Claims
- 1. A method for providing a nonlinear optical effect comprising, providing a nonlinear optical element comprising:
- methine or azamethine dye polymers containing as characteristic monomer units radicals of the formulae I, II, III and IV ##STR37## where G is a divalent radical of the formula ##STR38## where the rings B and C can each be benzofused,
- L.sup.1, L.sup.2 and L.sup.3 are each independently of the others hydrogen, methyl, fluorine or chlorine,
- L.sup.4 is fluorine or chlorine,
- L.sup.5 is hydrogen, fluorine, chlorine, bromine, hydroxyl, nitro, C.sub.1 -C.sub.6 -alkyl, cyano, C.sub.1 -C.sub.4 -alkylsulfonylamino, C.sub.1 -C.sub.6 -alkoxycarbonyl, C.sub.1 -C.sub.4 -alkylcarbamoyl or C.sub.2 -C.sub.4 -alkanoylamino,
- L.sup.6 is hydrogen, fluorine, chlorine, cyano, C.sub.1 -C.sub.4 -alkylcarbamoyl, C.sub.2 -C.sub.4 -alkanoylamino, C.sub.1 -C.sub.4 -alkylureido, C.sub.1 -C.sub.4 -alkylsulfamoyl or C.sub.1 -C.sub.6 -alkoxycarbonyl,
- L.sup.7 is a radical of the formula ##STR39## where M.sup.1 is hydrogen, C.sub.1 -C.sub.6 -alkyl, benzyl, cyclohexyl, phenyl or tolyl,
- M.sup.2 is hydrogen, chlorine, C.sub.1 -C.sub.6 -alkyl optionally interrupted by an oxygen atom in ether function, phenyl, C.sub.1 -C.sub.6 -alkoxy, cyano or C.sub.1 -C.sub.6 -alkoxycarbonyl, wherein the alkyl group may be interrupted by one or two oxygen atoms in ether function,
- M.sup.3 is hydrogen, C.sub.1 -C.sub.6 -alkyl, phenyl, cyano, nitro or C.sub.1 -C.sub.6 -alkoxycarbonyl, wherein the alkyl group may be interrupted by one or two oxygen atoms in ether function, or M.sup.2 and M.sup.3 together are a fused benzo ring,
- M.sup.4 is hydrogen, chlorine, cyano, nitro or C.sub.1 -C.sub.6 -alkoxycarbonyl, wherein the alkyl group may be interrupted by one or two oxygen atoms in ether function,
- M.sup.5 is chlorine, C.sub.1 -C.sub.6 -alkyl optionally interrupted by an oxygen atom in ether function, C.sub.1 -C.sub.6 -alkoxy or C.sub.1 -C.sub.6 -alkylthio,
- M.sup.6 is C.sub.1 -C.sub.6 -alkyl, and
- M.sup.7 is hydrogen, chlorine, cyano, thiocyanato, C.sub.1 -C.sub.6 -alkyl optionally interrupted by an oxygen atom in ether function, C.sub.1 -C.sub.6 -alkoxy, C.sub.1 -C.sub.6 -alkylthio, 2-(C.sub.1 -C.sub.2 -alkoxycarbonyl)ethylthio or C.sub.1 -C.sub.6 -alkoxycarbonyl, wherein the alkyl group may be interrupted by one or two oxygen atoms in ether function,
- L.sup.8 is a radical of the formula ##STR40## where M.sup.8 is C.sub.1 -C.sub.6 -alkyl or cyclohexyl,
- M.sup.9 is hydrogen, chlorine, C.sub.1 -C.sub.6 alkyl optionally interrupted by 1 oxygen atom in ether function, C.sub.1 -C.sub.6 -alkoxy or C.sub.1 -C.sub.6 -alkoxycarbonyl, wherein the alkyl group may be interrupted by 1 or 2 oxygen atoms in ether function,
- M.sup.10 is hydrogen, C.sub.1 -C.sub.6 -alkyl, cyano, nitro or C.sub.1 -C.sub.6 -alkoxycarbonyl, wherein the alkyl group may be interrupted by 1 or 2 oxygen atoms in ether function,
