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US4520186A Expired / Lapsed US ⏱️ 0.0 years remaining

Polyurethanes and polyurethane-ureas based on aromatic uret dione diamine adducts

Assignee: Bayer AG
•
Filing: 1983-08-25
•
Granted: 1985-05-28
•
Expires: 2003-08-25
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Abstract

Abstract Aromatic uret dione diurea diamines corresponding to the formula ##STR1## in which X, Y, m and n are as defined herein are produced by reacting an aromatic diamine with a diisocyanate corresponding to a specified formula in a molar ratio of diamine to diisocyanate of at least 1.8 to 1. These diamines are particularly useful in the production of elastomers.

Inventors

  • 👤 Heinrich Hess
  • 👤 Gerhard Grogler
  • 👤 Richard Kopp

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-23 00:27
CPC Classifications
C; C08; C08G; C08G18/00; C08G18/06; C08G18/28; C08G18/30; C08G18/38; C08G18/3819; C08G18/3842; C08G18/3848; C07; C07D; C07D229/00; C08G18/08; C08G18/10; C08G18/32; C08G18/3225; C08G18/3237

Claims Analysis

Total Claims: 16
Claim 1
Independent Claim 111 words
An aromatic uret dione diurea diamine corresponding to the formula ##STR11## in which X represents an aromatic radical having a molecular weight of from 76 to 499, Y represents an aromatic radical having a molecular weight of from 76 to 10,000 or a radical derived from a high molecular weight diamine corresponding to the formula ##STR12## in which Z represents a radical derived from a dihydroxy compound HO--Z--OH, provided that when Y represents a group derived from a diamine having a molecular weight ≧500 X does not represent a 2,4-diphenyl sulfide radical, m represents a number of from 1 to 10 and n represents a number of from 1 to 3.
Claim 2
Dependent Claim 111 words
An aromatic uret dione diurea diamine corresponding to the formula ##STR11## in which X represents an aromatic radical having a molecular weight of from 76 to 499, Y represents an aromatic radical having a molecular weight of from 76 to 10,000 or a radical derived from a high molecular weight diamine corresponding to the formula ##STR12## in which Z represents a radical derived from a dihydroxy compound HO--Z--OH, provided that when Y represents a group derived from a diamine having a molecular weight ≧500 X does not represent a 2,4-diphenyl sulfide radical, m represents a number of from 1 to 10 and n represents a number of from 1 to 3.
Claim 3
Dependent Claim 22 words
The aromatic uret dione diurea diamine of claim 1 in which X represents a 2,4-tolylene and/or 4,4'-diphenyl methane and/or 2,4'-diphenyl methane radical.
Claim 4
Dependent Claim 20 words
The aromatic uret dione diurea diamine of claim 1 in which m represents a number of from 1 to 2.
Claim 5
Dependent Claim 28 words
The aromatic uret dione diurea diamine of claim 1 in which Y represents a 4,4'-diphenyl methane radical and/or 3,5-diisopropyl-3',5'-diethyl-4,4'-diphenyl methane radical and/or 3,5-diethyl-2,4-(2,6-) tolylene radical and/or 1,4-phenylene radical.
Claim 6
Dependent Claim 28 words
The aromatic uret dione diurea diamine of claim 1 in which Y represents a radical derived from a diamine having a molecular weight of from 1000 to 6000.
Claim 7
Dependent Claim 152 words
A process for the production of aromatic uret dione diurea diamines in finely particulate or suspended form which diamines correspond to the formula ##STR13## in which X represents an aromatic radical having a molecular weight of from 76 to 499, Y represents an aromatic radical having a molecular weight of from 76 to 10,000 or a radical corresponding to the formula ##STR14## in which Z represents a radical derived from a dihydroxy compound HO--Z--OH, provided that when Y represents a radical derived from a diamine H 2 N--Y--NH 2 having a molecular weight ≧500, X does not represent a 2,4'-diphenyl sulfide radical, m represents a number of from 1 to 10 and n represents a number of from 1 to 3 comprising mixing an aromatic diamine H 2 N--Y--NH 2 with a finely particulate diisocyanate corresponding to the formula ##STR15## in a molar ratio of diamine to diisocyanate of at least 1.8:1.
Claim 8
Dependent Claim 152 words
A process for the production of aromatic uret dione diurea diamines in finely particulate or suspended form which diamines correspond to the formula ##STR13## in which X represents an aromatic radical having a molecular weight of from 76 to 499, Y represents an aromatic radical having a molecular weight of from 76 to 10,000 or a radical corresponding to the formula ##STR14## in which Z represents a radical derived from a dihydroxy compound HO--Z--OH, provided that when Y represents a radical derived from a diamine H 2 N--Y--NH 2 having a molecular weight ≧500, X does not represent a 2,4'-diphenyl sulfide radical, m represents a number of from 1 to 10 and n represents a number of from 1 to 3 comprising mixing an aromatic diamine H 2 N--Y--NH 2 with a finely particulate diisocyanate corresponding to the formula ##STR15## in a molar ratio of diamine to diisocyanate of at least 1.8:1.
Claim 9
Dependent Claim 34 words
The process of claim 6 in which the aromatic diamine H 2 N--Y--NH 2 is used in the form of a solution in an isocyanate-inert solvent or in a relatively high molecular weight polyol.
Claim 10
Dependent Claim 25 words
The process of claim 6 in which the finely particulate uret dione diisocyanate is suspended in an isocyanate-inert solvent and/or relatively high molecular weight polyol.
Claim 11
Dependent Claim 66 words
A process for the production of urea-group-containing high molecular weight polyaddition products comprising reacting (a) the aromatic uret dione diurea diamine of claim 1 with (b) an NCO-prepolymer of polyol and excess polyisocyanate and/or a polyisocyanate at a temperature greater than 100° C. in quantities such that the equivalent ratio of NCO-groups to the sum of OH- and NH 2 -groups is from 0.9 to 1.4.
Claim 12
Dependent Claim 25 words
The process of claim 9 in which a polyhydroxyl compound having a molecular weight of from 400 to 10,000 is included in the reaction mixture.
Claim 13
Dependent Claim 25 words
The process of claim 9 in which a chain extender having a molecular weight of from 32 to 399 is included in the reaction mixture.
Claim 14
Dependent Claim 34 words
The process of claim 9 further comprising the step of crosslinking the reaction product of (a) and (b) in the presence of excess OH- and/or NH 2 -groups at a temperature above 140° C.
Claim 15
Dependent Claim 60 words
A self-crosslinking one component system at temperatures above 140° C. comprising the reaction product of a (i) long chain diamine H 2 N--Y--NH 2 having a molecular weight of at least 500 where Y represents a radical corresponding to the formula ##STR16## in which Z represents a radical derived from a dihydroxy compound HO--Z--OH with (ii) a uret dione diisocyanate.
Claim 16
Dependent Claim 60 words
A self-crosslinking one component system at temperatures above 140° C. comprising the reaction product of a (i) long chain diamine H 2 N--Y--NH 2 having a molecular weight of at least 500 where Y represents a radical corresponding to the formula ##STR16## in which Z represents a radical derived from a dihydroxy compound HO--Z--OH with (ii) a uret dione diisocyanate.

References Cited (Backward Citations)

US2643250A Cited
US3475200A Cited
US3793238A Cited
US3998794A Cited
US4176118A Cited
US4251427A Cited
US4405752A Cited
EP0074023A1 Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1988-05-27 1988-11-26 1989-05-28 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1992-05-27 1992-11-26 1993-05-28 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1996-05-27 1996-11-26 1997-05-28 $7700.00 Window Closed / Lapsed

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