Durazone 37 a Non-Migratory Antiozonant

DURAZONE® 37 A NON-MIGRA NON-M IGRATORY TORY,, HIGH H IGH PERFORMANCE ANTIOZONANT DESIGNED TO MAINTAIN ORIGINAL RUBBER PRODUCT APPEARANCE TOM CROFT TECHNICAL SERVICE MANAGER FOR TIRE AND RUBBER APPLICATIONS

DURAZONE® 37

2,4,6-Tris-(N-1,4-dimethylpentyl-p-phenylenediamino)-1,3,5-triazine

CAS Number : 121246-28-4 Molecular Weight: 694 Melting Point : 70  74C (158  165F)  –

 –

Physical Form: Form: Purple flake Specific Gravity: 1.05 i n water, water, Soluble in hexane, Solubility : Insoluble in benzene, xylene. Slightly soluble in acetone and MEK

BENEFITS OF DURAZONE® IN RUBBER COMPOUNDING

For Nontire producers:

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For Tire producers:

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Can be used in colored compounds where discoloration is a problem Low softening point makes DURAZONE® 37 usable in single pass mixing operations operations No harmful effects on shelf life of mixed compound

Protects the original appearance of tires from unwanted changes due to surface bloom in sidewall and other visible components Can be combined with Naugard Q for synergistic impact on resistance to oxidation and ozonation Equal or improved ozone resistance when compared to 6PPD Can be used in sidewall compounds in contact with white labeling or striping with no problematic staining

IMPORTANT IMPORT ANT FEATURES FEATURES OF DURAZONE® D URAZONE® 37 •

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i n the rubber matrix. Volatilization Volatilization is not High Molecular Weight: Will be stable in a problem in most rubber compounds.

Non-Discoloring : Can be used in light colored compounds without the problems associated with staining or discoloring of traditional antiozonants. Can be Combined with Other Antidegradants : Can be combined with other antidegradants that offer other unique properties such as NAUGARD® Q or OCTAMINE® OCTAMINE® to give giv e a protection package to resist r esist oxidation and ozone attack. These synergistic blends are often very cost effective means to protect a rubber compound. been used with a No Impact on Rubber Compound Physical Properties : Has been variety of elastomer types (NR, SBR, NBR, CR, BR, etc) with minimal or no negative effect on physical properties such as hardness, tensile and elongation.

 APPLICATIONS  APPLICA TIONS FOR DURAZONE® DURAZONE® 37 •

Tire Sidewalls

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Hose Cover

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Windshield Wiper

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 Automotive Trim Trim Tire Tread

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 Athletic Footwear

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 Architectural Seals

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Sponge Compounds

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Playground Equipment

DURAZONE® 37 HAS LITTLE TO NO IMPACT ON CURE RATE

DURAZONE® 37 Impact on Cure Rate Polychloroprene GW Mg Oxide Polyethylene wax N990 Clay ZnO TBTD DOTG OCTAMINE® OCTAMINE® DURAZONE® 37

100 4 3 50 50 5 1.5 0.5 0 0

100 4 3 50 50 5 1.5 0.5 2 0

100 4 3 50 50 5 1.5 0.5 0 2

Rheometer, ts1,min tc90, min

1.2 7.91

1.1 7.72

1.2 7.87

0 @ 160 C

DURAZONE® 37 PERFORMANCE Polychloroprene Polychlor oprene Compound, ASTM D1149, D1149, Ozone Exposure, 50 pphm, Hours to Cracking 1200 1000 800

Hrs to 600 Cracking 400

200 0 Control

Octamine 2 phr

Durazone 37 2 phr  

DURAZONE® 37 SHOWS LITTLE TO NO SURFACE BLOOM Appearance Appearance Change Change in Sidewall Compound Compound SMR 5CV

60

60

EPDM

70

70

N660

45

45

Z nO

3

3

Ste ari c Aci d

1

1

TBBS

0.9

0.9

S ul f ur

1.5

1.5

6PPD

2.4

0

0

2.4

368

378

Durazone 37 Extension Cycling Fatigue Test ASTM D4482 Age d 70 hrs @100C, @100C, KC to fai l ure

