CARBOMER

Synonyms:
CARBOMER; TEQGEL 400; karbomer; Karbomer 940; Karbomer 980; Karbomer 930; Carbomer 940; Carbomer 980; Carbomer 938 ; Carbopol; Karbopol; Carbomer 841; Poliakrilik Asit; ACRYLIC ACID; 2-Propenoic acid; 79-10-7; Propenoic acid; prop-2-enoic acid; Vinylformic acid; Acroleic acid; Propene acid; Ethylenecarboxylic acid; Carbomer; Polyacrylate; POLYACRYLIC ACID; Propenoate; ACRYLATE; Glacial acrylic acid; Acrylic acid, glacial; Kyselina akrylova; Carbopol 934p; RCRA waste number U008; Acrylic polymer; Carbopol 940; 9003-01-4; Acrylic acid, polymer; Caswell No. 009A; Carbopol; Acrylic resin; Aron; Acido acrilio [Spanish]; Acide acrylique [French]; Antiprex A; Kyselina akrylova [Czech]; UNII-J94PBK7X8S; NSC 4765; Versicol E9; Acrylic acid resin; Acrysol ase-75; Acrysol lmw-20X; Versicol E 7; Acrysol AC 5; CCRIS 737; 2-Propenoic acid, homopolymer; Carbopol 960; Carboset 515; Primal Ase 60; Versicol K 11; Versicol S 25; Viscalex HV 30; Dispex C40; Acrysol WS-24; Cyguard 266; Joncryl 678; Jurimer AC 10H; Jurimer AC 10P; Nalfloc 636; Rohagit SD 15; Carboxy vinyl polymer; Good-rite K 37; Revacryl A 191; Dow Latex 354; Junlon 110; Propenoic acid polymer; Viscon 103; Good-rite K 702; Good-rite K 732; Polyacrylate elastomers; Acrylic acid, polymers; KARBOMER; CARBOMER; KARBOMERE; CARBOMERE 

CARBOMER

Polyacrylic acid

"Carbomer" redirects here. For the exotic molecules expanded by insertion of two-carbon units, see carbo-mer.
Poly(acrylic acid)
Polyacrylic acid.svg
Names
IUPAC name
Poly(acrylic acid)
Other names
PAA, PAAc, Acrysol, Acumer, Alcosperse, Aquatreat, Carbomer, Sokalan
Identifiers
CAS Number    
9003-01-4 check
ChemSpider    
none
ECHA InfoCard    100.115.375 Edit this at Wikidata
KEGG    
C19501 ☒
UNII    
73861X4K5F (8000 MW) ☒
CompTox Dashboard (EPA)    
DTXSID50873988 Edit this at Wikidata
Properties
Chemical formula    (C3H4O2)n
Molar mass    variable
log P    0.25700[1]
Hazards
EU classification (DSD) (outdated)    Irritant Xi
R-phrases (outdated)    R36 R37 R38
NFPA 704 (fire diamond)    
NFPA 704 four-colored diamond
000
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references
Poly(acrylic acid) (PAA; trade name Carbomer) is a synthetic high-molecular weight polymer of acrylic acid. The IUPAC name is poly(1-carboxyethylene). They may be homopolymers of acrylic acid, or crosslinked with an allyl ether of pentaerythritol, allyl ether of sucrose, or allyl ether of propylene. In a water solution at neutral pH, PAA is an anionic polymer, i.e. many of the side chains of PAA will lose their protons and acquire a negative charge. This makes PAAs polyelectrolytes, with the ability to absorb and retain water and swell to many times their original volume.

Dry PAAs are sold as white, fluffy powders that are frequently used as gels in cosmetic and personal care products. Their role in cosmetics is to suspend solid in liquids, prevent emulsions from separating and control the consistency in flow of cosmetics. Carbomer codes (910, 934, 940, 941, and 934P) are an indication of molecular weight and the specific components of the polymer. For many applications PAAs are used in form of alkali metal or ammonium salts, e.g. sodium polyacrylate. In the dry powder form, the positively charged sodium ions are bound to the polyacrylate, however in aqueous solutions the sodium ions can dissociate. Instead of an organized polymer chain, this leads to a swollen gel that can absorb a high amount of water.

