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US 11,186,545 B2Granted
Phenalene-1-one-containing photosensitizer composition, phenalene-1-one compound and the use thereof
AssigneeTrioptotec GmbH
InventorsAndreas Späth, Anja Eichner
Life of this patent
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Abstract
A phenalene-1-one compound, a photosensitizer composition including the phenalene-1-one compound, an article including the phenalene-1-one compound and/or photosensitizer composition and the use thereof.
Claims21
A photosensitizer composition comprising
- (a) at least one phenalen-1-one compound with the general formula (1):
- wherein the residues R1 to R8, which respectively independently of one another may be identical to or different from each other, respectively represent hydrogen, halogen, alkyl containing 1 to 12 C atoms, alkylaryl containing 5 to 20 C atoms, aryl containing 5 to 20 C atoms, *—O-alkyl containing 1 to 12 C atoms, *—O-alkylaryl containing 5 to 20 C atoms, *—O-aryl containing 5 to 20 C atoms, ether containing 2 to 12 C atoms, a residue with the formula *—O—C(═O)—R(Ia), a residue with the formula *—C(═O)—R(Ib), or an organic residue W1 which contains at least one reactive functional group, with the proviso that at least one of the residues R1 to R7 is an organic residue W1, wherein the organic residue W1 respectively independently of each other represents a residue with the general formula (2) to (6):
- *—[(C(D)(E))d—B]a—(C(D)(E))m—X (2)
- *-A—[(C(D)(E))d—B]c—(C(D)(E))m—X (3)
- *—(C(D)(E))d-AR—(C(D)(E))n—X (4)
- *—[(C(D)(E))d—B]b—(C(D)(E))g-AR—(C(D)(E))n—X (5)
- *-A—[(C(D)(E))d—B]f—(C(D)(E))g-AR—(C(D)(E))n—X (6)
- wherein A respectively independently of each other represents oxygen, sulphur or a residue with the general formula (10a) to (11a):
- wherein *ph respectively denotes a linkage from the residue with the general formula (10a) to (11a) to a C atom of the phenalene ring and *c respectively denotes a linkage from the residue with the general formula (10a) to (11a) to a C atom of the residue (C(D)(E)), and wherein the residue B respectively independently of each other represents oxygen, sulphur or a residue with the general formula (10) to (14):
- wherein the residues R(Ia), R(Ib), R(11a), R(12a), R(13a), R(14a), and R(14b), respectively independently of each other, represent hydrogen, methyl, ethyl, n-propyl, iso-propyl, n-butyl, sec-butyl, iso-butyl, n-pentyl, phenyl or benzyl, and wherein phenyl and benzyl respectively independently of each other may be unsubstituted or substituted with one or more residues selected from the group which consists of halogen, amino, hydroxyl, *—O-alkyl which may be linear or branched, containing 1 to 3 carbon atoms, alkyl which may be linear or branched, containing 1 to 3 carbon atoms, hydroxyalkyl which may be linear or branched, containing 1 to 3 carbon atoms and 1 to 3 OH groups, halogenoalkyl which may be linear or branched, containing 1 to 3 carbon atoms and 1 to 3 halogen groups, and combinations thereof, wherein Y− is an anion which respectively independently of each other represents fluoride, chloride, bromide, iodide, sulphate, hydrogen sulphate, phosphate, hydrogen phosphate, dihydrogen phosphate, at least one carboxylate anion of a carboxylic acid containing 1 to 15 carbon atoms, at least one sulphonate anion of a sulphonic acid containing 1 to 12 C atoms, or a combination thereof, and
- wherein the residues D and E respectively independently of each other represent hydrogen, halogen, hydroxyl, alkyl which may be linear or branched, containing 1 to 5 carbon atoms, hydroxyalkyl which may be linear or branched, containing 1 to 5 carbon atoms and 1 to 5 OH groups, phenyl, benzyl, a residue with the formula *-L—R (II), a residue with the formula *-L—C(=L)-R(III), a residue with the formula *—(CH2)q—X, a residue with the formula *-L—(CH2)q—X, or a residue with the formula *—(CH2)s-L—(CH2)t—X, wherein the residue L respectively independently of each other represents oxygen or sulphur, wherein the residues R(II) and R(III) respectively independently of each other, represent hydrogen, methyl, ethyl, n-propyl, iso-propyl, n-butyl, sec-butyl, iso-butyl, n-pentyl, phenyl or benzyl, and wherein phenyl and benzyl respectively independently of each other may be unsubstituted or substituted, the indices q, s and t respectively independently of each other representing a whole number from 1 to 5,
- wherein the indices a, c, f, g and n respectively independently of each other represent a whole number from 0 to 5,
- and wherein the indices b, d and m respectively independently of each other represent a whole number from 1 to 5,
- wherein the residue Ar respectively independently of each other represents a substituted or unsubstituted aromatic residue or a substituted or unsubstituted heteroaromatic residue, and
