US 12,479,994 B2
Curable silicone-based compositions and applications thereof
Titash Mondal, Bengal (IN); Murali Mg, Karnataka (IN); Shreedhar Bhat, Bangalore (IN); and Haigang Kang, Shanghai (CN)
Assigned to Momentive Performance Materials Inc., Waterford, NY (US)
Appl. No. 17/417,441
Filed by Momentive Performance Materials Inc., Waterford, NY (US)
PCT Filed Dec. 18, 2019, PCT No. PCT/US2019/067021
§ 371(c)(1), (2) Date Jun. 23, 2021,
PCT Pub. No. WO2020/139642, PCT Pub. Date Jul. 2, 2020.
Prior Publication US 2022/0073746 A1, Mar. 10, 2022
Int. Cl. C08L 83/04 (2006.01); C08G 18/10 (2006.01); C08G 18/24 (2006.01); C08G 18/28 (2006.01); C08G 18/32 (2006.01); C08G 18/38 (2006.01); C08G 18/50 (2006.01); C08G 18/61 (2006.01); C08G 18/71 (2006.01); C08G 77/08 (2006.01); C08G 77/16 (2006.01); C08G 77/24 (2006.01); C08G 77/26 (2006.01); C08K 3/013 (2018.01); C08K 3/04 (2006.01); C08K 3/08 (2006.01); C08K 5/57 (2006.01); C08K 9/02 (2006.01); C08L 75/04 (2006.01); C08L 75/08 (2006.01); C08L 83/08 (2006.01); C08L 83/10 (2006.01); C08L 83/14 (2006.01); C09D 183/14 (2006.01); C08G 65/336 (2006.01); C08G 77/00 (2006.01); C08G 77/04 (2006.01); C08G 77/18 (2006.01); C08G 77/388 (2006.01); C08K 5/5435 (2006.01); C08K 5/544 (2006.01); C08K 5/548 (2006.01)
CPC C08L 83/04 (2013.01) [C08G 18/10 (2013.01); C08G 18/24 (2013.01); C08G 18/2885 (2013.01); C08G 18/3206 (2013.01); C08G 18/3893 (2013.01); C08G 18/5015 (2013.01); C08G 18/61 (2013.01); C08G 18/718 (2013.01); C08G 77/08 (2013.01); C08G 77/16 (2013.01); C08G 77/24 (2013.01); C08G 77/26 (2013.01); C08K 3/013 (2018.01); C08K 3/041 (2017.05); C08K 3/08 (2013.01); C08K 5/57 (2013.01); C08K 9/02 (2013.01); C08L 75/04 (2013.01); C08L 75/08 (2013.01); C08L 83/08 (2013.01); C08L 83/10 (2013.01); C08L 83/14 (2013.01); C09D 183/14 (2013.01); C08G 65/336 (2013.01); C08G 77/04 (2013.01); C08G 77/18 (2013.01); C08G 77/388 (2013.01); C08G 77/70 (2013.01); C08K 3/04 (2013.01); C08K 3/042 (2017.05); C08K 2003/0806 (2013.01); C08K 2003/085 (2013.01); C08K 5/5435 (2013.01); C08K 5/544 (2013.01); C08K 5/548 (2013.01); C08K 2201/001 (2013.01); C08L 2203/20 (2013.01); C08L 2205/025 (2013.01); C08L 2312/08 (2013.01)] 22 Claims
 
1. A curable silicone composition, comprising:
(i) a polymer A of Formula 1;
(ii) a conductive filler in an amount of 5% to 80% by weight of the composition;
(iii) a catalyst, and optionally
(iv) a polymer B of Formula (2a) or (2a′);
wherein the curable silicone composition is a condensation cure system; and the cured form of the curable composition is an electrically conductive material,
(R)a(W)b(R)a″  Formula 1
wherein a and a″ are independently zero or greater with the proviso that a+a″>0 and b is 1, wherein R is represented by Formula (1a):
(CH2)c(CH2O)d(CHOH)e(S)f(X)g  Formula (1a)
S is independently selected from a hydroxyl radical, an isocyanate radical, a primary amine, or a carboxylic radical and X is independently selected from Formula (1b)

OG Complex Work Unit Chemistry
wherein R1, R1′, and R1″ are independently selected from an alkyl radical, an alkoxy radical, a hydroxyl radical, a hydrogen radical or from a hydrocarbon having C1-C20 carbon atoms, or fluorinated hydrocarbon having C1-C20 carbon atoms,
c, d, e, f, and g are each an integer of 0 or greater with the proviso that c+d+e+f+g>0,
W in Formula 1 is represented by Formula (1c)
(Y)n(Z)i  Formula (1c)
wherein h and i are independently zero or greater with the proviso that h+i>0,
Y in formula (1c) is represented by Formula (1d):
(M1)x″(D1)j(D2)k(D*)l(T1)m(Q1)n(M2)y″Formula  (1d)
where in j, k, 1, m, n, x″, and y″ are independently zero or greater with the proviso that (j+k+l+m+n+x″+y″)>0
wherein M1 is represented by Formula (1e):
R2R3R4Sil1/2  Formula (1e)
D1 is represented by Formula (1f):
R5R6Sil2/2  Formula (1f)
D2 is represented by Formula (1g):
R7R8Sil2/2  Formula (1g)
D* is represented by Formula (1h):

