Polyols from Natural Oils using the Alkyne Zipper Reaction

Title: POLYURETHANE MATERIALS FORMED FROM UNSATURATED PLANT OILS VIA AN ALKYNE ZIPPER REACTION

Number/Link: US2017/0166679 US2017/0166680

Applicant/Assignee: IBM

Publication Date: 15-june-2017

“Gist”: Oils are turned into alkyne alcohols, ‘zippered’ and oxidized to polyols

Why it is interesting: This is yet  another IBM patent application about interesting, albeit somewhat exotic, chemistry and featuring only “prophetic” examples. In this case unsaturated natural oils are first converted into unsaturated alcohols and then into alkynes by bromination and elimination.  The internal alkynes are then converted to terminal alkynes by an “alkyne zipper reaction” and then into hydroxyl groups by hydroboration and epoxidation/ring-opening. This series of reactions should result in polyols having two primary- and one or more secondary OH groups, useful, for example, for the preparation of sound absorbing foams.

Reaction sequence according to the invention

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Aerogels from Isocyanates and Epoxies

Patent Title: ORGANIC AEROGELS BASED ON ISOCYANATE AND CYCLIC ETHER POLYMER NETWORKS

 Number/Link: WO2017016755

Applicant/Assignee: Henkel

Publication date: 2-feb-2017

Gist”: Isocyanate and epoxy are reacted in solvent and supercritically dried

Why it is interesting: While most ‘conventional’ aerogels are based on silica, organic aerogels, especially isocyanate-based aerogels, are also well known: polyurethane-, polyurea-, polyamide-, polyimide-, polycarbodiimide- and polyisocyanurate aerogels have all been reported. This invention adds another type of aerogel based on the reaction of isocyanates and cyclic ethers, esp. oxetanes and oxiranes. The isocyanate with a functionality of (pref.) 2 to 3, (e.g. 4,4′-MDI or methylidynetri-p-phenyletriisocyanate) is reacted with a cyclic ether  of (pref.) functionality of 2 to 3, (e.g. N,N-diglycidyl-4-glycidyloxianiline) in a suitable solvent (e.g. DMAc). After washing, the gel is dried with supercritical carbon dioxide. The materials are useful for thermal insulation and are said to have better mechanical properties compared to other organic aerogels.

N,N-Diglycidyl-4-glycidyloxyaniline

N,N-Diglycidyl-4-glycidyloxyaniline

 

 

In Situ Reticulated Viscoelastic Foams

Patent Title: VISCOELASTIC AND RETICULATED POLYURETHANE FOAM AND THE PREPARATION THEREOF

 Number/Link: WO2016/198433

Applicant/Assignee: Covestro

Publication date: 15-dec-2016

Gist”: Composition of 3 semi-miscible polyols and a surfactant

Why it is interesting: This case claims a polyol composition for the preparation of a viscoelastic, reticulated foam without the need for a separate reticulation step. The composition consists of (at least) three polyols and a surfactant:  a low mole-weight all-PO ‘rigid’ triol, a conventional flexible polyol, a high- or all-EO polyol and some off-the-shelf silicone surfactant.  The composition is foamed with water and polymeric MDI or a polymeric MDI/TDI mixture. This is a well-known composition and it is hard to see why this should result in a reticulated foam – unless maybe in some fine-tuned cases.  Apart from the ball rebound being less than 15% the claims do not mention any parameters related to reticulated foam (such as airflow). It is doubtful (in my opinion) that this will get granted.

Cell structure of a reticulated foam

Cell structure of a reticulated foam