- M.sup.11 is hydrogen, chlorine, cyano, nitro or C.sub.1 -C.sub.6 -alkoxycarbonyl, wherein the alkyl group may be interrupted by 1 or 2 oxygen atoms in ether function,
- M.sup.12 is chlorine, C.sub.1 -C.sub.6 -alkyl optionally interrupted by 1 oxygen atom in ether function, C.sub.1 -C.sub.6 -alkoxy or C.sub.1 -C.sub.6 -alkylthio,
- M.sup.13 is C.sub.1 -C.sub.6 -alkyl, and
- M.sup.14 is hydrogen, chlorine, cyano, thiocyanato, C.sub.1 -C.sub.6 -alkyl optionally interrupted by 1 oxygen atom in ether function, C.sub.1 -C.sub.6 -alkoxy, C.sub.1 -C.sub.6 -alkylthio, 2-(C.sub.1 -C.sub.2 -alkoxycarbonyl) ethylthio or C.sub.1 -C.sub.6 -alkoxycarbonyl, wherein the alkyl group may be interrupted by 1 or 2 oxygen atoms in ether function,
- L.sup.9 is hydrogen, fluorine, chlorine, methyl or a radical of the formula
- --NH--CO--B.sup.1, --NH--CO--OB.sup.1, --NH--CO--NB.sup.1 B.sup.2, NH--CS--OB.sup.1,
- --NH--CS--B.sup.1 B.sup.2, --NH--SO.sub.2 --B.sup.1 or --NH--SO.sub.2 --NB.sup.1 B.sup.2,
- where
- B.sup.1 and B.sup.2 are independently of the other C.sub.1 -C.sub.4 -alkyl,
- L.sup.10 is hydrogen, fluorine or chlorine or L.sup.9 and L.sup.10 together are a fused benzo ring,
- L.sup.11 is a radical of the formula
- --CO--OB.sup.1, --CO--NHB.sup.1, --CO--NH--CO--B.sup.1, --NH--CO--B.sup.1,
- --NH--CO--OB.sup.1, --NH--CO--NB.sup.1 B.sup.2, --NH--CS--OB.sup.1, --NH--CS--B.sup.1 B.sup.2,
- --NH--SO.sub.2 --B.sup.1 or --NH--SO.sub.2 --NB.sup.1 B.sup.2,
- where
- B.sup.1 and B.sup.2 are each as defined above,
- L.sup.12 is hydrogen or C.sub.1 -C.sub.4 -alkyl,
- L.sup.13 and L.sup.14 are each independently of the other hydrogen, C.sub.1 -C.sub.12 -alkyl, C.sub.5 -C.sub.7 -cycloalkyl, phenyl, pyridyl, C.sub.1 -C.sub.6 -alkanoyl, C.sub.1 -C.sub.6 -alkoxycarbonyl, C.sub.1 -C.sub.6 -alkylsulfonyl, C.sub.5 -C.sub.7 -cycloalkylsulfonyl, phenylsulfonyl, pyridylsulfonyl, benzoyl, pyridylcarbonyl or thienylcarbonyl, or R.sup.2 and R.sup.3 are combined with the nitrogen atom joining them together into a five- or six-membered saturated heterocyclic radical which optionally contains further hetero atoms,
- L.sup.15 is hydrogen or C.sub.1 -C.sub.6 alkyl,
- L.sup.16 is hydrogen, fluorine, chlorine or bromine,
- L.sup.17 is fluorine, chlorine or bromine,
- L.sup.18 is C.sub.1 -C.sub.12 -alkyl which may be interrupted by from one to three atoms in ether function, phenyl or hydroxyl,
- L.sup.19 is cyano, carbamoyl, carboxy or C.sub.1 -C.sub.6 -alkoxycarbonyl,
- L.sup.20 is C.sub.1 -C.sub.6 -alkyl or C.sub.3 -C.sub.4 -alkenyl and
- W is oxygen or a radical of the formula ##STR41## where L.sup.20 in each case has the abovementioned meanings; Z is nitrogen or CH,
- R.sup.1 and R.sup.2 are each, independently of the other, hydrogen, C.sub.1 -C.sub.6 -alkyl or C.sub.1 -C.sub.6 -alkoxy optionally substituted by phenyl or C.sub.1 -C.sub.4 -alkoxy, is hydrogen, C.sub.1 -C.sub.6 -alkyl, C.sub.5 -C.sub.7 -cycloalkyl or C.sub.3 -C.sub.4 -alkenyl,
