CA1272731A - Anthracene derivatives - Google Patents

Anthracene derivatives

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Publication number
CA1272731A
CA1272731A CA000488337A CA488337A CA1272731A CA 1272731 A CA1272731 A CA 1272731A CA 000488337 A CA000488337 A CA 000488337A CA 488337 A CA488337 A CA 488337A CA 1272731 A CA1272731 A CA 1272731A
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Prior art keywords
formula
residue
methyl
group
anthracene
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CA000488337A
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French (fr)
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Frederick H. Howell
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Ciba Geigy Investments Ltd
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Ciba Geigy AG
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
    • C07C15/20—Polycyclic condensed hydrocarbons
    • C07C15/27—Polycyclic condensed hydrocarbons containing three rings
    • C07C15/28—Anthracenes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/02—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
    • C07C233/11—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with carbon atoms of carboxamide groups bound to carbon atoms of an unsaturated carbon skeleton containing six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C22/00—Cyclic compounds containing halogen atoms bound to an acyclic carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C33/00—Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
    • C07C33/18—Monohydroxylic alcohols containing only six-membered aromatic rings as cyclic part
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F2/00—Processes of polymerisation
    • C08F2/46—Polymerisation initiated by wave energy or particle radiation
    • C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
    • C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
    • G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
    • G03F7/031—Organic compounds not covered by group G03F7/029
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/02—Ortho- or ortho- and peri-condensed systems
    • C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
    • C07C2603/22—Ortho- or ortho- and peri-condensed systems containing three rings containing only six-membered rings
    • C07C2603/24—Anthracenes; Hydrogenated anthracenes

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • General Physics & Mathematics (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Polymerisation Methods In General (AREA)
  • Epoxy Resins (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

Abstract

Abstract of Disclosure Anthracene Derivatives New compounds useful as sensitizers in photocurable polymer systems have the formula:

(I), wherein p is 1 or 2 and q is 0 or 1 provided that p+q is 1 or 2;
each R is independently a residue of formula:

-A-(Q)k (II), wherein A is a residue of formula (III), wherein n is an integer from 1-17, k is 1 or 2, R5 and R6 are the same or different and each is a straight- or branched chain alkyl group having 1 to 5 carbon atoms and, when Q is COOR2 either R5 or R6 is optionally substituted by a COOR2 group the R2 groups being the same or different, provided that when R5 or R2 is substituted by a COOH group (R2=H) then the compound of formula I does not contain more than three COOH groups or R5 or R6 may be linked to the residue CnH2n+1-k to form a C5-C12 cycloalkylene residue substituted by the group -(CO2R2)k wherein the R2 groups indepen-dently, have their previous significance and k has its previous significance; Q is a residue -COZR2 wherein Z is 0 or NR3 and R2 is H, straight- or branched chain alkyl having 1 to 18 carbon atoms, a straight- or branched chain alkenyl group having 3 to 18 carbon atoms, cycloalkyl having 3 to 12 carbon atoms or an aralkyl group having 7 to 9 carbon atoms and, when Z is -NR3, R3 is hydrogen or a straight- or branched chain alkyl group having 1 to 18 carbon atoms, or R2 and R3, together with the nitrogen atom to which they are each bonded, may form a 5- or 6-membered heterocyclic ring; or Q is a residue -OX wherein X is -R3 or -CoR4 wherein R3 is as above and is H, straight- or branched alkyl having 1 to 18 carbon atoms, a straight- or branched chain alkenyl group having 3 to 18 carbon atoms or cycloalkyl having 3 to 8 carbon atoms; a residue CN;
each R1, independently, is straight- or branched chain alkyl having 1 to 8 carbon atoms, aralkyl having 7 to 9 carbon atoms optionally substituted by one or two halogen atoms, an alkyl (C1-C4)-cyclo-alkyl(C5-C12) group, or R1 is a residue of formula II and, when R1 is a residue of formula II, then R1 and R may be the same or different;
and salts thereof with organic or inorganic bases.

Description

~ 3~l 3-15061/-tMAC 186 Anthracene Darivatives The pr~sent invention relates to new anthracene compound~, especially functionally alkylated anthracene compounds us~ful as ssnDltisors in the photo-crosslinking of resin system~.

Substitutld anthracene derivatives containing polar-group bearing substituents are known in the art. Thus M.5. New~an and S. Otzuka describe in J. Org. Chem., 23, 797 (1958) 1-snthryl derivatives carrying ftmctionally substituted alkyl groups. These alkyl groups may have a methyl group attached to the carbon atom that i6 bound to the anthracena ring and the~s alkyls carry polar groups, such as -COOH, -OH or -CN. The compounds are used a8 lnter~edlates for the preparation of 1,2-b~nzanthracenes.

P. Arjunan et al. describe ~n J. Org. Chem., 46, 626 (1981) 2-and i 9-anthrylalkane carboxylic acids and the corre~ponding esters. These ~ compounds are used as fluorescent probes in membranes.
:
According to the present invantlon, there are provided compounds having the formula:

~t (Rl )q~ + 5 ! +~ (R)p (I), wherein p is 1 or 2 and q ls O or 1 provided that p~q is 1 or 2, each R is independently a residue of for~ula:

`~

-- 2 -- .

