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US4152348A Expired / Lapsed US ⏱️ 0.0 years remaining

Stabilized isocyanate compositions

Assignee: CHEMTECH ROYALTY ASSOCIATES LP
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Filing: 1978-02-22
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Granted: 1979-05-01
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Expires: 1998-02-22
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Abstract

Abstract Color stabilized isocyanates, particularly methylene-bridged aromatic isocyanates [methylenebis(phenyl isocyanate) and prepolymers thereof], are derived by incorporating in the isocyanate a color stabilizing amount of a compound of the formula ##STR1## wherein R 1 =alkyl, aryl; R 2 =alkyl; R 3 =H, alkyl or aralkyl; and R 1 and R 2 taken together represent the residue of an oxazoline or oxazine. 2-Ethyloxazoline is a preferred color stabilizing compound. The above compounds can also be used to discharge undesirable colors which have developed in such isocyanates on storage.

Inventors

  • 👤 Warren J. Rabourn

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-24 17:22
CPC Classifications
C; C07; C07C; C07C265/00; C07C265/14; C07C263/00; C07C263/18

Claims Analysis

Total Claims: 27
Claim 1
Independent Claim 121 words
An isocyanate composition stabilized against color formation which comprises an organic isocyanate, which is normally susceptible to color formation on storage, having incorporated therein a color stabilizing amount of a compound having the formula ##STR6## wherein R 1 is selected from the group consisting of lower-alkyl and aryl, having from 6 to 12 carbon atoms, inclusive, R 2 represents lower-alkyl, R 1 and R 2 taken together represent lower-alkylene having 2 to 3 carbon atoms in the chain which with the ##STR7## group forms the residue of a heterocyclic ring containing from 5 to 6 ring atoms and R 3 represents a group selected from the class consisting of hydrogen, lower-alkyl, and aralkyl having from 7 to 13 carbon atoms, inclusive.
Claim 2
Dependent Claim 121 words
An isocyanate composition stabilized against color formation which comprises an organic isocyanate, which is normally susceptible to color formation on storage, having incorporated therein a color stabilizing amount of a compound having the formula ##STR6## wherein R 1 is selected from the group consisting of lower-alkyl and aryl, having from 6 to 12 carbon atoms, inclusive, R 2 represents lower-alkyl, R 1 and R 2 taken together represent lower-alkylene having 2 to 3 carbon atoms in the chain which with the ##STR7## group forms the residue of a heterocyclic ring containing from 5 to 6 ring atoms and R 3 represents a group selected from the class consisting of hydrogen, lower-alkyl, and aralkyl having from 7 to 13 carbon atoms, inclusive.
Claim 3
Dependent Claim 16 words
A composition according to claim 1 wherein said isocyanate contains a color stabilizing amount of 2-ethyloxazoline.
Claim 4
Dependent Claim 17 words
A composition according to claim 1 wherein said isocyanate contains a color stabilizing amount of ethyl N-phenylformimidate.
Claim 5
Dependent Claim 16 words
A composition according to claim 1 wherein said isocyanate contains a color stabilizing amount of 2-benzyl-5,6-dihydro-4,4,6-trimethyl-4H-1,3-oxazine.
Claim 6
Dependent Claim 16 words
A composition according to claim 1 wherein said isocyanate contains a color stabilizing amount of 2-methyloxazoline.
Claim 7
Dependent Claim 16 words
A composition according to claim 1 wherein said isocyanate contains a color stabilizing amount of 2,4,4-trimethyloxazoline.
Claim 8
Dependent Claim 12 words
A composition according to claim 1 wherein said isocyanate is methylenebis(phenyl isocyanate).
Claim 9
Dependent Claim 19 words
A composition according to claim 1 wherein said isocyanate is a prepolymer of methylenebis(phenyl isocyanate) and an aliphatic diol.
Claim 10
Dependent Claim 124 words
An isocyanate composition stabilized against color formation which comprises an organic isocyanate selected from methylenebis(phenyl isocyanate) and prepolymers thereof with aliphatic diols, said isocyanate having incorporated therein a color stabilizing amount of a compound having the formula: ##STR8## wherein R 1 is selected from the group consisting of lower-alkyl and aryl, having from 6 to 12 carbon atoms, inclusive, R 2 represents lower-alkyl, R 1 and R 2 taken together represent lower-alkylene having 2 to 3 carbon atoms in the chain which with the ##STR9## group forms the residue of a heterocyclic ring containing from 5 to 6 ring atoms, and R 3 represents a group selected from the class consisting of hydrogen, lower-alkyl, and aralkyl having from 7 to 13 carbon atoms, inclusive.
Claim 11
Dependent Claim 124 words
