Conductive Pyrrolidone Polymers

Acetylenic bis- derivatives of amides can be polymerized to form polyunsaturated lactam polymers that should be new conductive polymers.

Nicotinamide riboside NMN Congeners

MNM is a supplement recommended by Prof. Sinclair, one of the foremost human aging experts, on how to reverse its effects. Looking at the structure of NMN, I have proposed several related congeners. Possibly they might exhibit superior activity?

Reduction of Polysuccinimide

Polysuccinimides are readily available from the polymerization of inexpensive maleic anhydride and ammonia. I propose that they can be reduced to polypyrrolidone backbone polymers with the new hydrogenation catalysts.

Unsaturated Cyclic Lactam Polymers

Polyacetylenes are unsaturated polymers of great interest as conductive materials. Other analogous unsaturated related polymers can be prepared by cyclopolymerization, a subset of matathesis polymerization. I present several proposals for consideration.

ROMP of Unsaturated Small Cyclics

Will 3-Pyrrolin-2-ones or larger lactam congeners undergo the ROMP resulting in unsaturated polyamides that could react with dienophiles?

"Vince Lactam" Polymers

Vince lactam can be polymerized by ROMP. Can related bicyclic lactams also be polymerized? I present several new ideas.

Lactam Chain Polymers

Copolymers of N-vinylformamide and (meth)acrylates are alternating. Hydrolysis to the free amine results in the formation of backbone lactams by the attack of the free amine next to acrylate esters. Can this chemistry be expanded?

Captodative 1,1-Vinyl Monomers

Captodative 1,1-Vinyl Monomers contain both electron donating and electron withdrawing substiuents on the same carbon atom. I review this type of acrylate monomer chemistry and offer several new ideas.

Lactam Quaternary Derivatives

Can monomeric or polymeric lactam quat derivatives be superior biocides? Can such compounds also be converted into iodophors resulting in dual biocide capability? I suggest methods to synthesize these compounds.

N-Vinyl Lactam Monomers

Although I have proposed new N-Vinyl Lactam monomers in previous pdf's, A new article concerning this subject renewed my interest. I present a review of their synthesis and several new bicyclic ideas.

DMAEMA vs, DMAEA

In another pdf, I saw a need for DMAEA predicting it would react with terminal Br from ATRP polymerizations but where DMAEMA didn't react. I became interested in further differences between the two. I present a brief report on this subject believing I'm covering the basics in a rather voluminous literature.

ATRP Quats and Polyquats

ATRP places a reactive bromine at the polymer ends. Can this bromine be employed to add terminal quats and polyquats to a wide variety of ATRP generated polymers? I show several ideas to accomplish this chemistry.

Polypyrrolidones and Cyclopolymerization

Cyclopolymerization has been applied to many divinyl monomers but not to pyrrolidone containing monomers. This proposal illustrates several approaches to cyclopolymerizable pyrrolidone containing monomers and their corresponding polymers. Which ideas are feasable I will leave that to the readers.

2,5-Diketopiperazine Polymers

2,5-Diketopiperazine polymers can be visualized as a combination of n-methyl pyrrolidone super solvent and polyvinylpyrrolidone complexing polymers, Please read my pdf to see why I claim these attributes for these polymers!

The Castagnoli-Cushman Polymerization Reaction

The Castagnoli-Cushman Reaction to my knowledge has never been employed to synthesize polymers. This is a proposal concerning synthesis schemes to use the CCR to generate polymers. In the literature, examples are revealed that the neat CCR reactions can take place in a minute or less. This reaction even in solvents is very fast. CCR polymer components could be painted on biological surfaces after mixing and then would fill all the cracks and crevices. If a CCR designed polymeric adhesive could be used medicinally to bind wounds and bones etc. and because of its fast polymerization it might be of low toxicity or non-toxic.

