US 12,215,088 B2
Method for the industrial production of 2-halo-4,6-dialkoxy-1,3,5-triazines and their use in the presence of amines
Valentina Beghetto, Mestre (IT)
Assigned to CROSSING SRL, Treviso (IT)
Filed by CROSSING SRL, Treviso (IT)
Filed on Jul. 22, 2021, as Appl. No. 17/382,591.
Application 17/382,591 is a division of application No. 15/535,992, granted, now 11,111,221, previously published as PCT/IB2015/059892, filed on Dec. 22, 2015.
Claims priority of application No. VE2014A000070 (IT), filed on Dec. 23, 2014; and application No. VE2014A000071 (IT), filed on Dec. 23, 2014.
Prior Publication US 2021/0355091 A1, Nov. 18, 2021
Int. Cl. C07B 43/04 (2006.01); C07B 53/00 (2006.01); C07D 251/26 (2006.01); C07D 251/46 (2006.01); C08J 3/24 (2006.01); C14C 3/26 (2006.01)
CPC C07D 251/26 (2013.01) [C07B 43/04 (2013.01); C07B 53/00 (2013.01); C07D 251/46 (2013.01); C08J 3/24 (2013.01); C14C 3/26 (2013.01); C08J 2301/28 (2013.01); C08J 2389/00 (2013.01)] 12 Claims
 
1. A method for stabilization of collagen matrices and for condensation of natural and synthetic polymers, comprising performing a single-step reaction with a pair of reagents,
wherein a first reagent (Reagent 1) is a composition comprising:
a) at least one or more 2-halo-4,6-dialkoxy-1,3,5-triazines of formula III:

OG Complex Work Unit Chemistry
wherein:
R1 and R2 are independently —CH3, —CH2CH3, —CH(CH3)2, —(CH2)2CH3, or —(CH2)3CH3; and X is Cl− or Br−;
b) a buffer selected from the group consisting of MES, ACES, BES, POPSO, TRIS, HEPPSO, TAPS and Tris-NaCitrate;
c) an inorganic salt of formula X+Y−, wherein X+is selected from the group consisting of Na+, K+, and Ag+, and Y− is selected from the group consisting of ClO4−, BF4−, and Cl−; and
d) a solvent selected from the group consisting of aliphatic ether, alcohol, water, acetone and THF, and
a second reagent (Reagent 2) is a composition comprising:
a) a tertiary amine selected from the group consisting of TMA(trimethylamine), TEA (triethylamine), DEMA(diethylmethylamine), NMM(N-methylmorpholine), NEM(N-ethylmorpholine), MPD(methylpyrrolidine), and MP(methylpiperidine), and/or a quaternary salt thereof;
b) a buffer selected from the group consisting of BES, MOPS, TRIS, POPSO, TAPS and Tris-NaCitrate; and
c) a solvent selected from the group consisting of aliphatic ether, alcohol, water, acetone and THF.