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# c12) United States Patent Viswanathan et al. 

# (54) COMPOSITIONS AND METHODS TO PRODUCE TRIAZINE-ARYLHYDROXY-ALDEHYDE CONDENSATES WITH IMPROVED SOLUBILITY 

(75) Inventors: Ganapathy S. Viswanathan, Louisville, KY (US); Raman C. Subrayan, Louisville, KY (US); Vinay Malhotra, Louisville, KY (US) 

(73) Assignee: HEXION INC., Columbus, OH (US) 

( *) Notice: Subject to any disclaimer, the term ofthis patent is extended or adjusted under 35 U.S.C. 154(b) by 278 days. 

(21) Appl. No.: 12/858,096 

(22) Filed: Aug.17, 2010 

## (65) Prior Publication Data 

US 2012/0046424 Al Feb.23,2012 

(51) Int. Cl. 

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(52) U.S. Cl. CPC .............. C0SG 14110 (2013.01); C0SG 591623 (2013.01); C0SG 59/68 (2013.01); C0SL 61/34 (2013.01) 

(58) Field of Classification Search CPC ....................................................... C08G 14/10 USPC .......................................................... 525/523 See application file for complete search history. 

## (56) References Cited 

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## U.S. PATENT DOCUMENTS 

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# (IO) Patent No.: US 9,249,251 B2 

# Feb.2,2016 (45) Date of Patent: 

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Shieh, J.-Y. and Wang, C.-S., Synthesis of Novel Flame Retardant Epoxy Hardeners and Properties of Cured Products, Polymer., 2001, pp. 7617-7625, No. 52, Elsevier Science Ltd. 

Subrayan, Ramachandran et al., Condensation of Substituted Phenols with Hexakis(methoxymethyl) melamine ... Chem. Mater., 1998, pp. 3506-3512, vol. 10, No. 11, American Chemical Society. Braun D. et al., "Gemeinsame Kondensation von Phenol, Melamin, und Formaldehyd. I. Modellreaktionen", Angewandte Makromolekulare Chemie., 1982, pp. 141-159, vol. 108, No. 1, WileyVCH, Weinheim, D.E. 

Maciejewski, M. et al., "Highly Branched Melamine-Phenolic Novolaks", Polymer Bulletin, 2001, pp. 251-259, vol. 48, No. 3, Springer, Heidelberg, DE. 

* cited by examiner 

Primary Examiner - David Karst 

## (57) ABSTRACT 

Compositions and methods for forming condensates and resin compositions are provided. In one embodiment, a con› densate is formed from a reaction mixture including a triazine monomer, an arylhydroxy monomer, an aldehyde monomer and an acid catalyst having a pKa value of greater than 3.8. The condensates contain up to 28 wt. % of nitrogen and have a melt viscosity of 3,000 cps or less at 175° C. The conden› sates may have a solubility of at least 80 wt. % solids dis› solved in an organic solvent for 120 hours or greater. Also disclosed are methods for the manufacture of the condensate as well as the condensate’s use in fire-retardant epoxy resin compositions suitable for the manufacture of laminates for electronic applications. There is also disclosed a glycidylated triazine-arylhydroxy-aldehyde condensate of this invention. 

US009249251B2 

## FOREIGN PATENT DOCUMENTS 

## OTHER PUBLICATIONS 

## 24 Claims, No Drawings 

