N-isopropyl acrylamide

1. Presented By
Sunidhi
Ph.D.(Pharmaceutics)
Presented To
Prof. Munish ahuja
N- isopropyl acrylamide
Department of Pharmaceutical Sciences
Guru Jambheswar University of Science and Technology
Hisar, Haryana

2. N- isopropyl acrylamide
 General Description:
 IUPAC Name :N-(propan-2-yl)prop-2-enamide
 Synonyms: NIPAM, Isopropyl acrylamide, N-(1-methylethyl)-
2-propenamide
 Molecular Formula: C6H11NO
 Molecular Weight: 113.16 g/mol
 Color/Form: Cream-Colored powder/Crystalline solid
 Melting Point: 64.0°C
 Solubility: Soluble in water

3. Chemical Structure of N- isopropyl acrylamide

4. N- isopropyl acrylamide is an acrylamide group
monomer used in the preparation of thermally
sensitive, water-swellable hydrogels.
N-Isopropylacrylamide is used to produce poly
(N-isopropylacrylamide) (pNIPA, pNIPAAm, pNIPAA
or pNIPAm) thermo sensitive polymer, water swellable
hydrogels and micelles.
Polymers that contain NIPAM shrink dramatically
above 33°C and may be useful for drug delivery.
Storage Conditions :Keep container tightly closed in a
dry and well-ventilated place.

5. Environmental Fate & Exposure:
□ N-Isopropylacrylamide's production and use as a binder in
textiles, paper adhesives, detergents, cosmetics, and chemical
intermediate in processes such as drug delivery systems and
nanotechnology may result in its release to the environment
through various waste streams.
□ Decomposition : When heated to decomposition it emits toxic
fumes of nitrogen oxides and Carbon oxides.
□ Occupational exposure to N-isopropylacrylamide may occur
through inhalation and dermal contact with this compound at
workplaces where N-isopropylacrylamide is produced or used
it can cause nerve damage.

6. □ Poly(N-isopropylacrylamide)
□ It can be synthesized from N-isopropylacrylamide . It is
synthesized via free-radical polymerization.
□ Homopolymerization
The process of free radical polymerization of a single type
of monomer, in this case, N-isopropylacrylamide, to form the
polymer is known as a homopolymerization. The radical
initiator azobisisobutyronitrile (AIBN) is commonly used in
radical polymerizations.

7.  Poly(N-isopropyl acrylamide) is a temperature sensitive
hydrogel.
 Poly(N-isopropyl acrylamide) has a lower critical solution
temperature (LCST) at 31–33°C in water. Below that
temperature, the hydrogel is swollen in water due to the hydrogen
bonding (hydrated state), and above that LCST, the hydrogel
collapsed (dehydrated) and becomes hydrophobic due to the
breakage of hydrogen bonding.
 Importantly, the LCST of p(NIPAM) hydrogels can be
controlled by incorporating more hydrophilic or hydrophobic
monomer into the hydrogel structure.

9. Application
□ The versatility of pNIPAM has led to finding uses in
macroscopic gels, microgels,membranes, sensors, biosensors,
thin films, tissue engineering, and drug delivery. (VPTT)
□ pNIPAM have also been used in pH-sensitive drug
delivery systems, antifouling coatings and “smart” optical
systems.
□ Some examples of these drug delivery systems may include the
intestinal delivery of human calcitonin, delivery of insulin and
the delivery of ibuprofen.

10. PNIPAM in Tissue Engineering (Tissue Regeneration)
https://www.researchgate.net/profile/Sajjad_Ashraf/
publication//-PNIPAM-scaffolds-and-growth-factors.png

12. http://www.pc.tu-clausthal.de/index

13. Uses of N-isopropyl acrylamide
□ Binders in textiles, paper adhesives, detergents, cosmetic
□ One of the water-soluble monomers used in the production of
polyacrylamides, poly(acrylic acid), and poly(methacrylic
acid)
□ Chemical intermediate in the development of photosensitized
drug delivery systems
□ Core/shell precursor in gold nanoparticle applications
□ In the synthesis of thermosensitive hydrogels which are
hydrophilic polymer networks that are able to swell and retain
large amounts of water and maintain three-dimension swollen
structures.

14. □ Bulk-polymerized: hard shatterproof, transparent or colored
material (glass substitute, decorative illuminated signs, contact
lenses, dentures, medical instruments, specimen preservation,
furniture components).
□ Solution polymers: coatings for paper, textiles, etc.
□ Suspension-polymerized: beads and molding powders
(headlight lenses, adsorbents in chromatography, ion-exchange
resins).
□ Aqueous emulsions: adhesives, laminated structures, fabric
coatings, nonwoven fabrics.

