Phthalamide → Hexanediamide

HRID 1742120Notes

Reaction equation

HRID 1742120 reaction equation
C(N)(=O)[C:2]1[C:3](=[CH:7][CH:8]=[CH:9][CH:10]=1)[C:4]([NH2:6])=[O:5].[C:13]([NH2:26])(=[O:25])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22]([NH2:24])=[O:23].[C:27]([NH2:36])(=[O:35])[CH2:28][CH2:29][CH2:30][CH2:31][C:32]([NH2:34])=[O:33]>>[C:4]([NH2:6])(=[O:5])[C:3]1[CH:2]=[CH:10][C:9]([C:22]([NH2:24])=[O:23])=[CH:8][CH:7]=1.[C:13]([NH2:26])(=[O:25])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22]([NH2:24])=[O:23].[C:27]([NH2:36])(=[O:35])[CH2:28][CH2:29][CH2:30][CH2:31][C:32]([NH2:34])=[O:33]

Participants

6

Reactant 3

HCID 6956PhthalamideHCID 12364HexanediamideHCID 72882Sebacamide

Product 3

HCID 12364HexanediamideHCID 72882SebacamideHCID 76381Terephthalamide

Procedure

A series of films were prepared using these above four bisamides at an equivalent molar replacement, that is, normalizing to the molecular weights of 396.5, 432.6 and 376.5 for the phthalamide, sebacamide and adipamide replacements of 390.5 m.w. hexamethoxymethyl-melamine. Removal of 1.5 g melamine from a nominal ten g solids formulation therefore resulted in replacement by 1.52 g iso- or terephthalamide, 1.66 g sebacamide and 1.43 g adipamide. Removal of drawn films after curing for 20 minutes at 300° F. as described above allowed the following dynamic mechanical analysis of crosslinking as described in Journal of Coatings Technology, 46, no. 808, 29-42 (1992) by L. W. Hill in the article `Structure/Property Relationships of Thermoset Coatings.

Workup

  1. customA series of films were prepared
  2. customRemoval of 1.5 g melamine from a nominal ten g solids formulation

Sources & evidence

ORD record
ord-572584aa510f448483dcd996fccdfad7
Source dataset
uspto-grants-1994_08
Patent number
US05336807

Reaction notes

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