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US3888831A Expired / Lapsed US ⏱️ 0.0 years remaining

Curing with complexes of selected diamines and alkali metal salts

Assignee: Uniroyal Chemical Co Inc
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Filing: 1973-10-01
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Granted: 1975-06-10
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Expires: 1993-10-01
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Abstract

Abstract Amine-curable polymers or prepolymers are cured effectively by a curing agent which is a complex of 4,4''-methylene dianiline and/or racemic 2,3-di-(4-aminophenyl) butane and selected alkali metal salts including sodium chloride which complex is used in conjunction with a polarizable compound such as benzene, or a polar compound containing no reactive hydrogens, such as acetone.

Inventors

  • 👤 Irving Charles Kogon

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-27 16:57
CPC Classifications
C; C08; C08K; C08K5/00; C08G; C08G18/00; C08G18/06; C08G18/08; C08G18/10

Claims Analysis

Total Claims: 30
Claim 1
Independent Claim 17 words
IN A PROCESS FOR CURING AN AMINE-CURABLE POLYMER OR PREPOLYMER WITH A CURING AGENT WHICH IS EITHER
Claim 2
Dependent Claim 17 words
IN A PROCESS FOR CURING AN AMINE-CURABLE POLYMER OR PREPOLYMER WITH A CURING AGENT WHICH IS EITHER
Claim 3
Dependent Claim 35 words
A COMPLEX OF 4,4'' -METHYLENE DIANILINE AND A SALT SELECTED FROM THE GROUP CONSISTING OF SODIUM CHLORIDE, SODIUM BROMIDE, SODIUM IODIDE, LITHIUM NITRITE, AND SOLITHIUM BROMIDE, LITHIUM IODIDE, LITHIUM NITRITE, AND SO DIUM CYANIDE, OR
Claim 4
Dependent Claim 35 words
A COMPLEX OF 4,4'' -METHYLENE DIANILINE AND A SALT SELECTED FROM THE GROUP CONSISTING OF SODIUM CHLORIDE, SODIUM BROMIDE, SODIUM IODIDE, LITHIUM NITRITE, AND SOLITHIUM BROMIDE, LITHIUM IODIDE, LITHIUM NITRITE, AND SO DIUM CYANIDE, OR
Claim 5
Dependent Claim 140 words
A COMPLEX OF RACEMIC 2,3-DI(4-AMINOPHENYL) BUTANE WITH A SALT SELECTED FROM THE GROUP CONSISTING OF SODIUM CHLORIDE, SODIUM BROMIDE, POTASSIUM IODIDE, RUBIDIUM CHLORIDE, POTASSIUM BROMIDE, POTASSUM IODIDE, RUBIDIUM CHLORIDE, RUBIDIUM BROMIDE, RUBIDIUM IODIDE, CESIUM CHLORIDE, CESIUM BROMIDE AND CESIUM IODIDE, THE RATIO OF SAID DIANILINE OR SAID BUTANE TO SAID SALT IN THE COMPLEX BEING 3 MOLES TO 1 MOLE, THE IMPROVEMENT COMPRISING EMPLOYING SAID CURING AGENT IN CONJUNCTION WITH A POLAR OR POLARIZABLE COMPOUND HAVING NO REACTIVE HYDROGEN AND SELECTED FOM (A) COMPOUNDS HAVING DIPOLE MOMENTS IN EXCESS OF 0.4 DEBYE IN WHICH THERE ARE NO MORE THAN A TOTAL OF EIGHT CH3-, CH2, OR TERTIARY CARBON RADICALS PER POLAR GROUP CONTAINED IN THE COMPOUND, AND (B) BENZENE AND BIPHENYL, SAID POLAR OR POLARIZABLE COMPOUND REPRESENTING ABOUT 0.25-25% BY WEIGHT OF THE TOTAL WEIGHT OF COMPLEX AND POLAR COMPOUND.
Claim 6
Dependent Claim 140 words
A COMPLEX OF RACEMIC 2,3-DI(4-AMINOPHENYL) BUTANE WITH A SALT SELECTED FROM THE GROUP CONSISTING OF SODIUM CHLORIDE, SODIUM BROMIDE, POTASSIUM IODIDE, RUBIDIUM CHLORIDE, POTASSIUM BROMIDE, POTASSUM IODIDE, RUBIDIUM CHLORIDE, RUBIDIUM BROMIDE, RUBIDIUM IODIDE, CESIUM CHLORIDE, CESIUM BROMIDE AND CESIUM IODIDE, THE RATIO OF SAID DIANILINE OR SAID BUTANE TO SAID SALT IN THE COMPLEX BEING 3 MOLES TO 1 MOLE, THE IMPROVEMENT COMPRISING EMPLOYING SAID CURING AGENT IN CONJUNCTION WITH A POLAR OR POLARIZABLE COMPOUND HAVING NO REACTIVE HYDROGEN AND SELECTED FOM (A) COMPOUNDS HAVING DIPOLE MOMENTS IN EXCESS OF 0.4 DEBYE IN WHICH THERE ARE NO MORE THAN A TOTAL OF EIGHT CH3-, CH2, OR TERTIARY CARBON RADICALS PER POLAR GROUP CONTAINED IN THE COMPOUND, AND (B) BENZENE AND BIPHENYL, SAID POLAR OR POLARIZABLE COMPOUND REPRESENTING ABOUT 0.25-25% BY WEIGHT OF THE TOTAL WEIGHT OF COMPLEX AND POLAR COMPOUND.
