Acrylic Acid → N,N'-Dicyclohexylurea

HRID 634864Notes

Reaction equation

HRID 634864 reaction equation
[CH:1]1([N:7]=[C:8]=[N:9][CH:10]2[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(O)(=[O:19])C=C.C1(CO)C2C(=CC3C(C=2)=CC=CC=3)C=CC=1>CN(C1C=CC=CN=1)C.CN(C1C=CN=CC=1)C.O1CCCC1>[C:8]([NH:7][CH:1]1[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1)([NH:9][CH:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1)=[O:19]

Participants

7

Reactant 3

HCID 6581Acrylic AcidHCID 10868Dicyclohexylcarbodiimide2×HCID 12695455(Anthracen-1-yl)methanol

Product 1

HCID 4277N,N'-Dicyclohexylurea

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 218852-DimethylaminopyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

The adhesive was converted to a switchable adhesive. The method used for esterification of the carboxylic acid groups pendant to the prepolymer chain employed a dehydrating agent, dicyclohexylcarbodiimide (DCC). This was used in conjunction with a dimethylaminopyridine catalyst with the reaction proceeding at room temperature. The following general procedure was initially used for the esterification reaction. For Example 9a), 6.09 g of base PSA (containing 0.0068 moles acrylic acid) was placed in a dry jar along with 1.41 g of anthracenemethanol (0.0068 moles), 1.39 g DCC (0.0068 moles) and 0.33 g DMAP (0.00027 moles). Approximately 100 ml of anhydrous tetrahydrofuran (THF) was added to the reaction mixture which was left stirring overnight (˜24 hours). A precipitate was formed as a by-product of the esterification (dicyclohexylurea, DHU) which was insoluble in THF and was therefore filtered from the PSA solution. A viscous yellow liquid was produced which was then spread thinly onto Melinex for UV irradiation.

Workup

  1. customproceeding at room temperature
  2. customThe following general procedure was initially used for the esterification reaction
  3. waitwas left

Sources & evidence

ORD record
ord-f460179d8aa44be7a93a6d868ed0f549
Source dataset
uspto-grants-2001_02
Patent number
US06184264B2

Reaction notes

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