Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – Mixing of two or more solid polymers; mixing of solid...
Reexamination Certificate
2002-02-04
2003-08-05
Dawson, Robert (Department: 1712)
Synthetic resins or natural rubbers -- part of the class 520 ser
Synthetic resins
Mixing of two or more solid polymers; mixing of solid...
C525S476000, C525S100000, C525S101000, C525S102000, C525S103000, C525S105000, C525S106000, C524S588000, C524S858000, C524S860000, C524S862000, C524S863000, C528S015000, C528S018000, C528S028000, C528S029000, C528S031000, C528S033000, C528S035000, C556S450000
Reexamination Certificate
active
06602964
ABSTRACT:
BACKGROUND OF THE INVENTION
1. Field of the Invention
This invention relates to silicone oligomers useful as reactive diluents for curable polymer systems, for example, silylated polyurethanes, silylated polyethers, or mixtures thereof. These systems may be used for either high modulus sealants in automotive applications or low viscosity formulations for coatings, adhesives and sealants.
2. Description of Related Art
It is known in the art to treat fillers or reinforcing agents to improve the physical or mechanical properties of plastics, resins, or rubbers reinforced with the filler. Much of the research in this area has centered on the pretreatment of glass fiber reinforcement materials for resins and rubbers. For example, U.S. Pat. No. 3,702,783 describes the application as a size to glass fibers of a blend of 3-glycidoxypropyltri ethoxysilane and methyltrimethoxysilane. U.S. Pat. No. 3,816,235 discloses a size composition for the treatment of glass fibers wherein the size composition contains a blend of aminoalkyltriethoxysilane and methyltriethoxysilane. U.S. Pat. No. 3,944,707 discloses the use as a size for glass fiber reinforcement for plastics, blends of vinyl silane or vinyl siloxanes and a beta-haloalkoxysilane. Similarly, U.S. Pat. No. 3,993,837 discloses glass fiber size compositions containing blends of epoxyalkylsilane or siloxane and a beta-haloalkoxysilane.
U.S. Pat. No. 3,148,169, discloses the pretreatment of clay filler with a silicone fluid to coat the clay particles to impart a hydrophobic character to the clay and to mask the acidic nature of the clay so that peroxides later used as cross-linking agents are not deactivated.
U.S. Pat. No. 4,049,865 discloses glass fiber size compositions containing a blend of an aminoalkylsilane and a vinyl silane.
U.S. Pat. No. 4,130,677 discloses the sizing of glass bottle surfaces with an aminoalkylsilane.
U.S. Pat. No. 4,179,537, discloses blends of an organofunctional silane, e.g., vinyltrialkoxysilanes, methacryloxyalkyltrialkoxysilanes, vinyltrihalosilanes and the like with a non-organofunctional silane, e.g., alkyltrialkoxysilanes, and the incorporation of such blends into organic resins, e.g., EPDM rubber for improving the adhesion between inorganic substrates, such as clay fillers and the resin. This patent suggests that the presence of siloxane oligomers in the resin-filler system could have a detrimental effect on coupling efficiency (col. 4, lines 54-63). The use of silanes having silicon-bonded 2-methoxyethoxy groups as coupling agents, e.g., vinyl-tris-(2-methoxyethoxy)silane (col. 2, lines 44-47) is also described in U.S. Pat. No. 4,179,537. Vinyl-tris-(2-methoxyethoxy)silane, has been used industrially for many years as a coupling additive in mineral-filled EPM and EPDM wire and cable insulations. EPM is an ASTM designation for copolymers of ethylene and propylene; EPDM is a terpolymer of ethylene, propylene, and a diene monomer, such as ethylidene norbornene or 1,4 hexadiene. Vinyl-tris-(2-methoxyethoxy)silane has been extensively used heretofore because it provides a unique balance of elastomer reinforcement and the degree of wet electrical stability required. However, it releases 2-methoxyethanol as a hydrolysis by-product when it is used and, unfortunately, 2-methoxyethanol is now being studied as a suspected teratogen. Consequently, coupling agent products based on vinyl-tris-(2-methoxyethoxy)silane are now facing continuing replacement pressure in the marketplace.
U.S. Pat. No. 4,550,056, describes electrical cables comprising a conductor and a coating of insulation on the conductor, the coating comprising a cured composition of
(1) an organic elastomer;
(2) an inorganic filler;
(3) a coupling composition comprising (a) an ethylenically unsaturated silane, having bonded to silicon, at least one hydroxy group and/or alkoxy group; (b) a methyl ethoxy siloxane oligomer fluid; and (c) a methyl vinyl siloxane oligomer fluid.