OG Complex Work Unit Chemistry
D3 is represented by Formula (1i):
R9R10Sil2/2  Formula (1i)
D4 is represented by Formula (1j):
R11R12Sil2/2  Formula (1j)
D5 is represented by Formula (1k):
R13R14Sil2/2  Formula (1k)
D6 is represented by Formula (1l):
R15R16Sil2/2  Formula (1l)
T1 is represented by Formula (1m):
R17Sil3/2  Formula (1m)
Q1 is represented by Formula (1n):
Sil4/2  Formula (1n)
M2 is represented by Formula (1o):
R18R19R20Sil1/2  Formula (1o)
R2-R20 are independently selected from R, or a monovalent cyclic or acyclic, aliphatic or aromatic, hydrocarbon, or a fluorinated hydrocarbon having 1-20 carbon atoms or carboxylate radical or epoxy radical,
wherein o and p are independently zero or greater with the proviso that o+p>0,
I is O or CH2 group subject to the limitation that the molecule contains an even number of O1/2 and even number of (CH2)1/2,
Z in Formula (1c) is represented by Formula (1p):
[E]q[J]r Formula (1p)
wherein E is independently selected from urethane, urea, anhydride, amide, imide, hydrogen radical, or a monovalent cyclic or acyclic, aliphatic or aromatic, hydrocarbon, or a fluorinated hydrocarbon having 1-20 carbon atoms, q can be 0 or greater, and r>0,
J is independently selected from Formula (1q):

OG Complex Work Unit Chemistry
wherein M is independently selected from a carbon atom or a heteroatom,
G is a heteroatom selected from oxygen,
wherein t and s are independently zero or greater with the proviso that t+s>0,
L1 is independently selected from urethane, urea, anhydride, or amide,
the polymer B is selected from Formula (2a) or (2a′):

OG Complex Work Unit Chemistry
wherein M′ is independently selected from a carbon atom or a heteroatom,
G′ is a heteroatom selected from oxygen,
s′ is 0 or greater,
t′>0,
L1′ is independently selected from an isocyanate, a primary amine, or from R′ represented by Formula (2b):
(M3)y″(D7)c′(D8)d′(D**)e′(T2)f′(Q2)g′(M4)z′  Formula (2b)
wherein M3 is represented by Formula (2c):
R25R26R27Sil′1/2  Formula (2c)
D7 is represented by Formula (2d)
R28R29Sil′2/2  Formula (2d)
D8 is represented by Formula (2e):
R30R31Sil′2/2  Formula (2e)
D** is represented by Formula (2f):

OG Complex Work Unit Chemistry
D9 is represented by Formula (2g):
R32R33Sil′2/2  Formula (2g)
D10 is represented by Formula (2h):
R34R35Sil′2/2  Formula (2h)
D11 is represented by Formula (2i):
R36R37Sil′2/2  Formula (2i)
D12 is represented by Formula (2j):
R38R39Sil′2/2  Formula (2j)
T2 is represented by Formula (2k):
R40Sil′3/2  Formula (2k)
Q2 is represented by Formula (21):
Sil′4/2  Formula (21)
M4 is represented by Formula (2m):
R41R42R43Sil′1/2  Formula (2m)
wherein R25-R43 are independently selected from a hydrogen radical, a monovalent cyclic or acyclic, aliphatic or aromatic, hydrocarbon, or a fluorinated hydrocarbon having C1-C20 carbon atoms, an alkoxy radical, or a hydroxyl radical,
I′is O or a CH2 group subject to the limitation that the molecule contains an even number of O1/2 and even number of (CH2)1/2
c′, d, e′, f, g′, y′″ and z′ are independently zero or greater with the proviso that
h′, i′>0 when e′>0;
L1′ of Formula (2a) is represented by Formula (2n):
(R′)a′(W′)b′(R′)a″  Formula (2n)
wherein R′is represented by Formula (2b) above,
W′ is independently selected from a hydrocarbon radical of 1-20 carbon atom, a fluorinated hydrocarbon, or a perfluroether;
a′ and a″ are each 0 or greater with the proviso that a′+a″>0, and b′ is 0 or greater;
[E′]q′[J′]r′  Formula (2a′)
wherein E′ is independently selected from R′, isocyanate, amine, hydrogen, a monovalent cyclic or acyclic, aliphatic or aromatic, hydrocarbon, or a fluorinated hydrocarbon having C1-C20 carbon atoms, or combinations thereof,
wherein q′ and r′ are independently zero or greater with the proviso that q′+r′>0,
J′ is independently selected from Formula (2b′):

OG Complex Work Unit Chemistry
wherein L2′, L3′, L4′ are independently selected from a L1′, phthalimide radical, a fluorinated hydrocarbon, an aliphatic or aromatic hydrocarbon, a urea linkage, alkoxy, or a urethane linkage, u′, v′, w′, and x′ are each 0 or greater with the proviso that u′+v′+w′+x′>0, K is independently selected from carbon, silicon, a heteroatom, a hydrocarbon radical, or a carbonyl radical with the proviso that y′>0.