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Alkylated 4-aminobenzyl-4-aminocyclohexane

A technology of alkyl group and curing agent, applied in the field of aliphatic secondary diamine curing agent

Inactive Publication Date: 2010-02-24
AIR PROD & CHEM INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Formula I

Method used

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  • Alkylated 4-aminobenzyl-4-aminocyclohexane
  • Alkylated 4-aminobenzyl-4-aminocyclohexane
  • Alkylated 4-aminobenzyl-4-aminocyclohexane

Examples

Experimental program
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Embodiment 1

[0042] Example 1: Preparation of 4-aminobenzyl-4-aminocyclohexane reduction alkylate

[0043] 179.6 grams (g) of 4-aminobenzyl-4-aminocyclohexane was placed in a 1 liter Parr reactor followed by 2.6 g of palladium on carbon (5% Pd / C) catalyst , 2.6 grams of platinum on carbon (5% Pt / C) catalyst and 525 grams of acetone (Aldrich #179124). The molar ratio of acetone to amine is 1.2 / 1. The reactor was sealed and then filled with N 2 Blow several times to remove trapped air. then use H 2 Purge and leak test at 120 psi gauge (psig). The agitation rate was set to 800-1000 revolutions per minute (rpm), and the temperature of the vessel was ramped to 60°C while maintaining 300 psig of hydrogen. These conditions were held constant until the rate at which hydrogen gas was absorbed into the reaction from the 1 liter hydrogen ballast tank dropped to less than 1 psig / minute. The temperature was then raised to 120°C and the hydrogen pressure was increased to 500-800 psig and held for ...

Embodiment 2

[0045] Example 2: Preparation of 4-aminobenzyl-4-aminocyclohexane reduction alkylate

[0046] 224.3 g of 4-aminobenzyl-4-aminocyclohexane was placed in a 1 liter Parr reactor followed by 1.0 g of Pd / C catalyst, 1.0 g of Pt / C catalyst, 1.0 g of Pt / S / C ( platinum sulfur on carbon catalyst), and 150.7 grams of acetone (Aldrich #179124). The molar ratio of acetone to amine is 2.5 / 1. The reactor was sealed and then filled with N 2 Blow several times to remove trapped air. then use H 2 Purge and leak check at 120 psig. The agitation rate was set to 800-1000 rpm and the temperature of the vessel was raised to 60°C while maintaining 300 psig of hydrogen. These conditions were held constant until the rate at which hydrogen was drawn into the reaction from the 1 liter hydrogen ballast tank dropped to less than 1 psig / min. The temperature was then raised to 120°C and the hydrogen pressure was increased to 500-800 psig and held for 0.5-1.5 hours until the reaction was complete. The...

Embodiment 3

[0048] Example 3: Preparation of polyurea coatings containing alkylated 4-aminobenzyl-4-aminocyclohexane (di-isopropyl reduced alkylate)

[0049] A polyurea elastomeric spray coating containing the reduced alkylate of Example 2 was prepared in the following manner. First, by mixing 42% diisopropyl 4-aminobenzyl-4-aminocyclohexane with 58% JEFFAMINE D-2000 (supplied by Huntsman Corporation) was mixed to prepare the amine resin component (B component). A commercially available 14.5% IPDI quasi-prepolymer (Cap 100 supplied by Specialty Products, Inc. TM ) as the isocyanate component (A component). Add both components A and B to the Quadro In a double-barrelpneumatic joint-filler gun of a Mixer static mixing head (8.7 / 24 x 161 millimeters (mm), supplied by Sulzer Chem Tech). The two components were shot through the gun in a 1:1 volume ratio onto a release liner at a pressure of 60 pounds per square inch (psi). The samples were allowed to cure at ambient conditions for 2 days...

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Abstract

This invention relates to alkylated 4-Aminobenzyl-4-Aminocyclohexane. This invention provides alkylated 4-aminobenzyl-4-aminocyclohexane curing agents that can be used, for example, in polyurea, polyurethane and urea / urethane hybrid elastomeric, epoxy resin, epoxy adhesive, epoxy composites and / or coating compositions and polymeric compositions comprising these curing agents are provided herein. In one embodiment, the curing agent comprises a compound having the following Formula I: wherein R1 and R2 are each independently a hydrogen, an alkyl group comprising from 1 to 20 carbon atoms, or combinations thereof. In another embodiment, a method of making the polymeric composition comprising the compound having the above Formula I is provided herein.

Description

technical field [0001] Disclosed herein are aliphatic secondary bismuths that can be used in, for example, polyureas, polyurethanes, urea / urethane hybrid elastomers, epoxy resins, epoxy adhesives, and composites thereof, and / or coating compositions. Amine curing agent. Also disclosed are alkylated 4-aminobenzyl-4-aminocyclohexane curing agents and polymeric compositions comprising the same. Background technique [0002] The term "polymer composition" as used herein describes a composition comprising 2 or more repeating units. Specific examples of polymer compositions include, but are not limited to, polyureas, polyurethanes, urea / urethane hybrid elastomers, epoxy resins, epoxy adhesives and composites thereof, or coating compositions. Some polymer compositions such as polyurea elastomers are fast curing coatings with gel times that can be as short as 2-3 seconds. Due to its fast cure rate, these polyurea coatings can be applied over a wide temperature range, are relativel...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G18/32C08G59/50C09J175/02C09J175/04C09J163/00C09D175/02C09D175/04C09D163/00
CPCC08G59/5033C07C211/49C09D175/02C08G18/10C07C2101/14C08L63/00C09D163/00C09J163/00C07C2601/14C08G18/324C08G18/5024C08K5/17C08L75/04C07C211/43C08G59/50
Inventor G·A·维达奇C·T·图劳M·D·康纳E·M·奥康奈尔
Owner AIR PROD & CHEM INC