Polysiloxane-polybutylene copolymers

Details Polysiloxane-polybutylene copolymers Polysiloxane-polybutylene copolymers

1999-06-30

2001-03-20

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...

C525S100000, C528S015000

Reexamination Certificate

active

06204329

ABSTRACT:

FIELD OF THE INVENTION
The present invention relates to novel polysiloxane-polybutylene copolymers. Specifically, the present invention relates to such copolymers in which polybutylene chains are grafted onto polysiloxane backbones. These copolymers are particularly suited for uses in the personal care industry.
BACKGROUND OF THE INVENTION
The combination of silicon-containing molecules with polybutylene is known in the art, for instance, Iwahara et al. in U.S. Pat. No. 4,904,732 teach the formation of an isobutylene polymer having at least one silicon-containing group which is crosslinkable by the formation of a siloxane bond. The polymer described therein is said to be curable at room temperature to produce materials with weatherability, weather resistance, heat resistance, electric isolation and gas impermeability. This patent does not, however, describe polysiloxane-polybutylene copolymers in which polybutylene chains are grafted onto polysiloxane backbones.
Similarly, Saam in U.S. Pat. No. 4,808,664 teaches the formation of polyisobutylene oligomers containing siloxane functional terminal groups. This patent teaches that such materials cure at room temperature in the presence of moisture. Again, however, the patent teaches a main chain of isobutylene monomer units with a siloxane functional terminal unit as opposed to polysiloxane backbone copolymers with polybutylene chains grafted thereon as claimed herein.
Kennedy et al. in U.S. Pat. No. 5,663,245 teach novel multi-arm polymers comprising polyisobutylene arms connected to a well-defined siloxane core. This patent teaches that the resultant materials are acid stable, have low viscosity with high molecular weight, and are useful as motor oil additives. This patent, however, does not describe the copolymers claimed herein.
In U.S. Pat. No. 5,741,859, there is described a method of preparing a polyisobutylene-siloxane block copolymer via non-equilibrium anionic polymerisation of a diorganocyclotrisiloxane using a silanolate functional polyisobutylene as the initiator. Resulting copolymers are described and include certain di-block, tri-block, branched or star copolymers.
We have now discovered novel polysiloxane-polybutylene copolymers which have both siloxane and organic copolymer characteristics and, as such, are particularly useful in the personal care industry.
BRIEF SUMMARY OF THE INVENTION
The present invention provides in one of its aspects a polysiloxane-polybutylene copolymer having the polybutylene grafted onto a polysiloxane backbone, said copolymer having the structure
R
a
X
(3−a)
Si—O—(R
2
SiO)
q
—(RXSiO)
y
—SiX
(3−a)
R
a
wherein each R is independently selected from the group consisting of hydrogen, hydroxyl, alkoxy, halogen, siloxane units, organic groups having from 1-30 carbon atoms and substituted organic groups having from 1-30 carbon atoms, X is a polybutylene having a molecular weight greater than about 500, a is 2 or 3, q is a positive integer with a value of at least 1 and y is a positive integer with a value of at least 2.
The resultant copolymers have both organic and silicone characteristics and, as such, have a variety of utilities. For instance, the copolymers may be used in cosmetic and medical utilities where it is desirable to have materials with both silicone and organic characteristics. Similarly, the copolymers are useful as compatibilizers for silicone and organic materials and are useful in polishes, coatings, lubricants, textiles and the like.
DETAILED DESCRIPTION OF THE INVENTION
The copolymers of the invention have the structure:
R
a
X
(3−a)
Si—O—(R
2
SiO)
q
—(RXSiO)
y
—SiX
(3−a)
R
a
  I
