DIALLYL PHTHALATE (DAP)

CAS Number : 131-17-9
EC  Number : 205-016-3
Molecular Formula   :  C14H14O4 or C6H4(CO2CH2CHCH2)2
Molecular Weight    :  246.26
Melting Point        :  -94 °F
Boiling Point        : 554 °F at 760 mmHg

Diallyl Phthalate(DAP) resin is a thermosetting resin with a lot of excellent physical properties such as electrical insulation properties, heat resistance, water resistance, chemical resistance, and molding.

PROPERTIES AND APPLICATIONS of Diallyl phthalate (DAP)
Diallyl phthalate (DAP) is thermosetting ester resins produced by the reaction of allyl alcohol with ortho-phthalic anhydride and meta-phthalic anhydride, respectively. 
The cured resins have excellent electrical insulating properties including high insulation resistance and low electrical losses, even when subjected to to high heat and humidity over long periods of time. 
They also have excellent dimensional stability and do not warp in high-heat applications. 
Furthermore, they have low moisture absorption, excellent weathering properties, and good chemical resistance to many chemicals and solvents including aliphatic hydrocarbons, oils, alcohols, acids, and alkalis.

The monomers are often used as cross-linking agents in unsaturated (alkyd) polyester resins. 
As polymers, DAP and DAIP prepolymers are mainly used as molding resins for electrical and electronic parts such as switches, connectors, control panels, circuit breakers, terminal boards, resistors, and insulators. 
Other (potential) applications include laminates, prepregs, headlight lamp reflectors, bathtubs, sinks, appliance handles and control knobs. 

Use and Manufacturing of Diallyl phthalate (DAP)
Used to make insulators, potentiometers, and circuit boards in communication, computer, and aerospace systems; Also used as a monomer in thermosetting plastics, a diluent in polyester spray systems, a dye carrier; a sealant in insulating varnishes and metal castings, and an impregnant for jewelry.

Most diallyl phthalate compounds are sold under military specification and are used in critical electrical/electronic applications requiring high reliability under long-term, adverse environmental conditions. 
A significant application area is in electronic connectors in communications, computer and aerospace systems. 
Other uses are insulators, potentiometers, and circuit boards.

Diallyl phthalate (DAP) is used in industry as a monomer in the processing of thermosetting plastics, polyester resins, and varnishes.

Industry Uses of Diallyl phthalate (DAP)
-Adhesives and sealant chemicals
-Intermediates
-Paint additives and coating additives not described by other categories
-Plasticizers
-Solvents (which become part of product formulation or mixture)

Consumer Uses of Diallyl phthalate (DAP)
-Plastic and rubber products not covered elsewhere

General Manufacturing Information    
Industry Processing Sectors
-Adhesive manufacturing
-Electrical equipment, appliance, and component manufacturing
-Paint and coating manufacturing
-Plastic material and resin manufacturing
-Rubber product manufacturing

The term Diallyl phthalate (DAP) is used both for the monomeric and polymeric forms. 
The monomer is used as a cross-linking agent in unsaturated polyester resins. 
As a polymer, Diallyl phthalate (DAP) is used in the production of thermosetting molding powders, casting resins and laminates. 
This is the material of choice for critical, high-performance military and commercial electrical components where long-term reliability is demanded due to its ability to retain its superior insulating properties, even when subjected to extreme environmental conditions of high heat and high humidity over long time periods. 
Additionally, Diallyl phthalate (DAP) compounds will resist dimensional change in high-heat soldering environments where competitive materials may warp.

Properties of Diallyl phthalate (DAP)
In preparing the resin, Diallyl phthalate (DAP) is polymerized to a point where almost all the change in specific gravity has taken place. ,
Final cure, therefore, produces very little additional shrinkage. 
In fact, Diallyl phthalate (DAP) is cured by polymerization without water formation. 
The molded material, depending on the filler, has a tensile strength from 30 to 48 MPa, a compressive strength up to 210 MPa, a Rockwell hardness to M108, dielectric strength to 16.9 x 106 V/m, and heat resistance to 232°C.

Allylic resins enjoy certain specific advantages over other plastics, which make them of interest in various special applications. 
Allylics exhibit superior electrical properties under severe temperature and humidity conditions. 
These good electrical properties (insulation resistance, low loss factor, arc resistance, etc.) are retained despite repeated exposure to high heat and humidity. 
Diallyl phthalate (DAP) resin is resistant to 155 to 180°C temperatures, and the DAIP resin is good for continuous exposures up to 206 to 232°C temperatures. 
Allylic resins exhibit excellent post-mold dimensional stability, low moisture absorption, good resistance to solvents, acids, alkalis, weathering, and wet and dry abrasion. 
They are chemically stable, have good surface finish, mold well around metal inserts and can be formulated in pastel colors with excellent color retention at high temperatures.

