发明名称 Photochromic compounds, compositions and articles
摘要 The present invention provides a compound represented by the Formula I:; wherein substituents R16 and R17′ are each independently selected from an electron withdrawing group have a Hammett σp value of from 0.05 to 0.85 and R17 is hydrogen.
申请公布号 US8859097(B2) 申请公布日期 2014.10.14
申请号 US201113253188 申请日期 2011.10.05
申请人 Transitions Optical, Inc. 发明人 Chopra Anu
分类号 G03C1/73;C09K9/02;C07D311/94 主分类号 G03C1/73
代理机构 The Webb Law Firm 代理人 The Webb Law Firm
主权项 1. A compound of Formula I wherein, R16 and R17′ are each independently selected from an electron withdrawing group having a Hammett σp value of from 0.05 to 0.85, and R17 is hydrogen; R18 is independently for each occurrence: hydrogen; halogen; C1-C6 alkyl; C1-C4 haloalkyl; C3-C7 cycloalkyl; substituted or unsubstituted phenyl; —OR29 or —OC(═O)R29, wherein R29 is hydrogen, C1-C6 alkyl, phenyl(C1-C3)alkyl, mono(C1-C6)alkyl substituted phenyl(C1-C3)alkyl, mono(C1-C6)alkoxy substituted phenyl(C1-C3)alkyl, (C1-C6)alkoxy(C2-C4)alkyl, C3-C7 cycloalkyl, or mono(C1-C4)alkyl substituted C3-C7 cycloalkyl, and said phenyl substituents are C1-C6 alkyl or C1-C6 alkoxy; a mono-substituted phenyl, said phenyl having a substituent located at the para position, wherein the substituent is: a dicarboxylic acid residue, a diamine residue, an amino alcohol residue, a polyol residue, —CH2—, —(CH2)t—, or —[O—(CH2)t]k—, wherein t is the integer 2, 3, 4, 5 or 6 and k is an integer from 1 to 50, the substituent being connected to an aryl group on another photochromic material; —N(R30)R31, wherein R30 and R31 are each independently hydrogen, C1-C8 alkyl, phenyl, naphthyl, furanyl, benzofuran-2-yl, benzofuran-3-yl, thienyl, benzothien-2-yl, benzothien-3-yl, dibenzofuranyl, dibenzothienyl, benzopyridyl, fluorenyl, C1-C8 alkylaryl, C3-C20 cycloalkyl, C4-C20 bicycloalkyl, C5-C20 tricycloalkyl or (C1-C6)alkoxy(C1-C6)alkyl, wherein said aryl group is phenyl or naphthyl, or R30 and R31 come together with the nitrogen atom to form a C3-C20 hetero-bicycloalkyl ring or a C4-C20 hetero-tricycloalkyl ring; a nitrogen containing ring represented by the following graphic formula IVA: wherein each —Y— is independently chosen for each occurrence from —CH2—, —CH(R32)—, —C(R32)2—, —CH(aryl)-, —C(aryl)2-, and —C(R32)(aryl)-, and Z is —Y—, —O—, —S—, —S(O)—, —SO2—, —NH—, —N(R32)—, or —N(aryl)-, wherein each R32 is independently C1-C6 alkyl or hydroxy(C1-C6)alkyl, each aryl is independently phenyl or naphthyl, m is an integer 1, 2 or 3, and p is an integer 0, 1, 2, or 3 and when p is 0, Z is —Y—; a group represented by one of the following graphic formulae IVB or IVC: wherein R34, R35, and R36 are each independently hydrogen, C1-C6 alkyl, phenyl, or naphthyl, or the groups R34 and R35 together form a ring of 5 to 8 carbon atoms and each R33 is independently for each occurrence from C1-C6 alkyl, C1-C6 alkoxy, or halogen and p is an integer 0, 1, 2, or 3; and unsubstituted, mono-, or di-substituted C4-C18 spirobicyclic amine, or unsubstituted, mono-, and di-substituted C4-C18 spirotricyclic amine, wherein said substituents are independently aryl, C1-C6 alkyl, C1-C6 alkoxy, or phenyl(C1-C6)alkyl; q is an integer from 0 to 2; s is an integer from 0 to 3; R19 and R20 are each independently: hydrogen; C1-C6 alkyl; C3-C7 cycloalkyl; allyl; substituted or unsubstituted phenyl; substituted or unsubstituted benzyl; chloro; fluoro; the group —C(═O)W, wherein W is hydrogen, hydroxy, C1-C6 alkyl, C1-C6 alkoxy, the unsubstituted, mono- or di-substituted aryl groups phenyl or naphthyl, phenoxy, mono- or di-(C1-C6)alkoxy substituted phenoxy, mono- or di-(C1-C6)alkoxy substituted phenoxy, amino, mono(C1-C6)alkylamino, di(C1-C6)alkylamino, phenylamino, mono- or di-(C1-C6)alkyl substituted phenylamino, or mono- or di-(C1-C6)alkoxy substituted phenylamino; —OR37, wherein R37 is C1-C6 alkyl, phenyl(C1-C3)alkyl, mono(C1-C6)alkyl substituted phenyl(C1-C3)alkyl, mono(C1-C6)alkoxy substituted phenyl(C1-C3)alkyl, C1-C6 alkoxy(C2-C4)alkyl, C3-C7 cycloalkyl, mono(C1-C4)alkyl substituted C3-C7 cycloalkyl, C1-C6 chloroalkyl, C1-C6 fluoroalkyl, allyl, or the