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
1999-09-20
2001-05-01
Seidleck, James J. (Department: 1711)
Synthetic resins or natural rubbers -- part of the class 520 ser
Synthetic resins
Mixing of two or more solid polymers; mixing of solid...
C525S316000, C525S271000, C526S173000, C526S183000, C526S340000, C502S152000, C502S157000
Reexamination Certificate
active
06225415
ABSTRACT:
FIELD OF THE INVENTION
The present invention relates to an improved to form polymers containing functional groups selectively dispersed through out the molecular structure, and the polymers produced by that process.
BACKGROUND OF THE INVENTION
Prior art anionic polymerization processes of conjugated dienes and monoalkenyl arenes are described in U.S. Pat. Nos. 4,039,593 and Re. 27,145, which are hereby incorporated herein by reference. Typical living anionic polymer structures formed using such prior processes include:
R—A—Li
R—A/B—Li
R—A—B—Li
R—A/B—B—Li
R—A—A/B—Li
R—A—B—A—Li
wherein A and B each represent polymerized units of a single anionically-polymerizable monomer, A/B represents random polymerized units of two different anionically-polymerizable monomers, and R is the residue of the lithium initiator.
Use of initiators which include a protected functional group is also known in the art. After polymerization, the protective group can be removed to yield a polymer having a desired terminal functional group. For example, U.S. Pat. No. 5,331,058, incorporated herein by reference, teaches use of an alkyl lithium initiator having a terminal trimethylsilyl group. After the anionic polymerization is complete, the trimethylsilyl group can later be removed leaving a hydroxy-terminated hydrocarbon polymer.
This prior art technology, however, only allows incorporating functionally at the terminus of the polymer chain. Copolymerization of monomers having protected functional groups leads to a random distribution of such functionality throughout the polymers formed.
Applicant's novel process, however, allows more precise placement of protected functionality along the molecules structure of a hydrocarbon polymer. Therefore, the molecular weight between such functional groups can be better controlled to form more useful polymeric materials.
SUMMARY OF THE INVENTION
Applicant's novel process involves sequentially polymerizing conjugated dienes and/or monoalkenyl arenes to form a first anionically terminated living polymeric segment. This first living polymeric segment can comprise a homopolymer, a random copolymer, or a block copolymer. A single unit of structure I or II is then added to form a second living polymer.
wherein R
1
is H or alkyl, n is 1 to 5, and G is an electron donating chemical moiety, such as those moieties which include hetero atoms containing one or more pairs of unshared electrons. For example, G can be selected from the group consisting of —O—CH
3
, —O—CH
2
—O—CH
3
, —O—CH
2
—Phenyl, —S—CH
3
, —CH
2
—O—CH
3
, —CH
2
—N(CH
3
)
2
, and —O—CH
2
—CH═CH
2
. As those skilled in the art will appreciate, G comprises a protected functional group.
A second monomer is then added to the second living polymer to form a third living polymer. The second polymer segment formed can comprise a homopolymer, a random copolymer, or a block co-polymer. This second polymeric segment may be identical to the first polymeric segment, or it may differ in composition and/or molecular weight.
In a first embodiment, the third living polymer may be quenched with a proton donor. In another embodiment, this third living polymer can be reacted with one of various coupling agents to form a linear polymer, a three arm radial polymer, or a four arm radial polymer.
In yet another embodiment, another single unit of compound I or compound II can be added to the third living polymer to form a fourth living polymer. The second incorporated protected functional group may be the same as the first such incorporated functional group, or it may comprise a different protected functional group. In another embodiment, the fourth living polymer can be quenched with a proton donor.
In an alternative embodiment, a third monomer can be added to the fourth living polymer to form a fifth living polymer which includes a third polymeric segment. This third polymeric segment can be identical to the first polymeric segment and/or the second polymeric segment, or it may differ from both the first and second segments in composition and/or molecular weight.
The fifth living polymer can be quenched or reacted with various coupling agents to form various linear polymers, a three arm radial polymer, or a four arm radial polymer.
REFERENCES:
patent: Re. 27145 (1971-06-01), Jones
patent: 3244664 (1966-04-01), Zelinski et al.
patent: 3281383 (1966-10-01), Zelinski et al.
patent: 4039593 (1977-08-01), Kamienski et al.
patent: 4185042 (1980-01-01), Verkouw
patent: 4311818 (1982-01-01), Sigwalt et al.
patent: 4584346 (1986-04-01), Kitchen
patent: 5306314 (1994-04-01), Cherpeck
patent: 5306315 (1994-04-01), Cherpeck
patent: 5306316 (1994-04-01), Cherpeck
patent: 5331058 (1994-07-01), Shepherd et al.
patent: 5346956 (1994-09-01), Gnanou
patent: 5486568 (1996-01-01), Bening et al.
patent: 5545691 (1996-08-01), Bening et al.
patent: 5677387 (1997-10-01), Bayard et al.
patent: 5681895 (1997-10-01), Bening et al.
patent: 5686534 (1997-11-01), Bayard et al.
Xudong Wei and Richard J. K. Taylor, “Organolithium additions to styrene derivatives—III. Enantioselective routes to 2-arylalkanoic acids”, 1997, pp. 665-668.
Asinovsky Olga
Hayes, Soloway, Hennessey Grossman & Hage, P.C.
Seidleck James J.
University of North Carolina at Charlotte
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