Radiation-curable compounds

Patent metadata

Field	Value
Publication number	US-2016145453-A1
Application number	US-201615009182-A
Country	US
Kind code	A1
Filing date	Jan 28, 2016
Priority date	May 30, 2012
Publication date	May 26, 2016
Grant date	—

Abstract

The invention relates to low-viscosity formulations of radiation-curable compounds, to processes for preparing them, to their use, and to inks, printing-inks, and print varnishes that comprise them.

First claim

1 - 14 . (canceled)

15 . A formulation of an incorporable photoinitiator, comprising:
a polyurethane A, 0.5% to 4% by weight of water, based on an amount of the polyurethane A, and optionally a polyfunctional polymerization compound B, wherein the polyurethane A comprises, in reacted form: (a) an organic polyisocyanate comprising an allophanate group and having an NCO functionality of at least 2, synthesized from an aliphatic C 4 to C 20 alkylene diisocyanate, (b) a compound having at least one isocyanate-reactive group and at least one radically polymerizable unsaturated group, (c) a photoinitiator having at least one isocyanate-reactive group, (d) optionally a further diisocyanate, polyisocyanate, or both, which is different from (a), (e) optionally a compound having at least two isocyanate-reactive groups, and (f) optionally a compound having precisely one isocyanate-reactive group.

16 . The formulation of claim 15 , wherein the photoinitiator having at least one isocyanate-reactive group (c) is represented by a member selected from the group consisting of

wherein
R 3 , R 4 , and R 5 each independently of one another are hydrogen, an alkyl group comprising 1 to 4 carbon atoms or an alkyloxy group comprising 1 to 4 carbon atoms,
p is 0 or an integer from 1 to 10,
Y i for i=1 to p independently of one another are selected from the group consisting of —CH 2 —CH 2 —O—, —CH 2 —CH(CH 3 )—O—, —CH(CH 3 )—CH 2 —O—, —CH 2 —C(CH 3 ) 2 —O—, —C(CH 3 )—CH 2 —O—, —CH 2 —CHVin-O—, —CHVin-CH 2 —O—, —CH 2 —CHPh-O—, and —CHPh-CH 2 —O,
Ph is phenyl, and
Vin is vinyl.

17 . The formulation of claim 15 , wherein the photoinitiator having at least one isocyanate-reactive group (c) is selected from the group consisting of 2-hydroxy-2-methyl-1-phenyl-propan-1-one, 1-hydroxycyclohexyl phenyl ketone, 1-[4-(2-hydroxyethoxy)phenyl]-2-hydroxy-2-methyl-1-propan-1-one, 2-hydroxy-1-{4-[4-(2-hydroxy-2-methyl-propionyl)benzyl]phenyl}-2-methylpropan-1-one, 2-hydroxy-1-[4-[hydroxy[4-(2-hydroxy-2-methylpropanoyl)phenyl]methyl]phenyl]-2-methyl-propan-1-one, [4-[3-(4-benzoylphenoxy)-2-hydroxypropoxy]phenyl]phenylmethanone, benzoin, benzoin isobutyl ether, benzoin tetrahydropyranyl ether, benzoin methyl ether, benzoin ethyl ether, benzoin butyl ether, benzoin isopropyl ether, 7H-benzoin methyl ether, 2-hydroxy-2,2-dimethylacetophenone, and 1-hydroxyacetophenone.

18 . An ink, printing-ink or print varnish, comprising:
the formulation of claim 15 , the polyfunctional polymerizable compound B, optionally a pigment, optionally a further photoinitiator, and optionally an additive.

19 . The ink, printing-ink or print varnish of claim 18 , comprising the further photoinitiator, which is selected from the group consisting of 2,4,6-trimethylbenzoyldiphenylphosphine oxide, ethyl 2,4,6-trimethylbenzoylphenylphosphinate, bis(2,4,6-trimethylbenzoyl)phenylphosphine oxide, 2-benzyl-2-dimethylamino-4′-morpholinobutyrophenone, 2-(dimethylamino)-1-(4-morpholinophenyl)-2-(p-tolylmethyl)butan-1-one, 2-hydroxy-1-[4-[[4-(2-hydroxy-2-methylpropanoyl)phenyl]methyl]phenyl]-2-methylpropan-1-one, a polymeric benzophenone derivative, a polymeric thioxanthone derivative, a polymeric α-amino ketone, and a silsesquioxane compound having at least one initiating group.

20 . A method of printing on a material selected from the group consisting of polyamide, polyethylene, polypropylene, polyester, polyethylene terephthalate, polystyrene, paper, paperboard, cardboard, plastics-coated paper, plastics-coated paperboard, plastics-coated cardboard, aluminum, and an aluminum-coated polymeric films, the method comprising contacting the ink, printing-ink or print varnish of claim 18 with the material.

21 . The method of claim 20 , wherein the material is a food packaging, a cosmetic packaging material, or a pharmaceutical packaging material.

Assignees

• Basf Se

Inventors

• Kaczun Juergen
• Schwalm Reinhold
• Trumbo David
• Sitzmann Eugene Valentine

Classifications

• C09D151/08

  grafted on to macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds · CPC title

• C08G18/6795

  Unsaturated polyethers · CPC title

• C08G18/8125

  having two or more isocyanate or isothiocyanate groups · CPC title

• C09D11/101 Primary

  Inks specially adapted for printing processes involving curing by wave energy or particle radiation, e.g. with UV-curing following the printing · CPC title

• C09D175/04

  Polyurethanes · CPC title