Curable silicone-based compositions and applications thereof

A method of making a silicone composition comprising:

• (i) mixing Polymer A, a conductive filler, a catalyst, and Polymer B together to form a mixture, where the catalyst is added with respect to total weight of the polymer A and polymer B, and filler;
• (ii) homogenizing the mixture of (i) to form a homogenized mixture;
• and
• (iii) curing the homogenized mixture by condensation curing,
• wherein polymer A is a silicone polymer of Formula (1) and polymer B is a silicone polymer of Formula (2a) or (2a′):
• (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)
• 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, l, 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):
• 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) or (1q′):
• 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,
• L2, L3, and L4 are independently selected from alkoxy, phthalimide, fluorinated hydrocarbon, hydrocarbon, aromatic hydrocarbon, u, v, w, and x are each 0 or greater,
• K is independently selected from carbon, silicon, heteroatom, hydrocarbon, or carbonyl radical with the proviso that y>0;
• the polymer B is selected from Formula (2a) or (2a′):
• 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):
• 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′):
• 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.

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
• (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)
• 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):
• 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) or (1q′):
• 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,
• L2, L3, and L4 are independently selected from alkoxy, phthalimide, fluorinated hydrocarbon, hydrocarbon, aromatic hydrocarbon, u, v, w, and x are each 0 or greater,
• K is independently selected from carbon, silicon, heteroatom, hydrocarbon, or carbonyl radical with the proviso that y>0;
• the polymer B is selected from Formula (2a) or (2a′):
• 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):
• 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 (c′+d+e′+f+g′+y′″+z′)>0,
• 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′):
• 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.

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
• (iv) a polymer B of Formula (2a) or (2a′) in a range from about 1% to 80% based on the weight of the composition;
• 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)
• 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.