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US3917570A Expired / Lapsed US ⏱️ 0.0 years remaining

Polyurethane polyester-polyol compositions modified with an alkylenimine

Assignee: PPG Industries Inc
•
Filing: 1973-05-16
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Granted: 1975-11-04
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Expires: 1993-05-16
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Abstract

Abstract Compositions useful as coating compositions comprise the reaction product of a polyurethane polyol which contains acidic carboxyl groups with an alkylenimine. Particularly desirable coatings are produced by further combining the imine-modified polyurethane polyols with aminoplast resins. The compositions are characterized by improved pigment wetting properties and provide coatings having improved low temperature flexibility and increased adhesion.

Inventors

  • 👤 Wen-Hsuan Chang
  • 👤 Roger L Scriven
  • 👤 Paul J Prucnal

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-01 23:06
CPC Classifications
C; C08; C08G; C08G18/00; C08G18/06; C08G18/83; C08G18/833; C09; C09D; C09D175/00; C09D175/04

Claims Analysis

Total Claims: 18
Claim 1
Independent Claim 77 words
A COATING COMPOSITION COMPRISING THE REACTION PRODUCT OF: A. AN UNGELLED, CARBOXYL-HYDROXYL-CONTAINING URETHANE REACTION PRODUCT HAVING AN ACID VALUE OF AT LEAST ABOUT 1 AND HAVING AN INTRINSIC VISCOSITY OF 1.0 DECILITERS PER GRAM OR LESS, AND B. AN AKYLENIMINE, WHEREIN SAID ALKYLENIMINE HAS 2 OR 3 CARBON ATOMS PER ALKYLENIMINE RING, WHERBY AT LAST ABOUT 0.03 PERCENT BY WEIGHT OF ACIDIC GROUPS BASED ON TOTAL WEIGHT OF THE URETHANE REACTION PRODUCT ARE REACTED WITH THE ALKYLENIMINE.
Claim 2
Dependent Claim 77 words
A COATING COMPOSITION COMPRISING THE REACTION PRODUCT OF: A. AN UNGELLED, CARBOXYL-HYDROXYL-CONTAINING URETHANE REACTION PRODUCT HAVING AN ACID VALUE OF AT LEAST ABOUT 1 AND HAVING AN INTRINSIC VISCOSITY OF 1.0 DECILITERS PER GRAM OR LESS, AND B. AN AKYLENIMINE, WHEREIN SAID ALKYLENIMINE HAS 2 OR 3 CARBON ATOMS PER ALKYLENIMINE RING, WHERBY AT LAST ABOUT 0.03 PERCENT BY WEIGHT OF ACIDIC GROUPS BASED ON TOTAL WEIGHT OF THE URETHANE REACTION PRODUCT ARE REACTED WITH THE ALKYLENIMINE.
Claim 3
Dependent Claim 14 words
A coating composition according to claim 1, wherein said alkylenimine is of the formula:
Claim 4
Dependent Claim 21 words
A coating composition according to claim 2, wherein said alkylenimine is selected from the group consisting of ethylenimine, 1,2-propylenimine, and N-hydroxyethylethylenimine.
Claim 5
Dependent Claim 74 words
A coating composition according to claim 2, wherein said urethane reaction product is the reaction product of an organic polyisocyanate and a polyhydric material, with the major portion of said polyhydric material being selected from the group consisting of polyether polyols, polyester polyols, and mixtures thereof and wherein said polyhydric material contains no more than about 1 gram mole of compounds having a functionality of 3 or more per 500 grams of polyhydric material.
Claim 6
Dependent Claim 68 words
A coating composition according to claim 4 wherein the major portion of said polyhydric material is a polyester polyol formed from an alcohol component having an average functionality of at least about 1.9 and an acid component consisting essentially of one or more monomeric carboxylic acids or anhydrides having 2 to 14 carbon atoms per molecule, said acid component having an average functionality of at least about 1.9.
Claim 7
Dependent Claim 28 words
A coating composition according to claim 4 wherein the major portion of said polyhydric material is a polyether polyol having a hydroxyl equivalent of at least about 100.
Claim 8
Independent Claim 121 words
The method of producing a coating composition of improved pigment wetting properties comprising: A. forming an ungelled, hydroxyl-containing urethane reaction product having an intrinsic viscosity of 1.0 deciliter per gram or less; B. reacting the urethane reaction product with an acidic carboxyl source material, with said source material being present in an amount sufficient to yield a carboxyl-hydroxyl-containing urethane reaction product containing at least 0.075 percent by weight of acidic carboxyl groups; and C. reacting the thus-formed carboxyl-hydroxyl-containing urethane reaction product with an alkylenimine, said alkylenimine having 2 or 3 carbon atoms per alkylenimine ring; whereby at least about 0.03 percent by weight of acidic groups, based on total weight of the carboxyl-hydroxyl-containing urethane reaction product are reacted with the imine.
Claim 9
Independent Claim 121 words
