Bis(2,2,6,6-tetramethyl-4-piperidyl)sebacate
[CAS# 52829-07-9]

Identification

• Classification: Organic raw materials >> Heterocyclic compound >> Piperidines
• Name: Bis(2,2,6,6-tetramethyl-4-piperidyl)sebacate
• Synonyms: Decanedioic acid bis(2,2,6,6-tetramethyl-4-piperidinyl)ester
• Molecular Formula: C₂₈H₅₂N₂O₄
• Molecular Weight: 480.73
• CAS Registry Number: 52829-07-9
• EC Number: 258-207-9
• SMILES: CC1(CC(CC(N1)(C)C)OC(=O)CCCCCCCCC(=O)OC2CC(NC(C2)(C)C)(C)C)C

Properties

• Density: 1.0±0.1 g/cm³, Calc.^*
• Melting point: 82-85 °C
• Index of Refraction: 1.498, Calc.^*
• Boiling Point: 499.8±45.0 °C (760 mmHg), Calc.^*
• Flash Point: 256.0±28.7 °C, Calc.^*, 216 °C

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS05;GHS07;GHS08;GHS09 Danger
• Risk Statements: H315-H318-H319-H361f-H400-H411
• Safety Statements: P203-P264-P264+P265-P273-P280-P302+P352-P305+P351+P338-P305+P354+P338-P317-P318-P321-P332+P317-P337+P317-P362+P364-P391-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Chronic hazardous to the aquatic environment	Aquatic Chronic	2	H411
Eye irritation	Eye Irrit.	2	H319
Serious eye damage	Eye Dam.	1	H318
Acute hazardous to the aquatic environment	Aquatic Acute	1	H400
Skin irritation	Skin Irrit.	2	H315
Reproductive toxicity	Repr.	2	H361f
Chronic hazardous to the aquatic environment	Aquatic Chronic	1	H410
Reproductive toxicity	Repr.	2	H361
Acute toxicity	Acute Tox.	3	H331
Acute toxicity	Acute Tox.	2	H330
Specific target organ toxicity - single exposure	STOT SE	3	H335
Acute toxicity	Acute Tox.	1	H330

• Transport Information: UN 3077

Discovery and Applications

Bis(2,2,6,6-tetramethyl-4-piperidyl)sebacate, often referred to as Tinuvin 770, is a chemical compound that belongs to the class of hindered amine light stabilizers (HALS). Discovered in the late 20th century, this substance was developed as a means to protect polymers and coatings from degradation caused by ultraviolet (UV) radiation. The need for effective UV stabilizers became increasingly important with the growing use of synthetic materials in various applications, particularly in outdoor environments where exposure to sunlight can significantly reduce the lifespan of products.

The synthesis of Bis(2,2,6,6-tetramethyl-4-piperidyl)sebacate involves the reaction of sebacic acid with 2,2,6,6-tetramethyl-4-piperidinol. The resulting compound features a piperidine ring that provides excellent stability and efficacy as a light stabilizer. Its unique structure allows it to effectively scavenge free radicals generated by UV light exposure, thereby preventing the photodegradation of polymers.

One of the primary applications of Bis(2,2,6,6-tetramethyl-4-piperidyl)sebacate is in the field of plastics and coatings. It is widely used in polyolefins, polyesters, and other synthetic materials to enhance their resistance to UV-induced degradation. This stabilization is crucial for maintaining the physical and aesthetic properties of products such as outdoor furniture, automotive parts, and construction materials. By incorporating this compound into formulations, manufacturers can significantly extend the service life of their products, reducing the need for frequent replacements and contributing to sustainability.

In addition to its role in protecting materials from UV radiation, Bis(2,2,6,6-tetramethyl-4-piperidyl)sebacate also enhances thermal stability. This dual functionality makes it particularly valuable in applications where both light and heat resistance are critical. Its compatibility with various polymers allows for versatile use in different formulations, enabling manufacturers to tailor products to meet specific performance requirements.

Moreover, the compound has found applications in the production of coatings and adhesives, where its light-stabilizing properties help maintain the integrity of the final products. In the automotive industry, it is used to protect exterior components from fading and cracking due to prolonged sun exposure. In architectural coatings, it helps preserve the color and appearance of painted surfaces, contributing to the longevity of buildings and structures.

Bis(2,2,6,6-tetramethyl-4-piperidyl)sebacate is generally regarded as safe for use in various applications, although appropriate handling and safety measures should be followed to minimize exposure. Regulatory agencies have evaluated its safety profile, allowing its use in consumer products within specified limits.

Research continues to explore the potential of Bis(2,2,6,6-tetramethyl-4-piperidyl)sebacate in new applications, including its effectiveness in biodegradable polymers and other emerging materials. As environmental concerns grow, the demand for sustainable additives that do not compromise product performance is increasing. The development of this compound represents a significant advancement in material science, offering solutions that balance performance with environmental responsibility.

In summary, Bis(2,2,6,6-tetramethyl-4-piperidyl)sebacate is a vital compound in the field of polymer stabilization, providing effective protection against UV light and thermal degradation. Its discovery has led to enhanced durability of various materials, contributing to the longevity and sustainability of products used in everyday life.

References

2006. Bis(2,2,6,6-tetramethylpiperidin-4-yl) decanedioate. Acta Crystallographica Section E Structure Reports Online, 62(11).
DOI: 10.1107/s1600536806039158

2013. Mass spectrometry contamination from Tinuvin 770, a common additive in laboratory plastics. Journal of biomolecular techniques : JBT, 24(2).
DOI: 10.7171/jbt.13-2402-004

1994. Inhibition of nicotinic acetylcholine receptors by bis (2,2,6,6-tetramethyl- 4-piperidinyl) sebacate (Tinuvin 770), an additive to medical plastics. The Journal of Pharmacology and Experimental Therapeutics, 268(2).
DOI: 10.1016/s0022-3565(25)39002-6