Natural Fragrance Solubilizers

Dennis Abbeduto

Colonial Chemical, Inc.

Outline

• Brief solubilizer overview

• Naturally derived solubilizers

• Performance evaluation

2

Solubilizer Overview

3

What is Fragrance Solubilization?

• Emulsion or dispersion characterized by particle

size

• Generally less than ~600A

• Surfactant alone is water soluble

• Fragrance generally soluble in the surfactant

• High ratio of surfactant to oil

• Usually tolerate infinite dilution

4

Fragrance Characteristics

Odor Class Relative

Polarity

Examples

Floral High Jasmine, rose, lilac, carnation

Fruity Medium Esters, aldehydes, fruity lactones

Menthe Medium Peppermint, spearmint, menthol

Spice/Herbs Medium/Low Spice oils (eugenol)

Citrus Low Terpenes, limonene

Woody Low Cedar, sandalwood, pinene

Medicinal Low Camphor, thymol

Animal Low Ambergris, civet, musk

5

Solubility Parameter

• Measure of cohesive forces between molecules

• Higher numbers tend to be more polar

• Molecules with similar numbers will be miscible

• Molecules with values >9 will tend to be easier

to solubilizer into water

• Polar oils are easier to solubilize than nonpolar

oils

6

Solubilizer Overview

Using the HLB system

Formulation Function Required HLB

Defoaming of aqueous systems 1 – 3

W/O emulsification 4 – 6

Wetting 7 – 9

O/W emulsification 8 – 18

Solubilization 11 – 18

Detergency 13+

7

Solubilizer Overview

Solubilizers with approximate HLB value

Oleth-10 12

PEG-40 Hydrogenated Castor Oil 15

Polysorbate 80 15

Oleth-20 15

Polysorbate 20 17

PEG-60 Hydrogenated Castor Oil 17

Steareth-100 19

8

Solubilizer Overview

•Simple surfactants

•Easily vary the HLB

•Cost

Why are solubilizers made by ethoxylation?

9

Solubilizer Overview

• A by-product of ethoxylation is 1,4-Dioxane:

O

O

O

2

Ethylene Oxide 1,4-Dioxane

10

Naturally Derived Solubilizers

11

What is “Naturally Derived”?

•Major raws from renewable sources

•No waste or toxic by-products

•Safe process methods

•Readily biodegradable

•Non-toxic solvents

12 Principles of Green Chemistry:

Must produce products with comparable performance

12

Sorbitan Oleate Decylglucoside

Crosspolymer (SODC)

• HLB Value: 13

• 65% solids in water

• Moderate foamer

• Straw color

• “Co”polymer of Decyl Glucoside and Sorbitan

Monoleate, using biobased linker

• Patented

• Ecocert/COSMOS, NPA, NSF, 100% Biobased

(USDA)

13

Heptyl Glucoside

• 70% active in water

• Non-foaming

• Low color

• Glucoside from castor oil-derived heptyl alcohol

• Patented

• Ecocert/COSMOS, Ecolabel, 100% Biobased

(ACDV)

14

Sulfoacetate Blend

• Aqua (and) Pentylene Glycol (and) Sodium

Lauryl Sulfoacetate (and) Sodium Oleoyl

Sarcosinate (and) Sodium Chloride (and)

Disodium Sulfoacetate (and) Sodium Oleate

(and) Sodium Sulfate

• 55% solids in water

• Low foaming

• Low color

• Patent pending

• Primarily PEG-free, no NGO approvals

15

Natural Glucosides Blend

• Caprylyl/Capryl Wheat Bran/Straw Glycosides

(and) Aqua (and) Fusel Wheat Bran/Straw

Glycosides (and) Polyglyceryl-5 Oleate (and)

Sodium Cocoyl Glutamate (and) Glyceryl

Caprylate

• 70% active in water

• Moderate foam

• Amber color

• Suggested formulation pH 4.5 – 7.5

• Ecocert/COSMOS

16

Polyglycerol Ester Blend

• Polyglyceryl-4 Caprylate (and) Decyl Glucoside

(and) Sodium Lauroyl Glutamate (and)