The method of producing a coating composition of improved pigment wetting properties comprising: A. forming an ungelled, hydroxyl-containing urethane reaction product having an intrinsic viscosity of 1.0 deciliter per gram or less; B. reacting the urethane reaction product with an acidic carboxyl source material, with said source material being present in an amount sufficient to yield a carboxyl-hydroxyl-containing urethane reaction product containing at least 0.075 percent by weight of acidic carboxyl groups; and C. reacting the thus-formed carboxyl-hydroxyl-containing urethane reaction product with an alkylenimine, said alkylenimine having 2 or 3 carbon atoms per alkylenimine ring; whereby at least about 0.03 percent by weight of acidic groups, based on total weight of the carboxyl-hydroxyl-containing urethane reaction product are reacted with the imine.
Claim 10
Dependent Claim 12 words
The method of claim 7 wherein said alkylenimine is of the formula:
Claim 11
Dependent Claim 19 words
The method of claim 8 wherein said alkylenimine is selected from the group consisting of ethylenimiNe, 1,2-propylenimine, and N-hydroxyethylethylenimine.
Claim 12
Dependent Claim 24 words
The method of claim 8 wherein said acidic carboxyl source material is selected from the group consisting of carboxyl acid anhydrides and carboxyl polyacids.
Claim 13
Dependent Claim 71 words
The method of claim 10 wherein said urethane reaction product is the reaction product of an organic polyisocyanate and a polyhydric material with the major portion of said polyhydric material being selected from the group consisting of polyether polyols, polyester polyols, and mixtures thereof and wherein said polyhydric material contains no more than about 1 gram-mole of compounds having a functionality of 3 or more per 500 grams of polyhydric material.
Claim 14
Independent Claim 170 words
The method of producing a coating composition oof improved pigment-wetting properties comprising: A. reacting an organic polyisocyanate with a polyhydric material, wherein the major portion of said polyhydric material is selected from the group consisting of polyether polyols, polyester polyols, and mixtures thereof, and wherein said polyhydric material contains no more than about 1 grammole of compounds having a functionality of 3 or more per 500 grams of polyhydric material; B. reacting an acidic carboxyl source material with the polyisocyanate and the polyhydric material with said source material being present in an amount sufficient to produce an acidic carboxyl group content of at least 0.075 percent by weight; C. terminating the reaction when the intrinsic viscosity is 1.0 deciliter per gram or less; and D. reacting the thus-formed carboxyl-hydroxyl-containing urethane reaction product with an alkylenimine said alkylenimine having 2 or 3 carbon atoms per alkylenimine ring; whereby at least 0.3 percent by weight of the acidic group based on total weight of the carboxyl-hydroxyl-containing reaction product reacted with the alkylenimine.
Claim 15
Independent Claim 170 words
The method of producing a coating composition oof improved pigment-wetting properties comprising: A. reacting an organic polyisocyanate with a polyhydric material, wherein the major portion of said polyhydric material is selected from the group consisting of polyether polyols, polyester polyols, and mixtures thereof, and wherein said polyhydric material contains no more than about 1 grammole of compounds having a functionality of 3 or more per 500 grams of polyhydric material; B. reacting an acidic carboxyl source material with the polyisocyanate and the polyhydric material with said source material being present in an amount sufficient to produce an acidic carboxyl group content of at least 0.075 percent by weight; C. terminating the reaction when the intrinsic viscosity is 1.0 deciliter per gram or less; and D. reacting the thus-formed carboxyl-hydroxyl-containing urethane reaction product with an alkylenimine said alkylenimine having 2 or 3 carbon atoms per alkylenimine ring; whereby at least 0.3 percent by weight of the acidic group based on total weight of the carboxyl-hydroxyl-containing reaction product reacted with the alkylenimine.
Claim 16
Dependent Claim 12 words
The method of claim 12 wherein said alkylenimine is of the formula:
Claim 17
Dependent Claim 19 words
THE METHOD OF CLAIM 13 WHEREIN SAID ALKYLENIMINE IS SELECTED FROM THE GROUP CONSISTING OF ETHYLENIMINE, 1,2PROPYLENIMINE AND N-HYDROXYETHYLETHYLENIMINE.
Claim 18
Dependent Claim 27 words
The method of claim 13 wherein said acidic carboxyl source material is selected from the group consisting of tartaric acid, glycolic acid, dimethylolpropionic acid and acid-containing polyesters.

References Cited (Backward Citations)

US2915480A Cited
US3054757A Cited
US3705076A Cited
US3290416A Cited
US3290417A Cited
US3658939A Cited
US3678013A Cited
US3715341A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1978-11-03 1979-05-05 1979-11-04 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1982-11-03 1983-05-05 1983-11-04 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1986-11-03 1987-05-05 1987-11-04 $7700.00 Window Closed / Lapsed

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