- R.sup.4 is hydrogen, deuterium, methyl, trideuterated methyl or chlorine,
- R.sup.5 is hydrogen or deuterium,
- Y.sup.1 and Y.sup.2 are each, independently of the other, C.sub.2 -C.sub.11 -alkylene optionally interrupted by from 1 to 3 oxygen atoms in ether function or imino or C.sub.1 -C.sub.4 -alkylimino groups,
- E is oxygen, imino or C.sub.1 -C.sub.4 -alkylimino, and
- X is hydroxyl, C.sub.1 -C.sub.6 -alkoxy, trideuterated methoxy, 2,3-epoxypropoxy, phenoxy, amino or C.sub.1 -C.sub.4 -mono- or -dialkylamino, and
- the ring A can be benzofused, the proportion of monomer units of the formula I being from 1 to 100 mol %, the proportion of monomer units of the formula II being from 0 to 99 mol %, the proportion of monomer units of the formula III being from 0 to 99 mol % and the proportion of monomer units of the formula IV being from 0 to 75 mol %, each percentage being based on the polymer, and the average molecular weight of the polymer being from 1,000 to 100,000, and
- contacting said nonlinear optical element with light.
- 2. A method for preparing methine or azamethine dye polymers, comprising reacting one or more monomers wherein said one or more monomers are selected to provide a polymer containing as characteristic monomer units radicals of the formulae I, II, III and IV ##STR42## where G is a divalent radical of the formula ##STR43## where the rings B and C can each be benzofused,
- L.sup.1, L.sup.2 and L.sup.3 are each independently of the others hydrogen, methyl, fluorine or chlorine,
- L.sup.4 is fluorine or chlorine, is hydrogen, fluorine, chlorine, bromine, hydroxyl, nitro, C.sub.1 -C.sub.6 -alkyl, cyano, C.sub.1 -C.sub.4 -alkylsulfonylamino, C.sub.1 -C.sub.6 -alkoxycarbonyl, C.sub.1 -C.sub.4 -alkylcarbamoyl or C.sub.2 -C.sub.4 -alkanoylamino, L.sup.6 is hydrogen, fluorine, chlorine, cyano, C.sub.1 -C.sub.4 -alkylcarbamoyl, C.sub.2 -C.sub.4 -alkanoylamino, C.sub.1 -C.sub.4 -alkylureido, C.sub.1 -C.sub.4 -alkylsulfamoyl or C.sub.1 -C.sub.6 -alkoxycarbonyl,
- L.sup.7 is a radical of the formula ##STR44## where M.sup.1 is hydrogen, C.sub.1 -C.sub.6 -alkyl, benzyl, cyclohexyl, phenyl or tolyl,
- M.sup.2 is hydrogen, chlorine, C.sub.1 -C.sub.6 -alkyl optionally interrupted by an oxygen atom in ether function, phenyl, C.sub.1 -C.sub.6 -alkoxy, cyano or C.sub.1 -C.sub.6 -alkoxycarbonyl, wherein the alkyl group may be interrupted by one or two oxygen atoms in ether function,
- M.sup.3 is hydrogen C.sub.1 -C.sub.6 -alkyl, phenyl, cyano, nitro or C.sub.1 -C.sub.6 -alkoxycarbonyl, wherein the alkyl group may be interrupted by one or two oxygen atoms in ether function, or M.sup.2 and M.sup.3 together are a fused benzo ring,
