US 2014/0231702 A1 · Cobalt Containing Hydrosilylation Catalysts and Compositions Containing the Catalysts

(1) combining ingredients comprising a Co precursor and a ligand, thereby preparing a reaction product, where one of Conditions (I) and (II) is satisfied, where

Condition (I) is that

the Co precursor has formula (i) Co-A2, where each A is independently a halogen atom, and

the ligand is one of general formulae (ii), (iv), (v), (vi), (vii) (viii), (xi), (xii), (xiii), or (xvii);

where

general formula (ii) is

where subscript x is an integer from 0 to 1 depending on the valency of Q1, Q1 is selected from oxygen, sulphur, nitrogen and phosphorus, A2, A3, A4, A5, and A6 are each independently selected from a monovalent organic group, hydrogen, a halogen atom, and an inorganic heteroatom containing group, each A1 is independently selected from a monovalent organic group, hydrogen, a halogen atom, and an inorganic heteroatom containing group with the proviso that when A6 is Me, then A1 is not a phenylthiophenylether, with the proviso that A2 and A3 may bond together to form a ring structure, with the proviso that A3 and A4 may bond together to form a ring structure, with the proviso that A4 and A5 may bond together to form a ring structure, with the proviso that A5 and A6 may bond together to form a ring structure;

or

general formula (iv) is

where subscript x is an integer from 0 to 1, Q3 is selected from N, O, and S, A15, A16, A17, A18, A20, and A21 are each independently selected from a monovalent organic group, hydrogen, a halogen atom, and an inorganic heteroatom containing group, with the proviso that A15 does not contain methylphenol, and with the proviso that when Q3 is nitrogen then A20 and A21 may not contain an ethyl amine group where the ethyl amine is a tertiary amine, each A19 is independently selected from a monovalent organic group, hydrogen, a halogen atom, and an inorganic heteroatom containing group, with the proviso that A19 does not contain diphenylphosphine, with the proviso that A20 and A21 can be bonded together to form a ring structure, with the proviso that A19 and A18 can be bonded together to form a ring structure, with the proviso that A18 and A17 can be bonded together to form a ring structure, with the proviso that A17 and A16 can be bonded together to form a ring structure, with the proviso that A16 and A15 can be bonded together to form a ring structure;

general formula (v) is

where subscript x is an integer from 0 to 1, subscript y is an integer from 0 to 1, a dashed line represents a single or double bond, Q4 and Q5 are each independently selected from N, O, P, and S, A25, A26, A27, A28, A29, A30, A31, and A32 are each independently selected from a monovalent organic group, hydrogen, a halogen atom, and an inorganic heteroatom containing group, with the proviso that A29 and A31 may not be dimethylpyridine, with the proviso that A29 and A25 may be bonded together to form a ring structure, with the proviso that A25 and A26 may be bonded together to form a ring structure, with the proviso that A26 and A27 may be bonded together to form a ring structure, with the proviso that A27 and A28 may be bonded together to form a ring structure, with the proviso that A28 and A32 may be bonded together to form a ring structure, with the proviso that A29 and A30 may be bonded together to form a ring structure, with the proviso that the ring structure formed by A29 and A30 is not pyrrole, and with the proviso that A31 and A32 may be bonded together to form a ring structure, with the proviso that the ring structure formed by A31 and A32 is not pyrrole;

general formula (vi) is

where subscript x is an integer from 0 to 1, Q8 is selected from oxygen, sulphur nitrogen and phosphorus, A45, A46, A47, A49, A50, and A51 are each independently selected from a monovalent organic group, hydrogen, a halogen atom, and an inorganic heteroatom containing group, with the proviso that when Q8 is sulphur then A45 is not phenyl, A48 and A52 are each independently selected from a monovalent organic group, hydrogen, and an inorganic heteroatom containing group, with the provisos that A45 and A52 may combine to form a ring structure, A52 and A51 may combine to form a ring structure, A51 and A50 may combine to form a ring structure, A50 and A49 may combine to form a ring structure, A45 and A46 may combine to form a ring structure;

or

general formula (vii) is

where subscript x is an integer from 0 to 1, Q10 is selected from oxygen, sulphur nitrogen and phosphorus. A dashed line indicates single or double bond, A56 and A57 are each independently selected from a monovalent organic group, hydrogen, a halogen atom, and an inorganic heteroatom containing group, A58 and A55 are each independently selected from a monovalent organic group, hydrogen, and an inorganic heteroatom containing group, with the provisos that A56 and A57 may combine to form a ring structure, A55 and A56 may combine to form a ring structure;

or

general formula (viii)

