Imidazole → Imidazole trimellitate

HRID 895759Notes

Reaction equation

HRID 895759 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.C(OCCC[Si](OC)(OC)OC)(=O)C(C)=C.[SiH4].C1(C2NC=CN=2)C=CC=CC=1.[C:34]([OH:48])(=[O:47])[C:35]1[C:36](=[CH:40][C:41](=[CH:45][CH:46]=1)[C:42]([OH:44])=[O:43])[C:37]([OH:39])=[O:38]>C(OCC)(=O)C>[C:34]([OH:48])(=[O:47])[C:35]1[C:36](=[CH:40][C:41](=[CH:45][CH:46]=1)[C:42]([OH:44])=[O:43])[C:37]([OH:39])=[O:38].[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

7

Reactant 5

HCID 795Imidazole2×HCID 10708Trimellitic acidHCID 173183-(Trimethoxysilyl)propyl methacrylateHCID 23953SilaneHCID 695912-Phenylimidazole

Product 1

HCID 22381556Imidazole trimellitate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

13.6 g (0.2 mol) of imidazole and 24.8 g (0.1 mol) of (3-methacryloxypropyl)trimethoxysilane were mixed and reacted at 100° C. for 11 hours. After cooling to room temperature, 100 ml of ethyl acetate was added, and excess imidazole was removed by washing the product three times in 100 ml of deionized water. Molecular sieves were added to the product, and the ethyl acetate solution was dried overnight. Subsequently, the ethyl acetate was distilled off in a rotary evaporator, and the imidazole group-containing silane coupling agent expressed by the formula (4) below was obtained. In the formula, R6, R7, and R8 are H; R9 is CH3; R10 is CH3; o is 3; and p is 3. 12.64 g (0.04 mol) of the imidazole group-containing silane coupling agent thus obtained, 8.64 g (0.06 mol) of 2-phenylimidazole (melting point: 137-147° C.), and 21.0 g (0.1 mol) of trimellitic acid were heated and mixed at 160° C., the reaction was continued for one hour, and the product was cooled to room temperature, yielding an imidazole trimellitate composition that was solid at normal temperature. The solid product thus obtained was ground with a mortar and classified by a sieve with hole openings of 90 microns to yield pulverized Sample No. 2. Evaluation of Adhesion Properties

Workup

  1. customreacted at 100° C. for 11 hours
  2. customexcess imidazole was removed
  3. washby washing the product three times in 100 ml of deionized water
  4. additionMolecular sieves were added to the product
  5. dry with materialthe ethyl acetate solution was dried overnight
  6. distillationSubsequently, the ethyl acetate was distilled off in a rotary evaporator
  7. additionthe imidazole group-containing silane coupling agent
  8. custombelow was obtained
  9. customthus obtained
  10. additionmixed at 160° C.
  11. temperaturethe product was cooled to room temperature

Sources & evidence

ORD record
ord-f49c0bf7e3e54140a1fa1894069f6279
Source dataset
uspto-grants-2005_07
Patent number
US06916865B2

Reaction notes

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