Bio-Based Acoustic Polyurethane Foam

Patent Title: POLYURETHANE MATERIALS FORMED FROM EPOXIDIZED PLANT OILS

 Number/Link: US2017/0081460

Applicant/Assignee: IBM

Publication date: 23-mar-2017

Gist”: Natural oils are converted into isocyanate-functional polyols and then polymerized

Why it is interesting: Epoxidized vegetable oils are hydrolized and saponified using NaOH, resulting in a mixture of acid-ended polyols. The acid groups are then converted into azides using diphenylphosphoryl azide, which then rearrange into isocyanate groups (Curtius rearrangement).  The isocyanate-ended polyols can be polymerized and further crosslinked using di-isocyanates. The materials are said to be useful as components for acoustic foams, used e.g. in mainframe computers.
This is the second IBM PU patent discussed in this blog. However, I doubt if they have an actual chemistry lab since their examples are “prophetic” rather than real.

IBM

Reaction scheme according to the invbention

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Low Density Foamed TPU

Patent Title: FOAMED THERMOPLASTIC POLYURETHANE AND MICROWAVE MOLDED ARTICLE THEREOF

 Number/Link: US2017/0073490

Applicant/Assignee: Sunko Ink; Tayin R&D

Publication date: 16-mar-2017

Gist”: Blown TPU pellets are subjected to a second foaming process using microwaves

Why it is interesting: Thermoplastic polyurethane is extruded together with an excess of blowing agent using a single screw extruder and a pelletizer. The foamed pellets are then put in a mould together with water and subjected to microwave radiation which causes the pellets to expand and sinter into a moulded part. In the examples expandable microspheres are used as blowing agent in amounts of 5 to 25 php of TPU. The pellets are irradiated for 20 to 180 s at a power of up to 5000 W. Moulded densities as low as 170 kg/m³ are achieved.

SEM picture of moulded TPU according to the invention

 

TPU with Reduced Blooming

Patent Title: POLYOLS WITH REDUCED CYCLIC OLIGOMER CONTENT AND THERMOPLASTIC POLYURETHANE COMPOSITIONS THEREOF

 Number/Link: WO2017040505

Applicant/Assignee: Lubrizol

Publication date: 9-mar-2017

Gist”: Enzymes are used to remove cyclo-oligomers from polyster polyols

Why it is interesting: It is known that the “blooming” of polyester TPUs (i.e. the fomation of a white surface haze) is caused by the migration of cyclic polyester oligomers to the surface of the TPU. Conventionally these unreactive cyclo-oligomers are removed by e.g extraction, or their formation is prevented by careful choice of diol and diacid as mentioned before in this blog. According to this invention the cyclic polyesters can be removed by treating the polyol with an enzyme. Enzymes of the lipase or cutinase type are immobilized by attachement to an inert and insoluble material and then heated together with the polyol at 70 to 90ºC to ‘cut’ the polyester rings. After treatment of the polyol the immobilized enzyme can be filtrated.

A cyclic diester

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