Silane functionalized compounds and compositions thereof
Compositions comprising Silane functionalized compounds are provided. In one embodiment, the silane functionalized compounds include an epoxy resin derived backbone having silane functional groups pendant to the backbone or serving as end caps. The compositions comprising silane functionalized compounds may be utilized in a variety of applications including in coating formulations, adhesive formulations, composite materials, and combinations thereof.
1. A composition comprising
(a) a silane functionalized compound having the formula 1:
wherein
each R 1 is independently selected from the group consisting of a saturated or unsaturated, linear, branched or cyclic aliphatic group having up to 30 carbon atoms, a heterocyclic group having from 3 to 30 carbon atoms, and an aromatic group having from 6 to 30 carbon atoms, where R 1 has the formula:
wherein R 10 is a cyclic aliphatic group or heterocyclic group of from 3 to 30 carbon atoms or an aromatic group and R 11 is an aliphatic group selected from the group consisting of linear or branched alkylene of from 1 to 30 carbon atoms, x is from 0 to 20, y is from 0 to 20, and wherein R 1 has at least a non-zero x or a non-zero y;
each R 2 and R 3 independently is an alkylene group having from 1 to 30 carbon atoms, a cycloalkylene group having from 3 to 30 carbon atoms, or an arylene group having from 6 to 30 carbon atoms;
R 4 is an alkyl group with 1 to 8 carbon atoms;
R 8 is an alkyl group with 1 to 10 carbon atoms;
R 9 is morpholino or an amino-functional group R 12 , having the general formula:
N(R 5 D) a (R 6 D) b ,
wherein R 5 and R 6 is independently phenylene or (—CHR 13 —) f , where f is from 1 to 20, and R 13 is hydrogen or a hydrocarbon group from 1 to 10 carbon atoms, D is a hydrogen atom, an alkoxysilane moiety or a —O(CO)NH—R 3 —Z group, a is from 0 to 2 and b is from 0 to 2, where one of a or b is a non-zero number and a+b=2, and Z is a hydrogen atom or Si(OR 4 ) n (R 8 ) 3-n group where n is 1 to 3;
each Z independently is a hydrogen atom or Si(OR 4 ) n (R 8 ) 3-n group;
m is greater than or equal to 1;
n is from 1 to 3,
and where the silane functionalized compound is free of hydroxyl and epoxy group, and
(b) a catalyst, and
(c) a polymeric resin.
2. The composition of claim 1 , wherein the silane functionalized compound having the formula 1 comprises, as a weight percentage of the composition, an amount from about 5 weight percent to about 80 weight percent.
3. The composition of claim 1 , wherein the catalyst is a metal organic compound.
4. The composition of claim 1 , wherein when the catalyst is present, the catalyst comprises from about 0.01 weight percent to about 10 weight percent of the composition.
5. The composition of claim 1 wherein the polymeric resin is selected from the group consisting of amine resins, epoxy resins, polydimethylsiloxane resins, acrylic resins, other organo-functionalized polysiloxane resins, polyimide resins, fluorocarbon resins, benzocyclobutene resins, fluorinated polyallyl ethers, polyamide resins, polyimidoamide resins, phenol cresol resins, aromatic polyester resins, polyphenylene ether (PPE) resins, bismaleimide resins, fluororesins, and combinations thereof.
6. The composition of claim 5 , wherein the composition further comprises an amine-containing curing agent, an amide-containing curing agent, or both, with each curing agent having one or more active hydrogen atoms.
7. The composition of claim 6 , wherein the curing agent comprises from about 0.1 weight percent to about 2 weight percent of the composition.
8. The composition of claim 1 , wherein the composition further comprises a solvent.
9. The composition of claim 1 , wherein the composition further comprises inorganic fillers, additional flame retardants, dyes, pigments, surfactants, flow control agents, and combinations thereof.
10. The composition of claim 1 , wherein m is 1.
11. The composition of claim 1 , wherein the silane functionalized compound has a weight average molecular weight of from about 350 to about 500,000.
12. The composition of claim 1 , wherein R 1 is
or combinations thereof.
13. The composition of claim 1 , wherein R 9 is an amino-functional group selected from the group consisting of diethylamino, morpholino, bis(tri-methoxysilylpropyl)amino, and N-ethyl-N-trimethoxysilylisobutylamino.
14. The composition of claim 1 , wherein the silane functionalized compound having the formula 1 is
15. The composition of claim 1 , wherein the silane functionalized compound having the formula 1 is formed from a process comprising:
(a) opening glycidyl units of an epoxy resin with a secondary amine to form hydroxyl groups; and
(b) reacting the hydroxyl groups formed in step (a) with an (alkoxysilyl)alkyl isocyanate or a mixture of an alkoxysilane)alkyl isocyanate and a non-silyl containing isocyanate to form the silane functionalized compound having the formula 1.
16. The composition of claim 15 , wherein the epoxy resin of step (a) is chain extended with a suitable bifunctional reactant to provide a chain extended epoxy resin comprising secondary hydroxyl groups pendant to the epoxy resin derived backbone.
17. The composition of claim 1 , wherein the silane functionalized compound having formula (1) contains at least one Z group which is a hydrogen atom.
18. The composition of claim 1 , wherein R 1 further comprises at least one heteroatom, wherein R 11 further comprises at least one heteroatom, or a combination thereof.
19. A silane functionalized compound having the formula 1:
wherein
each R 1 is independently selected from the group consisting of a saturated or unsaturated, linear, branched or cyclic aliphatic group having up to 30 carbon atoms, a heterocyclic group having from 3 to 30 carbon atoms, and an aromatic group having from 6 to 30 carbon atoms, where R 1 has the formula:
wherein R 10 is a cyclic aliphatic group or heterocyclic group of from 3 to 30 carbon atoms or an aromatic group and R 11 is an aliphatic group selected from the group consisting of linear or branched alkylene of from 1 to 30 carbon atoms, x is from 0 to 20, y is from 0 to 20, and wherein R 1 has at least a non-zero x or a non-zero y or both a non-zero x and a non-zero y;
each R 2 and R 3 independently is an alkylene group having from 1 to 30 carbon atoms, a cycloalkylene group having from 3 to 30 carbon atoms, or an arylene group having from 6 to 30 carbon atoms;
R 4 is an alkyl group with 1 to 8 carbon atoms;
R 8 is an alkyl group with 1 to 10 carbon atoms;
R 9 is an amino-functional group, R 12 , having the general formula:
N(R 5 D) a (R 6 D) b ,
wherein R 5 and R 6 is independently be phenylene or (—CHR 13 —) f , where f is from 1 to 20, and R 13 is hydrogen or a hydrocarbon group from 1 to 10 carbon atoms, D is a hydrogen atom or —O(CO)NH—R 3 —Z group, a is from 0 to 2 and b is from 0 to 2, where one of a or b is a non-zero number and a+b=2, and Z is a hydrogen atom or Si(OR 4 ) n (R 8 ) 3-n group where n is 1 to 3;
each Z independently is a hydrogen atom or Si(OR 4 ) n (R 8 ) 3-n group;
m is greater than or equal to 1;
n is from 1 to 3,
and where the silane functionalized compound is free of hydroxyl and epoxy groups, wherein R 1 optionally has at least one heteroatom, and wherein R 11 optionally has at least one heteroatom.
20. The composition of claim 19 , wherein the silane functionalized compound having formula (1) contains at least one Z group which is a hydrogen atom.