Method of making siloxane-based polymides

Details Method of making siloxane-based polymides Method of making siloxane-based polymides

2001-11-08

2003-05-06

Moore, Margaret G. (Department: 1712)

Synthetic resins or natural rubbers -- part of the class 520 ser

Synthetic resins

From silicon reactant having at least one...

C528S031000, C528S015000

Reissue Patent

active

RE038116

ABSTRACT:

CROSS-REFERENCE TO RELATED APPLICATIONS
Not applicable.
STATEMENT REGARDING FEDERALLY SPONSORED RESEARCH OR DEVELOPMENT
Not applicable.
REFERENCE TO A MICROFICHE APPENDIX
Not applicable.
FIELD OF THE INVENTION
This invention is directed to an improvement in the method of making siloxane-based polyamides described in a prior copending application, U.S. Ser. No. 08/904,709, filed Aug. 1, 1997, and entitled “Cosmetic Composition Containing Siloxane-Based Polyamides as Thickening Agents”, hereafter referred to as the '709 application.
BACKGROUND OF THE INVENTION
The present invention relates to a novel method of making siloxane-based polyamides.
There is a growing demand in the personal care arena for polymeric materials capable of thickening dimethylcyclosiloxanes in order to modify product viscosity in various market niche hair, skin, cosmetic, and underarm, applications.
The '709 application is directed to one type of a process for preparing siloxane-based polyamides. The process according to the '709 application involves many steps, and this results in cost prohibitive products which are difficult to produce in commercial quantity.
For example, in the '709 application process, a dimethyl hydride endblocked polydimethylsiloxane is first prepared containing the appropriate number of siloxane units to achieve a desired value of DP. The carboxylic acid group of undecylenic acid is then protected through reaction with hexamethyldisilazane. The dimethyl hydride endblocked polydimethylsiloxane and the protected undecylenic acid are reacted to produce a siloxane diacid, i.e., a carboxydecyl terminated polydimethylsiloxane. This reaction is accomplished in the presence of a platinum catalyst, and the product is washed with methanol to remove the trimethylsilyl protecting group from the protected siloxane diacid. The siloxane diacid is then reacted with an organic diamine to produce a siloxane-based polyamide.
Accordingly, a new process has been discovered herein that eliminates many of the otherwise costly steps involved in the process according to the '709 application.
The new process basically involves the addition of an olefinic acid with an organic diamine to produce an organic diamide. One the olefinic acid and the organic diamine are fully reacted, an ≡SiH endblocked polysiloxane is added in the presence of a platinum catalyst, to produce a siloxane-based polyamide via hydrosilylation. The resulting polymeric product is in the form of a high molecular weight thermoplastic polymer. The benefits of this process is that it allows for the production of a cost effective manufactured product in commercial quantity.
BRIEF SUMMARY OF THE INVENTION
This invention relates to a method of forming a siloxane-based polyamides which are useful as thickening agents to formulate a wide variety of cosmetic compositions. The polyamides of this invention are multiples of a unit represented by the following Formula A:
where:
(1) The degree of polymerization (DP) is 1-700, preferably 10-500, and more preferably 15-45. DP represents an average value for degree of polymerization of the siloxane units in the polymer with greater or lesser DP values centered around the indicated DP value.
(2) n is 1-500, particularly 1-100, and more particularly 4-25.
(3) X is a linear or branched chain alkylene having 1-30 carbons, particularly 3-10 carbons, and more particularly 10 carbons.
(4) Y is a linear or branched chain alkylene having 1-40 carbons, particularly 1-20 carbons, more particularly 2-6 carbons, and especially 6 carbons wherein
(a) The alkylene group may optionally and additionally contain in the alkylene portion at least one of (i) 1-3 amide linkages; (ii) a C5 or C6 cycloalkane; or (iii) phenylene, optionally substituted by 1-3 members which are independently C1-C3 alkyls; and
(b) the alkylene group itself may optionally be substituted by at least one of (i) hydroxy; (ii) a C3-C8 cycloalkane; (iii) 1-3 members which are independently C1-C3 alkyls; phenyl, optionally substituted by 1-3 members which are independently C1-C3 alkyls; (iv) a C1-C3 alkyl hydroxy; or (v) a C1-C6 alkyl amine; and
(c) Y can be Z where Z is T(R
20
)(R
21
)(R
22
) where R
20
, R
21
and R
22
are each independently linear or branched C1-C 10 alkylenes; and T is CR in which R is hydrogen, the group defined for R
1
-R
4
, or a trivalent atom such as N, P and Al.
(5) Each of R
1
-R
4
(collectively “R”) is independently methyl, ethyl, propyl, isopropyl, a siloxane chain, or phenyl, wherein the phenyl may optionally be substituted by 1-3 members which are methyl or ethyl. More particularly, R
1
-R
4
are methyl or ethyl, especially methyl.
(6) X, Y, DP, and R
1
-R
4
may be the same or different for each polyamide unit.
By “siloxane chain” is meant a group of units such as:
where R
30
and R
31
are each independently organic moieties; and each R
30
and R
31
are connected to silicon by a carbon-silicon bond.
The carbon numbers in the alkylene chain do not include the carbons in the extra segments or substitutions. Also, the polyamides must have a siloxane portion in the backbone and optionally may have a siloxane portion in a pendant or branched portion.
If repeated with no variations in the defined variables, Formula A is representative of a linear homopolymer. Variations of the invention include: (1) polyamides in which multiple values of DP, and of units X, Y, and R
1
-R
4
occur in one polymeric molecule, and wherein the sequencing of these units may be alternating, random or block; (2) polyamides in which an organic triamine or higher amine such as tris(2-aminoethyl)amine replaces the organic diamine in part, to produce a branched or crosslinked molecule; and (3) physical blends of any of (1) and (2) and/or linear homopolymers.
These and other features of the invention will become apparent from a consideration of the detailed description.
BRIEF DESCRIPTION OF THE SEVERAL VIEWS OF THE DRAWING
Not applicable.


REFERENCES:
patent: 3218344 (1965-11-01), Bailey
patent: 3313773 (1967-04-01), Lamoreaux
patent: 3392143 (1968-07-01), Holub
patent: 3746738 (1973-07-01), Pepe et al.
patent: 3892643 (1975-07-01), Tanaka et al.
patent: 4145508 (1979-03-01), Bargain et al.
patent: 5874069 (1999-02-01), Mendolia et al.
patent: 5919441 (1999-07-01), Mendolia et al.
patent: 6051216 (2000-04-01), Barr et al.

Affiliated with

Also associated with

Rating

Method of making siloxane-based polymides does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Method of making siloxane-based polymides, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Method of making siloxane-based polymides will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-3045726