where subscript x is an integer from 0 to 1, subscript y is an integer from 0 to 1, Q11 and Q12 are each independently selected from N, O, and S, with the proviso that if Q11 and/or Q12 are nitrogen then they are not imine nitrogen, dashed lines represent either single or double bonds, A60, A61, A65, and A66 are each independently selected from a monovalent organic group, hydrogen, a halogen atom, and an inorganic heteroatom containing group, each A62, each A63, and each A64 are independently selected from a monovalent organic group, hydrogen, halogen atom, and an inorganic heteroatom containing group, with the provisos that A60 and A61 may be bonded together to form a ring structure, A61 and A62 may be bonded together to form a ring structure, A62 and A63 may be bonded together to form a ring structure, A63 and A64 may be bonded together to form a ring structure, A64 and A65 may be bonded together to form a ring structure, A65 and A66 may be bonded together to form a ring structure, A63 and A61 may be bonded together to form a ring structure, with the proviso that when Q11 is S, then Q11 is the only heteroatom in the ring;

or

general formula (xi) is

where subscript x is an integer from 0 to 2, subscripts y and z are each independently an integer from 0 to 1, dashed lines indicate single or double bonds, the two nitrogen atoms may be positively charged with a balancing negatively charged anion, Q50 is selected from N and C, and A86 and A89 are each independently selected from a monovalent organic group, hydrogen, or an inorganic heteroatom containing group, the proviso that A86 does not contain pentylamine, A87 A88, A90, and A91 are each independently selected from a monovalent organic group, hydrogen, and an inorganic heteroatom containing group with the proviso that A87 A88, A90, and A91 do not contain a dithio acid, and with the proviso that A87 and A91 are not isopropyl or tertiary butyl;

and with the provisos that A88 and A90 may be bonded together to form a ring structure, A87 and A88 may be bonded together to form a ring structure, A87 and A86 may be bonded together to form a ring structure, A86 and A91 may be bonded together to form a ring structure, A91 and A90 may be bonded together to form a ring structure;

or

general formula (xii) is

subscript x is an integer from 1 to 5, Q20 is selected from nitrogen and phosphorus, dashed lines indicate a single or double bond, A90, A91, A92, A93 A94, and A95 are each independently selected from a monovalent organic group, hydrogen, a halogen, or an inorganic heteroatom containing group with the proviso that when Q20 is nitrogen then A90, A91, A92, A93 A94, and A95 are not halogen with the proviso that A90 and A91 are not di(tert-butyl)phenol;

and with the provisos that A90 and A91 may be bonded together to form a ring structure, with the proviso that when A90 and A91 bond together to form a phosphalane ring structure, then the ligand of general formula (xii) is aliphatic;

A91 and A92 may be bonded together to form a ring structure;

A92 and A93 may be bonded together to form a ring structure, with the proviso that when Q20 is P, then the ring structure is not a benzodioxole;

A93 and A94 may be bonded together to form a ring structure, with the proviso that when A93 and A94 form a ring structure and Q20 is nitrogen then there are no other hetero-atoms in the ring structure with Q20;

A94 and A95 may be bonded together to form a ring structure;

when subscript x is 2 or more, then two or more instances of A93 may bond together to form a ring structure;

or

general formula (xiii) is

where subscript x is an integer from 0 to 1, Q21 is selected from oxygen, sulphur, nitrogen and phosphorus, A96, A97, A98, A99, A100, A101, A102, A103, A104, A105, A106, A107, and A108 are each independently selected from a monovalent organic group, hydrogen, a halogen, and an inorganic heteroatom containing group;

with the provisos that A96 and A97 may bond together to form a ring structure;

A99 and A100 may bond together to form a ring structure;

A96 and A108 may bond together to form a ring structure;

A108 and A107 may bond together to form a ring structure;

A107 and A106 may bond together to form a ring structure;

A106 and A105 may bond together to form a ring structure;

A105 and A104 may bond together to form a ring structure with the proviso that the bridging group is dimethyl carbon then A96, A97, A99, and A100 are not Ph;

A104 and A103 may bond together to form a ring structure;

A103 and A102 may bond together to form a ring structure;

A102 and A101 may bond together to form a ring structure;

or

general formula (xvii) is

where Q26 is selected from oxygen and sulphur, Q27 is selected from nitrogen and carbon, subscript x is an integer from 0 to 4, A125, A126, A127, and A128, are each independently selected from a monovalent organic group, hydrogen, a halogen atom, and an inorganic heteroatom containing group, each A130 is independently selected from a monovalent organic group, a halogen atom, and an inorganic heteroatom containing group, with the proviso that A130 is not diphenylphosphine, A129 is selected from a monovalent organic group, hydrogen, and an inorganic heteroatom containing group, with the proviso that A128 and A129 may combine to form a ring structure;

or

Condition (II) is that

the Co precursor has formula (i) Co-A2, where each A is independently a monovalent organic group, and

the ligand is one of general formulae (ii), (iii), (v), (vi), (vii), (viii), (ix), (xi), (xii), (xiii), (xvi), or (xviii);

