Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – Polymers from only ethylenic monomers or processes of...
Patent
1996-06-28
1997-12-23
Schofer, Joseph L.
Synthetic resins or natural rubbers -- part of the class 520 ser
Synthetic resins
Polymers from only ethylenic monomers or processes of...
526270, C08F 2602
Patent
active
057008914
DESCRIPTION:
BRIEF SUMMARY
BACKGROUND OF THE INVENTION
1. Field of the Invention
The present invention pertains to a low-odor adhesive composition based on (meth)acrylates containing urethane groups and the use thereof.
The invention further pertains to a polyurethane (meth) acrylate based on special polyesterdiols which may also be components of the adhesive compositions according to the invention.
2. Discussion of the Related Art
Methyl methacrylate is the most widely used monomer in commercial, free-radical curing reactive adhesives. In spite of the good adhesive properties of these systems, their use is increasingly restricted for olfactory reasons. The liquid esters of acrylic or methacrylic acid with longer aromatic or aliphatic side chains also all have an intensive odor and/or poor adhesive properties.
Therefore, the development of low-odor adhesive compositions is of great interest which compositions must be liquid or paste-like at room temperature.
EP-A-0 542 219 describes polyurethane (meth)acrylates based on polyfunctional isocyanates and special diols containing at least 8 carbon atoms, in particular 2-ethyl-3-propyl-1,5-pentanediol and/or its derivatives, as well as the use thereof in combination with a free-radical initiator as a coating, additive in inks, sealant or adhesive. EP-A-0 542 219 further describes the combination of the polyurethane (meth) acrylates with other acrylates and methacrylates.
WO-A-86/01153 and U.S. Pat. No. 4,600,640 describe adhesives for connecting a thin glass plate with a thermoplastic substrate using a solvent-free UV-curable adhesive composition containing a (meth)acrylate monomer the ester group of which contains a urethane group. Further, there are described urethane (meth)acrylates of the general formula
R.sup.6 or R.sup.2 is, for example, a methylene, ethylene or propylene group, R' is a methyl group or hydrogen, R.sup.7 or Q is an aliphatic, cycloaliphatic or aromatic group. Particularly preferred as an adhesive are 2-acryloyloxyethyl-N-phenylcarbamate, 2-methacryloyloxypropyl-N-phenylcarbamate, 2-acryloyloxypropyl-N-phenylcarbamate, and acryloyloxyethyl-N-n-butylcarbamate.
DE-A-27 27 109 describes UV-curable compositions consisting of a mixture of a monoacrylate containing a urethane group and a polyurethane (meth)acrylate. The cured compositions exhibit excellent resistance to tropic humidity with respect to their toughness properties.
The polyurethane (meth)acrylates are reaction products of hydroxypropyl acrylate or methacrylate or hydroxyethyl acrylate with hexamethylene-, isophorone- or toluenediisocyanate, the monoacrylates are those of phenylisocyanate.
U.S. Pat. No. 4,439,600 describes a composition comprising (A) a reaction product of a polyesterdiol (from adipic acid and diethylene glycol) and an aliphatic or aromatic diisocyanate, and (B) a comonomer which is a reaction product of an isocyanate and hydroxyethyl methacrylate (HEMA), or 2-hydroxypropyl methacrylate, or 2-hydroxypropyl acrylate. The final products exhibit special wetting, swelling and adhesive properties as well as low volatility.
Proceeding from there, it has been the object of the present invention to provide low-odor adhesive compositions based on (meth)acrylates containing urethane groups which are liquid or paste-like and which when cured have a special resistance to humidity (hydrolysis resistance). The adhesive compositions should further have a long shelf-life and be suitable for one- and two-component adhesive systems and exhibit good adhesion on glass, wood, paper, metals and plastics as well as viscoplastifying properties.
OBJECTS OF THE INVENTION
This object has been achieved, according to the invention, by a composition containing an activator system for free-radical polymerizations and a free-radical polymerizable compound of the general formula II: --O--C(.dbd.O)--NH--Q'--NH--C(.dbd.O)}.sub.m --O--R.sup.4a --O--!(II) carbon atoms or an alkylene oxide containing from 4 to 21 carbon atoms; containing from 6 to 18 carbon atoms which are derived from the basic diisocyanate or diisocyanate mix
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Emmerling Winfried
Friese Carsten
Huver Thomas
Kux Michael
Motzkat Kerstin
Henkel Kommanditgesellschaft auf Aktien
Jaeschke Wayne C.
Meder Martin G.
Sarafim N.
Schofer Joseph L.
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