Method for producing triarylorganoborates

Patent metadata

Field	Value
Publication number	US-12043636-B2
Application number	US-202016950901-A
Country	US
Kind code	B2
Filing date	Nov 17, 2020
Priority date	Nov 9, 2016
Publication date	Jul 23, 2024
Grant date	Jul 23, 2024

Abstract

The invention relates to a process for preparing triaryl organo borates proceeding from organoboronic esters in the presence of an n-valent cation 1/n K n+ , comprising the anhydrous workup of the reaction mixture and the use of the triaryl organoborates obtained as co-initiator in photopolymer formulations, holographic media and holograms.

First claim

The invention claimed is:

1. Compounds of the formula (C)

in which
R 101 is an optionally branched C 14 - to C 22 -alkyl radical or is additionally defined as R 102 , with the proviso that T 101 and R 131 together and T 102 and R 132 together each contain at least 12 carbon atoms,
R 102 is a radical of the formulae

T 101 is a bridge having 2 to 16 carbon atoms, of which not more than one third may be replaced by O and/or NR 200 and which may be arranged in the form of an optionally branched chain and/or a five- or six-membered ring,
R 131 is an optionally branched and/or optionally substituted C 4 - to C 22 -alkyl radical, an optionally branched and/or optionally substituted C 4 - to C 22 -alkenyl radical, a cyclopentyl, cyclohexyl or cycloheptyl radical, a C 7 - to C 10 -aralkyl radical, a phenyl radical or heterocyclic radical optionally substituted by nonionic radicals, an optionally branched and/or optionally substituted C 4 - to C 22 -alkoxy radical, a cyclopentoxy, cyclohexoxy or cycloheptoxy radical, a C 7 - to C 10 -aralkoxy radical, a phenoxy radical or heteroaryloxy radical optionally substituted by nonionic radicals, an optionally branched and/or optionally substituted C 4 - to C 22 -alkylamino radical, a cyclopentylamino, cyclohexylamino or cycloheptylamino radical, a C 7 -to C 10 -aralkylamino radical, a phenylamino radical or heteroarylamino radical optionally substituted by nonionic radicals,
T 102 is a bridge having 1 to 16 carbon atoms which may be arranged in the form of an optionally branched chain and/or a five- or six-membered ring,
R 132 is an optionally branched and/or optionally substituted C 1 - to C 22 -alkyl radical, a cyclopentyl, cyclohexyl or cycloheptyl radical, a C 7 - to C 10 -aralkyl radical, a phenyl radical or heterocyclic radical optionally substituted by nonionic radicals,
A is NR 201 or oxygen,
R 200 and R 201 are independently hydrogen or C 1 - to C 4 -alkyl,
R 103 and R 104 are independently an optionally branched and/or optionally substituted C 1 -to C 5 -alkyl radical,
or
R 102 is a radical of the formulae

T 101 , R 131 , T 102 , R 132 , R 200 , R 201 and A have the definition given above, with the proviso that T 101 and R 131 together and T 102 and R 132 together each contain at least 12 carbon atoms,
R 101 , R 103 and R 104 together with the N + atom form an imidazole or pyridine ring substituted at least by one radical selected from C 1 - to C 8 -alkyl, C 1 - to C 8 -alkoxy, C 5 - to C 7 -cycloalkyl, benzyl or phenyl,
or
R 101 is an optionally branched C 14 - to C 22 -alkyl radical or is additionally defined as R 102 , with the proviso that T 101 and R 131 together and T 102 and R 132 together each contain at least 12 carbon atoms,
R 102 is a radical of the formulae

and
T 101 , R 131 , T 102 , R 132 , R 200 , R 201 and A have the definition given above,
R 103 and R 104 together form a —(CH 2 ) 4 —, —(CH 2 ) 5 — or —(CH 2 ) 2 —O—(CH 2 ) 2 — bridge, and
R 1 is an optionally hydroxyl- and/or alkoxy- and/or acyloxy- and/or halogen-substituted C 1 - to C 22 -alkyl, C 3 - to C 22 -alkenyl, C 3 - to C 22 -alkynyl, C 5 - to C 7 -cycloalkyl or C 7 -to C 13 -aralkyl radical and
R 4 is a C 6 - to C 10 -aryl radical optionally substituted by at least one radical selected from halogen, C 1 - to C 4 -alkyl, trifluoromethyl, C 1 - to C 4 -alkoxy, trifluoromethoxy, phenyl and phenoxy.

