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Sustainable Soil Surfactants
for Turfgrass Management
DATE                      AUTHOR
       October 13, 2010            PAUL T. BIALLY
Irrigation Efficiency
      in Turfgrass Systems

Water use efficiency and conservation are essential
for sustainable turfgrass management.

                   The slightest water deficits can
                 impact turf health, appearance, and
                             performance.

                Excessive irrigation can be equally
                  detrimental leading to increased
                 erosion, run-off, nutrient leaching,
                disease susceptibility, and resource
                                costs.
Irrigation Efficiency
        in Turfgrass Systems
Achieved when turf being irrigated uses most
of the water applied by irrigation systems.

Dependent on:
 1. water being applied as uniformly as possible

 2. water being applied in proper amounts at
    appropriate time intervals
                                        source
Irrigation Efficiency
                 Benefits
• Improved appearance
• Better playing conditions (golf, sports fields)

• Reduced water use
• Reduced runoff and leaching
• Reduced agrochemical usage
• Reduced pump operation, energy, and
   maintenance costs
                                           source
Mechanical Advances Are Essential


Allow growers to       Unable to control delivery
control timing,        of applied water below the
duration, and           surface and into the root
uniformity of water        zone, where many
applied to the plant    agronomic and economic
and soil surface.         benefits are realized.
The Impact of Impervious Land Cover*
 Natural Ground Cover                 10-20% Impervious Surface


        10% Runoff                                  20% Runoff




35-50% Impervious Surface                 75-100% Impervious Surface
                                                             55% Runoff

                 30% Runoff




            *roads, parking lots, sidewalks, roof tops, patios, etc.
Esterified
Water Droplet Interaction
          with the Land Surface

                                                       air
                       air
                                          water


               water
            land surface               land surface

      contact angle <90°             90° or greater
           infiltration              no infiltration

   influenced biochemically by oils and waxes from
plants, microbes, agrochemical residue, pollutants, etc.
Prior Discoveries




* Intellectual property of Aquatrols Corp (Paulsboro, NJ, USA)
Irrigation Surfactant Development

There is an ongoing
    need for new
 technologies with
      superior
 performance and
   environmental
      profiles.
Organic Chemistry of Esters




        Esterification:
    O                                O

 R—C—OH       + R’—OH            R—C—O—R’ + H2O

   ACID            ALCOHOL           ESTER
  Carboxylic acid derivatives in which hydroxyl group
      (-OH) is replaced by an alkoxy group (-OR)
Synthesis of Alkyl Polyglucosides


         OH

               O
 OH
   OH                OH       HO                          H+
               OH         +
                                                  n       -H O
                                                            2

              GLUCOSE                    FATTY
         OH                             ALCOHOL
                O
  OH
    OH               O
                OH
                              O
               OH
                OH                 O
                              OH
                                                      n
                                    m


                                      ALKYL
                                  POLYGLUCOSIDE
Synthesis of Alkyl Polyglucoside Esters (AGEs)
                          OH

                               O
                    OH
                     OH               O
                               OH
                                          O
                               OH
                                 OH            O
                                          OH
                                                                    n
                                               m

                               Alkylpolyglucoside
                                        +




    1) Maleic Anhydride                            1) Citric Acid               1) Tartaric Acid
     2) Sodium Sulfite                         2) Sodium Hydroxide            2) Sodium Hydroxide




Alkylpolyglucoside              Alkylpolyglucoside                   Alkylpolyglucoside
 Sulfosuccinate                           Citrate                         Tartrate
AGEs Retain Favorable APG
             Properties…
                                                Free from dioxane,
  Derived from              Biodegradable,      ethylene oxide, and
natural, renewable          not harmful to         nitrosamine
  raw materials            the environment          precursors


                                        Strong biological
             Mild to skin and           performance as
             non-irritating to          built-in and tank
                the eyes                 mix adjuvants
AGEs Offer Unique Efficacy
                          PATENT PENDING