A major application area for allyl compounds is electrical connectors, used in communications, computer, and aerospace systems. 
The high thermal resistance of these materials permits their use in vapor-phase soldering operations. 
Uses for prepolymers include arc-track-resistant compounds for switchgear and television components. 
Other representative uses are for insulators, encapsulating shells, potentiometer components, circuit boards, junction boxes, and housings.

Diallyl phthalate (DAP) is one of the most versatile of the thermosetting resins, in practice usually it has been filled by mineral, glass, and synthetic fiber. 
However, no effects so far have been made toward the development of reinforced DAP by nano-size fillers.
Diallyl phthalate (DAP) is a thermoset plastic. 
Diallyl phthalate (DAP) has the lowest tensile strength among thermoset plastics. 
In addition, it has the lowest mechanical heat stability and a fairly high dielectric strength. 
The graph bars on the material properties cards below compare DAP to other thermoset plastics (top) and the entire database (bottom). 
A full bar means this is the highest value in the relevant set. 
A half-full bar means it's 50% of the highest, and so on.

Diallyl phthalate (DAP) can be described as polymerizable plasticizer in that it functions as a typical phthalate plasticizer in the uncured states of the compound (such as during mixing and extruding). 
Yet contains two allyl groups per molecule that allow cross-linking to increase the cured cross-link density and to lock the plasticizer in place. 
Though is not viscous, it is relatively expensive when compared to the standard phthalate and adipate monomeric plasticizers; and the called-for amount needs to go into the batch instead of being left in a weigh-up container or in a mill pan when the band breaks. 
Diallyl phthalate (DAP) solves the handling, weighing, and mixing problems.

Features & Benefits of Diallyl phthalate (DAP):
-Eliminates drum disposal
-Eliminates need for heating viscous liquid
-80% reduction in VOCs compared with Texanol: meets and exceeds international regulations for no VOCs
-Improves Handling
-Improves Safety
-Reduces employee exposure
-Reduces waste
-Reduces clean up time

Main Usage of Diallyl phthalate (DAP): 
1. Synthesis of acrylic resin, such as waterproof glue. 
2. Unsaturated polyester resin, used in the production of insulating varnish. 
3. Internal plasticizer for polymer, used in the plasticizer of PVC. 
4. Self polymerization polymer, used in molding materials. 

Physical Properties of Diallyl phthalate (DAP):
Molecular weight : 246
Refractive index (25 ºC) : 1.516 – 1.520
Viscosity (20 ºC) : 12 cps
Boiling Point : 157 – 165 ºC/5 torr
Coagulation Point : -70 ºC
Flash Point (open up) : 166 ºC
Stability of the Product : 12 months 

Diallyl Phthalate (DAP) is a thermoset of the allyl family used as a cross-linking monomer for unsaturated polyesters, and as a primary plasticizer for many resins. 
Diallyl Phthalate (DAP)  polymerizes easily, increasing in viscosity until it finally becomes a clear, infusible solid. 
The designation Diallyl Phthalate (DAP)  is used for both the monomeric and polymeric forms. 
In the partially polymerized form, Diallyl Phthalate (DAP)  is used in the production of thermosetting molding powders, casting resins and laminates.
Diallyl Phthalate (DAP)  is widely used for critical, high-performance military and commercial electrical components where long-term reliability is demanded and cost is not an overriding factor. 
Diallyl Phthalate (DAP)  compounds resist dimensional change in high-heat soldering environments where competitive materials can warp. 
Diallyl Phthalate (DAP)  products are also highly resistant to solvents, acids, alkalies, fuels, hydraulic fluids, plating chemicals and sterilizing solutions and are inert to fungus growth.

First Aid Measures of Diallyl phthalate (DAP)

EYES: 
First check the victim for contact lenses and remove if present. 
Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. 
Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. 
IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop. 

SKIN: 
IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. 
Gently wash all affected skin areas thoroughly with soap and water. 
If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment.

INHALATION: 
IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. 
If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere. 
Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing.

INGESTION: 
DO NOT INDUCE VOMITING. 
If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. 
Be prepared to transport the victim to a hospital if advised by a physician. 
If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. 
DO NOT INDUCE VOMITING. 
IMMEDIATELY transport the victim to a hospital.

Substance identity

EC / List no.: 205-016-3
CAS no.: 131-17-9
Mol. formula: C14H14O4

Hazard classification & labelling of Diallyl phthalate (DAP)
Warning! According to the harmonised classification and labelling (CLP00) approved by the European Union, this substance is very toxic to aquatic life, is very toxic to aquatic life with long lasting effects and is harmful if swallowed.
Additionally, the classification provided by companies to ECHA in REACH registrations identifies that this substance is harmful if inhaled and may cause an allergic skin reaction.

