Polymer compounds containing oxetane and cinnamyl functionality

Details Polymer compounds containing oxetane and cinnamyl functionality Polymer compounds containing oxetane and cinnamyl functionality

2005-09-13

2005-09-13

Choi, Ling-Sui (Department: 1713)

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C526S335000, C526S348000, C526S317100, C526S343000, C526S344000, C526S341000, C526S319000

Reexamination Certificate

active

06943258

ABSTRACT:
These compounds contain an oxetane functionality and a cinnamyl functionality. The oxetane functionality is homopolymerizable in reactions that can undergo cationic or anionic ring opening, and the cinnamyl functionality is polymerizable with compounds such as electron acceptor compounds. The dual functionality allows for dual cure processing. The generic structure of such compounds isin which R is a methyl or ethyl group, X and Y independently are a direct bond, or an ether, ester, or carbamate group, and Q is a divalent hydrocarbon (which may contain heteroatoms of N, O, or S), provided that X and Y will not both be direct bonds in the same molecule.

REFERENCES:
patent: 3867353 (1975-02-01), Hsieh et al.
patent: 4225691 (1980-09-01), Crivello
patent: 2002/0089067 (2002-07-01), Crane et al.
patent: 2002/0143112 (2002-10-01), Weinert et al.
patent: 20011329112 (2001-11-01), None
patent: WO 02/28985 (2001-11-01), None
patent: WO 02/06038 (2002-01-01), None
patent: WO 02/06038 (2002-01-01), None
Hsieh, “Terpolymerization of cyclic ethers with cyclic anhydride” J. Macromol. Sci., A7(7), 1525-1535(1973).
Bach, “The Paterno-Buchi reactions of 3-heteroatom-substituted alkenes as a stereoselective entry to polyfunctional cyclic and acyclic molecules”, Liebigs Annalen: Organic and Bioorganic Chemistry, 1627-1637(1997).
Bach et al., “Synthesis of syn- and anti-1,2-amino alcohols by regioselective ring opening reactions of cis-3-aminooxetanes”, Tetrahedron Letters, 38(21), 3707-3710(1997).
Meijer et al., “Chiralitat nur im angeregten Zustand”, Angew. Chem., 100(7), 1004-1005(1988).
Singha etal. transfer radical copolymerization (ATRCP) of a monomer bearing an oxetane group, Polymer Preprints, 43(2), 165(2002).
Ledwith, Anthony: “Possibilities for promoting cationic polymerization by common sources of free radicals”;Polymer,vol. 19; pp. 1217-1222, Oct. 1978.
Sasaki, Hiroshi et al.: “Photoinitiated Cationic Polymerization of Oxetane Formulated with Oxirane”;Journal of Polymer Science Part A; vol. 33; pp. 1807-1816, 1995.
Searles, Scott et al.: “Hydrogen Bonding Ability and Structure of Ethylene Oxides”;This Journal; 2775-2777, Jun. 1953.
Xianming, Hu et al.: “Phase-Transfer Synthesis of Optically Pure Oxetanes Obtained from 1,2,2-Trisubstituted 1,3-Propanediols”;Synthesispp. 533-538, May 1995.
Fujiwara, Tomoko et al.: “Synthesis and Characterization of Novel Oxetane Macromonomers”;Polymer Preprints44(1), 785, 2003.
Dhavalikar, R. et al.: “Molecular and Stuctural Analysis of a Triepoxide-Modified Poly(ethylene terephthalate) from Rheological Data”;Journal of Polymer Science: Part A: Polymer Chemistry; vol. 41, 958-969 (2003).
Satoh, Toshifumi et al.: “A Novel Ladder Polymer. Two-Step Polymerization of Oxetanyl Oxirane Leading to a “Fused 15-Crown-4 Polymer ” Having a High Li+-Binding Ability”;Macromolecules, 36, 1522-1525, 2003.
Chen, Yu et al.: “Synthesis of Multihydroxyl Branched Polyethers by Cationic Copolymerization of 3,3-Bis(hydroxmethyl)oxetane and 3-Ethyl-3-(hydroxymethyl)oxetane”;Journal of Polymer Science: Part A: Polyme Chemistry, vol. 40, 1991-2002.
Nishimura, Tomonari et al.: “Chemoselective isomerization of amide-substituted oxetanes with Lewis acid to give oxazine derivatives or bicyclic amide acetals”;Chem. Commun., pp. 43-44, 1998.
Miwa, Yoshiyuki et al.: “Polymerization of Bis-Oxetanes Consisting of Oligo-Ethylene Oxide Chain with Lithium Salts as Initiators”; Polym. J., vol. 33, No. 8, pp. 568-574, 2001.
Ichikawa, Eiko et al.: “Synthesis of Oxetanocin A and Related Unusual Nucleosides with Bis(hydroxymethyl)-branched Sugars”;Synthesis 2002, No. 1, Dec. 28, 2001; Georg Thieme Verlag Stuttgart, NY; pp. 1-28.
