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US4064157A Expired / Lapsed US ⏱️ 0.0 years remaining

Stabilization of polyisocyanates against discoloration

Assignee: Dow Chemical Co
•
Filing: 1976-03-29
•
Granted: 1977-12-20
•
Expires: 1996-03-29
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Abstract

Abstract Polyisocyanates are stabilized against discoloration by the addition of certain hindered phenols such as o,o-di-n-octadecyl-3,5-di-tert-butyl-4-hydroxyl benzyl phosphonate.

Inventors

  • 👤 John L. Nafziger
  • 👤 John M. Motes

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-08 09:12
CPC Classifications
C; C07; C07C; C07C265/00; C07C265/14; C07C263/00; C07C263/18

Claims Analysis

Total Claims: 30
Claim 1
Independent Claim 35 words
A polyisocyanate containing as a stabilizer against discoloration, from about 20 to about 2500 ppm of a stabilizer selected from the group consisting of 1. o,o-di-n-octadecyl-3,5-di-tert-butyl-4-hydroxybenzylphosphonate, 2. tetrakis(methylene(3,5-di-tert-butyl-4-hydroxyhydrocinnamate))methane, 3. bis(2- (4-hydroxy-3,5-di-tert-butylphenyl) ethyl)sulfide, 4. octadecyl-3,5-di-tert-butyl-4-hydroxy-hydrocinnamate, and
Claim 2
Dependent Claim 35 words
A polyisocyanate containing as a stabilizer against discoloration, from about 20 to about 2500 ppm of a stabilizer selected from the group consisting of 1. o,o-di-n-octadecyl-3,5-di-tert-butyl-4-hydroxybenzylphosphonate, 2. tetrakis(methylene(3,5-di-tert-butyl-4-hydroxyhydrocinnamate))methane, 3. bis(2- (4-hydroxy-3,5-di-tert-butylphenyl) ethyl)sulfide, 4. octadecyl-3,5-di-tert-butyl-4-hydroxy-hydrocinnamate, and
Claim 3
Dependent Claim 2 words
mixtures thereof.
Claim 4
Dependent Claim 2 words
mixtures thereof.
Claim 5
Dependent Claim 27 words
The composition of claim 1 wherein the polyisocyanate is toluene diisocyanate and the stabilizer is present in quantities of from about 50 ppm to about 500 ppm.
Claim 6
Dependent Claim 15 words
The composition of claim 2 wherein the polyisocyanate is an 80/20 mixture of 2,4-/2,6-toluene diisocyanate.
Claim 7
Dependent Claim 65 words
The process for preparing a polyisocyanate resistant to discoloration upon storage which comprises distilling said polyisocyanate in the presence of at least about 25 ppm of an organic phosphite selected from the group consisting of 1. triphenyl phosphite, 2. diphenylisodecyl phosphite, 3. trisononylphenyl phosphite, 4. trilauryl phosphite, and 5. mixtures thereof; and adding to the resultant distillate a stabilizer selected from the group consisting of
Claim 8
Dependent Claim 65 words
The process for preparing a polyisocyanate resistant to discoloration upon storage which comprises distilling said polyisocyanate in the presence of at least about 25 ppm of an organic phosphite selected from the group consisting of 1. triphenyl phosphite, 2. diphenylisodecyl phosphite, 3. trisononylphenyl phosphite, 4. trilauryl phosphite, and 5. mixtures thereof; and adding to the resultant distillate a stabilizer selected from the group consisting of
Claim 9
Dependent Claim 28 words
o,o-di-n-octadecyl-3,5-di-tert-butyl-4-hydroxybenzylphosphonte, 2. tetrakis(methylene(3,5-di-tert-butyl-4-hydroxyhydrocinnamate))methane, 3. bis(2-(4-hydroxy-3,5-di-tert-butylphenyl)ethyl)sulfide, 4. octadecyl-3,5-di-tert-butyl-4-hydroxyhydrocinnamate, and 5. mixtures thereof; and wherein said stabilizer is employed in quantities of from about 20 ppm to about 250 ppm.
Claim 10
Dependent Claim 28 words
o,o-di-n-octadecyl-3,5-di-tert-butyl-4-hydroxybenzylphosphonte, 2. tetrakis(methylene(3,5-di-tert-butyl-4-hydroxyhydrocinnamate))methane, 3. bis(2-(4-hydroxy-3,5-di-tert-butylphenyl)ethyl)sulfide, 4. octadecyl-3,5-di-tert-butyl-4-hydroxyhydrocinnamate, and 5. mixtures thereof; and wherein said stabilizer is employed in quantities of from about 20 ppm to about 250 ppm.
Claim 11
Dependent Claim 45 words
The process of claim 4 wherein the polyisocyanate is toluene diisocyanate which is distilled in the presence of from about 50 ppm to about 600 ppm of triphenyl phosphite and the stabilizer is present in quantities of from about 50 ppm to about 500 ppm.
Claim 12
Dependent Claim 15 words
The process of claim 5 wherein the polyisocyanate is an 80/20 mixture of 2,4-/2,6-toluene diisocyanate.
Claim 13
Dependent Claim 62 words
A polyisocyanate containing as a stabilizer against discoloration from about 10 ppm to about 250 ppm of a mixture comprising A. an organic phosphite selected from the group consisting of 1. triphenyl phosphite, 2. diphenylisodecyl phosphite, 3. trisnonylphenyl phosphite, 4. triisodecyl phosphite, 5. trilauryl phosphite, and 6. mixtures thereof; and B. a member of the group consisting of 1. o,o-di-n-octadecyl-3,5-di-tert-butyl-4-hydroxybenzylphosphonate, 2. tetrakis(methylene(3,5-di-tert-butyl-4-hydroxyhydrocinnamate))methane,
Claim 14
Dependent Claim 62 words