-A-(Q)k (II), wherein Q ls a re~idue -COZR2 wherein Z i3 0 or NR3, and R2 ia H, straight or branched chain alkyl having from 1 to 18 carbon atoms, a straight or branched chain alkenyl group having 3 to 18 carbon atoms, a cycloalkyl group having from 3 to 12 carbon atom~ or an aralkyl group having 7 to 9 carbon atom~: and when Z is -NR3, R3 i3 hydrogen or a straight or branched chain alkyl group having from 1 to 8 carbon atom~l or R2 and R3, together ~ith the ni.trogen atom to which they are each bonded, may form a 5- or 6-membered heterocyclic ring; or Q i~ a re~idue -OX wherein X i3 R3 or CoR4, wherein R3 ha~
itB previous significance, and R" is H, a 3tralght- or branched chain alkyl group having from 1 to 18 carbon atoms, a C3-Cl~
~traight or branched chain alkenyl group or a C3-Cl 2 cycloalkyl group; a residue CN; k i~ 1 or 2, A i9 a residus of formula ~ ~CnH2n+1-k) (III), wherein n is an integer from 1-17, k is as defined above, Rs and R5 are ths sa~e o~ differ~nt and each i9 a straight- or branched chain alkyl group having 1 to 5 csrbon ato~s and, when Q i~ COORZ eithes Rs or R5 iB opt~onally substituted by a COOR2 group the R2 group~
being the same or different, prov~dQd that when Rs or R5 is sub-stituted by a COOH group (i.e. RZ~H), then tha co~pound of formula I
doss not contain more than three COOH group~ or R5 or R6 may be llnkod to the residue CnH2n+1_k to fo m 5 12 Y Y
residue sub~tituted by tha group -(CO2RZ)k wherein the R2 groups independently have thelr previous significance and k has ~ts previous significance; each Rl, independently, i5 a Cl-C~ ~traight- or branched chain alkyl, a C7-Cg aralkyl group, optionally ~ubstituted by one or two halogen atoms, an alkyl-(~1-C4~-cycloalkyl-(Cs-C12) group; or R1 ls a re~ldue of ~ 31L
_ 3 -formula ~I as hereinbeforQ d~fln~d, and when Rl 1~ a re~ldue of formula II, then Rl nnA R may be the same or diEorent; and ~alt~ o~
carboxyllc acld6 of Eormula I with organic or lnorganic bases.

~hen the group Rl i~ a Cl-ca ~traight- or branched chain alkyl group group it may be, for example~ a methyl, ethyl, n-propyl, i30propyl, n-butyl, iso-butyl, t-hutyl, t-pentyl, or 1,1,3,3-tetramethylbutyl r~?sidue.

When the groups R2, R3 or R~ are Cl~Cla straight or branch~d chain alkyl they may be the same or different snd may be e.g. methyl, athyl t n-propyl, iso-propyl, n-butyl, ~ec-butyl, n pentyl, n-hexyl, n-heptyl, n-octyl, 2-ethylhexyl, n-nonyl, n-decyl, n-dodecyl, n-hexadecyl or n-octadecyl.

When the groups Rs and R6 are Cl-C5 straight- or branched chain alkyl, they may be the same or different and may be e.g. methyl, ethyl, n-propyl, isopropyl, n-butyl, sec.-butyl or n-pentyl.

When R2 or R4 is a C3-Clg straight or branched chain alkenyl group, it may be for example, a prop-2-enyl, n but 2-enyl, 2-methyl-prop-2-enyl, n-pent-2-enyl, D-hex-2-enyl, n~hexa-2,4-dienyl, n-dec-10-0nyl, n-heptadec-~-enyl, or n-heptadec-8,11-dienyl group.

When the group R2 os Rt is a C3 C~2 cycloalkyl group, it ~ay be, for exampla, a cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclooctyl or cyclododecyl group.

When the groups R2 and R3, together with the nitrogen atom to which ~hey are bonded form a 5- or 6-membered heterocycllc ring this ring may be a pyrrolldin~, piperidin0 or morpholine ring.

When the group Rl is a C7-Cg aralkyl group, optionally substituted by one or ~wo halogen atoms it may be, for example, a benzyl, a-methyl-ben7yl, p-chloro-~-methyl-benzyl, cumyl, p-chlorocumyl or
2 ? 4-dichlorocumyl group.

When the group R2 iu a C7-Cg aralkyl group lt may be for example, a benzyl, ~-methylben~yl, or cumyl group.

When the growp R1 i9 an alkyl (C1-C4)-cycloalkyl-~Cs-C12) group it may be, for example, a 1-methyl-cyclopent-1-yl, l-methyl-cyclohex-1-yl, l-methyl-cyclohept-l-yl, l-methyl-cyclooct-l-yl, l-ethyl-cyclohex-l-yl or 1-n-butyl-cy&lohex-1-yl group.

Examples o~ ~alts where Q i9 an acidic group, e.g. COOH, include salts with al~all and alkaline esrth metals and amines.

Examples of aminss which caD form ~alts when Q is an acidic group include aliphatic- cycloallphatic-, aromatic-, araliphatic- and heterocycllc amines.

Exampleg of aliphatic amlnes are 1-20C aliphatic amine3 such as ethylamlne, triethylam~ne, decyl~mine, dodecylamine and o~ta-decylamine; examples of cycloaliphatic smineg are 5-8C cycloali-phatic amines ~uch as cyclohexylamine; examples of aromatic aminea are aniline and toluidine; an example of an araliphatic amine i9 benzylamlne; and heterocyclic amines lnclude morphol~ne and pyridine.

In one preferr~d embodiment p~q ~ 2, more prefarably the gro~ps R
and R1 are each a re6idue of formuls II, it i8 egpecially preferrPd that the residues of formula II are the same and are preferably bonded in the 2,6- or 2,7-positions of the anthracene molecule.

Othar preferred compoundg of the invention are tho~e having the formula IV

RI
Rt !~ i i ( IV), ~./ \,~ \0~

wherein R i8 a resldue of formula II as hereinbefore defined and R~
iB a residue of formula II, as hereinbefore defined, or is a Cl-C8 straight- or branched chain alkyl re~idue;
as well as ~alts thereof.

Yet other preferred compound~ are those wherein p-l and qeO~

Still other preferred compounds of formula I are those in which ~ is 1.

Partlcularly preferred compounds of formula I are those in which i8 1 and Q i8 a residue CO2R2 whereln R2 has its previous signi-ficance.

