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

Momentive Specialty Chemicals Inc.

World Headquarters180 East Broad Street Columbus, OH 43215-3799

© 2012 Momentive Specialty Chemicals Inc. All rights reserved. ® and ™ denote trademarks owned by or licensed to Momentive Specialty Chemicals Inc. MSC-518 4/12 Printed in U.S.A.

The information provided herein was believed by Momentive Specialty Chemicals (“Momentive”) to be accurate at the time of preparation or prepared from sources believed to be reliable, but it is the responsibility of the user to investigate and understand other pertinent sources of information, to comply with all laws and procedures applicable to the safe handling and use of the product and to determine the suitability of the product for its intended use. All products supplied by Momentive are subject to Momentive’s terms and conditions of sale. MOMENTIVE MAKES NO WARRANTY, EXPRESS OR IMPLIED, CONCERNING THE PRODUCT OR THE MERCHANTABILITY OR FITNESS THEREOF FOR ANY PURPOSE OR CONCERNING THE ACCURACY OF ANY INFORMATION PROVIDED BY MOMENTIVE, except that the product shall conform to Momentive’s specifications. Nothing contained herein constitutes an offer for the sale of any product.

Momentive: The Science Behind What Lies Ahead

At Momentive, our global team is focused on delivering value by helping our customers make their products and processes better. We do this by bringing our deep technical expertise, market experience and technology portfolio to bear on their specific challenges. We are the science behind thousands of innovations that enhance both our customers’ business results…and everyday life.

Reach our Global Customer Service network at:

U.S. and Canada +1 888 443 9466 E-mail: 4information@momentive.com

Europe +800 836 43581 E-mail: 4information.eu@momentive.com

All Others +86 21 3860 4638

Please refer to the literature code MSC-518 when contacting us.