BRONOPOL

CASNO:52-51-7

 synonyms:

Bronopol

The first reported synthesis of bronopol was in 1897.[citation needed]

Bronopol was invented by The Boots Company PLC in the early 1960s and first applications were as a preservative for pharmaceuticals. Due to its low mammalian toxicity at in-use levels and high activity against bacteria, especially Gram-negative species,[1] bronopol became popular as a preservative in many consumer products such as shampoos and cosmetics. It was subsequently adopted as an antimicrobial in other industrial environments such as paper mills, oil exploration, and production facilities, as well as cooling water disinfection plants.

Applications

The use of bronopol in personal care products (cosmetics, toiletries) has declined since the late 1980s due to the potential formation of nitrosamines. While bronopol is not in itself a nitrosating agent, under conditions where it decomposes (alkaline solution and/or elevated temperatures) it can liberate nitrite and low levels of formaldehyde and these decomposition products can react with any contaminant secondary amines or amides in a personal care formulation to produce significant levels of nitrosamines (due to the toxicity of these substances, the term 'significant' means levels as low as 10s of parts per billion).

Manufacturers of personal care products are therefore instructed by regulatory authorities to avoid the formation of nitrosamines which might mean removing amines or amides from the formulation, removing bronopol from a formulation, or using nitrosamine inhibitors.

Bronopol has been restricted for use in cosmetics in Canada.[3]

At temperatures above 140 °C, bronopol decomposes exothermically releasing hydrogen bromide and oxides of nitrogen.

Bronopol is poorly soluble in non-polar solvents but shows a high affinity for polar organic solvents.

Bronopol is used by consumers, by professional workers (widespread uses) and in formulation or re-packing.

Bronopol is a Standardized Chemical Allergen. The physiologic effect of bronopol is by means of Increased Histamine Release, and Cell-mediated Immunity. The chemical classification of bronopol is Allergens.

Bronopol, or 2-Bromo-2-nitro-1,3-propanediol, is an inorganic compound with wide-spectrum antimicrobial properties. First synthesized in 1897, bronopol was primarily used as a preservative for pharmaceuticals and was registered in the United States in 1984 for use in industrial bactericides, slimicides and preservatives [F13]. Bronopol is used as a microbicide or microbiostat in various commercial and industrial applications, including oil field systems, air washer systems, air conditioning or humidifying systems, cooling water systems, papermills, absorbent clays, metal working fluids, printing inks, paints, adhesives and consumer products [F13]. Compared to other aliphatic halogen-nitro compounds, bronopol is more stable to hydrolysis in aqueous media under normal conditions [A32792]. The inhibitory activity against various bacteria, including _Pseudomonas aeruginosa_, was demonstrated _in vitro_ [A32792]. Bronopol is approved for use in antibacterial OTC products in Canada.

2-BROMO-2-NITROPROPANE-1,3-DIOL is a white crystals. Ignite easily and burn readily. May detonate under strong shock. Decomposes when heated, evolving toxic gases. Toxic by skin absorption, inhalation or ingestion.

In 2005-06, it was the 15th-most-prevalent allergen in patch tests (3.4%) of people with suspected allergic contact dermatitis. It is used as a substitute for formaldehyde, a disinfectant and preservative, in solvents. It is prevalent in skin and personal care products and topical medications.

Properties: Biocidal products containing active ingredient Bronopol are used for the preservation of industrial and consumer products and for conditioning industrial and process water. Bronopol is soluble in water and compatible with proteins and non-ionic. Mantarsal activity is poor, poor stability over pH 8, associated with nitrosamine formation, detectable formaldehyde release. Typical usage concentration is between 0,01-0,04%.

Solubility and miscibility: Bronopol can be easily incorporated into aqueous formulation systems. Concentrated aqueous solutions tend to crystallize at low temperatures. Bronopol dissolves poorly in polar solvents, but organic polar solvents show a high degree of interest.

In non-aqueous systems, it is possible to achieve an effective level of Bronopol by using a suitable carrier solvent with careful selection of the raw materials.

