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Formaldehyde → Triethanolamine

HRID 414116
Notes
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Reaction equation

HRID 414116 reaction equation
[CH2:1]([CH:3]1[O:5][CH2:4]1)Cl.C1(=O)[O:11][C:9](=O)[C:8]2=[CH:12][CH:13]=[CH:14][CH:15]=C12.C([CH:19]([OH:25])CCCCC)C.[OH-].[K+].[O:28]1CC[NH:30][CH2:29]1.[NH2:33]CC[CH:36]([CH2:38][NH2:39])[OH:37].C(C(CCCC)COC(=O)C=C)C.C=O.C(N(CCCN)CC)C.C(C(CCCC)CO)C>COCC(O)C.C(N(CC)CC)C>[CH:13]1[CH:12]=[CH:4][C:3]([CH:1]([N:33]=[C:19]=[O:25])[N:30]=[C:29]=[O:28])=[CH:15][CH:14]=1.[N:39]([CH2:8][CH2:9][OH:11])([CH2:4][CH2:3][OH:5])[CH2:38][CH2:36][OH:37]
ParticipantsConditionsProcedureSources & evidenceReaction notes

Participants

14

Reactant 10

HCID 712FormaldehydeHCID 6811Phthalic AnhydrideHCID 76362-Ethylhexyl acrylateHCID 77202-EthylhexanolHCID 7835EpichlorohydrinHCID 115273-OctanolHCID 14797Potassium Hydroxide
HCID 61011
N,N-Diethyl-1,3-propanediamine
HCID 1646562-Hydroxyputrescine
HCID 5366831,3-Oxazolidine2×

Product 2

HCID 7618TriethanolamineHCID 12905475Diisocyanatotoluene

Reagents, catalysts & solvents 2

HCID 8471TriethylamineCatalystHCID 79001-Methoxy-2-propanolSolvent2×

Conditions

Temperature
50 °C

Procedure

BM 2: 500 parts of an epoxy resin based on Bisphenol A and epichlorohydrin (epoxy equivalent weight about 500) are dissolved in 214 parts propyleneglycol monomethylether and reacted at 110° C. with 83 parts of a semiester of phthalic acid anhydride and 2 ethylhexanol, in the presence of 0.5 parts of triethylamine as catalyst, to an acid value of below 3 mg KOH/g. Then, 120 parts of an NH-functional oxazolidine of aminoethylethanolamine, 2-ethylhexylacrylate and formaldehyde, and 26 parts diethylaminopropylamine are added and the batch is reacted at 80° C. to an epoxy value of practically zero. The batch is diluted with 200 parts propyleneglycol monomethylether. 70 parts (resin solids) of this oxazolidine modified epoxy resin amine adduct are homogenized for 30 minutes at 50° C. with 30 parts based on resin solids of a crosslinking component obtained through reaction of 1 mole of a toluylene diisocyanate semi-blocked with 2-ethylhexanol and 0.33 moles triethanolamine. The reaction is carried out in a 70% solution of diethyleneglycol dimethylether, at 50 to 60° C. until all isocyanate groups have reacted.

Sources & evidence

ORD record
ord-4a7f5ce4883543a39e6e73e605fb7938
Source dataset
uspto-grants-1988_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04789696

Reaction notes

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On this pageParticipantsConditionsProcedureSources & evidenceReaction notes