Method for producing triarylorganoborates

Patent metadata

Field	Value
Publication number	US-11760765-B2
Application number	US-202016950906-A
Country	US
Kind code	B2
Filing date	Nov 18, 2020
Priority date	Nov 9, 2016
Publication date	Sep 19, 2023
Grant date	Sep 19, 2023

Abstract

The invention relates to a process for preparing triaryl organoborates 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 (CC)

in which
R 301 and R 301′ are each independently an optionally branched C 14 - to C 22 -alkyl radical or are additionally defined as R 302 , with the proviso that T 301 and R 331 together and T 302 and R 332 together each contain at least 12 carbon atoms,
R 302 is a radical of the formulae

T 301 is a bridge having 2 to 16 carbon atoms, of which not more than one third may be replaced by O and/or NR 400 , 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 331 is an optionally branched and/or optionally substituted C 4 - to C 22 -alkylene radical, a cyclopentylene, cyclohexylene or cycloheptylene radical, a C 8 - to C 12 -aryldialkylene radical, an arylene radical or heteroarylene radical optionally substituted by nonionic radicals, an optionally branched and/or optionally substituted C 4 - to C 22 -alkanedioxy radical, a cyclopentanedioxy, cyclohexanedioxy or cycloheptanedioxy radical, a C 7 - to C 12 -oxyarylalkoxy radical, C 8 - to C 12 -aryldi(alkyloxy) radical, a benzenedioxy radical or heteroaryldioxy radical optionally substituted by nonionic radicals, an optionally branched and/or optionally substituted C 4 - to C 22 -alkanediamino radical, a cyclopentanediamino, cyclohexanediamino or cycloheptanediamino radical, a C 8 - to C 12 -aminoarylalkylamino radical, a benzenediamino radical or heteroarylenediamino radical optionally substituted by nonionic radicals, an alkylene-cycloalkylene radical, alkanedicycloalkylene radical or alkanediarylene radical,
T 302 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 332 is an optionally branched and/or optionally substituted C 1 - to C 22 -alkylene radical, a cyclopentylene, cyclohexylene or cycloheptylene radical, a C 8 - to C 12 -aralkylene radical, an arylene or heteroarylene radical optionally substituted by nonionic radicals,
A is NR 401 or oxygen,
R 400 and R 401 are independently hydrogen or C 1 - to C 4 -alkyl,
R 303 , R 304 , R 303′ and R 304′ are independently an optionally branched and/or optionally substituted C 1 - to C 5 -alkyl radical,
or
R 302 is a radical of the formulae

T 301 , R 331 , T 302 , R 332 , R 400 , R 401 and A have the definition given above, with the proviso that T 301 and R 331 together and T 302 and R 332 together each contain at least 12 carbon atoms,
R 301 , R 303 and R 304 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, and/or
R 301′ , R 303′ and R 304′ 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 301 and R 301′ are each independently an optionally branched C 14 - to C 22 -alkyl radical or are additionally defined as R 302 , with the proviso that T 301 and R 331 together and T 302 and R 332 together each contain at least 12 carbon atoms,
R 302 is a radical of the formulae

and
T 301 , R 331 , T 302 , R 332 , R 400 , R 401 and A have the definition given above,
R 303 and R 304 together form a —(CH 2 ) 4 —, —(CH 2 ) 5 — or —(CH 2 ) 2 —O—(CH 2 ) 2 — bridge, and/or
R 303′ and R 304′ 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 301 and R 301′ are each independently an optionally branched C 14 - to C 22 -alkyl radical or are additionally defined as R 302 , with the proviso that T 301 and R 331 together and T 302 and R 332 together each contain at least 12 carbon atoms,
R 302 is a radical of the formulae

T 301 is a bridge having 2 to 9 carbon atoms, of which not more than one third may be replaced by O and/or NR 400 , where there must be at least 2 carbon atoms between two O or NR 400 , and which may be arranged in the form of an optionally branched chain and/or a five-or six-membered ring,
R 331 is an optionally branched and/or optionally substituted C 4 - to C 16 -alkylene radical, a cyclopentylene or cyclohexylene radical, a xylylene, benzenediethylene or benzenedipropylene radical, an arylene radical or heteroarylene radical optionally substituted by nonionic radicals, an optionally branched and/or optionally substituted C 4 - to C 16 -alkanedioxy radical, a cyclopentanedioxy or cyclohexanedioxy radical, a benzenedi(methyloxy), benzenedi(ethyloxy) or benzenedi(propyloxy) radical, a benzenedioxy radical or heteroarylenedioxy radical optionally substituted by nonionic radicals, an optionally branched and/or optionally substituted C 4 - to C 22 -alkanediamino radical, a cyclopentanediamino or cyclohexanediamino radical, a benzenedi(methylamino), benzenedi(ethylamino) or benzenedi(propylamino) radical, a benzenediamino radical, methyldicyclohexylene radical, 4-methylenebis(4,1-phenylene) radical or heteroarylenediamino radical optionally substituted by nonionic radicals,
T 302 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 332 is an optionally branched and/or optionally substituted C 1 - to C 16 -alkylene radical, a cyclopentylene or cyclohexylene radical, xylylene, benzenediethylene or benzenedipropylene radical, an arylene or heteroarylene radical optionally substituted by nonionic radicals,
A is NR 401 or oxygen,
R 400 and R 401 are independently hydrogen, methyl or ethyl,
R 303 and R 304 are independently an optionally branched and/or optionally substituted C 1 - to C 5 -alkyl radical, and/or
R 303′ and R 304′ are independently an optionally branched and/or optionally substituted C 1 - to C 5 -alkyl radical,
or
R 302 is a radical of the formulae

T 301 , R 331 , T 302 , R 332 , R 400 , R 401 and A have the definition given above, with the proviso that T 301 and R 331 together and T 302 and R 332 together each contain 12 carbon atoms,
R 301 , R 303 and R 304 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, and/or
R 301′ , R 303′ and R 304′ together with the N + atom form an imidazole o

Assignees

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

Inventors

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

Classifications

• C07F9/54 Primary

  Quaternary phosphonium compounds · CPC title

• C07F5/027 Primary

  Organoboranes and organoborohydrides · CPC title

• 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

• C07C271/20

  to carbon atoms of hydrocarbon radicals substituted by nitrogen atoms not being part of nitro or nitroso groups · CPC title