In this structure, each R is independently selected from the group consisting of hydrogen, hydroxyl, alkoxy, halogen, siloxane units, organic groups having from 1-30 carbon atoms and substituted organic groups having from 1-30 carbon atoms. The alkoxy groups can be, for example, methoxy, ethoxy, propoxy and the like. The halogens can be, for example, chlorine, bromine and the like. The siloxane units can be, for example, dimethylsiloxane units incorporated to form resinous polysiloxane structures. The organic groups can include, for example, alkyls such as methyl, ethyl, propyl, butyl, nonyl, dodecyl, tetradecyl, hexadecyl, octadecyl, eicosyl (C
20
) and tricontyl (C
30
), cycloalkyls such as cyclohexyl, unsaturated alkenyls or alkynyls such as vinyl, allyl and hexenyl, aryls such as phenyl, and the like. If desired the organic groups can be substituted with hetero atoms such a nitrogen, sulfur, halogens, silicon and oxygen. For example, the organic R groups can contain silicon and oxygen atoms (e.g., siloxane units), hydroxyl groups, alkoxy groups or nitrogen atoms. In one preferred embodiment of the invention, a majority of the R groups (e.g., 80%) comprise methyl groups. In another embodiment of the invention, at least one of the R groups comprise an organic group having form 10 to 30 carbon atoms to add additional organic characteristics.
It should be noted that the R groups can be different in the same unit. For instance, the (R
2
SiO) unit could comprise (MeOctSiO), (MeDDSiO)or (MePhSiO) (Me=methyl, Oct=octyl, DD=dodecyl and Ph=phenyl). Similarly, there could be different (R
2
SiO) units in the same copolymer. For instance, there could be (MeOctSiO), (MeDDSiO) and (Me
2
SiO) units in the same polymer (Me=methyl, DD=dodecyl and Oct=octyl).
In the above structure I, X is a polybutylene. Such polybutylenes have repeating units of the structure
These polymers are typically terminated at one end with a hydrogen, an alkyl group, a halogen, or other conventional chain terminating groups and at the other end with an olefinic group as set forth below. Preferred are polymers with repeating isobutylene units (i.e., polyisobutylene).
The polybutylene chains which comprise X generally have a number average molecular weight of at least 500 and may go up to several hundred thousands, preferably in the range of 500 to about 50,000 and most preferably 1000 to about 20,000. In a preferred embodiment, the polybutylene unit is a poly-isobutylene with a number average molecular weight in the range of about 1000 to 20,000.
In the above structure I, a is 2 or 3, q is a positive integer, preferably 2 to 200, and y is a positive integer, with a value of from 2 preferably up to 200.
In one embodiment of the invention, the copolymer is of the structure:
R
3
Si—O—(R
2
SiO)
q
—(RXSiO)
y
—SiR
3
  II
wherein R, X, q and y are as defined above.
In a preferred embodiment, a majority of the R groups are methyl and X is polyisobutylene. In another preferred embodiment, the (R
2
SiO) units comprise (CH
3
RSiO) units, wherein R is as defined above. In yet another preferred embodiment, the (R
2
SiO) units comprise substantially ((CH
3
)
2
SiO) units. In yet another preferred embodiment, the (R
2
SiO) units comprise (CH
3
RSiO) units and (CH
3
ZSiO) units, wherein R is as defined above and Z denotes an organic group with 10 to 30 carbon atoms. In yet another preferred embodiment, the (R
2
SiO) units comprise substantially (CH
3
ZSiO) units,
wherein Z=an organic group with 10 to 30 carbon atoms.
In yet another embodiment of the invention, the copolymers have the structure
R
2
X Si—O—(R
2
SiO)
q
—(RXSiO)
y
—SiXR
2
  VI
wherein R, X, q and y are as defined above. In a preferred embodiment, a majority of the R groups are methyl and X is polyisobutylene. In another preferred embodiment, the (R
2
SiO) units comprise (CH
3
RSiO) units, wherein R is as defined above. In yet another preferred embodiment, the (R
2
SiO) units comprise substantially ((CH
3
)
2
SiO) units. In yet another preferred embodiment, the (R
2
SiO) units comprise (CH
3
RSiO) units and (CH
3
ZSiO) units, wherein Z=an organic group with 10 to 30 carbon atoms. In yet another preferred embodiment, the (R
2
SiO) units comprise substantially (CH
3
ZSiO) units, wherein Z=an organic group with 10 to 30 carbon atoms.
The above copolymers are made by reactin

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