US3929929A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Vinyl urethane resins
Assignee: Zeneca Inc
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Filing: 1973-05-29
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Granted: 1975-12-30
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Expires: 1993-05-29
Abstract
Abstract Improved vinyl urethane resins are disclosed. The resins are prepared by reacting a diol, a polyisocyanate, and a hydroxylterminated ester of acrylic or methacrylic acid wherein at least part of the excess functionality of the isocyanate is reduced by reaction with a diol.
Inventors
- 👤 Erich Kuehn
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-24 06:28
CPC Classifications
C; C08; C08G; C08G18/00; C08G18/06; C08G18/28; C08G18/67; C08G18/671; C08G18/672; C08G18/30; C08G18/32; C08G18/3203
Claims Analysis
Total Claims: 18
Claim 1
Independent Claim
224 words
A COMPOSITION COMPRISING: A. A VINLY URETHANE RESIN COMPRISING THE REACTION PRODUCT OT A DIOL, A POLYISOCYANATE HAVING A FUNCTIONALITY EQUAL TO FROM 2.1 TO ABOUT 3.0, AND A HYDROXYL TERMINATED ESTER OF ACRYLIC OR METHACRYLIC ACID; PROVODED THAT, (I) WHEN THE AMOUNT OF THE DIOL IS EQUAL TO UP TO 1 MOLE, THE AMOUNT OF THE POLYISOCYANATE IS EQUAL TO ABOUT 2 MOLES PER MOLE OF THE DIOL AND THE AMOUNT OF HYDROXYL TERMINATED ESTER IS EQUAL TO ABOUT 2 MOLES PER MOLE OF THE DIOL, (II) WHEN THE AMOUNT OF THE DIOL IS EQUAL TO GREATER THAN 1 MOLE, THE AMOUNT OF THE POLYISOCYANATE IS EQUAL TO ABOUT 1 MOLE PLUS 1 MOLE PER MOLE OF THE DIOL AND THE AMOUNT OF THE HYDROXYL TERMINATED ESTER IS EQUAL TO ABOUT 2 MOLES, AND (III) AT LEAST 50 PERCENT OF THE EXCESS FUNCTIONALITY OF THE POLYISOCYANATE IS REDUCED BY REACTION WITH THE DIOL AND, WHEN LESS THAN 100 PERCENT OF THE EXCESS FUNCTIONALITY OF THE POLYISOCYANATE IS REACTED WITH THE DIOL, AN ADDITIONAL HYDROXYLCONTAINING COMPOUND IS EMPLOYED IN AN AMOUNT SUFFICIENT TO INTRODUCE ADEQUATE HYDROXYL GROUPS TO REACT WITH ANY REMAINING ISOCYANATE FUNCTIONALITY; AND B. A MONOMER SELECTED FROM THE GROUP CONSISTING OF STYRENE, T-BTUYL STYRENEM ALPHA METHYL STYRENE, CHLOROSTYRENE, DIVINYL BENZENE, ACRYLIC ACID, DIMETHYL MALEATE, DIBUTYL FUMARATE, BUTYL METHACRYLATE, AND NONYL METHACRYLATE.
Claim 2
Dependent Claim
224 words
A COMPOSITION COMPRISING: A. A VINLY URETHANE RESIN COMPRISING THE REACTION PRODUCT OT A DIOL, A POLYISOCYANATE HAVING A FUNCTIONALITY EQUAL TO FROM 2.1 TO ABOUT 3.0, AND A HYDROXYL TERMINATED ESTER OF ACRYLIC OR METHACRYLIC ACID; PROVODED THAT, (I) WHEN THE AMOUNT OF THE DIOL IS EQUAL TO UP TO 1 MOLE, THE AMOUNT OF THE POLYISOCYANATE IS EQUAL TO ABOUT 2 MOLES PER MOLE OF THE DIOL AND THE AMOUNT OF HYDROXYL TERMINATED ESTER IS EQUAL TO ABOUT 2 MOLES PER MOLE OF THE DIOL, (II) WHEN THE AMOUNT OF THE DIOL IS EQUAL TO GREATER THAN 1 MOLE, THE AMOUNT OF THE POLYISOCYANATE IS EQUAL TO ABOUT 1 MOLE PLUS 1 MOLE PER MOLE OF THE DIOL AND THE AMOUNT OF THE HYDROXYL TERMINATED ESTER IS EQUAL TO ABOUT 2 MOLES, AND (III) AT LEAST 50 PERCENT OF THE EXCESS FUNCTIONALITY OF THE POLYISOCYANATE IS REDUCED BY REACTION WITH THE DIOL AND, WHEN LESS THAN 100 PERCENT OF THE EXCESS FUNCTIONALITY OF THE POLYISOCYANATE IS REACTED WITH THE DIOL, AN ADDITIONAL HYDROXYLCONTAINING COMPOUND IS EMPLOYED IN AN AMOUNT SUFFICIENT TO INTRODUCE ADEQUATE HYDROXYL GROUPS TO REACT WITH ANY REMAINING ISOCYANATE FUNCTIONALITY; AND B. A MONOMER SELECTED FROM THE GROUP CONSISTING OF STYRENE, T-BTUYL STYRENEM ALPHA METHYL STYRENE, CHLOROSTYRENE, DIVINYL BENZENE, ACRYLIC ACID, DIMETHYL MALEATE, DIBUTYL FUMARATE, BUTYL METHACRYLATE, AND NONYL METHACRYLATE.
