US4152348A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Stabilized isocyanate compositions
Assignee: CHEMTECH ROYALTY ASSOCIATES LP
•
Filing: 1978-02-22
•
Granted: 1979-05-01
•
Expires: 1998-02-22
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)
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 |