Reactive flame retardants for polyurethane and polyisocyanurate foams
AssigneeICL-IP America Inc.
InventorsJoseph Zilberman, Andrew Piotrowski, Eran Gluz, Jeffrey Stowell, Mark Gelmont, Zhihao Chen, Mayank Singh
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Abstract
The present invention provides novel cyclic phosphorus-containing compounds, namely hydroxyl-functional phospholene-1-oxides, serving as highly efficient reactive flame retardants in urethane systems, particularly in flexible polyurethane foams, semi-rigid and rigid polyurethane and polyisocyanurate foams. The invention further provides fire-retarded polyurethane compositions comprising said hydroxyl-functional phospholene-1-oxides.
Claims15
A flexible polyurethane or polyisocyanurate comprising a hydroxyl-functional phospholene-1-oxide compound of the formula (I-A):
- wherein:
- the dashed line indicates a double bond located between the carbon atom at position 3 and one of the carbon atoms at positions 2 and 4, provided that each of the two ring carbon atoms which are not part of the double bond are each bonded to one of the two hydrogen atoms shown in the structural formula (I-A);
- R1, R2, R3 and R4 are independently selected from H, a linear or branched alkyl group containing from 1 to 4 carbon atoms, or chlorine;
- and,
- X is either
- and when X is - - - - - - (Z)k—R7, Z is —(Y—O)n—, wherein Y is a linear or branched alkylene group containing from 2 to 8 carbon atoms and n represents an integer from 1 to 20;
- k may be 0 or 1;
- R7 is selected from hydrogen, a hydroxy-terminated linear or branched alkylene group containing from 2 to about 8 carbon atoms;
- and,
- provided that when k is zero, R7 is the hydroxy-terminated linear or branched alkylene group and when k is 1, R7 is hydrogen, and
- when X is
- R5 and R6 are each independently selected from H, a linear or branched alkyl group containing from 1 to 8 carbon atoms, a linear or branched alkenyl group containing from 2 to 8 carbon atoms, a hydroxyalkyl group containing from 2 to 4 carbon atoms, a halo-substituted alkyl group containing from 1 to 8 carbon atoms, an alkoxy group containing from 1 to 8 carbon atoms, an aryl group containing from 6 to 12 carbon atoms and an alkylaryl group containing from 7 to 16 carbon atoms, or R5 and R6 are bonded to each other to form a cycloalkyl group containing from 5 to about 8 carbon atoms.
A flexible polyurethane or polyisocyanurate comprising a phosphorus-containing polyol reaction product of the partial phosphorylation of a polyalcohol, which comprises at least one phosphorus-containing group, of the formula (I-B):
- wherein:
- the dashed line indicates a double bond located between the carbon atom at position 3 and one of the carbon atoms at positions 2 and 4, provided that each of the two ring carbon atoms which are not part of the double bond are each bonded to one of the two hydrogen atoms shown in the structural formula (I-B);
- R1, R2, R3 and R4 are independently selected from H, a linear or branched alkyl group containing from 1 to 4 carbon atoms, or chlorine,
- each of n1 and n2 is an integer equal to or greater than 1, with n1+n2 being equal to or greater than 3, and
- Z2 is a moiety derived from a branched polyol which has a valence of n1+n2, and is of the general formula:
- wherein R is selected from the group consisting of:
- and where each R8 independently is H or is an alkyl of from 1 to 4 carbon atoms, x is ≥1, y is 2 or 3;
- z is an integer of from 2 to 5;
- and, m≥1.
A flexible polyurethane or polyisocyanurate foam comprising the reaction product of a polyol, a polyisocyanate and a hydroxyl-functional phospholene-1-oxide compound of the formula (I-A):
- wherein:
- the dashed line indicates a double bond located between the carbon atom at position 3 and one of the carbon atoms at positions 2 and 4, provided that each of the two ring carbon atoms which are not part of the double bond are each bonded to one of the two hydrogen atoms shown in the structural formula (I-A);
- R1, R2, R3 and R4 are independently selected from H, a linear or branched alkyl group containing from 1 to 4 carbon atoms, or chlorine;
- and,
- X is either
- and when X is - - - - - - (Z)k—R7, Z is —(Y—O)n—, wherein Y is a linear or branched alkylene group containing from 2 to 8 carbon atoms and n represents an integer from 1 to 20;
- k may be 0 or 1;
- R7 is selected from hydrogen, a hydroxy-terminated linear or branched alkylene group containing from 2 to about 8 carbon atoms;
- and,
- provided that when k is zero, R7 is the hydroxy-terminated linear or branched alkylene group and when k is 1, R7 is hydrogen, and
- when X is
- R5 and R6 are each independently selected from H, a linear or branched alkyl group containing from 1 to 8 carbon atoms, a linear or branched alkenyl group containing from 2 to 8 carbon atoms, a hydroxyalkyl group containing from 2 to 4 carbon atoms, a halo-substituted alkyl group containing from 1 to 8 carbon atoms, an alkoxy group containing from 1 to 8 carbon atoms, an aryl group containing from 6 to 12 carbon atoms and an alkylaryl group containing from 7 to 16 carbon atoms, or R5 and R6 are bonded to each other to form a cycloalkyl group containing from 5 to about 8 carbon atoms.
A flexible polyurethane or polyisocyanurate foam comprising the reaction product of a polyol, a polyisocyanate and a phosphorus-containing polyol reaction product of the partial phosphorylation of a polyalcohol, which comprises at least one phosphorus-containing group, of the formula (I-B):
- wherein:
- the dashed line indicates a double bond located between the carbon atom at position 3 and one of the carbon atoms at positions 2 and 4, provided that each of the two ring carbon atoms which are not part of the double bond are each bonded to one of the two hydrogen atoms shown in the structural formula (I-B);
- R1, R2, R3 and R4 are independently selected from H, a linear or branched alkyl group containing from 1 to 4 carbon atoms, or chlorine,
- each of n1 and n2 is an integer equal to or greater than 1, with n1+n2 being equal to or greater than 3, and
- Z2 is a moiety derived from a branched polyol which has a valence of n1+n2, and is of the general formula:
- wherein R is selected from the group consisting of:
- and where each R8 independently is H or is an alkyl of from 1 to 4 carbon atoms, x is ≥1, y is 2 or 3;
- z is an integer of from 2 to 5;
- and, m≥1.
Dependencies are inferred from the claim text.