Low viscosity urethane (meth)acrylate monomers and their use in production of tough polymers with well-controlled modulus and strength

A tetraurethane di(meth)acrylate (TUD(M)A) monomer according to Formula (I)

• wherein X is —H or —CH3;
• n is 1, 2, 3 or 4;
• and R is aliphatic, alkoxyalkyl, or alkylarylalkyl core group, optionally
• wherein wherein X is —H or —CH3;
• n is 1 or 2;
• and R is a straight or branched chain alkyl C2-C20, 1,2-diethoxyethane, ethoxyethane, 1-ethoxy-2-(2-ethoxyethoxy) ethane, 1-propoxypropane, 1,3-xylenyl radical, or a 1,4-xylenyl radical core group, further optionally wherein R is a core radical selected from the group consisting of

A monourethane mono(meth)acrylate monomer compound selected from the group consisting of:

• wherein R1=H, or CH3;
• n=1, 2, 3, 4, 5;
• n=1 for the IEM-BzOH monomer;
• n=2 for IEMEG-BzOH.

A mono-urethane di(meth)acrylate monomer compound according to Formula (IIIb):

• wherein R1=—H, —CH3;
• n=1 or 2;
• m=1-5, R2=aliphatic, aryl, alkylaryl;
• optionally wherein R2=Me, Et, nPr, iPr, nBu, sBu, tBu, Phe, or Bzl, optionally wherein the mono-urethane di(meth)acrylate monomer compound is selected from the group consisting of

A diurethane (meth)acrylate (DUM(M)A) monomer comprising a chemical structure according to Formula (IV):

• wherein X is —H or —CH3;
• n is 1, 2, 3 or 4;
• and R is aliphatic, alkoxyalkyl, or alkylarylalkyl core group, optionally
• wherein n=1 or 2, and R is a straight or branched chain alkyl C2-C20, 1,2-diethoxyethane, ethoxyethane, 1-ethoxy-2-(2-ethoxyethoxy) ethane, 1-propoxypropane, 1,3-xylenyl radical, or a 1,4-xylenyl radical core group.

A hexaurethane tri(meth)acrylate (HUT(M)A) monomer comprising a chemical structure according to Formula (V):

• wherein X is —H or —CH3;
• n is 1, 2, 3 or 4;
• and R is aliphatic, alkoxyalkyl, or alkylarylalkyl core group, optionally
• wherein n=1 or 2, and R is a straight or branched chain alkyl C2-C20, 1,2-diethoxyethane, ethoxyethane, 1-ethoxy-2-(2-ethoxyethoxy) ethane, 1-propoxypropane, 1,3-xylenyl radical, or a 1,4-xylenyl radical core group.

An octaurethane tetra(meth)acrylate (OUT(M)A) monomer comprising a chemical structure according to Formula (VI):

• wherein X is —H or —CH3;
• n is 1, 2, 3 or 4;
• and R is aliphatic, alkoxyalkyl, or alkylarylalkyl core group, optionally
• wherein n=1 or 2, and R is a straight or branched chain alkyl C2-C20, 1,2-diethoxyethane, ethoxyethane, 1-ethoxy-2-(2-ethoxyethoxy) ethane, 1-propoxypropane, 1,3-xylenyl radical, or a 1,4-xylenyl radical core group.