4-Methoxyphenol → Isophorone diisocyanate

HRID 1500594Notes

Reaction equation

HRID 1500594 reaction equation
[C:1]([O:5][CH2:6][C:7]([CH2:20][OH:21])([CH2:10][O:11][CH2:12][C:13]([CH2:18][OH:19])([CH2:16][OH:17])[CH2:14][OH:15])[CH2:8][OH:9])(=[O:4])[CH:2]=[CH2:3].[O:22]=[C:23]=[N:24][CH:25]1[CH2:34][C:33]([CH3:36])([CH3:35])[CH2:32][C:27]([CH3:37])([CH2:28][N:29]=[C:30]=[O:31])[CH2:26]1.COC1C=CC(O)=CC=1.C([O-])(=O)CCCCCCCCCCC.C([O-])(=O)CCCCCCCCCCC.C([Sn+2]CCCC)CCC>>[C:1]([OH:5])(=[O:4])[CH:2]=[CH2:3].[NH2:24][C:1]([O:5][CH2:6][CH3:7])=[O:4].[O:22]=[C:23]=[N:24][CH:25]1[CH2:34][C:33]([CH3:36])([CH3:35])[CH2:32][C:27]([CH3:37])([CH2:28][N:29]=[C:30]=[O:31])[CH2:26]1.[C:1]([O:5][CH2:6][C:7]([CH2:20][OH:21])([CH2:10][O:11][CH2:12][C:13]([CH2:18][OH:19])([CH2:16][OH:17])[CH2:14][OH:15])[CH2:8][OH:9])(=[O:4])[CH:2]=[CH2:3]

Participants

7

Reactant 4

HCID 90154-MethoxyphenolHCID 169132Isophorone diisocyanateHCID 9809426Di-n-butyldilauryltinHCID 44145593HCID 44145593, compound

Product 3

HCID 169132Isophorone diisocyanateHCID 21863578Urethane acrylateHCID 44145593HCID 44145593, compound

Procedure

Into a 3-liter separable flask were put 2248 parts (2 mol) of dipentaerythritol acrylate (manufactured by Nippon Kayaku, trade name: KAYARAD DPHA), 222 parts (1 mol) of isophorone diisocyanate and 0.49 parts of hydroquinone monomethyl ether. With stirring, air was introduced into the liquid through a glass tube, and the liquid temperature was made to be 70° C. Thereto was added 0.49 parts of dibutyltin dilaurate and while the reaction temperature was adjusted to be between 70 and 80° C., reaction was performed for 6 hours to give a urethane acrylate of isophorone diisocyanate and dipentaerythritol acrylate.

Workup

  1. customInto a 3-liter separable flask were put
  2. additionair was introduced into the liquid through a glass tube
  3. customto be 70° C
  4. customto be between 70 and 80° C.
  5. customreaction

Sources & evidence

ORD record
ord-c3ebc7278006493fa5c0b32718284dcb
Source dataset
uspto-grants-2015_12
Patent number
US09206117B2

Reaction notes

Loading…