group —CH(R38)Y″, wherein R38 is hydrogen or C1-C3 alkyl and Y″ is CN, CF3, or COOR39, wherein R39 is hydrogen or C1-C3 alkyl, or R37 is the group, —C(═O)W′, wherein W′ is hydrogen, C1-C6 alkyl, C1-C6 alkoxy, the unsubstituted, mono- or di-substituted aryl groups phenyl or naphthyl, phenoxy, mono-, or di-(C1-C6)alkyl substituted phenoxy, mono- or di-(C1-C6)alkoxy substituted phenoxy, amino, mono(C1-C6)alkylamino, di(C1-C6)alkylamino, phenylamino, mono- or di-(C1-C6)alkyl substituted phenylamino, or mono- or di-(C1-C6)alkoxy substituted phenylamino, wherein each of said phenyl, or naphthyl group substituents are independently C1-C6 alkyl or C1-C6 alkoxy; or a mono-substituted phenyl, said phenyl having a substituent located at the para position, wherein the substituent is: a dicarboxylic acid residue, a diamine residue, an amino alcohol residue, a polyol residue, —CH2—, —(CH2)t—, or —[O—(CH2)t]k—, wherein t is from an integer 2, 3, 4, 5 or 6 and k is an integer from 1 to 50, the substituent being connected to an aryl group on another photochromic material; or R19 and R20 together form an oxo group, a spiro-carbocyclic group containing 3 to 6 carbon atoms, or a spiro-heterocyclic group containing 1 to 2 oxygen atoms and 3 to 6 carbon atoms including the spirocarbon atom, said spiro-carbocyclic and spiro-heterocyclic groups being annellated with 0, 1 or 2 benzene rings; and B and B′ are each independently: an unsubstituted, mono-, di-, or tri-substituted phenyl or aryl group; 9-julolidinyl; or an unsubstituted, mono- or di-substituted heteroaromatic group chosen from pyridyl, furanyl, benzofuran-2-yl, benzofuran-3-yl, thienyl, benzothien-2-yl, benzothien-3-yl, dibenzofuranyl, dibenzothienyl, carbazoyl; benzopyridyl, indolinyl, and fluorenyl, wherein each of the phenyl, aryl and heteroaromatic substituents are each independently: hydroxyl, a group —C(═O)R40, wherein R40 is —OR41, —N(R42)R43, piperidino, or morpholino, wherein R41 is allyl, C1-C6 alkyl, phenyl, mono(C1-C6)alkyl substituted phenyl, mono(C1-C6)alkoxy substituted phenyl, phenyl(C1-C3)alkyl, mono(C1-C6)alkyl substituted phenyl(C1-C3)alkyl, mono(C1-C6)alkoxy substituted phenyl(C1-C3)alkyl, C1-C6 alkoxy(C2-C4)alkyl or C1-C6 haloalkyl, said halo substituent is chloro, fluoro, bromo or iodo, R42 and R43 are each independently C1-C6 alkyl, C5-C7 cycloalkyl, phenyl or substituted phenyl, the phenyl substituents being C1-C6 alkyl or C1-C6 alkoxy; an unsubstituted or mono-substituted group chosen from pyrazolyl, imidazolyl, pyrazolinyl, imidazolinyl, pyrrolinyl, phenothiazinyl, phenoxazinyl, phenazinyl, and acridinyl, each of said substituents being C1-C12 alkyl, C1-C12 alkoxy, phenyl, or halogen; a mono-substituted phenyl, said phenyl having a substituent located at the para position, wherein the substituent is: a dicarboxylic acid residue or derivative thereof, a diamine residue or derivative thereof, an amino alcohol residue or derivative thereof, a polyol residue or derivative thereof, —CH2—, —(CH2)t—, or —[O—(CH2)t]k—, wherein t is an integer 2, 3, 4, 5 or 6 and k is an integer from 1 to 50, the substituent being connected to an aryl group on another photochromic material; a group represented by one of: wherein K is —CH2— or —O—, and M is —O— or substituted nitrogen, provided that when M is substituted nitrogen, K is —CH2—, the substituted nitrogen substituents being hydrogen, C1-C12 alkyl, or C1-C12 acyl, each R44 being independently chosen for each occurrence from C1-C12, alkyl, C1-C12 alkoxy, hydroxy, and halogen, R45 and R46 each being independently hydrogen or C1-C12 alkyl, and u is an integer ranging from 0 to 2; or a group represented by: wherein R47 is hydrogen or C1-C12 alkyl, and R48 is an unsubstituted, mono-, or di-substituted group chosen from naphthyl, phenyl, furanyl, and thienyl, wherein the substituents are C1-C12 alkyl, C1-C12 alkoxy, or halogen; or B and B′ taken together form one of a fluoren-9-ylidene, mono-, or di-substituted fluoren-9-ylidene, each of said fluoren-9-ylidene substituents being independently chosen from C1-C12 alkyl, C1-C12 alkoxy, and halogen.
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