Para tertiary butylphenol formaldehyde resin

Para tertiary butylphenol formaldehyde resin  Names

Preferred IUPAC name

poly[4-tert-butylphenol-co-formaldehyde]

Other names

* p-tert-butylphenol-formaldehyde resin (PTBP-FR)

Identifiers

CAS Number

* 25085-50-1

PubChem CID

* 104912

CompTox Dashboard (EPA)

* DTXSID7047805

Properties

Chemical formula

| (C10H14O)n*(CH2O)m
Molar mass | Variable
Melting point | 80 °C (176 °F; 353 K)[1]

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Infobox references

Chemical compound

Para tertiary butylphenol formaldehyde resin, also known as p-tert-butylphenol-formaldehyde resin (PTBP-FR), is a thermoplastic phenol-formaldehyde resin found in commercial adhesives, particularly glues used to bond leather and rubber. It has broad usage in a large variety of industries and can be found in many household textile products and craft glues. In particular, it is used in the manufacture of shoes.

## Production

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The main ingredients of any phenol-formaldehyde resin are a phenol or substituted phenol and formaldehyde. The two main components of p-tert-butylphenol-formaldehyde resin are thus p-tert-butylphenol and formaldehyde.[2] There have been a number of patents on their production.[3][4] PTBP-FR is of resol type, formed under basic conditions using an excess of formaldehyde. It contains a mixture of oligomers, with repeating unit −CH2C6H2(OH)(t-Bu)CH2O− predominating over −CH2C6H2(OH)(t-Bu)−. Unlike other resols, it does not cross-link when cured, as the positions para to phenol are already occupied by tert-butyl groups.[5]: 791

## Allergenicity

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PTBP-FR can cause severe allergic contact dermatitis in a significant percentage of individuals who come into contact with the resin. Allergic responses are primarily caused by low molecular weight derivatives of p-tert-butylphenol, including monomeric, dimeric, trimeric, and tetrameric species.[5]: 795 The dimers 5,5'-di-tert-butyl-2,2'-dihydroxy-3,3'-dihydroxymethyl-dibenzyl ether and 5,5'-di-tert-butyl-2,2'-dihydroxy-3-hydroxymethyl-dibenzyl ether are especially potent, demonstrating positive patch test reactions at concentrations as low as 10 ppb.[6]

Most cases of dermatitis result from contact with shoes,[7] watchbands, belts, wet suits, handbags, purses, wallets, hats, fabric glues, furniture and upholstery glues, wood glues, waterproof glues, rubber handled tools, dental bonding resins, box adhesives, disposable diapers, lip liner, and rubber athletic insoles.[8] As of 2002, roughly half of all cases were attributable to occupational exposure.[9] Use of PTBP-FR in manufacturing is ubiquitous across numerous industries and commercial products, but most commonly its usage in the manufacture of shoes is implicated in the majority of cases involving contact dermatitis.[10][11][12]

## References

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1. ^ "p-tert-Butylphenol-formaldehyde copolymer". CAS Common Chemistry. American Chemical Society.
2. ^ Wang, Linfeng; Ma, Wenshi; Lei, Dingfeng; Zhang, Dongqiao (2015-10-01). "Preparation and characterization of para-tertiary-butylphenol formaldehyde resins using dual catalytic-extraction method". Progress in Organic Coatings. 87: 1–9\. doi:10.1016/j.porgcoat.2015.04.024. ISSN 0300-9440.
3. ^ US Patent US3677986A
4. ^ World patent WO2009155747A1
5. ^ a b Zimerson E, Bruze M (2020). "Contact Allergy to Phenol-Formaldehyde Resins". In John S, Johansen J, Rustemeyer T, Elsner P, Maibach H (eds.). Kanerva’s Occupational Dermatology (3rd ed.). Cham: Springer International Publishing. pp. 789–798\. doi:10.1007/978-3-319-68617-2_52. ISBN 978-3-319-68617-2.
6. ^ Zimerson, Erik; Bruze, Magnus (December 2002). "Low-Molecular-Weight Contact Allergens in p-tert-Butylphenol-formaldehyde Resin:". American Journal of Contact Dermatitis. 13 (4): 190–197\. doi:10.1053/ajcd.2002.36641.
7. ^ Herro, Elise; Jacob, Sharon E. (1 March 2012). "p-tert-Butylphenol formaldehyde resin and its impact on children". Dermatitis: Contact, Atopic, Occupational, Drug. 23 (2): 86–88\. doi:10.1097/DER.0b013e31824a64ff. PMID 22653125.
8. ^ Allergens: p-TERT-BUTYLPHENOL FORMALDEHYDE RESIN
9. ^ Marks, James G.; Elsner, Peter; DeLeo, Vincent A. (2002). Contact & occupational dermatology (3rd ed.). St. Louis, Mo: Mosby. p. 121\. ISBN 9780323014731.
10. ^ Shono, Mamiko; Ezoe, Kazuhiko; Kaniwa, Masa-Aki; Ikarashi, Yokhiaki; Kojima, Shigeo; Nakamura, Akitada (1 April 1991). "Allergic contact dermatitis from para-tertiary-butylphenol-formaldehyde resin (PTBP-FR) in athletic tape and leather adhesive". Contact Dermatitis. 24 (4): 281–288\. doi:10.1111/j.1600-0536.1991.tb01723.x. PMID 1868718. S2CID 5995961.
11. ^ Foussereau, J.; Cavelier, C.; Selig, D. (1 October 1976). "Occupational eczema from para-tertiary-butylphenol formaldehyde resins: A review of the sensitizing resins". Contact Dermatitis. 2 (5): 254–258\. doi:10.1111/j.1600-0536.1976.tb03043.x. PMID 138517. S2CID 37691789.
12. ^ Handley, J.; Todd, D.; Bingham, A.; Corbett, R.; Burrows, D. (1 September 1993). "Allergic contact dermatitis from para-tertiary-butylphenol-formaldehyde resin (PTBP-F-R) in Northern Ireland". Contact Dermatitis. 29 (3): 144–146\. doi:10.1111/j.1600-0536.1993.tb03512.x. PMID 8222626. S2CID 39255803.

*[CID]: Compound ID
*[EPA]: U.S. Environmental Protection Agency