About Diallyl phthalate (DAP)
Diallyl phthalate (DAP) is registered under the REACH Regulation and is manufactured in and / or imported to the European Economic Area, at ≥ 100 to < 1 000 tonnes per annum.
Diallyl phthalate (DAP) is used in articles, in formulation or re-packing and at industrial sites.

Consumer Uses of Diallyl phthalate (DAP)
ECHA has no public registered data indicating whether or in which chemical products the substance might be used. 
ECHA has no public registered data on the routes by which this substance is most likely to be released to the environment.

Article service life of Diallyl phthalate (DAP)
Other release to the environment of Diallyl phthalate (DAP) is likely to occur from: indoor use in long-life materials with low release rate (e.g. flooring, furniture, toys, construction materials, curtains, foot-wear, leather products, paper and cardboard products, electronic equipment).
Diallyl phthalate (DAP) can be found in products with material based on: plastic (e.g. food packaging and storage, toys, mobile phones).

Widespread uses by professional workers of Diallyl phthalate (DAP)
ECHA has no public registered data indicating whether or in which chemical products the substance might be used. 
ECHA has no public registered data on the types of manufacture using this substance. 
ECHA has no public registered data on the routes by which this substance is most likely to be released to the environment.

Formulation or re-packing of Diallyl phthalate (DAP)
Diallyl phthalate (DAP) is used in the following products: coating products.
Release to the environment of Diallyl phthalate (DAP) can occur from industrial use: formulation of mixtures.

Uses at industrial sites of Diallyl phthalate (DAP)
Diallyl phthalate (DAP) is used in the following products: adhesives and sealants, coating products and polymers. 
Diallyl phthalate (DAP) is used for the manufacture of: electrical, electronic and optical equipment, rubber products and plastic products. 
Release to the environment of Diallyl phthalate (DAP) can occur from industrial use: in processing aids at industrial sites, in the production of articles and as processing aid.

Manufacture of Diallyl phthalate (DAP)
ECHA has no public registered data on the routes by which this substance is most likely to be released to the environment.

