Cardura E10P Glycidyl Ester - momentive.com · Cardura™ E10P Glycidyl Ester A Building Block for...
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Technology Backgrounder
Cardura™ E10P Glycidyl EsterA Building Block for Acrylic Resins
Cardura E10P Monomer
Cardura E10P monomer is the glycidyl ester of Versatic™ Acid 10, a highly branched carboxylic acid containing 10 carbon atoms.
Cardura E10P monomer is a bulky and hydrophobic intermediate which is easily incorporated into resins via its reactive epoxy group. It is used in a wide range of applications such as automotive coatings (refinish and OEM topcoats), general metal coatings, and pigment pastes.
Characteristics:
Carbon-durable glycidyl ester with a backbone of 10 carbon atoms:■■ Epoxy equivalent weight approxi-mately: 240 g /mol
■■ Epoxy group content approximately: 4170 mmol / kg
■■ Boiling range: 251 – 278 °C (5 – 95 %)■■ Low viscosity (23 °C): 7 mPa·s■■ High flame / flash point■■ Low colour■■ Low vapour pressure■■ EINECS and TSCA listed
Glycidyl Ester
Structural Features:■■ Epoxy group
Performance Characteristics:■■ Highly reactive towards amines, acids, alcohols
■■ Enhanced metal adhesion
Versatic Acid 10 R1 + R2 = 7 carbon atoms
Structure and Properties:■■ Sterically protected ester group■■ Bulky structure
Performance Characteristics:■■ Excellent compatibility with polar solvents
■■ Excellent acid and alkali resistance■■ Superior outdoor durability■■ Improved gloss■■ Improved pigment utilization■■ Low solution viscosity■■ High solids resins■■ Improved polar solvent resistance■■ Excellent solubility in aliphatic solvents
CH3
R2
R1CCO
OCH2CHO
CH2
Cardura E10P monomer as building block for Polymers
CH3
R2
R1 CCH2 CHHC 2
OCO
O
> 100 °CRCOOH
catalyst
CH3
R2
R1 CO
OC
O
O
OH
R
Acid-Epoxy
> 20 °C
Amine-Epoxy
~ 150 °C
Phenol-Epoxy
> 120 °C
catalyst
Alcohol-Epoxy
CH3
R2
R1
NRC
O
O
OH2
OH
CH3
R2
R1
OC
O
O
R
CH3
R2
R1
ORC
O
O
OH
R NH2
ROH
OHR
+
+
+
+
Viscosity / co-solvent content:
Cardura E10P monomer reduces the resin viscosity as the polymer has a shorter chain length at the same molec-ular weight. Its bulky structure also limits the chain interactions. Therefore the solvent content of solvent-borne paints or the co-solvent content of water-based paints can be reduced.
Resin solubility and pigment dispersion:
Cardura E10P monomer is an am-bivalent molecule, both hydrophobic and polar. This explains the improved solubility of Cardura E10P glycidyl ester based resins in both polar and non polar solvents, permitting the use of weaker solvent blends and the ability to improve the pigment dispersion.
Introduction of hydroxyl groups:
Cardura E10P monomer introduces hy-droxyl groups into the resin via reaction with carboxylic acid or an amine. These resins can be used, in combination with other hydroxy-functional intermediates, for reaction with the cross-linker, e.g. melamine formaldehyde and polyisocya-nate resins.
Chemical Resistance:
Cardura E10P monomer improves the chemical resistance of coatings by reducing the permeability to polar and aggressive chemicals and by the steric protection of its own and adjacent ester bonds.
Cardura E10P monomer in Acrylic Resins
Cardura E10P monomer is readily incor-porated into acrylic resins via reaction with an unsaturated acid (e.g. Acrylic Acid). Thanks to its low viscosity, Car-dura E10P monomer can be used in the initial reactor charge as reactive solvent to increase reaction throughput.
The addition of ACE monomer to acry-late resins is comparable to a combina-tion of hydroxyfunctional and hydropho-bic monomers.
For example: ■■ HydroxyEthylAcrylate, ■■ HydroxyEthylMethacrylate, ■■ HydroxyPropylMethacrylate, ■■ EthylHexylAcrylate,■■ isoBornylMethacrylate
The higher the concentration of Cardura E10P monomer, the lower the polymer viscosity:
The higher the level of Cardura E10P monomer, the better the acid resistance of the coating:
Effect of Cardura E10P monomer on polymer solution viscosity and acid resistance
Cardura E10P monomer leads to lower viscosity acrylic resins which are used for low VOC applications.
16,000
14,000
12,000
10,000
4,000
0
8,000
6,000
2,000
10 20 30 40
Cardura E10P MonomerConcentration[ % m/m ]
Mw approx. 16,000 / Tg (Fox) = 40 °CMw approx. 20,000 / Tg (Fox) = 30 °C
Mw approx. 10,000 / Tg (Fox) = 30 °C
Vis
cosi
ty [
mP
a·s
]
26
24
22
20
14
10
18
16
12
10 20 30 40
Cardura E10P Monomer Concentration [ % m/m ]
Aci
d re
sist
ance
sco
re
0 = poor / 30 = excellent
OH
OCHCH2
CH3
R2
R1CCO
O
CH2
OH
OCCH
CH2
O
+CH3
R2
R1CCO
OCH2CHO
CH2
Cardura Glycidyl Ester Acrylic Acid ACE Monomer
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