# US 2017/0283545 A1 · A method for improving fracture toughness of polyisocyanurate comprising reaction products

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- Number: US 2017/0283545 A1
- Document ID: US20170283545A1
- Status: Published application
- Kind: A1
- Application number: 15/505,771
- Filed: 2015-07-09
- Published: 2017-10-05
- Earliest claimed: 2014-09-05
- Assignees: Huntsman International LLC
- Applicants: Huntsman International LLC
- Inventors: Steve Andre Woulters
- Web page: https://patentgrep.com/patent/US20170283545A1

## CPC

- C08G 18/092: {oligomerisation to isocyanurate groups}
- C08G 18/022: {the polymeric products containing isocyanurate groups}
- C08G 18/225: {of alkali or alkaline earth metals}
- C08G 18/4045: {Mixtures of compounds of group C08G18/58 with other macromolecular compounds}
- C08G 18/4072: {Mixtures of compounds of group C08G18/63 with other macromolecular compounds}
- C08G 18/4213: {from terephthalic acid and dialcohols}
- C08G 18/4825: {Polyethers containing two hydroxy groups (C08G18/4833 - C08G18/5096 take precedence)}
- C08G 18/58: Epoxy resins {(C08G18/42, C08G18/48 take precedence; reaction products of epoxy resins with at least equivalent amounts of compounds containing active hydrogen C08G18/6407, with at least equivalent amounts of amines C08G18/6415; polymeric products of isocyanates or isothiocyanates with epoxy compounds having no active hydrogen C08G18/003)}
- C08G 18/638: {characterised by the use of compounds having carbon-to-carbon double bonds other than styrene and/or olefinic nitriles}
- C08G 18/7664: {containing alkylene polyphenyl groups}
- C08G 18/7671: {containing only one alkylene bisphenyl group}
- C08G 18/791: {containing isocyanurate groups}
- C08G 18/794: {formed by oligomerisation of aromatic isocyanates or isothiocyanates}
- C08L 75/08: from polyethers
- C08G 18/04: with vinyl compounds
- C08L 33/14: of esters containing halogen, nitrogen, sulfur, or oxygen atoms in addition to the carboxy oxygen
- C08L 2205/03: containing three or more polymers in a blend
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06)

## Abstract

A curable composition for making polyisocyanurate comprising products obtained by combining and mixing at an isocyanate index of at least 100 at least a polyisocyanate composition, an isocyanate reactive composition comprising at least 50 mol % diols and a toughening agent comprising acrylic block copolymers.

## Claims

### Claim 1

A curable composition for making polyisocyanurate comprising products, obtained by combining and mixing at an isocyanate index of at least 100:
a) A polyisocyanate composition,
b) An isocyanate reactive composition comprising at least 50 mol %, preferably at least 70 mol %, more preferably at least 90 mol % diols calculated on the total number of mol isocyanate reactive compounds in the isocyanate-reactive composition,
c) A toughening agent comprising acrylic block copolymers,
d) A trimerization catalyst composition, and
e) Optionally further additives and/or auxiliary compounds,
wherein the amount of polyisocyanates in the curable composition comprises at least 50 wt % polyisocyanates calculated on the total weight of the reactive curable composition.

### Claim 2 (depends on 1)

The curable composition according to claim 1, wherein the amount of polyisocyanates in the curable composition comprises at least 60 wt % polyisocyanates calculated on the total weight of the reactive curable composition.

### Claim 3 (depends on 1)

The curable composition according to claim 1, wherein the isocyanate-reactive composition comprises aromatic polyols, aromatic polyester polyols, aromatic polyester diols, and mixtures thereof.

### Claim 4 (depends on 1)

The curable composition according to claim 1, wherein the diols have a molecular weight (MW) below 1000 g/mol and comprise alkylene glycols and/or oxyalkylene glycols corresponding to the formula CnH2n(OH)2 and CnH2nO(OH)2.

### Claim 5 (depends on 1)

The curable composition according to claim 1, wherein the diols are selected from polyethylene glycol and/or polypropylene glycol-(1,2) and -(1,3), polybutylene glycol-(1,4) and -(2,3), polyhexanediol-(1,6), polyoctanediol-(1,8) and mixtures thereof.