Non limiting examples of compound~ of formula I include:
2-(3-Methoxycarbonyl-2-methyl-prop-2-yl)-anthracene 2-(5-Carboxy-2-methyl-pent-2-yl)-anthracane and its sodium salt 2-(5-Methoxycarbonyl-2-methyl-pent-2-yl)-anthracene 2-(5-Ethoxycarbonyl-2-methyl-pent-2-yl)-anthracene 2-(5-n-Butoxycarbonyl-2-methyl-pent-2-yl)-anthracene 2-(5-n-Hexyloxycarbonyl-2-methyl-pent-2-yl)-anthracene 2-[5-(2-Ethylhexyloxycarbonyl)-2-methyl-pent-2-yl]snthrscene 2-(5-n-Decyloxycarbonyl-2-methyl-pent-2-yl)anthracene 2-(5-n-Octadecyloxycarbonyl-2-methyl-pent-2-yl)-anthracene 2-(7-Methoxycarbonyl-2,6-dimethyl-hept-2-yl)-anthracene 2-(5-N-n-Butylcarbamoyl-2-methyl-pent-2-yl)-anthracene 2-(7-Cyano-2,6-dimethyl-hept-2-yl)-anthracene 2-(6-Hydroxy-2-methyl-hex-2-yl)-anthracene 2-(6-Acetoxy-2-methyl-hex-2-yl)-anthracene 2-(8-Hydroxy-2,6-dimethyl-oct-2-yl)-anthracene 2-(6-Hydroxy-2,6-dimethyl-hept-2-yl~-anthracene 2-(8-Acetoxy-2,6,dimethyl-oct-2-yl)-anthracene 2-(8-Acryloyloxy-2,6-dimethyl-oct-2-yl)-anthracene 2-(8-Methoxy-2,6-dimethyl-hept-2-yl)-anthracene Ci8 and trans-2-(4-methoxycarbonyl-1-methyl-cyclohex-1-yl)-anthracene 73~
- 6 ~

2-t-Butyl-6-(3-methoxycarbonyl-2-methyl-prop-2 yl) anthraceno 2-t-Butyl-7-(3-methoxycarbonyl-2-methyl-prop-2 yl)-inthracene 2-(S-Car~oxy 2-methyl-pent-2-yl)-6-methyl-anthrscene and its ~odlum Ralt 2-(5-Carboxy-2 Methyl-pent-2-yl)-7-methyl-anthracene and it~ sodlum ~alt 2-~5-Methoxycarbonyl-2-methyl-pent-2-yl)-6-methyl-anthracene 2-(5-Methoxyca~bonyl-2-methyl-pent-2-yl)-7-methyl-anthracene 2-15-Etho~ycarbonyl 2-methyl-pent~2-yl)-6-methyl-anthracene 2-(5-Ethoxycarbonyl-2-methyl-pent-2 yl)-7-methyl-anthracene 2-~S-n-Butyloxycarbonyl-2-methyl-pent-2-yl)-6-methyl-anthracene 2-~5-n-Butyloxycarbonyl-2 methyl-pent-2-yl)-7-methyl~anthracene 2-(5 n-Hexyloxycarbonyl-2-methyl-pent-2-yl)-6-methyl-anthracens 2-~5-n-Hexyloxycarbonyl-2-methyl-pent-2-yl)-7-methyl-anthracene 2-(5-n-Decyloxycarbonyl-2-methyl-pent-2-yl)-6-methyl-anthracene 2-(S-n-Decyloxycarbonyl-2-methyl-pent-2-yl)-7-methyl-anthrAcene 2-Ethyl-6-(5-methoxycarbonyl-2-methyl-pent-2-yl~-anthracene 2-Ethyl-7-~5-methoxycarbonyl-2-methyl-pent-2-yl)-anthracene 2-t-Butyl-6-(S-carboxy-2-methyl-pent-2-yl)-anthracene and its sodium Ealt 2-t-Butyl-7-(5-carboxy-2-methyl-pent-2-yl)anthracene and its sodium æalt 2-t-Butyl-6-(S-methoxycarbonyl-2-methyl-pent-2-yl)-anthrscene 2-t-Butyl-7-(5-methoxycarbonyl-2-methyl-pent-2-yl)-anthracene 2-t-~utyl-6-[5-ethoxycsrbonyl-2-methyl-pent-2-yl)-anthracene 2-t-Butyl-7-(S-ethoxycarbonyl-2-methyl-pent-2-yl)-anthracene 2-t-Butyl-6-~5-n-propyloxycarbonyl-2-methyl-pent-2-yl)-anthraGene 2-t-Butyl-7-(5-n-propyloxycarbonyl-2-methyl-pent-2-yl)-anthracene 2-t-Butyl-6-(5-n-isopropyloxycarbonyl-2-~ethyl-pent-2-yl)-anthracene 2-t-Butyl-7-(5-n-isopropyloxycarbonyl-2-methyl-pent-2-yl)-anthracene 2-t-Butyl-6-(5-n-butyloxycarbonyl-2-methyl-pent-2-yl)-anthracene 2-t-Butyl-7-(5-n-butyloxycarbonyl-2-methyl-pent-2-yl)-anthracene 2-t-Butyl-S-(S-n-hexyloxycarbonyl-2-methyl-pent-2-yl)-anthracene 2-t-Butyl-7-(5-n-hexyloxycarbonyl-2-methyl-pent-2-yl~-anthracene 2-t-Butyl-6-L5-~2-ethylhexyloxycarbonyl)-2-methyl-pent-2-yl]-anthracene ~2~

2-t-Butyl-7-[5~(2-ethylhexyloxyclrbony~ 2-methyl-pent-2-yl~-anthr~cene 2-t Butyl-6-(n-decyloxycarbonyl 2-methyl-pent-2~yl)-anthracene 2-t-Butyl-7-(n-decyloxycarbonyl-2-methyl-pent-2-yl)-anthracene 2-t-Butyl-6-(cylcohexyloxycarbonyl-2-methyl-pent-2-yl~-anthracene 2-t-Butyl-6-(S-csrbamoyl-2-methyl-pent-2-yl)-anthracene 2-t-Butyl-6-(5-N-methylcarbamoyl-2-methyl-pent-2-yl)-anthracene 2-(1,1,3,3-tetramethylbutyl)-6-(S-methoxycarbonyl-2-methyl-pent-2-yl)-anthracene 2-(l,1,3,3-tetramethylbutyl)-7-(5-methoxycarbonyl-2-methyl-pent-2-yl)-anthracene 2-Cumyl-6-(5-methoxycarbonyl-2-methyl-pent-2-yl)-anthracene 2-Cumyl-7-(5-methoxycarbonyl-2-methyl-pent-2-yl)-anthracene 2-(l-methyl-cyclohex 1 yl)-6-(5-methoxycarbonyl-2-methyl-pent-2-yl)-anthracene 2-(1 methyl-cyclohex-l-yl)-7-(S-methoxycarbonyl-2-methyl-pent-2-yl)-anthracene 2-tert-Butyl-6-(7-methoxycarbonyl-2,6-dimethyl-hept 2-yl)-anthracene 2-tert-Butyl-7-(7-methoxycarbonyl-2,6-dimethyl-hept-2-yl)-anthracene 2-tert-Butyl 6-(7-cysno-2,6-di~ethyl-hept-2-yl)-anthracene 2-tert-Butyl-7-(7-cyano-2,6-dimethyl-hept-2-yl)-anthracene 2-tert-Butyl-6-(8 hydroxy-2,6-dimethyl-oct-2-yl)-anthracene 2-tert-Butyl-7-(8-hydroxy-2,6-d1methyl-oct-2-yl)-anthracene 2-tert-Butyl-6-(8-acetoxy-2,6-dimethyl-oct-2-yl)-~nthracene 2-tert-Butyl-7-(8-acetoxy-2,6-dim0thyl-oct-2-yl)-anthracene ci~ und trans 2-t-B~tyl-6-(4-methoxycarbonyl-1-methyl-cyclohex 1-yl)-anthracene cis und trans 2-t-Butyl-7-(4-methoxycarbonyl-1-methyl-cyclohex-l-yl)-~nthracene 2,6-Bis-(3-methoxycarbonyl-2-methyl-prop-2-yl~-anthracene 2,7-Bis-[3-methoxycarbonyl-2-methyl-prop-2-yl?-anthracene 2,6-Bis-(5-carboxy-2-methyl-pent-2-yl)-anthracene and its 30dium salt 2,7-Bis-(~i-carboxy-2-methyl-pent-2-yl)-anthracene and its sodium salt 2,6-Bis-(S-methoxycarbonyl-2-methyl-pent-2-yl)-anthracene 2,7-Bi~-(5-methoxycarbonyl-2-methyl-pent-2-yl)-anthracqne 2,6-Bi~-(5-ethoxycarbonyl-2-m~thyl-pqnl:-2~yl)-anthraccne 2,7-Bis-(5-ethoxycarbonyl-2-methyl-pent 2-y].)-anthracene 2,6-Bis-(S-n-propyloxycarbonyl-2-methyl-pent-2-yl)-anthracene 2,7-Bls-(5-n-propyloxycarbonyl-2-methyl-pent-2-yl)-anthracene 2,6-Bis-(5-n-isopropyloxycarbonyl-2-methyl-pent-2-yl)-anthracene 2,7-Bis-(5-n-lsopropyloxycarbonyl-2-methyl-pent-2-yl)-anthracene 2,6-Bi~-(5-n-butyloxycarbonyl-2-methyl-pent-2-yl)-anthracena 2,7-Bis-(5-n-butyloxycarbonyl-2-methyl-pent-2-yl)-anthracene 2,6-Bis-(5-n-hexyloxycarbonyl-2-methyl-pent-2-yl)-anthracene 2,7-Bis-(5-n-hexyloxycarbonyl-2-methyl-pent-2-yl)-anthracene 2,6~Bis-~5-(2-ethylhsxyloxycarbonyl?-2-methyl-pent-2-yl]anthracene 2,7-Bis-[5-(2-ethylhQxyloxycarbonyl)-2-methyl-pent-2-yl]anthracene 2,6-Bi~-(5-n-decyloxycarbonyl-2-methyl-pent-2-yl)-anthracene 2,7-B1~-(5-n-decyloxycarbonyl-2-methyl-pent-2-yl)-anthracene 2,6-Bis-(7-methoxycarbonyl-2,6-dimethyl-hept-2-yl~-anthracene 2,7-Bis-(7-methoxycarbGnyl-2,6-dimethyl-hept-2-yl)-anthracene 2,6-Bi~-(5-N,N-dimethylcarbamoyl-2-~ethyl-pent-2-yl)-anthracene 2,6-Bls-(5-N-n-butylcarbamoyl-2-methyl-pent-2-yl)-anthracene 2,7-Bis-(5-N-n-butylcarbamoyl-2-mathyl-pent-2-yl)-anthracene 2,7-Bis-(5-N-allylcarbamoyl-2-methyl-pent-2-yl)-anthracene 2,7-B~s-(5-N-cyclohexylcarbamoyl-2-methyl-pent-2-yl~-anthracene 2,7-Bis-(5-N-ben~ylcarbamoyl-2-methyl-pent-2-yl)-anthracene 2,7-Bis-(5-morpholinocarbonyl-2-methyl-pent-2-yl~-anthracene 2,6-Bis ~-cyano-2,6-dimethyl-hept-2-yl)-anthracane 2,7-Bi3-(7-cyano-2,6-dimethyl-hept-2-yl)-anthracene 296-Bis-(8-m~thoxy-2,6-dimethyl-hept-2-yl~-anthracene 2,7-Bis-(8-methoxy-2,6-dimethyl-hept-2-yl)-anthracene 2,6-Bls-(8-hydroxy-2,6-dimethyl-hept-2-yl) anthracene 2,7-Bis-(8-hydroxy-2,6-diemthyl-hept-2-yl?-anthracene 2,6~Bis-(8-acetoxy~2,6-dimethyl-hept-2-yl?-anthracene 2,7~Bis-(8-acetoxy-2,6-dimethyl-hept-2-yl)-anthracene 2,6-Bi~-(8-methoxy-2,6-dlmethyl-hept-2-yl)-anthracene 2,7-Bis-(8-methoxy-2,6-dimethyl-hept-2-yl)-anthracene 2,6-Bi~-(8-acryloyloxy-2,6-dimethyl-hept-2-yl?-anthracene 2,6-Bis-(8-cyclohexanoyloxy-2,6~dimethyl-hept-2-yl)-anthracene 2,6 Bi~-(4~methoxycarbonyl-l-methyl-cyclohex-1-yl)-anthrncene 2,7-B1~-(4--methoxyc~rbonyl-1-methyl-cyclohe~ yl)-anthr~cene The compound~ of formula I may be prepared by methods well known to thoae ~killed in the art, for instance they may be made by func-tional slkylatlon of anthracene, 2-methyl anthracene, 2-t-butyl anthracene, 2-(3-methoxycarbonyl-2-methyl-prop-2-yl)-anth~acene, 2-(5-methoxycarbonyl-2-methyl~pent-2-yl)-anthracene and the like.
Alternatively, compound~ of formula I may be prepared by first acylatlng anthracene, 2-methyl anthracene, 2-t-butyl anthracene, 2-(5 methoxycarbonyl-2-methyl-pent-2-yl?-anthracene, 2-(3-carboxy-propanoyl)-anthrscene and the like, with appropriate acylating agentg BUCh ag 8uccinic anhydride, glutaric anhydride, methyl
3-chloroformyl-propanoate, ethyl-S-chloroformyl-pentQnoate, methyl 9-chloroformyl-nonanoate and the like; followad by conversion of the acyl carbonyl into a hydrocarbyl residue, by known methods. Examples of such conversions to a hydrocarbyl residue are the converaion of the carbonyl group to a ~C(CH3)2 residue by geminal alkylation.

