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US3876728A Expired / Lapsed US ⏱️ 0.0 years remaining

Urethane resins from tolylene diisocyanate distillation residues active hydrogen containing compounds and vinyl monomers

Assignee: Hodogaya Chemical Co Ltd
•
Filing: 1973-03-16
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Granted: 1975-04-08
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Expires: 1993-03-16
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Abstract

Abstract A novel cured resin is produced by reacting an active hydrogencontaining compound with a solution in a polymerizable unsaturated monomer of the NCO group-containing distillation residue obtained in the production of tolylene diisocyanate from tolylene diamine or its salt and phosgene, in the presence of a polymerization catalyst, and the resin thus obtained is superior in thermal resistance, mechanical strength, adhesion, solvent resistance, chemical resistance, etc. to a polymer obtained by polymerizing the above polymerizable unsaturated monomer alone in the same manner.

Inventors

  • 👤 Akira Kuroda
  • 👤 Masaaki Hirooka

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-23 15:22
CPC Classifications
C; C08; C08G; C08G18/00; C08G18/04; C08G18/06; C08G18/28; C08G18/40; C08G18/63; C08G18/637; C08G18/67; C08G18/70; C08G18/702; C08G18/72; C08G18/721; C08G18/727

Claims Analysis

Total Claims: 7
Claim 1
Independent Claim 89 words
A METHOD FOR PREPARING A CURED RESIN, WHICH COMPRISES REACTING IN THE PRESENCE OF A POLYMERIZATION CATALYST AN ACTIVE HYDROGEN-CONTAINING COMPOUND WITH A SOLUTION IN A POLYMERIZABLE UNSATURATED MONOMER OF THE NCO-CONTAINING DISTILLATION RESIDUE OBTAINED IN THE PRODUCTION OF TOTYLENE DIISOCYANATE FROM TOTYLENE DIAMINE OR ITS SALT AND PHOSGENE, WHEREBY SAID DISTALLATION RESIDUE AMOUNTS TO BETWEEN 30 AND 70 PERCENT OF SAID SOLUTION, THE EQUIVALENT RATIO OF NCO: ACTIVE HYDROGEN IS 0.5:2.0 AND THE AMOUNT OF POLYMERIZED UNSATURATED MONOMER IN THE FINAL RESIN IS BETWEEN 20 AND 80 PERCENT.
Claim 2
Independent Claim 89 words
A METHOD FOR PREPARING A CURED RESIN, WHICH COMPRISES REACTING IN THE PRESENCE OF A POLYMERIZATION CATALYST AN ACTIVE HYDROGEN-CONTAINING COMPOUND WITH A SOLUTION IN A POLYMERIZABLE UNSATURATED MONOMER OF THE NCO-CONTAINING DISTILLATION RESIDUE OBTAINED IN THE PRODUCTION OF TOTYLENE DIISOCYANATE FROM TOTYLENE DIAMINE OR ITS SALT AND PHOSGENE, WHEREBY SAID DISTALLATION RESIDUE AMOUNTS TO BETWEEN 30 AND 70 PERCENT OF SAID SOLUTION, THE EQUIVALENT RATIO OF NCO: ACTIVE HYDROGEN IS 0.5:2.0 AND THE AMOUNT OF POLYMERIZED UNSATURATED MONOMER IN THE FINAL RESIN IS BETWEEN 20 AND 80 PERCENT.
Claim 3
Independent Claim 164 words
A method for preparing a cured resin, which comprises reacting a solution of the NCO-containing distillation residue obtained in the production of tolyene diisocyanate from tolyene diamine or its salt and phosgene, in a polymerizable monomer selected from the group consisting of styrene, methyl methacrylate and vinyl acetate, with an active hydrogen-containing compound selected from the group consisting of polyether polyols, dipropylene glycol, neopentyl glycol, castor oil, furfuryl alcohol, unsaturated polyester resins, hydroxy-terminated unsaturated polyester glycols and water in the presence of a polymerization catalyst selected from the group consisting of benzoyl peroxide, methyl ethyl ketone peroxide, a combination of cobalt naphthenate and methyl ethyl ketone peroxide, a combination of benzoyl peroxide and dimethylaniline, a combination of sodium metabisulfate and potassium persulfate, and tin tetrachloride, whereby said distillation residue amounts to between 30 and 70 percent of said solution, the equivalent ratio of NCO: active hydrogen is 0.5:2.0 and the amount of polymerized unsaturated monomer in the final resin is between 20 and 80
Claim 4
Independent Claim 164 words
A method for preparing a cured resin, which comprises reacting a solution of the NCO-containing distillation residue obtained in the production of tolyene diisocyanate from tolyene diamine or its salt and phosgene, in a polymerizable monomer selected from the group consisting of styrene, methyl methacrylate and vinyl acetate, with an active hydrogen-containing compound selected from the group consisting of polyether polyols, dipropylene glycol, neopentyl glycol, castor oil, furfuryl alcohol, unsaturated polyester resins, hydroxy-terminated unsaturated polyester glycols and water in the presence of a polymerization catalyst selected from the group consisting of benzoyl peroxide, methyl ethyl ketone peroxide, a combination of cobalt naphthenate and methyl ethyl ketone peroxide, a combination of benzoyl peroxide and dimethylaniline, a combination of sodium metabisulfate and potassium persulfate, and tin tetrachloride, whereby said distillation residue amounts to between 30 and 70 percent of said solution, the equivalent ratio of NCO: active hydrogen is 0.5:2.0 and the amount of polymerized unsaturated monomer in the final resin is between 20 and 80
Claim 5
Dependent Claim 40 words
A method according to claim 1, wherein the polymerizable unsaturated monomer is styrene, the active hydrogen-containing compound is a combination of an unsaturated polyester resin and polyether triol, and the polymerization catalyst is a combination of methyl ethyl ketone peroxide
Claim 6
Dependent Claim 42 words
A method according to claim 1, wherein the solution and the active hydrogen-containing compound are subjected to polymerization at a temperature of 5.degree. to 150.degree.C in the presence of the polymerization catalyst in an amount corresponding to 0.1 to 5 percent by
Claim 7
Dependent Claim 11 words
A cured resin composition obtained by the method of claim 1.

References Cited (Backward Citations)

US3304273A Cited
US3479384A Cited
US3522285A Cited
US3700752A Cited
US3723363A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1978-04-07 1978-10-07 1979-04-08 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1982-04-07 1982-10-07 1983-04-08 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1986-04-07 1986-10-07 1987-04-08 $7700.00 Window Closed / Lapsed

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