- wherein the residue X respectively independently of each other is a reactive functional group denoted by *—N(R(VI))(R(VII)), *—OH, *—SH, *—NCO, *—NCS, *—Si(R(VIII))(R(IX))—[O—Si(R(X))(R(XI))]p—Z, or a residue with the general formula (20) to (24):
- wherein the residues R(20a), R(20b), R(20c), R(21a), R(22a), R(22b), R(22c), R(23a), R(24a), R(24b), and R(24c) respectively of each other, represent hydrogen, methyl, ethyl, n-propyl, iso-propyl, n-butyl, sec-butyl, iso-butyl, or n-pentyl, and wherein the indices l and k respectively independently of each other represent a whole number from 0 to 4,
- wherein the residues R(VI) and R(VII) respectively independently of each other represent hydrogen, alkyl which may be linear or branched, containing 1 to 5 carbon atoms, phenyl or benzyl, wherein phenyl and benzyl respectively independently of each other may be unsubstituted or substituted with one or more residues selected from the group consisting of chlorine, bromine, fluorine, methyl, ethyl, n-propyl, iso-propyl, methoxy, ethoxy, and combinations thereof,
- wherein the residues R(VIII), R(IX), R(X) and R(XI) respectively independently of each other represent hydrogen, alkyl which may be linear or branched, containing 1 to 5 carbon atoms, *—O-alkyl which may be linear or branched, containing 1 to 5 carbon atoms, phenyl or benzyl, wherein phenyl and benzyl respectively independently of each other may be unsubstituted or substituted with one or more residues selected from the group consisting of chlorine, bromine, fluorine, methyl, ethyl, n-propyl, iso-propyl, methoxy, ethoxy, and combinations thereof, wherein the residue Z respectively independently of each other represents halogen, hydroxyl, alkoxyl containing 1 to 4 carbon atoms or alkylcarboxyl containing 1 to 4 carbon atoms, and wherein the index p respectively independently of each other represents a whole number from 0 to 4, and
- (b) at least one polymeric component and/or precursor thereof, wherein the at least one polymeric component and/or precursor thereof is selected from the group which consists of polymers and/or copolymers of acrylic acid and esters thereof, methacrylic acid and esters thereof, cyanoacrylic acid and esters thereof, acrylamide, methacrylamide, styrene, siloxanes and esters thereof, melamine, acrylonitrile, 1,3-butadiene, epichlorohydrin, polyols, polyisoprenes, polyethers, polyetherimides, polyvinyl acetates, polycarbonates, polyether sulphones, carboxymethyl cellulose, alginate, and combinations thereof.
16 more elements
A photosensitizer composition comprising
- (a) at least one phenalen-1-one compound with the general formula (1):
- wherein the residues R1 to R8, which respectively independently of one another may be identical to or different from each other, respectively represent hydrogen, halogen, alkyl containing 1 to 12 C atoms, alkylaryl containing 5 to 20 C atoms, aryl containing 5 to 20 C atoms, *—O-alkyl containing 1 to 12 C atoms, *—O-alkylaryl containing 5 to 20 C atoms, **—O-aryl containing 5 to 20 C atoms, ether containing 2 to 12 C atoms, a residue with the formula *—O—C(═O)—R(Ia), a residue with the formula *—C(═O)—R(Ib), or an organic residue W1 which contains at least one functional group, with the proviso that at least one of the residues R1 to R7 is an organic residue W1, wherein the organic residue W1 respectively independently of each other represents a residue with the general formula (2) to (6):
- *—[(C(D)(E))d—B]a—(C(D)(E))m—X (2)
- *-A—[(C(D)(E))d—B]c—(C(D)(E))m—X (3)
- *—(C(D)(E))d-AR—(C(D)(E))n—X (4)
- *—[(C(D)(E))d—B]b—(C(D)(E))g-AR—(C(D)(E))n—X (5)
- *-A—[(C(D)(E))d—B]f—(C(D)(E))g-AR—(C(D)(E))n—X (6)
- wherein A respectively independently of each other represents oxygen, sulphur or a residue with the general formula (10a) to (11a):
- wherein *ph respectively denotes a linkage from the residue with the general formula (10a) to (11a) to a C atom of the phenalene ring and *c respectively denotes a linkage from the residue with the general formula (10a) to (11a) to a C atom of the residue (C(D)(E)), and wherein the residue B respectively independently of each other represents oxygen, sulphur or a residue with the general formula (10) to (14):
