(Meth)acrylate-functionalized extended isosorbide

Patent metadata

Field	Value
Publication number	US-12428518-B2
Application number	US-201715723583-A
Country	US
Kind code	B2
Filing date	Oct 3, 2017
Priority date	Apr 3, 2015
Publication date	Sep 30, 2025
Grant date	Sep 30, 2025

Abstract

The present invention relates to curable polyurethane polymers made from renewable materials. In particular isosorbide derived from glucose is used. These renewable materials may be formed into curable polyurethane polymer compositions having different chemical functionalities and cure mechanisms.

First claim

The invention claimed is:

1. An anaerobically curable composition comprising
a (meth)acrylate component, an isosorbide diurethane (meth)acrylate, and
an anaerobic cure system;
wherein the isosorbide diurethane (meth)acrylate is the reaction product of an isosorbide and 2-isocyanatoethyl (meth)acrylate;
wherein the (meth)acrylate component is selected from the group consisting of 2-hydroxyethyl methacrylate, 2-hydroxyethyl acrylate, 3-hydroxypropyl methacrylate, 3-hydroxypropyl acrylate, 2-hydroxypropyl acrylate, 4-hydroxybutyl acrylate, 3-hydroxybutyl acrylate, 2-hydroxybutyl acrylate, 3-(acryloyloxy)-2-hydroxypropyl methacrylate, 2-isocyanatoethyl methacrylate, 2-isocyanatoethyl acrylate, poly(propylene glycol) (meth)acrylate, 2-isocyanatoethyl acrylate, 2-isocyanatoethyl methacrylate, 3-isocyanatopropyl (meth)acrylate, 2-isocyanatopropyl (meth)acrylate, 4-isocyanatobutyl (meth)acrylate, 3-isocyanatobutyl (meth)acrylate, and 2-isocyanatobutyl (meth)acrylate; and
wherein the (meth)acrylate component is present in an amount of 85 wt % and the isosorbide diurethane (meth)acrylate is present in an amount of 10 wt %, each based on the total weight of the composition, and wherein said composition after curing for 168 hours has a break torque of from 25 N·m to 30 N·m on black oxide nuts and bolts; or
wherein the (meth)acrylate component is present in an amount of 80 wt % and the isosorbide diurethane (meth)acrylate is present in an amount of 15 wt %, each based on the total weight of the composition, and wherein said composition after curing for 168 hours, has a break torque of from 30 N·m to 40 N·m on black oxide nuts and bolts; or
wherein the (meth)acrylate component is present in an amount of 75 wt % and the isosorbide diurethane (meth)acrylate is present in an amount of 20 wt %, each based on the total weight of the composition, and wherein said composition after curing has a break torque of from 30 N·m to 40 N·m on pre-torqued zinc phosphate nuts and bolts at a temperature of 150° C. or at a temperature of 180° C.; or
wherein the (meth)acrylate component is present in an amount of 70 wt % and the isosorbide diurethane (meth)acrylate is present in an amount of 25 wt %, each based on the total weight of the composition, and wherein said composition after curing has a break torque of from 40 N·m to 50 N·m on pre-torqued zinc phosphate nuts and bolts at a temperature of 150° C. or at a temperature of 180° C.

2. The composition of claim 1 , wherein the composition further includes a metal-based catalyst.

3. The anaerobically curable composition of claim 1 , wherein the (meth)acrylate component is present in an amount of 80 wt % and the isosorbide diurethane (meth)acrylate is present in an amount of 15 wt %, each based on the total weight of the composition, and wherein said composition after curing for 168 hours, has a break torque of from 30 N·m to 40 N·m on black oxide nuts and bolts.

4. The anaerobically curable composition of claim 1 , wherein the (meth)acrylate component is present in an amount of 70 wt % and the isosorbide diurethane (meth)acrylate is present in an amount of 25 wt %, each based on the total weight of the composition, and wherein said composition after curing has a break torque of from 40 N·m to 50 N·m on pre-torqued zinc phosphate nuts and bolts at a temperature of 150° C. or at a temperature of 180° C.

5. The anaerobically curable composition of claim 1 , wherein the (meth)acrylate component is present in an amount of 85 wt % and the isosorbide diurethane (meth)acrylate is present in an amount of 10 wt %, each based on the total weight of the composition, and wherein said composition after curing for 168 hours has a break torque of from 25 N·m to 30 N·m on black oxide nuts and bolts.

6. The anaerobically curable composition of claim 1 , wherein the (meth)acrylate component is present in an amount of from 75 wt % and the isosorbide diurethane (meth)acrylate is present in an amount of 20 wt %, each based on the total weight of the composition, and wherein said composition after curing has a break torque of from 30 N·m to 40 N·m on pre-torqued zinc phosphate nuts and bolts at a temperature of 150° C. or at a temperature of 180° C.

