TPU from Oleic Acid

Title: RENEWABLY DERIVED THERMOPLASTIC POLYESTER-BASED URETHANES AND METHODS OF MAKING AND USING THE SAME

Number/Link: US2017/0145145

Applicant/Assignee: Trent University

Publication Date: 25-may-2017

“Gist”: Thermoplastic polyurethane made entirely from C9 monomers derived from oleic acid.

Why it is interesting: Azaleic acid can be prepared by oxidative cleavage of the oleic acid double bond.  Azaleic acid in turn can be converted to 1,9-nonanediol and to 1,7-heptamethyldiisocyanate via azides and Curtius rearrangment (see previous blog post). In this invention a polyester diol is prepared from azaleic acid and nonanediol and is then reacted with 1,7-heptamethylenediisocyanate together with nonanediol as chain extender, resulting in a phase-separated TPU. Best properties are obtained when the nonanediol is first prepolymerized with the diisocyanate. The TPU is said to degrade without cytotoxic degradation products, and is therefore useful for medical applications such as resorbable implants and scaffolds.
Related case: US2017/0145146.

Oleic Acid

 

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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

Self-Healing Polyurethane Elastomers

Patent Title: POLYURETHANE

 Number/Link: W02016185172

Applicant/Assignee: Croda

Publication date: 24-11-2016

Gist”: PU from polyols which contain both a fatty dimer residue and an H-bonding group, show self-healing properties

Why it is interesting: Polyurethane elastomers with ‘intrinsic’ self-healing properties (i.e. without the need for external chemicals like encapsulated monomers) can be prepared by reacting isocyanates with polyols that have at least one urethane, amide or carbonate group and at least one fatty dimer residue. It is theorized that the fatty dimer allows the soft-phase of the polymer to flow and H-bonds to form, thus restoring most of the properties after damage.  In the examples polyols with internal urethane groups were prepared by reacting C36 dimer diol with HDI, which were then reacted with MDI and BDO. Samples of the resulting elastomers were cut in half, and manually stuck together again under mild heating (60°C), thus recovering most of their tensile and elongation properties.

A dimer diol

A dimer diol

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