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US4659747A Expired / Lapsed US ⏱️ 0.0 years remaining

Cyclohexanedimethanol/diamine mixtures as RIM extenders

Assignee: Dow Chemical Co
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Filing: 1986-05-15
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Granted: 1987-04-21
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Expires: 2006-05-15
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Abstract

Abstract Polyurethane-polyurea polymers are disclosed that are derived from the reaction injection molding of organic polyisocyanates, optional high molecular weight active hydrogen containing compounds and extender mixtures comprising (i) aromatic diamines wherein at least one of the positions ortho to each amine group is substituted by a lower alkyl group and (ii) bis(hydroxyalkyl)cycloalkanes. The improved polymers have excellent resistance to high temperature conditions.

Inventors

  • 👤 Louis M. Alberino
  • 👤 James R. Pritchard
  • 👤 Nancy P. Vespoli

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-23 03:42
CPC Classifications
C; C08; C08G; C08G18/00; C08G18/06; C08G18/70; C08G18/72; C08G18/28; C08G18/30; C08G18/32; C08G18/3225; C08G18/3237; C08G18/3203; C08G18/3212; C08G18/65; C08G18/6505; C08G18/6523; C08G18/6529; C08G18/66; C08G2120/00

Claims Analysis

Total Claims: 25
Claim 1
Independent Claim 79 words
In a polyurethane polyurea polymer prepared by the catalyzed reaction injection molding of an organic polyisocyanate, an optional high molecular weight compound having at least two active hydrogen containing groups, and an extender mixture comprising (i) an aromatic diamine wherein at least one of the positions ortho to each amine group of said diamine is substituted by a lower alkyl group and (ii) a low molecular weight diol, the improvement which comprises employing as said diol a bis (hydroxyalkyl)cycloalkane.
Claim 2
Dependent Claim 79 words
In a polyurethane polyurea polymer prepared by the catalyzed reaction injection molding of an organic polyisocyanate, an optional high molecular weight compound having at least two active hydrogen containing groups, and an extender mixture comprising (i) an aromatic diamine wherein at least one of the positions ortho to each amine group of said diamine is substituted by a lower alkyl group and (ii) a low molecular weight diol, the improvement which comprises employing as said diol a bis (hydroxyalkyl)cycloalkane.
Claim 3
Dependent Claim 35 words
A polymer according to claim 1 wherein said extender mixture comprises (i) from about 20 to about 95 percent by weight of said diamine and complementally (ii) from 80 to 5 percent of said bis(hydroxyalkyl)cycloalkane.
Claim 4
Dependent Claim 22 words
A polymer according to claim 1 wherein said aromatic diamine is selected from the group consisting of 1-methyl-3,5-diethyl-2,4-diaminobenzene, 1-methyl-3,5-diethyl-2,6-diaminobenzene, and mixtures thereof.
Claim 5
Dependent Claim 12 words
A polymer according to claim 1 wherein said diol comprises a bis(hydroxyalkyl)cyclohexane.
Claim 6
Dependent Claim 36 words
A polymer according to claim 1 wherein the ratio of isocyanate equivalents to the total active hydrogen equivalents of said optional active hydrogen containing compound and said extender mixture is from about 0.85 to about 1.2.
Claim 7
Dependent Claim 41 words
A polymer according to claim 1 wherein said optional active hydrogen containing compound is present such that its equivalent proportions to the total active hydrogen equivalents of said extender mixture falls within the range of from about 1:4 to about 1:100.
Claim 8
Dependent Claim 21 words
A polymer according to claim 6 wherein said equivalent proportions fall within a range of from about 1:10 to about 1:80.
Claim 9
Dependent Claim 16 words
A polymer according to claim 1 wherein said optional active hydrogen containing compound comprises a polyol.
Claim 10
Dependent Claim 32 words
A polymer according to claim 8 wherein said polyol has a molecular weight of from about 1500 to about 7000 and a primary hydroxyl functionality of from about 2 to about 4.
Claim 11
Dependent Claim 13 words
A polymer according to claim 1 wherein said polyisocyanate comprises an aromatic polyisocyanate.
Claim 12
Dependent Claim 38 words
A polymer according to claim 10 wherein said polyisocyanate is selected from the group consisting of (a) an isocyanate terminated prepolymer prepared from methylenebis(phenyl isocyanate); (b) a liquefied form of 4,4'-methylenebis(phenyl isocyanate); and mixtures of (a) and (b).
Claim 13
Dependent Claim 171 words