- M.sup.4 is hydrogen, chlorine, cyano, nitro or C.sup.1 -C.sub.6 -alkoxycarbonyl, wherein the alkyl group may be interrupted by one or two oxygen atoms in ether function,
- M.sup.5 is chlorine, C.sub.1 -C.sub.6 -alkyl optionally interrupted by an oxygen atom in ether function, C.sub.1 -C.sub.6 -alkoxy or C.sub.1 -C.sub.6 -alkylthio,
- M.sup.6 is C.sub.1 -C.sub.6 -alkyl, and
- M.sup.7 is hydrogen, chlorine, cyano, thiocyanato, C.sub.1 -C.sub.6 -alkyl optionally interrupted by an oxygen atom in ether function, C.sub.1 -C.sub.6 -alkoxy, C.sub.1 -C.sub.6 -alkylthio, 2-(C.sub.1 -C.sub.2 -alkoxycarbonyl)ethylthio or C.sub.1 -C.sub.6 -alkoxycarbonyl, wherein the alkyl group may be interrupted by one or two oxygen atoms in ether function,
- L.sup.8 is a radical of the formula ##STR45## where M.sup.8 is C.sub.1 -C.sub.6 -alkyl or cyclohexyl,
- M.sup.9 is hydrogen, chlorine, C.sub.1 -C.sub.6 -alkyl optionally interrupted by 1 oxygen atom in ether function, C.sub.1 -C.sub.6 -alkoxy or C.sub.1 -C.sub.6 -alkoxycarbonyl, wherein the alkyl group may be interrupted by 1 or 2 oxygen atoms in ether function,
- M.sup.10 is hydrogen, C.sub.1 -C.sub.6 -alkyl, cyano, nitro or C.sub.1 -C.sub.6 -alkoxycarbonyl, wherein the alkyl group may be interrupted by 1 or 2 oxygen atoms in ether function,
- M.sup.11 is hydrogen, chlorine, cyano, nitro or C.sub.1 -C.sub.6 -alkoxycarbonyl, wherein the alkyl group may be interrupted by 1 or 2 oxygen atoms in ether function,
- M.sup.12 is chlorine, C.sub.1 -C.sub.6 -alkyl optionally interrupted by 1 oxygen atom in ether function, C.sub.1 -C.sub.6 -alkoxy or C.sub.1 -C.sub.6 -alkylthio,
- M.sup.13 is C.sub.1 -C.sub.6 -alkyl, and
- M.sup.14 is hydrogen, chlorine, cyano, thiocyanato, C.sub.1 -C.sub.6 -alkyl optionally interrupted by 1 oxygen atom in ether function, C.sub.1 -C.sub.6 -alkoxy, C.sub.1 -C.sub.6 -alkylthio, 2-(C.sub.1 -C.sub.2 -alkoxycarbonyl) ethylthio or C.sub.1 -C.sub.6 -alkoxycarbonyl, wherein the alkyl group may be interrupted by 1 or 2 oxygen atoms in ether function,
- L.sup.9 is hydrogen, fluorine, chlorine, methyl or a radical of the formula
- --NH--CO--B.sup.1, --NH--CO--OB.sup.1, --NH--CO--NB.sup.1 B.sup.2, NH--CS--OB.sup.1,
- --NH--CS--B.sup.1 B.sup.2, --NH--SO.sub.2 --B.sup.1 or --NH--SO.sub.2 --NB.sup.1 B.sup.2,
- where
- B.sup.1 and B.sup.2 are independently of the other C.sub.1 -C.sub.4 -alkyl,
- L.sup.10 is hydrogen, fluorine or chlorine or L.sup.9 and L.sup.10 together are a fused benzo ring,
- L.sup.11 is a radical of the formula
- --CO--OB.sup.1, --CO--NHB.sup.1, --CO--NH--CO--B.sup.1, --NH--CO--B.sup.1,
- --NH--CO--OB.sup.1, --NH--CO--NB.sup.1 B.sup.2, --NH--CS--OB.sup.1, --NH--CS--B.sup.1 B.sup.2,
- --NH--SO.sub.2 --B.sup.1 or --NH--SO.sub.2 --NB.sup.1 B.sup.2,
- where
- B.sup.1 and B.sup.2 are each as defined above,
- L.sup.12 is hydrogen or C.sub.1 -C.sub.4 -alkyl,
