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US4487964A Expired / Lapsed US ⏱️ 0.0 years remaining

Method of making mixed aliphatic/aromatic polycarbodiimides

Assignee: Union Carbide Corp
•
Filing: 1983-02-24
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Granted: 1984-12-11
•
Expires: 2003-02-24
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Abstract

Abstract Mixed aliphatic/aromatic polycarbodiimides can be prepared by first heating aliphatic mono- and diisocyanates with a phospholene oxide catalyst and then feeding the aromatic mono and/or diisocyanates in an inert solvent to the reaction mixture, thus preparing cross-linking agents for carboxylated latexes used in making roofing materials, hardboard, pressure sensitive adhesives and the like.

Inventors

  • 👤 Stuart L. Watson, Jr.
  • 👤 Gordon R. Humphreys

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-27 20:37
CPC Classifications
C; C08; C08G; C08G18/00; C08G18/02; C08K; C08K5/00; C08K5/16; C08K5/29; C08G18/025

Claims Analysis

Total Claims: 10
Claim 1
Independent Claim 175 words
Method of preparing mixed aliphatic and aromatic polycarbodiimides which comprises the following steps seriatim: (A) charging a mixture of cycloaliphatic or saturated aliphatic mono- and diisocyanates to a reactor with agitation under an inert atmosphere; (B) heating the resultant mixture to about 120° to about 160° C.; (C) adding a catalytic amount of a phospholene oxide catalyst to the reactor; (D) feeding a mixture of a non-reactive solvent and aromatic mono- and/or diisocyanate to the reactor; and (E) maintaining agitation at about 120° to about 160° C. until all of the isocyanate functionality is converted to carbodiimide functionality, with the provisos that: (a) said cycloaliphatic moieties contain 6 to about 10 carbons; (b) said saturated aliphatic moieties contain from about 4 to about 12 carbons; (c) said aromatic moieties contain from 6 to about 16 carbons; (d) The molar ratio of all of the mono-to-diisocyanates range from about 2:1 to about 2:10; and (e) The molar ratio of cycloaliphatic and/or saturated aliphatic isocyanate groups to aromatic isocyanate groups ranges from about 0.5:1 to about 2:1.
Claim 2
Dependent Claim 175 words
Method of preparing mixed aliphatic and aromatic polycarbodiimides which comprises the following steps seriatim: (A) charging a mixture of cycloaliphatic or saturated aliphatic mono- and diisocyanates to a reactor with agitation under an inert atmosphere; (B) heating the resultant mixture to about 120° to about 160° C.; (C) adding a catalytic amount of a phospholene oxide catalyst to the reactor; (D) feeding a mixture of a non-reactive solvent and aromatic mono- and/or diisocyanate to the reactor; and (E) maintaining agitation at about 120° to about 160° C. until all of the isocyanate functionality is converted to carbodiimide functionality, with the provisos that: (a) said cycloaliphatic moieties contain 6 to about 10 carbons; (b) said saturated aliphatic moieties contain from about 4 to about 12 carbons; (c) said aromatic moieties contain from 6 to about 16 carbons; (d) The molar ratio of all of the mono-to-diisocyanates range from about 2:1 to about 2:10; and (e) The molar ratio of cycloaliphatic and/or saturated aliphatic isocyanate groups to aromatic isocyanate groups ranges from about 0.5:1 to about 2:1.
Claim 3
Dependent Claim 29 words
Method claimed in claim 1 wherein the molar ratio of cycloaliphatic and/or saturated aliphatic mono- and diisocyanates to aromatic mono- and diisocyanates ranges from about 0.75:1 to about 1.25:1.
Claim 4
Dependent Claim 19 words
Method claimed in claim 1 wherein the aliphatic monoisocyanate is butyl isocyanate and the cycloaliphatic diisocyanate is isophorone diisocyanate.
Claim 5
Dependent Claim 12 words
Method claimed in claim 2 wherein the aromatic diisocyanate is toluene diisocyanate.
Claim 6
Dependent Claim 13 words
Method claimed in claim 1 using phenyl isocyanate, isophorone diisocyanate and toluene diisocyanate.
Claim 7
Dependent Claim 12 words
Method claimed in claim 1 carried out in a non-reactive organic solvent.
Claim 8
Dependent Claim 12 words
Method claimed in claim 6 wherein the solvent is a glycol diester.
Claim 9
Dependent Claim 12 words
Method claimed in claim 6 wherein the solvent is an aliphatic ester.
Claim 10
Dependent Claim 12 words
Method claimed in claim 1 wherein the phospholene oxide catalyst is 3-methyl-1-phenyl-2-phospholene-1-oxide.

References Cited (Backward Citations)

US3193524A Cited
US2853473A Cited
US3193522A Cited
US3193523A Cited
US3296190A Cited
US3639353A Cited
US3929733A Cited
US4042558A Cited
US4148844A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1987-12-11 1988-06-11 1988-12-11 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1991-12-11 1992-06-11 1992-12-11 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1995-12-11 1996-06-11 1996-12-11 $7700.00 Window Closed / Lapsed

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