Patent CH-694732-A5 (CH)
Title: Metal-organic monoacyl-aryl-phosphine compounds, used for the production of acyl-phosphine, -phosphine oxide or -phosphine sulfide compounds for use as photoinitiators in light-cured compositions, e.g. paint
Inventor: WOLF JEAN-PIERRE
IPC: C08F2/50
Filed: 2001-02-01
Abstract: Metal-organic monoacyl-aryl-phosphine compounds are new. Metal-organic monoacyl-aryl-phosphine compounds (I) are new. [Image] Ar : a group of the formula (Ia), or cyclopentyl, cyclohexyl naphthyl, biphenylyl, anthracyl, or an O-, S- or N-containing 5- or 6-membered heterocycle (all optionally substituted with halogen, 1-4C alkyl and/or 1-4C alkoxy); R 1, R 21-20C alkyl, OR 11, CF 3or halogen; R 3-R 5H, 1-20C alkyl, OR 11or halogen, or any two of the groups R 1-R 5may form a 1-20C alkylene group (optionally with in-chain O, S or NR 14); R 6-R 10H, 1-20C alkyl, 2-20C alkyl with one or more non-adjacent in-chain oxygen atoms (optionally substituted with OH and SH), OR 11, phenyl or halogen; R 11H, 1-20C alkyl, 2-20C alkyl with in-chain O or S and optionally substituted with OH and/or SH, 2-20C alkenyl, 3-8C cycloalkyl, phenyl or benzyl; R 14H, phenyl, 1-12C alkyl or 2-12C alkyl with in-chain O or S (optionally substituted with OH and/or SH); M : H, lithium, sodium or potassium. Independent claims are also included for: (a) compounds of formula (II) and (III); (b) a method for the selective production of (I) by reacting an acyl halide of formula Ar-COX (IV) with a dimetallated arylphosphine of formula Ar-PM 2(V), using a mole ratio of 1:1, and then hydrolysing the product if compounds (I) with M = H are required; (c) production of (II) by reacting (IV) with (V) as above and then reacting the product with a different acyl halide of formula Y 1-COX (followed by oxidation or sulfurization if compounds with A = O or S are required); (d) a method for the production of (III) by reacting (IV) with (V) as above and then reacting the product with Z 1-X (optionally followed by oxidation or sulfurization); (e) light-curable compositions containing photopolymerizable, ethylenically unsaturated compound(s) and compound(s) (II) or (III) as photoinitiator; (f) a method for the photopolymerization of non-volatile, mono-, oligo- or poly-meric compounds with at least one olefinic double bond by irradiating compositions with light in the wavelength range 200-600 nm; (g) substrates with at least one surface coated with a composition as above; (h) a method for the photographic production of relief images, in which coated substrates as in (g) are irradiated to form an image and the unirradiated areas are then removed with a solvent. [Image] A : O or S; preferably O; x : 0 or 1; preferably 1; Y 1various optionally substituted groups (10 types listed, including 1-18C alkyl, naphthyl, OR 11and another residue of formula (II) linked by Y 2); Y 2a direct bond or a divalent organic group (7 types listed, including 1-18C alkylene and naphthylene); Z 1various optionally substituted groups (20 types listed, including 1-24C alkyl, substituted aryl or heteroaryl, another residue of (III) linked by Z 2, and organosil(ox)anyl); Z 2a divalent group (6 optionally substituted types listed, including 1-24C alkylene, arylene and organosil(ox)ane residues) X : Cl or Br; Ar : phenyl substituted with groups R 6-R 10; M : Na, Li or K R : an alcohol residue.