Ethyl red → Benzopinacol

HRID 1863143

Reaction equation

CCN(C1C=CC(N=NC2C(C(O)=O)=CC=CC=2)=CC=1)CC.CCN1C2C(=CC=CC=2)C=C/C/1=C\C1C2C(=CC=CC=2)[N+](CC)=CC=1.[I-].CO[C:51]1[C:56](F)=[C:55](F)[C:54]([C:59]([C:67]([C:81]2[CH:86]=[CH:85][CH:84]=[CH:83][CH:82]=2)([C:69]2[C:74](F)=[C:73](F)[C:72](OC)=[C:71](F)[C:70]=2F)[OH:68])([C:61]2[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=2)[OH:60])=[C:53](F)[C:52]=1F>CC(C)=O.COCCO>[C:69]1([C:67]([C:59]([C:61]2[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=2)([C:54]2[CH:53]=[CH:52][CH:51]=[CH:56][CH:55]=2)[OH:60])([C:81]2[CH:86]=[CH:85][CH:84]=[CH:83][CH:82]=2)[OH:68])[CH:74]=[CH:73][CH:72]=[CH:71][CH:70]=1

Participants

Conditions

Temperature: 160 °C

Procedure

Ethyl red (2.0 mg), 1,1'-diethyl-2,4'-cyanine iodide, was dissolved in 2.0 ml. of acetone/2-methoxyethanol. Then, 50 mg of 4,4"-dimethoxy-2,3,5,6,2",3",5",6"-octafluorobenzopinacol was added. The solution was mixed with 1.0 ml of 20 percent polysulfonamide polymer solution (acetone/2-methoxyethanol (1:1)). The solution was mixed and coated on poly(ethylene terephthalate) film base at a wet thickness of 0.098 mm. It was allowed to dry at 49° C. for 15 minutes. The dye in the film had λ max at 565 nm, and at 530 nm, the optical density was 1.8 and 0.93, respectively. The film was heated at 160° C. for 10 seconds. The optical density of the heated film was 0.20 at λ=565 and 0.18 at 530 nm. The reduction in the dye density was 89 percent and 81 percent, at the two wavelengths. The same results were obtained after the film had been held in storage at room temperature for 6 months.

Workup

additionThe solution was mixed
customto dry at 49° C. for 15 minutes
customThe same results
customwere obtained after the film
waithad been held in storage at room temperature for 6 months

Sources & evidence

ORD record: ord-62f854ceafea47529baaa1c1e99ca39e
Source dataset: uspto-grants-1979_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04168218

Linked notes

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