where

general formula (ii) is

where subscript x is an integer from 0 to 1 depending on the valency of Q1, Q1 is selected from oxygen, sulphur, nitrogen and phosphorus, A2, A3, A4, A5, and A6 are each independently selected from a monovalent organic group, hydrogen, a halogen atom, and an inorganic heteroatom containing group, each A1 is independently selected from a monovalent organic group, hydrogen, a halogen atom, and an inorganic heteroatom containing group with the proviso that when A6 is Me, then A1 is not a phenylthiophenylether, with the proviso that A2 and A3 may bond together to form a ring structure, with the proviso that A3 and A4 may bond together to form a ring structure, with the proviso that A4 and A5 may bond together to form a ring structure, with the proviso that A5 and A6 may bond together to form a ring structure;

or

general formula (iii) is

where Q2 is oxygen or sulphur, A7, A8, A9, A10, and A12 are each independently selected from a monovalent organic group, hydrogen, a halogen atom, and an inorganic heteroatom containing group, A11 is selected from a monovalent organic group, hydrogen, a halogen atom, and a monovalent inorganic heteroatom containing group, with the proviso that A11 is not phenyl, and with the proviso that when Q2 is S, then A11 is not tBu;

and with the provisos that A7 and A8 may combine to form a ring structure;

A8 and A9 may combine to form a ring structure;

A9 and A10 may combine to form a ring structure;

A12 and A11 may combine to form a ring structure;

or

general formula (v) is

where subscript x is an integer from 0 to 1, subscript y is an integer from 0 to 1, a dashed line represents a single or double bond, Q4 and Q5 are each independently selected from N, O, P, and S, A25, A26, A27, A28, A29, A30, A31, and A32 are each independently selected from a monovalent organic group, hydrogen, a halogen atom, and an inorganic heteroatom containing group, with the proviso that A29 and A31 may not be dimethylpyridine, with the proviso that A29 and A25 may be bonded together to form a ring structure, with the proviso that A25 and A26 may be bonded together to form a ring structure, with the proviso that A26 and A27 may be bonded together to form a ring structure, with the proviso that A27 and A28 may be bonded together to form a ring structure, with the proviso that A28 and A32 may be bonded together to form a ring structure, with the proviso that A29 and A30 may be bonded together to form a ring structure, with the proviso that the ring structure formed by A29 and A30 is not pyrrole, and with the proviso that A31 and A32 may be bonded together to form a ring structure, with the proviso that the ring structure formed by A31 and A32 is not pyrrole;

general formula (vi) is

where subscript x is an integer from 0 to 1, Q8 is selected from oxygen, sulphur nitrogen and phosphorus, A45, A46, A47, A49, A50, and A51 are each independently selected from a monovalent organic group, hydrogen, a halogen atom, and an inorganic heteroatom containing group, with the proviso that when Q8 is sulphur then A45 is not phenyl, A48 and A52 are each independently selected from a monovalent organic group, hydrogen, and an inorganic heteroatom containing group, with the provisos that A45 and A52 may combine to form a ring structure, A52 and A51 may combine to form a ring structure, A51 and A50 may combine to form a ring structure, A50 and A49 may combine to form a ring structure, A45 and A46 may combine to form a ring structure;

or

general formula (vii) is

where subscript x is an integer from 0 to 1, Q10 is selected from oxygen, sulphur nitrogen and phosphorus. A dashed line indicates single or double bond, A56 and A57 are each independently selected from a monovalent organic group, hydrogen, a halogen atom, and an inorganic heteroatom containing group, A58 and A55 are each independently selected from a monovalent organic group, hydrogen, and an inorganic heteroatom containing group, with the provisos that A56 and A57 may combine to form a ring structure, A55 and A56 may combine to form a ring structure;

or

general formula (viii)

where subscript x is an integer from 0 to 1, subscript y is an integer from 0 to 1, Q11 and Q12 are each independently selected from N, O, and S, with the proviso that if Q11 and/or Q12 are nitrogen then they are not imine nitrogen, dashed lines represent either single or double bonds, A60, A61, A65, and A66 are each independently selected from a monovalent organic group, hydrogen, a halogen atom, and an inorganic heteroatom containing group, each A62, each A63, and each A64 are independently selected from a monovalent organic group, hydrogen, halogen atom, and an inorganic heteroatom containing group, with the provisos that A60 and A61 may be bonded together to form a ring structure, A61 and A62 may be bonded together to form a ring structure, A62 and A63 may be bonded together to form a ring structure, A63 and A64 may be bonded together to form a ring structure, A64 and A65 may be bonded together to form a ring structure, A65 and A66 may be bonded together to form a ring structure, A63 and A61 may be bonded together to form a ring structure, with the proviso that when Q11 is S, then Q11 is the only heteroatom in the ring;

