Coating processes – With post-treatment of coating or coating material – Heating or drying
Reexamination Certificate
2001-05-15
2002-11-05
Dawson, Robert (Department: 1712)
Coating processes
With post-treatment of coating or coating material
Heating or drying
C556S444000, C556S445000, C528S028000, C528S027000, C008S127500, C008S128300, C424S070120, C427S389900, C427S389000, C427S387000
Reexamination Certificate
active
06475568
ABSTRACT:
BACKGROUND OF THE INVENTION
1. Field of the Invention
The present invention relates to novel block, non-(AB)
n
, linear copolymers comprising units of polysiloxane and polyalkyleneoxide linked by tertiary amino groups, a method for the preparation of these copolymers, and to the use of these copolymers as conditioning ingredients in hair care and skin care products and as textile softeners, particularly, re-wettable textile softeners.
2. Description of Related Art
Examples of non-hydrolyzable siloxane-polyalkyleneoxide block copolymers are known in the prior art.
U.S. Pat. No. 3,761,444 discloses an improvement in the manufacture of epoxy substituted siloxanes. Lower molecular weight epoxy substituted siloxanes are equilibrated with other siloxanes to produce siloxane copolymers containing the substituents of both the epoxy siloxane and the other siloxanes. This is accomplished with a basic equilibration catalyst and in the presence of small quantities of water and silanol.
U.S. Pat. No. 4,101,272 discloses a process for the treatment of fibrous materials to improve their properties, in which the fibrous materials are treated with a composition containing: a component A selected from the class consisting of polyorganosiloxanes of the general formula
R
n
SiO
(4−n):2
in which n has an average value in the range 1.8 to 2.2, and R represents organic radicals attached to the silicon atoms by carbon-silicon bonds; wherein between 1.0 and 50 percent of the radicals R consist of one or more organic radicals containing an epoxide group and selected from the class consisting of: 1,2-epoxyethyl; 3,4-epoxycyclohexyl; 6-methyl-3,4-epoxycyclohexyl; 3,4-epoxycyclohexyl- 1-ethyl; 9,10-epoxystearyl; 3-(2,3-epoxypropoxy)propyl; p-(2,3-epoxybutyl)-phenyl; and 3-(3,4-epoxybutyl)cyclohexyl, and the remainder of the radicals R consist of one or more organic radicals selected from the class consisting of alkyl and aryl radicals; and a polyamine component B which consists of one or more organic compounds each with two or more primary and/or secondary amino groups attached to aliphatic carbon atoms such that there are at least 5 carbon atoms per amino group, or two or more groups capable of providing, by reaction, primary and/or secondary amino groups; and allowing the components A and B to react chemically.
U.S. Pat. No. 4,242,466 discloses organic ethers including polyethers having two CH
2
=C(R)CH
2
— end groups per molecule wherein R is a monovalent hydrocarbon group that are reacted with organohydrosiloxanes under hydrosilation reaction conditions in the presence of a platinum catalyst to form nonhydrolyzable siloxane block copolymers. Non-hydrolyzable linear block copolymers substantially free of silicon-bonded hydrogen are obtained with linear dihydropolyorganosiloxane reactants and linear ethers or polyethers.
U.S. Pat. No. 4,833,225 discloses polyquaternary polysiloxane polymers having defined repeating units. The compounds may be synthesized by an addition reaction between an &agr;,&ohgr;-hydrogenpolysiloxane of a given formula and epoxides which have a terminal olefinic bond, and reacting the product obtained with a diamine. The polymers may be used in cosmetic preparations, especially in hair cosmetics.
U.S. Pat. Nos. 5,807,956 and 5,981,681 disclose non-hydrolyzable, block, (AB)
n
A type, copolymers comprising alternating units of polysiloxane and amino-polyalkyleneoxide and provide a method for the preparation of these copolymers. Also provided is the use of these copolymers as softeners, in particular durable, hydrophilic textile softeners, which improve tactile properties of the textiles substrates treated with the commercial soil release finishes, without substantially detracting from their properties. The copolymers have alternating units of polysiloxane [X(C
a
H
2a
O)
b
R
2
[(SiO(R
1
)
2
]
c
Si(R
1
)
2
R
2
(C
a
H
2a
O)
b
X] and polyalkyleneoxides [YO(C
a
H
2a
O)
d
Y] wherein R
1
is a C
1
to C
4
alkyl, preferably methyl, R
2
is a divalent organic moiety, X and Y are divalent organic groups selected from a secondary or tertiary amine and a ring opened epoxide, such that when X is a ring opened epoxide, Y is an amine and vice versa, a=2 to 4, preferably 2 to 3, b=0 to 100, d=0 to 100, b+d=1 to 100, preferably 10 to 50, and c=1 to 500, preferably 10 to 100.
