Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – From silicon reactant having at least one...
Reexamination Certificate
1999-10-21
2001-04-03
Moore, Margaret C (Department: 1712)
Synthetic resins or natural rubbers -- part of the class 520 ser
Synthetic resins
From silicon reactant having at least one...
C528S025000, C528S031000, C556S456000, C556S462000, C556S453000
Reexamination Certificate
active
06211323
ABSTRACT:
BACKGROUND OF THE INVENTION
Alkylaryl and alkylmethyl organosiloxanes and methods for their preparation have been disclosed in the art. For example, Ryan in U.S. Pat. No. 3,088,964 discloses an organodisiloxane having the formula (CH
3
CH(C
6
H
5
)CH
2
(R)
2
Si)
2
O wherein each R is a monovalent hydrocarbon radical free of aliphatic unsaturation, there being no more than one CH
3
CH(C
6
H
5
)CH
2
— radical per Si atom, and R is preferably methyl. Ryan also discloses a process for the production of aralkyl substituted organosilicon compounds in improved yields which comprises reacting (1) alpha-methylstyrene with (2) an organosilicon compound of the formula R
x
HSiCl
3−x
where R represents a monovalent hydrocarbon radical free of aliphatic unsaturation and x is an integer of from 1 to 2 inclusive, by contacting (1) and (2) in the liquid phase in the presence of a catalytic quantity of chloroplatinic acid, where R is preferably methyl. Ryan further discloses that the resulting addition product can be hydrolyzed with water.
Kookootsedes et al. in U.S. Pat. No. 3,186,964 disclose a composition of matter consisting essentially of a toluene soluble copolymer of (1) from 10 to 90 mole percent polymeric units of the formula (C
6
H
5
R—)(CH
3
)SiO, wherein R is an alkylene radical of from 2 to 3 inclusive carbon atoms such as ethylene or propylene, and (2) from 10 to 90 mole percent polymeric units of the formula (CH
3
)(R′)SiO wherein R′ is an alkyl radical of from 2 to 3 inclusive carbon atoms, where R′ is preferably ethyl. Kookootsedes et al. further discloses several methods of preparing these siloxane copolymers, the preferred method being to first effect a reaction between alpha-methylstyrene and some of the silicon-bonded hydrogen atoms in a methylhydrogensiloxane, from 0.1 to 0.9 mole percent of alpha-methylstyrene per mole of methylhydrogensiloxane is used in the presence of chloroplatinic acid as the catalyst, the addition reaction resulting in the attachment of 2-phenylpropyl groups to some of the silicon atoms having hydrogen attached thereto, the reaction being carried out at temperatures of from 70 to 175° C. After the first reaction is completed, a reaction is then effected between either ethylene and/or propylene and the remaining silicon-bonded hydrogen atoms in the copolymer, preferably an excess of ethylene and/or propylene is used so that the SiH content of the copolymer is reduced to a very small value. It is further disclosed that this reaction is also best carried out in the presence of chloroplatinic acid at temperatures of from 75 to 200° C.
Pater in U.S. Pat. No. 3,221,040 discloses a copolymeric organosiloxane oil of the formula R
3
SiO((CH
3
)
2
SiO)
x
(CH
3
(C
2
H
5
)SiO)
w
(C
6
H
4
(R
1
)-C
2
H
4
(CH
3
)SiO)
y
SiR
3
wherein R is a hydrocarbyl group, preferably methyl, R
1
is selected from the class consisting of a hydrogen atom and a methyl radical, x is a number, w is a number, the sum of x and w is at least 1, y is a number of at least one, the ratio of x+w to y is from 1:1 to 3:1, and the viscosity of the copolymeric organosiloxane oil at 25° C. is from 25 centistokes to 10,000 centistokes.
Legrow et al. in U.S. Pat. No. 5,384,383 disclose pristine phenylpropylalkylsiloxanes consisting of mixtures of linear and cyclic siloxanes containing the structure
Legrow et al. further disclose that these phenylpropylalkylsiloxanes are produced by a method comprising i) hydrolyzing a pure phenylpropylalkyldichlorosilane having a purity of greater than 99.9% and containing no detectable silicon hydride, free organics, or free inorganics and thereafter recovering the hydrolysis reaction product, and ii) equilibrating the hydrolysis reaction product with a triorganosilyl endblocker in the presence of a heterogeneous acid catalyst.