Minegishi, Shouji et al.: “Synthesis of Polyphosphonates Containing Pendant Chloromethyl Groups by the Polyaddition of Bis(oxetanes)s with Phosphonic Dichlorides”;Journal of Polymer Science: Part A: Polymer Chemistry, vol. 40 3835-3846; 2002.
Sasaki, Hiroshi et al.: “Photoinitiated Cationic Polymerization of Oxetane Formulated with Oxirane”;Journal of Polymer Science: Part A: Polymer Chemistry, vol. 33, 1807-1816; 1995.
Rosenbaum, Dr. Barry et al.: “Develop Better Coatings”;OMNOVA Solutions Inc., Akron, OH; pp. 1-5, Dec. 2002.
Sasaki, Hiroshi: “Application of Oxetane Monomers for UV-Curable Materials”; RadTech 2002; Tech. Conf. Proceedings; pp. 64-78, 2002.
Carter, Wells et al.: “New Oxetane Derivative Reactive Filuent for Cationic UV Cure”;RadTech 2000; Tech. Proceed.; pp. 641-649, 2000.
Crivello, J. V. et al.: “Diaryliodonium Salts as Thermal Initiators of Cationic Polymerization”;Journal of Polymer Science: Polymer Chemistry Ed, vol. 21, 97-109 (1983).
Lu, Yong-Hong et al.: “Synthesis of Side-Chain Liquid Crystalline Polyoxetanes Containing 4-(Alkanyloxy)phenyltrans-4-Alkylcyclohexanoate Side Groups”,Macromolecules, pp. 1673-1680, 1995.
Lu, Yong-Hong et al.: “Synthesis of side-chain liquid crystalline polyoxetanes containing 4-dodecanyloxphenyltrans-4-alkylcyclohexanoate side groups”;Polymer Bulletin 32, 551-558 (1994).
Hsu, Li-Ling et al.: “Studies on the Synthesis and Properties of Ferroelectric Side Chain Liquid Crystalline Polyoxetanes”;Journal of Polymer Science: Part A: Polymer Chemistry; vol. 35, 2843-2855; (1997).
Kawakami, Yusuke et al.: “Synthesis and Thermal Transition of Side-chain Liquid Crystalline Polyoxetanes Having Laterally Attached Mesogenic Group”;Polymer International; 31, 35-40 (1993).
Kawakami, Yusuke et al.: “Synthesis of Liquid Crystalline Polymers with a Polyoxetane Main Chain”;Macromolecules; vol. 24, No. 16, pp. 4531-4537, 1991.
Kawakami, Yusuke et al.: “Srnectic liquid crystalline polyoxetane with novel mesogenic group”;Polymer Bulletin 25; Springer-Verlag 1991; pp. 439-442.
Crivello, J.V. et al.: “Photoinitiated Cationic Polymerization With Multifunctional Vinyl Ether Monomers”;Journal of Radiation Curing, Jan. 1983; pp. 6-13.
Ishizone, Takashi et al.: “Protection and Polymerization of Functional Monomers. 29. Syntheses of Well-Defined Poly[(4-vinylphenyl)acetic acid], Poly[3-(4-vinylphenyl)propionic acid], and Poly(3-vinylbenzoic acid) by Means of Anionic Living Polymerizations of Protected Monomers Bearing Bicyclic Ortho Ester Moieties”;Macromolecules, 32, 1453-1462, 1999.
Sato, Kazuya et al.: “New Reactive Polymer Carrying a Pendant Oxetane Ring”;Macromolecules, 25, 1198-1199; 1992.
Moussa, K. et al., “Light-Induced Polymerization of New Highly Reactive Acrytic Monomers”;Journal of Polymer Science: Part A: Polymer Chemistry, vol. 31, 2197-2203 (1993).
Kawakami, Yusuke et al.: “Synthesis of Liquid Crystalline Polyoxetanes Bearing Cyanobiphenyl Mesogen and Siloxane-Containing Substituent in the Repeating Unit”;Polymer Journal, vol. 28, No. 10, pp 845-850 (1996.).
Crivello, J. V. et al.: “Synthesis and Photopolymerization of Silicon-Containing Multifunctional Oxetane Monomers”;J.M.S.-Pure Appl. Chem., A30(2 & 3), pp. 173-187 (1993).
Chappelow, C. C. et al.: “Photoreactivity of Vinyl Ether/Oxirane-Based Resin Systems”;Journal of Applied Polymer Science, vol. 86, 314-326 (2002).
Toagosei Co. Ltd.: “Developing Monomers”.
“Oxetane”; Copyright 2000 American Chemical Society.
Hou, Jian et al.: “Synthesis of a Star-Shaped Copolymer with a Hyperbranched Poly(3-methyl-3-oxetanemethanol) Core and Tetrahydrofuran Arms by One-Pot Copolmerization”;Macromol. Rapid Commun. 2002, 23, 456-459.
Xu, Jun et al.: “On Cationic Ring-Opening Polymerization Mechanism of 3-Ethyl-3-Hydroxymethyl Oxetane”;J. Macromol. Sci.-Pure Appl. Chem., A39(5), 431-445 (2002); Marcel Dekker, Inc.
Suzuki, Hiroshi et al.: “Photo-

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