Polyester Containing Pyrrolidones

I propose the synthesis of pyrrolidone polyesters that would have the unique properties of pyrrolidones like PVP but are water soluble and hydrolizable. Such polyesters would conceivably be non-toxic and easily excreted after delivering medicinals,.

New Pyrrolidone Vinyl Monomers

I'm suggesting both new and interesting pyrrolidone existing monomers that can be polymerized by free radical initiators.
Because PVP is of major commercial importance, I think that new monomers related to vp would be of interest.

Vinylcyclopropane Pyrrolidone Polymers

Can VCP be combined with the pyrrolidone functionality? Several possible examples that appear possible are proposed.

s-Tetrazine Containing Beads for the Capture of Cancer Cells

I'm proposing that such beads(organic polymer supported resins) can be functionalized with s-tetrazines which can react with monoclonal antibodies derivatized with fast inverse electronic demand dienophiles attached to said monoclonal antibodies in analogy with the attachment of Antibody Drug Conjugates(ADC). Furthermore, cancer cells in blood (plasma cells) can then be filtered out.

Polymeric Inverse-Electron-Demand Diels-Alder Reactions

This proposal suggests several possible polymeric IEDA
reactions based on tetrazine and pyridazines intermediates

s-Tetrazine polymers

I have found no references to polymers that have s-tetrazine in the polymer backbone. I suggest a couple of ideas for preparing them and also include some proposals for cyclophanes based on iEDDA chemistry.

Review of tetrazine synthesis

After searching the literature for another proposal, I thought that a brief summary of tetrazine synthesis would be of value.

Reversible Diels-Alder Reactions of Acenes

Acenes are unstable but when the aromaticity is interrupted with a Diels-Alder adduct then they can be relatively easily handled . The original Acene can be obtained by employing the reverse DA reaction. Such stabilized Acenes can then be polymerized as vinyl derivatives and recovered by the rDA reaction.

Polyazoaromatics

How do you hook-up polyaromiatics like anthracene to obtain cis trans isomerism with azo linkages? Symmetry allowed or forbidden connections answers this question. Polymers based on these ideas are suggested.

N-Vinylpyrrole

Can N-Vinylpyrrole be oxidised to N-Vinyl-3-pyrrolin-2-one and subsequently reacted with iodine to form a new iodophor?

Vinyl Imide and Vinyl Aromatic Monomers and Polymers

Unique polyaromatic vinyl monomers are proposed with various applications suggested. Much of the pertinent literature is reviewed. Vinyl Imide and Vinyl Aromatic Monomers and Polymers

Quality parameters for sodium cocoyl isethionate

Although this review is dated, it is still of interest in my opinion. I'm posting it because it was published in a journal that isn't readily available. I see that sodium cocoyl isethionate has thousands of hits on Google Scholar indicating the high level of interest. I hope you find this of value.

Epoxylactams

3,4 epoxypyrrolidones can be readily prepared. Several potential new synthesis and applications such as polymeric derivatives are disclosed. Take a look at this interesting chemistry.

Potential "Vinyl" Lactam Monomers.

Why are cyclic monomers rare for vinyl free radical polymerization. How many regular non-cyclic monomer structures can also be suggested?

3-Pyrrolidinylcarboxylic acids(PCA)

3-methylene-2- pyrrolidone(3M2P) I believe is a vinyl monomer that has great potential applications. Its problem is cost to manufacture on an industrial scale. I propose Rapoport's rearrangement of PCA as a inexpensive synthesis of this monomer.

3-Methylene-2-Pyrrolidone(3M2P) and Related Monomer Chemistry

3M2P and related monomers could be commercial successes if a cost effective synthesis were known. A review of their synthesis and several ideas are presented.

C1 Polymerization of Pyrrolidone Derivatives

C1 polymerization can put a pyrrolidone on every backbone carbon unlike vinyl polymerization which alternates backbone carbons. Is a more densely derivatized PVP polymer superior in complexing iodine, for example.

