Fatty acids, C15-18, tetramethylpiperidinyl esters
[CAS# 86403-32-9]

Identification

• Classification: Organic raw materials >> Carboxylic compounds and derivatives >> Carboxylic esters and their derivatives
• Name: Fatty acids, C15-18, tetramethylpiperidinyl esters
• Synonyms: 2,3-dimethyl-4-propan-2-ylcyclohexan-1-ol, 2,3-dimethyl-6-propan-2-ylcyclohexan-1-ol, 2,4-dimethyl-6-propan-2-ylcyclohexan-1-ol, 2,5-dimethyl-4-propan-2-ylcyclohexan-1-ol, 2,6-dimethyl-4-propan-2-ylcyclohexan-1-ol, 3,5-dimethyl-2-propan-2-ylcyclohexan-1-ol, 3,5-dimethyl-4-propan-2-ylcyclohexan-1-ol, 3,6-dimethyl-2-propan-2-ylcyclohexan-1-ol, 4,5-dimethyl-2-propan-2-ylcyclohexan-1-ol
• Molecular Formula: C₉₉H₁₉₈O₉
• Molecular Weight: 1532.63
• CAS Registry Number: 86403-32-9
• EC Number: 415-430-8
• SMILES: CC1CCC(C(C1C)O)C(C)C.CC1CCC(C(C1C(C)C)O)C.CC1CC(C(C(C1)C(C)C)O)C.CC1CC(C(C(C1)O)C(C)C)C.CC1CC(CC(C1O)C)C(C)C.CC1CC(CC(C1C(C)C)C)O.CC1CC(C(CC1C)O)C(C)C.CC1CC(C(CC1O)C)C(C)C.CC1C(C(CCC1C(C)C)O)C

Safety Data

• Hazard Symbols: GHS05;GHS07;GHS09 Danger
• Hazard Statements: H317-H318-H400-H410
• Precautionary Statements: P261-P264+P265-P272-P273-P280-P302+P352-P305+P354+P338-P317-P321-P333+P317-P362+P364-P391-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute hazardous to the aquatic environment	Aquatic Acute	1	H400
Serious eye damage	Eye Dam.	1	H318
Skin sensitization	Skin Sens.	1	H317
Chronic hazardous to the aquatic environment	Aquatic Chronic	1	H410
Skin sensitization	Skin Sens.	1A	H317

Discovory and Applicatios

Fatty acids, C15-18, tetramethylpiperidinyl esters are a class of organic compounds developed within the field of polymer stabilization and materials chemistry. They consist of long-chain fatty acids with carbon numbers typically ranging from fifteen to eighteen that are esterified with tetramethyl-substituted piperidinol derivatives. These substances belong to the broader family of hindered amine derivatives, which were identified in the mid twentieth century as highly effective stabilizers for polymers exposed to light, heat, and oxygen.

The discovery of fatty acid tetramethylpiperidinyl esters is closely linked to research on polymer degradation that accelerated after the widespread adoption of synthetic plastics. Early polymer products often suffered from rapid deterioration when exposed to sunlight and atmospheric oxygen, leading to discoloration, embrittlement, and loss of mechanical strength. Chemists initially relied on phenolic antioxidants and ultraviolet absorbers, but these additives had limited effectiveness over long periods. Systematic investigations into nitrogen-containing compounds revealed that sterically hindered amines, particularly those based on the tetramethylpiperidine structure, exhibited unusual and highly effective stabilization behavior.

The key breakthrough came when researchers recognized that the tetramethylpiperidine moiety could participate in cyclic radical scavenging processes without being permanently consumed. This property distinguished hindered amine stabilizers from conventional antioxidants. Further work showed that modifying these molecules with long-chain fatty acid esters improved their compatibility with hydrophobic polymer matrices. Fatty acids in the C15-18 range, commonly derived from natural sources such as tallow or vegetable oils, were found to be especially suitable. Esterification with these acids produced materials that were sufficiently nonpolar to disperse uniformly within polyolefins and other plastics.

As a result, fatty acids, C15-18, tetramethylpiperidinyl esters emerged as practical industrial additives rather than purely academic compounds. Their development was driven by empirical optimization of molecular structure, focusing on balancing stabilization efficiency, thermal stability, and processability. By the late twentieth century, these esters had become established components in the formulation of light stabilizer systems.

The primary application of fatty acids, C15-18, tetramethylpiperidinyl esters is in the stabilization of polymers against photooxidative degradation. They are widely used in polyolefins such as polyethylene and polypropylene, which are particularly susceptible to ultraviolet-induced damage. When incorporated into these materials, the esters help inhibit the formation and propagation of free radicals generated by exposure to sunlight and heat. This action significantly extends the service life of plastic products used outdoors, including films, fibers, pipes, and molded components.

In addition to polyolefins, these stabilizers have been applied in other polymer systems, including polyurethanes, styrenic polymers, and elastomers. In coatings and paints, fatty acid tetramethylpiperidinyl esters contribute to resistance against chalking, cracking, and color fading. Their long alkyl chains enhance compatibility with organic binders, reducing the tendency for migration to the surface or loss during processing. This permanence is a critical advantage in applications requiring long-term durability.

Another important area of application is in agricultural and construction materials. Plastic greenhouse films, irrigation components, and building products are often exposed to intense sunlight for extended periods. The use of fatty acids, C15-18, tetramethylpiperidinyl esters in these materials has helped improve reliability and reduce maintenance and replacement costs. Their effectiveness over long exposure times has been demonstrated through standardized weathering tests and extensive industrial experience.

From a formulation perspective, these compounds are often used in combination with other stabilizers, such as ultraviolet absorbers and antioxidants. Such synergistic systems provide broader protection by addressing multiple degradation pathways. The fatty acid ester structure allows formulators to tailor solubility, melting behavior, and compatibility to match specific polymers and processing conditions.

Beyond their practical uses, fatty acids, C15-18, tetramethylpiperidinyl esters have also played a role in advancing scientific understanding of stabilization mechanisms. Studies of their behavior under oxidative stress have contributed to the general model of hindered amine stabilization, which is now a cornerstone concept in polymer chemistry.

In summary, fatty acids, C15-18, tetramethylpiperidinyl esters are the result of targeted research into polymer durability and the chemistry of hindered amines. Their discovery arose from efforts to address the limitations of earlier stabilizers, and their applications are firmly established in plastics, coatings, and other materials requiring long-term resistance to environmental degradation.

References

2015. Cyclohexyl carbamate compounds as skin and/or hair lightening actives. US Patent (granted).
URL: US-9072676-B2

2013. Cyclohexyl carbamate compounds as skin and/or hair lightening actives. US Patent Application.
URL: US-2013156710-A1