Modified Polyisocyanurates

Patent Title: MODIFIED POLYISOCYANURA TE PLASTIC AND METHOD FOR PRODUCTION THEREOF

 Number/Link: WO2017/182108 WO2017/182109  WO2017/182110  (German)  

Applicant/Assignee:  Covestro

Publication date: 26-october-2017

Gist”: Partially trimerized diisocyanates are modified with monofunctional isocyanate-reactive compounds before complete trimerization

Why it is interesting: This series of applications relates to transparent polyisocyanurate coatings with controlled hydrophilicty, hydrophobicity, high scratch resitance etc. According to the invention trimers of diisocanates are reacted with a sub-stoichiometric amount of monofunctional hydrophobic, hydrophilic or siloxane-containing compounds, and then completely trimerized. In the examples HDI-trimer (prepared by partially trimerzing HDI and removing the rest of the monomer by thin film distillation) is reacted with e.g. methoxyPEG 500, dodecanol, perfluoroheptanol and N-(3-trimethoxyxilylpropyl)foramide and then trimerized using potassium acetate as catalyst.  The materials can e.g. be used as anti-fog coatings on optical lenses or anti-fingerprint coatings on cell phones.

HDI-isocyanurate

Thiol-Crosslinked Poly(hydroxyurethanes)

Title: METHOD FOR PRODUCING OR CURING POLYMERS USING THIOL-ENE POLYADDITION REACTIONS

Number/Link: W2017/081120

Applicant/Assignee:  Henkel

Publication Date: 18-05-2017

“Gist”: Unsaturated PHU are crosslinked using polythiols

Why it is interesting: The invention is about poly(hydroxyurethanes) (PHU) containing alkylene groups that are crosslinked using thiol-ene ‘click’ polyaddition reactions. The unsaturated PHU are first prepared by aminolysis of cyclocarbonates using unsaturated amines. In an example di-trimethylolpropane is converted to di-trimethylolpropanedicarbonate using ethylchloroformiate.  The di-TMPDC is then reacted with 3-aminopropylvinylether to prepare the PHU, which is then crosslinked using pentaerithritol-tetra(3-mecaptopropionate) in the presence of a photoinitiator and UV light.  The invention is said to be useful for isocyanate-free adhesive- and coating systems.

Di-trimethylolpropanedicarbonate

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

SiC-PU Nanocomposites

Patent Title: POLYURETHANE/UREA SILICON CARBIDE NANOCOMPOSITE

 Number/Link: WO2017/027231

Applicant/Assignee: 3M

Publication date: 16-feb-2017

Gist”: Surface modified SiC particles are dispersed in and covalently bound to a polyurethane matrix

Why it is interesting: Silicon carbide (carborundum) particles with an average particle size of about 500 nm are NCO-functionalized by reacting with a surface modfifying agent, e.g 2-triethoxysilylpropylisocyanate. The modified particles are then dispersed and covalently reacted into a polyurethane/polyurea matrix in an amount of 50-55% (w/w) on the composition. The composites can be made into highly erosion resistant films, for use on the outer surface of aircraft.

3-triethoxysilylpropylisocyanate

3-triethoxysilylpropylisocyanate

Aerogels from Isocyanates and Epoxies

Patent Title: ORGANIC AEROGELS BASED ON ISOCYANATE AND CYCLIC ETHER POLYMER NETWORKS

 Number/Link: WO2017016755

Applicant/Assignee: Henkel

Publication date: 2-feb-2017

Gist”: Isocyanate and epoxy are reacted in solvent and supercritically dried

Why it is interesting: While most ‘conventional’ aerogels are based on silica, organic aerogels, especially isocyanate-based aerogels, are also well known: polyurethane-, polyurea-, polyamide-, polyimide-, polycarbodiimide- and polyisocyanurate aerogels have all been reported. This invention adds another type of aerogel based on the reaction of isocyanates and cyclic ethers, esp. oxetanes and oxiranes. The isocyanate with a functionality of (pref.) 2 to 3, (e.g. 4,4′-MDI or methylidynetri-p-phenyletriisocyanate) is reacted with a cyclic ether  of (pref.) functionality of 2 to 3, (e.g. N,N-diglycidyl-4-glycidyloxianiline) in a suitable solvent (e.g. DMAc). After washing, the gel is dried with supercritical carbon dioxide. The materials are useful for thermal insulation and are said to have better mechanical properties compared to other organic aerogels.

N,N-Diglycidyl-4-glycidyloxyaniline

N,N-Diglycidyl-4-glycidyloxyaniline