A polyisocyanate containing as a stabilizer against discoloration from about 10 ppm to about 250 ppm of a mixture comprising A. an organic phosphite selected from the group consisting of 1. triphenyl phosphite, 2. diphenylisodecyl phosphite, 3. trisnonylphenyl phosphite, 4. triisodecyl phosphite, 5. trilauryl phosphite, and 6. mixtures thereof; and B. a member of the group consisting of 1. o,o-di-n-octadecyl-3,5-di-tert-butyl-4-hydroxybenzylphosphonate, 2. tetrakis(methylene(3,5-di-tert-butyl-4-hydroxyhydrocinnamate))methane,
Claim 15
Dependent Claim 21 words
bis(2-(4-hydroxy-3,5-di-tert-butylphenyl)ethyl)sulfide, 4. octadecyl-3,5-di-tert-butyl-4-hydroxyhydrocinnamate, and 5. mixtures thereof; and wherein the equivalent ratio of B:A is from about 0.01:1 to about 10:1.
Claim 16
Dependent Claim 21 words
bis(2-(4-hydroxy-3,5-di-tert-butylphenyl)ethyl)sulfide, 4. octadecyl-3,5-di-tert-butyl-4-hydroxyhydrocinnamate, and 5. mixtures thereof; and wherein the equivalent ratio of B:A is from about 0.01:1 to about 10:1.
Claim 17
Dependent Claim 27 words
The composition of claim 7 wherein the polyisocyanate is toluene diisocyanate and the stabilizer is present in quantities of from about 25 ppm to about 250 ppm.
Claim 18
Dependent Claim 15 words
The composition of claim 8 wherein the polyisocyanate is an 80/20 mixture of 2,4-/2,6-toluene diisocyanate.
Claim 19
Dependent Claim 23 words
The composition of claim 9 wherein the stabilizer mixture is in an equivalent ratio of (B):(A) of from about 0.35:1 to about 1.45:1.
Claim 20
Dependent Claim 17 words
The composition of claim 10 wherein the stabilizer is a mixture of triphenyl phosphite and Component (B-2).
Claim 21
Dependent Claim 17 words
The composition of claim 10 wherein the stabilizer is a mixture of triphenyl phosphite and Component (B-3).
Claim 22
Dependent Claim 83 words
A process for preparing a polyisocyanate resistant to discoloration upon storage which comprises distilling said polyisocyanate in the presence of at least about 25 ppm of an organic phosphite and adding to the resultant distillate a stabilizer mixture comprising A. an organic phosphite selected from the group consisting of 1. triphenyl phosphite, 2. diphenylisodecyl phosphite, 3. trisnonylphenyl phosphite, 4. triisodecyl phosphite, 5. trilauryl phosphite, and 6. mixtures thereof; and B. a member of the group consisting of 1. o,o-di-n-octadecyl-3,5-di-tert-butyl-4-hydroxybenzylphosphonate, 2. tetrakis(methylene(3,5-di-tert-butyl-4-hydroxyhydrocinnamate))methane, 3. bis(2-(4-hydroxy-3,5-di-tert-butylphenyl)ethyl)sulfide,
Claim 23
Dependent Claim 83 words
A process for preparing a polyisocyanate resistant to discoloration upon storage which comprises distilling said polyisocyanate in the presence of at least about 25 ppm of an organic phosphite and adding to the resultant distillate a stabilizer mixture comprising A. an organic phosphite selected from the group consisting of 1. triphenyl phosphite, 2. diphenylisodecyl phosphite, 3. trisnonylphenyl phosphite, 4. triisodecyl phosphite, 5. trilauryl phosphite, and 6. mixtures thereof; and B. a member of the group consisting of 1. o,o-di-n-octadecyl-3,5-di-tert-butyl-4-hydroxybenzylphosphonate, 2. tetrakis(methylene(3,5-di-tert-butyl-4-hydroxyhydrocinnamate))methane, 3. bis(2-(4-hydroxy-3,5-di-tert-butylphenyl)ethyl)sulfide,
Claim 24
Dependent Claim 21 words
octadecyl-3,5-di-tert-butyl-4-hydroxyhydrocinnamate, and 5. mixtures thereof; and wherein the equivalent ratio of (B) : (A) is from about 0.01:1 to about 10:1.
Claim 25
Dependent Claim 21 words
octadecyl-3,5-di-tert-butyl-4-hydroxyhydrocinnamate, and 5. mixtures thereof; and wherein the equivalent ratio of (B) : (A) is from about 0.01:1 to about 10:1.
Claim 26
Dependent Claim 27 words
The composition of claim 13 wherein the polyisocyanate is toluene diisocyanate and the stabilizer is present in quantities of from about 25 ppm to about 250 ppm.
Claim 27
Dependent Claim 15 words
The composition of claim 14 wherein the polyisocyanate is an 80/20 mixture of 2,4-/2,6-toluene diisocyanate.
Claim 28
Dependent Claim 23 words
The composition of claim 15 wherein the stabilizer mixture is in an equivalent ratio of (B):(A) of from about 0.35:1 to about 1.45:1.
Claim 29
Dependent Claim 17 words
The composition of claim 16 wherein the stabilizer is a mixture of triphenyl phosphite and Component (B-2).
Claim 30
Dependent Claim 17 words
The composition of claim 16 wherein the stabilizer is a mixture of triphenyl phosphite and Component (B-3).

References Cited (Backward Citations)

US2950307A Cited
US2957903A Cited
US3367870A Cited
US3285855A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1980-12-19 1981-06-20 1981-12-20 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1984-12-19 1985-06-20 1985-12-20 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1988-12-19 1989-06-20 1989-12-20 $7700.00 Window Closed / Lapsed

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