Diallyl bisphenol A Chemical Properties

Boiling point:

445.2±40.0 °C(Predicted)

Density 

1.08 g/mL at 25 °C(lit.)

vapor pressure 

0Pa at 20℃

refractive index 

n20/D 1.587(lit.)

Flash point:

>230 °F

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

pka

10.53±0.10(Predicted)

form 

viscous liquid

Appearance

Off-white to yellow Solid-Liquid Mixture

Water Solubility 

31.1mg/L at 20℃

InChI

InChI=1S/C21H24O2/c1-5-7-15-13-17(9-11-19(15)22)21(3,4)18-10-12-20(23)16(14-18)8-6-2/h5-6,9-14,22-23H,1-2,7-8H2,3-4H3

InChIKey

WOCGGVRGNIEDSZ-UHFFFAOYSA-N

SMILES

C(C1=CC=C(O)C(CC=C)=C1)(C1=CC=C(O)C(CC=C)=C1)(C)C

LogP

4.12 at 20℃

CAS DataBase Reference

1745-89-7(CAS DataBase Reference)

EPA Substance Registry System

Phenol, 4,4'-(1-methylethylidene)bis[2-(2-propenyl)- (1745-89-7)

Safety Information

Hazard Codes 

C

Risk Statements 

34-43

Safety Statements 

23-26-27-36/37/39-45

RIDADR 

UN 1760 8/PG 3

WGK Germany 

3

HazardClass 

8

PackingGroup 

III

MSDS

• Language:English Provider:2,2'-Diallylbisphenol A
• Language:English Provider:SigmaAldrich

Diallyl bisphenol A Usage And Synthesis

Appearance

Diallyl bisphenol A is light yellow or brown liquid

application

It is mainly used for the modification of Bismaleimide (BMI), which can greatly reduce the application cost of BMI resin and improve the handling and processability of BMI resin. Improve the toughness, heat resistance and moldability of BMI resin. Can be used for:
1. electrical insulation materials, copper clad circuit boards, high temperature impregnating varnish, insulating varnish laminates, molded plastics, etc.
2. wear-resistant materials, diamond grinding wheel, heavy-duty grinding wheel, brake pads, high temperature bearing adhesives, etc.
3. aerospace structural materials.
4. functional materials. Anti-aging agent for rubber, adding 1-3% BBA to rubber can greatly improve the anti-aging process of rubber.

Storage Condition

Keep in a cool, dry, dark location in a tightly sealed container or cylinder. Keep away from incompatible materials, ignition sources and untrained individuals. Secure and label area. Protect containers/cylinders from physical damage.

Chemical Properties

2,2'-Diallylbisphenol A (DBA) is a light yellow or brown liquid at room temperature and pressure, has a phenolic odor, and is somewhat acidic.

Uses

diallyl bisphenol A is a kind of modified monomer of thermosetting resin which is mainly used in the modifying and toughening of bismaleimide resin, epoxy resin, phenolic resin etc., and it can enhance the toughness of thermosetting resin greatly. It also can be used as actively diluent of thermosetting resin. The adhesion strength between metal can be further improved when used in rubber.

General Description

2,2′-Diallylbisphenol A (DABA) is a diallyl based epoxy modification agent that blends with the resin to improve the mechanical property of the epoxy material. It is majorly used in novalac based resins, which can be further cured with bismaleimides (BMI) for aerospace, electronics and wireless communication based applications.

Synthesis

To an autoclave equipped with a stirrer was added 356 g of ethylene glycol monobutyl ether and 19 g of water, followed by 150 g (0.657 mol) of bisphenol A. Sequentially, 53 g (1.325 mol) of sodium hydroxide and 14 g (0.132 mol) of sodium carbonate were added. Next, 121 g (1.581 mol) of 3-chloropropene was added, the autoclave was sealed, and the reaction was heated at 100 to 105 °C for 8 hours. Upon completion of the reaction, unreacted 3-chloropropene was removed by distillation according to the same method as in Example 1 and aqueous phase separation was performed. After neutralizing the reaction mixture, heat treatment was performed to obtain a glycol monobutyl ether solution of bisphenol A diallyl ether. The solution had a sodium ion content of about 10 ppm. 2,2-bis(4-allylhydroxyphenyl)propane was analyzed by HPLC at a composition ratio of 95.0% (area percentage), bisphenol A at 0.2%, and 4-hydroxyphenyl-4'-allylhydroxyphenylpropane (bisphenol A monoallyl ether) at 2.2%. Based on the content of bisphenol A monoallyl ether, a yield of 95% was calculated. The thermally filtered reaction solution (filtrate) was transferred to an autoclave and heated and reacted under closed conditions (0.1 MPaG) at 195-200 °C for 7 hours. Subsequently, ethylene glycol monobutyl ether was removed by distillation under reduced pressure at 150 °C to give 166 g of 4,4'-(propane-2,2-diyl)bis(2-allylphenol) (yield: 82%). The HPLC composition ratio of the resulting product was 92.0% (% area).

References

[1] Patent: KR101597659, 2016, B1. Location in patent: Paragraph 0104-0107

Diallyl bisphenol A(1745-89-7)Related Product Information

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