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415464

Sigma-Aldrich

N-Vinylcaprolactam

98%, stabilized

Synonym(s):

1-Ethenylazepan-2-one, 1-Ethenylhexahydro-2H -azepin-2-one, 1-Vinylazepan-2-one

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About This Item

Empirical Formula (Hill Notation):
C8H13NO
CAS Number:
2235-00-9
Molecular Weight:
139.19
EC Number:
218-787-6
MDL number:
MFCD00080693
UNSPSC Code:
12162002
PubChem Substance ID:
24866004
NACRES:
NA.23

Assay

98%

form

solid

contains

~20 ppm HO-TEMPO as stabilizer

bp

128 °C/21 mmHg (lit.)

mp

35-38 °C (dec.) (lit.)

density

1.029 g/mL at 25 °C (lit.)

storage temp.

2-8°C

SMILES string

C=CN1CCCCCC1=O

InChI

1S/C8H13NO/c1-2-9-7-5-3-4-6-8(9)10/h2H,1,3-7H2

InChI key

JWYVGKFDLWWQJX-UHFFFAOYSA-N

Related Categories

General description

N-Vinylcaprolactam (NVCL) is an organo-soluble amphiphilic material that is soluble in solvents like benzene, isobutanol, and isopropanol. It can be used in the preparation of poly(NVCL) by free-radical polymerization at a temperature higher than its melting point.

Application

NVCL forms a temperature responsive polymer, which can be used for a variety of biomedical applications.

Pictograms

Health hazardExclamation mark
GHS08,GHS07

Signal Word

Danger

Hazard Classifications

Acute Tox. 4 Dermal - Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Sens. 1 - STOT RE 1

Target Organs

Liver,Upper respiratory tract

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 1

Flash Point(F)

213.8 °F - closed cup

Flash Point(C)

101 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Synthesis of N-vinylcaprolactam polymers in water-containing media
Lozinsky VI, et al.
Polymer, 41(17), 6507-6518 (2000)
Oleksandra Zavgorodnya et al.
Journal of colloid and interface science, 506, 589-602 (2017-08-02)
We report nanothin temperature-responsive hydrogel films of poly(N-vinylcaprolactam) nanoparticles (νPVCL) with remarkably high loading capacity for topical drug delivery. Highly swollen (νPVCL)
Simone F Medeiros et al.
Drug development and industrial pharmacy, 43(9), 1519-1529 (2017-04-25)
Poly(N-vinylcaprolactam) (PNVCL) and poly(N-vinylcaprolactam-co-acrylic acid) (poly(NVCL-co-AA)) were synthesized by solution-free radical polymerization and displayed thermo-responsive behavior, with lower critical solution temperatures (LCSTs) of 35 °C and 39 °C, respectively. The incorporation of AA unities made the poly(NVCL-co-AA) sensitive to both pH and
Poly (N-vinylcaprolactam), a comprehensive review on a thermoresponsive polymer becoming popular
Cortez-Lemus NA and Licea-Claverie A
Progress in Polymer Science, 53(5), 1-51 (2016)
Serap Durkut et al.
Artificial cells, nanomedicine, and biotechnology, 45(8), 1665-1674 (2017-01-13)
In this study, we synthesized poly(N-vinylcaprolactam)-g-collagen (PNVCL-g-Col) by grafting collagen with carboxyl group-terminated thermosensitive PNVCL-COOH. The resulting biopolymer was evaluated for its structural, thermal, and rheological properties. Aqueous solutions of PNVCL-g-Col exhibited a temperature-dependent phase transition around human physiological temperature
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