Claim 3
Dependent Claim
14 words
A composition, as claimed in claim 1, wherein the diol has the following formula:
Claim 4
Dependent Claim
14 words
A composition, as claimed in claim 1, wherein the diol has the following formula:
Claim 5
Dependent Claim
20 words
A composition, as claimed in claim 1, wherein the hydroxyl-terminated ester of acrylic or methacrylic acid has the following formula:
Claim 6
Dependent Claim
19 words
A composition, as claimed in claim 1, wherein the hydroxyl-terminated ester of acrylic or methacrylic acid is hydroxyethyl metHacrylate.
Claim 7
Dependent Claim
14 words
A composition, as claimed in claim 1, wherein the polyisocyanate has the following formula:
Claim 8
Dependent Claim
47 words
A composition, as claimed in claim 1, wherein the excess functionality of the isocyanate is reacted with a mixture of a diol and a hydroxyl-terminated ester of acrylic or methacrylic acid, wherein at least 50% of the hydroxyl groups in said mixture are derived from the diol.
Claim 9
Dependent Claim
17 words
A composition, as claimed in claim 7, wherein the diol in said mixture has the following formula:
Claim 10
Dependent Claim
49 words
A composition, as claimed in claim 1, wherein the vinyl urethane resin comprises the reaction product of x moles of the diol, 2x moles of the polyisocyanate, and 2x moles of the hydroxyl terminated ester of acrylic or methacrylic acid, wherein x is equal to up to about 1.0.
Claim 11
Dependent Claim
50 words
A composition, as claimed in claim 1, wherein the vinyl urethane resin comprises the reaction product of y moles of the diol, y + 1 mole of the polyisocyanate, and 2 moles of the hydroxyl terminated ester of acrylic or methacrylic acid, wherein y is equal to at least 1.1.
Claim 12
Independent Claim
240 words
A method of preparing a solution of a vinyl urethane resin, said method comprising: a. preparing a prepolymer by reacting, in a vinyl or allyl monomer solvent selected from the group consisting of styrene, t-butyl styrene, alpha methyl styrene, chlorostyrene, divinyl benzene, acrylic acid, dimethyl maleate, dibutyl fumarate, butyl methacrylate, and nonyl methacrylate, a polyisocyanate having a functionality equal to from 2.1 to about 3.0 with a diol or a mixture of a diol and a monohydroxyl compound wherein at least 50 percent of the hydroxyl groups are derived from the diol, the amount of the diol or mixture of diol and monohydroxyl compound being sufficient to reduce the functionality of the polyisocyanate to about 2.0; and b. reacting said prepolymer in a single step with a mixture of a diol and a hydroxyl terminated ester of acrylic or methacrylic acid; provided that (i) when the amount of the diol is equal to up to 1 mole the amount of the prepolymer is equal to about 2 moles per mole of the diol and the amount of the hydroxyl terminated ester is equal to about 2 moles per mole of the diol, and (ii) when the amount of the diol is equal to greater than 1 mole, the amount of the prepolymer is equal to about 1 mole plus 1 mole per mole of the diol and the amount of the hydroxyl terminated ester is equal to about 2 moles.
