US009249251B2

(12) United States Patent
Viswanathan et al.

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

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

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

6,605,354 B1	8/2003	Gerber
7,411,013 B2*	8/2008	Harashina et al.	524/117
2002/0058735 A1	5/2002	Galbo et al.
2003/0148109 A1	8/2003	Timberlake et al.
2003/0224176 A1	12/2003	Gerber
2005/0003202 A1	1/2005	Gerber
2008/0241578 A1*	10/2008	Lin et al.	428/626
2009/0054614 A1	2/2009	Eguchi et al.

(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 of this 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 A1 Feb. 23, 2012

(51) Int. Cl.

C08G 14/10	(2006.01)
C08G 73/06	(2006.01)
C08L 61/00	(2006.01)
C08L 61/06	(2006.01)
C08L 63/00	(2006.01)
C08L 61/34	(2006.01)
C08G 59/62	(2006.01)
C08G 59/68	(2006.01)

(52) U.S. Cl.

CPC	C08G 14/10 (2013.01); C08G 59/623
	(2013.01); C08G 59/68 (2013.01); C08L 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

U.S. PATENT DOCUMENTS

3,293,212 A	12/1966	Power et al.
3,321,551 A	5/1967	Knutsson
3,364,167 A	1/1968	Imai et al.
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4,268,683 A*	5/1981	Gurgiolo	560/24
5,034,527 A	7/1991	Brown et al.
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6,558,797 B1*	5/2003	Arata et al.	428/418

FOREIGN PATENT DOCUMENTS

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OTHER PUBLICATIONS

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, uad Formaldehyd. I. Modellreaktionen", Angewandte Makromolekulare Chemie, 1982, pp. 141-159, vol. 108, No. 1, Wiley VCH, 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 condensate is formed from a reaction mixture including a triazine monomer, an arylhydroxy monomer, an aldehyde monomer and an acid catalyst having a $pK\_a$ 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 $^\backslash circ$ C. The condensates may have a solubility of at least 80 wt.% solids dissolved 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.

24 Claims, No Drawings