Novel Chain Extenders

Patent Title: METHOD OF PRODUCING FIVE-CARBON RING-CONTAINING COMPOUND AND FIVE-CARBON RING DERIVATIVE-CONTAINING POLYURETHANE, AND FIVE-CARBON RING DERIVATIVE-CONTAINING POLYURETHANE

Number/Link: US2019/0048123

Applicant/Assignee: CHUNG SHAN INSTITUTE OF SCIENCE AND TECHNOLOGY

Publication Date: 14-February 2019

Gist”: Novel chain extenders are derived from dicyclopendadiene (DCPD)

Why it is interesting: DCPD is a by-product of ethylene production by steam cracking of naphta.  It is produced in large quantities and it makes sense to search for new applications.  According to this invention, the compound shown below can be prepared by first ‘degrading’ DCPD to cyclopentadiene, followed by reaction with phenol to produce 4-(cyclopent-2-enyl)phenol which is then converted to 4-cyclopentenylphenol (translocation of the double bond).  The cyclopentenylphenol is then reacted with phenol followed by reaction with ethylene carbonate to produce the chain extender. In an example the chain extender is reacted with a 4,4′-MDI prepolymer in solvent.
Clever chemistry and an interesting compound, but its usefulness remains to be shown.

extender

Chain extender according to the invention

Single Pot NOPs

Patent Title: METHOD OF MAKING POLYOL COMPOSITIONS

Number/Link:  WO2019/028433

Applicant/Assignee: Univ. of California

Publication Date: 7 February 2019

“Gist”: Single-pot synthesis of natural-oil polyols by Prilezhaev oxidation and subsequent ring-opening of unsaturated triglycerids.

Why it is interesting: According to this invention NOPs can be prepared by reacting unsaturated natural oils with a peroxy acid. The epoxidation followed by ring opening occurs in a single reaction sequence.  The peroxy acid is first prepared by reacting a small organic acid with hydrogen peroxide. In the examples high oleic algae oils are used together with e.g. oxidized lactic acid.  The reaction has the advantage of being more rapid and using less toxic ingredients than current systems to prepare NOPs.

Prilezhaev

Prilezhaev reaction followed by ring-opening

Omniphobic Polyurea

Patent Title: MOISTURE-CURABLE OMNIPHOBIC COATINGS

Number/Link: US2019/0031909

Applicant/Assignee: US Navy

Publication Date: 31 January 2019

“Gist”: Polyurea topcoat containing both silane and perfluoro groups

Why it is interesting: According to this invention, a coating having both hydrophobic and oleophobic properties can be prepared by reacting an alkoxysilane-terminated polyurea with a perfluoromaterial having at least one alkoxy- or hydroxyl group. In an example a coating is prepared by reacting a polyurea based on HDI trimer and N-butyl-3-aminoppropyltrimethoxysilane with triethoxy(perfluoro-octyl)silane. The coating showed contact angles of more than 140 degrees vs water and more than 90 degrees vs hexadecane.

omniphobicpolyurea

Reaction system according to the invention