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Process for producing phenalkamines

A phenalkamine, product technology, applied in the field of curing epoxy resin, to achieve the effect of short coating drying time, low environmental driving force, and low tendency

Inactive Publication Date: 2021-01-15
EVONIK OPERATIONS GMBH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The present invention solves the problems associated with phenalkamine curing agents by providing low viscosity (<3000 mPa.s at 25°C) compositions which can be used neat or dissolved in a minimal amount (<20% by weight) of organic solvents or diluents to achieve curing of epoxy resins

Method used

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  • Process for producing phenalkamines
  • Process for producing phenalkamines
  • Process for producing phenalkamines

Examples

Experimental program
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Effect test

preparation example Construction

[0065] In the second step of the preparation of the phenalkamine curing agent, the Mannich base intermediate of step 1 is reacted with a compound having at least one alkylene or aralkylene group and at least two amino groups to undergo amine exchange. In one embodiment, the method is carried out at a temperature of 80°C to 150°C. In another embodiment, the method is performed at 120°C to 150°C. In a further embodiment, the method is performed at 120°C to 140°C. During this step, the secondary amine used in step 1 was liberated and recovered by condensing it into a vessel at subambient temperature (5°C).

[0066] Preferred examples of compounds having at least one alkylene or aralkylene group and at least two amino groups used in step 2 are ethylenediamine (EDA), diethylenetriamine (DETA), triethylenetetramine ( TETA), Tetraethylenepentamine (TEPA), Pentaethylenehexamine (PEHA), Hexaethyleneheptamine (HEHA), Propylenediamine, Dipropylenetriamine, Tripropylenetetramine, Tetra...

Embodiment 1

[0150] Embodiment 1: prepare cardanol / dimethylamine Mannich base intermediate in Parr pressure reactor

[0151]A 2-L Parr pressure reactor was charged with cardanol (298.46 grams, 1 mole) and 40% aqueous dimethylamine (112.7 grams, 2.5 moles, 281.75 grams 40% aqueous solution). Reactor contents with N 2 Purge 3x and thereafter vent to ambient pressure. The mixture was stirred to 300 rpm while 37% aqueous formaldehyde (75.07 grams, 2.5 moles, 202.7 grams of 37% aqueous solution) was added by pump over half an hour while maintaining the temperature at 25°C. After the formaldehyde addition, the temperature was increased to 140°C while monitoring the pressure rise. The temperature was maintained at 140°C for 1 hour at a pressure of -100 psi. The reactor was cooled to room temperature and the contents were poured into a 2 liter flask. Water was removed by distillation to recover the product as a reddish brown liquid.

Embodiment 2

[0152] Embodiment 2: prepare cardanol / dimethylamine Mannich base intermediate in glass reactor

[0153] Cardanol (298.46 g, 1 mole) and 40% dimethylamine in water (45 g, 1.0 mole, 112.5 g of 40% water in water) were charged to a N 2 Inlet tube, thermocouple, condenser, and addition funnel in a three-necked glass reactor. Reactor contents with N 2 purge. The mixture was stirred with an overhead mechanical stirrer and heated to 50°C. 37% aqueous formaldehyde (30 g, 1.0 mole, 81 g of 37% aqueous solution) was added over half an hour while maintaining the temperature at 50-70°C. After adding formaldehyde, the temperature was maintained at 80-90°C. The mixture was kept at this temperature for 1 hour. The reactor was cooled to room temperature and the contents were poured into a 2 liter flask. Water was removed by distillation to recover the product as a reddish brown liquid.

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Abstract

The present invention relates to a new method of making phenalkamines, products produced by such method, and use of such products. The method provides for phenalkamines obtained by an amine exchange reaction of a cardanol derived Mannich base with a compound with at least one alkylene or aralkylene group and at least two amino groups. These products may be used to cure, harden, and / or crosslink anepoxy resin. The curing agent compositions of this invention are of low viscosity and can be used neat or dissolved in a minimum amount of an organic solvent or diluent to effect cure of epoxy resins.

Description

Background technique [0001] The Mannich reaction is based on the reaction of aldehydes (usually formaldehyde), phenolic compounds and amines. Various forms of phenolic compounds, amines and aldehydes have been used in this reaction. Mannich base products are particularly suitable for curing epoxy resins. [0002] Phenalkamine curing agents are a class of Mannich bases obtained by reacting cardanol (extract of cashew nut shell liquid), an aldehyde compound (such as formaldehyde) and an amine. Usually, they are formed by reacting 1 molar equivalent of cardanol (according to the structure of formula (I) below) with 1 to 2 molar equivalents of aliphatic polyethylene polyamine and 1 to 2 molar equivalents of formaldehyde at 80-100°C production. Aromatic polyamines have also sometimes been used in this reaction. Commercially available phenalkamines based on ethylenediamine and diethylenetriamine as the amine source are available from various industry suppliers such as NC 541 and...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C213/02C07C215/50
CPCC07C213/02C07C215/50C07C211/13C07C211/49C08G59/50C08L63/00C08G59/504
Inventor G·S·拉尔M·库克E·罗佩拉克斯G·A·维达吉
Owner EVONIK OPERATIONS GMBH