Polyacrylic acid is a weak anionic polyelectrolyte, whose degree of ionisation is dependent on solution pH. In its non-ionised form at low pHs, PAA may associate with various non-ionic polymers (such as polyethylene oxide, poly-N-vinyl pyrrolidone, polyacrylamide, and some cellulose ethers) and form hydrogen-bonded interpolymer complexes[2] In aqueous solutions PAA can also form polycomplexes with oppositely charged polymers (for example, chitosan), surfactants, and drug molecules (for example, streptomycin).[3]

Applications
Carbomer and its derivatives are used in disposable diapers,[4] ion exchange resins, adhesives and detergents. Detergents are often copolymers of acrylic acid that can be used in both zeolites and phosphates in washing powder formulations. They are also popular as thickening, dispersing, suspending, and emulsifying agents in pharmaceuticals, cosmetics, and paints. Cross-linked Carbomer has also been used in the processing of household products, including floor cleaners. Acrylic acid is also the main component of Superadsorbent Polymers (SAPs), cross-linked polyacrylates that can absorb and retain more than 100 times of their own weight in liquid. [5] PAA may inactivate the antiseptic chlorhexidine gluconate.[6] The neutralized Carbomer gels are suitable to obtain biocompatible matrices for medical applications such as gels for skin care or skin disease treatment products. PAA films can be deposited on orthopaedic implants to protect them from corrosion. Crosslinked hydrogels of AA and gelatin have also been used as medical glue, which has a high bonding strength. For the development of polymeric matrices which allows controlled delivery rate of active substances, the recent investigations aimed towards the clarification of the conformational changes of the polymeric gel during neutralization, light irradiation, and embedment of gold nanoparticles.[7][8] The US Food and Drug Administration authorised the use of SAPs in packaging with indirect food contact.

Polymer synthesis
Free radical polymerization is still the most common industrial for production of polymers. For the free radical polymerization of acrylic acid, most commonly thermochemical initiators such as potassium persulfate and AIBN are used. The polymerization can take several hours to complete but can be accelerated by drastically increasing the temperature and pressure. PAA is widely used in dispersants and since the molecular weight has a significant impact on the rheological properties and dispersion capacity, it is crucial to have control over the molecular weight distribution. RAFT polymerization was used to obtain PAA with a defined molecular weight, leading to improved dispersion properties. This was only possible in low AA/CTA ratios, at higher ratios transfer to the solvent was observed that had a negative effect on control over the reaction. Block copolymers of PAA have been prepared that are responsive to pH and temperature stimuli, demonstrating the possibility to be used for drug delivery purposes. ATRP has been used to growth PAA brushes from the surface. One reported approach was with surface-initiated ATRP of tert-butyl acrylate that was subsequently deprotected through pyrolysis to form the carboxylic acid. These PAA brushes can form chelate complex with silver and can therefore exhibit antibacterial activity.

See also
Sodium polyacrylate

Molecular Weight of Carbomer:    72.06 g/mol    Computed by PubChem 2.1 (PubChem release 2019.06.18)
XLogP3 of Carbomer:    0.3    Computed by XLogP3 3.0 (PubChem release 2019.06.18)
Hydrogen Bond Donor Count of Carbomer:    1    Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Hydrogen Bond Acceptor Count of Carbomer:    2    Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Rotatable Bond Count of Carbomer:    1    Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Exact Mass of Carbomer:    72.021129 g/mol    Computed by PubChem 2.1 (PubChem release 2019.06.18)
Monoisotopic Mass of Carbomer:    72.021129 g/mol    Computed by PubChem 2.1 (PubChem release 2019.06.18)
Topological Polar Surface Area of Carbomer:    37.3 Ų    Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Heavy Atom Count of Carbomer:5    Computed by PubChem
Formal Charge of Carbomer:    0    Computed by PubChem
Complexity of Carbomer:    55.9    Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Isotope Atom Count of Carbomer:    0    Computed by PubChem
Defined Atom Stereocenter Count of Carbomer:    0    Computed by PubChem
Undefined Atom Stereocenter Count of Carbomer:    0    Computed by PubChem
Defined Bond Stereocenter Count of Carbomer:    0    Computed by PubChem
Undefined Bond Stereocenter Count of Carbomer:    0    Computed by PubChem
Covalently-Bonded Unit Count of Carbomer:    1    Computed by PubChem
Compound  of Carbomer Is Canonicalized    Yes

Acrylic acid is a colorless liquid with a distinctive acrid odor. Flash point 130°F. Boiling point 286°F. Freezing point 53°F. Corrosive to metals and tissue. Prolonged exposure to fire or heat can cause polymerization. If polymerization takes place in a closed container, violent rupture may occur. The inhibitor (usually hydroquinone) greatly reduces the tendency to polymerize.

Acrylic acid, [waste] appears as a colorless liquid with a distinctive acrid odor. Combustible. Flash point 130°F. Boiling point 286°F. Freezing point 121°F. Corrosive to metals and tissue. May polymerize under prolonged exposure to fire or heat. If polymerization occurs in a container violent rupture may occur. Generally shipped with an inhibitor such as hydroquinone to prevent polymerization.