Synthesis and characterization of UV-curable castor oil-based polyfunctional polyurethane acrylate via photo-click chemistry and isocyanate polyurethane reaction

Guangxue Chen, Xiaoyuan Guan, Ruixin Xu, Junfei Tian, Minghui He, Wei Shen, Jianwen Yang

Research output: Contribution to journalArticleResearchpeer-review

31 Citations (Scopus)

Abstract

In this paper, UV-curable castor oil-based polyfunctional polyurethane acrylate (COME-PUA) was synthesized via photo-click chemistry and isocyanate polyurethane reaction. Facile and highly efficient side-chain functionalization of castor oil (CO) was first achieved via thiol-ene photo-click chemistry with β-mercaptoethanol (ME). 1H NMR result indicated that almost 100% conversion of double-bond in CO was observed within 10 min, and the average hydroxyl functionality of the obtained polyol COME was about 6. Next, COME was modified by isocyanate polyurethane reaction with hydroxypropyl acrylate (HPA), isophorone diisocyanate (IPDI) and PEG-200 as the chain extender in order to prepare the resin COME-PUA. Results of both 1H NMR and FTIR revealed that the targeted COME and COME-PUA were successfully synthesized. Furthermore, UV-curing kinetic of COME-PUA was revealed by real-time FTIR, showing a higher UV-curing rate than the common CO-PUA. Finally, some physical properties of curing films were studied.

Original languageEnglish
Pages (from-to)11-16
Number of pages6
JournalProgress in Organic Coatings
Volume93
DOIs
Publication statusPublished - 1 Apr 2016

Keywords

  • Castor oil
  • Polyurethane acrylate
  • Thiol-ene click reaction
  • UV-curable

Cite this

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title = "Synthesis and characterization of UV-curable castor oil-based polyfunctional polyurethane acrylate via photo-click chemistry and isocyanate polyurethane reaction",
abstract = "In this paper, UV-curable castor oil-based polyfunctional polyurethane acrylate (COME-PUA) was synthesized via photo-click chemistry and isocyanate polyurethane reaction. Facile and highly efficient side-chain functionalization of castor oil (CO) was first achieved via thiol-ene photo-click chemistry with β-mercaptoethanol (ME). 1H NMR result indicated that almost 100{\%} conversion of double-bond in CO was observed within 10 min, and the average hydroxyl functionality of the obtained polyol COME was about 6. Next, COME was modified by isocyanate polyurethane reaction with hydroxypropyl acrylate (HPA), isophorone diisocyanate (IPDI) and PEG-200 as the chain extender in order to prepare the resin COME-PUA. Results of both 1H NMR and FTIR revealed that the targeted COME and COME-PUA were successfully synthesized. Furthermore, UV-curing kinetic of COME-PUA was revealed by real-time FTIR, showing a higher UV-curing rate than the common CO-PUA. Finally, some physical properties of curing films were studied.",
keywords = "Castor oil, Polyurethane acrylate, Thiol-ene click reaction, UV-curable",
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Synthesis and characterization of UV-curable castor oil-based polyfunctional polyurethane acrylate via photo-click chemistry and isocyanate polyurethane reaction. / Chen, Guangxue; Guan, Xiaoyuan; Xu, Ruixin; Tian, Junfei; He, Minghui; Shen, Wei; Yang, Jianwen.

In: Progress in Organic Coatings, Vol. 93, 01.04.2016, p. 11-16.

Research output: Contribution to journalArticleResearchpeer-review

TY - JOUR

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AU - Chen, Guangxue

AU - Guan, Xiaoyuan

AU - Xu, Ruixin

AU - Tian, Junfei

AU - He, Minghui

AU - Shen, Wei

AU - Yang, Jianwen

PY - 2016/4/1

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N2 - In this paper, UV-curable castor oil-based polyfunctional polyurethane acrylate (COME-PUA) was synthesized via photo-click chemistry and isocyanate polyurethane reaction. Facile and highly efficient side-chain functionalization of castor oil (CO) was first achieved via thiol-ene photo-click chemistry with β-mercaptoethanol (ME). 1H NMR result indicated that almost 100% conversion of double-bond in CO was observed within 10 min, and the average hydroxyl functionality of the obtained polyol COME was about 6. Next, COME was modified by isocyanate polyurethane reaction with hydroxypropyl acrylate (HPA), isophorone diisocyanate (IPDI) and PEG-200 as the chain extender in order to prepare the resin COME-PUA. Results of both 1H NMR and FTIR revealed that the targeted COME and COME-PUA were successfully synthesized. Furthermore, UV-curing kinetic of COME-PUA was revealed by real-time FTIR, showing a higher UV-curing rate than the common CO-PUA. Finally, some physical properties of curing films were studied.

AB - In this paper, UV-curable castor oil-based polyfunctional polyurethane acrylate (COME-PUA) was synthesized via photo-click chemistry and isocyanate polyurethane reaction. Facile and highly efficient side-chain functionalization of castor oil (CO) was first achieved via thiol-ene photo-click chemistry with β-mercaptoethanol (ME). 1H NMR result indicated that almost 100% conversion of double-bond in CO was observed within 10 min, and the average hydroxyl functionality of the obtained polyol COME was about 6. Next, COME was modified by isocyanate polyurethane reaction with hydroxypropyl acrylate (HPA), isophorone diisocyanate (IPDI) and PEG-200 as the chain extender in order to prepare the resin COME-PUA. Results of both 1H NMR and FTIR revealed that the targeted COME and COME-PUA were successfully synthesized. Furthermore, UV-curing kinetic of COME-PUA was revealed by real-time FTIR, showing a higher UV-curing rate than the common CO-PUA. Finally, some physical properties of curing films were studied.

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