Natural Oil Polyols using Self-Metathesis

Patent Title: POLYOLS FORMED FROM SELF-METATHESIZED NATURAL OILS AND THEIR USE IN MAKING POLYURETHANE FOAMS

 Number/Link: US2017/0291983

Applicant/Assignee:  Trent Univ.

Publication date: 12 october 2017

Gist”: NOPs from self-metathesized soy oils

Why it is interesting: The use of metathesis chemistry to modify natural oils before converting them to polyols has been discussed before in this blog:  see e.g. US2015/0337073, to the same applicant, which relates to cross-metathesis of natural oils using (e.g.) 1-butene. The current case is about self-metathesis of unsaturated natural oils, resulting in ‘metathesis oligomers’ which are then (partially) epoxidated and hydroxylated to prepare the polyols. In the examples soybean oil is turned into polyols with OH values between about 100 and 250, which are used to make flexible foams with densities of more than 150 kg/m³.

Oligomer from self-metathesis of unsaturated triglycerid


Non-Isocyanate Poly(Amide-Hydroxyurethanes)

Patent Title: NON-ISOCYANATE POLYURETHANES AND METHODS OF MAKING AND USING THE SAME

 Number/Link: WO 2017/ 030880

Applicant/Assignee: ELEVANCE RENEWABLE SCIENCES

Publication date: 23-feb-2017

Gist”: Telechelic cyclocarbonate-alkylesters are reacted with diamines in the melt

Why it is interesting: According to this invention (ω-) unsaturated alkylesters can be converted to mono-cyclocarbonate alkylesters and then reacted with diamines to prepare thermoplastic poly(amide-hydroxyurethanes) (PAHU). For example methyl-9-decenoate was first epoxidized and then reacted with CO2 to produce 9,10-cyclic carbonate-methyl decanoate. After separation and washing the cyclocarbonate was reacted – in the melt- with a mixture of dodecane diamine and a PTMO diamine (Jeffamine THF-100). It is said that the unsaturated alkylesters can be prepared from natural oils using (cross- or self-) metathesis followed (or preceded) by transesterifaction with alkanols.

PAHU preparation scheme

PAHU preparation scheme

TPU from Gem-Dialkyl Cyclooctene

Patent Title: TELECHELIC PREPOLYMERS AND REACTION PRODUCTS THEREOF

 Number/Link: WO 2017/023506

Applicant/Assignee: University of Minnesota

Publication date: 9-feb-2017

Gist”:  Diols are made by ROM polymerization of gem-dialkyl cyclooctene together with a symmetrical diol as chain transfer agent

Why it is interesting: According to this application, thermoplastic polyurethanes containing geminal dialkyl groups have far superior thermal stability, oxidative-, hydrolytic- and barrier properties as compared to TPUs containing conventional soft segments. Diols containing gem-dialkyl groups are prepared by ring-opening metathesis polymerization (ROMP) of a gem-dialkyl cyclooctene with a suitable catalyst and in the presence of a symmetrical aliphatic olefin chain transfer agent having functional end groups. Examples are 5,5-dimethylcyclooct-1-ene and 1,8-oct-4-ene diol as the chain transfer agent.  The resulting diol is then reacted with (e.g.) 4.4′-MDI to prepare the TPU.

5,5-dimethylcyclooct-1-ene

5,5-dimethylcyclooct-1-ene

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