US 5,401,824 AGranted

Storage stable isocyanate-reactive compositions for use in flame-retardant systems

AssigneeMiles Inc.

InventorsJan L. R. Clatty, Michael T. Wellman, Sanjeev Madan

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Abstract

This invention relates to stabilizing isocyanate-reactive compositions containing flame retardants by the use of certain tertiary amines or ammonium compounds, in which said stabilized compositions are prepared by mixing (a) at least one isocyanate-reactive compound having a molecular weight of 400 to 10,000 and a functionality of 2 to 7; (b) at least one isocyanate-reactive compound having a molecular weight of less than 399 and a functionality of 2 to 6; (c) at least one (i) isocyanate-reactive tertiary amine polyether, (ii) fatty amido-amine, and/or (iii) ammonium salt derivative of a fatty amido-amine; (d) a flame retardant; (e) a catalyst; and (f) optional additives. This invention also relates to urethane-based products prepared by reaction of organic polyisocyanates with such compositions.

Claims13

Dependent claims

A polyurethane containing a flame retardant prepared by the isocyanate addition reaction, at an isocyanate index of from 80 to 130 in the absence of a blowing agent, of an organic polyisocyanate with a storage-stable isocyanate-reactive composition comprising

(a) 10 to 90 percent by weight, based on the total of components (a), (b), (c), (d), and (e), of at least one isocyanate-reactive compound having a molecular weight of 400 to 10,000 and a functionality of 2 to 7;
(b) 0.6 to 67 percent by weight, based on the total of components (a), (b), (c), (d), and (e), of at least one isocyanate-reactive compound having a molecular weight of less than 399 and a functionality of 2 to 6;
(c) 0.7 to 30 percent by weight, based on the total of components (a), (b), (c), (d), and (e), of a tertiary amine or ammonium compound selected from the group consisting of
(i) an isocyanate-reactive tertiary amine polyether having a molecular weight of from 100 to 1000 and having the formula
R[NR.sup.1 R.sup.2 ].sub.m
wherein
R is saturated or unsaturated C.sub.2 -C.sub.8 aliphatic or C.sub.2 -C.sub.8 aliphatic substituted with --OH,--SH, or NHR.sup.a wherein R.sup.a is C.sub.1 -C.sub.8 alkyl or C.sub.2 -C.sub.8 alkenyl;
saturated or unsaturated C.sub.5 -C.sub.8 cycloaliphatic or C.sub.5 -C.sub.8 cycloaliphatic substituted with C.sub.1 -C.sub.8 alkyl, C.sub.2 -C.sub.8 alkenyl, C.sub.1 -C.sub.8 alkylene, --OH, --SH, or NHR.sup.a wherein R.sup.a is alkyl or alkenyl;
or five- or six-membered aromatic or heteroaromatic optionally substituted with C.sub.1 -C.sub.8 alkyl, C.sub.1 -C.sub.8 alkoxy, halogen, cyano, nitro, C.sub.1 -C.sub.8 alkylene, --OH, --SH, or NHR.sup.a wherein R.sup.a is C.sub.1 -C.sub.8 alkyl or C.sub.2 -C.sub.8 alkenyl;
R.sup.1 and R.sup.2 are independently polyether groups terminated with isocyanate-reactive groups selected from --OH, --SH, and NHR.sup.b wherein R.sup.b is C.sub.1 -C.sub.8 alkyl or C.sub.2 -C.sub.8 alkenyl;
and
m is an integer of from 1 to 4;
(ii) a fatty amido-amine;
(iii) an ammonium salt derivative of a fatty amido-amine;
and
(iv) mixtures thereof;
(d) 5 to 55 percent by weight, based on the total of components (a), (b), (c), (d), and (e), of a flame retardant;
(e) 0.007 to 6 percent by weight, based on the total of components (a), (b), (c), (d), and (e), of a catalyst selected from tertiary amines, organic metal compounds, and mixtures thereof;
and
(f) 0 to 15 percent by weight, based on the total of components (a), (b), (c), (d), and ( e ), of additives.

