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US4036906A Expired / Lapsed US ⏱️ 0.0 years remaining

Cured polyurethane compositions containing epoxy resins

Assignee: Goodyear Tire and Rubber Co
•
Filing: 1975-03-24
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Granted: 1977-07-19
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Expires: 1995-03-24
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Abstract

Abstract Cured polyurethane composition characterized by resistance to hydrolysis degradation prepared by reacting a polyurethane reaction mixture containing sufficient diamine curative in the presence of an excess of an epoxy resin.

Inventors

  • 👤 Anthony F. Finelli

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-25 02:42
CPC Classifications
C; C08; C08L; C08L75/00; C08L75/04

Claims Analysis

Total Claims: 5
Claim 1
Independent Claim 347 words
A cured polyurethane composition characterized by its tensile strength at 25° C. Being resistant to hydrolysis degradation when immersed in distilled water at 158° F. for 14 days prepared by the method which consists of reacting a polyurethane reaction mixture, containing sufficient diamine curative therefor, in the presence of an excess of an epoxy resin, said method consisting essentially of (A) mixing in a solvent, in order to provide a fluid mixture or solution containing about 40 to about 95 percent solids, selected from benzene, xylene, toluene, acetone, methyl ethyl ketone, methyl isobutyl ketone and diisobutyl ketone (1) an epoxy resin derived from epichlorohydrin and a bis phenol and having an epoxide equivalent in the range of about 150 to about 525, (2) a prepolymer of at least one organic diisocyanate and at least one reactive hydrogen-containing polymeric material having a molecular weight in the range of from about 700 to about 5,000 selected from polyester polyols, polyether polyols and hydroxyl terminated unsaturated polymeric polyols with a hydroxyl functionality of about 2 to about 3 where the ratio of the diisocyanate of the reactive hydrogens of the reactive hydrogen-containing polymeric material is from about 1.1/1 to about 3.5/1, and (3) a primary diamine curative where the ratio of amino groups of the curative to isocyanato groups in excess of the reactive hydrogens of the reactive hydrogen-containing polymeric material is from about 0.5/1 to about 1.1/1 and where the said polyurethane composition contains from about 2 to about 15 weight percent and at least a sufficient amount to give about a 5 to about a 50 equivalent percent excess of epoxide groups relative to the total excess of said amino groups of the curative over the said isocyanato groups, wherein said epoxy resin is contacted with said primary diamine only at or just prior to preparing said reaction mixture, and (B) substantially simultaneously removing the solvent from the mixture and reacting the prepolymer with the diamine curative in the presence of the epoxy resin at a temperature in the range of about 20° C. to about 100° C.
Claim 2
Dependent Claim 347 words
A cured polyurethane composition characterized by its tensile strength at 25° C. Being resistant to hydrolysis degradation when immersed in distilled water at 158° F. for 14 days prepared by the method which consists of reacting a polyurethane reaction mixture, containing sufficient diamine curative therefor, in the presence of an excess of an epoxy resin, said method consisting essentially of (A) mixing in a solvent, in order to provide a fluid mixture or solution containing about 40 to about 95 percent solids, selected from benzene, xylene, toluene, acetone, methyl ethyl ketone, methyl isobutyl ketone and diisobutyl ketone (1) an epoxy resin derived from epichlorohydrin and a bis phenol and having an epoxide equivalent in the range of about 150 to about 525, (2) a prepolymer of at least one organic diisocyanate and at least one reactive hydrogen-containing polymeric material having a molecular weight in the range of from about 700 to about 5,000 selected from polyester polyols, polyether polyols and hydroxyl terminated unsaturated polymeric polyols with a hydroxyl functionality of about 2 to about 3 where the ratio of the diisocyanate of the reactive hydrogens of the reactive hydrogen-containing polymeric material is from about 1.1/1 to about 3.5/1, and (3) a primary diamine curative where the ratio of amino groups of the curative to isocyanato groups in excess of the reactive hydrogens of the reactive hydrogen-containing polymeric material is from about 0.5/1 to about 1.1/1 and where the said polyurethane composition contains from about 2 to about 15 weight percent and at least a sufficient amount to give about a 5 to about a 50 equivalent percent excess of epoxide groups relative to the total excess of said amino groups of the curative over the said isocyanato groups, wherein said epoxy resin is contacted with said primary diamine only at or just prior to preparing said reaction mixture, and (B) substantially simultaneously removing the solvent from the mixture and reacting the prepolymer with the diamine curative in the presence of the epoxy resin at a temperature in the range of about 20° C. to about 100° C.
Claim 3
Independent Claim 340 words