                        ISAA 2007




ISAA 2010
Hydrophobicity* Effects on
   Water Penetration


   1%           5%           10%
 WETTABLE    WETTABLE    REPELLENT




   15%         20%           50%
STRONGLY    IMPERVIOUS   IMPERVIOUS
REPELLENT

      *Dimethyldichlorosilane treatments
Droplet Penetration Effects
                                     WDPT (s)
     Treatment       8000mgL-1   2000mgL-1 1000mgL-1 500mgL-1
    Citrate Ester       2.0        52.6       68.0    155.0
   Tartrate Ester       2.0        61.4       83.3    180.0
Sulfosuccinate Ester    2.8        65.2      100.7    135.0
         L61            4.2        110.6     128.3    325.9
        31R1            5.5        121.0     284.2    471.8
         L62            8.0        152.7     167.9    468.4
        25R2            9.8        203.3     394.4     >600
         L64            8.0        511.4      >600     >600
    APG (C8-10)         3.0        >600       >600     >600
    APG (C9-11)         3.0        >600       >600     >600
                                   Top 3 performers in GREEN
Droplet Penetration Effects
Time (s)

   600
   500
   400
    300
    200
    100
           0




           8000mgL-1   2000mgL-1   1000mgL-1   500mgL-1
Favorable Combinations with
Commonly Used Surfactants
                           WDPT (s)
            Treatment      2000mgL-1
      L61 Block Copolymer    305.9
      APG (C8-10)            280.9
      1:1 APG to L61         72.7
      Sulfosuccinate Ester   23.4
      1:1 SS to L61           5.0




                              OTS-treated sand
Effect of Blending Ratio
 on Wetting Efficacy
                                              WDPT (s)
                                              2000mgL-1
                 Treatment                 3:1 1:1 1:3
Citrate Ester + Block Copolymer           71.8 37.2 330.0
Tartrate Ester + Block Copolymer          51.8 41.6 128
Sulfosuccinate Ester + Block Copolymer    140 57.8 480




                                   OTS-treated sand
                              GREEN denotes synergies
Mini Disk Infiltrometer (MDI)
              •Measures hydraulic conductivity and infiltration
                  rate of the medium it is placed upon.

                 •Can also be used to measure soil water
               repellency index and evaluate wetting agent
                                 efficacy.




                    bottom view
Property of Decagon Devices, 2007.
Mini Disk Infiltrometer (MDI)
                Infiltration = I = C1t + C2√t
              Hydraulic Conductivity = k = C1/A

                   where C1 is the slope of the curve of
                cumulative infiltration vs square root of time



               and      A = 11.65(n0.1-1)exp [2.92(n-1.9)αh0]

                                                (αr0)0.91

                                related to soil parameters


Property of Decagon Devices, 2007.
Hydrophobicity* Effects on
 Water Penetration Rate


   1%            5%           10%
  1.4 mL/s     1.3 mL/s     1.0 mL/s




   15%          20%          50%
 0.7 mL/s     0.0 mL/s      0.0 mL/s


       *Dimethyldichlorosilane treatments
Natural Variations in Infiltration Rate
               (mL/s)

       0.23   0.13   0.13


15ft   0.33   0.27   0.23


       0.30   0.33   0.40

              15ft
Infiltration Rate (mL/s)
      following 1.0” Rain Event
                             Mean
                       Infiltration Rate
    Time after rain   mL/s       mL/min
30 minutes            0.47          28
24 hours              0.30          18
48 hours              0.20          12
72 hours              0.10           6
96 hours              0.10           6
Infiltration Rate (mL/s)
     with Surfactant Treatment
                               Mean
                         Infiltration Rate
                   -1
 Treatment (500mgL )    mL/s       mL/min
Control (96 hr)         0.10           6
C8-10 APG               0.10           6
L62                     0.13           8
Citrate Ester           0.15           9
Tartrate Ester          0.15           9
Sulfosuccinate ester    0.17          10
1:1 EC to L62           0.23          14
Conclusions and Future Outlook

Performance advantages are apparent in the
 esterification of nonionic APGs.
APG esters can be highly effective at
 delivering irrigation water and
 agrochemicals to the root zone of turfgrass.
 Synergies are apparent with commonly
 used surfactants.
Patent pending. Research is underway to
 further investigate these properties.

