LIQUID CRYSTALLINE POLYMER FILMS OF POLYMERS OF HAVING...

Details LIQUID CRYSTALLINE POLYMER FILMS OF POLYMERS OF HAVING... LIQUID CRYSTALLINE POLYMER FILMS OF POLYMERS OF HAVING...

2003-03-24

2004-07-20

Zalukaeva, Tatyana (Department: 1713)

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

Synthetic resins

Polymers from only ethylenic monomers or processes of...

C564S330000, C564S331000, C534S558000, C534S649000, C568S629000, C568S630000, C526S318100, C526S326000, C526S327000, C526S330000, C526S334000

Reexamination Certificate

active

06765079

ABSTRACT:

FIELD OF THE INVENTION
The present invention relates to liquid crystalline polymer films prepared from polymers of novel monomers having azobenzene mesogenic groups and supported in cross linked network structures. The present invention also relates to processes for the preparation of such polymer films. The present invention also relates to polymers of novel monomers having azobenzene mesogenic groups and processes for the preparation thereof, and to polymers prepared from such novel monomers. More particularly, the present invention relates to processes for the preparation of 4-[(4-cardanyl) azo] benzoic acid and its acryloyl derivative 4-[(4-acryloylcardanyl) azo] benzoic acid and their respective polymers poly 4-[(4-cardanyl) azo] benzoic acid and poly 4-[(4-acryloylcardanyl) azo] benzoic acid and includes a process for the cationic polymerisation of 4-[(4-cardanyl) azo] benzoic acid.
4-[(4-cardanyl azo] benzoic acid and 4-[(4-acryloylcardanyl azo] benzoic acid of formulae I and II are novel monomers having azobenzene mesogen. Poly 4-[(4-cardanyl) azo] benzoic acid and poly 4-[(4-acryloylcardanyl) azo] benzoic acid of formulae III and IV are their respective liquid crystalline polymers having azobenzene mesogen supported in a cross linked network structure. The cationic polymerisation of 4-[(4-cardanyl) azo] benzoic acid also gives rise to another liquid crystalline polymer of formula V. These compounds are prepared from inexpensive naturally occurring materials such as cashew nut shell liquid and its distillation product cardanol.
BACKGROUND OF THE INVENTION
Liquid crystalline (LC) polymers with cross linked networks are becoming attractive due to possibilities for freezing the LC phase (Shiota, A. and Ober, C. K.
Prog. Polym. Sci.,
1997, 22, 975; Morman, W. and Zimmermann, J. G.,
Macromolecules,
1996, 29, 1949; Morman, W.,
Trends in Polymer Science,
1995, 2(8), 2559; Koner, H. And Ober, C. K.,
Polym. Mater. Sci.Eng. Prepr.,
1995, 73, 456; Morman, W. and Zimmermann, J. G.,
Macromol. Symp.,
1995, 93,96; Wang, Y. H., Hong, H. L., Yang, F. S. and Hong, I. L.,
Polym. Mater. Sci.Eng. Prepr.,
1994, 71, 678; Melissaris, A. P., Sutter, J. K., Litt, M. H, Scheiman, D. A. and Scheiman, M.,
Macromolecules,
1995, 28, 860; Hoyt, A. E. and Huang, S. J.
J. Macromol. Sci.: Pure Appl. Chem.,
1995, A32,1931; Hikmet, R. A. M., Lub, J. and Tol, A. J. W.,
Macromolecules,
1995, 28, 3313; Lai, W. W. and Chang, T. C.,
J. Polym. Sci., Polym. Chem. Ed.,
1995, 33, 1075; Douglas, E. P., Langlois, D. A. and Benicewice, B. C.,
Chem. Mater.,
1994, 6,1295; Mallon, J. J. and Adams, P. M.
J. Polym. Sci., Polym. Chem. Ed.,
1993, 31, 2249; Barclay, G. G. and Ober, C. K.,
Prog. Polym. Sci.,
1993, 18, 899; Navarro, F.,
Macromolecules,
1991, 24, 6622; Peter, K. and Ratzsch, M.,
Macromol. Chem.,
1990, 191, 1021; Taroze, R. V., Gubina, T. I., Shibaev, V. P., Plate, N. A., Pakin, V. I., Shamakova, N. A. and Shukov, F.,
Macromol. Chem. Rapid Commun.,
1990, 11, 67; Mitchel, G. R., Davis, F. J. and Ashman,
Polymer,
1987, 28, 639: Zentel, R. and Reckert, G.,
Macromol. Chem.,
1986, 187, 1915; Finkelmann, H., Kock H. J. and Rehage, G.,
Macromol. Chem. Rapid Commun.,
1981, 2, 317; Percec, V. (Ed), Liquid Crystalline Polymers, Parts 1-4,
Prog. Polym. Sci.,
1997, 22). These cross linked polymers pass through a mesophase during curing and retain a mesophase in the final state (Shiota, A. and Ober, C. K.
Prog. Polym. Sci.,
1997, 22, 975). By combining the ability to lock in an ordered network structure with the ability to macroscopically align the network, these materials can be used for preparation of films and bulk materials where highly ordered structures can be obtained. LC main chain/side chain polymers with cross linked networks can be prepared by chemical/thermal/photo-cross linking of reactive double bonds in the chain or by reaction with a cross linking agent or by copolymerisation (Morman, W. and Zimmermann, J. G.,