Tropone, Tropolone and Azulene ImiD (Immunomodulatory imide drug) Analogs

Tropone, tropolone and azulene can be the basis for new ImiD anti- cancer compounds. Several ideas are presented including suggested synthesis.

Tropone and Tropolone Chemistry

What follows are excerpts from references I was able to obtain dealing with aspects of this chemistry. I'm doing this as a service to those who are interested in this subject.

Azulene Chemistry

What follows is a summary of the synthesis reactions related to Azulene, its generation and its derivatives based on the references I was able to review. I hope that this summary will be of help to those who might be interested in this subject.

Poly(Lenalidomides and Pomalidomides)

My thinking is to employ acid labile linkages to cross-link thalidomide analogs so that they would initially be nontoxic but in acidic cancer cells, would result in their hydrolysis to the active drug.

Bergman Cyclization Cascade Reaction Polymerizations

It is known to use the diradical intermediates in cascade reactions but can they also be used to generate polymers? I present several proposals to do just that.

Bergman Cyclization 1,8-Napthalimide Derivatives

My proposal is to derivatise 1,8-napthalimides or derivatives thereof, coupled with enediynes such that said conjugated compounds would fatally damage cancer cell DNA and associated proteins.

Bergman Cyclization based Acenes, Polyacenes and PDI derivatives

Using readily available RM's, a method to employ the BC at lower temperatures that would not damage a substrate, possible singlet fission and semiconductors active compounds are proposed.

Bergman Cyclization Thalidomide Precursors

Can cancer survival proteins be attacked and degraded by Bergman Cyclization(BC) enediynes generated thalidomide precursors? I propose several possible structures that undergo the BC reaction to form a warhead diradical that after it damages said survival proteins turns into a thalidomide analog to then function as an IMid to use the UPS system to further damage the cancer cell.

Thalidomide Analogs

Thalidomide analogs are currently the basis for treating multiple myeloma but can new analogs be conceived of that might work more effectively? I propose several new ideas.

Xylylene Crosslinked Polymers

The Winberg cyclization and the Gilch reaction have been used to prepare Xylylene unsaturated polymers. I propose that the same reactions can be employed to crosslink organic semiconductors retaining their unsaturated structure.

[2,2]Paracyclophane and Singlet Fission

Homoconjugation is associated with improved SF; however, [2,2]Paracyclophanes can be considered a type of homoconjugation and should also work to generate highly active SF. Winberg cyclization and the Gilch reaction can produce [2,2]Paracyclophanes in modest yields with the major product being the polymer. Can said polymer also support SF?

[2+2+2] Cycloaddition Polymers

Trans metal catalyzed aromatic synthesis is an elegant method of producing complicated derivatives but has been less employed to prepare polymers. Several proposals to polymer synthesis are suggested.

Indane-1,3-dione Based Vinyl and Alkyne and Singlet-Fission based Polymers

Starting first with vinyl and alkyne polymeric indane-1,3-diones and then describing a variety of Singlet Fission possibilities, a variety of new OPV ideas are proposed.

Downloadable file concerning PVP chemistry

Pyrrolidone Derivatized Organic Semiconductors

Currently OPV's suffer from poor solubility in safe solvents such as water and alcohols. I believe that pyrrolidone derivatives could solve this problem. The pyrrolidone moiety is a planer five membered ring allowing maximum orbital over lap of the lactam resonance structures, one of which is zwitterionic. Thus affording solubility in polar solvents.

Polymeric Organic Solar Cells

DCI terminals of ITIC type organic solar cell(OSC) acceptors can be linked together to generate dimers, oligomers and polymers that could increase PCE's in all polymer OSC's. Various imide derivatised DCI's are also proposed that take advantage of PDI chemistry and can also be readily polymerized. In both cases said polymers can be prepared with both donor or acceptors or combinations. This might be an approach to single material organic solar cells.

