Ciba Specialty Chemicals Corporation

Other

Basf Se Corporation

Martin Kunz

Allan Francis Cunningham

Hisatoshi Kura

Kurt Dietliker

Michael Bauer

Jean-Luc Birbaum

Hitoshi Yamato

Christoph De Leo

Toshikage Asakura

Hidetaka Oka

Akira Kimura

André Fuchs

Rinaldo Hüsler

Manfred K&ouml;hler

Ljubomir Misev

Andreas Baranyai

Hiroko Nakashima

Christian Schregenberger

Christopher Curtis Dudman

Hartmut Bleier

Giorgio Macor

A process for the production of strongly adherent coatings on an inorganic or organic substrate is provided, wherein in a first step

Process for the production of strongly adherent coatings

The invention relates to &#x3b1;-hydroxy ketones of formula I or IIa; or mixtures of compounds of formula I and II; or mixtures of compounds of formulae Ia and IIa 

Difunctional photoinitiators

Alkylsulfonyloximes for high-resolution i-line photoresists of high sensitivity

The invention relates to a process for the production of strongly adherent coatings on an inorganic or organic substrate, in which process in a first step: a) the inorganic or organic substrate is subjected to the action of a low-temperature plasma discharge, a corona discharge, high-energy UV radiation or electron radiation, the radiation or discharge is then discontinued, in a further step: b) at least one electron- or H-donor, each containing at least one ethylenically unsaturated group, is applied to the inorganic or organic substrate in vacuo or at normal pressure and reacted with the free radicals formed there, and c1) the substrate so precoated with coinitiator is coated with a composition comprising at least one ethylenically unsaturated monomer or oligomer and a photoinitiator, and the coating is cured by means of electromagnetic and/or ionizing radiation; or c2) the substrate so precoated with coinitiator is coated with a composition comprising at least one ethylenically unsaturated monomer or oligomer and one or more thermally activatable initiators, and the coating is cured thermally. The invention relates also the use of electron- or H-donors, for example amines, thioethers or thiols, having at least one ethylenically unsaturated group in the production of such layers and to the strongly adherent coatings themselves.

Process for the production of strongly adherent surface-coatings by plasma-activated grafting

Method for producing adhesive surface coatings

Borate coinitiators for photopolymerization

Dye compounds of the formula ##STR1## wherein X is for example CH, C--CH.sub.3 or .sup.+ NOR L.sup.- ; R is inter alia C.sub.1 -C.sub.6 alkyl; R.sub.1 is for example C.sub.1 -C.sub.8 alkoxy or C.sub.1 -C.sub.12 alkyl; s is 0 to 4; R.sub.2 is for example hydrogen; Ar is for example a group ##STR2## Y inter alia is C.sub.1 -C.sub.6 alkyl or C.sub.1 -C.sub.6 alkoxy; r in the formula (A) is 0 to 5, in the formulae (B) and (E) is 0 to 9 and in the formula (D) is 0 to 7; and L is an anion; in combination with an electron donor compound, especially a borate compound, are suitable as photoinitiators for the photopolymerization of radically polymerizable compositions.

Quinolinium dyes and borates in photopolymerizable compositions

Polymerizable composition

Compounds of the formula I and II ##STR1## in which R.sub.1, R.sub.2 and R.sub.3 are, for example, unsubstituted or substituted phenyl, where none of the radicals R.sub.1 -R.sub.3 is a phenyl radical which is substituted ortho to the bond to the borate atom;

Polyborate coinitiators for photopolymerization

Compounds of formula I, II or III ##STR1## X is a divalent radical; Y is C.sub.1 -C.sub.6 aklylene, cyclohexylene or a direct bond;

Photogeneration of amines from .alpha.-aminoacetophenones

Compounds of the formula I ##STR1## in which n and o are a number from 0 to 50, m is a number from 1 to 50, u and v are 0 or 1, and at least one of the indices u and v is 1, R.sub.1, R.sub.2, R.sub.2a, R.sub.3 and R.sub.4 independently of one another are, for example, aromatic hydrocarbons, R.sub.5, if n and o are 0, is for example C.sub.1 -C.sub.12 alkyl and, if n and/or o are greater than 0, or if n and o are 0 and at the same time only one index u or v is 1, R.sub.5 may additionally, for example, be an aromatic hydrocarbon, at least one of the radicals R.sub.1, R.sub.2, R.sub.2a, R.sub.3, R.sub.4 and R.sub.5 being an aromatic hydrocarbon radical which is sterically hindered ortho to the boron atom, X is, for example, C.sub.1 -C.sub.20 alkylene, phenylene, biphenylene, etc., and Z is a radical which is able to form positive ions, are suitable as photoinitiators, both the compounds per se and their combination with dyes or other electron acceptors. Furthermore, the polyborane precursors of these borates possess, together with borate salts, photoinitiating properties.