Storage stability: When stored at ambient temperature, sealed packaging, Bronopol crystal types are stable for at least 3 years and liquid formulations are stable for at least 2 years. When aqueous solutions of crystalline material are prepared, bronopol is most stable when the pH of the system is acidic. In the presence of buffers, Bronopol's concentration solutions tend to be self-stabilizing. The best pH for stability is around 4 and the data obtained from studies in dilute solutions of Bronopol show that the lifetime at pH = 4 and room temperature is more than 5 years. At pH and temperature increases, aqueous bronopol solutions become less stable.

Compatibility: Indicates that the concentrated aqueous solutions (20%) of the bronopol solutions (321 type) are compatible with solid PVC, Polyethylene (XDG33), plasticized PVC, silicone rubber, nylon and polypropylene in stainless steel. A diluted aqueous bronopol solution (0.02%) (representative of the level of use); stainless steel (321), aluminum, brass, copper, solid PVC, polyethylene (WJ611) and polyethylene (XD633).

Antimicrobial activity: Bronopol has a complex style of antimicrobial action. It has a broad spectrum against all groups of Bronopol bacteria containing bacteria-reducing anaerobic sulphate. The majority of bacteria are stopped between 6.25 and 50 ppm.

More doses are needed to reduce the activity of Bronopol's fungi more and more generally. Most yeasts and molds require about 400 to 1600 ppm search. This procedure can not always control bronchopneumic dosages alone. It is not like this, it can be used with other assets. The Bronopol industry has pressure diagnostics:

Paper industry biocides: Processes of water treatment and mill (grinding). Calcium carbonate processing paper mill (grinding) additive preservative.

Water and oil field biocides:

Increasing oil recovery and conditioning cleaning waters such as cooling towers.

Bronopol is capable of controlling microbial contamination (in piercing mud). Tests show that you can clear all levels of contamination.

Industrial product enclosure:

Technical files such as polymer emulsion adhesives and motor materials. Bronopol is a very low level in a multidimensional arrangement.

Bronopol, or 2-Bromo-2-nitro-1,3-propanediol, is an inorganic compound with wide-spectrum antimicrobial properties. First synthesized in 1897, bronopol was primarily used as a preservative for pharmaceuticals and was registered in the United States in 1984 for use in industrial bactericides, slimicides and preservatives [F13]. Bronopol is used as a microbicide or microbiostat in various commercial and industrial applications, including oil field systems, air washer systems, air conditioning or humidifying systems, cooling water systems, papermills, absorbent clays, metal working fluids, printing inks, paints, adhesives and consumer products [F13]. Compared to other aliphatic halogen-nitro compounds, bronopol is more stable to hydrolysis in aqueous media under normal conditions [A32792]. The inhibitory activity against various bacteria, including _Pseudomonas aeruginosa_, was demonstrated _in vitro_ [A32792]. Bronopol is approved for use in antibacterial OTC products in Canada.

2-BROMO-2-NITROPROPANE-1,3-DIOL is a white crystals. Ignite easily and burn readily. May detonate under strong shock. Decomposes when heated, evolving toxic gases. Toxic by skin absorption, inhalation or ingestion.

In 2005-06, it was the 15th-most-prevalent allergen in patch tests (3.4%) of people with suspected allergic contact dermatitis. It is used as a substitute for formaldehyde, a disinfectant and preservative, in solvents. It is prevalent in skin and personal care products and topical medications.

Properties: Biocidal products containing active ingredient Bronopol are used for the preservation of industrial and consumer products and for conditioning industrial and process water. Bronopol is soluble in water and compatible with proteins and non-ionic. Mantarsal activity is poor, poor stability over pH 8, associated with nitrosamine formation, detectable formaldehyde release. Typical usage concentration is between 0,01-0,04%.

Solubility and miscibility: Bronopol can be easily incorporated into aqueous formulation systems. Concentrated aqueous solutions tend to crystallize at low temperatures. Bronopol dissolves poorly in polar solvents, but organic polar solvents show a high degree of interest.

