Benzil monoketals and the use thereof

Patent metadata

Field	Value
Publication number	US-2020247916-A1
Application number	US-201615769826-A
Country	US
Kind code	A1
Filing date	Oct 5, 2016
Priority date	Oct 23, 2015
Publication date	Aug 6, 2020
Grant date	—

Abstract

in which the parameters have the meaning indicated in Claim 1, to sealants for liquid-crystal displays which comprise the hydrophilic photoinitiators, to novel hydrophilic photoinitiators of the formula I, and to the liquid-crystal displays produced using these sealants.

First claim

1 . A photopolymerization or crosslinking process, comprising photopolymerization of polymerizable substance mixtures which comprise unsaturated compounds, or photochemical crosslinking of linear polymers, by subjecting said unsaturated compounds or linear polymers to photopolymerization or crosslinking conditions respectively in the presence of an initiator of formula I

in which
R 1 , R 2 , independently of one another, denote a straight-chain or branched or cyclic alkyl, cycloalkylalkyl, arylalkyl, alkenyl or cycloalkylalkenyl radical having up to 20 C atoms or an arylalkenyl radical having 8 to 20 C atoms, in each of which one or more CH 2 groups may be replaced by —CO—, —O— and/or —S— in such a way that no O or S atoms are adjacent and in which one or more hydrogen atoms may be replaced by halogen, or both radicals R 1 and R 2 together denote a divalent bridging group W,
W denotes a divalent radical of an aliphatic, straight-chain or branched diol having 2 to 20 C atoms,
Ar 1 , Ar 2 , independently of one another, denote aryl radicals which are each substituted by one or more substituents L and which may additionally be substituted by halogen, alkyl, alkoxy, each having 1 to 5 C atoms, or phenyl,
L on each occurrence, identically or differently, denotes a hydrophilic radical.

2 . The process according to claim 1 , wherein, in formula I,
R 1 , R 2 , independently of one another, denote a straight-chain or branched alkyl radical having 1 to 7 C atoms, Ar 1 , Ar 2 , independently of one another, denote 1,4-phenylene, which is in each case substituted by a substituent L, L denotes —CH 2 -L′, —O-L′ or —N(L′) 2 , L′ denotes a straight-chain or branched alkyl radical having 1 to 19 C atoms, in which one or more CH 2 groups may be replaced by cycloalkanediyl radicals having 3 to 8 ring atoms and in which one or more non-adjacent CH 2 groups may be replaced by O and in which one or more H atoms may be replaced by —OH or

3 . The process according to claim 1 , wherein, in formula I,
R 1 , R 2 denote W, W denotes a divalent radical of an aliphatic, straight-chain or branched diol having 2 to 10 C atoms, Ar 1 , Ar 2 , independently of one another, denote 1,4-phenylene, which is in each case substituted by a substituent L, L denotes —CH 2 -L′, —O-L′ or —N(L′) 2 , L′ denotes a straight-chain or branched alkyl radical having 1 to 19 C atoms, in which one or more CH 2 groups may be replaced by cycloalkanediyl radicals having 3 to 8 ring atoms and in which one or more non-adjacent CH 2 groups may be replaced by O and in which one or more H atoms may be replaced by —OH or

4 . The process according to claim 1 , wherein the compounds of the formula I are compounds of the following sub-formulae:

where
L denotes —CH 2 -L′, —O-L′ or —N(L′) 2 ,
L′ denotes a straight-chain or branched alkyl radical having 1 to 19 C atoms, in which one or more CH 2 groups may be replaced by cycloalkanediyl radicals having 3 to 8 ring atoms and in which one or more non-adjacent CH 2 groups may be replaced by O and in which one or more H atoms may be replaced by —OH or

