3. 2-Amino-2-Methyl-1-Propanol (AMP): A VOC Exemption Story
Mary Redmond, ANGUS Chemical
Western Coatings Symposium
Las Vegas, NV
October 2015

4. Overview: AMP Multifunctional Neutralizer
Volatile Organic Compounds (VOCs)
Path to VOC Exemption
Looking Ahead

5. AMP Multifunctional Neutralizer
ANGUS confidential.

6. AMP Multifunctional Neutralizer
Industry standard
Primary amino alcohol
Amine group bonded to a tertiary carbon
Replacement for more hazardous alternatives
Pigment co-dispersant
Furthers formulation optimization

7. AMP Multifunctional Neutralizer
In Manufacturing Performance
Easier to handle, non-toxic
Lower odor, less fugitive
Enables more optimized grind
Reduces process foam
In the Can Performance
BETTER formulation stability
BETTER pH control and bio-stability
BETTER rheology
BETTER color stability

8. AMP Multifunctional Neutralizer
During Application Performance
Consistent rheology
More uniform color
Lower foam in low-VOC formulations
Less odor
On the Wall Performance
BETTER film integrity
BETTER dispersion
BETTER final color achievement
BETTER stain resistance
BETTER scrub resistance
Less tackiness

9. Overview: AMP Multifunctional Neutralizer
Volatile Organic Compounds (VOCs)
Path to VOC Exemption
Looking Ahead

10. VOCs
Carbon Containing Substances Which Can Impact the Formation of Ground Level or Tropospheric Ozone (O3)

11. VOCs, O3 and Other Contaminants Can Negatively Impact Air Quality
Ozone formation:
NO2. + hn => O + NO.
O + O2 => O3
VOCs increase NO2. concentrations, elevating ozone levels
RH + OH. => H2O + R.
R. + O2 => RO2. (peroxy radical)
RO2. + NO. => RO. + NO2.

12. VOCs and the U.S. EPA
All Carbon Containing (Organic) Materials are VOCs in the U.S. Unless Exempted by U.S. EPA
EPA Lists Negligibly Reactive Compounds in 40 CFR (s); All are Exempted from Regulation
Ethane is the Exempt Compound EPA Uses as a Threshold for Comparison
AMP was Regulated as a VOC by EPA Prior to June 25, 2014

13. Overview: AMP Multifunctional Neutralizer
Volatile Organic Compounds (VOCs)
Path to VOC Exemption
Looking Ahead

14. Path to VOC Exemption for AMP
California Air Resources Board (CARB) determined studies were needed to understand the impact of various consumer product ingredients on ozone formation
In addition to architectural coatings, AMP is widely used in aerosol hair sprays (at higher concentrations) and was chosen by CARB for experimental study
CARB Contracted the University of California Riverside*
Results of environmental (smog) chamber studies and qualitative mechanistic estimates were reported in 2008 by Professor William Carter, director of the study
* Center for Environmental Research and Technology ; Contract No

15. Scientific Basis for Exemption
UC Riverside Smog Chamber Studies
Incremental Reactivity Experiments with AMP were Conducted in 85,000 Liter Reactors
Designed per EPA guidelines
VOC/NOx mixtures were irradiated using black lights
Mixture of VOC surrogates used to simulate air pollution
NOX Mixture: fixed ratio of NO + NO2
Effects on Ozone Formation and Nitric Oxide (NO) Oxidation Rates were Measured

16. US Riverside Smog Chamber*
* Carter, W.P.L., Reactivity Estimates for Selected Consumer Product Compounds (Contract No with CARB, 2008)

17. Maximum Incremental Reactivity AMP vs. Ethane
Maximum Incremental Reactivity (MIR) is the Worst-Case Scenario where O3 Formation is Most Sensitive to VOC*
MIR Values Averaged over 39 City-Specific Scenarios**
AMP: ± 0.57 gm O3 /gm VOC
Ethane: 0.28 ± 0.07 gm O3 /gm VOC
The U.S. EPA agreed that AMP is Less Reactive than Ethane
* Highest NOx levels
** Carter, W. P. L. (2012) Atmospheric Ozone Reactivity Estimates for 2-amino-2-methyl-1-propanol, College of Engineering Center for Environmental Research and Technology (CE-CERT) and Air Pollution Research Center, University of California, Riverside CA92521, September 26, 2012.

18. Reaction Mechanisms of AMP
AMP may actually inhibit ozone formation
UC Riverside Concluded:
“certain types of amines that lack abstractable hydrogens adjacent to the amino groups, were found to have negative impacts on ozone formation”; AMP was cited as “the most important example of this”
Carter Proposed the Following:
CH3C(CH3)(NH2)(CH2OH) + OH. => H20 + CH3C(CH3)(CH2OH)NH.
CH3C(CH3)(CH2OH)NH. + NO2 . => CH3C(CH3)(CH2OH)NHNO2
AMP
Stable, Radical Termination
AMP will not lead to a peroxy radical needed to form ozone
By consuming NO2., AMP will also reduce ozone formation

19. Other Supporting Data EPA Considered Other Factors Regarding AMP:
Atmospheric Availability
Low volatility
Forms hydrogen bonds with water present
Overall Environmental Impact
Zero stratospheric ozone depletion potential
Readily biodegraded and low global warming potential
Health and Safety
Low acute toxicity, non-mutagenic and does not interfere with animal reproduction
Regulatory Status
Not regulated as a hazardous air pollutant (HAP)
Not listed as a toxic chemical (EPCRA)

20. VOC Exemption Petition Success
Petition for VOC exemption Submitted October 2012
Direct Final Rule Issued March [EPA-HQ-OAR ]
Rule Finalized on June 2014
EPA did not receive objections
Only organic amine exempted
From its Final Ruling, EPA Prefers AMP
“AMP’s performance as a multifunctional neutralizer, combined with its reduced ozone potential and favorable toxicity data, makes this product a preferred one compared to more toxic chemicals used for the same purpose”

21. Overview: AMP Multifunctional Neutralizer
Volatile Organic Compounds (VOCs)
Path to VOC Exemption
Looking Ahead

22. California VOC Exemption Petitions
California Requires Separate Rulings to Exempt a Material from Regulation as a VOC
Many of 35 air quality management districts (AQMD) must be petitioned separately
A dozen of the AQMDs follow the U.S. EPA
AMP CA Exemption Process Began in July 2014
Office of Environmental Health Hazard Assessment (OEHHA) assessing toxicity profiles
California Air Resources Board (CARB) evaluating atmospheric data
OEHHA and CARB assessments will be used by most of the AQMDs to make their rulings

23. Summary
AMP has a Long History of Successful Use as a Multifunctional Neutralizer for Architectural Latex Paints
EPA has Exempted AMP from Regulation as a VOC; the Only Organic Amine Exempted thus far
Petitioning of the State of California is in Progress
Paint manufacturers now have AMP to make their BEST Low to No-VOC paint formulations BETTER.

25. Thank you!