In non-aqueous systems, it is possible to achieve an effective level of Bronopol by using a suitable carrier solvent with careful selection of the raw materials.

Storage stability: When stored at ambient temperature, sealed packaging, Bronopol crystal types are stable for at least 3 years and liquid formulations are stable for at least 2 years. When aqueous solutions of crystalline material are prepared, bronopol is most stable when the pH of the system is acidic. In the presence of buffers, Bronopol's concentration solutions tend to be self-stabilizing. The best pH for stability is around 4 and the data obtained from studies in dilute solutions of Bronopol show that the lifetime at pH = 4 and room temperature is more than 5 years. At pH and temperature increases, aqueous bronopol solutions become less stable.

Compatibility: Indicates that the concentrated aqueous solutions (20%) of the bronopol solutions (321 type) are compatible with solid PVC, Polyethylene (XDG33), plasticized PVC, silicone rubber, nylon and polypropylene in stainless steel. A diluted aqueous bronopol solution (0.02%) (representative of the level of use); stainless steel (321), aluminum, brass, copper, solid PVC, polyethylene (WJ611) and polyethylene (XD633).

Antimicrobial activity: Bronopol has a complex style of antimicrobial action. It has a broad spectrum against all groups of Bronopol bacteria containing bacteria-reducing anaerobic sulphate. The majority of bacteria are stopped between 6.25 and 50 ppm.

More doses are needed to reduce the activity of Bronopol's fungi more and more generally. Most yeasts and molds require about 400 to 1600 ppm search. This procedure can not always control bronchopneumic dosages alone. It is not like this, it can be used with other assets. The Bronopol industry has pressure diagnostics:

Paper industry biocides: Processes of water treatment and mill (grinding). Calcium carbonate processing paper mill (grinding) additive preservative.

Water and oil field biocides:

Increasing oil recovery and conditioning cleaning waters such as cooling towers.

Bronopol is capable of controlling microbial contamination (in piercing mud). Tests show that you can clear all levels of contamination.

Industrial product enclosure:

Technical files such as polymer emulsion adhesives and motor materials. Bronopol is a very low level in a multidimensional arrangement.

 Bronopol (INN; chemical name 2-bromo-2-nitro-1,3-propanediol) is an organic compound that is used as an antimicrobial. It is a white solid although commercial samples appear yellow.

CAS Registry Number: 52-51-7

Bronopol was invented by The Boots Company PLC in the early 1960s and first applications were as a preservative for pharmaceuticals. Due to its low mammalian toxicity at in-use

 levels and high activity against bacteria, especially Gram-negative species, bronopol became popular as a preservative in many consumer products such as shampoos and cosmetics.

It was subsequently adopted as an antimicrobial in other industrial environments such as paper mills, oil exploration, and production facilities, as well as cooling water disinfection 

plants.

2-Bromo-2-nitropropane-1,3-diol

2-bromo-2-nitropropane-1,3-diol appears as white crystals. Ignite easily and burn readily. May detonate under strong shock. Decomposes when heated, evolving toxic gases. Toxic by skin 

absorption, inhalation or ingestion.

Bronopol, or 2-Bromo-2-nitro-1,3-propanediol, is an organic compound with wide-spectrum antimicrobial properties. First synthesized in 1897, bronopol was primarily used as a

 preservative for pharmaceuticals and was registered in the United States in 1984 for use in industrial bactericides, slimicides and preservatives. Bronopol is used as a microbicide 

or microbiostat in various commercial and industrial applications, including oil field systems, air washer systems, air conditioning or humidifying systems, cooling water systems, 

papermills, absorbent clays, metal working fluids, printing inks, paints, adhesives and consumer products. Compared to other aliphatic halogen-nitro compounds, bronopol is more stable 

to hydrolysis in aqueous media under normal conditions. The inhibitory activity against various bacteria, including Pseudomonas aeruginosa, was demonstrated in vitro. The agent is 

largely available commercially as an antibacterial for a variety of industrial purposes while it is predominantly available for purchase as a pet animal litter antibacterial at the 

domestic consumer level. Nevertheless, ongoing contemporary re-evaluations of bronopol use in large markets such as Canada now place various compositional and product restrictions

 on the use of the agent in cosmetic products and in other products where it may not primarily be used in the role of a non-medicinal preservative antimicrobial.