Diglycerin (and) Water

• X% active in water

• Moderate foam

• Low color

• Suggested formulation pH > 7

• Ecocert/COSMOS

17

Polyglyceryl Esters

• Polyglyceryl-6 Caprylate (and) Polyglyceryl-4

Caprylate (and) Polyglyceryl-4 Cocoate (and)

Polyglyceryl-6 Ricinoleate

• 100% active in water

• Low color

• Low foam

18

Performance Evaluation

19

Performance Evaluation

20

8 8

7

8

6

>10

10

>10 >10

10

8

7 7 7

10

0

2

4

6

8

10

12

Clary Sage OilOrchidia

Lavendar 40/42Orchidia

Lemongrass OilOrchidia

Lemon Oil ItalianPhoenix

Peppermint OilOrchidia

Am

ou

nt

to s

olu

bili

ze 1

% E

sse

nti

al O

il (%

)

Essential Oil

Premixes with Synthetic Solubilizers

Polysorbate 20

Polysorbate 80

PEG-40 HCO

Premixes of oil and solubilizer were added to DI water and

mixed at 40°C for 5-10 minutes until a clear mixture was

obtained. In all tests, there was 1% fragrance in the system.

Performance Evaluation

21

3.5 3

4.5

7

2.5

>10 >10 >10 >10

9

>10 >10 >10 >10 >10 >10 >10 >10 >10 >10

0

2

4

6

8

10

12

Clary Sage OilOrchidia

Lavendar 40/42Orchidia

Lemongrass OilOrchidia

Lemon Oil ItalianPhoenix

Peppermint OilOrchidia

Am

ou

nt

to s

olu

bili

ze 1

% E

sse

nti

al O

il (%

)

Essential Oil

Premixes with Natural Solubilizers

Crosspolymer

Heptyl Glucoside

Sulfoacetate Blend

PGE Blend

Premixes of oil and solubilizer were added to DI water and

mixed at 40°C for 5-10 minutes until a clear mixture was

obtained. In all tests, there was 1% fragrance in the system.

Performance Evaluation

22

>10

7.5

>10 >10

7.5

>10

10

>10 >10

10

>10 >10 >10 >10 >10

0

2

4

6

8

10

12

Clary Sage OilOrchidia

Lavendar 40/42Orchidia

Lemongrass OilOrchidia

Lemon Oil ItalianPhoenix

Peppermint OilOrchidia

Am

ou

nt

to s

olu

bili

ze 1

% E

sse

nti

al O

il (%

)

Essential Oil

Post-Adds with Synthetic Solubilizers

Polysorbate 20

Polysorbate 80

PEG-40 HCO

1 gram oil in 99 grams water, heated to 40°C. Solubilizer

titrated in 0.5% increments with 5 minute mix time

between increments until clear mixture obtained.

Performance Evaluation

23

5.5

4.5

5.5

9

3.5

>10 10.5

>10

8

9

>10 >10 >10 >10 >10 >10 >10 >10 >10 >10

0

2

4

6

8

10

12

Clary Sage OilOrchidia

Lavendar 40/42Orchidia

Lemongrass OilOrchidia

Lemon Oil ItalianPhoenix

Peppermint OilOrchidia

Am

ou

nt

to s

olu

bili

ze 1

% E

sse

nti

al O

il (%

)

Essential Oil

Post-Adds with Natural Solubilizers

Crosspolymer

Heptyl Glucoside

Sulfoacetate Blend

PGE Blend

1 gram oil in 99 grams water, heated to 40°C. Solubilizer

titrated in 0.5% increments with 5 minute mix time between

increments until clear mixture obtained.

Conclusions

• Naturally derived fragrance solubilizers with

broad regulatory, NGO approvals increasing

• Non-ethoxylated options offer similar, if not

better performance than traditional offerings

• Formulators must be mindful of advantages and

drawbacks for each technology

24

Questions?

Thank you!

25