Novel Aliphatic Polyester Polyols for TPU

Patent Title: POLYESTER POLYOLS AND POLYURETHANES

 Number/Link: WO2015/185744

Applicant/Assignee: DSM

Publication date: 10-12-2015

Gist”: Polyester polyols from succinic- and sebacic acid mixtures

Why it is interesting: Aliphatic polyester polyols used in polyurethane elastomers, are usually based on adipic acid and diols like MEG, DEG, butanediol or mixtures of these. Since recently, succinic acid has become a commercially avaible renewable compound and it makes sense to use it in polyester polyol production. Replacing adipic acid by succinic acid however, results in polyesters with a reduced hydrolysis resistance (at the same polyol molecular weight).  According to this invention this can be solved by using blends of succinic acid with C8 to C36  diacids, most preferably with sebacic (C10) acid.
Not a spectacular innovation and probably not as such patentable but a solid, useful idea.

Sebacic acid

Sebacic acid

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

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

Preparation of polyhydroxyurethanes according to the invention

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