Inexpensive FeCl3 Oxidative Polymerizations

FeCl3 can be regenerated with H2O2 in water so that small amounts can be used. What is needed is an organic oxidant that is solvent soluble so that this cost effective polymerization technique can be employed with a variety of organic semiconductor monomers. This would avoid highly toxic catalysts and multi-step polymerizations.

Review of the oxidative polymerization of phenylene diamines

I have published two proposal pdf's on my web page concerning the synthesis of pyrazine containing polymers. For completeness, I thought this chemistry would be of interest.

Alternating Pyrazine Organic Semiconductor Polymers

Organic semiconductor synthesis intermediates can readily be derivatized with alkyne terminals, converted to haloalkynes and then to alpha amino ketones with high yield well known reactions. The alpha amino ketones can form pyrazines and with difunctional intermediates, alternating pi conjugated polymers

Claisen-Schmidt(C-S) Condensation Based Organic Semiconductor Polymers

The Claisen-Schmidt condensation is between aromatic aldehydes and methyl ketones. Functional groups that can be readily attached to aromatic organic semiconductor intermediates by the Vilsmeir and Sonogishira (acetylene to ketone) reactions. This leads to new polymers with potentially unique semiconductor properties.

Polydiacetylene Organic Semiconductors

Numerous references have appeared concerning the synthesis and utility of polydiacetylenes(PDA's) but few if any indicate possible approaches to their use in organic semiconductors.

Crosslinkable 3,4-Furan containing Organic Semiconductors

???Organic solar cells (OSCs) have achieved much attention and meanwhile reach efficiencies above 10%. One problem yet to be solved is the lack of long term stability. Crosslinking is presented as a tool to increase the stability of OSCs." My proposal presents several new crosslinking mechanisms.

Polymeric Isoindigo, benzodifurandione and benzodipyrrolediones

Isoindigos and related compounds in a polymeric motif should be excellent electron acceptors for n-organic semiconductors. Several ideas for their synthesis are proposed.

Pechmann Dye Homopolymers

Related to isoindigo, DPP etc., Pechmann dyes are another unique class of organic semiconductor lactam containing components. Proposals for the synthesis of polymeric versions are presented. These polymers are potentially very active acceptors and therefore would have interesting OSC properties. A detailed review of the synthesis of Pechmann dyes is also included.

Synthesis of Separated DPP, DPP and ISODPP Derivatives

Proposals for new organic electronic active compounds. Synthetic routes to each type are proposed. These ideas could lead to a variety of new OPV, OFET, OSC,OLED etc actives. This is my search for new more effective materials that can be used in these applications.

DPP analogs based on Alpha-Amino Ketones

Alpha-Amino Ketones can react with succinate esters to afford monomeric and polymeric analogs of DPP. Such analogs would be competitive semiconductors with improved properties outside of current DPP patent claims.

New Boronate Monomers and Polymers

Boronic acid reactions with cyclic diols (sugars-glucose) are very important medical indicators. I illustrate several new approaches to this chemistry including how to prepare 3,4 dihydroxypyrrolidones.

Alpha-Amino Ketone based Polymeric Pyrazines

Alpha-amino ketones available from the Neber rearrangement and other reactions can be employed to prepare unique polypyrazines useful in semiconductor applications.

New rROP Monomers for the Synthesis of Polyanhydrides

New monomers that can generate polyanhydrides by radical ring opening polymerization are presented. They would afford readily degradable plastics and others would afford unique post polymerization reaction possibilities.

Radical Ring Opening Polymerization of Lactam Monomers

Lactams can be employed to derivatize rROP monomers so that polymers containing degradable ester groups can be prepared. Analogs to PVP that are degradable are proposed.

Antibiotic Lactam Monomers and Polymer Sequestrants

New ideas for Antibiotic lactam monomers forming polymer ingredients based on hydroxamic acids, catechols, edta analogs and nitric oxide donors designed to stop siderophores from stealing iron.