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Sustainable Soil Surfactants for Turfgrass Management

  • 1. Sustainable Soil Surfactants for Turfgrass Management DATE AUTHOR October 13, 2010 PAUL T. BIALLY
  • 2. Irrigation Efficiency in Turfgrass Systems Water use efficiency and conservation are essential for sustainable turfgrass management. The slightest water deficits can impact turf health, appearance, and performance. Excessive irrigation can be equally detrimental leading to increased erosion, run-off, nutrient leaching, disease susceptibility, and resource costs.
  • 3. Irrigation Efficiency in Turfgrass Systems Achieved when turf being irrigated uses most of the water applied by irrigation systems. Dependent on: 1. water being applied as uniformly as possible 2. water being applied in proper amounts at appropriate time intervals source
  • 4. Irrigation Efficiency Benefits • Improved appearance • Better playing conditions (golf, sports fields) • Reduced water use • Reduced runoff and leaching • Reduced agrochemical usage • Reduced pump operation, energy, and maintenance costs source
  • 5. Mechanical Advances Are Essential Allow growers to Unable to control delivery control timing, of applied water below the duration, and surface and into the root uniformity of water zone, where many applied to the plant agronomic and economic and soil surface. benefits are realized.
  • 6. The Impact of Impervious Land Cover* Natural Ground Cover 10-20% Impervious Surface 10% Runoff 20% Runoff 35-50% Impervious Surface 75-100% Impervious Surface 55% Runoff 30% Runoff *roads, parking lots, sidewalks, roof tops, patios, etc.
  • 7.
  • 9. Water Droplet Interaction with the Land Surface air air water water land surface land surface contact angle <90° 90° or greater infiltration no infiltration influenced biochemically by oils and waxes from plants, microbes, agrochemical residue, pollutants, etc.
  • 10. Prior Discoveries * Intellectual property of Aquatrols Corp (Paulsboro, NJ, USA)
  • 11. Irrigation Surfactant Development There is an ongoing need for new technologies with superior performance and environmental profiles.
  • 12.
  • 13. Organic Chemistry of Esters Esterification: O O R—C—OH + R’—OH R—C—O—R’ + H2O ACID ALCOHOL ESTER Carboxylic acid derivatives in which hydroxyl group (-OH) is replaced by an alkoxy group (-OR)
  • 14. Synthesis of Alkyl Polyglucosides OH O OH OH OH HO H+ OH + n -H O 2 GLUCOSE FATTY OH ALCOHOL O OH OH O OH O OH OH O OH n m ALKYL POLYGLUCOSIDE
  • 15. Synthesis of Alkyl Polyglucoside Esters (AGEs) OH O OH OH O OH O OH OH O OH n m Alkylpolyglucoside + 1) Maleic Anhydride 1) Citric Acid 1) Tartaric Acid 2) Sodium Sulfite 2) Sodium Hydroxide 2) Sodium Hydroxide Alkylpolyglucoside Alkylpolyglucoside Alkylpolyglucoside Sulfosuccinate Citrate Tartrate
  • 16. AGEs Retain Favorable APG Properties… Free from dioxane, Derived from Biodegradable, ethylene oxide, and natural, renewable not harmful to nitrosamine raw materials the environment precursors Strong biological Mild to skin and performance as non-irritating to built-in and tank the eyes mix adjuvants