- wherein the residues R(Ia), R(Ib), R(11a), R(12a), R(13a), R(14a), and R(14b), respectively independently of each other, represent hydrogen, methyl, ethyl, n-propyl, iso-propyl, n-butyl, sec-butyl, iso-butyl, n-pentyl, phenyl or benzyl, and wherein phenyl and benzyl respectively independently of each other may be unsubstituted or substituted with one or more residues selected from the group which consists of halogen, amino, hydroxyl, *—O-alkyl which may be linear or branched, containing 1 to 3 carbon atoms, alkyl which may be linear or branched, containing 1 to 3 carbon atoms, hydroxyalkyl which may be linear or branched, containing 1 to 3 carbon atoms and 1 to 3 OH groups, halogenoalkyl which may be linear or branched, containing 1 to 3 carbon atoms and 1 to 3 halogen groups, and combinations thereof, wherein Y− is an anion which respectively independently of each other represents fluoride, chloride, bromide, iodide, sulphate, hydrogen sulphate, phosphate, hydrogen phosphate, dihydrogen phosphate, at least one carboxylate anion of a carboxylic acid containing 1 to 15 carbon atoms, at least one sulphonate anion of a sulphonic acid containing 1 to 12 C atoms, or a combination thereof, and
- wherein the residues D and E respectively independently of each other represent hydrogen, halogen, hydroxyl, alkyl which may be linear or branched, containing 1 to 5 carbon atoms, hydroxyalkyl which may be linear or branched, containing 1 to 5 carbon atoms and 1 to 5 OH groups, phenyl, benzyl, a residue with the formula *-L—R (II), a residue with the formula *-L—C(=L)-R(III), a residue with the formula *—(CH2)q—X, a residue with the formula *-L—(CH2)q—X, or a residue with the formula *—(CH2)s-L—(CH2)t—X, wherein the residue L respectively independently of each other represents oxygen or sulphur, wherein the residues R(II) and R(III) respectively independently of each other, represent hydrogen, methyl, ethyl, n-propyl, iso-propyl, n-butyl, sec-butyl, iso-butyl, n-pentyl, phenyl or benzyl, and wherein phenyl and benzyl respectively independently of each other may be unsubstituted or substituted, the indices q, s and t respectively independently of each other representing a whole number from 1 to 5,
- wherein the indices a, c, f, g and n respectively independently of each other represent a whole number from 0 to 5,
- and wherein the indices b, d and m respectively independently of each other represent a whole number from 1 to 5,
- wherein the residue Ar respectively independently of each other represents a substituted or unsubstituted aromatic residue or a substituted or unsubstituted heteroaromatic residue, and
- wherein the residue X respectively independently of each other is a functional group denoted by *—N(R(VI))(R(VII)), *—OH, *—SH, *—NCO, *—NCS, *—Si(R(VIII))(R(IX))—[O—Si(R(X))(R(XI))]p—Z, or a residue with the general formula (20) to (24):
- wherein the residues R(20a), R(20b), R(20c), R(21a), R(22a), R(22b), R(22c), R(23a), R(24a), R(24b), and R(24c) respectively independent of each other, represent hydrogen, methyl, ethyl, n-propyl, iso-propyl, n-butyl, sec-butyl, iso-butyl, or n-pentyl, and wherein the indices l and k respectively independently of each other represent a whole number from 0 to 4,
- wherein the residues R(VI) and R(VII) respectively independently of each other represent hydrogen, alkyl which may be linear or branched, containing 1 to 5 carbon atoms, phenyl or benzyl, wherein phenyl and benzyl respectively independently of each other may be unsubstituted or substituted with one or more residues selected from the group consisting of chlorine, bromine, fluorine, methyl, ethyl, n-propyl, iso-propyl, methoxy, ethoxy, and combinations thereof,
- wherein the residues R(VIII), R(IX), R(X) and R(XI) respectively independently of each other represent hydrogen, alkyl which may be linear or branched, containing 1 to 5 carbon atoms, *—O-alkyl which may be linear or branched, containing 1 to 5 carbon atoms, phenyl or benzyl, wherein phenyl and benzyl respectively independently of each other may be unsubstituted or substituted with one or more residues selected from the group consisting of chlorine, bromine, fluorine, methyl, ethyl, n-propyl, iso-propyl, methoxy, ethoxy, and combinations thereof, wherein the residue Z respectively independently of each other represents halogen, hydroxyl, alkoxyl containing 1 to 4 carbon atoms or alkylcarboxyl containing 1 to 4 carbon atoms, and wherein the index p respectively independently of each other represents a whole number from 0 to 4, and
- (b) at least one polymeric component and/or precursor thereof, wherein the at least one polymeric component and/or precursor thereof is selected from the group which consists of polymers and/or copolymers of acrylic acid and esters thereof, methacrylic acid and esters thereof, cyanoacrylic acid and esters thereof, acrylamide, methacrylamide, styrene, siloxanes and esters thereof, melamine, acrylonitrile, 1,3-butadiene, epichlorohydrin, polyols, polyisoprenes, polyethers, polyetherimides, polyvinyl acetates, polycarbonates, polyether sulphones, carboxymethyl cellulose, alginate, and combinations thereof,
- wherein the at least one phenalen-1-one compound with the general formula (1) is covalently bonded to the at least one polymeric component and/or precursor thereof.
17 more elements
Dependencies are inferred from the claim text.