Polyborane photoinitiators and borate photoinitiators from polyboranes

The invention relates to photopolymerizable compositions comprising as photoinitiator a borate of the formula I or I' ##STR1## R.sub.1, R.sub.2 and R.sub.3 are, for example and independently of one another, phenyl or another aromatic hydrocarbon, with or without any heteroatoms, which radicals are unsubstituted or are substituted, or the radicals R.sub.1 and R.sub.2 form bridges to produce structures of the formula II, IIa or IIb ##STR2## with the provisos that not more than two of the radicals R.sub.1, R.sub.2 and R.sub.3 are identical and either at least two of the radicals R.sub.1, R.sub.2 and R.sub.3 are aromatic hydrocarbon radicals or phenyl radicals which are substituted in both ortho-positions or at least one radical R.sub.1, R.sub.2 or R.sub.3 is a sterically bulky aryl radical and the remaining radicals of R.sub.1, R.sub.2 and R.sub.3 are aromatic hydrocarbon radicals or are phenyl radicals which are substituted in at least one ortho-position; R.sub.4 is, for example, phenyl or C.sub.1 -C.sub.20 alkyl and G is a radical which is able to form positive ions.

Borate photoinitiators from monoboranes

The invention relates to the use of oximesulfonic acid esters of formula I ##STR1## m is 0 or 1 and x is 1 or 2; R.sub.1 is, for example, substituted phenyl, R.sub.2 has, for example, one of the meanings of R.sub.1 or is unsubstituted phenyl, C.sub.1 -C.sub.6 alkanoyl, unsubstituted or substituted benzoyl, C.sub.2 -C.sub.6 alkoxycarbonyl or phenoxycarbonyl; or R.sub.1 and R.sub.2, if necessary together with the CO group, form a ring, R.sub.3, when x is 1, is, for example, C.sub.1 -C.sub.18 alkyl, phenyl or phenanthryl, the radicals phenyl and phenanthryl being unsubstituted or substituted, or R.sub.3, when x is 2, is, for example, C.sub.2 -C.sub.12 alkylene, phenylene or oxydiphenylene, the radicals phenylene and oxydiphenylene being unsubstituted or substituted, as latent acid donors, especially at wavelengths over 390 nm, and to the use of the compounds in the production of photoresists.

Oximesulfonic acid esters and the use thereof as latent sulfonic acids

Compounds of the formula I ##STR1## in which R.sub.1 is, for example, C.sub.1 -C.sub.20 alkyl or phenyl-C.sub.1 -C.sub.6 alkyl which radicals are unsubstitutedor substituted; R.sub.2, R.sub.3 and R.sub.4 independently of one another are phenyl or biphenyl, which radicals are unsubstituted or substituted; wherein the sum of the Hammett .sigma. constants (.SIGMA..sub..sigma.) of the substitutents on the aromatic radicals R.sub.2, R.sub.3 and R.sub.4 is between +0.36 and +2.58; R.sub.8, R.sub.9, R.sub.14, R.sub.15 and R.sub.16 are, for example, C.sub.1 -C.sub.12 alkyl, phenyl-C.sub.1 -C.sub.6 alkyl or phenyl, and G is a radical which is able to form positive ions. These compounds are suitable as photoinitiators for photopolymerizable compositions which contain acid groups, in the presence of a coinitiator if desired.

Acid-stable borates for photopolymerization

New oximsulfonate compounds of the formulae I or II, ##STR1## wherein m is 0 or 1; x is 1 or 2; R.sub.1 is, for example phenyl, which is unsubstituted or substituted or R.sub.1 is a heteroaryl radical that is unsubstituted or substituted, or, if m is 0, R.sub.1 additionally is C.sub.2 -C.sub.6 alkoxycarbonyl, phenoxycarbonyl or CN; R'.sub.1 is for example C.sub.2 -C.sub.12 alkylene, phenylene; R.sub.2 has for example one of the meanings of R.sub.1 ; n is 1 or 2; R.sub.3 is for example C.sub.1 -C.sub.18 alkyl, R'.sub.3 when x is 1, has one of the meanings given for R.sub.3, or R'.sub.3 in the formula IV and when x is 2 in the formula 1, is for example C.sub.2 -C.sub.12 alkylene, phenylene; R.sub.4 and R.sub.5 are independently of each other for example hydrogen, halogen, C.sub.1 -C.sub.6 alkyl; R.sub.6 is for example hydrogen, phenyl; R.sub.7 and R.sub.8 are independently of each other for example hydrogen or C.sub.1 -C.sub.12 -alkyl; R.sub.9 is for example C.sub.1 -C.sub.12 alkyl; A is S, O, NR.sub.6, or a group of formula A1, A2, A3 or A4 ##STR2## R.sub.10 and R.sub.11 independently of each other have one of the meanings given for R.sub.4 ; R.sub.12, R.sub.13, R.sub.14 and R.sub.15 independently of one another are for example hydrogen, C.sub.1 -C.sub.4 alkyl; Z is CR.sub.11 or N; Z.sub.1 is --CH.sub.2 --, S, O or NR.sub.6, are useful as latent sulfonic acids, especially in photoresist applications.

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Efringen-Kirchen, Germany

Martin Kunz