17 more elements

A rigid non-microcellular urethane-based product containing a flame retardant prepared by the isocyanate addition reaction, at an isocyanate index of from 100 to 120 in the absence of a blowing agent, of an organic polyisocyanate with a storage-stable isocyanate-reactive composition comprising

(a) 18 to 57 percent by weight, based on the total of components (a), (b), (c), (d), and (e), of at least one isocyanate-reactive compound having a molecular weight of 400 to 10,000 and a functionality of 2 to 7;
(b) 28 to 67 percent by weight, based on the total of components (a), (b), (c), (d), and (e), of at least one isocyanate-reactive compound having a molecular weight of less than 399 and a functionality of 2 to 6;
(c) 1.4 to 27 percent by weight, based on the total of components (a), (b), (c), (d), and (e), of a tertiary amine or ammonium compound selected from the group consisting of
(i) an isocyanate-reactive tertiary amine polyether having a molecular weight of from 100 to 1000 and having the formula
R[NR.sup.1 R.sup.2 ].sub.m
wherein
R is saturated or unsaturated C.sub.2 -C.sub.8 aliphatic or C.sub.2 -C.sub.8 aliphatic substituted with --OH, --SH, or NHR.sup.a wherein R.sup.a is C.sub.1 -C.sub.8 alkyl or C.sub.2 -C.sub.8 alkenyl;
saturated or unsaturated C.sub.5 -C.sub.8 cycloaliphatic or C.sub.5 -C.sub.8 cycloaliphatic substituted with C.sub.1 -C.sub.8 alkyl, C.sub.2 -C.sub.8 alkenyl, C.sub.1 -C.sub.8 alkylene, --OH, --SH, or NHR.sup.a wherein R.sup.a is alkyl or alkenyl;
or five- or six-membered aromatic or heteroaromatic optionally substituted with C.sub.1 -C.sub.8 alkyl, C.sub.1 -C.sub.8 alkoxy, halogen, cyano, nitro, C.sub.1 -C.sub.8 alkylene, --OH, --SH, or NHR.sup.a wherein R.sup.a is C.sub.1 -C.sub.8 alkyl or C.sub.2 -C.sub.8 alkenyl;
R.sup.1 and R.sup.2 are independently polyether groups terminated with isocyanate-reactive groups selected from --OH, --SH, and NHR.sup.b wherein R.sup.b is C.sub.1 -C.sub.8 alkyl or C.sub.2 -C.sub.8 alkenyl;
and
m is an integer of from 1 to 4;
(ii) a fatty amido-amine;
(iii) an ammonium salt derivative of a fatty amido-amine;
and
(iv) mixtures thereof;
(d) 10 to 38 percent by weight, based on the total of components (a), (b), (c), (d), and (e), of a flame retardant;
p1 (e) 0.07 to 3.5 percent by weight, based on the total of components (a), (b), (c), (d), and (e), of a catalyst selected from tertiary amines, organic metal compounds, and mixtures thereof;
and
(f) 0 to 15 percent by weight, based on the total of components (a), (b), (c), (d), and (e), of additives.

17 more elements

A non-microcellular urethane-based elastomer containing a flame retardant prepared by the isocyanate addition reaction, at an isocyanate index of from 90 to 110 in the absence of a blowing agent, of an organic polyisocyanate with a storage-stable isocyanate-reactive composition comprising

(a) 32 to 90 percent by weight, based on the total of components (a), (b), (c), (d), and (e), of at least one isocyanate-reactive compound having a molecular weight of 400 to 10,000 and a functionality of 2 to 7;
(b) 0.7 to 38 percent by weight, based on the total of components (a), (b), (c), (d), and (e), of at least one isocyanate-reactive compound having a molecular weight of less than 399 and a functionality of 2 to 6;
(c) 1.4 to 27 percent by weight, based on the total of components (a), (b), (c), (d), and (e), of a tertiary amine or ammonium compound selected from the group consisting of
(i) an isocyanate-reactive tertiary amine polyether having a molecular weight of from 100 to 1000 and having the formula
R[NR.sup.1 R.sup.2 ].sub.m
wherein
R is saturated or unsaturated C.sub.2 -C.sub.8 aliphatic or C.sub.2 -C.sub.8 aliphatic substituted with --OH, --SH, or NHR.sup.a wherein R.sup.a is C.sub.1 -C.sub.8 alkyl or C.sub.2 -C.sub.8 alkenyl;
saturated or unsaturated C.sub.5 -C.sub.8 cycloaliphatic or C.sub.5 -C.sub.8 cycloaliphatic substituted with C.sub.1 -C.sub.8 alkyl, C.sub.2 -C.sub.8 alkenyl, C.sub.1 -C.sub.8 alkylene, --OH, --SH, or NHR.sup.a wherein R.sup.a is alkyl or alkenyl;
or five- or six-membered aromatic or heteroaromatic optionally substituted with C.sub.1 -C.sub.8 alkyl, C.sub.1 -C.sub.8 alkoxy, halogen, cyano, nitro, C.sub.1 -C.sub.8 alkylene, --OH, --SH, or NHR.sup.a wherein R.sup.a is C.sub.1 -C.sub.8 alkyl or C.sub.2 -C.sub.8 alkenyl;
R.sup.1 and R.sup.2 are independently polyether groups terminated with isocyanate-reactive groups selected from --OH, --SH, and NHR.sup.b wherein R.sup.b is C.sub.1 -C.sub.8 alkyl or C.sub.2 -C.sub.8 alkenyl;
and
m is an integer of from 1 to 4;
(ii) a fatty amido-amine;
(iii) an ammonium salt derivative of a fatty amido-amine;
and
(iv) mixtures thereof;
(d) 20 to 48 percent by weight, based on the total of components (a), (b), (c), (d), and (e), of a flame retardant;
(e) 0.07 to 3.5 percent by weight, based on the total of components (a), (b), (c), (d), and (e), of a catalyst selected from tertiary amines, organic metal compounds, and mixtures thereof;
and
(f) 0 to 15 percent by weight, based on the total of components (a), (b), (c), (d), and (e), of additives.