Bronopol is produced by the bromination of di(hydroxymethyl)nitromethane, which is derived from nitromethane by a nitroaldol reaction.World production increased from the tens 

of tonnes in the late 1970s to current estimates in excess of 5,000 tonnes. Manufacturing today is the business of low cost producers, mainly in China.

Applications

Bronopol is used in consumer products as an effective preservative agent, as well as a wide variety of industrial applications (almost any industrial water system is a potential

 environment for bacterial growth, leading to slime and corrosion problems - in many of these systems bronopol can be a highly effective treatment).

The use of bronopol in personal care products (cosmetics, toiletries) has declined since the late 1980s due to the potential formation of nitrosamines. While bronopol is not in itself 

a nitrosating agent, under conditions where it decomposes (alkaline solution and/or elevated temperatures) it can liberate nitrite and low levels of formaldehyde and these decomposition

 products can react with any contaminant secondary amines or amides in a personal care formulation to produce significant levels of nitrosamines (due to the toxicity of these substances,

 the term 'significant' means levels as low as 10s of parts per billion).

Manufacturers of personal care products are therefore instructed by regulatory authorities to avoid the formation of nitrosamines which might mean removing amines or amides from the

 formulation, removing bronopol from a formulation, or using nitrosamine inhibitors.

Bronopol has been restricted for use in cosmetics in Canada.[3]

Physical and chemical properties

Appearance

Bronopol is supplied as crystals or crystalline powder, which may vary from white to pale yellow in colour depending on the grade. The yellow coloration is due to chelation of iron

 during the manufacturing process.

Melting point

As a pure material, bronopol has a melting point of about 130 °C. However, due to its polymorphic characteristics, bronopol undergoes a lattice rearrangement at 100 to 105 °C and this 

can often be wrongly interpreted as the melting point.

At temperatures above 140 °C, bronopol decomposes exothermically releasing hydrogen bromide and oxides of nitrogen.

Solubility

Bronopol is readily soluble in water; the dissolution process is endothermic. Solutions containing up to 28% w/v are possible at ambient temperature.

Bronopol is poorly soluble in non-polar solvents but shows a high affinity for polar organic solvents.

Solubilities at 22–25 °C

Solvent %w/v

Water 28

Methanol 89

Ethanol 56

Isopropanol 41

Liquid Paraffin <0.5

Partition coefficient

Study of the solubility data shows that bronopol has a high affinity for polar rather than non-polar environments. In two-phase systems, bronopol partitions preferentially into 

the polar (usually aqueous) phase.

Partition coefficients at 22–24 °C

Solvent Combination Partition Co-efficient

Hexanol/Water 0.74

Alkane|Liquid Paraffin/Water 0.043

Chloroform/Water 0.068

Stability in aqueous solution

In aqueous solutions, bronopol is most stable when the pH of the system is on the acid side of neutral. Temperature also has a significant effect on stability in alkaline systems.

Degradation

Under extreme alkaline conditions, bronopol decomposes in aqueous solution and very low levels of formaldehyde are produced. Liberated formaldehyde is not responsible for the

 biological activity associated with bronopol. Other decomposition products detected after bronopol breakdown are bromide ion, nitrite ion, bromonitroethanol and 

2-hydroxymethyl-2-nitropropane-1,3-diol.

Allergy

Patch test

In 2005–2006, it was the 15th-most-prevalent allergen in patch tests (3.4%) of people with suspected allergic contact dermatitis. It is used as a substitute for formaldehyde,

 a disinfectant and preservative, in solvents. It is prevalent in skin and personal care products and topical medications.