Biggs et al. in U.S. Pat. No. 5,516,870 disclose a method of making alkylmethyl cyclic siloxanes comprising (i) forming a reaction mixture containing an alpha-olefin, one or more silanol-free methylhydrogen cyclic siloxanes, and less than about 100 parts per million water, (ii) contacting the essentially anhydrous silanol-free reaction mixture with anhydrous platinum supported on carbon catalyst, (iii) agitating the mixture and catalyst to form an alkylmethyl cyclic siloxane, and (iv) continuing the reaction until the alkylmethyl cyclic siloxane is ≡SiH free; SiH free being the amount of hydrogen present as SiH within the detection limits of Fourier Transform Infrared Spectroscopy or less than one part per million.
Biggs et al. in U.S. Pat. No. 5,554,708 discloses a method of making linear triorganosiloxy endcapped methylhydrogen polysiloxanes comprising (i) forming a reaction mixture containing a silanol-free hexaorganodisiloxane, one or more silanol-free methylhydrogen cyclic siloxanes, and less than about 100 parts per million water, (ii) contacting the reaction mixture with anhydrous trifluoromethane sulfonic acid catalyst, and (iii) agitating the mixture and the catalyst at below 100° C. to form a linear triorganosiloxy endcapped methylhydrogen polysiloxane.
SUMMARY OF THE INVENTION
This invention relates to triorganosiloxy-endblocked polymethylalkylsiloxane-polyalkylarylsiloxane terpolymers.
This invention also relates to methods of preparing triorganosiloxy-endblocked polymethylalkylsiloxane-polyalkylarylsiloxane terpolymers.
It is an object of this invention to produce triorganosiloxy-endblocked polymethylalkylsiloxane-polyalkylarylsiloxane terpolymers by a highly efficient robust method which allows control of the viscosity of the terpolymer.
DETAILED DESCRIPTION OF THE INVENTION
In a first embodiment, this invention relates to a triorganosiloxy-endblocked poly(methyl(C6-40alkyl)siloxane)-poly(methyl(aralkyl)siloxane)-poly(methyl(C2-C4alkyl)siloxane) terpolymer having the formula:
(R)
3
SiO(CH
3
R
1
SiO)
x
(CH
3
R
2
SiO)
y
(CH
3
R
3
SiO)
z
Si(R)
3
wherein each R is independently selected from the group consisting of alkyl groups, aryl groups, alkaryl groups, and aralkyl groups, R
1
denotes an alkyl group having from 6 to 40 carbon atoms, R
2
denotes an aralkyl group, R
3
denotes an alkyl group having from 2 to 4 carbon atoms, x has an average value of from 25 to 120, y has an average value of from 5 to 40, and z has an average value of from 0.1 to 20.
The R group is exemplified by alkyl groups such as methyl, ethyl, propyl, isopropyl, butyl, and hexyl, aryl groups such as phenyl, xenyl, or naphthyl, alkaryl groups such as tolyl or xylyl, or aralkyl groups such as benzyl, phenylethyl, or 2-phenylpropyl. The R groups can be the same or different as desired. However, it is especially preferred that R is methyl.
The alkyl groups of R
1
are exemplified by hexyl, octyl, decyl, dodecyl, tetradecyl, hexadecyl, octadecyl, -C
20
H
41
, -C
22
H
45
, -C
24
H
49
, -C
26
H
53
, -C
28
H
57
, -C
30
H
61
, -C
32
H
65
, -C
34
H
69
, -C
36
H
73
, -C
38
H
77
, and -C
40
H
81
. Preferably the alkyl group is selected from the group consisting of decyl, dodecyl, tetradecyl, hexadecyl, octadecyl, and -C
20
H
41
. Especially preferred is dodecyl.
The aralkyl groups of R
2
are exemplified by benzyl, 4-methylbenzyl, o-methoxybenzyl, p-methoxybenzyl, diphenylmethyl, 2-phenylethyl, 2-phenylpropyl, and 3-phenylpropyl, however, 2-phenylpropyl is especially preferred.
The alkyl groups of R
3
are exemplified by ethyl, propyl, and butyl, with ethyl being preferred.
In a second embodiment, this invention relates to a method of making a triorganosiloxy-endblocked poly(methyl(C6-C40alkyl)siloxane)-poly(methyl(aralkyl)siloxane)-poly(methyl(C2-C4alkyl)siloxane) terpolymer comprising: (i) reacting at temperature of less than or equal to 120° C. a mixture comprising (a) a linear triorganosiloxy-endblocked polymethylhydrogensiloxane, (b) an alpha-olefin having from 6 to 40 carbon atoms, and (c) a platinum-containing catalyst, (ii) reacting at temperature of less than or equal to 120° C. a mixture comprising (d) the product of (i), and (e) an unsaturated aromatic compound to form a triorganosiloxy-endblocked poly(methylalkylsilo
Akinaga Keiichi
Feng Qian Jane
Petroff Lenin James
Dow Corning Corporation
Moore Margaret C
Troy Timothy J.
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