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53306-54-0
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53306-54-0
Bis(2-propylheptyl) phthalate, or di(2-propylheptyl) phthalate (abbreviated DPHP, or di(2-propylheptyl) phthalate) is a high molecular weight phthalate plasticizer formed from the esterification of phthalic anhydride with two molecules of 2-propylheptyl alcohol (isomeric C10 alcohol). It has the molecular formula C28H46O4, a molecular weight of 446.67, a CAS number of 53306-54-0, an EC number of 258-469-4 and a DTXSID of 5052173. It is an important high performance plasticizer in the flexible polyvinyl chloride (PVC) industry: DPHP is larger molecular weight, lower volatility, and better migration and heat resistance than commonly used DINP/DIDP. It is widely used in applications such as wire and cable, automotive interior, building waterproofing membranes, resilient flooring, artificial leather and sealants where heat resistance, low volatility and low migration are required. It is called a "high-end heat resistant general purpose plasticizer".
Basic Information Molecular Formula C28H46O4 Molecular Weight 446.67 CAS Number 53306-54-0 EC Number 258-469-4 DTXSID 5052173 NSC Number NSC 17071 MeSH Index Name di(2-propylheptyl)phthalate
In terms of structure and manufacturing, DPHP has a phthalate backbone (two ester groups on the benzene ring) and two 2-propylheptyl branches. The structure is "rigid aromatic ring core + two flexible isomeric C10 branches". Industrial preparation of 2-propylheptyl alcohol by carbonyl synthesis ( hydroformylation ) of octene ( 2-propylheptene ) , by esterification of the resulting 2-propylheptanal with phthalic anhydride under acid catalysis , purification and dehydration . 2-propylheptyl alcohol is an isomeric alcohol, which imparts to DPHP the low-temperature performance of branched plasticizers and the low volatility of higher alcohol plasticizers.
In terms of physical characteristics, DPHP is a colorless to pale yellow transparent oily liquid that is nearly odorless. It is denser than water, with a density of about 0.963 g/cm³ (20℃). Under reduced pressure, its boiling point is around 250-267℃ (5-6.5 hPa), and the estimated boiling point at normal pressure is above 430℃. The flash point is approximately 224℃ (closed cup). It has a viscosity of between 110-125 mPa·s (20℃), placing it in the medium-viscosity category. Its vapor pressure is very low (<0.01 Pa @ 20℃). The refractive index is roughly 1.482 (20℃). DPHP is insoluble in water (<0.001 g/L) but soluble in organic solvents such as aromatics, ketones, esters and chlorinated hydrocarbons. Its Log Kow is around 10, indicating that it is highly hydrophobic. When heated to decomposition, it releases irritating fumes.
Chemically, DPHP is a chemically stable ester compound. The ester bond can be hydrolyzed in strong acids and bases and at high temperatures to produce phthalic acid and alcohol, and it is stable to water, dilute acids, dilute bases, common oxidizing agents and reducing agents. It has the good compatibility with PVC resin, stabilizers, other plasticizers and most additives. It undergoes slow thermal oxidative degradation when heated for a long time above 200 ℃, and need to be used in conjunction with heat stabilizers.
In terms of the mechanism of action, DPHP plays an irreplaceable role due to the combination of "high molecular weight + low volatility + migration resistance + electrical insulation + low temperature performance":
Plasticization mechanism (reduction of the glass transition temperature)
DPHP molecules interpose between the macromolecular chains of PVC, weakening inter-chain dipole interactions and van der Waals forces, increasing the freedom of movement of chain segments, and significantly lowering the glass transition temperature (Tg) of PVC. Rigid PVC is made soft, flexible and resistant to bending from a rigid and brittle material. Its plasticizing efficiency is similar to that of DINP and it acts as a “functional enhancer” for soft PVC products.
Mechanism of Heat Resistance and Low Volatility
The molecular weight of DPHP is as high as 446.67 and the vapor pressure is less than 0.01 Pa. 2. DPHP almost has no volatilization loss during high-temperature processing of PVC (extrusion, calendering, coating) and long-term high-temperature use (current-carrying heating of cables, exposure to sunlight in car cabins). Key reason for superiority over DINP/DIDP is the resistance to heat aging and discoloration and absence of fogging film formation on car windows (anti-fogging).