or

general formula (ix) is

where subscript x is an integer from 0 to 1, Q17 is selected from oxygen, sulphur, nitrogen, phosphorus and carbon, with the proviso that when Q17 is carbon, the carbon forms a carbonyl bond with A81 and a hydroxyl group with A80, Q18 is selected from oxygen and sulphur, Q19 is selected from hydroxyl and thiol, A82, A83, A84, and A85 are each independently selected from a monovalent organic group, hydrogen, a halogen atom, and an inorganic heteroatom containing group, A80 and A81 are each independently selected from a monovalent organic group, and an inorganic heteroatom containing group;

with the provisos that A81 and A82 may bond together to form a ring structure, A82 and A83 may bond together to form a ring structure, A83 and A84 may bond together to form a ring structure, A84 and A85 may bond together to form a ring structure;

or

general formula (xi) is

where subscript x is an integer from 0 to 2, subscripts y and z are each independently an integer from 0 to 1, dashed lines indicate single or double bonds, the two nitrogen atoms may be positively charged with a balancing negatively charged anion, Q50 is selected from N and C, and A86 and A89 are each independently selected from a monovalent organic group, hydrogen, or an inorganic heteroatom containing group, the proviso that A86 does not contain pentylamine, A87 A88, A90, and A91 are each independently selected from a monovalent organic group, hydrogen, and an inorganic heteroatom containing group with the proviso that A87 A88, A90, and A91 do not contain a dithio acid, and with the proviso that A87 and A91 are not isopropyl or tertiary butyl;

and with the provisos that A88 and A90 may be bonded together to form a ring structure, A87 and A88 may be bonded together to form a ring structure, A87 and A86 may be bonded together to form a ring structure, A86 and A91 may be bonded together to form a ring structure, A91 and A90 may be bonded together to form a ring structure;

or

general formula (xii) is

subscript x is an integer from 1 to 5, Q20 is selected from nitrogen and phosphorus, dashed lines indicate a single or double bond, A90, A91, A92, A93 A94, and A95 are each independently selected from a monovalent organic group, hydrogen, a halogen, or an inorganic heteroatom containing group with the proviso that when Q20 is nitrogen then A90, A91, A92, A93 A94, and A95 are not halogen with the proviso that A90 and A91 are not di(tert-butyl)phenol;

and with the provisos that A90 and A91 may be bonded together to form a ring structure, with the proviso that when A90 and A91 bond together to form a phosphalane ring structure, then the ligand of general formula (xii) is aliphatic;

A91 and A92 may be bonded together to form a ring structure;

A92 and A93 may be bonded together to form a ring structure, with the proviso that when Q20 is P, then the ring structure is not a benzodioxole;

A93 and A94 may be bonded together to form a ring structure, with the proviso that when A93 and A94 form a ring structure and Q20 is nitrogen then there are no other hetero-atoms in the ring structure with Q20;

A94 and A95 may be bonded together to form a ring structure;

when subscript x is 2 or more, then two or more instances of A93 may bond together to form a ring structure;

or

general formula (xiii) is

where subscript x is an integer from 0 to 1, Q21 is selected from oxygen, sulphur, nitrogen and phosphorus, A96, A97, A98, A99, A100, A101, A102, A103, A104, A105, A106, A107, and A108 are each independently selected from a monovalent organic group, hydrogen, a halogen, and an inorganic heteroatom containing group;

with the provisos that A96 and A97 may bond together to form a ring structure;

A99 and A100 may bond together to form a ring structure;

A96 and A108 may bond together to form a ring structure;

A108 and A107 may bond together to form a ring structure;

A107 and A106 may bond together to form a ring structure;

A106 and A105 may bond together to form a ring structure;

A105 and A104 may bond together to form a ring structure with the proviso that the bridging group is dimethyl carbon then A96, A97, A99, and A100 are not Ph;

A104 and A103 may bond together to form a ring structure;

A103 and A102 may bond together to form a ring structure;

A102 and A101 may bond together to form a ring structure;

or

general formula (xvi) is

where subscripts x and y are each independently integers from 0 to 4, Q24 and Q25 are each independently selected from oxygen and sulphur;

and each A121 and each A122 are independently selected from a monovalent organic group, hydrogen, and an inorganic heteroatom containing group;

or

general formula (xviii) is

where A132, A133, and A134 are each independently selected from a monovalent organic group, hydrogen, a halogen, and an inorganic heteroatom containing group, and A131 and A135 are independently selected from a monovalent organic group, hydrogen, and an inorganic heteroatom containing group.

Cobalt Containing Hydrosilylation Catalysts and Compositions Containing the Catalysts

Life of this patent

Cobalt Containing Hydrosilylation Catalysts and Compositions Containing the Catalysts

Life of this patent

Abstract

Claims30