Aliphatic Polyisocyanurate Composites

Patent Title: METHOD FOR PRODUCING A POLYISOCYANURATE COMPOSITE MATERIAL

 Number/Link: WO 2017/191216  (German)

Applicant/Assignee:  Covestro

Publication date: 9 November 2017

Gist”: Partially trimerized aliphatic diisocyanates are mixed with glass fiber and reacted using a trimerization catalyst

Why it is interesting: Conventional fiber-reinforced composites based on unsaturated polyesters, epoxies, polyurethane and the like are not weather-stable and need to be coated for outdoor use. Weather stable polyisocyanurate composites are known (WO2007/096216 – Huntsman) but are based on aromatic diisocyanates and show high reactivity and short ‘pot life’. According to this invention, PIR composites with improved reaction profile and weatherability can be prepared from partially trimerized aliphatic diisocyanates with a diisocyanate monomer content of less than 20% (w/w). In the examples commercially available HDI and IPDI trimer is used together with short glass fiber and a potassium acetate/PEG 400 blend as catalyst cured at a temperature of 160 to 180°C.

Isophorone diisocyanate (IPDI)

 

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

TPU Aerosol

Title: POLYURETHANE AEROSOL COMPOSITIONS, ARTICLES, AND RELATED METHODS

Number/Link: US20170198150

Applicant/Assignee: 3M

Publication Date: 13-july-2017  (priority PCT)

“Gist”: Aqueous dispersion of a hydrazide-extended  TPU can be sprayed as aerosol to make protective films

Why it is interesting: An aqueous thermoplastic polyurethane dispersion is prepared from a non-yellowing diisocyanate, e.g. bis(4-isocyanatocyclohexyl), a diol (e.g. PPG2000), a difunctional hydrazine or hydrazide chain extender (e.g. 1,3-diaminourea) and a water solubilizing compound (e.g. dimethylolpropionic acid).  Together with a propellant the, composition is shelf-stable and can be aerosol-sprayed to form clear, non-yellowing protective films.

3M’s aerosol-sprayed protective film.

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

Self-Healing Polyurethane Coatings

Patent Title: Self-Repairing Polyurethane Networks

 Number/Link: US20160289495

Applicant/Assignee: Clemson University

Publication date: 6-10-2016

Gist”: Polyurethane networks with alkylated polysaccharide moiety show self-healing properties

Why it is interesting: Chitosan (pref.) is alkylated by reacting with dodecylaldehyde (in solvent) and reducing the resulting imine with sodium cyanoborohydride. The alkylated chitosan is then reacted with isocyanate and polyol.  When used as coating, the material is claimed to show self-healing properties when irradiated with UV light. Modifying the composition by incorporation of catechol, or by changing the saccharide allows for materials which ‘heal’ when exposed to ferric ions or carbon dioxide. No explanation for this behaviour is given and it is not immediately clear to me why this should work.

Self-healing network according to the invention. The isocyanate used was (E)-3,5-bis(6-isocyanatohexyl)- 6-( ( 6-isocyanatohexyl)imino )-1,3,5-oxadiazinane-2, 4-dione.

Self-healing network according to the invention. The isocyanate used was (E)-3,5-bis(6-isocyanatohexyl)-6-( ( 6-isocyanatohexyl)imino )-1,3,5-oxadiazinane-2,4-dione. ALK= alkyl, POL=polyol.