Azobisisobutyronitrile → Acrylurethane

HRID 381615Notes

Reaction equation

HRID 381615 reaction equation
[C:1]([O:5][CH2:6][CH:7](CC)CCCC)(=[O:4])C=C.C(#N)C=C.CC(C(OCCO)=O)=C.CC(N=NC(C#N)(C)C)(C#N)C.C1CCN(C[CH:46]2C(C3C=CC(Cl)=CC=3)=N[NH:50][C:48](=[O:49])[CH2:47]2)CC1.Cl.C(NN)(=O)CCCC(NN)=O>O.CC(O)C.CCC(C)=O>[C:48]([NH:50][C:1]([O:5][CH2:6][CH3:7])=[O:4])([CH:47]=[CH2:46])=[O:49]

Participants

10

Reactant 6

HCID 6547AzobisisobutyronitrileHCID 76362-Ethylhexyl acrylateHCID 7855AcrylonitrileHCID 133602-Hydroxyethyl Methacrylate2×HCID 30313456-(p-Chlorophenyl)-5-(piperidinomethyl)-4,5-dihydro-3(2H)-pyridazinone monohydrochlorideHCID 3958848Pentanedihydrazide

Product 1

HCID 11768685Acrylurethane

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3776IsopropanolSolvent2×HCID 6569Methyl Ethyl KetoneSolvent2×

Conditions

Temperature
75 °C

Procedure

In the dropping tank of a reaction vessel (tank) equipped with a stirrer, a thermometer, a nitrogen-sealing tube, a condenser and a dropping tank were placed 8.0 parts of MMA, 15.0 parts of BA, 1.0 part of AA, 1.0 part of 2-ethylhexyl acrylate (referred to here-inafter as EHA), 10.0 parts of acrylonitrile (referred to hereinafter as AN), 5.0 parts of HEMA, 5.0 parts of DAAA, 1.0 part of AIBN, 25 parts of MEK and 25 parts of IPA and then uniformly mixed. Separately, in the reaction tank were placed 20.0 parts of PA-8, 8.0 parts of MMA, 15.0 parts of BA, 1.0 part of AA, 1.0 part of EHA, 10.0 parts of AN, 5.0 parts of HEMA, 5.0 parts of DAAA, 20 parts of MEK and 20 parts of IPA and then uniformly mixed. Subsequently, the reaction tank was heated to 75° C. and the liquid mixture in the dropping tank was dropped into the reaction tank over 5 hours. Thereafter, the resulting mixture was further subjected to reaction at the same temperature for 4 hours. Thereafter, 2.8 parts of TEA was added to the reaction mixture to sufficiently neutralize the same and then aqueous hydrazide consisting of 148 parts of distilled water and 4.7 parts of glutaric acid dihydrazide (referred to hereinafter as GDH) was added thereto to emulsify the reaction mixture. Thereafter, the MEK and the IPA present in the system were removed at 60° C. at 100 Torr to obtain an aqueous emulsion of a self-emulsifiable acryl-urethane copolymer having a solid content of 39.9% (the emulsion is referred to hereinafter as EA-11).

Workup

  1. customIn the dropping tank of a reaction vessel (tank) equipped with a stirrer
  2. additionuniformly mixed
  3. additionuniformly mixed
  4. additionthe liquid mixture in the dropping tank was dropped into the reaction tank over 5 hours
  5. customThereafter, the resulting mixture was further subjected to reaction at the same temperature for 4 hours
  6. additionThereafter, 2.8 parts of TEA was added to the reaction mixture
  7. additionwas added
  8. customThereafter, the MEK and the IPA present in the system were removed at 60° C. at 100 Torr

Sources & evidence

ORD record
ord-f52317c0476c4330a5e4a6f1b79aa82f
Source dataset
uspto-grants-2001_10
Patent number
US06306947B1

Reaction notes

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