Cycloaliphatic acrylic monomer

Details Cycloaliphatic acrylic monomer Cycloaliphatic acrylic monomer

1995-07-19

1996-09-24

Schofer, Joseph L.

Synthetic resins or natural rubbers -- part of the class 520 ser

Synthetic resins

Polymers from only ethylenic monomers or processes of...

549374, 522184, C08F22400, C08F 246, C07D31906

Patent

active

055592015

DESCRIPTION:

BRIEF SUMMARY
The present invention relates to a cycloaliphatic acrylic monomer based on ethoxylated, propoxylated, butoxylated and/or phenylethoxylated 1,3-dioxane alcohols, which acrylic monomer primarily is intended as a component in radiation curing compositions.
Radiation curing compositions are well-known technologies and used in for instance printing inks, paints and lacquers for furniture and packaging materials as well as for adhesives, but can also comprise application areas such as dental materials. Radiation curing compositions are environmentally suitable and pleasing as they do not contain volatile solvents. They exhibit furthermore a rapid curing and through hardening when exposed to for instance ultra-violet (UV) light or electron-beams (EB). The compositions most often contain one or more oligomers having an unsaturation, normally as acrylate. These oligomers are usually high viscous and are, to obtain applicable viscosities, diluted with various monomers. The monomers are most often acrylic monomers, which monomers are esters of alcohols and acrylic or methacrylic acid. The most commonly used acrylic monomers normally have an acrylate functionality within the range of 1-4.
In radiation curing compositions used acrylic monomers include:


______________________________________ Monofunctional: 2-Ethylhexyl acrylate 2-(2-ethoxyethoxy)ethyl acrylate Isobornyl acrylate Octyldecyl acrylate Difunctional: Tripropylene glycol diacrylate 1,6-hexanediol diacrylate Neopentyl glycol diacrylate Neopentyl glycol ethoxylate diacrylate Trifunctional: Pentaerythritol triacrylate Trimethylolpropane triacrylate Trimethylolpropane ethoxylate triacrylate Glycerol propoxylate triacrylate Tetrafunctional: Pentaerythritol ethoxylate tetracrylate Di-trimethylolpropane tetracrylate ______________________________________
Some of the above listed acrylic monomers are not included in the list of monomers issued by the Society of British Ink Manufactures Ltd., which list voluntarily exclude monomers that due to for instance a high irritation index or toxicity not are acceptable for use in radiation curing coatings for the printing industry.
High viscous acrylic monomers having an acrylate functionality of 5 and even higher, such as dipentaerythritol pentacrylate, are also used for specific purposes.
Besides the above exemplified acrylic monomers are the cycloaliphatic 5-ethyl-1,3-dioxane-5-methanol monoacrylate and acrylates of allyl alcohols, such as trimethylolpropane allyl ethers, known.
Acrylic monomers are generally highly reactive and as such potentially hazardous being skin and eye irritants and possible sensitizers. The properties in relation to the acrylate functionality can be summarised: properties and the higher are the skin irritation, toxicity, volatility and odour. properties and the flexibility and the higher are the reactivity, hardness and resistance. Low functional, i.e. mono and difunctional, acrylic monomers must, besides the excellent dilution properties, exhibit low skin irritation and low or no odour to comply with industrial hygienic demands. Above properties must, if the monomers are to be utilised properly, be combined with for instance good reactivity, final hardness and resistance. Presently available mono and difunctional acrylic monomers are most often either skin/eye irritating, highly toxic and/or highly volatile or exhibit poor film forming properties such as poor hardness and/or poor resistance. Thus, the skin irritation value for the above disclosed monomer 5-ethyl-1,3-dioxane-5-methanol monoacrylate has from evaluations performed according to OECD Guideline for Testing of Chemicals no. 404, "Acute Dermal Irritation/Corrosion" of 12 May 1983, been determined to be 2.6/2.8 (erythema/oedema). These values prove, according to "Directive of the Commission 83/467/EEC" of 29 Jul. 1983, as published in "Official Journal of the European Communities" L 257, 1983, that the monomer is to be classified as skin irritant. It can furthermore be noted that neopentyl glycol di

REFERENCES:
patent: 3267084 (1966-08-01), Rankin et al.
patent: 5004798 (1991-04-01), Broussard et al.
patent: 5059698 (1991-10-01), Schulthess et al.
Abstract of L.

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