Isocyanate-Free Polyaminal-Polyurethane Foams

Patent Title: SYSTEM FOR DIMENSIONALLY STABLE ISOCYANATE-FREE POLYURETHANE FOAM

 Number/Link: WO2018/005142

Applicant/Assignee:  Dow

Publication date: 4 January 2018

Gist”: Polyaldehydes are reacted with polycarbamates in the presence of an acid catalyst, a metal oxide powder and a blowing agent.

Why it is interesting: According to this invention hydrolytically-stable foams can be prepared from a low molecular weight difunctional aldehyde and a polycarbamate with a functionality of about 3.5 to 4 and an equivalent weight of about 200 to 300, in the presence of a blowing agent and a protic acid as catalyst. Surprisingly the foams are rendered hydrolytically stable by the incorporation of a metal oxide powder with a specific particle size. In the examples polycarbamates are prepared by capping high functionality polyols with methylcarbamate and are then reacted with 1,4-cyclohexanedicarboxaldehyde together with p-toluensulfonic acid as catalyst, HFC245fa as blowing agent and MgO powder. The foams show densities of 130-170 kg/m³ and are said to be useful as sealants.

CHDA

Cyclohexanedicarbaldehyde

Coated Fracking Proppants

Patent Title: AMIDE BASED COATING

 Number/Link: WO2017/213855

Applicant/Assignee:  Dow

Publication date: 14 December 2017

Gist”: Proppant particles are coated with polyamide based on isocyanate and carboxylic acids

Why it is interesting: Proppant particles are used in the hydraulic fracturing process to force open rock fissures to extract gas and oil – as discussed before in this blog. According to this invention the proppant particles are coated with a reacting mixture of a polyisocyanate (e.g. polymeric MDI) and polycarboxilic acids (e.g. a blend of citric acid and an acid-terminated polyether triol). Under the high pressure and temperature of the fracture, the coating will bond the proppant particles together, thus preventing flow-back of the proppant and the blocking of the well. The coating can contain additives to capture heavy metals like radium and sulfides like hydrogensulfide to reduce contamination of the fracture fluid.

citricacid

Citric acid

Natural Oil Polyols using Self-Metathesis

Patent Title: POLYOLS FORMED FROM SELF-METATHESIZED NATURAL OILS AND THEIR USE IN MAKING POLYURETHANE FOAMS

 Number/Link: US2017/0291983

Applicant/Assignee:  Trent Univ.

Publication date: 12 october 2017

Gist”: NOPs from self-metathesized soy oils

Why it is interesting: The use of metathesis chemistry to modify natural oils before converting them to polyols has been discussed before in this blog:  see e.g. US2015/0337073, to the same applicant, which relates to cross-metathesis of natural oils using (e.g.) 1-butene. The current case is about self-metathesis of unsaturated natural oils, resulting in ‘metathesis oligomers’ which are then (partially) epoxidated and hydroxylated to prepare the polyols. In the examples soybean oil is turned into polyols with OH values between about 100 and 250, which are used to make flexible foams with densities of more than 150 kg/m³.

Oligomer from self-metathesis of unsaturated triglycerid


Hydrolysable Ureas

Patent Title: DYNAMIC UREA BONDS WITH FAST HYDROLYTIC KINETICS FOR POLYMERS

Number/Link: WO2017/155958

Applicant/Assignee: Univ. Illinois

Publication Date: 14 September 2017

“Gist”: Hindered urea bonds with fast hydrolysis kinetics are prepared from aromatic-sbstituted diamines and diisocyanates

Why it is interesting: Polyurethanes containing thermally reversible hindered urea bonds (HUBs) have been discussed before in this blog. In the current case the HUBs are prepared from aromatic (e.g aryl-) substituted amines and are said to show fast, pH-independent, hydrolysis kinetics. The HUBs can be built into linear or crosslinked polyurethanes or other polymers like polyamides, polycarbonates etc.  The resulting materials are useful for medical applications like drug delivery, water-degradable packaging, self-healing materials and the like.

HUB hysdrolysis

Hydrolysis reaction of phenyl-N-tetrabutyl-N-ethyl urea

 

PU Flexible Foams with Reduced Acetaldehyde Emissions

Title: METHOD FOR THE REDUCTION OF ALDEHYDE EMISSION IN POLYURETHANE FOAM

Number/Link: WO2017/134296

Applicant/Assignee: Huntsman

Publication Date: 10 August 2017

“Gist”: Cyanoacetamide is used as aldehyde scavenger

Why it is interesting: Reduction of aldehyde emissions from (especially flexible) polyurethane foams remains an important issue and has already been discussed a number of times on this blog. According to this case the use of (pref) 0.05 to 0.5 pbw of cyanoacetamide in a flexible foam formulation will reduce the emission of formaldehyde, acetaldehyde, propionaldehyde, and possibly of higher aldehydes as well.
While an interesting compound, the use of cyanoacetamide in polyurethanes is not new and the effect is hardly surprising.

Cyanoacetamide