Claim 13
Independent Claim
240 words
A method of preparing a solution of a vinyl urethane resin, said method comprising: a. preparing a prepolymer by reacting, in a vinyl or allyl monomer solvent selected from the group consisting of styrene, t-butyl styrene, alpha methyl styrene, chlorostyrene, divinyl benzene, acrylic acid, dimethyl maleate, dibutyl fumarate, butyl methacrylate, and nonyl methacrylate, a polyisocyanate having a functionality equal to from 2.1 to about 3.0 with a diol or a mixture of a diol and a monohydroxyl compound wherein at least 50 percent of the hydroxyl groups are derived from the diol, the amount of the diol or mixture of diol and monohydroxyl compound being sufficient to reduce the functionality of the polyisocyanate to about 2.0; and b. reacting said prepolymer in a single step with a mixture of a diol and a hydroxyl terminated ester of acrylic or methacrylic acid; provided that (i) when the amount of the diol is equal to up to 1 mole the amount of the prepolymer is equal to about 2 moles per mole of the diol and the amount of the hydroxyl terminated ester is equal to about 2 moles per mole of the diol, and (ii) when the amount of the diol is equal to greater than 1 mole, the amount of the prepolymer is equal to about 1 mole plus 1 mole per mole of the diol and the amount of the hydroxyl terminated ester is equal to about 2 moles.
Claim 14
Dependent Claim
12 words
A method, as claimed in claim 11, wherein the solvent is styrene.
Claim 15
Independent Claim
241 words
A method of preparing a solution of a vinyl urethane resin, said method comprising reacting, in one step and in a vinyl or allyl monomer solvent, selected from the group consisting of styrene, t-butyl styrene, alpha methyl styrene, chlorostyrene, divinyl benzene, acrylic acid, dimethyl maleate, dibutyl fumarate, butyl methacrylate, and nonyl methacrylate, a diol, a hydroxyl terminated ester of acrylic or methacrylic acid, and a polyisocyanate having a functionality equal to from 2.1 to about 3.0; provided that (i) when the amount of the diol is equal to up to 1 mole, the amount of the polyisocyanate is equal to about 2 moles per mole of the diol and the amount of the hydroxyl terminated ester is equal to about 2 moles per mole of the diol, and (ii) when the amount of the diol is equal to greater than 1 mole, the amount of the polyisocyanate is equal to about 1 mole plus 1 mole per mole of the diol and the amount of the hydroxyl terminated ester is equal to about 2 moles, and (iii) there is also included an additional amOunt of diol sufficient to react with at least 50 percent of the excess functionality of the polyisocyanate and, when less than 100 percent of the excess functionality of the polyisocyanate is reacted with the diol an additional hydroxyl-containing compound is employed in an amount sufficient to introduce adequate hydroxyl groups to react with any remaining isocyanate functionality.
Claim 16
Independent Claim
241 words
A method of preparing a solution of a vinyl urethane resin, said method comprising reacting, in one step and in a vinyl or allyl monomer solvent, selected from the group consisting of styrene, t-butyl styrene, alpha methyl styrene, chlorostyrene, divinyl benzene, acrylic acid, dimethyl maleate, dibutyl fumarate, butyl methacrylate, and nonyl methacrylate, a diol, a hydroxyl terminated ester of acrylic or methacrylic acid, and a polyisocyanate having a functionality equal to from 2.1 to about 3.0; provided that (i) when the amount of the diol is equal to up to 1 mole, the amount of the polyisocyanate is equal to about 2 moles per mole of the diol and the amount of the hydroxyl terminated ester is equal to about 2 moles per mole of the diol, and (ii) when the amount of the diol is equal to greater than 1 mole, the amount of the polyisocyanate is equal to about 1 mole plus 1 mole per mole of the diol and the amount of the hydroxyl terminated ester is equal to about 2 moles, and (iii) there is also included an additional amOunt of diol sufficient to react with at least 50 percent of the excess functionality of the polyisocyanate and, when less than 100 percent of the excess functionality of the polyisocyanate is reacted with the diol an additional hydroxyl-containing compound is employed in an amount sufficient to introduce adequate hydroxyl groups to react with any remaining isocyanate functionality.
Claim 17
Dependent Claim
12 words
A method, as claimed in claim 13, wherein the solvent is styrene.
Claim 18
Dependent Claim
12 words
A composition, as claimed in claim 1, wherein the monomer is styrene.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1978-12-29 | 1979-06-30 | 1979-12-30 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1982-12-29 | 1983-06-30 | 1983-12-30 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1986-12-29 | 1987-06-30 | 1987-12-30 | $7700.00 | Window Closed / Lapsed |