7. An anaerobically curable composition comprising
a (meth)acrylate component, an isosorbide diurethane (meth)acrylate, and
an anaerobic cure system;
wherein the isosorbide diurethane (meth)acrylate is the reaction product of an isosorbide and an isocyanatoalkyl (meth)acrylate selected from the group consisting of 2-isocyanatoethyl (meth)acrylate, 3-isocyanatopropyl (meth)acrylate, 2-isocyanatopropyl (meth)acrylate, 4-isocyanatobutyl (meth)acrylate, 3-isocyanatobutyl (meth)acrylate, and 2-isocyanatobutyl (meth)acrylate;
wherein the (meth)acrylate component is selected from the group consisting of 2-hydroxyethyl methacrylate, 2-hydroxyethyl acrylate, 3-hydroxypropyl methacrylate, 3-hydroxypropyl acrylate, 2-hydroxypropyl acrylate, 4-hydroxybutyl acrylate, 3-hydroxybutyl acrylate, 2-hydroxybutyl acrylate, 3-(acryloyloxy)-2-hydroxypropyl methacrylate, 2-isocyanatoethyl methacrylate, 2-isocyanatoethyl acrylate, poly(propylene glycol) (meth)acrylate, 2-isocyanatoethyl acrylate, 2-isocyanatoethyl methacrylate, 3-isocyanatopropyl (meth)acrylate, 2-isocyanatopropyl (meth)acrylate, 4-isocyanatobutyl (meth)acrylate, 3-isocyanatobutyl (meth)acrylate, and 2-isocyanatobutyl (meth)acrylate; and
wherein the (meth)acrylate component is present in an amount of 85 wt % and the isosorbide diurethane (meth)acrylate is present in an amount of 10 wt %, each based on the total weight of the composition, and wherein said composition after curing for 168 hours has a break torque of from 25 N·m to 30 N·m on black oxide nuts and bolts; or
wherein the (meth)acrylate component is present in an amount of 80 wt % and the isosorbide diurethane (meth)acrylate is present in an amount of 15 wt %, each based on the total weight of the composition, and wherein said composition after curing for 168 hours, has a break torque of from 30 N·m to 40 N·m on black oxide nuts and bolts; or
wherein the (meth)acrylate component is present in an amount of 75 wt % and the isosorbide diurethane (meth)acrylate is present in an amount of 20 wt %, each based on the total weight of the composition, and wherein said composition after curing has a break torque of from 30 N·m to 40 N·m on pre-torqued zinc phosphate nuts and bolts at a temperature of 150° C. or at a temperature of 180° C.; or
wherein the (meth)acrylate component is present in an amount of 70 wt % and the isosorbide diurethane (meth)acrylate is present in an amount of 25 wt %, each based on the total weight of the composition, and wherein said composition after curing has a break torque of from 40 N·m to 50 N·m on pre-torqued zinc phosphate nuts and bolts at a temperature of 150° C. or at a temperature of 180° C.

8. The anaerobically curable composition of claim 7 , wherein the (meth)acrylate component is present in an amount of 80 wt % and the isosorbide diurethane (meth)acrylate is present in an amount of 15 wt %, each based on the total weight of the composition, and wherein said composition after curing for 168 hours, has a break torque of from 30 N·m to 40 N·m on black oxide nuts and bolts.

9. The anaerobically curable composition of claim 7 , wherein the (meth)acrylate component is present in an amount of 70 wt % and the isosorbide diurethane (meth)acrylate is present in an amount of 25 wt %, each based on the total weight of the composition, and wherein said composition after curing has a break torque of from 40 N·m to 50 N·m on pre-torqued zinc phosphate nuts and bolts at a temperature of 150° C. or at a temperature of 180° C.

10. The anaerobically curable comp

Assignees

• Henkel Ag & Co Kgaa

Inventors

• Dworak David P
• Gustafson Darel
• Mullen David
• Messana Andrew D
• Hynes Aimee
• Ledwith Deirdre
• O'Kane Ruairi

Classifications

• C08G81/024

  Block or graft polymers containing sequences of polymers of C08C or C08F and of polymers of C08G · CPC title

• C08G18/6225

  Polymers of esters of acrylic or methacrylic acid · CPC title

• C08G18/04

  with vinyl compounds · CPC title

• C08F222/102

  of dialcohols, e.g. ethylene glycol di(meth)acrylate or 1,4-butanediol dimethacrylate · CPC title

• C08F220/343

  in the form of urethane links · CPC title