2. The compounds of claim 1 , wherein
R 101 is an optionally branched C 14 - to C 22 -alkyl radical or is additionally defined as R 102 , with the proviso that T 101 and R 131 together and T 102 and R 132 together each contain at least 12 carbon atoms,
R 102 is a radical of the formulae

T 101 is a bridge having 2 to 9 carbon atoms, of which not more than one third may be replaced by O and/or NR 200 , where there must be at least 2 carbon atoms between O or NR 200 , and which may be arranged in the form of an optionally branched chain and/or a five- or six-membered ring,
R 131 is an optionally branched and/or optionally substituted C 4 - to C 16 -alkyl radical, an optionally branched and/or optionally substituted C 4 - to C 16 -alkenyl radical, a cyclopentyl or cyclohexyl radical, a benzyl, phenethyl or phenylpropyl radical, a phenyl radical or heterocyclic radical optionally substituted by nonionic radicals, an optionally branched and/or optionally substituted C 4 - to C 16 -alkoxy radical, a cyclopentoxy or cyclohexoxy radical, a benzyloxy, phenethyloxy or phenylpropoxy radical, a phenoxy radical or heteroaryloxy radical optionally substituted by nonionic radicals, an optionally branched and/or optionally substituted C 4 - to C 22 -alkylamino radical, a cyclopentylamino or cyclohexylamino radical, a benzylamino, phenethylamino or phenylpropylamino radical, a phenylamino radical or heteroarylamino radical optionally substituted by nonionic radicals,
T 102 is a bridge having 1 to 9 carbon atoms which may be arranged in the form of an optionally branched chain and/or a five- or six-membered ring,
R 132 is an optionally branched and/or optionally substituted C 1 - to C 16 -alkyl radical, a cyclopentyl or cyclohexyl radical, a benzyl, phenethyl or phenylpropyl radical, a phenyl radical or heterocyclic radical optionally substituted by nonionic radicals,
A is NR 201 or oxygen,
R 200 and R 201 are independently hydrogen, methyl or ethyl,
R 103 and R 104 are independently an optionally branched and/or optionally substituted C 1 - to C 5 -alkyl radical
or
R 102 is a radical of the formulae

T 101 , R 131 , T 102 , R 132 , R 200 , R 201 and A have the definition given above, with the proviso that T 101 and R 131 together and T 102 and R 132 together each contain 12 carbon atoms,
R 101 , R 103 and R 104 together with the N + atom form an imidazole or pyridine ring substituted at least by one radical selected from C 1 - to C 6 -alkyl, C 1 - to C 6 -alkoxy, cyclopentyl, cyclohexyl, benzyl or phenyl
or

R 101 is an optionally branched C 14 - to C 22 -alkyl radical or is additionally defined as R 102 , with the proviso that T 101 and R 131 together and T 102 and R 132 together each contain at least 12 carbon atoms,
R 102 is a radical of the formulae

and T 101 , R 131 , T 102 , R 132 , R 200 , R 201 and A have the definition given above,

R 103 and R 104 together form a —(CH 2 ) 4 —, —(CH 2 ) 5 — or —(CH 2 ) 2 —O—(CH 2 ) 2 — bridge
and

R 1 and R 4 are as defined above.

3. The compounds of claim 1 , wherein
R 101 is an optionally branched C 14 - to C 22 -alkyl radical,
R 102 is a radical of the formulae

T 101 is a bridge in the form of an optionally branched chain which has 2 to 8 carbon atoms and may

Assignees

• Covestro Deutschland Ag
• Covestro Intellectual Property Gmbh & Co Kg

Inventors

• Rölle Thomas
• Berneth Horst
• Hönel Dennis
• Bruder Friedrich-Karl
• Kintrup Jürgen

Classifications

• C07D309/34

  having three or more double bonds between ring members or between ring members and non-ring members · CPC title

• C07C271/16

  to carbon atoms of hydrocarbon radicals substituted by singly-bound oxygen atoms · CPC title

• C07D335/02

  not condensed with other rings · CPC title

• C07D247/00

  Heterocyclic compounds containing rings having two nitrogen atoms as the only ring hetero atoms, according to more than one of groups C07D229/00 - C07D245/00 · CPC title

• C07D233/02

  having no double bonds between ring members or between ring members and non-ring members · CPC title