IP Library Granted Patent US 12,162,988
Granted Patent B2
US 12,162,988 · App. 17/374,354 · Granted Dec 10, 2024

Polyaminoboranes

Inventors: Gilles Alcaraz (Rennes, FR); Carlos Antonio De Albuquerque Pinheiro (Vielha, ES); Claire Roiland (Rennes, FR)
Assignees: CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE—CNRS; UNIVERSITE DE RENNES
C08G79/08C04B35/583
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Quick Facts
Patent No.
US 12,162,988
App. No.
17/374,354
Granted
Dec 10, 2024
Kind
B2
Abstract

A process for preparing a polyaminoborane comprising reacting at least one monomer with an aminoborane, wherein the at least one monomer is selected from the group consisting of ammonia, a primary amine and a substituted or unsubstituted hydrazine; and wherein the aminoborane comprises a borane substituted by a secondary amino group; polyaminoboranes obtainable by said process; use of said polyaminoboranes for the preparation of a ceramic precursor or a ceramic, the production of boron nitride, or the storage and/or production of dihydrogen; ceramic precursors, ceramics, hydrogen cells or energy materials comprising said polyaminoboranes.

Claims (31)

1. A polyaminoborane comprising at least one repeating unit of formula R 5 NH—BR 3 R 4 , wherein R 3 and R 4 are the same or different and are selected from the group consisting of a hydrogen atom, a substituted or unsubstituted heteroatom and a linear, branched, cyclic or cyclic and branched organic group having from 1 to 30 carbon atoms; or R 3 and R 4 together form a cyclic or cyclic and branched organic group having from 3 to 30 carbon atoms; wherein R 5 is selected from the group consisting of a hydrogen atom, a substituted or unsubstituted nitrogen atom and a linear, branched, cyclic or cyclic and branched organic group having from 1 to 30 carbon atoms;

wherein if R 5 is a hydrogen atom or a methyl group, at least one of R 3 and R 4 is not a hydrogen atom; and

wherein if R 5 is a n-butyl group, at least one of R 3 and R 4 is not a hydrogen atom, or the polyaminoborane has a mass average molecular weight greater than or equal to 500,000; and

wherein the polyaminoborane has at least one of the following formulas:

[R 5 NH—BR 3 R 4 ] n , wherein n is a number greater than 10; and

[R 5 NH—BR 3 R 4 ] m [R 6 NH—BR 3 R 4 ] (n-m) , wherein n is a number greater than 10 and m is a number greater than or equal to 10 and less than n; wherein R 6 is different from R 5 and R 6 is selected from the group consisting of a hydrogen atom, a substituted or unsubstituted nitrogen atom and a linear, branched, cyclic or cyclic and branched organic group having from 1 to 30 carbon atoms; and wherein if R 5 is methyl, at least one of R 3 and R 4 is not a hydrogen atom, or R 6 is not a hydrogen atom or a n-butyl group; and

wherein at least one of R 3 and R 4 is a hydrogen atom.

2. The polyaminoborane according to claim 1 , wherein at least one of R 5 and R 6 is selected from the group consisting of a hydrogen atom, a substituted or unsubstituted nitrogen atom, methyl, ethyl, n-propyl, n-butyl, substituted or unsubstituted allyl, a substituted or unsubstituted propargyl and a linear, branched, cyclic or cyclic and branched organic group having from 3 to 24 carbon atoms and substituted with at least one alkene, alkyne, ether, thioether, secondary amine, phosphine and/or silyl group.

3. A ceramic precursor or ceramic comprising a polyaminoborane comprising at least one repeating unit of formula R 5 NH—BR 3 R 4 , wherein R 3 and R 4 are the same or different and are selected from the group consisting of a hydrogen atom, a substituted or unsubstituted heteroatom and a linear, branched, cyclic or cyclic and branched organic group having from 1 to 30 carbon atoms; or R 3 and R 4 together form a cyclic or cyclic and branched organic group having from 3 to 30 carbon atoms; wherein R 5 is selected from the group consisting of a hydrogen atom, a substituted or unsubstituted nitrogen atom and a linear, branched, cyclic or cyclic and branched organic group having from 1 to 30 carbon atoms

wherein if R 5 is a dydrogen atom or a methyl group, at least one of R 3 and R 4 is not a hydrogen atom; and

wherein if R 5 is a n-butyl group, at least one of R 3 and R 4 is not a hydrogen atom, or the polyaminoborane has a mass average molecular weight greater than or equal to 500,000; and

wherein the polyaminoborane has at least one of the following formulas:

]R 5 NH—BR 3 R 4 ] n , wherein n is a number greater than 10; and

]R 5 NH—BR 3 R 4 ] m [R 6 NH—BR 3 R 4 ] (n-m) , wherein n is a number greater than 10 and m is a number greater than or equal to 10 and less than n; wherein R 6 is different from R 5 and R 6 is selected from the group consisting of a hydrogen atom, a substituted or unsubstituted nitrogen atom and a linear, branched, byclic or cyclic and branched organic group having from 1 to 30 carbon atoms; and wherein if R 5 is methyl, at least one of R 3 and R 4 is not a hydrogen atom, or R 6 is not a hydrogen atom or a n-butyl group.