Gemlnal alkylation of the carbonyl group may be carried out for in~tance by the method describ0d by Weidmann and Seebach 9 Angew.Chem.Int.Ed., Engl. 22 (l983?, 31 45.

~hen the compounds of formula I contain two residues R or a residue R and a residue R~, then the functional acylation andJor acylations and conversion may be carried out in stepwise manner. When the two residues R or two resldues R and Rl are ldentical it 1~ convenient to introduca them simultaneously.

Mono-substituted anthracene~ not bearlng a functional group useful a~ intermediates are known or ~ay be prepared by method~ known in the art, e.g. the proce~s de~cribed in US Patent Specification
4 255 343~ Friedel Crafts abnd Related Reactions Vol. III by G. Olah, and Houben Weyl, Band VII/Teil 2a page 76 et seq.

~L2~
~- L0 -Functional fllkylation of aptlonally sub~tltllted anthrscene has the advantage that lt i8 a slngle stage proeess for producin~ ompoullds of formulA I which ls conventiently effected at a ta~peratllre ranging from 20 to 170~C, convenlently 20 to 120C. Functional acylation may llkewise ba effscted at similar elevated temperatures.
The reaction is ePfected in the presence of a cataly3t e.g. a Bron~ted acid, an active earth, a metal salt or a metal ~alt in combination wLth a Bronsted acid. Bronsted acids used may be organic or inerganic ~tcid~, or partial ~alts thereof, and may be an lnor-ganic mineral acid e.g. hydrochloric-, sulphuric-, perchloric-or orthophosphoric acid; an alkyl-, haloalkyl-, aryl- or alkaryl-substituted inorganic ac~d e.g. methane, dlfluoromethane, tri-fluoromethane or ethane sulphonic aclds5 benzene sulphonic acidl p-toluena sulphonic acid or methane phosphic acid; or an organic acid e.g. dichloroacetic acld, trichloracetic acid or trifluoro-acetic acid. Active earths used may be those commercially-available under the trade mark Fulmont~ 237 and Fulcat~ 22; while aluminium chloride and zinc chloride and stannic chloride are suitable metal salts.

Dapending on whether one or two functional alkyl or functional acyl groups are being introduced up to one or at lea~t two moles of functional alkylating or functional acylating agent are used per mole of anthracene. When one alkyl-, acyl-, or functional alkyl group is being introduced into a substituted anthracene then up to one mole of ~1kylating agent, acylating agent, or functional alkylating agent is used.

The reaction may be carried out with or without a solvent, of which benzene, chlorobenzene, toluene, xylene, nitromethane and acetic acid are suitabla.

Function11 al~ylating agents whlch may be used contain a reacti~e centre, a.g. an olefinic- or hydroxy group.

Examples of olefinic functlonal alkylating agent~ are:
5-Methylhex-5-enoic acid Methyl-5-methyl~hex-4-enoate Methyl-5-methylhex-S-enoate Ethyl-5-methylhex-5-enoate n-Propyl-5-methylhex-5-en~ate iso-Propyl-5-methylhex-5-enoatQ
n-Butyl-5-methylhex-5-enoate iso-Butyl-S-methylhex 5-enoate sec-Butyl-5-methylhex-5-enoste n-Pentyl-5-methylhex-S-enoate i~o-Pentyl-5-methylhex-5-enoate ~ec-Pentyl-S-methylhex-5-enoate n-Hexyl-5-methylhex-5-enoate Cyclohexyl-5-methylhax-5-enoate 2-Ethylhexyl-5-methylhex-5-enoate n-Octyl-5-methylhex-5-enoate Methyl 5,7,7-trimethyl-oct-4-enoate 1,7-Di-methoxycarbonyl-4-methyl-hept-3-ene 4-Carbomethoxy-l-methylcyclohex-l-ene 4-Acetyl-l-methylcyclo-hex 1-ene Methyl-citronellate Citronellol Citronellyl-acetate Citronellyl-methyl-ether Citronellyl-n-butyl-ether Cltronellyl-nitrila Ethyl-2-ethoxycarbonyl-5-methyl-hex-4-enoate Examples of alkylating agents are isobutylene, diisobutylene, t-butanol, t-butylacetate, 1,1,3,3-tetramethylbutan-1-ol, l-methyl-cyclohex-l-ene, ~-methylstyrene, cumyl alcohol and cumyl acetate.