1,3-Propanediol, 2-bromo-2-nitro-

2-Bromo-2-nitro-1,3-propanediol

2-Nitro-2-bromo-1,3-propanediol

beta-Bromo-beta-nitrotrimethyleneglycol

Bronidiol

Bronocot

Bronopolu

Bronopolum

Bronosol

Bronotak

Lexgard bronopol

Onyxide 500

Translated names

2-brom-2-nitropropan-1,3-diol (cs)

2-brom-2-nitropropan-1,3-diolis (lt)

2-brom-2-nitropropān-1,3-diols (lv)

2-Brom-2-nitroropan-1,3-diol (de)

2-Bromi-2-nitropropaani-1,3-dioli (fi)

2-bromo-2-nitropropaan-1,3-diool (et)

2-bromo-2-nitropropan-1,3-diol (hr)

2-bromo-2-nitropropan-1,3-diolo (it)

2-bromo-2-nitropropane-1,3-diol (fr)

2-bromo-2-nitropropano-1,3-diol (es)

2-broom-2-nitropropaan-1,3-diol (nl)

2-bróm-2-nitropropán-1,3-diol (hu)

2-βρωμο-2-νιτρο-προπανο-1,3-διόλη (el)

2-бромо-2-нитропропан-1,3-диол (bg)

bronopol (cs)

bronopol (DCI) (es)

bronopol (INN) (cs)

bronopol (INN); 2-bromo-2-nitropropane-1,3-diol (fr)

Bronopoli (fi)

Bronopoli (INN) (fi)

Bronopolis (lt)

bronopolis (INN) (lt)

Bronopols (lv)

bronopols (INN) (lv)

Bronopool (et)

bronopool (INN) (et)

Бронопол (bg)

Biocidal active substances

бронопол (INN) (bg)

IUPAC names

2 bromo-2-nitropropane-1,3-diol

2-Brom-2-Nitropropane-1,3-Diol

2-bromo-2-nitro-1,3-propanediolbronopol

2-bromo-2-nitro-propane-1,3-diol

2-bromo-2-nitropropane-

2-bromo-2-nitropropane-1,3-diol bronopol (INN)

2-bromo-2nitropropane-1,3-diol

BromnitropropandiolBronopolRD_CLP_52-51-7_1,3-Propanediol, 2-bromo-2-nitro-_V1_20180110_TS

Morpholin-4-yl morpholine-4-carbodithioate

Trade names

2-Bromo-2-nitropropane-1,3-diol (chemical name)

BNPD 

Bronopol (common name)

Bronopol strongly inhibits the growth of Gram positive and Gram negative

Bacteria. It also is highly effective in eliminating the growth of Pseudomonas

species, including pathogenic Pseudomonas aeruginosa. Its applications

include cosmetic, pharmaceutical, toiletry and household products.

When the control of yeasts and molds is required, Bronopol can be combined

with other antimicrobials that provide additional anti-fungicidal activity.

Blends of Bronopol and Parabens give excellent coverage of all microbial

spectra. High compatibility with cationic, nonionic, anionic and amphoteric

surfactants and many other raw materials, including other preservatives,

makes Bronopol a very versatile product.

It is soluble in water and other polar solvents such as propylene glycol and

isopropanol. We recommend adding Bronopol to aqueous phase as it will

prevent the primary bacterial growth that takes place in this medium.

Bronopol breaks down under alkaline conditions and elevated temperatures

and should not be used in combination with secondary amines. This can lead

to an undesired chemical reaction and formation of nitrosamines. For cold

process products, we recommend adding Bronopol from the onset of the

formulation preparation process.

The recommended use level for Bronopol ranges from 0.03% to 0.1%.

