloalkyl group, alkoxy group, amino group, heterocyclic group having a ring member nitrogen atom and bonded to the benzene ring to which the heterocyclic group bonds via the nitrogen atom, cyano group, nitro group, formyl group, hydroxycarbonyl group, alkylcarbonyl group, alkoxycarbonyl group, halogen atom, aralkyl group, aralkoxy group, aryloxy group or aryl group;
- R7 and R8 are each independently a hydrogen atom, hydroxyl group, alkyl group, haloalkyl group, cycloalkyl group, alkoxy group, alkoxyalkyl group, formyl group, hydroxycarbonyl group, alkylcarbonyl group, alkoxycarbonyl group, halogen atom, aralkyl group, aralkoxy group, aryloxy group or aryl group, and
- R7 and R8 are bonded together to form an aliphatic ring having 3 to 20 ring member carbon atoms, condensed poly-ring having an aromatic ring or aromatic hetero ring condensed to the aliphatic ring, hetero ring having 3 to 20 ring member atoms, or condensed poly-ring having an aromatic ring or aromatic hetero ring condensed to the hetero ring, together with the 13-position carbon atom to which R7 and R8 bond, a is an integer of 0 to 2, b is an integer of 0 to 4, when a is 2, two R3′s may be the same or different, and when b is 2 to 4, a plurality of R4's may be the same or different.
1 more element
Dependencies are inferred from the claim text.