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US3711571A Expired / Lapsed US ⏱️ 0.0 years remaining

Curable blend of blocked and unblocked polyurethanes

Assignee: NL SPENCER KELLOG Inc
•
Filing: 1970-07-09
•
Granted: 1973-01-16
•
Expires: 1990-07-09
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Abstract

Abstract There are disclosed curable polyurethane compositions comprising: I. A normally-liquid, free isocyanate-blocked urethane prepolymer composition comprising the reaction product of (A) a diisocyanate-polyol urethane prepolymer containing free isocyanate groups, and (B) an isocyanate-reactive oxime, said reaction product being made by reaction of an essentially stoichiometric equivalent of (B) per equivalent of free isocyanate in (A); and II. an elastomeric, polyamine-extended polyurethane comprising the reaction product of (A) a diisocyanate-polyol urethane prepolymer containing free isocyanate groups, and (B) an isocyanate-reactive polyamine, said reaction product being made by the reaction of an essentially stoichiometric equivalent of (B) per equivalent of free isocyanate in (A). The compositions are normally cured at temperatures above room temperature, especially above about 70* C. and advantageously above about 130* or even above about 145* C. Additionally, the cured compositions are useful as coatings for both flexible and rigid articles such as textiles, leather, vinyl and rubber materials, metal, wood are rigid plastic materials. In a preferred embodiment, the oxime in (I) is methyl ethyl ketoxime and the polyamine in (II) is 1-amino-3-aminomethyl-3,5,5-trimethyl cyclohexane, while the urethane prepolymer in both (I) and (II) is prepared from toluene diisocyanate or 1-isocyanato-3isocyanato methyl-3,5,5-trimethyl cyclohexane with trimethyol propane as the polyol in (I) and a polyester of a glycol and adipic acid as the polyol in (II). The coatings prepared from the compositions of this invention are normally highly resistant to abrasion and chemical attack.

Inventors

  • 👤 B Farah

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-24 14:49
CPC Classifications
C; C08; C08G; C08G18/00; C08G18/06; C08G18/08; C08G18/10; C08G18/12