1;~

Any functlonal clerivative of a compound of formula I may be con-verted to a different unctlonal derlvative. For example when (~
the acid group -C0211 it may be esterlf:Led with an alcohol R20H to give the corre~pondlng ester -C()2R2, or when Q ls the ester group -CO2R2 it may be transesterlfied to give a different R2 group, or alternatively the ester group -CO2R2 may be converted to an amide -CoNR2~.3 by treatment with NHR2 R3, wherein R2 and R3 have their previous significance or may be converted to an alcohol by reduct:Lon of by reaction wlth a Grignard reagent. When the group Q i8 sn alcohol group, it may be esterified with an acylating agent and converted into the group oco~4 in which R~ has its previous signi-ficance.

The compound~3 of formula I are useful as sen~itisers for photo-curable polymer systems of use for protective coatings or photo image production.

The following Examples further illustrate the present invention.
Parts are parts by weight.

Exsmple 1 To a stirred solution of 15.0 parts of aluminium chloride in 50 parts of nitromethane at room temperature are added 8.9 parts of anthracene followed by 14.2 parts of methyl 5-methyl-hex-5-enoate dropwise over 15 mlnutes. On completing the addition stirrlng at room temperature is continued a further 24 hours before the reaction mixture is poured into lSO parts of 2N hydrochloric acid. The organic phase is ether extracted washed wlth water and evaporated.
The resldual oll is then refluxed for 3 hours with 200 parts of methanol which had previously been saturated with hydrogen chloride gas. After ~tripplng down the methanol solution on a rota-evaporator the residual oil is diluted with ether and the ether solution washed with sodium bicarbonate solution, then water, and evaporated.
Distlllation of the residue gives a fractlon bo 7 250-300C con-taining 94 % of 2,6 and 2,7-bis-(5-methoxy-carbonyl-2-methyl-pent-lZ7;~73~

2-yl~-anthrac~ne. Cry~talll~atlon o~ thl~ mer mLxturo from methanol ~ives, a~ a Elrat crop of crystAIs, the 2,6-iDomcr mp 111-3C with the following percentage compo~ltion by wei~ht.

Carbon Hydrogen Found 77.82 8.65 Calculated for C30H3gOI~ 77.89 8.28 The mother llqllorD from the abov~ crystallisatlon are concentrated and then ylPld, a3 a second crop of crystals, the 2,7-l~omer m.p 94-96C having Carbon ~ydrogen Found (C30H3~04) 77 94 8.38 Example 2 8.~ Parts of anthracene, 14.2 parts of methyl 5-methyl-he~-5-enoate, and 26.1 parts of ~tannlc chloride ln 50 parts of p-xylene are heated on steam-bath for 24 hour~. The reaction mixture is then poured into 250 part~ of 2N hydrochlorlc acld and the organic phase extracted with ether. The ether solution after washing with in turn water, sodium bicarbonate solutlon and water is evaporated. The re~idue is treated with 100 parts of ~ethanol and thers is then filte~ed off 3.7 part~ of anthracene. The methanol solution is evaporated under reduced pre~sure to leave a residue whlch distilled to give a fraction bo 7 220C. Crystallisation of this fraction f~om 40-60C petroleum-ether gives 2-(5-methoxycarbonyl-2-methyl-pent-2-yl~-anthracene with m.p 82-4C and the followlng percentage co~position by weight.

Carbon Hydrogen Found 82.59 7.79 Calculated for C22H2 42 82.46 7.5S

~L;2~

E _ 26.1 Par~ of anhydroufl ~tannic chlorlde aro dL~olved ln 100 pArt~
of p-xylene, and to this ~olution i9 added 1.5 part~ t~lEluoro-methane culphonic acid, 14.2 part~ of methyl 5-methyl-hex-5-enoate, and 17.8 parta of anthracene. This mlxture is then heated on a ~team bath for 8 hour~ and then poured into 500 parts of water. The organic pha~e is taken up in ether, the ether solution wafihed wlth water snd evaporated. To the residue 300 psrt~ of methanol are added and brought to reflux before flltering to remove 6.7 psrt~ of in~oluble snthracene. The methanol filtrate, to which is added 1.0 part of p-toluene sulphonic acid~ i8 refluxed for 4 hour3 to e~terify any free acid produced in work up. After removlng the ~ethanol under reduced pressure, the residue is taken up in ether, and the ether solution washed with sodium bicarbonate solution, then water, and evaporated. Distillation of the residue gives as a first ~raction bo 5 210-40C 2-~5-methoxycarbonyl-2-methyl-pent-2-yl)-anthracene m.p 82-4C identical with that obtainad in Example 2.

Continuation of the destillation give~ a second fraction bo 5 240-90C which is a mixture of 2,6 and 2,7-bis-(5-methoxycarbonyl-2-methyl-pent-2-yl)-anthracene. Fractlonal crystall~Qation of thi~
mixture from methanol give~ the 2,6 ~nd 2,7-isomers with m.p 111-3C
and 94-6C respectively which are identical with tho3e obtained in Example 1. The th~ee esters described in thi~ Example, on alkal~ne hydrolysis, give ~helr re~pecitve acid as ~ollwos.

Acid m.p Carbon Hydrogen 2-(5-Carboxy-2-methyl- 149-51C Fo~nd 81.95 7.29 pent~2-yl?-anthracene Calc.C2lH2202 82.32 7.24 2,6-bi~-(5-Carboxy-2-methyl- 263-5~C Found 77.52 7.66 pent-2-yl)~anthracene Calc.C28H3404 77.39 7.89 2,7-bi~(S-Carboxy-2-methyl- 1$9-61C Found 77.40 8.12 pent-2-yl-)anthracene Calc.C28~13404 77.39 7.89 ,. . .

Exampl~ 4 8.9 Parts Oe anthlacene, 18.4 parts o~ methyl cltrollellAte, 13.0 parts of stannic chloride, and 1.5 part~ of trifluoromethane sulphonic acid1 in 50 parts of p-xylene are heated on a ~team-bath for 24 hours. The work-up of Example 1 is followed and gives, on distillation, a fraction bo 3 220-80C containlng 84 % of 2-(7-methoxycarbonyl-2,6-dimethyl-hept-2~yl)-anthracene. The ester i8 obt~ined a~ a white cry~talline solid m.p 41-3C from 40-60 petroleum-ether, following column chromatography on a silica column prspared in 40-60 petroleum-ether eluted with the same.

