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

1 Comment

by Gerhard Bleys on November 27, 2015 • Permalink

Posted in Polyols

Tagged bio-based materials, Environment, flexible foam, metathesis, NOP polyols, polyester polyol, renewable materials, rigid foam

Posted by Gerhard Bleys on November 27, 2015

https://purpatents.com/2015/11/27/natural-oil-polyols-using-metathesis-chemistry/

TPU from Asymmetric Chain Extenders

Patent Title: THERMOPLASTIC POLYURETHANE

Number/Link: WO2015/173337

Applicant/Assignee: Henkel

Publication date: 19-11-2015

“Gist”: TPU is made using diols with 1 prim- and one sec-OH group

Why it is interesting: Thermoplastic polyurethanes (TPU) have many desirable properties but are notoriously difficult to process: they need a high processing temperature (>160°C ) and have a high melt viscosity requiring high shear processing equipment. According to the current invention the melt viscosity can be greatly reduced by using an asymmetric diol as chain extender (i.e. with one pimary and one secondary hydroxyl group) instead of a conventional symmetric diol. In the examples polyester-MDI TPUs extended with asymmetric diols (e.g. 1,3-butanediol or 2,2,4-trimethyl-1,3-pentanediol) are shown to have a much lower melt viscosity compared to TPU extended with 1,4-butanediol. These TPUs are especially useful as hotmelt adhesives.

2,2,4,-trimethyl-1,3-pentanediol

Classic PU Patent of the Month: Non-Isocyanate Polyhydroxyurethanes by Dow (1957)

Title: Polyhydroxyurethanes

Number/Link: US3084140

Applicant/Assignee: Dow

Publication date: 2-04-1963

“Gist”: bis-cyclocarbonates are reacted with aliphatic polyamines

Why it is interesting: Non-isocyanate polyurethanes (NIPU) are still gaining in popularity – at least in the patent and science literature. The chemistries to make NIPU are far from new as discussed in a previous ‘classic patent of the month’ on this blog. The most common route to NIPU is by reacting cyclocarbonates with amines resulting in hydroxyurethanes, as was first dicussed in this patent. The intent of the invention was, actually, not to avoid the use of isocyanates but to make hydroxy-group containing polyurethanes which were said to be ‘highly desirable’: the OH groups can act as points for crosslinking, make the resin more hydrophilic and compatible with certain materials etc.

Preparation of polyhydroxyurethanes according to the invention

Innovation in Polyurethanes

Natural Oil Polyols Using Metathesis Chemistry

TPU from Asymmetric Chain Extenders

Classic PU Patent of the Month: Non-Isocyanate Polyhydroxyurethanes by Dow (1957)

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