PIR-Oxazolidone Foams from Natural Oils

Patent Title: METHOD FOR MANUFACTURING A POLYURETHANE-MODIFIED FOAM, FOAM OBTAINED, AND USES

Number/Link: US2018/0030196

Applicant/Assignee:  Soprema et al.

Publication date: 1 February 2018

Gist”: Unsaturated natural oils are epoxidized and reacted with an excess of isocyanate in the presence of a blowing agent.

Why it is interesting: Conventionally natural oils are incorporated into polyurethanes by first converting them to polyols (“NOPs”) by hydroformylation or epoxidation and ring opening and then reacting the NOPs with isocyanates. According to this invention the natural oils (preferably extracted from microalgae) are epoxidized and then mixed and heated with a (e.g. 3:1) excess of isocyanate (e.g. polymeric MDI) in the presence of a blowing agent (e.g. isopentane). It is said that oxazolidone rings from the isocyanate-epoxy reaction will form at the same time as isocyanurate rings and homopolymerized epoxides. The foams are said to be useful for thermal insulation applications.

oxazolidone

Formation of oxazolidone rings according to the invention

Polyols from Proteins

Patent Title: POLYOLS FROM PROTEIN BIOMASS

 Number/Link: WO2016/094859

Applicant/Assignee: Inventors

Publication date: 16-06-2016

Gist”: Transamidation of protein with diamines followed by carbonation

Why it is interesting: Currently most renewable polyols are based on natural oils (NOPs) like soy-oil, but it is also possible to make polyols from proteins. According to this invention this can be accomplished by first cleaving the protein amide bonds by transamidation with an excess of low molecular weight polyamines using a boric acid derivative as catalyst. Then stripping the excess amines and reacting with cyclocarbonates. In an example soy-meal is reacted with ethylenediamine and then with ethylene carbonate resulting in a urethane polyol. The polyols have a high primary OH content, are auto-catalytic and are said to be useful for the production of PU resins and rigid foams.

Diol acoording to the invention. R is an amino acid residue.

Polyol according to the invention. R is an amino acid residue.

 

Natural Oil Polyols Using Metathesis Chemistry

Patent Title: METATHESIZED TRIACYLGLYCEROL POLYOLS FOR USE IN POLYURETHANE APPLICATIONS AND THEIR RELATED PROPERTIES

 Number/Link: US2015/0337073

Applicant/Assignee: Trent University

Publication date: 26-11-2015

Gist”: Palm oil is metathesized before hydroxylation.

Why it is interesting: Natural-oil based polyols (NOPs) prepared from unsaturated plant oils are well known in the PU industry. In this case however, the oil is first modified into a ‘metathesized triacylglycerol’ by cross-metathesis using (e.g.) 1,2-butene and an appropriate catalyst. The result is a complex mixture of triglycerids, the unsaturations of which are then epoxidized and hydrolyzed into the final polyol.  In the examples palm-oil metathezised triacylglycerol (PMTAG) is compared to a commercially available soy-oil polyol when used to perpare both flexible and rigid foams. While the chemistry is interesting there does not appear to be much advantage to this type of NOP.

Metathesis reaction of triolein with butene

Metathesis reaction of triolein with butene