Claims Analysis

Total Claims: 35
Claim 1
Independent Claim 48 words
A NORMALLY-LIQUID, FREE ISOCYANATE-BLOCKED URETHANE PREPOLYMER COMPOSITION COMPRISING THE REACTION PRODUCT OF (A) A DIISOCYANATE-POLYOL URETHANE PREPOLYMER CONTAINING FREE ISOCYANATE GROUPS, AND (B) AN ISOCYANATE-REACTIVE OXIME, SAID REACTION PRODUCT BEING MADE BY REACTION OF AN ESSENTIALLY STOICHIOMETRIC EQUIVALENT OF (B) PER EQUIVALENT OF FREE ISOCYANATE IN (A); AND
Claim 2
Dependent Claim 48 words
A NORMALLY-LIQUID, FREE ISOCYANATE-BLOCKED URETHANE PREPOLYMER COMPOSITION COMPRISING THE REACTION PRODUCT OF (A) A DIISOCYANATE-POLYOL URETHANE PREPOLYMER CONTAINING FREE ISOCYANATE GROUPS, AND (B) AN ISOCYANATE-REACTIVE OXIME, SAID REACTION PRODUCT BEING MADE BY REACTION OF AN ESSENTIALLY STOICHIOMETRIC EQUIVALENT OF (B) PER EQUIVALENT OF FREE ISOCYANATE IN (A); AND
Claim 3
Dependent Claim 29 words
The composition of claim 1 in which there are about 0.1 to 50 nitrogen atoms having at least one hydrogen atom per equivalent of blocked isocyanate group in (I).
Claim 4
Dependent Claim 42 words
The composition of claim 1 wherein the aliphatic polyol in the reaction product of (I) has a molecular weight of up to about 200 and is composed to a major molar extent of polyol of at least three hydroxy groups per molecule.
Claim 5
Dependent Claim 17 words
The composition of claim 3 wherein the polyol in the reaction product of (I) is trimethylol propane.
Claim 6
Dependent Claim 27 words
The composition of claim 1 wherein the aliphatic polyol in the polyamine-extended polyurethane of (II) is polyester or polyether glycol of about 750 to 4,000 molecular weight.
Claim 7
Dependent Claim 31 words
The composition of claim 1 wherein the isocyanate reactive oxime of (I) has the formula wherein R is an essentially hydrocarbyl group of up to about 20 carbon atoms or hydrogen.
Claim 8
Dependent Claim 14 words
The composition of claim 6 wherein the R groups are lower alkyl or hydrogen.
Claim 9
Dependent Claim 12 words
The composition of claim 7 wherein each R group is lower alkyl.
Claim 10
Dependent Claim 32 words
The composition of claim 3 wherein the isocyanate reactive oxime of (I) has the formula wherein R is an essentially hydrocarbyl group of up to about 20 carbon atoms or is hydrogen.
Claim 11
Dependent Claim 14 words
The composition of claim 9 wherein the R groups are lower alkyl or hydrogen.
Claim 12
Dependent Claim 174 words
AN ELASTOMERIC, POLYAMINE-EXTENDED POLYURETHANE COMPRISING THE REACTION PRODUCT OF (A) A DIISOCYANATE-POLYOL URETHANE PREPOLYMER CONTAINING FREE ISOCYANATE GROUPS, AND (B) AN ISOCYANATE-REACTIVE POLYAMINE, SAID REACTION PRODUCT BEING MADE BY THE REACTION OF AN ESSENTIALLY STOICHIOMETRIC EQUIVALENT OF (B) PER EQUIVALENT OF FREE ISOCYANATE IN (A). THE CONDITIONS ARE NORMALLY CURED AT TEMPERATURES ABOVE ROOM TEMPERATURE, ESPECIALLY ABOVE ABOUT 70* C. AND ADVANTAGEOUSLY ABOVE ABOUT 130* OR EVEN ABOVE ABOUT 145*C ADDITIONALLY, THE CURED COMPOSITIONS ARE USEFUL AS COATINGS FOR BOTH FLEXIBLE AND RIGID ARTICLES SUCH AS TEXTILES, LEATHER VINYL AND RUBBER MATERIALS, METAL, WOOD ARE RIGID PLASTIC MATERIALS. IN A PREFERRED EMBODIMENT, THE OXMINE IN (1) IS METHYL ETHYL KETOXIME AND THE POLYAMINE IN (11) IS 1-AMINO-3AMINOMETHYL-3,5,5-TRIMETHYL CYCLOHEXANE WHILE THE URETHANE PREPOLYMER IN BOTH (1) AND (11) IS PREPARED TOLUENE DIISOCYANATE OR 1-ISOCYANATO-3-ISOCYANATO METHYL-3,5,5-TRIMETHYL CYCLOHEXANE WITH TRIMETHYOL PROPANE AS THE POLYOL IN (1) AND A POLYESTER A GLYCOL AND ADIPIC ACID AS THE POLYOL IN (11). THE COATINGS PREPARED FROM THE COMPOSITIONS OF THIS INVENTION ARE NORMALY HIGHLY RESISTANT TO ABRASION AND CHEMICAL ATTACK.
Claim 13
Dependent Claim 174 words