Commercial products used as coupling agents in elastomer/filler compositions include cohydrolysis products of dimethyl and vinylmethylchlorosilanes, which are used as a filler hydrophobe treatment on calcined clays. Such products, however, have a relatively high cost owing to the high cost of vinylmethyldichlorosilane.
U.S. Pat. No. 4,950,779 describes mixtures comprising cyclic, linear, and branched alkoxy functional silicone oligomers produced by condensation of organotrialkoxysilanes, such as methyltrimethoxysilane and vinyltrimethoxysilane, using formic acid, optionally with a strong acid catalyst.
U.S. Pat. No. 5,210,168 describes alkoxy functional silicone oligomer mixtures produced from organotrialkoxysilanes using a carboxylic acid, such as formic acid, and a strong acid catalyst.
U.S. Pat. No. 5,282,998 describes mixtures of linear and cyclic alkoxy functional silicone oligomers produced from vinyltrialkoxysilanes using hydrogen chloride catalyst and water.
U.S. Pat. No. 6,140,445 describes novel alkoxy functional silicone oligomers having alkoxysilylalkyl substituents on a backbone silicon atom. Such oligomers may be produced from vinylalkoxysiloxane oligomers by hydrosilation with an alkoxyhydridosilane, by hydrosilating a vinylalkoxysilane with a hydridoalkoxy silicone oligomer, or by condensation of a bis-alkoxysilane having silicon atoms joined by other than an Si—O bond, optionally with other alkoxysilanes. Such oligomers are disclosed to be useful as coatings or adhesives, or additives therefor.
U.S. Pat. No. 6,207,783 discloses an oligomer of the formula:
[R
3
SiO
1/2
]
m
[O
1/2
Si(R)
2
O
1/2
]
n
[SiO
3/2
R]
o
[SiO
4/2
]
p
(I)
wherein each R is selected individually from the group consisting of R
1
, —OR
2
, and —OR
3
; each R
1
is independently a substituted or unsubstituted hydrocarbon group; each R
2
is independently a C
1
-C
6
alkyl group as defined for R
1
or an acyl group; and each R
3
is independently an alkyl or alkenyl group having at least 8 carbon atoms; with the provisos that if R
3
is alkenyl, there is no unsaturation with two carbon atoms adjacent to the oxygen atom or the —OR
3
group; at least one R group is —OR
3
; at least one quarter of all R groups are —OR
2
or —OR
3
; m=2 to 20; n=0 to 50; o=0 to 20; and p=0 to 10. The oligomer is a useful component of insulation formulations for wire and cable used in underground locations.
U.S. Pat. No. 6,310,170 discloses compositions comprising a silylated polymer and an adhesion promoter, the silylated polymer having an inorganic or organic backbone and at least two groups thereon selected from alkoxysilyl, aryloxysilyl, alkyloximinosilyl, and silanol groups and the adhesion promoter being a silane adhesion promoter of the formula:
R
1
is a branched or cyclic alkylene group, an arylene group or an alkarylene group, any of which may be optionally interrupted by one or more ether oxygen atoms or a (poly)sulfide bridge, provided that R
1
has at least 4 carbon atoms; R
2
is an alkyl, aryl or alkaryl radical having 1 to 6 carbons; R
3
is a C
1
to C
6
alkoxy group or a C
3
to C
5
ketoximato group; R
4
is hydrogen, a hydrocarbon group, which may optionally be substituted, or a group which will thermally deblock to form an amine group containing the nitrogen atom to which it is attached; and z is 0 or 1.
U.S. Pat. No. 6,323,277 discloses oligomers of the formula:
[R
3
SiO
1/2
]
m
[O
1/2
Si(R)
2
O
1/2
]
n
[SiO
3/2
R]
o
[SiO
4/2
]
p
(I)
wherein each R is selected individually from the group consisting of B, R
1
, —OR
2
, R
3
and R
4
; B is an organosilyl functional group bridged to the Si atom of the siloxane oligomer backbone by an Si—C bond; each R
1
is independently a saturated or aromatic hydrocarbon group of 1 to 16 carbon atoms; each R
2
is independently a group as defined for R
1
or an acyl group; and each R
3
is independently a monovalent organic radical containing an aliphatically unsaturated hydrocarbon group and each R
4
is a monovalent organic radical
Handel Richard E.
Huang Misty
Petty Herbert
Crompton Corporation
Dawson Robert
Dilworth Michael P.
Robertson Jeffrey B.
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