Claim 7
Dependent Claim 140 words
a complex of racemic 2,3-di(4-aminophenyl) butane with a salt selected from the group consisting of sodium chloride, sodium bromide, sodium iodide, potassium chloride, potassium bromide, potassium iodide, rubidium chloride, rubidium bromide, rubidium iodide, cesium chloride, cesium bromide and cesium iodide; the ratio of said dianiline or said butane to said salt in the complex being 3 moles to 1 mole, the improvement comprising employing said curing agent in conjunction with a polar or polarizable compound having no reactive hydrogen and selected from (A) compounds having dipole moments in excess of 0.4 debye in which there are no more than a total of eight CH3-, CH2, or tertiary carbon radicals per polar group contained in the compound, and (B) benzene and biphenyl; said polar or polarizable compound representing about 0.25-25% by weight of the total weight of complex and polar compound.
Claim 8
Dependent Claim 140 words
a complex of racemic 2,3-di(4-aminophenyl) butane with a salt selected from the group consisting of sodium chloride, sodium bromide, sodium iodide, potassium chloride, potassium bromide, potassium iodide, rubidium chloride, rubidium bromide, rubidium iodide, cesium chloride, cesium bromide and cesium iodide; the ratio of said dianiline or said butane to said salt in the complex being 3 moles to 1 mole, the improvement comprising employing said curing agent in conjunction with a polar or polarizable compound having no reactive hydrogen and selected from (A) compounds having dipole moments in excess of 0.4 debye in which there are no more than a total of eight CH3-, CH2, or tertiary carbon radicals per polar group contained in the compound, and (B) benzene and biphenyl; said polar or polarizable compound representing about 0.25-25% by weight of the total weight of complex and polar compound.
Claim 9
Dependent Claim 49 words
The process of claim 1 wherein said curing agent is a complex of 3 moles of 4,4''-methylene dianiline and 1 mole of a salt selected from the group consisting of sodium chloride, sodium bromide, sodium iodide, sodium nitrite, lithium chloride, lithium bromide, lithium iodide, lithium nitrite and sodium cyanide.
Claim 10
Dependent Claim 122 words
a complex selected from the group consisting of (a) racemic 2,3-di (4-aminophenyl) butane and a salt selected from the group consisting of sodium chloride, sodium bromide, sodium iodide, potassium chloride, potassium bromide, potsassium iodide, rubidium chloride, rubidium bromide, rubidium iodide, cesium chloride, cesium bromide and cesium iodide, and (b) 4, 4''-methylene dianiline and a salt selected from the group consisting of sodium chloride, sodium bromide, sodium iodide, sodium nitrite, lithium chloride, lithium bromide, lithium iodide, lithium nitrite and sodium cyanide, the ratio of said dianiline and said 2,3-di(4-aminophenyl) butane to said salt in said complexes being 3 moles to 1 mole; said polar or polarizable compound representing about 0.25 to 25% by weight of the total weight of complex and polar compound.
Claim 11
Dependent Claim 122 words