### Claim 6 (depends on 1)

The curable composition according to claim 1, wherein the block copolymer toughening agent is a self assembling block copolymer wherein at least one block is a polyisocyanate/polyisocyanurate miscible block having a glass transition temperature (Tg) above 100° C. and at least one block is a polyisocyanate/polyisocyanurate immiscible block having a Tg below 0° C., and wherein the copolymer is present in the curable composition in a range from 0.1 wt % to 30 wt %, based on the total weight of the curable composition.

### Claim 7 (depends on 1)

The curable composition according to claim 1, wherein the block copolymer toughening agent is a self assembling block copolymer having a number average molecular weight (MW) of at least 1000 g/mol.

### Claim 8 (depends on 1)

The curable composition according to claim 1, wherein the polyisocyanate/polyisocyanurate miscible block of the block copolymer is selected from polymethylmetacrylate (Tg=105° C.) and/or polystyrene (Tg=100° C.) and the polyisocyanate/polyisocyanurate immiscible block of the block copolymer is selected from polyalkylacrylates and/or polydienes.

### Claim 9 (depends on 1)

The curable composition according to claim 1, wherein the polyisocyanates are selected from aliphatic, cycloaliphatic, araliphatic and aromatic polyisocyanates.

### Claim 10 (depends on 1)

The curable composition according to claim 1, wherein the trimerisation catalyst composition is selected from alkali and/or earth alkali metal salts of organic carboxylic acids.

### Claim 11 (depends on 1)

The curable composition according to claim 1, wherein the trimerisation catalyst composition is selected from a composition containing a lithium halide an epoxy resin and optionally a urea compound.

### Claim 12 (depends on 1)

The curable composition according to claim 1, wherein the trimerisation catalyst composition is used in a quantity of from 0.001 to 10 wt %, calculated on the total weight of the curable composition.

### Claim 13 (depends on 1)

The curable composition according to claim 1, wherein the auxiliary compounds are selected from non-isocyanate-reactive solvents, surfactants, scavengers, antimicrobial agents, fire retardants, smoke suppressants, UV-stabilizers, colorants, plasticizers, internal mould release agents, rheology modifiers, wetting agents, dispersing agents and fillers.

### Claim 14 (depends on 1)

The curable composition according to claim 1, wherein the auxiliary compounds comprise filler materials which are selected from wood chips, wood dust, wood flakes, wooden plates; paper and cardboard; sand, vermiculite, clay, cement and other silicates; ground rubber, ground thermoplastics, ground thermoset materials; cork in particulate form or in layers; natural fibers, like flax, hemp and sisal fibers; synthetic fibers; mineral fibers; mineral fillers; nanoparticles; glass beads, ground glass, hollow glass beads; expanded or expandable beads; untreated or treated waste; woven and non-woven textiles; and combinations of two or more of these materials.

### Claim 15 (depends on 1)

A process for making the curable composition according to claim 1, which comprises combining and mixing the ingredients (a) to (e) at ambient pressure and at a temperature between 5° C. and 45° C. and more preferably between 5° C. and 30° C.

### Claim 16 (depends on 1)

A method for making a polyisocyanurate comprising materials with improved toughness, said method comprises at least the steps of allowing the curable composition according to claim 1, to react at an isocyanate index of at least 100 and at a curing temperature above 50° C.

### Claim 17 (depends on 16)

The method for making polyisocyanurate comprising materials according to claim 16 wherein said method is a batch-wise, semi-continuously or continuously process, an injection-, an extrusion-, a pultrusion process or moulding process such as a compression moulding process, a resin transfer moulding process, a vacuum assisted moulding process, a resin infusion moulding process, a prepregging process.

### Claim 18 (depends on 16)

The method for making polyisocyanurate comprising materials according to claim 16, wherein the isocyanate index is in the range 100 up to 15000.

### Claim 19 (depends on 16)

The method for making polyisocyanurate comprising materials according to claim 16, wherein the curing temperature is between 50° C. and 350° C.

### Claim 20 (depends on 16)

A polyisocyanurate comprising material obtained by the method according to claim 16, having a glass transition temperature >100° C., a fracture toughness value G1c>1000 J/m2 and/or toughness value K1c>2 MPa·m1/2.

### Claim 21 (depends on 16)

A polyisocyanurate comprising material obtained by the method according to claim 16, having a glass transition temperature >150° C., a toughness value G1c>500 J/m2, and/or a toughness value K1c>1 MPa·m1/2.