15. 1 Water-in-oil Pickering emulsion
polymerization of N-isopropyl acrylamide
using starch-based nanoparticles as emulsifier.
Zhai, Kankan, et al.
(2019)
2 pH-Thermosensitive hydrogel based on
polyvinyl alcohol/sodium alginate/N-isopropyl
acrylamide composite for treating re-infected
wounds
A.S. Montaser et al.(2019)
3 Poly(N-isopropylacrylamide) and
Copolymers:A Review on Recent Progresses
in Biomedical Applications
Lanzalaco et al.
(2017)
S. No. Article Reference

16. 4 Development of Novel
N-isopropylacrylamide(NIPAAm)
Based Hydrogels with Varying Content
of Chrysin Multiacrylate
Shuo Tang, et,al
(2017)
5 Potential application of poly(N-
isopropylacrylamide) gel containing
polymeric micelles to drug delivery
systems
Yan, H., & Tsujii,
K. (2005)
6 Synthesis of N-isopropylacrylamide
from acrylonitrile and
isopropyl alcohol over solid acids
Chen, X., H.
Matsuda, and T.
Okuhara. (2000)

17. S.No Article Reference
7 Modulating the phase transition
temperature and thermosensitivity in
N-isopropylacrylamide copolymer gel
Ryo Yoshidai et. al
(1994)
8 Volume Phase Transitions of Ionized N-
Isopropylacrylamide gels
Shunsuke Hirotsu,et
al.(1987)

18. Reference
□ PubChemURL: https://pubchem.ncbi.nlm.nih.gov.
□ https://toxnet.nlm.nih.gov.
□ Gao, Y., Zago, G. P., Jia, Z., & Serpe, M. J. (2013). Controlled and triggered
small molecule release from a confined polymer film. ACS Applied Materials
& Interfaces, 5(19), 9803-9808
□ Hendrickson, G. R., & Lyon, L. A. (2009). Bioresponsive hydrogels for
sensing applications. Soft Matter, 5(1), 29-35.
□ Islam, M. R., & Serpe, M. J. (2014). Polymer-based devices for the label-free
detection of DNA in solution: low DNA concentrations yield large
signals. Analytical and Bioanalytical Chemistry, 406(19), 4777-4783.
□ Schild, H. G. (1992). Poly (N-isopropylacrylamide): experiment, theory and
application. Progress in Polymer Science, 17(2), 163-249.
□ Somasundaran, P. (Ed.). (2006). Encyclopedia of Surface and Colloid
Science (Vol. 2). CRC press.

19. □ Zhai, K., Pei, X., Wang, C., Deng, Y., Tan, Y., Bai, Y., ... & Wang, P.
(2019). Water-in-oil Pickering emulsion polymerization of N-isopropyl
acrylamide using starch-based nanoparticles as emulsifier. International
Journal of Biological Macromolecules.
□ Montaser, A. S., Rehan, M., & El-Naggar, M. E. (2019). pH-
Thermosensitive hydrogel based on polyvinyl alcohol/sodium alginate/N-
isopropyl acrylamide composite for treating re-infected
wounds. International Journal of Biological Macromolecules, 124, 1016-
1024.
□ Lanzalaco, S., & Armelin, E. (2017). Poly (n-isopropylacrylamide) and
copolymers: A review on Recent Progresses in Biomedical
Applications. Gels, 3(4), 36.

20. □ Tang, S., Floy, M., Bhandari, R., Dziubla, T., & Hilt, J. (2017).
Development of novel N-isopropylacrylamide (NIPAAm) based hydrogels
with varying content of chrysin multiacrylate. Gels, 3(4), 40.
□ Yan, H., & Tsujii, K. (2005). Potential application of poly (N-
isopropylacrylamide) gel containing polymeric micelles to drug delivery
systems. Colloids and Surfaces , Biointerfaces, 46(3), 142-146.
□ Chen, X., Matsuda, H., & Okuhara, T. (2000). Synthesis of N-
isopropylacrylamide from acrylonitrile and isopropyl alcohol over solid
acids. In Studies in Surface Science and Catalysis(Vol. 130, pp. 2657-
2662). Elsevier.

21. □ Yoshida, R., Sakai, K., Okano, T., & Sakurai, Y. (1995).
Modulating the phase transition temperature and
thermosensitivity in N-isopropylacrylamide copolymer
gels. Journal of Biomaterials Science, Polymer Edition, 6(6),
585-598.
□ Hirotsu, S., Hirokawa, Y., & Tanaka, T. (1987).
Volume‐phase transitions of ionized N‐isopropylacrylamide
gels. The Journal of Chemical Physics, 87(2), 1392-1395.