Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – From silicon reactant having at least one...
Reexamination Certificate
2001-10-04
2003-06-10
Dawson, Robert (Department: 1712)
Synthetic resins or natural rubbers -- part of the class 520 ser
Synthetic resins
From silicon reactant having at least one...
C528S015000, C528S028000, C528S031000, C528S038000, C525S100000, C525S101000, C525S102000, C525S431000, C525S474000, C525S477000, C525S478000, C525S509000
Reexamination Certificate
active
06576737
ABSTRACT:
This invention relates to curable compositions which cure into fluorinated elastomers having a good adhesion to a variety of substrates such as polyphenylene sulfide resins, polyamide resins and polyimide resins.
BACKGROUND OF THE INVENTION
Curable fluorinated elastomer compositions utilizing addition reaction between alkenyl and hydrosilyl radicals are well known in the art. It is also known from JP-A 9-95615 to add an organopolysiloxane having a hydrosilyl radical and an epoxy and/or trialkoxy radical as a third component to such a composition for rendering it self-adhesive. This composition can be cured by brief heating while it can bond to a variety of substrates during curing. Since the cured product has good solvent resistance, chemical resistance, heat resistance, low-temperature properties, low moisture permeability and electrical properties, the composition is useful in an adhesion application in a variety of industrial fields where such properties are required.
The composition forms a satisfactory bond to such plastics as epoxy resins, phenolic resins and polyester resins, but a less satisfactory bond to such plastics as polyphenylene sulfide (PPS) resins, polyamide resins and polyimide resins. The composition is not applicable where PPS, polyamide and polyimide resins are used. Since PPS, polyamide and polyimide resins are often used as automotive parts and electrical and electronic parts, an improvement in bond to these plastics is desired.
SUMMARY OF THE INVENTION
An object of the invention is to provide a novel and improved curable composition which cures into a fluorinated elastomer that firmly bonds to PPS, polyamide and polyimide resins.
The invention pertains to a curable composition comprising (A) a fluorinated amide compound having at least one alkenyl radical in a molecule, (B) a fluorinated organohydrogensiloxane as a crosslinker/chain extender, and (C) a platinum group compound as a catalyst. It has been found that by adding to this composition (D) a first organosiloxane having in a molecule at least one hydrogen atom directly attached to a silicon atom (i.e., SiH radical), and at least one epoxy and/or trialkoxysilyl radical each attached to a silicon atom through a carbon atom or a carbon atom and an oxygen atom, and preferably, at least one perfluorooxyalkyl or perfluoroalkyl radical as a tackifier, and (E) a second organosiloxane having in a molecule at least one hydrogen atom directly attached to a silicon atom, at least one cyclic carboxylic anhydride residue attached to a silicon atom through a carbon atom, and at least one monovalent perfluorooxyalkyl or perfluoroalkyl radical attached to a silicon atom through a carbon atom as an adhesive reaction accelerator, there is obtained a curable composition which cures into a fluorinated elastomer that not only has good solvent resistance, chemical resistance, heat resistance, low-temperature properties, low moisture permeability and electrical properties, but also firmly bonds to a variety of substrates including PPS, polyamide and polyimide resins.
The invention provides a curable composition comprising as essential components,
(A) a fluorinated amide compound having at least one alkenyl radical in a molecule,
(B) a fluorinated organohydrogensiloxane,
(C) a platinum group compound,
(D) a first organosiloxane having in a molecule at least one hydrogen atom directly attached to a silicon atom, and at least one of epoxy radicals and trialkoxysilyl radicals each attached to a silicon atom through a carbon atom or a carbon atom and an oxygen atom, and
(E) a second organosiloxane having in a molecule at least one hydrogen atom directly attached to a silicon atom, at least one cyclic carboxylic anhydride residue attached to a silicon atom through a carbon atom, and at least one monovalent perfluorooxyalkyl or perfluoroalkyl radical attached to a silicon atom through a carbon atom.
DESCRIPTION OF THE PREFERRED EMBODIMENT
Briefly stated, the curable composition of the invention contains (A) a fluorinated amide compound having an alkenyl radical as a base polymer, (B) a fluorinated organohydrogensiloxane as a crosslinker and chain extender, (C) a platinum group compound as a catalyst, (D) a first organosiloxane as a tackifier, and (E) a second organosiloxane as an adhesive reaction accelerator.