U.K. Patent No. 1,213,779 discloses a process for the production of an organo-silicon compound by the addition of a hydrogen-silane or -siloxane to an olefinically-unsaturated organic compound in the presence of a catalyst, trimethyl-dipyridine-platinum-iodide.
DE 19817776 A1 provides another example of the (AB)
n
aminopolysiloxane polyalkylyneoxide copolymers. These copolymers are derived from reaction of the acrylate terminated polyether with amine terminated polysiloxanes under Michael's addition conditions.
The disclosures of the foregoing are incorporated herein by reference in their entirety.
SUMMARY OF THE INVENTION
The present invention is directed to non-hydrolyzable, block, non-(AB)
n
type copolymers comprising units of polydimethylsiloxane and polyalkyleneoxide linked by tertiary amino groups.
In another aspect, the present invention is directed to a method for the preparation of these copolymers from the epoxy terminated polydimethylsiloxanes and epoxy terminated polyalkyleneoxides with primary amines or a combination of primary and secondary amines, where secondary amine functions as a chain stopper.
In still another aspect, the present invention is directed to the use of these copolymers as conditioning ingredients for hair care and skin care, as well as textile softeners to improve wettability and tactile properties of textile substrates.
More particularly, the present invention is directed to a composition comprising non-hydrolyzable, block, non-(AB)
n
type copolymers comprising units of the formula {XR
2
[(SiO(R
1
)
2
]
x
Si(R
1
)
2
R
2
X}, units of the formula {YO(C
a
H
2a
O)
b
Y}, and linking groups —NR
3
—, wherein R
1
is alkyl, R
2
is a divalent organic moiety, X and Y are independently selected divalent organic groups formed by the ring opening of an epoxide, R
3
is selected from the group consisting of alkyl, aryl, aralkyl, oxygen-containing alkyl, oxygen-containing aryl, and oxygen-containing aralkyl, a=2 to 4, b=2 to 100, and x=1 to 500.
In another embodiment, the present invention is directed to a method of making non-hydrolyzable, block, non-(AB)
n
type copolymers comprising units of the formula {XR
2
[(SiO(R
1
)
2
]
x
Si(R
1
)
2
R
2
X}, units of the formula {YO(C
a
H
2a
O)
b
Y}, and linking groups —NR
3
—, wherein R
1
is alkyl, R
2
is a divalent organic moiety, X and Y are independently selected divalent organic groups formed by the ring opening of an epoxide, R
3
is selected from the group consisting of alkyl, aryl, aralkyl, oxygen-containing alkyl, oxygen-containing aryl, and oxygen-containing aralkyl, a=2 to 4, b=2 to 100, and x=1 to 500, wherein the method comprises reacting
(1) polysiloxanes of the formula QR
2
[(SiO(R
1
)
2
]
c
Si(R
1
)
2
R
2
Q, and
(2) polyalkyleneoxides of the formula {ZO(C
b
H
2b
O)
d
Z}, wherein Q and Z are epoxide containing groups, with at least one primary amine or a combination of primary and secondary amines.
In still another embodiment, the present invention is directed to a method for softening a substrate comprising applying to said substrate a composition comprising non-hydrolyzable, block, non-(AB)
n
type copolymers comprising units of the formula {XR
2
[(SiO(R
1
)
2
]
x
Si(R
1
)
2
R
2
X}, units of the formula {YO(C
a
H
2a
O)
b
Y}, and linking groups —NR
3
—, wherein R
1
is alkyl, R
2
is a divalent organic moiety, X and Y are independently selected divalent organic groups formed by the ring opening of an epoxide, R
3
is selected from the group consisting of alkyl, aryl, aralkyl, oxygen-containing alkyl, oxygen-conta
Crompton Corporation
Dawson Robert
Dilworth Michael P.
Peng Kuo-Liang
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