Mechanisms of Migration and Resistance to Extraction
The high molecular weight of DPHP leads to a low diffusion coefficient in the PVC matrix. Compared with low molecular weight plasticizers, the rate of migration to the product surface and extraction rate to water/oil/solvent media are much smaller. The products do not become hardened after prolonged use, do not separate oil or become sticky on the surface and do not contaminate contact objects. It is suitable for cables, building materials and artificial leather requiring high durability.
Mechanism of electrical insulation and low temperature performance
The excellent electrical insulation properties of PVC cable materials are attributed to the high volume resistivity and low dielectric loss of DPHP; the 2-propylheptyl branched structure enables the molecular chains to move at low temperatures, which makes the products flexible at low temperature, prevents them from becoming brittle at low temperature, and meets the electrical and cold resistance requirements.
To summarize, DPHP is a high-performance heat resistant plasticizer used in applications as diverse as high voltage cables, automotive cabins, roofing waterproofing membranes and shopping mall resilient flooring. It has the main advantages of low volatility, migration resistance and electrical insulation, which makes it an important player in the high-end flexible PVC industry. However, it falls under the SVHC (reproductive toxicity 1B) regulation and is primarily used in the industrial and building materials sectors. It is not approved for use in toys, food contact or medical contact applications.
DPHP is used in wire and cable, automotive industry, building materials, consumer goods manufacturing, industrial products, textile coatings, sealants and adhesives and home maintenance. The subsequent sections describe each downstream end product / application area in more detail. They explain the application area, the products that fit, and why it works for that purpose:
Application areas： wire & cable, electrical products.
Matching products: PVC wire and cable insulation, PVC automotive wiring harness sheathing, heat resistant cable, control cable, mining cable, photovoltaic cable, plug and power cord, electrical insulation tape etc.
Why it works for this purpose: DPHP is a high molecular weight material with extremely low vapor pressure, which lends PVC cable materials excellent heat aging resistance, volume resistivity and dielectric strength (electrical insulation). It is also nearly non-volatile and non-migrating, which ensures that the insulation performance of the cable is stable and does not deteriorate during current-carrying heating and long-term operation. It has good compatibility with PVC and high plasticizing efficiency, which makes it a high-performance plasticizer in the heat-resistant cable materials field.
Application areas： Automobile interior components & parts.
Matching products: pvc dashboard covers, pvc door panels, leatherette seats, headliner film, sun visors, armrests, car floor mats, sealing strips, trunk liners etc.
Why it works for this purpose: Plasticizers must be low in volatility (to avoid fogging of car windows), migration-resistant (to avoid interior staining and stickiness) and aging-resistant in the high temperature and sunlight conditions of an automotive cabin. DPHP is much less volatile than standard plasticizers such as DINP/DIDP and possesses low temperature flexibility, which makes it a high performance choice for automotive interior PVC.
Application areas: automotive painting and body protection
Matching products: underbody coating, welding sealant, PVC plastisol coating for car body, wheel arch liner coating, etc.
Why it works for this purpose: DPHP has moderate viscosity and rheological properties and high plasticizing efficiency in PVC plastisol, which makes the primer and sealant have good workability and film-forming properties. Flexible, impact resistant, stone resistant, water resistant and salt spray resistant after curing. Protects vehicle body floor and welds against stone and water and salt corrosion for long time.
Application areas: Waterproofing of construction works Civil Engineering.
Matching products: PVC waterproof membrane, roof waterproof membrane, basement waterproof membrane, tunnel waterproof membrane, artificial lake/pool lining, bridge deck waterproof layer etc.
Why it works for this purpose:DPHP is resistant to migration, water extraction, weathering and aging, so that PVC waterproof membranes retain their softness and mechanical properties, even when immersed for a long period in water, exposed to sun and subject to temperature fluctuations, and prevent hardening and cracking caused by plasticizer precipitation; its low temperature flexibility means it will not crack during low temperature construction and use in winter.
Application areas: architectural decoration and public utilities.
Matching products: robust floors (commercial/domestic), PVC floors, wallpaper, PVC decorative film, furniture edge banding, skirting boards, floor coverings, etc.