  • 17. AGEs Offer Unique Efficacy PATENT PENDING ISAA 2007 ISAA 2010
  • 18. Hydrophobicity* Effects on Water Penetration 1% 5% 10% WETTABLE WETTABLE REPELLENT 15% 20% 50% STRONGLY IMPERVIOUS IMPERVIOUS REPELLENT *Dimethyldichlorosilane treatments
  • 19. Droplet Penetration Effects WDPT (s) Treatment 8000mgL-1 2000mgL-1 1000mgL-1 500mgL-1 Citrate Ester 2.0 52.6 68.0 155.0 Tartrate Ester 2.0 61.4 83.3 180.0 Sulfosuccinate Ester 2.8 65.2 100.7 135.0 L61 4.2 110.6 128.3 325.9 31R1 5.5 121.0 284.2 471.8 L62 8.0 152.7 167.9 468.4 25R2 9.8 203.3 394.4 >600 L64 8.0 511.4 >600 >600 APG (C8-10) 3.0 >600 >600 >600 APG (C9-11) 3.0 >600 >600 >600 Top 3 performers in GREEN
  • 20. Droplet Penetration Effects Time (s) 600 500 400 300 200 100 0 8000mgL-1 2000mgL-1 1000mgL-1 500mgL-1
  • 21. Favorable Combinations with Commonly Used Surfactants WDPT (s) Treatment 2000mgL-1 L61 Block Copolymer 305.9 APG (C8-10) 280.9 1:1 APG to L61 72.7 Sulfosuccinate Ester 23.4 1:1 SS to L61 5.0 OTS-treated sand
  • 22. Effect of Blending Ratio on Wetting Efficacy WDPT (s) 2000mgL-1 Treatment 3:1 1:1 1:3 Citrate Ester + Block Copolymer 71.8 37.2 330.0 Tartrate Ester + Block Copolymer 51.8 41.6 128 Sulfosuccinate Ester + Block Copolymer 140 57.8 480 OTS-treated sand GREEN denotes synergies
  • 23. Mini Disk Infiltrometer (MDI) •Measures hydraulic conductivity and infiltration rate of the medium it is placed upon. •Can also be used to measure soil water repellency index and evaluate wetting agent efficacy. bottom view Property of Decagon Devices, 2007.
  • 24. Mini Disk Infiltrometer (MDI) Infiltration = I = C1t + C2√t Hydraulic Conductivity = k = C1/A where C1 is the slope of the curve of cumulative infiltration vs square root of time and A = 11.65(n0.1-1)exp [2.92(n-1.9)αh0] (αr0)0.91 related to soil parameters Property of Decagon Devices, 2007.
  • 25. Hydrophobicity* Effects on Water Penetration Rate 1% 5% 10% 1.4 mL/s 1.3 mL/s 1.0 mL/s 15% 20% 50% 0.7 mL/s 0.0 mL/s 0.0 mL/s *Dimethyldichlorosilane treatments
  • 26. Natural Variations in Infiltration Rate (mL/s) 0.23 0.13 0.13 15ft 0.33 0.27 0.23 0.30 0.33 0.40 15ft
  • 27. Infiltration Rate (mL/s) following 1.0” Rain Event Mean Infiltration Rate Time after rain mL/s mL/min 30 minutes 0.47 28 24 hours 0.30 18 48 hours 0.20 12 72 hours 0.10 6 96 hours 0.10 6
  • 28. Infiltration Rate (mL/s) with Surfactant Treatment Mean Infiltration Rate -1 Treatment (500mgL ) mL/s mL/min Control (96 hr) 0.10 6 C8-10 APG 0.10 6 L62 0.13 8 Citrate Ester 0.15 9 Tartrate Ester 0.15 9 Sulfosuccinate ester 0.17 10 1:1 EC to L62 0.23 14
  • 29. Conclusions and Future Outlook Performance advantages are apparent in the esterification of nonionic APGs. APG esters can be highly effective at delivering irrigation water and agrochemicals to the root zone of turfgrass. Synergies are apparent with commonly used surfactants. Patent pending. Research is underway to further investigate these properties.