Component (A) is a fluorinated amide compound which should have at least one alkenyl radical in a molecule, and preferably two alkenyl radicals at opposite ends. In the compound, fluorine is preferably contained as a monovalent perfluorooxyalkyl, monovalent perfluoroalkyl, divalent perfluorooxyalkylene or divalent perfluoroalkylene radical. Preferably the compound has the following linkage.
Herein R
2
is hydrogen or a substituted or unsubstituted monovalent hydrocarbon radical having 1 to 10 carbon atoms, especially 1 to 8 carbon atoms, and preferably free of aliphatic unsaturation.
Further, the compound may have the following linkage.
Herein R
2
is as defined above; R
3
is a substituted or unsubstituted divalent hydrocarbon radical which may be separated by at least one atom of oxygen, nitrogen and silicon atoms; R
4
and R
5
each are a substituted or unsubstituted divalent hydrocarbon radical.
The fluorinated amide compound (A) is preferably of the following general formula (1).
Referring to formula (1), R
1
stands for substituted or unsubstituted monovalent hydrocarbon radicals preferably of 1 to 10 carbon atoms, more preferably 1 to 8 carbon atoms, and also preferably free of aliphatic unsaturation. Examples include alkyl radicals such as methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, pentyl, hexyl, octyl and decyl; cycloalkyl radicals such as cyclopentyl, cyclohexyl and cycloheptyl; alkenyl radicals such as vinyl, allyl, propenyl, isopropenyl, butenyl, and hexenyl; aryl radicals such as phenyl, tolyl, xylyl and naphthyl; aralkyl radicals such as benzyl, phenylethyl and phenylpropyl; and substituted ones of these radicals in which some or all of the hydrogen atoms are replaced by halogen atoms or the like, typically fluorinated alkyl radicals such as chloromethyl, chloropropyl, bromoethyl, 3,3,3-trifluoropropyl, and 6,6,6,5,5,4,4,3,3-nonafluorohexyl.
R
2
stands for hydrogen or substituted or unsubstituted monovalent hydrocarbon radicals preferably of 1 to 10 carbon atoms, more preferably 1 to 8 carbon atoms, and also preferably free of aliphatic unsaturation, as defined above for R
1
. Examples of the monovalent hydrocarbon radicals are as exemplified above for R
1
, for example, alkyl radicals such as methyl, ethyl, propyl, and isopropyl; cycloalkyl radicals such as cyclohexyl; alkenyl radicals such as vinyl and allyl; aryl radicals such as phenyl and tolyl; and substituted ones of these radicals in which some hydrogen atoms are replaced by halogen atoms or the like, typically fluorinated alkyl radicals such as chloromethyl, chloropropyl, 3,3,3-trifluoropropyl, and 6,6,6,5,5,4,4,3,3-nonafluorohexyl.
Q is a radical of the following general formula (2) or (3).
R
2
in formula (2) is as defined above. R
3
may be selected from substituted or unsubstituted divalent hydrocarbon radicals, preferably from divalent hydrocarbon radical of 1 to 20 carbon atoms, especially 2 to 10 carbon atoms. Examples include alkylene radicals such as methylene, ethylene, propylene, methylethylene, butylene and hexamethylene; cycloalkylene radicals such as cyclohexylene; arylene radicals such as phenylene, tolylene, xylylene, naphthylene and biphenylene; substituted ones of these radicals in which some hydrogen atoms are replaced by halogen atoms or the like; and combinations of these substituted or unsubstituted alkylene and arylene radicals.
R
3
may contain one or more atoms of oxygen, nitrogen and silicon atoms at an intermediate of its linkage. In this case, the oxygen atom intervenes in the linkage of R
3
in the form of —O—. The nitrogen atom intervenes in the linkage of R
3
in the form of —NR′—wherein R′ is hydrogen, alkyl of 1 to 8 carbon atoms, especially 1 to 6 carbon atoms or aryl. The sili
Arai Masatoshi
Matsuda Takashi
Shiono Mikio
Birch & Stewart Kolasch & Birch, LLP
Dawson Robert
Robertson Jeffrey B.
Shin-Etsu Chemical Co. , Ltd.
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