US20210363452A1 Coating agents and coated articles
US20210363452A1
Coating agents and coated articles
InventorJie WenKristin TatonLaurie LawinWilliam KnopkeEric GuirePatrick GuireCurrent
Assignee Innovative Surface Technologies LLC
High-Performance Medical Coatings – Home (harlandmedical.com)
The invention describes novel coating agents that include a polymer, one or more latent reactive groups and one or more noncovalent linking groups, the noncovalent linking groups selected to interact with a substrate to which the coating agent is applied.
＜Ex1. Synthesis of Photo-Poly(octadecene-alt-maleic anhydride)silane—(Photo-POMAS)＞
↓5g poly(octadecene-alt-maleic anhydride), (MW 30,000-50,000, Aldrich, Milwaukee, Wis.),
↓0.5g 4-aminobenzophenone (Aldrich)
↓0.08g 4-dimethylaminopyridine (Aldrich)
↓100 mL chloroform
↓refluxed under argon for 2 hours.
↓5ml aminopropyl methylbis(trimethylsiloxy)silane portion
↓refluxed for another 2 hours.
↓washed three times with 2N HCl,
↓three washes with deionized water.
↓dried over anhydrous Na2SO4.
↓vacuum filtration,
↓The filtrate was concentrated to dryness on a rotavap to yield 7.5 g of solid material.
The polymer product was characterized
1H NMR (δ0.0ppm, CH 3—Si;δ0.8-1.5 ppm, alkyl protons;δ2.5-3.5 ppm, CH—C═O;δ7.4-7.6 ppm, aromatic protons)
FT-IR (C═O:1710 cm−1; benzophenone:1593 cm−1; Si—CH3:1258cm−1, 843cm−1,755cm−1;Si—O—Si:1052 cm−1).
The polymer product was soluble in
isopropanol (IPA), acetone, hexane, chloroform, tetrahydrofuran (THF), and ethyl acetate, but insoluble in water.
“noncovalent linking group” is siloxane.
※Non-covalent bonds include Van der Waals forces, hydrogen bonds, electrostatic interactions, and hydrophobic interactions. Compared to covalent bonds, they are weaker by one to three orders of magnitude. Therefore, they can be easily broken by increasing the temperature or by performing various chemical treatments with certain chemical reagents.
＜Ex 2. Coating of Silicone Tubing with Photo-POMAS＞
↓7.5 g Photo-POMAS polymer / 100 ml of IPA
↓10 cm silicone tubing (DOVER™ silicone catheter, Covidien) / cleaning isopropanol.
↓The silicone tubing pieces were coated with the Photo-POMAS/IPA 30 seconds
↓0.5 cm/sec UP
↓room temperature for 3 minutes
↓irradiated with uv light (Harland Medical UVM400, Eden Prairie, Minn.) (300 to 400 nm) for 1 minute at a distance of 15 cm from the light source.
＜Ex 3. Lubricious Coating＞
↓Lubricent™ 460 ―30 seconds
↓0.5 cm/sec
↓room temperature for 3 minutes
irradiated with uv light (300 to 400 nm) at 15 cm for 3 minutes
Silicone tubing coated with Lubricent™ : control.
＜Ex 4. Congo Red Staining＞
50 mg/ml Congo red solution (Aldrich Chemicals, Milwaukee, Wis.)/water
1 minute of soaking in the Congo red solution,
deionized water 3 times.
＜Ex 5. Friction Test＞
commercial friction tester (Harland Medical, FTS 5000, Eden Prairie, Minn.) for lubricity. I
＜Ex6. Superhydrophobic Coating＞
↓Photo-POMAS coated
↓16 mg/ml fumed silica particles (commercially available under the product name CAB-O-SIL TS720, Cabot Corporation, Boston Mass.)
13.3 mg/ml polyisobutylene (PIB) (BASF, Florham Park, N.J., MW 2000K) in hexane
＜ Ex7. Cytotoxicity＞
＜Ex8. Photopatterning＞
the silicone discs were cleaned by immersion in isopropyl alcohol (IPA), followed by sonication for 15 minutes.
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