AN ELASTOMERIC, POLYAMINE-EXTENDED POLYURETHANE COMPRISING THE REACTION PRODUCT OF (A) A DIISOCYANATE-POLYOL URETHANE PREPOLYMER CONTAINING FREE ISOCYANATE GROUPS, AND (B) AN ISOCYANATE-REACTIVE POLYAMINE, SAID REACTION PRODUCT BEING MADE BY THE REACTION OF AN ESSENTIALLY STOICHIOMETRIC EQUIVALENT OF (B) PER EQUIVALENT OF FREE ISOCYANATE IN (A). THE CONDITIONS ARE NORMALLY CURED AT TEMPERATURES ABOVE ROOM TEMPERATURE, ESPECIALLY ABOVE ABOUT 70* C. AND ADVANTAGEOUSLY ABOVE ABOUT 130* OR EVEN ABOVE ABOUT 145*C ADDITIONALLY, THE CURED COMPOSITIONS ARE USEFUL AS COATINGS FOR BOTH FLEXIBLE AND RIGID ARTICLES SUCH AS TEXTILES, LEATHER VINYL AND RUBBER MATERIALS, METAL, WOOD ARE RIGID PLASTIC MATERIALS. IN A PREFERRED EMBODIMENT, THE OXMINE IN (1) IS METHYL ETHYL KETOXIME AND THE POLYAMINE IN (11) IS 1-AMINO-3AMINOMETHYL-3,5,5-TRIMETHYL CYCLOHEXANE WHILE THE URETHANE PREPOLYMER IN BOTH (1) AND (11) IS PREPARED TOLUENE DIISOCYANATE OR 1-ISOCYANATO-3-ISOCYANATO METHYL-3,5,5-TRIMETHYL CYCLOHEXANE WITH TRIMETHYOL PROPANE AS THE POLYOL IN (1) AND A POLYESTER A GLYCOL AND ADIPIC ACID AS THE POLYOL IN (11). THE COATINGS PREPARED FROM THE COMPOSITIONS OF THIS INVENTION ARE NORMALY HIGHLY RESISTANT TO ABRASION AND CHEMICAL ATTACK.
Claim 14
Dependent Claim 12 words
The composition of claim 10 wherein each R group is lower alkyl.
Claim 15
Dependent Claim 13 words
The composition of claim 1 wherein the isocyanate-reactive polyamine in (II) is diamine.
Claim 16
Dependent Claim 15 words
The composition of claim 12 wherein the isocyanate-reactant polyamine in (II) is aliphatic diprimary diamine.
Claim 17
Dependent Claim 10 words
The composition of claim 13 wherein the diamine is 1-amino-3-aminomethyl-3,5,5-trimethylcyclohexane.
Claim 18
Dependent Claim 18 words
The composition of claim 1 wherein at least one of the diisocyanates of (I) and (II) is aromatic.
Claim 19
Dependent Claim 15 words
The composition of claim 1 wherein both the diisocyanates of (I) and (II) are aromatic.
Claim 20
Dependent Claim 16 words
A cured composition of claim 1, said composition having been cured at above about 100* C.
Claim 21
Dependent Claim 16 words
A cured composition of claim 2, said composition having been cured at above about 100* C.
Claim 22
Dependent Claim 16 words
A cured composition of claim 3, said composition having been cured at above about 100* C.
Claim 23
Dependent Claim 16 words
A cured composition of claim 4, said composition having been cured at above about 100* C.
Claim 24
Dependent Claim 16 words
A cured composition of claim 5, said composition having been cured at above about 100* C.
Claim 25
Dependent Claim 16 words
A cured composition of claim 6, said composition having been cured at above about 100* C.
Claim 26
Dependent Claim 16 words
A cured composition of claim 7, said composition having been cured at above about 100* C.
Claim 27
Dependent Claim 16 words
A cured composition of claim 8, said composition having been cured at above about 100* C.
Claim 28
Dependent Claim 16 words
A cured composition of claim 9, said composition having been cured at above about 100* C.
Claim 29
Dependent Claim 16 words
A cured composition of claim 10, said composition having been cured at above about 100* C.
Claim 30
Dependent Claim 16 words
A cured composition of claim 11, said composition having been cured at above about 100* C.
Claim 31
Dependent Claim 16 words
A cured composition of claim 12, said composition having been cured at above about 100* C.
Claim 32
Dependent Claim 16 words
A cured composition of claim 13, said composition having been cured at above about 100* C.
Claim 33
Dependent Claim 16 words
A cured composition of claim 14, said composition having been cured at above about 100* C.
Claim 34
Dependent Claim 16 words
A cured composition of claim 15, said composition having been cured at above about 100* C.
Claim 35
Dependent Claim 16 words
A cured composition of claim 16, said composition having been cured at above about 100* C.

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1976-01-16 1976-07-17 1977-01-16 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1980-01-16 1980-07-17 1981-01-16 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1984-01-16 1984-07-17 1985-01-16 $7700.00 Window Closed / Lapsed

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