5 . The process according to claim 1 , wherein
L denotes —(CH 2 ) p OG, —O(CH 2 ) m+1 OG, —(CH 2 ) n (OCH 2 CH 2 ) m OG, —(O) n (CH 2 ) m CH(OH)CH 2 OG, —O(CH 2 CH 2 ) m+1 OCH 2 CH(OG)CH 2 -OG, —OC(CH 2 OG) 3 , —OC(CH 2 OG) 2 (CH 2 ) n H, —(CH 2 ) n OCH 2 CH(OH)CH 2 OG, —(OCH 2 CH 2 ) m OCH 2 CH(OG)CH 2 OG, —(CH 2 ) n OC—H 2 (CH) m ((CH 2 ) m OG) 2 , —(CH 2 ) n OC(CH 2 OG) 3 , —(CH 2 ) m OC(CH 2 OG) 2 (CH 2 ) n H, —N((CH 2 ) m+1 OG) 2 , —N((CH 2 CH 2 O) m G) 2 , —N((CH 2 ) m CH(OG)CH 2 OG) 2 or

m denotes an integer from 1 to 10,
n, p denote an integer from 0 to 10,
G denotes H,

 or
a monosaccharide radical selected from glucopyranose and glucofuranose,
with the proviso that G cannot be H if p is equal to 0.

6 . The process according to claim 1 , wherein the compounds of the formula I have an octan-1-ol/water partition coefficient of log P≤3.2.

7 . (canceled)

8 . A sealant for liquid-crystal displays, comprising a) one or more curable epoxide resins which comprise compounds which are each substituted by one or more epoxide groups and/or b) one or more (meth) acrylate compounds which are each substituted by one or more acrylate or methacrylate groups and/or c) one or more epoxide acrylate compounds which are substituted both by epoxide groups and by (meth)acrylate groups and d) a compound of the formula I

in which
R 1 , R 2 , independently of one another, denote a straight-chain or branched or cyclic alkyl, cycloalkylalkyl, arylalkyl, alkenyl or cycloalkylalkenyl radical having up to 20 C atoms or an arylalkenyl radical having 8 to 20 C atoms, in each of which one or more CH 2 groups may be replaced by —CO—, —O— and/or —S— in such a way that no O or S atoms are adjacent and in which one or more hydrogen atoms may be replaced by halogen, or both radicals R 1 and R 2 together denote a divalent bridging group W,
W denotes a divalent radical of an aliphatic, straight-chain or branched diol having 2 to 20 C atoms,
Ar 1 , Ar 2 , independently of one another, denote aryl radicals which are each substituted by one or more substituents L and which may additionally be substituted by halogen, alkyl, alkoxy, each having 1 to 5 C atoms, or phenyl,
L on each occurrence, identically or differently, denotes a hydrophilic radical.

9 . The sealant according to claim 8 , that is photochemically curable.

10 . The sealant according to claim 9 , that is additionally thermally curable.

11 . A compound of the formula I

in which
R 1 , R 2 , independently of one another, denote a straight-chain or branched or cyclic alkyl, cycloalkylalkyl, arylalkyl, alkenyl or cycloalkylalkenyl radical having up to 20 C atoms or an arylalkenyl radical having 8 to 20 C atoms, in each of which one or more CH 2 groups may be replaced by —CO—, —O— and/or —S— in such a way that no O or S atoms are adjacent and in which one or more hydrogen atoms may be replaced by halogen, or both radicals R 1 and R 2 together denote a divalent bridging group W,
W denotes a divalent radical of an aliphatic, straight-chain or branched diol having 2 to 20 C atoms,
Ar 1 , Ar 2 , independently of one another, denote aryl radicals which are each substituted by one or more substituents L and which may additionally be substituted by halogen, alkyl, alkoxy, each having 1 to 5 C atoms, or phenyl,
L on each occurrence, identically or differently, denotes a hydrophilic radical with the proviso that compounds of the formula I-1-1a

Assignees

• Merck Patent Gmbh

Inventors

• Kirsch Peer
• Tong qiong
• Hahn Alexander
• Weegels Leo
• Gnauck Steffen
• Schuepfer Sven
• Leonhard Peter
• Enders Claudia

Classifications

• G02F1/1339

  Gaskets; Spacers; Sealing of cells · CPC title

• C07C49/84 Primary

  containing ether groups, [IMAGE cpc-sch-C07C-0958.gif] groups,[IMAGE cpc-sch-C07C-0959.gif] groups, or[IMAGE cpc-sch-C07C-0960.gif] groups · CPC title

• C08F2/46 Primary

  Polymerisation initiated by wave energy or particle radiation · CPC title

• G02F2202/023

  curable · CPC title

• C07C225/22

  having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton · CPC title