BRONOPOL

MINIMUM INHIBITION CONCENTRATIONS (MIC) FOR BRONOPOL

Microorganism Type MIC (ppm)

Escherichia coli Bacteria Gram - 15

Pseudomonas aeruginosa Bacteria Gram - 15

Burkholderia cepacia Bacteria Gram - 15

Staphylococcus aureus Bacteria Gram + 10

Staphylococcus epidermidis Bacteria Gram + 15

Aspergillus niger Mold 2000

Candida albicans Yeast 1250

Other names: 1,3-Propanediol, 2-bromo-2-nitro-; Bronocot; Onyxide 500; 2-Bromo-2-nitro-1,3-propanediol; 2-Bromo-2-nitropropane-1,3-diol; Bronosol; 2-Nitro-2-bromo-1,3-propanediol;

 2-Bromo-2-nitropropan-1,3-diol; β-Bromo-β-nitrotrimethyleneglycol; Bronopolu; Bronotak; Bioban; Bronidiol; Canguard 409; Lexgard bronopol; Myacide AS plus; Myacide BT; NSC 141021; 

Myacide Pharma BP

Bronopol

CAS number:52-51-7

Gross formula:C3H6BrNO4

Appearance:white or beige crystalline substance.

Chemical name and synonym:2-Bromo-2-nitro-1,3-propanediol, Bronopol.

Physical and chemical properties:

Molecular weight 199.99 g / mol

Melting point 124-129 ºC

Solubility in water 25 g / 100 ml (22 ºC)

Description:

Bronopol is a white, odorless crystalline substance that melts at about 130 ºC. It is readily soluble in water, lower alcohols, acetic acid, diethyl ether and ethyl acetate, but poorly soluble in chloroform, acetone and practically insoluble in hydrocarbon solvents. The values ​​of the solubility of bronopol in some solvents are as follows (w / v% at 22-25 ° C): water 28; methyl alcohol 89; ethyl alcohol 56; isopropyl alcohol 41; ethylene glycol 61; methylcarbitol 54; 1,2-propylene glycol 52; dipropylene glycol 48; polyethylene glycol 300; diethyl sebacate 10; isopropyl myristate, mineral oil and vegetable oils less than 0.5. Aqueous solutions of a pure compound have a pH of 5.0-5.5, which is explained by the mobility of hydroxyl hydrogen atoms. Solid compound can be stored for 3 years or longer, it is not influenced by factors such as daylight, humidity (up to 90%) and temperature (up to 45 ° C). However, an aqueous solution of Bronopol is stable only in the cold, provided that the acidity is high enough. An increase in pH and temperature leads to the decomposition of the compound as a result of the decomposition of formaldehyde. The initial process of decomposition of bronopol appears to be a retroaldol reaction with the release of formaldehyde and the formation of bromonitroethanol.

Bromonitroethanol itself is significantly less stable than bronopol, and in the range of conditions studied, its maximum concentration did not exceed 0.5% of the initial concentrations of bronopol. At the same time, a second-order reaction occurs with the participation of bronopol and formaldehyde to obtain 2-hydroxymethyl-2-nitro-1,3-propanediol. The antimicrobial activity of bronopol is mainly due to the presence of electron-deficient bromine atoms in the molecules, which exhibit oxidizing properties, and not the ability to release formaldehyde. The mechanism of the antimicrobial action of bronopol consists of cross-linking of sulfhydride groups of dehydrogenase enzymes that occur on the surface of microbial cells. Disulfide bridges block the metabolism of microorganisms.

Application:

Bronopol is used as a preservative in various cosmetic and household products due to its high activity against gram-negative bacteria, especially Pseudomonas aeruginosa and other pseudomonads. These organisms are common water dwellers and can cause pollution and deterioration problems. Bronopol is an effective antibacterial preservative in a wide pH range. It is stable at acidic pH values ​​and is also useful as a labile antibacterial preservative in an alkaline environment. Due to its broad spectrum antibacterial activity, Bronopol can also be used as an active agent, for example in aerosol preparations.

Receiving:

The method for producing bronopol includes loading the reaction vessel with water, bromopicrin, nitromethane and paraformaldehyde, gradually supplying the base to the reaction vessel with stirring, bringing the reaction to completion and separating bronopol from the aqueous reaction mixture.

