(Meth)acrylates containing urethane groups

• US 5,495,029 A
• Filed: 08/04/1994
• Issued: 02/27/1996
• Est. Priority Date: 08/09/1993
• Status: Expired due to Term

• Current Assignee: 3D Systems, Inc. (3D Systems Corporation)
• Original Assignee: Ciba-Geigy Corporation (Novartis Ag)
• Inventors: Wolf, Jean-Pierre, Schulthess, Adrian, Hunziker, Max, Steinmann, Bettina
• Primary Examiner(s): Raymond, Richard L.
• Application Number:
  US08/286,061
• Time in Patent Office: 572 Days
• Field of Search: 548/546, 549/544, 549/545, 549/546, 549/553, 560/26, 560/115, 560/158
• US Class Current: 549/545
• CPC Class Codes: B33Y 70/00 Materials specially adapted for additive manufacturing
• CPC Class Codes: C07C 2601/14 The ring being saturated
• CPC Class Codes: C07C 2601/16 the ring being unsaturated
• CPC Class Codes: C07C 2603/70 containing only six-membered rings
• CPC Class Codes: C07C 271/12 to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
• CPC Class Codes: C07C 271/24 with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a ring other than a six-membered aromatic ring
• CPC Class Codes: C07C 271/28 to a carbon atom of a non-condensed six-membered aromatic ring
• CPC Class Codes: C07C 271/34 with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
• CPC Class Codes: C07C 271/36 with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a ring other than a six-membered aromatic ring
• CPC Class Codes: C07C 271/38 with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a six-membered aromatic ring
• CPC Class Codes: C07D 303/16 by esterified hydroxyl radicals
• CPC Class Codes: C08F 20/36 containing oxygen in addition to the carboxy oxygen , e.g. 2-N-morpholinoethyl (meth)acrylate or 2-isocyanatoethyl (meth)acrylate
• CPC Class Codes: C08F 222/1065 of alcohol terminated (poly)urethanes, e.g. urethane(meth)acrylates
• CPC Class Codes: C08G 18/675 Low-molecular-weight compounds
• CPC Class Codes: C08G 59/1494 followed by a further chemical treatment thereof
• CPC Class Codes: C09D 4/00 Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
• CPC Class Codes: G03F 7/0037 Production of three-dimensional images
• CPC Class Codes: G03F 7/027 Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds G03F7/075 takes precedence

Abstract

Novel (meth)acrylates containing urethane groups Novel (meth)acrylates which also contain urethane groups and other polymerizable groups in one and the same molecule and can be polymerized either by means of free radicals and/or cationically are used for the production of coatings, adhesives, photoresists, solder masks or in stereolithography. The mouldings produced therefrom contain a coherent, homogeneous network and have high strength properties, in particular mechanical properties.

Claims

1. A (meth)acrylate of the formula I containing urethane groups ##STR31## in which R is a divalent group of the formula ##STR32## R₁ is a cationically polymerizable group or a free-radical-polymerizable group, with the exception of the acrylate and allyl groups,

R₂ is an aliphatic, cycloaliphatic or aromatic radical,

R₃ is hydrogen or CH₃,

R₄ is the radical of an aliphatic, cycloaliphatic or aromatic diglycidyl compound after removal of the diglycidyl radical, or is the radical of a cycloaliphatic diepoxide, and

R₅ is a cycloaliphatic bridge.

2. A (meth)acrylate of the formula I containing urethane groups according to claim 1, in which R₁ is a cationically polymerizable group of the formula ##STR33## or a free-radical-polymerizable group of the formula ##STR34## in which x is an integer from 2 to 20, and y is an integer from 1 to 20.

3. A (meth)acrylate containing urethane groups according to claim 2, in which R₁ is a cationically polymerizable group.

4. A (meth)acrylate of the formula I containing urethane groups according to claim 1, in which R₂ and R₄, independently of one another, are a C₄ -C₂₀ aliphatic bridge, which may be interrupted by at least one ether, ester, urethane, amide or aryle, ne group, and furthermore are a cycloaliphatic or aromatic bridge.

5. A (meth)acrylate containing urethane groups according to claim 4, in which R₂ is a C₄ -C₂₀ aliphatic or an aromatic bridge or a plurality of aromatic groups interrupted by aliphatic groups.

6. A (meth)acrylate containing urethane groups according to claim 4, in which R₄ is a C₄ -C₂₀ aliphatic bridge interrupted by at least one ether or ester group, or is an aromatic bridge.

7. A (meth)acrylate containing urethane groups according to claim 2, in which x and y are integers from 1 to 6.