# US 9,518,144 B2 · Masked polyisocyanate and uses thereof

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- Number: US 9,518,144 B2
- Document ID: US9518144B2
- Status: Granted
- Kind: B2
- Application number: 14/352,027
- Filed: 2012-10-18
- Published: 2014-08-28
- Granted: 2016-12-13
- Earliest claimed: 2011-10-20
- Assignees: Soprema
- Applicants: Soprema
- Inventors: Louis Durot; Pierre-Etienne Bindschedler; Virginie Francois Barseghian; Remi Perrin
- Web page: https://patentgrep.com/patent/US9518144B2

## CPC

- C08G 18/6415: {having nitrogen}
- C07C 265/14: containing at least two isocyanate groups bound to the same carbon skeleton
- C07C 271/20: to carbon atoms of hydrocarbon radicals substituted by nitrogen atoms not being part of nitro or nitroso groups
- C07C 271/28: to a carbon atom of a non-condensed six-membered aromatic ring
- C08G 18/80: Masked polyisocyanates
- C08L 95/00: Compositions of bituminous materials, e.g. asphalt, tar, pitch
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06)

## Abstract

The invention relates to polyurethane resin compositions and, in particular, stable, ready-to-use polyurethane resin compositions comprising: a masked polyisocyanate having formula (I), wherein B represents alkyl and A represents a group comprising a number of isocyanate functions of between 1.5 and 2.2, preferably between 1.5 and 2.1 and, more preferably, between 1.5 and 2; or a masked pre-polymer that is the product of a reaction between the above-mentioned masked polyisocyanate and a polyol having between 1.5 and 3 OH functions and a molecular mass of between 900 and 3,000 g/mol, in a ratio such that the number of NCO functions of the masked polyisocyanate in relation to the number of OH functions of the polyol is between 1.5 and 2.5 approximately; or a mixture of the aforementioned masked polyisocyanate and masked pre-polymer. The invention also relates to the use of the masked polyisocyanate in order to form a masked pre-polymer by reacting said masked polyisocyanate on a polyol, and to the use of a masked polyisocyanate and/or a masked pre-polymer in polyurethane resin compositions.

## Claims

### Claim 1

A stable, liquid polyurethane composition which comprises:
at least one masked polyisocyanate corresponding to the following formula:
wherein:
B represents alkyl,
A represents a group comprising a number of isocyanate functions between 1.5 and 2.2;
at least one prepolymer which is the reaction product of polyol or of a mixture of polyols containing a number of OH functions between 1.5 and 3 with a polyisocyanate or a mixture of polyisocyanates containing a number of NCO functions between 1.6 and 3, in a ratio such that the number of NCO functions of the polyisocyanate or of the polyisocyanate mixture relative to the number of OH functions of the polyol or mixture of polyols is from 1.5 to 2.5 approximately;
optionally a plasticizer;
optionally a catalyst;
optionally solvent and/or diluent;
optionally a filler.

### Claim 2

A stable, liquid polyurethane composition which comprises:
at least one masked prepolymer formed by reaction between:
a polyol containing between 1.5 and 3 OH functions and having a molecular weight between 900 and 3,000 g/mol; and
a masked polyisocyanate corresponding to the following formula
wherein:
B represents alkyl,
A represents a group comprising a number of isocyanate functions between 1.5 and 2.2;
in a ratio such that the number of NCO functions of the masked polyisocyanate relative to the number of OH functions of the polyol or mixture of polyols is from 1.5 to 2.5 approximately;
optionally a polyisocyanate containing between 1.5 and 3 NCO functions;
optionally a plasticizer;
optionally a catalyst;
optionally solvent and/or diluent.

### Claim 3 (depends on 2)

The stable, liquid polyurethane composition according to claim 2, further comprising a masked polyisocyanate corresponding to the following formula:
wherein:
B represents alkyl,
A represents a group comprising a number of isocyanate functions between 1.5 and 2.2.

### Claim 4 (depends on 1)

The stable, liquid polyurethane composition according to claim 1, wherein said composition comprises less than 5% by weight of free diisocyanate monomers.

### Claim 5 (depends on 2)

The stable, liquid polyurethane composition according to claim 2, wherein the polyol used to form the masked prepolymer is a polyether, polyester, polybutadiene or polycarbonate type polyol, and mixtures thereof.

### Claim 6 (depends on 2)

The stable, liquid polyurethane composition according to claim 2, wherein the polyol is a polytetrahydrofuran, a 1,6-hexanediol polycarbonate, a polyester of fatty acid dimers comprising 34 to 36 carbon atoms, a polycaprolactone or a hydroxylated polybutadiene.

### Claim 7 (depends on 1)

The stable, liquid polyurethane composition according to claim 1, wherein B represents an optionally unsaturated C2-C20 alkyl.

### Claim 8 (depends on 1)

The stable, liquid polyurethane composition according to claim 1, wherein the “group” of A is:
a polymer chain (originating from a polymeric MDI) corresponding to formula (A1):
a radical corresponding to formula (A2) or to a related radical of a TDI trimer:
a radical corresponding to one of the formulae (A3) and/or (A4) or to a related radical of an HDI trimer:
a radical corresponding to formula (A5) or to a related radical of an IPDI trimer:
wherein each dashed line represents a point of attachment to a NCO function or to the group —NHCOO—B of the masked polyisocyanate and on condition that there is at least one dashed line that is a point of attachment to the group —NHCOO—B and that the remaining lines represent a point of attachment to a NCO function.

### Claim 9 (depends on 1)

A process for the preparation of a stable, liquid polyurethane resin composition comprising introducing the masked polyisocyanate according to claim 1 in said stable, liquid polyurethane resin composition.

### Claim 10 (depends on 2)

The stable, liquid polyurethane composition according to claim 2, wherein said composition comprises less than 5% by weight of free diisocyanate monomers.

### Claim 11 (depends on 2)

The stable, liquid polyurethane composition according to claim 2, wherein B represents an optionally unsaturated C2-C20 alkyl.

### Claim 12 (depends on 2)

The stable, liquid polyurethane composition according to claim 2, wherein the “group” of A is:
a polymer chain (originating from a polymeric MDI) corresponding to formula (A1):
a radical corresponding to formula (A2) or to a related radical of a TDI trimer:
a radical corresponding to one of the formulae (A3) and/or (A4) or to a related radical of an HDI trimer:
a radical corresponding to formula (A5) or to a related radical of an IPDI trimer:
wherein each dashed line represents a point of attachment to a NCO function or to the group —NHCOO—B of the masked polyisocyanate and on condition that there is at least one dashed line that is a point of attachment to the group —NHCOO—B and that the remaining lines represent a point of attachment to a NCO function.

### Claim 13 (depends on 2)

A process for the preparation of a stable, liquid polyurethane resin composition comprising introducing the masked prepolymer according to claim 2 in said stable, liquid polyurethane resin composition.