Multicomponent Reactions(MCR) of Pyrrolidone and PVP Derivatives

Novel and new Ugi and Passirini multicomponent reactions of Pyrrolidone and PVP derivatives are presented.

Diels-Alder Reactions of Furan

Several ideas concerning the Diels-Alder reactions of Furans to produce Healable polymers, formation of new degradable polyesters and unique polyamides are presented.

Phosphorus Containing Specialties

Caprolactone or lactams containing a phosphorus moiety are interesting ROP monomers. Polymerizable cyclic phosphonates in a polymer backbone can be post polymerized to yield hydrogels useful for drug delivery.

PVP Derivatives

PVP and related polymers can be reduced or oxidized or derivatized with CTA's for RAFT/MADIX copolymerization or converted to thiolactams.

Sulfur, Phosphorus or Silicone Containing Lactams

What are the results of replacing a lactam ring carbon with sulfur or phosphorus or silicone?

US 2016/0355616 Polyvinylpyrrolidone Analog Polymers

Dimer vinylpyrrolidones are polymerized with anhydrous HBr or ADMET to form polymers that can be degraded in acidic aqueous solution but are stable when such solutions are at basic pH. US 2016/0355616 is now pending.

Cyclic RAFT/MADIX CT Agents

Oxiranes react with CS2 to yield 1,3-oxathiolane-2-thiones. Can these cyclic xanthates work as MADIX CTA's to generate cyclic polymers?

MADIX Polymerization of NVP

MADIX Polymerization of NVP in the presence of Anionic Surfactants in order to improve PVP tacticity

Pyrrolidone Aldehyde Derivatives

Pyrrolidone aldehyde derivatives can react with acrylic monomers by the Morita-Baylis-Hilman reaction.

Baylis-Hillman reaction

Can the Baylis-Hillman reaction be modified to work with epoxides to synthesize 3-methylene derivatives of BLO and pyrrolidone?

Nucleobase Peptide Protocells

The combination of nucleobases and peptides in the same compound could solve the problem of why current organisms need both. They could have generated the first protocells.

Silicone-Pyrrolidone Copolymers

Pyrrolidone contributes desirable properties to silicones.

Nucleic Acid Derivatised Pyrrolidone

Nucleic acid derivatised pyrrolidones have value.

Fluorinated Pyrrolidone Compounds

Many useful Fluorinated Pyrrolidone derivatives can be conceived.

Reversibly Cross-Linkable Polymers based on NHC Dimers

The Wanzlick equilibrium can be employed to cross-link polymers containing NHC's.

The Chemistry of Acetylenic Derivatives of Pyrrolidone

A review of monomers and polymers based on acetylenic derivatives.

Poly(NMP) is an example of reverse PVP

NMP is a super solvent that can be conceived of in a polymer format.

New Heterocyclic Monomers and Polymers

New Heterocyclic Monomer and Polymer chemistry is presented including several pro-drug ideas. Five membered rings containing multiple hetero-atoms are described.

Amide-Imide compounds and their corresponding polymers

Without the benefit of a Patent Attorney, I was able to successfully pursue my own patent application. It concerns novel Amide-Imide Compounds and their Corresponding Polymers.

N-Heterocyclic Carbenes based on Pyrrolidone derivatives.

N-heterocyclic carbenes have extremely important applications but none have benefited from pyrrolidone and pyrrolidine chemistry. Several approaches to such NCH's are proposed.

Tartaric acid derivatives

Tartaric acid derivatives are new monomers for free radical ring opening polymerization (RROP).

RCM Metathesis Polyfuranones and Polylactams and dendrimers combined

Metathesis can be employed to prepare a variety of furanones, lactams, polymers and dendrimers(hyperbranched) with a wide variety of applications.

Pyrrolidone analog based Polymers

The pyrrolidone functionality can be manipulated to be in a wide variety of polymers prepared by ATRP, RCM, ADMET, ROMP and other techniques.