DURAZONE® 37 THE NON-MIG NON-MIGRA RATORY TORY ANTIOZON ANTIOZONANT ANT Ozone Aging, Aging, NR / EPDM Sidewall S idewall Compound, Run 72 hrs Continuously, 50 pphm @ 40C

Left 6PPD (2.4 phr) and Right DURAZONE®37 (2.4 phr)

NON-STAINING PERFORMANCE OF DURAZONE® 37 NR Sidewall Compound for Non-staining Non- staining Comparison SMR-5CV N-326 ZnO Stearic Acid Naphthenic Oil TBBS Sulfur DURAZONE® 37 6PPD

100 50 3 1 15 0.7 2.2 4 0

100 50 3 1 15 0.7 2.2 0 4

 Aged 2 weeks, 70 70 0 C  ASTM D573 % Retention Tensile Strength Strengt h Elongation 300% Modulus

121 81 220

118 83 208

NON-STAINING PERFORMANCE OF DURAZONE® 37 Ageing Period 30 Days at Room Temperature

(l) 4.0 PHR 6PPD

(r) 4.0 PHR DURAZONE® 37

IMPROVING DYNAMIC PROPERTIES WITH DURAZONE® 37

DURAZONE® 37 versus v ersus 6PPD in Dynamic Flexing Testing Testing SBR 1502

50

50

SBR 1778

70

70

N234

55

55

ZnO

3

3

Stearic Acid

1

1

DURAZONE® 37

1

0

6PPD

0

1

TBS

0.5

0.5

MBS

0.5

0.5

Sulfur

1.8

1.8

DYNAMIC PROPERTIES PERFORMANCE WITH DURAZONE® 37 6PPD  Antiozonant, phr Dynamic Properties, Cured 10 min. at 177ºC (350ºF) Extension Cycling Fatigue Test - ASTM D4482  Aged 70 hrs at 100ºC (212ºF), (212ºF), kc Dynamic Properties Tangent Delta at 4ºC (39ºF) Tangent Delta at 28ºC (82ºF) Tangent Delta at 53ºC (127ºF) Tangent Delta at 77ºC (171ºF) Tangent Delta at 102ºC (216ºF) Dynamic Modulus (G*) at 4ºC (39ºF), MPa Dynamic Modulus (G*) at 28ºC (82ºF), MPa Dynamic Modulus (G*) at 53ºC (127ºF), MPa Dynamic Modulus (G*) at 77ºC (171ºF), MPa Dynamic Modulus (G*) at 102ºC (216ºF), MPa

Durazone 37 1.0

1.0

82.8

107.4

0.184 0.166 0.143 0.133 0.120 8.53 6.16 4.62 4.00 3.58

0.179 0.155 0.131 0.121 0.120 7.75 5.53 4.34 3.73 3.39

Relationship of tan delta to temperature change equal for DURAZONE® 37 and 6PPD.

Tan delta is an indicator for rolling resistance properties in tire tread compounds. Lower tan delta would indicate improved rolling resistance.

WORKER SAFETY CONCERNS

In addition to the low migration tendencies of DURAZONE® 37 when fully incorporated into a rubber compound, DURAZONE® 37 is quite low for volatility in normal rubber processing conditions.

In normal mixing, milling, extrusion, molding and calendaring operations, there should be minimal to no worker exposure to vaporized DURAZONE® 37.

THERMAL STABILITY OF DURAZONE® DURAZONE ® 37 IN PROCESSING

Weight loss is less than 0.15% from 100  – 150oC

THERMAL STABILITY OF DURAZONE® DURAZONE ® 37 IN PROCESSING

No significant Weight Loss for DURAZONE® 37 Until Well Past Processing Temperatures

CONCLUSIONS

DURAZONE® 37 is capable of providing excellent protection from ozone degradation for many different elastomers DURAZONE® 37 does not significanatly impact the cure rate

DURAZONE® 37 does not discolor or stain in rubber r ubber compounds

DURAZONE® DURAZONE® 37 does not present a threat to worker safety due to off gassing during processing Dynamic properties of compounds with DURAZONE® 37 equal or slightly improved to those using 6PPD