# US 2018/0022848 A1 · (meth)acrylate-functionalized extended isosorbide

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- Number: US 2018/0022848 A1
- Document ID: US20180022848A1
- Status: Published application
- Kind: A1
- Application number: 15/723,583
- Filed: 2017-10-03
- Published: 2018-01-25
- Earliest claimed: 2015-04-03
- Assignees: Henkel IP & Holding GmbH
- Applicants: Henkel IP & Holding GmbH
- Inventors: David P. Dworak; Darel Gustafson; David Mullen; Andrew D. Messana; Aimee Hynes; Deirdre Ledwith; Ruairi O'Kane
- Web page: https://patentgrep.com/patent/US20180022848A1

## CPC

- C08G 18/3218: {containing cyclic groups having at least one oxygen atom in the ring}
- C07D 493/04: Ortho-condensed systems
- C08F 222/10: Esters
- C08F 299/065: {from polyurethanes with side or terminal unsaturations}
- C08G 18/04: with vinyl compounds
- C08G 18/6225: {Polymers of esters of acrylic or methacrylic acid}
- C08G 18/672: {Esters of acrylic or alkyl acrylic acid having only one group containing active hydrogen}
- C08G 18/755: {and at least one isocyanate or isothiocyanate group linked to a secondary carbon atom of the cycloaliphatic ring, e.g. isophorone diisocyanate}
- C08G 18/8016: {Masked aliphatic or cycloaliphatic polyisocyanates}
- C08G 18/8116: {esters of acrylic or alkylacrylic acid having only one isocyanate or isothiocyanate group}
- C08G 81/024: {Block or graft polymers containing sequences of polymers of C08C or C08F and of polymers of C08G}
- C08L 35/02: Homopolymers or copolymers of esters (C08L35/06, C08L35/08 take precedence)
- C09D 175/16: having terminal carbon-to-carbon unsaturated bonds
- C09J 175/16: having terminal carbon-to-carbon unsaturated bonds
- C08F 220/343: {in the form of urethane links}
- C08F 222/102: {of dialcohols, e.g. ethylene glycol di(meth)acrylate or 1,4-butanediol dimethacrylate}
- C08G 2190/00: Compositions for sealing or packing joints
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06)
- C09D: COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR (cosmetics A61K; processes for applying liquids or other fluent materials to surfaces, in general, B05D; staining wood B27K5/02; glazes or vitreous enamels C03C; natural resins, French polish, drying-oils, driers, turpentine, per se, C09F; polishing compositions other than French polish, ski waxes C09G; adhesives or use of materials as adhesives C09J; materials for sealing or packing joints or covers C09K3/10; materials for stopping leaks C09K3/12; processes for the electrolytic or electrophoretic production of coatings C25D)
- C09J: ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES (preparation of glue or gelatine C09H)

## 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.

## Claims

### Claim 1

A (meth)acrylate functionalized isosorbide corresponding to the structure:
MA-U-A-U-MA
wherein A comprises an isosorbide unit, U comprises a urethane linkage and MA comprises a member selected from the group consisting of a (meth)acrylate-containing group, an acrylate-containing group and combinations thereof.

### Claim 2 (depends on 1)

The (meth)acrylate functionalized isosorbide of claim 1, wherein the (meth)acrylate-containing group comprises a reactant residue 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.

### Claim 3 (depends on 1)

The (meth)acrylate functionalized isosorbide of claim 1, wherein the urethane linkage represented by U is comprised of a isocyanate reactant residue selected from the group consisting of isophorone diisocyanate (IPDI), IPDI isocyanaurate, polymeric IPDI, naphthalene 1,5-diisocyanate (NDI), methylene bis-cyclohexylisocyanate, methylene diphenyl diisocyanate (MDI), polymeric MDI, toluene diisocyanate (TDI), isocyanaurate of TDI, TDI-trimethylolpropane adduct, polymeric TDI, hexamethylene diisocyanate (HDI), HDI isocyanaurate, HDI biurate, polymeric HDI, xylylene diisocyanate, hydrogenated xylylene diisocyanate, tetramethyl xylylene diisocyanate, p-phenylene diisocyanate, 3,3′-dimethyldiphenyl-4,4′-diisocyanate (DDDI), 2,2,4-trimethylhexamethylene diisocyanate (TMDI), norbornane diisocyanate (NDI) and 4,4′-dibenzyl diisocyanate (DBDI).

### Claim 4 (depends on 1)

A curable composition comprising the (meth)acrylate functionalized isosorbide of claim 1 and a cure system.

### Claim 5 (depends on 4)

The curable composition of claim 4, wherein said cure system is selected from the group consisting of a free, radical initiator system, an anaerobic cure system, a heat cure system and combinations thereof.

### Claim 6 (depends on 4)

The curable composition of claim 4, further comprising a (meth)acrylate component.

### Claim 7 (depends on 6)

The curable composition of claim 6, 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.

### Claim 8

A method of forming a polyurethane polymer from a renewable source, said polyurethane polymer being (meth)acrylate functionalized, said method comprising:
a) forming a polyurethane polymer by reacting isosorbide with a diisocyanate;
b) reacting said polyurethane polymer with (i) a (meth)acrylate monomer containing hydroxyl functionality to yield said curable (meth)acrylate-funtionalized polyurethane polymer.

### Claim 9 (depends on 8)

The method of claim 8, wherein the ratios of OH/NCO equivalents are form 0.1 to 10.0.

### Claim 10 (depends on 9)

The method of claim 9, wherein the reaction is carried out until substantially all NCO groups are reacted with OH groups.

### Claim 11 (depends on 8)

The method of claim 8, wherein the reaction further includes a metal-based catalyst.

### Claim 12

A polymerizable resin comprising:
a) polymer corresponding to the structure:
MA-U-A-U-MA
wherein A comprises isosobide unit, U comprises a urethane linkage and MA comprises a (meth)acrylate-containing group;
b) a cure system selected from the group consisting of a free radical initiator system.

### Claim 13

A method for forming a polymerizable (meth)acrylate-functionalized polyurethane polymer comprising, reacting a (meth)acrylate-functionalized isocyanate compound with an isosorbide unit, said reacting being conducted for a time and at a temperature sufficient to form a polymerizable (meth)acrylate-functionalized polyurethane compound.

### Claim 14 (depends on 13)

The method of claim 13, wherein the reacting is carried out at temperatures of about 25° C. to 100° C. for about 2 to about 24 hours.

### Claim 15 (depends on 14)

The method of claim 14, wherein the (meth)acrylate-functionalized isocyanate compound is selected from the consisting of 2-methacryloyloxethyl isocyanate and 2-acryloyloxethyl isocyanate.

### Claim 16 (depends on 13)

The method of claim 13, comprising the reaction scheme:

### Claim 17 (depends on 8)

The method of claim 8, comprising the reaction scheme: