Silane functional stabilizers for extending long-term electrical power cable performance

Patent metadata

Field	Value
Publication number	US-12516079-B2
Application number	US-202418408396-A
Country	US
Kind code	B2
Filing date	Jan 9, 2024
Priority date	Jan 10, 2023
Publication date	Jan 6, 2026
Grant date	Jan 6, 2026

Abstract

Provided are unique acyl metallocene compounds of formula (1): as defined herein. Additionally provided are dielectric enhancement fluids and hydrosilylation gel compositions, in either case comprising at least one acyl metallocene compound of formula (1). Further provided are methods for extending the useful life of an insulated cable, comprising injecting the dielectric enhancement fluids or the hydrosilylation gel compositions into the cable, wherein the acyl metallocene compound of formula (1) diffuses into the polymeric insulation. Yet further provided are methods for extending the useful life of in-service electrical cable, comprising injecting the dielectric enhancement fluid compositions into the cable, wherein the injected composition provides for both initial permeation of the acyl metallocene compound of formula (1) into the polymeric insulation, and extended retention of subsequent condensation products of the acyl metallocene compound of formula (1) in the cable insulation.

First claim

The invention claimed is:

1 . An acyl metallocene compound of formula (1):

wherein:
M is a metal ion selected from Fe(II), Mn(II), Ni(II), Co(II), Ru(II), or Os(II);
m is 1-4, where a silane acyl groups group(s) can be at any position(s) on one or both of the cyclopentadienyl rings;
p can vary from 2 to 20 carbon atoms;
R 1 and R 2 are C 1 -C 4 linear or branched alkyl, or H;
X is a C 1 -C 5 linear or branched alkyl;
Y is C 1 -C 4 acyloxy, C 1 -C 4 alkyloxy, or silyloxy; and
wherein for m=1, n is two or three, and for m=2-4, n is one, two, or three.

2 . The compound of claim 1 , wherein for formula (1): M is Fe(II).

3 . The compound of claim 2 , wherein for formula (1): M is Fe(II); m is 1-2; R1 and R2 are C1-C2 alkyl or H; X is C1-C2 alkyl; and Y is C1-C4 alkyloxy.

4 . The compound of claim 3 , wherein for formula (1): M is Fe(II); m is 1; R1 and R2 are H; X is —CH3; and Y is C1-C2 alkyloxy.

5 . The compound of claim 1 , wherein the compound is selected from the group consisting of:

6 . The compound of claim 5 , wherein the compound is 11-(dimethoxymethylsilyl)-1-oxo-undecyl-1-ferrocene (AcylFc-DMS), or 3-(dimethoxymethylsilyl)-1-oxo-propyl-1-ferrocene.

7 . A dielectric enhancement fluid, comprising:
(a) an acyl metallocene compound of formula (1):

wherein:
M is a metal ion selected from Fe(II), Mn(II), Ni(II), Co(II), Ru(II), or Os(II);
m is 1-4, where a silane acyl group(s) can be at any position(s) on one or both of the cyclopentadienyl rings;
p can vary from 2 to 20 carbon atoms;
R1 and R2 are C1-C4 linear or branched alkyl, or H;
X is a C1-C5 linear or branched alkyl;
Y is C1-C4 acyloxy, C1-C4 alkyloxy, or silyloxy; and
wherein for m=1, n is two or three, and for m=2-4, n is one, two, or three; and
(b) at least one component selected from:
(1) at least one a water-reactive material selected from:
(i) an organosilane monomer having at least two water-reactive groups,
(ii) the organosilane monomer (1) wherein at least one of the water-reactive groups is substituted with a condensable silanol group,
(iii) an oligomer of the above organosilane monomer (I), and/or
(iv) a co-oligomer of the above organosilane monomer (i) with a different organosilane monomer;
(2) a non-water-reactive organic material having a diffusion coefficient of less than about 10-9 cm2/sec and an equilibrium concentration of at least about 0.005 gm/cm3 in a polymeric insulation, the diffusion coefficient and the equilibrium concentration being determined at temperature T;
(3) metallocenes having a metal ion selected from Fe(II), Mn(II), Ni(II), Co(II), Ru(II), or Os(II), sandwiched between two cyclopentadienyl rings, and derivatives thereof;
(4) an organic compound having an equilibrium concentration in the polymeric insulation at 55° C., which is less than 2.25 times the equilibrium concentration at 22° C.;
(5) at least one silane functional additive derived from:
(i) a hindered phenolic antioxidant based on 2,6-di-tert-butyl phenol,
(ii) a hindered amine light stabilizer, based on tetramethyl piperidine, and/or
(iii) a UV absorber or energy quencher selected from benzotriazoles, triazines, benzophenones, and/or nickel chelates; and/or
(6) at least one catalyst suitable to catalyze hydrolysis and condensation of the water reactive materials of (a), (1), and (5).