An isocyanate composition stabilized against color formation which comprises an organic isocyanate selected from methylenebis(phenyl isocyanate) and prepolymers thereof with aliphatic diols, said isocyanate having incorporated therein a color stabilizing amount of a compound having the formula: ##STR8## wherein R 1 is selected from the group consisting of lower-alkyl and aryl, having from 6 to 12 carbon atoms, inclusive, R 2 represents lower-alkyl, R 1 and R 2 taken together represent lower-alkylene having 2 to 3 carbon atoms in the chain which with the ##STR9## group forms the residue of a heterocyclic ring containing from 5 to 6 ring atoms, and R 3 represents a group selected from the class consisting of hydrogen, lower-alkyl, and aralkyl having from 7 to 13 carbon atoms, inclusive.
Claim 12
Dependent Claim 13 words
A composition according to claim 9 wherein the color stabilizing compound is 2-ethyloxazoline.
Claim 13
Dependent Claim 14 words
A composition according to claim 9 wherein the color stabilizing compound is ethyl N-phenylformimidate.
Claim 14
Dependent Claim 13 words
A composition according to claim 9 wherein the color stabilizing compound is 2-benzyl-5,6-dihydro-4,4,6-trimethyl-4H-1,3-oxazine.
Claim 15
Dependent Claim 13 words
A composition according to claim 9 wherein the color stabilizing compound is 2-methyloxazoline.
Claim 16
Dependent Claim 13 words
A composition according to claim 9 wherein the color stabilizing compound is 2,4,4-trimethyloxazoline.
Claim 17
Dependent Claim 17 words
A composition according to claim 9 which also comprises color stabilizing amounts of triphenyl phosphite and 2,6-di-tert.-butyl-4-methylphenol.
Claim 18
Dependent Claim 18 words
A composition stabilized against the formation of color comprising 4,4'-methylenebis(phenyl isocyanate) and a color stabilizing amount of 2-ethyloxazoline.
Claim 19
Dependent Claim 18 words
A composition stabilized against the formation of color comprising 4,4'-methylenebis(phenyl isocyanate) and a color stabilizing amount of 2-ethyloxazoline.
Claim 20
Dependent Claim 17 words
A composition according to claim 16 which also comprises color stabilizing amounts of triphenyl phosphite and 2,6-di-tert.-butyl-4-methylphenol.
Claim 21
Dependent Claim 18 words
A composition stabilized against the formation of color comprising 4,4'-methylenebis(phenyl isocyanate) and a color stabilizing amount of 2-methyloxazoline.
Claim 22
Dependent Claim 18 words
A composition stabilized against the formation of color comprising 4,4'-methylenebis(phenyl isocyanate) and a color stabilizing amount of 2-methyloxazoline.
Claim 23
Dependent Claim 110 words
A process for discharging the color which has formed on storage of an aromatic isocyanate containing a methylene group bridging two aromatic nuclei which process comprises incorporating into said isocyanate a color discharging quantity of a compound having the formula: ##STR10## wherein R 1 is selected from the group consisting of lower-alkyl and aryl, R 2 represents lower-alkyl, R 1 and R 2 taken together with the ##STR11## group to which they are attached form the residue of a heterocyclic ring selected from oxazoline and oxazine, and R 3 represents a group selected from the class consisting of hydrogen, lower-alkyl, and aralkyl having from 7 to 13 carbon atoms, inclusive.
Claim 24
Dependent Claim 110 words
A process for discharging the color which has formed on storage of an aromatic isocyanate containing a methylene group bridging two aromatic nuclei which process comprises incorporating into said isocyanate a color discharging quantity of a compound having the formula: ##STR10## wherein R 1 is selected from the group consisting of lower-alkyl and aryl, R 2 represents lower-alkyl, R 1 and R 2 taken together with the ##STR11## group to which they are attached form the residue of a heterocyclic ring selected from oxazoline and oxazine, and R 3 represents a group selected from the class consisting of hydrogen, lower-alkyl, and aralkyl having from 7 to 13 carbon atoms, inclusive.
Claim 25
Dependent Claim 13 words
A process according to claim 19 wherein said color discharging compound is 2-ethyloxazoline.
Claim 26
Dependent Claim 13 words
A process according to claim 19 wherein said aromatic isocyanate is 4,4'-methylenebis(phenyl isocyanate).
Claim 27
Dependent Claim 22 words
A process according to claim 19 wherein said aromatic isocyanate is a prepolymer of 4,4'-methylenebis(phenyl isocyanate) and at least one aliphatic diol.

References Cited (Backward Citations)

US3380959A Cited
US3846419A Cited
US3661861A Cited
US3914189A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1982-04-30 1982-10-30 1983-05-01 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1986-04-30 1986-10-30 1987-05-01 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1990-04-30 1990-10-30 1991-05-01 $7700.00 Window Closed / Lapsed

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