a complex selected from the group consisting of (a) racemic 2,3-di (4-aminophenyl) butane and a salt selected from the group consisting of sodium chloride, sodium bromide, sodium iodide, potassium chloride, potassium bromide, potsassium iodide, rubidium chloride, rubidium bromide, rubidium iodide, cesium chloride, cesium bromide and cesium iodide, and (b) 4, 4''-methylene dianiline and a salt selected from the group consisting of sodium chloride, sodium bromide, sodium iodide, sodium nitrite, lithium chloride, lithium bromide, lithium iodide, lithium nitrite and sodium cyanide, the ratio of said dianiline and said 2,3-di(4-aminophenyl) butane to said salt in said complexes being 3 moles to 1 mole; said polar or polarizable compound representing about 0.25 to 25% by weight of the total weight of complex and polar compound.
Claim 12
Dependent Claim 17 words
The process of claim 1 wherein said prepolymer or polymer is a urethane containing free isocyanato groups.
Claim 13
Dependent Claim 16 words
The process of claim 3 wherein said complex is derived from 4,4''-methylene dianiline and sodium chloride.
Claim 14
Dependent Claim 16 words
The process of claim 3 wherein said complex is derived from 4,4''-methylene dianiline and lithium chloride.
Claim 15
Dependent Claim 31 words
The process of claim 3 wherein said polar compound (A) is selected from the group consisting of esters, ketones, ethers, halogenated hydrocarbons, tertiary amines, fully substituted amides, sulfones, sulfoxides and sulfides.
Claim 16
Dependent Claim 31 words
The process of claim 3 wherein said polar compound (A) is selected from the group consisting of esters of carboxylic acids, ketones, and halogenated hydrocarbons having a molecular weight above 1,000.
Claim 17
Dependent Claim 12 words
The process of claim 3 wherein said polar compound is a ketone.
Claim 18
Dependent Claim 10 words
The process of claim 8 wherein said ketone is acetone.
Claim 19
Dependent Claim 12 words
The process of claim 8 wherein said ketone is methyl ethyl ketone.
Claim 20
Dependent Claim 13 words
The process of claim 3 wherein said cure takes place at ambient conditions.
Claim 21
Dependent Claim 16 words
The process of claim 3 wherein said curing takes place at a temperature of about 25*-150*C.
Claim 22
Dependent Claim 14 words
A new composition of matter, a mixture of a amine-curable polymer or copolymer with
Claim 23
Dependent Claim 14 words
A new composition of matter, a mixture of a amine-curable polymer or copolymer with
Claim 24
Dependent Claim 19 words
The composition of claim 13 wherein said amine-curable prepolymer or polymer is a urethane prepolymer containing free isocyanate groups.
Claim 25
Dependent Claim 31 words
The composition of claim 14 wherein said polar compound (A) is selected from the group consisting of esters, ketones, ethers, halogenated hydrocarbons, tertiary amines, fully substituted amides, sulfones, sulfoxides and sulfides.
Claim 26
Dependent Claim 30 words
The composition of claim 15 wherein said polar compound is selected from the group consisting of esters of carboxylic acids, ketones and halogenated hydrocarbons having a molecular weight below 1,000.
Claim 27
Dependent Claim 12 words
The Composition of claim 16 wherein said polar compound is a ketone.
Claim 28
Dependent Claim 10 words
The composition of claim 17 wherein said ketone is acetone.
Claim 29
Dependent Claim 12 words
The composition of claim 17 wherein said ketone is methyl ethyl ketone.
Claim 30
Dependent Claim 15 words
The composition of claim 14 wherein said complex is derived from 4''4-methylene-dianiline and sodium chloride.

References Cited (Backward Citations)

US3527744A Cited
US3755261A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1978-06-09 1978-12-09 1979-06-10 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1982-06-09 1982-12-09 1983-06-10 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1986-06-09 1986-12-09 1987-06-10 $7700.00 Window Closed / Lapsed

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