Carbon Hydrogen Found 82.75 8.17 Calculated for C2sH~ 02 82.83 8.34 Alkaline hydrolysis of this ester gives 2-(7-carboxy-2l6-dimethyl-hept-2-yl)-anthracene m.p 127-9C after crystalllsation from acetic acid and containing a llttle ~ater.

Carbon Hydrogen Found 82.70 7.76 Calculated for C24H2~Oz 82.72 8.10 Continuation of the above di~tillation gives a further fraction bo 6 290-310C which i~ a mixture of 2,6 and 2,7-bis-(7-methoxycarbonyl-2,6-dimethyl-hept-2-yl~-anthracene.

Carbon Hydrogen Fo~nd 79.38 9.19 Calculated for C36HsoO4 79.08 9~22 Example 5 Example 3 i5 rep~ated except that 30.8 parts of 4-methoxycarbonyl-1-methyl-cyclohex-1-ene is used instead of the methyl 5-methyl-S-hax-S-enoate and the reaction period iB 24 hours. Distillation gives a fraction bo 5 200-60C of which 91 % is cis and trans -2-(4-methoxycasbonyl-l-methyl-cyclohsx-l-yl~-anthracene. Trsatment of this di~tillate with a mixture of ~ther and 40-60C petroleum-ether ~Llæ67~

givo~ a ~olld containing almo~t equal proportion~ of the ~i~3 and trans i~omer~ and the~ are then separaterl by fractlonal cry~tallL-~atlon from methAnol. Th~ cls and tran~ omer~ have m.p 178-81C
and 139-42C respectiv01y, and the following percentage compo-sitions:

Carbon Hydrogen Found for cls-iAomer 83.13 7.43 Calculated for trans-l~omer 83.28 7.42 Calculated for C23H2 402 83.10 7.28 The dlstillation i,3 continued and gives a fractioD bo 5 260-350C
whlch is dissol~ed ln ether, concentrated and diluted with 40-60C
petroleum-ether to give a mixture of 296 and 2,7-bi~3-(4-methoxy-carbonyl-l-methyl-cyclohex-l-yl)-aslthracene m.p 176-214C.

Carbon Hydrogen Found 78.83 7.91 Calculated for C3 2~13 a4 78.98 7.87 Exa~ple 6 Into 3.2 parts 2-~5-methoxycarbonyl-2-methyl-pent-2-yl)-anthracene, ; 2.6 parts ~tannic chloride and O.lS parts trifluoromethane sulphonicacid ln 25 parta oE p-xylene at 100C is pas~ed isobutylene ga6 for 1 hour with stirring. The reaction mixture i~ poured into 250 parts of water and the organic phase i~olated with ether. Di~tillation glves a fraction bo 5 190-220C which, aft~r dilution with 40-60C
petrolPum-ether and ~torage at -20C yield~ a mlxture of 2-tert-butyl-6 and 7-(5-methoxycarbonyl-2-methyl-pent-2-yl)-anthracene m.p 81-9C.

Carbon Hydrogen Found 83.27 8.60 Calculated for C26H3202 82.94 8.57 ,~

,:

~1~3~

Example 7 1305 part~ of 2-(5-methoxycarbonyl-2-methyl-pent--2-yl) anthracerle in 100 parts o~ ether are added to a ~olutlon of methyl magn~lum iodide prepared from 3.0 parts magnesium and 18.0 parta of methyl iodide in 150 part~ of ether. On completing the addition the reaction mixture is stirred for 3 hour~ before being treated with dilute hydrochloric acid. The ether phase i~ separated, washed with water, and evaporated to leave 2-(6-hydroxy-2,6-dimethyl-hept-2-yl~-anthracene with m.p 117-8C after crystallisation from 60-80C
petroleum-ether.

Carbon ~ydrogen Found 86.48 8~94 Calculated for C23H2aO 86.20 8.81 Example 8 1.1 part~ of 2-(5-methoxycarbonyl 2-pent-2-yl)-anthracene and 1.0 part~ of lithium aluminium hydride in SO parts of ~odium dried ether sre stirred at room temperature overnight and then treated with dilute hydrochloric acid. The ether phase is ~epa~ated, washed with water, evaporated, and the residue cry3talli~ed from 4~-60C
petroleum-ether containing a little scetone to give 2-(6~hydroxy-2-methyl-hex-2-yl~-anthrscene m.p 123-5C.

Ca~bon ~ydrogen Found 86.31 8.25 Calculated for C21H240 86.26 8.27 Treatment of the alcohol with acetic anhyd~ide give~ 2-(6-acetoxy 2-methyl-hex-2-yl)-anthracene with m.p. 58-9C after cry3tallisation from 40-60C petroleum-ether at O~C.

Carbon Hydrogen Found 82.01 7.84 Calculated for C21H260 82.60 7.84 "

~L;2~73~

~xamplo 9 1.0 part~ of 2-(5-methoxycarbonyl-2-methyl-pent-2-yl) anthracene arld 3.0 psrts of n-butylamine are ~eal~d into a gla3~ vial an~ heated flt 120C for 24 hour~. The exceas amtne i~ evaporated and the re~idue crystalli~ed from ether at 0C to glve 2-(5-N-n-butylcarbamoyl-2-methyl-pent-2-yl)-anthracene m.p 111-3C.

Carbon Hydrogen Nitrogen Found 83.04 8.o6 3.69 Calculated for C25H31N0 83.06 8.64 3.87 Example 10 1.0 Parts of 2.6-bis-(5 methoxycarbonyl-2-methyl-pent-2-yl~-anthracene and 1.0 parts of lithium aluminium hydride in 25 parts of ~odium drled ether are reacted and worked up as described in Exampl~ 3. From the reduction i8 obtained 2,6-bis-(6-hydroxy-2-methyl-hex-2-yl)-anthracene m.p. 174-6C after cry~tallisation from acetone.

