IP Library Granted Patent US 12673917
Granted Patent B2
US 12673917 · App. 18/259,365 · Granted Jul 7, 2026

Bisphenols bearing pendant clickable norbornenyl group and polymers therefrom

Inventors: Deepak Mannusing Maher (Pune, IN); Samadhan Suresh Nagane (Pune, IN); Prakash Purushottam Wadgaonkar (Pune, IN)
Assignee: COUNCIL OF SCIENTIFIC & INDUSTRIAL RESEARCH
C07D209/46C08G63/6856C08G63/81
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Quick Facts
Patent No.
US 12673917
App. No.
18/259,365
Granted
Jul 7, 2026
Kind
B2
Abstract

The present invention relates to a new bisphenol bearing pendant clickable norbornenyl group of formula (I) and its aromatic polyesters bearing pendant norbornenyl groups of formula (II) and processes for the preparation thereof.

Claims (14)

1 . A new bisphenol bearing pendant clickable norbornenyl group of formula (I) below:

wherein, R 1 and R 2 are selected from a group comprising of H, C 1 -C 5 substituted or unsubstituted, straight or branched alkyl, alkoxy; p and q are selected form a group comprising of H and F; m=0 or 1; n=0-6.

2 . A process for the preparation of a new bisphenol bearing pendant clickable norbornenyl group of formula (I) as claimed in claim 1 , wherein said process comprises of stirring the reaction mixture comprising of primary alkyl amine possessing norbornenyl group, compound (2), and phenolphthalein derivative, compound (1), in a molar ratio ranging between 10:1 to 25:1 for a period in a range of 30 to 60 hours at a temperature in a range of 120° C. to 160° C. to afford bisphenol of formula (I);

wherein, R 1 and R 2 are selected from the group comprising of H, C 1 -C 5 substituted or unsubstituted, straight or branched alkyl, alkoxy; p and q are selected form the group comprising of H and F; m=0 or 1; n=0-6.

3 . An aromatic polyester bearing pendant norbornenyl groups of formula (II) from the bisphenol bearing pendant clickable norbornenyl group of formula (I) as claimed in claim 1 ;

wherein, R 1 and R 2 are selected from a group comprising of H, C 1 -C 5 substituted or unsubstituted, straight or branched alkyl, alkoxy; p and q are selected form a group comprising of H and F; 5 m=0 or 1; n=0-6; wherein, x=0.1-1, and y=0-0.9; Ar=isophthaloyl chloride, terephthaloyl chloride, or mixtures thereof.

4 . A process for the preparation of polyester of formula (II) as claimed in claim 3 , wherein said process comprises the steps of:

a) dissolving monomer of formula (I) and bisphenol A in an alkali solution and stirring the reaction mixture;

b) adding benzyltriethylammonium chloride to the reaction mixture of step (a) and stirring followed by addition of a solution of diacid chloride in dichloromethane to the reaction mixture and stirring vigorously; and

c) pouring the reaction mixture of step (b) into hot water; filtering the precipitated polymer and washing it several times with water followed by work-up to afford polyester of formula (II);

wherein, R 1 and R 2 are selected from the group comprising of H, C 1 -C 5 substituted or unsubstituted, straight or branched alkyl, alkoxy; p and q are selected form the group comprising of H and F; m=0 or 1; n=0-6; wherein, x=0.1-1, and y=0-0.9; Ar=isophthaloyl chloride, terephthaloyl chloride, or mixtures thereof.

5 . The process as claimed in claim 4 , wherein said diacid chloride is selected from isophthaloyl chloride, terephthaloyl chloride, or mixtures thereof.

6 . The aromatic polyester bearing pendant norbornenyl groups of formula (II) as claimed in claim 3 , wherein said polymer is cross-linked thermally or photochemically.

7 . The aromatic polyester bearing pendant norbornenyl groups of formula (II) as claimed in claim 3 , wherein said polymer are capable of undergoing tetrazine-norbornene inverse electron demand Diels-Alder reaction, photoinitiated thiol-norbornene reaction or metal-free azide-norbornene 1,3-dipolar cycloaddition click reaction to form modified polymers.