8 . The dielectric enhancement fluid of claim 7 , wherein the catalyst is a strong acid, or a compound of titanium and/or tin.

9 . The dielectric enhancement fluid of claim 7 , wherein for formula (1): M is Fe(II).

10 . The dielectric enhancement fluid of claim 9 , wherein for formula (1): M is Fe(II); m is 1-2; R1 and R2 are C1-C2 alkyl or H; X is C1-C2 alkyl; and Y is C1-C4 alkyloxy.

11 . The dielectric enhancement fluid of claim 10 , wherein for formula (1): M is Fe(II); m is 1; R1 and R2 are H; X is —CH3; and Y is C1-C2 alkyloxy.

12 . The dielectric enhancement fluid of claim 11 , wherein for formula (1) the compound is selected from the group consisting of:

13 . The dielectric enhancement fluid of claim 12 , wherein the compound is 11-(dimethoxymethylsilyl)-1-oxo-undecyl-1-ferrocene (AcylFc-DMS), or 3-(dimethoxymethylsilyl)-1-oxo-propyl-1-ferrocene.

14 . The dielectric enhancement fluid of claim 7 , wherein for (5), the at least one silane functional additive is selected from:
(i) a hindered phenolic antioxidant of formula (XIX) or (XIXa):

wherein:
S1 and S2 can be equal or different C1-C10 branched alkyl;
m is zero or one;
T is oxygen or sulfur;
A is a C1-C10 linear or branched alkylene, or

wherein S3, S4, and S5 are C3-C10 linear or branched alkylene;
X is a C1-C5 linear or branched alkyl;
Y is hydrogen, halogen, C1-C4 acyloxy, C1-C4 alkyloxy, amino, amino-oxy, or silyloxy; and
n is one, two, or three;
(ii) a hindered amine light stabilizer of formula (XI):

wherein:
m+n is a number from 1 to 40, n varies from zero to 50% of the sum m+n;
A is —O—;
T1 and T4 which can be identical or different are methyl, methoxy, ethoxy, or OH;
T2 is trimethylene or is also a direct bond if A is —O— and T1 and T4 are methyl;
T3 is methyl, C7-C9 alkyl, or cyclohexyl;
T5 is C1-C12 alkyl;
X1 is as defined for T1 or is a group (CH3)3 SiO—; and
X2 is hydrogen, methyl, ethyl, a group (CH3)3 Si— or, if n is zero and T1 and X1 are methyl, X2 is also a group of the formula (XIII)

and, if m+n is a number from 3 to 10, X1 and X2 together can also be a direct bond; and/or
(iii) a UV absorber or energy quencher of formula (IA) or (IIA):

wherein:
G1 and G6 are hydrogen;
G2 and G7 are independently H, cyano, CF3-, fluoro, —CO-G3, or E3SO2-;
G3 is straight or branched chain alkyl of 1 to 24 carbon atoms, straight or branched chain alkenyl of 2 to 18 carbon atoms, cycloalkyl of 5 to 12 carbon atoms, phenylalkyl of 7 to 15 carbon atoms, phenyl, or said phenyl or said phenylalkyl substituted on the phenyl ring by 1 to 4 alkyl of 1 to 4 carbon atoms;
E1 is phenylalkyl of 7 to 15 carbon atoms, phenyl, or said phenyl or said phenylalkyl substituted on the phenyl ring by 1 to 4 alkyl groups of 1 to

Assignees

• Southwire Co Llc

Inventors

• Ravichandran Ramanathan

Classifications

• H01B13/322

  the material being a liquid, jelly-like or viscous substance · CPC title

• H01B3/46 Primary

  silicones · CPC title

• C07F17/02 Primary

  of metals of Groups 8, 9 or 10 of the Periodic Table · CPC title