Carbon Hydrogen Found 82.62 9.28 Calculated for C28H3~3O2 82.71 9.42 Example 11 0.25 Parts of 2~6 bia-(5-methoxycarbonyl-2-methyl-pent-2-yl)-anthracene and 2.0 parta of n-butylsmine are reacted together and worked up a6 de~cribed in Exa~ple 9.
2,6-Bis-(5-N-n-butylcarbamoyl-2-methyl-p~nt-2~yl?-anthracen2 i8 crystalll~ed fro~ ether and has m.p 153-5C.

Carbon Hydrogen Nitrogen Found 79.05 9.72 4.91 Calculated for C36Hs2NzO2 79.36 9.62 5.14 `` ~ ~ ~ ~ 3 ~ 19 -Application Examples A solution consisting of 10 g of an indu~trial epoxy-cresol novolak ~epoxy content 4.5 eq/kg), 0.25 g (7 x 10 4 mol~ of (~6-toluene) (n5-cyclopentadienyl)iron(II) hexafluorophosphate [prepared according to Bull.Soc.Chim. France, 2572 (1975)], 1.3 x 10 3 mol of 2,6-Bis-(5-methoxycarbonyl-2-methylpent-2-yl)-anthracene and 4 g of 1-acetoxy-2-ethoxyethane i8 applied to a copper-coated epoxy board with a 25 ~ wire doctor. The initlally wet film is dried at 80C (dry film thickness approx. 15 ~). The photo-polymeric board prepared in this way is exposed with a 5000 Watt high-pressure mercury discharge lamp located 50 cm from the sample bench, a 21 step Stoufer ~en3itivity guide being used a~ the pattern (cf.
W.S. DeForest, Photoresist, McGraw-~lll Bood Comp., N.Y., page 109 et 6eq. ) . The exposure time is 10, ~0 a~d 30 seconds snd the exposed board is then hardened for 2 minutes at 110C. It i3 developed in 1-acetoxy-2-ethoxyethane, the unexposed part~ being dissolved~ Thi3 results in a relief image, no.'s 3, 4 and 6 being the last step of which an image i8 formed.

The procedure of Example I is followed using 1.3 x 10 3 mol 2,7-Bis-(5-methoxycarbonyl-2-methylpent-2-yl)-anthracene instead of the 2,6-isomer. Expo~ure time i8 10, 20 and 30 seconds and the lhst steps of which images are formed are no.'s 3, 4 and 6.

Claims (9)

What in claimed is:
1. Compounds having the formula:

(I), wherein p is 1 or 2 and q is 0 or 1 provided that p+q is 1 or 2, each R is independently a residue of formula:

-A-(Q)k (II), wherein Q is a residue -COZR2 wherein Z is O or NR3, and R2 is H, straight or branched chain alkyl having from 1 to 18 carbon atoms, a straight or branched chain alkenyl group having 3 to 18 carbon atoms, a cycloalkyl group having from 3 to 12 carbon atoms or an aralkyl group having 7 to 9 carbon atoms; and when Z is -NR3, R3 is hydrogen or a straight or branched chain alkyl group having from 1 to 18 carbon atoms, or R2 and R3, together with the nitrogen atom to which they are each bonded, may form a 5- or 6-membered heterocyclic ring; or Q is a residue -OX wherein X is R3 or COR4, wherein R3 has its previous significance, and R4 is H, a straight- or branched chain alkyl group having from 1 to 18 carbon atoms, a C3-C18 straight or branched chain alkenyl group or a C3-C12 cycloalkyl group; a residue CN; k is 1 or 2, A is a residue of formula (III), wherein n is an integer from 1-17, k is as defined above, R5 and R6 are the same or different and each is a straight- or branched chain alkyl group having 1 to 5 carbon atoms and, when Q is COOR2 either R5 or R6 is optionally substituted by a COOR2 group the R2 groups being the same or different, provided that when R5 or R6 is sub-stituted by a COOH group (i.e. R2=H), then the compound of formula I
does not contain more than three COOH groups or R5 or R6 may be linked to the residue CnH2n+1-k to form a C6-C12 cycloalkylene residue substituted by the group -(CO2R2)k wherein the R2 groups independently have their previous significance and k has its previous significance; each R1, independently, is a C1-C8 straight- or branched chain alkyl, a C7-C9 aralkyl group, optionally substituted by one or two halogen atoms, an alkyl (C1-C4)-cycloalkyl (C5-C12) group; or R1 is a residue of formula II
as hereinbefore defined, and when R1 is A residue of formula II, then R1 and R may be the same or different; and salts of carboxylic acids of formula I with organic or inorganic bases.
2. Compounds of formula I according to claim 1 wherein p+q = 2.
3. Compounds of formula I according to claim 2 wherein R and R1 are each a residue of formula II as defined in claim 1.
4. Compounds of formula I according to claim 1 wherein p+q = 2 and R
and R1 are the same residue of formula II.
5. Compounds of formula I according to claim 4 wherein the residues R and R1 are bonded in the 2,6- or 2,7-positions of the anthracene molecule.
6. Compounds of formula I according to claim I and having the formula:

(IV), wherein R is a residue of formula II as defined in claim 1, and R1 is a residue of formula II as defined in claim 1 or R1 is a C1-C8 straight- or branched chain alkyl residue; as well as salts thereof.
7. Compounds of formula I according to claim 1 wherein p is 1 and q is O.
8. Compounds of formula I according to claim 1 wherein k is 1.
9. Compounds of formula I according to claim 8 wherein Q is a residue CO2R2 wherein R2 is as defined in claim 1.

FO 7.3/ACK/sm*
CA000488337A 1984-09-07 1985-08-08 Anthracene derivatives Expired - Lifetime CA1272731A (en)

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US4933398A (en) * 1987-07-01 1990-06-12 Ciba-Geigy Corporation Photosensitive epoxy resins and use thereof
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