Racetams candidates based on 'Pyrrolidone' Dimers

Pyrrolidone has proven to be the basis of the very important racetam drugs to fight dementia, seizures, pain, and hopefully someday Alzheimers. I believe that other five membered pyrrolidone like structures might also show racetam activity and are worth testing.

Pyrrolidone Dimers and Pendant Pyrromethane Polymers with MIP potential

Various methods to synthesize dimer pyrrolidones and pyrromethane polymers, and applications of these unique compounds are suggested.

Porphyrins, Calixpyrroles and Cucurbituril like Macrocyclics containing Pyrrolidone Functionality

Pyrrolidone can be attached to macrocyclics such porphyrins(porphyrinics) calixpyrroles and cucurbituril like compounds . In these large molecules, pyrrolidone can attract a proton to become cationic. This tendency would complex anionic molecules while the pyrrole nitrogens complex cationic molecules. Such multipurpose macrocycles would have many significant applications.

Spiro-bis-cyclohexane-1,3-dione

A unique dimedone spiro dimer can be readily prepared in good yield from inexpensive 2,4-pentanedione and methyl acrylate. It can be employed as a synthon for the preparation of molecules like those numerous examples found for dimedone but as unique spiro dimer derivatives. Medicinal chemist and those interested in new specialty compounds might find significant uses for these spiro-biscyclohexane-1,3-dione derivatives.

Copolymers Prepared by the In-Situ Synthesis of Maleimide/Maleamic Acid Monomers

The reaction of mono primary amines with methyl maleate half ester results in a maleamic monomer containing mixture that can be polymerized in-situ to copolymers containing polymaleimides segments.

The Reaction of PVP with Strong Bases

PVP recently has been shown to gel in the presence of sodium hydroxide. I have discovered three additional ways to use PVP with strong alkali to form waxes, high MW mixtures or stable powders that gel when heated. I proposed a mechanism for these reactions.

Pyrrolidone Backbone Polymers

PVP, one of the most lucrative specialty polymers has dominated its market for eighty years, but is it the best way to obtain it's outstanding properties? Please take a look at my ideas for an improved competitor.

"These failures to remediate these widely recognized deficiencies of commercial PVP were highlighted recently by Login (www.rloginconsulting.com/...pyrrolidone%20backbone%20polymers.pdf) with the suggestion that condensation polymerization strategies be considered for introduction of the highly desirable pyrrolidone ring into the polymer main chain versus the use of free radical polymerization approaches which yield products with the pyrrolidone ring pendant to the main chain."

WO2016040962 A1

Polyspiroimides

The Michael reaction is employed, for example, to condense methyl acrylate with diethyl malonate to prepare the corresponding tetra-ester. Subsequent reaction with primary amines followed by thermal condensation results in spiroimides. A similar series of reaction steps can be performed starting with malonamides.

Degradable Poly(acetal-lactone-ester) Polymers

A process for preparing hydrolytically degradable random terpolymers of poly(acetal-lactone-ester) comprising:
a). mixing glycerol with glyoxylic acid, in essentially equal molar ratios, b). and under means of heat and vacuum sufficient for removal of water of condensation from the reaction mixture.

Polymerization Of Alkyl (beta-n-alkylaminopropionates) Forming Unique Polyamide Compositions

A process for preparing poly N-substituted beta-alanines with the steps of: combining in a Michael reaction approximately 1.0 to 1.2 moles of methyl acrylate with approximately one mole of one or more primary amines to produce an alkyl(beta-n alkylaminopropionate); and heating the alkyl(beta-n-alkylaminopropionate)to a reaction temperature between approximately 100 and 200 degrees C and simultaneously evacuating the alkyl(beta-n-alkylaminopropionate) to 25-30 to remove volatiles, thereby forming a poly N-substituted beta-alanine.