Alkylenedioxythiophenes and poly(alkylenedioxythiophene)s having urethane-containing side groups
View Patent ↗The present invention relates to alkylenedioxythiophenes of the formula I having urethane-containing side groups: to their preparation and to their oligo- and polymeric derivatives (oligo- and poly(alkylenedioxythiophene)s).
1. Compounds of the formula I:
characterized in that
A is a C 1 -C 5 -alkylene radical which is optionally substituted at any desired point via a linker L by a urethane group and optionally bears further substituents,
L is a methylene group,
x is 0 or an integer of 1 or greater,
n is an integer from 1 to 4 and
R is an n-valent linear or branched, optionally substituted, aliphatic C 1 -C 22 radical, an n-valent, optionally substituted, cycloaliphatic C 3 -C 12 radical or an n-valent, optionally substituted, aromatic C 6 -C 14 radical,
where, in the case that n is greater than 1, A and x is optionally each independently defined identically or differently.
2. Compounds of the formula I according to claim 1 , characterized in that x is 0 or an integer from 1 to 6.
3. Compounds of the formula I according to claim 1 :
characterized in that
A is a C 1 -C 5 -alkylene radical which is optionally substituted at any desired point via a linker L by a urethane group and optionally bears further substituents,
L is a methylene group,
x is 0 or 1,
n is an integer from 1 to 4 and
R is an n-valent linear or branched, optionally substituted, aliphatic C 1 -C 22 radical, an n-valent, optionally substituted, cycloaliphatic C 3 -C 12 radical or an n-valent, optionally substituted, aromatic C 6 -C 14 radical,
where, in the case that n is greater than 1, A and x is optionally each independently defined identically or differently.
4. Compounds of the formula II according to claim 1 :
characterized in that
R is an n-valent linear or branched, optionally substituted, aliphatic
C 2 -C 22 radical, an n-valent, optionally substituted, cycloaliphatic
C 5 -C 12 radical or an n-valent, optionally substituted, aromatic C 6 -C 14 radical,
r and s are each independently integers from 0 to 4, with the proviso that r+s=n and
n is an integer from 1 to 4.
5. Compounds according to at claim 1 , characterized in that R is a linear, optionally substituted C 6 -C 12 -alkylene radical or an optionally substituted C 6 -C 10 -cycloalkylene radical, and r and s are each independently integers from 0 to 2 and n=r+s=2.
6. Compounds according to claim 1 of the formulae III and/or IV:
characterized in that
R is a linear or branched, optionally substituted, C 1 -C 22 -alkyl radical, an optionally substituted, C 3 -C 12 -cycloalkyl radical or an optionally substituted, C 6 -C 14 -aryl radical.
7. Compounds according to claim 1 , characterized in that R is a linear C 1 -C 12 -alkyl radical or a C 6 -C 10 -cycloalkyl radical.
8. Compounds according to claim 1 , characterized in that R is a linear C 4 -C 10 -alkyl radical.
9. Process for preparing compounds of the formulae I to IV, comprising reacting hydroxyl compounds of the formula V:
where
A, x and L are each as defined in claim 1 with monoisocyanates, diisocyanates, higher-functionality isocyanates, or mixtures thereof, represented as:
R(NCO) n ,
where
R and n are each as defined in claims 1 to 8 .
10. Process for preparing oligo- and poly(alkylenedioxythiophene)s having urethane-containing side groups, comprising polymerizing compounds of the formulae I to IV.
11. Oligo- and poly(alkylenedioxythiophene)s having urethane-containing side groups, characterized in that they are obtainable by polymerizing at least one compound according to claim 1 .
12. Oligo- and poly(alkylenedioxythiophene)s having urethane-containing side groups according to claim 11 , characterized in that they contain repeating units of the formulae VIa and/or VIb:
where
R is as defined in at least one of claims 1 to 8 and the number of repeating units VIa and/or VIb is at least 2.
13. Oligo- and poly(alkylenedioxythiophene)s having urethane-containing side groups according to claim 11 , characterized in that the number of units of the formula VIa and the number of units of the formula VIb are each independently 0 to 1000, with the proviso that the sum of the number of repeating units of the formulae VIa and/or VIb in the oligo- or poly(alkylenedioxythiophene) is at least 2 and at most 2000.
14. Oligo- and poly(alkylenedioxythiophene)s having urethane-containing side groups according to claim 11 , characterized in that the number of units of the formula VIa is 1 to 50 and, independently thereof, the number of units of the formula VIb is 0 to 30, with the proviso that the sum of the number of repeating units of the formulae VIa and/or VIb in the oligo- or poly(alkylenedioxythiophene) is at least 3 and at most 50.
15. Oligo- and poly(alkylenedioxythiophene)s having urethane-containing side groups according to claim 11 , characterized in that they carry positive charges.
16. Two- or three-dimensionally crosslinked neutral or cationic oligo- and poly(alkylenedioxythiophene)s having urethane-containing side groups, characterized in that they are obtainable by oxidative polymerization of the compounds according to claim 1 .
17. A method of preparing an electrical component comprising providing as constituent thereof the oligo- and poly(alkylenedioxythiophene)s according to claim 11 .
18. Hydroxyl compounds of the formula V or mixtures of hydroxyl compounds of the formula V:
where
A is a C 1 -C 5 -alkylene radical which is optionally substituted at any desired point via a linker L by a hydroxyl group and optionally bears further substituents,
L is a methylene group and
x is an integer greater than 1.
19. Hydroxyl compounds of the formula V or mixtures of hydroxyl compounds of the formula V according to claim 18 , where x is an integer from 2 to 6.