Macromolecules,
1996, 29, 1949; Koner, H. And Ober, C. K.,
Polym. Mater. Sci.Eng. Prepr.,
1995, 73, 456; Wang, Y. H., Hong, H. L., Yang, F. S. and Hong, I. L.,
Polym. Mater. Sci. Eng. Prepr.,
1994, 71, 678). Thus, investigations on a number of rigid rod liquid crystalline thermosets such as blacetylene rigid rod thermosets (Shiota, A. and Ober, C. K.,
Prog. Polym. Sci.,
1997, 22, 975; Melissaris, A. P., Sutter, J. K., Litt, M. H., Scheiman, D. A. and Scheiman, M.,
Macromolecules,
1995, 28, 860; Douglas, E. P., Langlois, D. A. and Benicewice, B. C.,
Chem. Mater.,
1994, 6, 1295), cyanate ester rigid rod thermosets (Barclay, G. G. and Ober, C. K.,
Prog. Polym. Sci.,
1993, 18, 899), rigid rod epoxy thermosets (Carfagna, C., Amendola, E., Giaberini, M., Filiprov, A. G. and Bauer, R. S.,
Liq. Cryst,
1993, 13, 571; Dhein, R., Meier, H.-M., Muller, H.-P. And Gipp, R., German Offen 3622613, A1, 1988; Earls, J. D. and Hefner, R. E., Jr., Eur. Patent Appl. 379057, A2, 1990; Hefner, R. E., Jr. and Earls, J. D., Eur. Patent Appl. 475238, A2, 1992; Eirchmeyer, S., Muller, H.-P. and Karbach, A., Eur. Patent Appl. 445401, A2, 1991), bismaleimide rigid rod thermosets (Hoyt, A. E. and Huang, S. J.
J. Macromol. Sci.: Pure Appl Chem.,
1995, A32, 1931) and semirigid rod liquid crystalline thermosets (Shiota, A. and Ober, C. K.
Prog. Polym. Sci.,
1997, 22, 975; Hikmet, R. A. M., Lub, J. and Tol, A. J. W.,
Macromolecules,
1995, 28, 331) were reported. All these polymers employ the conventional networking using a multiple epoxy grouping or a diacetylene moiety or diacrylate moiety. No report on the formation of cross link through a side chain containing multiple double bonds could be found in patent literature or publications on cross linked liquid crystalline polymers. However, the side chain of cardanyl acrylate has been reported to be used in cross link formation in poly(cardanyl acrylate) which is not liquid crystalline (John, G. and Pillal, C. K. S.,
Macromol. Chem. Rapid Commun.
1992, 13, 255; John, G. and Pillal, C. K. S.,
J. Polym. Sci,Polym. Chem.,
1993, 31, 1069; Pillal, C. K. S., in
Handbook of Engineering Polymeric Materails,
(Ed) N. P. Cheremisinoff, Marcel Dekker, New York (1997). Cardanol is a naturally occurring material and hence is inexpensive. The formation of the cross-linked polymer has been explained as due to the autocross linking of the unsaturated side chain of cardanyl unit (John, G. and Pillai, C. K. S.,
J. Polym. Sci,Polym. Chem.,
1993, 31, 1069). This property of the cardanyl side chain can be used to form cross linked network structures for liquid crystalline polymers. Cardanol was shown to possess special structural features that allow it to be transformed into high performance polymers including liquid crystalline polymers (Pillal, C. K. S., Sherrington, D. C. and Sneddon, A.,
Polymer,
1992, 33, 3968; Saminathan, M., Pillai, C. K. S. and Pavithran, C.,
Macromolecules,
1993, 265 7103; Pillal, C. K. S., Sherrington, D. C. and Sneddon, Indian Patent Application No. 679/Del/92 dated Jul. 29, 1992; Saminathan, M. Pillal, C. K. S. and Pavithran, Indian Patent Application No. 2791/Del/92 dated Dec. 31 1992; Saminathan, M. , Pillal, C. K. S. and Pavithran, Indian Patent application No. 2972/Del/92 dated Dec. 31, 1992. In an earlier patent (Saminathan, M., Pillal, C. K. S. and Pavithran, C., Indian Patent Application No.2972/Del/92 dated Dec. 31, 1992), it was shown that a liquid crystalline polymer, poly[4-[hydroxy-2-pentadecyl)azo]benzoic acid] can be prepared from 3-n-pentadecyl phenol, the hydrogenated derivative of cardanol and that this polymer is potentially a non-linear optical (NLO) material (Saminathan, M., Pillai, C. K. S. and Pavithran, C.,
Macromolecules,
1993, 26, 7103). Azobenzene derivatives and polymers containing donor-acceptor groups in conjugation are known for their NLO activity (Sudesh Kumar, G.,
AZO Functional Polymers: Functional Group Approach in Macromolecular Design
, Technomic Pu

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