17 more elements

A polyurethane containing a flame retardant applied to a substrate by spraying a mixture comprising an organic polyisocyanate and a storage-stable isocyanate-reactive composition mixed at an isocyanate index of from 90 to 120 in the absence of a blowing agent, said storage-stable isocyanate-reactive composition comprising

(a) 10 to 75 percent by weight, based on the total of components (a), (b), (c), (d), and (e), of at least one isocyanate-reactive compound having a molecular weight of 400 to 10,000 and a functionality of 2 to 7;
(b) 1 to 50 percent by weight, based on the total of components (a), (b), (c), (d), and (e), of at least one isocyanate-reactive compound having a molecular weight of less than 399 and a functionality of 2 to 6;
(c) 5 to 15 percent by weight, based on the total of components (a), (b), (c), (d), and (e), of a tertiary amine or ammonium compound selected from the group consisting of
(i) an isocyanate-reactive tertiary amine polyether having a molecular weight of from 100 to 1000 and having the formula
R[NR.sup.1 R.sup.2 ].sub.m
wherein
R is saturated or unsaturated C.sub.2 -C.sub.8 aliphatic or C.sub.2 -C.sub.8 aliphatic substituted with --OH, --SH, or NHR.sup.a wherein R.sup.a is C.sub.1 -C.sub.8 alkyl or C.sub.2 -C.sub.8 alkenyl;
saturated or unsaturated C.sub.5 -C.sub.8 cycloaliphatic or C.sub.5 -C.sub.8 cycloaliphatic substituted with C.sub.1 -C.sub.8 alkyl, C.sub.2 -C.sub.8 alkenyl, C.sub.1 -C.sub.8 alkylene, --OH, --SH, or NHR.sup.a wherein R.sup.a is alkyl or alkenyl;
or five- or six-membered aromatic or heteroaromatic optionally substituted with C.sub.1 -C.sub.8 alkyl, C.sub.1 -C.sub.8 alkoxy, halogen, cyano, nitro, C.sub.1 -C.sub.8 alkylene, --OH, --SH, or NHR.sup.a wherein R.sup.a is C.sub.1 -C.sub.8 alkyl or C.sub.2 -C.sub.8 alkenyl;
R.sup.1 and R.sup.2 are independently polyether groups terminated with isocyanate-reactive groups selected from --OH, --SH, and NHR.sup.b wherein R.sup.b is C.sub.1 -C.sub.8 alkyl or C.sub.2 -C.sub.8 alkenyl;
and
m is an integer of from 1 to 4;
(ii) a fatty amido-amine;
(iii) an ammonium salt derivative of a fatty amido-amine;
and
(iv) mixtures thereof;
(d) 5 to 55 percent by weight, based on the total of components (a), (b), (c), (d), and (e), of a flame retardant;
(e) 0.01 to 1.5 percent by weight, based on the total of components (a), (b), (c), (d), and (e), of a catalyst selected from tertiary amines, organic metal compounds, and mixtures thereof;
and
(f) 0 to 15 percent by weight, based on the total of components (a), (b), (c), (d), and ( e ), of additives.

17 more elements

Dependencies are inferred from the claim text.

Facts

Application: 08/301,741Filed 6 Sep 1994 · division
Priority: 24 Aug 1993
Granted: 28 Mar 1995
Term ends: Not estimatedThe source records don’t support an estimate.

Classification10 codes

C08G 18/3825
Containing -N-C=O groups: containing amide groups
C08G 18/168
Catalysts not provided for in the groups C08G18/18 - C08G18/26: organic compounds
C08G 18/1825
Containing secondary or tertiary amines or salts thereof: having hydroxy or primary amino groups
C08G 18/28
With compounds having active hydrogen: characterised by the compounds used containing active hydrogen

Family

Serial111,099Parent of this division · filed 24 Aug 1993
Serial182,993Parent of this division · filed 14 Jan 1994
US 5,374,486 AParent of this division
US 5,302,303 AParent of this division
US 5,401,824 AThis patent

From the US filing history. Foreign family members aren’t listed.