Synonyms:
DIALLYL PHTHALATE
131-17-9
Allyl phthalate
Diallylphthalate
Dapon R
Phthalic Acid Diallyl Ester
Dapon 35
1,2-Benzenedicarboxylic acid, di-2-propenyl ester
Phthalic acid, diallyl ester
o-Phthalic acid, diallyl ester
NCI-C50657
1,2-Benzenedicarboxylic acid, 1,2-di-2-propen-1-yl ester
NSC 7667
bis(prop-2-enyl) benzene-1,2-dicarboxylate
Diallylester kyseliny ftalove
F79L0UL6ST
phthalic acid, bis-allyl ester
143318-73-4
DIPROP-2-ENYL BENZENE-1,2-DICARBOXYLATE
25053-15-0
DSSTox_CID_392
DSSTox_RID_75560
DSSTox_GSID_20392
CAS-131-17-9
CCRIS 1361
HSDB 4169
poly(diallyl phthalate)
Diallylester phthalic acid
EINECS 205-016-3
Diallylester kyseliny ftalove [Czech]
UNII-F79L0UL6ST
BRN 1880877
Di-2-propenyl 1,2-benzenedicarboxylate
AI3-02574
DAP monomer
MFCD00008646
Phthalic acid diallyl
Diallyl phthalate, 97%
1,2-Benzenedicarboxylicaciddi-2-propenylester
EC 205-016-3
Allyl phthalate, homopolymer
Diallyl phthalate homopolymer
SCHEMBL15174
4-09-00-03188 (Beilstein Handbook Reference)
Diallyl ester o-phthalic acid
MLS002415725
Diallyl ester of phthalic acid
WLN: 1U2OVR BVO2U1
Diallyl Phthalate Monomer, DAP
RX 1-501N (Salt/Mix)
CHEMBL1329372
DTXSID7020392
NSC7667
HMS2267F17
RX 3-1-530 (Salt/Mix)
NSC-7667
ZINC1688261
Tox21_201961
Tox21_300135
Nonflammable decobest DA (Salt/Mix)
Diallyl phthalate, analytical standard
AKOS015891274
NCGC00091365-01
NCGC00091365-02
NCGC00091365-03
NCGC00091365-04
NCGC00254197-01
NCGC00259510-01
BS-14891
SMR001253767
FT-0624597
P0290
J-005948
Q2161731
1,2-bis(prop-2-en-1-yl) benzene-1,2-dicarboxylate
1,2-Benzenedicarboxylic acid, di-2-propenyl ester, homopolymer
Phthalic acid, bis-allyl ester 100 microg/mL in Acetonitrile
1,2-Benzenedicarboxylic acid, 1,2-di-2-propen-1-yl ester, homopolymer
1,2-Benzenedicarboxylic acid, di-2-propen-1-yl ester [ACD/Index Name]
1,2-Bis(prop-2-en-1-yl) benzene-1,2-dicarboxylate
131-17-9 [RN]
205-016-3 [EINECS]
25053-15-0 [RN]
CZ4200000
Diallyl phthalate [ACD/IUPAC Name]
Diallyl phthalate resin
Diallyl-phthalat [German] [ACD/IUPAC Name]
diprop-2-en-1-yl benzene-1,2-dicarboxylate
MFCD00008646 [MDL number]
Phtalate de diallyle [French] [ACD/IUPAC Name]
Phthalic acid, diallyl ester (8CI)
[131-17-9] [RN]
1,2-Benzenedicarboxylic acid 1,2-di-2-propen-1-yl ester
1,2-Benzenedicarboxylic acid, 1,2-di-2-propen-1-yl ester
1,2-Benzenedicarboxylic acid, di-2-propenyl ester
1,2-Benzenedicarboxylicaciddi-2-propenylester
124743-27-7 [RN]
143318-73-4 [RN]
3,5-diiodo-2-methyl benzoic acid
3,5-Diiodo-2-methylbenzoic acid [ACD/IUPAC Name]
4-09-00-03188 [Beilstein]
4-09-00-03188 (Beilstein Handbook Reference) [Beilstein]
ALLYL PHTHALATE
benzene-1,2-dicarboxylic acid diallyl ester
bis(prop-2-enyl) benzene-1,2-dicarboxylate
C049098
Dap
DAP monomer
Dapon R
dapon r.
Di-2-propenyl 1,2-benzenedicarboxylate
diallyl benzene-1,2-dicarboxylate
Diallyl ester of phthalic acid
Diallyl ester o-phthalic acid
Diallyl Phthalate Monomer, DAP
Diallyl phthalic acid
Diallylester kyseliny ftalove [Czech]
Diallylester kyseliny ftalove
Diallylester kyseliny ftalove [Czech]
diallylester phthalic acid
DIALLYLPHTHALATE
diprop-2-enyl benzene-1,2-dicarboxylate
EINECS 205-016-3
NCGC00091365-02
Nonflammable decobest da
Nonflammable decobest DA (Salt/Mix)
o-phthalic acid diallyl ester
o-Phthalic acid, diallyl ester
phthalic acid diallyl ester
Phthalic acid, bis-allyl ester
Phthalic acid, diallyl ester
POLY(DIALLYL PHTHALATE)
prop-2-enyl 2-(prop-2-enyloxycarbonyl)benzoate
RX 1-501N (Salt/Mix)
RX 3-1-530 (Salt/Mix)
ST5405391
WLN: 1U2OVR BVO2U1
F79L0UL6ST [DBID]
269379_ALDRICH [DBID]
36925_RIEDEL [DBID]
80090_FLUKA [DBID]
AI3-02574 [DBID]
BRN 1880877 [DBID]
CCRIS 1361 [DBID]
dapon 35 [DBID]
HSDB 4169 [DBID]
NCGC00091365-01 [DBID]
1,2-Benzenedicarboxylic acid, 1,2-di-2-propen-1-yl ester
1,2-Benzenedicarboxylic acid, di-2-propenyl ester
Allyl phthalate
Dapon 35
Dapon R
Di-2-propenyl 1,2-benzenedicarboxylate
Diallyl phthalate
Diallyl phthalate
Diallylester kyseliny ftalove
o-Phthalic acid, diallyl ester
Phthalic acid, diallyl ester
phthalic acid, diallyl ester
Phthalic acid, diallyl ester (8CI)
dialil ftalat (ro)
dialil ftalat (sl)
dialil-ftalat (hr)
dialilftalatas (lt)
diallil-ftalát (hu)
diallyl-ftalát (cs)
diallylftalaat (nl)
diallylftalat (no)
diallylftalat (sv)
diallylphthalat (da)
Diallylphthalat (de)
diallyyliftalaatti (fi)
Diallüülftalaat (et)
dialyl-ftalát (sk)
ester diallilowy kwasu ftalowego (pl)
ftalan diallilu (pl)
ftalato de dialilo (es)
ftalato de dialilo (pt)
ftalato di diallile (it)
phtalate de diallyle (fr)
dialilftalāts (lv)
φθαλικό διαλλύλιο (el)
диалил фталат (bg)