Hybrid Polyisocyanurates for Composites and Coatings

Patent Title: DUAL-CURING ISOCYANURATE POLYMERS

 Number/Link:WO2018/087395 WO2018/087396  WO2018/087399 (German)

Applicant/Assignee:  Covestro

Publication date: 17 May 2018

Gist”:  Di-isocyanate trimer is reacted with hydroxymethacrylates and polyacrylates in the presence of a trimerization catalyst. 

Why it is interesting: According to these inventions a reaction system with two curing modes can be prepared by mixing high functionality oligomeric isocyanate, ethylenically unsaturated compounds, unsaturated compounds containing isocyanate-reactive groups, timerization catalyst and a free-radical initiator at an NCO index of 100 to 200. The system shows a relatively low viscosity and can e.g. be used in fiber-reinforced composites and in coatings. In the examples HDI trimer is reacted with hexanedioldimethacrylate and hydroxypropylmethacrylate in the presence of potassium acetate and a peroxybenzoic acid.

HDI isocyanurate

HDI-trimer


Hybrid Polyurethane Elastomer

Patent Title:  PROCESS FOR PRODUCING ELASTOMERS

 Number/Link: WO2018069348 (German)

Applicant/Assignee:  Covestro

Publication date: 19 April 2018

Gist”: Unsaturated polycarbonate polyols are reacted with isocyanates together with a peroxide

Why it is interesting: Unsaturated polyethercarbonate polyols are prepared by reacting alkyleneoxides (e.g. PO) together with carbondioxide and an unsaturated monomer like a glycidylether or -ester or cyclooctadienemonoepoxide. These polyols can then be reacted with isocyanates in the presence of  a free-radical initiator like an peroxide. The resulting material can then be crosslinked in a separate step. The hybrid elastomers are said to have improved tensile properties at same or similar hardness.
A related application is WO2018/069350.

glycidylmethacrylate

Glycidylmethacrylate

PIR-Oxazolidone Foams from Natural Oils

Patent Title: METHOD FOR MANUFACTURING A POLYURETHANE-MODIFIED FOAM, FOAM OBTAINED, AND USES

Number/Link: US2018/0030196

Applicant/Assignee:  Soprema et al.

Publication date: 1 February 2018

Gist”: Unsaturated natural oils are epoxidized and reacted with an excess of isocyanate in the presence of a blowing agent.

Why it is interesting: Conventionally natural oils are incorporated into polyurethanes by first converting them to polyols (“NOPs”) by hydroformylation or epoxidation and ring opening and then reacting the NOPs with isocyanates. According to this invention the natural oils (preferably extracted from microalgae) are epoxidized and then mixed and heated with a (e.g. 3:1) excess of isocyanate (e.g. polymeric MDI) in the presence of a blowing agent (e.g. isopentane). It is said that oxazolidone rings from the isocyanate-epoxy reaction will form at the same time as isocyanurate rings and homopolymerized epoxides. The foams are said to be useful for thermal insulation applications.

oxazolidone

Formation of oxazolidone rings according to the invention

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