Why it works for this purpose: DPHP provides a hard floor with long-lasting softness and resilience, resistance to indentation, abrasion and cleaning agents. It is essentially non-volatile and non-migrating, so oily/sticky surfaces and indoor air quality problems are avoided. It meets the durability and environmental protection requirements for high-traffic public buildings such as schools and shopping malls.
Application areas： Synthetic leather manufacture for consumer products.
Matching products: sofa leather, seat leather, bag leather, shoe upper leather, clothing leather, belt leather, glove leather, decorative leather etc.
Why it works for this purpose: DPHP softens, plumps and strengthens PVC coatings, providing good compatibility with surface resins to produce soft, wear resistant, cold resistant and crack resistant products; its low migration prevents oil stains from being released from the leather surface during long term use, making it a high quality plasticizer for synthetic leather in furniture and consumer goods.
Application areas： Industrial rubber and plastic products.
Matching products:PVC conveyor belts, industrial hoses, sprinkler hoses, vacuum cleaner hoses, sealing strips, sealing rings, corrugated pipes, equipment protective covers, etc.
Why it works for this purpose: DPHP gives the product good flexibility, oil, water and chemical resistance and wide temperature range performance. Low volatility and low migration ensure long term service without hardening and contaminating the transported medium suitable for harsh working conditions such as mining, agriculture and chemical industries.
Application areas： textile coating, outdoor products.
Matching products:tarpaulin tarpaulin, advertising inkjet cloth, sunshade tarpaulin, tent fabric, inflatable boat/inflatable mat, raincoat fabric, swimming ring, marine fabric, protective fabric and so on.
Why it works for this purpose:DPHP is weatherproof, UV resistant and water extractable. It will not make coated fabrics brittle, oily or sticky after long-term exposure outdoors. Its low temperature flexibility means fabrics will not crack when rolled up at low temperatures for outdoor coated fabrics and is a reliable plasticizing solution.
Application areas： Sealing and bonding in the construction and automotive and industrial sectors.
Matching products: building sealants, automotive sealants, PVC plastisol adhesives, carpet backing adhesives, filter media adhesives etc.
Why it works for this purpose: DPHP is rheologically compatible with PVC plastisol systems, providing excellent adhesion, elastic recovery, and weather/water resistance to the sealant. Once cured it remains flexible and can absorb long-term displacement and vibration of building joints and vehicle body welds.
Application areas：Footwear and footwear production industry.
Matching products:PVC shoe soles, slippers, sandals, sports shoe parts, working shoe soles, foamed shoe soles, etc.
Why it works for this purpose:DPHP gives a soft, wear-resistant, flexible sole that will not crack at low temperatures, making the products light in weight, easy and comfortable to wear. Low migration prevents color bleeding and pollution in the upper and sole, and increases the life of the footwear (restricted for children’s products and toys, which need to be assessed according to regulations).
Application areas： Home maintenance and DIY repair.
Matching products: PVC repair glue, waterproof paint repair agent, pipe repair tape, sealant and repair paste, home maintenance spray etc.
Why it works for this purpose: DPHP is present in home maintenance products, according to the US CPID Home Products Database. The repair agent can be well compatible with the original PVC products due to its compatibility with PVC and low migration, thus enabling long-lasting repairs. The waterproof coating is flexible and durable and is the closest application of this product in everyday consumer channels.
Bis(2-propylheptyl) phthalate (DPHP, C 28 H 46 O 4 , CAS 53306-54-0, molecular weight 446.67) is a high molecular weight, heat resistant phthalate plasticizer. It is used in applications ranging from high voltage cables to automotive cabins, and from roofing waterproofing membranes to shopping mall resilient flooring. Because of its low volatility, non-migratory properties, electrical insulating properties, low temperature flexibility and high compatibility with PVC, it is widely used in eleven major areas such as PVC wire and cable insulation sheathing materials, automotive interiors and artificial leather, automotive undercoatings and body sealants, building waterproofing membranes, resilient flooring and wallpaper, synthetic leather, industrial conveyor belts and hoses, coated fabrics, sealants and adhesives, footwear and home maintenance products. Two core high value added sectors among them are wire and cable and automotive interiors.