A method of preparing a polyurethane composition having a property of being resistant to hydrolysis degradation by immersion in distilled water at 158° F. for 14 days by reacting a polyurethane reaction mixture, containing sufficient diamine curative therefor, in the presence of an excess of an epoxy resin, said method consisting essentially of (A) mixing in a solvent, in order to provide a fluid mixture or solution containing about 40 to about 95 percent solids, selected from benzene, xylene, toluene, acetone, methyl ethyl ketone, methyl isobutyl ketone and diisobutyl ketone (1) an epoxy resin derived from epichlorohydrin and a bis phenol and having an epoxide equivalent in the range of about 150 to about 525, (2) a prepolymer of at least one organic diisocyanate and at least oen reactive hydrogen-containing polymeric material having a molecular weight in the range of from about 700 to about 5,000 selected from polyester polyols, polyether polyols and hydroxyl terminated unsaturated polymeric polyols with a hydroxyl functionality of about 2 to about 3 where the ratio of the diisocyanate to the reactive hydrogens of the reactive hydrogen-containing polymeric material is from about 1.1/1 to about 3.5/1, and (3) a primary diamine curative where the ratio of amino groups of the curative to isocyanato groups in excess of the reactive hydrogens of the reactive hydrogen-containing polymeric material is from about 0.5/1 to about 1.1/1 and where the said polyurethane composition contains from about 2 to about 15 weight percent and at least a sufficient amount to give about a 5 to about a 50 equivalent percent excess of epoxide groups relative to the total excess of said amino groups of the curative over the said isocyanato groups, wherein said epoxy resin is contacted with said primary diamine only at or just prior to preparing said reaction mixture, and (B) substantially simultaneously removing the solvent from the mixture and reacting the prepolymer with the diamine curative in the presence of the epoxy resin at a temperature in the range of about 20° C. to about 100° C.
Claim 4
Independent Claim 340 words
A method of preparing a polyurethane composition having a property of being resistant to hydrolysis degradation by immersion in distilled water at 158° F. for 14 days by reacting a polyurethane reaction mixture, containing sufficient diamine curative therefor, in the presence of an excess of an epoxy resin, said method consisting essentially of (A) mixing in a solvent, in order to provide a fluid mixture or solution containing about 40 to about 95 percent solids, selected from benzene, xylene, toluene, acetone, methyl ethyl ketone, methyl isobutyl ketone and diisobutyl ketone (1) an epoxy resin derived from epichlorohydrin and a bis phenol and having an epoxide equivalent in the range of about 150 to about 525, (2) a prepolymer of at least one organic diisocyanate and at least oen reactive hydrogen-containing polymeric material having a molecular weight in the range of from about 700 to about 5,000 selected from polyester polyols, polyether polyols and hydroxyl terminated unsaturated polymeric polyols with a hydroxyl functionality of about 2 to about 3 where the ratio of the diisocyanate to the reactive hydrogens of the reactive hydrogen-containing polymeric material is from about 1.1/1 to about 3.5/1, and (3) a primary diamine curative where the ratio of amino groups of the curative to isocyanato groups in excess of the reactive hydrogens of the reactive hydrogen-containing polymeric material is from about 0.5/1 to about 1.1/1 and where the said polyurethane composition contains from about 2 to about 15 weight percent and at least a sufficient amount to give about a 5 to about a 50 equivalent percent excess of epoxide groups relative to the total excess of said amino groups of the curative over the said isocyanato groups, wherein said epoxy resin is contacted with said primary diamine only at or just prior to preparing said reaction mixture, and (B) substantially simultaneously removing the solvent from the mixture and reacting the prepolymer with the diamine curative in the presence of the epoxy resin at a temperature in the range of about 20° C. to about 100° C.
Claim 5
Dependent Claim 129 words
The method according to claim 2 where the said diisocyanates are selected from toluene diisocyanates, m-phenylene diisocyanate, 4-chloro-1,3-phenylene diisocyanate, 4,4'-tetramethylene diisocyanate, 1,6-hexamethylene diisocyanate, 1,10-decamethylene diisocyanate, 1,4-cyclohexylene diisocyanate, 4,4'-methylene-bis(cyclohexylisocyanate) and 1,5-tetrahydrophthalene diisocyanate, and mixtures of such diisocyanates, the reactive hydrogen containing polymeric material is selected from polyester polyols, polyether polyols, and hydroxyl terminated polymeric polyols selected from polybutadiene polyols, polyisoprene polyols, butadiene-styrene copolymer polyols, and butadiene-acrylonitrile copolymer polyols, the diamine is selected from ethylene diamine, trimethylene diamine, 1,4-cyclohexane bis(methylamine), and tetramethylene diamine; aromatic diamines such as m-phenylene diamine, o- and m-dichlorobenzidiene, 2,5-dichlorophenylene diamine, 3,3'-dichloro-4,4'-diamino-diphenyl methane, dianisidine, 4,4'-diamino-diphenyl methane, the naphthylene diamines, tolylene-2,4-diamine, p-aminobenzyl aniline, and o- and p-aminodiphenylamine, and where the expoxy resin is prepared from epichlorohydrin and 2,2-bis(4-hydroxyphenol) propane having an epoxide equivalency from about 150 to about 220.

References Cited (Backward Citations)

US3158586A Cited
US3440086A Cited
US3558408A Cited
US3558422A Cited
US3426097A Cited
US3546064A Cited
US3510439A Cited
US3565972A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1980-07-18 1981-01-17 1981-07-19 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1984-07-18 1985-01-17 1985-07-19 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1988-07-18 1989-01-17 1989-07-19 $7700.00 Window Closed / Lapsed

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