- L.sup.13 and L.sup.14 are each independently of the other hydrogen, C.sub.1 -C.sub.12 -alkyl, C.sub.5 -C.sub.7 -cycloalkyl, phenyl, pyridyl, C.sub.1 -C.sub.6 -alkanoyl C.sub.1 -C.sub.6 -alkoxycarbonyl, C.sub.1 -C.sub.6 -alkylsulfonyl, C.sub.5 -C.sub.7 -cycloalkylsulfonyl, phenylsulfonyl, pyridylsulfonyl, benzoyl, pyridylcarbonyl or thienylcarbonyl, or R.sup.2 and R.sup.3 are combined with the nitrogen atom joining them together into a five- or six-membered saturated heterocyclic radical which optionally contains further hetero atoms,
- L.sup.15 is hydrogen or C.sub.1 -C.sub.6 -alkyl,
- L.sup.16 is hydrogen, fluorine, chlorine or bromine,
- L.sup.17 is fluorine, chlorine or bromine,
- L.sup.18 is C.sub.1 -C.sub.12 -alkyl which may be interrupted by from one to three atoms in ether function, phenyl or hydroxyl,
- L.sup.19 is cyano, carbamoyl, carboxy or C.sub.1 -C.sub.6 -alkoxycarbonyl,
- L.sub.20 is C.sub.1 -C.sub.6 -alkyl or C.sub.3 -C.sub.4 -alkenyl and
- W is oxygen or a radical of the formula ##STR46## where L.sub.20 in each case has the abovementioned meanings Z is nitrogen or CH,
- R.sup.1 and R.sup.2 are each, independently of the other, hydrogen, C.sub.1 -C.sub.6 -alkyl or C.sub.1 -C.sub.6 -alkoxy optionally substituted by phenyl or C.sub.1 -C.sub.4 -alkoxy,
- R.sup.3 is hydrogen, C.sub.1 -C.sub.6 -alkyl, C.sub.5 -C.sub.7 -cycloalkyl or C.sub.3 -C.sub.4 -alkenyl,
- R.sup.4 is hydrogen, deuterium, methyl, trideuterated methyl or chlorine,.
- R.sup.5 is hydrogen or deuterium,
- Y.sup.1 and Y.sup.2 are each, independently of the other, C.sub.2 -C.sub.11 -alkylene optionally interrupted by from 1 to 3 oxygen atoms in ether function or imino or C.sub.1 -C.sub.4 -alkylimino groups,
- E is oxygen, imino or C.sub.1 -C.sub.4 -alkylimino, and
- X is hydroxyl, C.sub.1 -C.sub.6 -alkoxy, trideuterated methoxy, 2,3-epoxypropoxy, phenoxy, amino or C.sub.1 -C.sub.4 -mono- or -dialkylamino, and
- the ring A can be benzofused, such that the proportion of monomer units of the formula I is from 1 to 100 mol %, the proportion of monomer units of the formula II is from 0 to 99 mol %, the proportion of monomer units of the formula III is from 0 to 99 mol % and the proportion of monomer units of the formula IV is from 0 to 75 mol %, each percentage being based on the polymer formed, and the polymer having an average molecular weight of from 1,000 to 100,000.
Priority Claims (1)
Number |
Date |
Country |
Kind |
42 18 359.6 |
Jun 1992 |
DEX |
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Parent Case Info
This is a division, of application Ser. No. 08/065,905, filed on May 25, 1993.
US Referenced Citations (2)
Number |
Name |
Date |
Kind |
4619990 |
Elmasry |
Oct 1986 |
|
5264507 |
Wiesenfeldt et al. |
Nov 1993 |
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Divisions (1)
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Number |
Date |
Country |
Parent |
65905 |
May 1993 |
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