4. A hydrogen fuel cell or energy material comprising a polyaminoborane comprising at least one repeating unit of formula R 5 NH—BR 3 R 4 , wherein R 3 and R 4 are the same or different and are selected from the group consisting of a hydrogen atom, a substituted or unsubstituted heteroatom and a linear, branched, cyclic or cyclic and branched organic group having from 1 to 30 carbon atoms; or R 3 and R 4 together form a cyclic or cyclic and branched organic group having from 3 to 30 carbon atoms; wherein R 5 is selected from the group consisting of a hydrogen atom, a substituted or unsubstituted nitrogen atom and a linear, branched, cyclic or cyclic and branched organic group having from 1 to 30 carbon atoms

wherein if R 5 is a hydrogen atom or a methyl group, at least one of R 3 and R 4 is not a hydrogen atom; and

wherein if R 5 is a n-butyl group, at least one of R 3 and R 4 is not a hydrogen atom, or the polyaminoborane has a mass average molecular weight greater than or equal to 500,000; and

wherein the polyaminoborane has at least one of the following formulas:

[R 5 NH—BR 3 R 4 ] n , wherein n is a number greter than 10; and

[R 5 NH—BR 3 R 4 ] m [R 6 NH—BR 3 R 4 ] (n-m) , wherein n is a number greater than 10 and m is a number greater than or equal to 10 and less than n; wherein R 6 is different from R 5 and R 6 is selected from the group consisting of a hydrogen atom, a substituted or unsubstituted nitrogen atom and a linear, branched, cyclic or cyclic and branched organic group having from 1 to 30 carbon atoms; and wherein if R 5 is methyl, at least one of R 3 and R 4 is not a hydrogen atom, or R 6 is not a hydrogen atom or a n-butyl group.

5. The polyaminoborane of claim 1 , wherein at least one of R 5 and R 6 is selected from the group consisting of a hydrogen atom, a substituted or unsubstituted nitrogen atom, methyl, ethyl, n-propyl, n-butyl, substituted or unsubstituted allyl, a substituted or unsubstituted propargyl and a linear, branched, cyclic or cyclic and branched organic group having from 3 to 24 carbon atoms and substituted with at least one alkene, alkyne, ether, thioether, secondary amine, phosphine and/or silyl group.

6. A method comprising:

preparing a ceramic precursor or a ceramic, or

preparing boron nitride, or

storing and/or producing dihydrogen,

from a polyaminoborane comprising at least one repeating unit of formula R 5 NH—BR 3 R 4 , wherein R 3 and R 4 are the same or different and are selected from the group consisting of a hydrogen atom, a substituted or unsubstituted heteroatom and a linear, branched, cyclic or cyclic and branched organic group having from 1 to 30 carbon atoms; or R 3 and R 4 together form a cyclic or cyclic and branched organic group having from 3 to 30 carbon atoms; wherein R 5 is selected from the group consisting of a hydrogen atom, a substituted or unsubstituted nitrogen atom and a linear, branched, cyclic or cyclic and branched organic group having from 1 to 30 carbon atoms

wherein if R 5 is a hydrogen atom or a methyl group, at least one of R 3 and R 4 is not a hydrogen atom; and

wherein if R 5 is a n-butyl group, at least one of R 3 and R 4 is not a hydrogen atom, or the polyaminoborane has a mass average molecular weight greater than or equal to 500,000; and

wherein the polyaminoborane has at least one of the following formulas:

[R 5 NH—BR 3 R 4 ] n , wherein n is a number greater than 10; and

[R 5 NH—BR 3 R 4 ] m [R 6NH—BR 3 R 4 ] (n-m) , wherein n is a number greater than 10 and m is a number greater than or equal to 10 and less than n; wherein R 6 is different from R 5 and R 6 is selected from the group consisting of a hydrogen atom, a substituted or unsubstituted nitrogen atom and a linear, branched, cyclic or cyclic and branched organic group having from 1 to 30 carbon atoms; and wherein if R 5 is methyl, at least one of R 3 and R 4 is not a hydrogen atom, or R 6 is not a hydrogen atom or a n-butyl group.

Assignments (1)
MERGER Recorded Oct 19, 2023
From: UNIVERSITE DE RENNES I
To: UNIVERSITE DE RENNES
Reel/Frame 065490/0667 →
Priority Claims (1)
FR 1750723 · Jan 30, 2017 · national
Continuity (2)
Division 16481749
Related Publication 20210340331A1 · Nov 4, 2021