A high flexural-modulus polyurethane polyurea polymer prepared by the reaction injection molding of A a polyisocyanate selected from the group consisting of (a) an isocyanate terminated prepolymer prepared from methylenebis (phenyl isocyanate); (b) a liquefied form of 4,4'-methylenebis(phenyl isocyanate); and mixtures of (a) and (b); B. a polyol having a molecular weight of from about 1500 to about 7000 and a primary hydroxyl functionality of from about 2 to about 4; C. an extender mixture comprising (i) from about 20 to about 95 percent by weight of an aromatic diamine selected from the group consisting of 1-methyl-3.5-diethyl-2,4-diaminobenzene, 1-methyl-3,5-diethyl-2,6-diaminobenzene, and mixtures thereof; and (ii) from about 80 to about 5 percent of a bis(hydroxyalkyl)cyclohexane, and D. a urethane catalyst wherein the equivalent proportions of said polyol (B) to the total active hydrogen equivalents of said extender mixture (C) falls within the range of from about 1:10 to about 1:80 and the ratio of isocyanate equivalents to the total active hydrogen equivalents of (B) and (C) is from about 0.85 to about 1.2
Claim 14
Dependent Claim 171 words
A high flexural-modulus polyurethane polyurea polymer prepared by the reaction injection molding of A a polyisocyanate selected from the group consisting of (a) an isocyanate terminated prepolymer prepared from methylenebis (phenyl isocyanate); (b) a liquefied form of 4,4'-methylenebis(phenyl isocyanate); and mixtures of (a) and (b); B. a polyol having a molecular weight of from about 1500 to about 7000 and a primary hydroxyl functionality of from about 2 to about 4; C. an extender mixture comprising (i) from about 20 to about 95 percent by weight of an aromatic diamine selected from the group consisting of 1-methyl-3.5-diethyl-2,4-diaminobenzene, 1-methyl-3,5-diethyl-2,6-diaminobenzene, and mixtures thereof; and (ii) from about 80 to about 5 percent of a bis(hydroxyalkyl)cyclohexane, and D. a urethane catalyst wherein the equivalent proportions of said polyol (B) to the total active hydrogen equivalents of said extender mixture (C) falls within the range of from about 1:10 to about 1:80 and the ratio of isocyanate equivalents to the total active hydrogen equivalents of (B) and (C) is from about 0.85 to about 1.2
Claim 15
Dependent Claim 23 words
A polyurethane-polyurea according to claim 12 wherein said extender (i) comprises a mixture of 1-methyl-3,5-diethyl-2,4-,and 2,6-diaminobenzene and said extender (ii) comprises bis(hydroxymethyl) cyclohexane.
Claim 16
Dependent Claim 29 words
A polyurethane-polyurea according to claim 13 wherein said (i) is from about 45 to about 85 percent by weight and said (ii) from about 55 to about 15 percent.
Claim 17
Dependent Claim 16 words
A polyurethane-polyurea according to claim 14 wherein said polyisocyanate comprises a liquefied form of 4,4'-methylenebis(phenyl isocyanate).
Claim 18
Dependent Claim 28 words
A polyurethane-polyurea according to claim 14 wherein said polyisocyanate comprises a mixture of an isocyanate terminated prepolymer prepared from methylenebis(phenyl isocyanate) and a liquefied form of 4,4'-methylenebis(phenyl isocyanate).
Claim 19
Dependent Claim 32 words
A miscible blend comprising (i) an aromatic diamine wherein at least one of the positions ortho to each amine group is substituted by a lower alkyl group and (ii) a bis(hydroxyalkyl) cycloalkane.
Claim 20
Dependent Claim 32 words
A miscible blend comprising (i) an aromatic diamine wherein at least one of the positions ortho to each amine group is substituted by a lower alkyl group and (ii) a bis(hydroxyalkyl) cycloalkane.
Claim 21
Dependent Claim 23 words
A blend according to claim 17 wherein (i) comprises an aromatic diamine selected from the group consisting of 1-methyl-3,5-diethyl-2,4-diaminobenzene, 1-methyl-3,5-diethyl-2,6,-diaminobenzene, and mixtures thereof.
Claim 22
Dependent Claim 11 words
A blend according to claim 17 wherein (ii) comprises a bis(hydroxyalkyl)cyclohexane.
Claim 23
Dependent Claim 28 words
A blend according to claim 17 comprising from about 20 to about 95 percent by weight of (i) and from about 80 to about 5 percent of (ii).
Claim 24
Dependent Claim 36 words
A blend according to claim 17 comprising (i) from about 45 to about 85 percent by weight of a mixture of 1-methyl-3,5-diethyl-2,4-diaminobenzene and 1-methyl-3,5-diethyl-2,6-diaminobenzene and (ii) from about 55 to about 15 percent of bis(hydroxymethyl) cyclohexane.
Claim 25
Dependent Claim 24 words
A miscible blend comprising a blend according to claim 17 and a high molecular weight compound having at least two active hydrogen containing groups.

References Cited (Backward Citations)

US4218543A Cited
US4269945A Cited
US4296212A Cited
US4374210A Cited
US4433067A Cited
US4530941A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1990-04-20 1990-10-20 1991-04-21 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1994-04-20 1994-10-20 1995-04-21 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1998-04-20 1998-10-20 1999-04-21 $7700.00 Window Closed / Lapsed

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