Bronopol products are currently registered for use in oilfield systems, air purification systems, industrial water treatment systems, laboratory water baths, coatings, emulsions, air conditioning / humidification systems, pulp and paper industry systems, metalworking cutting fluids, and also consumer / institutional products.

Action on the body:

Bronopol (2-bromo-2-nitropropane-1,3-diol) is a bactericide with limited effectiveness against fungal organisms. It is active against Pseudomonas species and should be used at a pH of 5 to 8.8, below the application temperature of 45 ° C. Bronopol has a complex mechanism of action that attacks thiol groups in cells, suppressing respiration and cellular metabolism.

Research indicates that bronopol is a corrosive eye irritant and moderate to severe skin irritant in rabbits. The fate of the environment and the ecological consequences of the use of Bronopol are moderately highly toxic for estuarine / marine invertebrates; slightly toxic to marine fish; slightly toxic to birds with acute oral ingestion. However, no quantitative risk assessment has been carried out. The risk to the aquatic environment is being addressed under the NPDES permitting program by the Water Resources Authority. It is now required that labels on all products containing Bronopol meet NPDES requirements.

Toxicological data:

Acute toxicity:

LD50 oral - rat - 180 mg / kg

LD50 cutaneous - rat - 1.600 mg / kg

Oral (LD50): 270 mg / kg [Mouse].

Oral (LD50): 250 mg / kg [Dog].

Ecotoxicity:

Fish toxicity LC50 - Oncorhynchus mykiss (rainbow trout) - 20 mg / l - 96 h

Toxicity to Daphnia and other aquatic invertebrates.

EC50 - Daphnia magna (large daphnia) - 1.6 mg / l - 48 h

Very toxic to aquatic life.

Bacteria: Phytobacterium phosphoreum: EC50 = 0.41-0.90 mg / l; 5.15.30 minutes; Microtoxic test; 15 degrees Celsius.

Bronopol

Bronopol is a fairly popular broad-spectrum preservative, which allows it to be used in some formulations as the only preservative. It is effective at low concentrations; as a rule, dosages used in cosmetics are below the maximum allowable limit of 0.1%, established by law.

The mechanism of the antimicrobial action of bronopol is quite complex, and, as a rule, it is not associated with the release of formaldehyde. That is why it is considered that it is a mistake to classify this preservative as a typical formaldehyde donor. Nevertheless, it cannot be denied that formaldehyde is nevertheless formed during the decomposition of bronopol, and the presence of cross-sensitivity to bronopol with an established allergy to formaldehyde takes place. However, the release of formaldehyde does not occur at the same rate and in the same amount under different conditions.

The main factors affecting the destruction of bronopol are pH, sunlight and temperature. It was found that with the addition of citric acid, which lowers the pH, the decomposition of bronopol in aqueous solutions slows down, which is quite natural, and an increase in temperature and exposure to sunlight increases the rate of decomposition. These facts are taken into account when formulating recipes.

There are few quantitative data on the destruction of bronopol - much less than for typical formaldehyde donors, but they are still there; the highest concentration of formaldehyde in alkaline compounds, which is quite natural, but they are not so high as to cause concern or put a warning about the presence of formaldehyde in the marking. The pH range from 5 to 6 can be considered quite favorable for the preservative's behavior and for the skin.

Bronopol, like other preservatives, can cause the development of symptoms of contact dermatitis, but in most cases it does not belong to the leaders, but rather an outsider. A different situation is observed only in case of serious skin diseases, such as chronic eczema or atopic dermatitis, in which the normal barrier function of the skin is disrupted, and the frequency of using special cosmetics designed to relieve symptoms is increased, which leads to an increased risk of developing sensitization. But the specificity of allergic reactions to bronopol is not due to formaldehyde, but to other products of its decay, such as 2-bromoethanol, 2-bromo-2-nitroethanol and bromonitromethane.

The connection between the use of bronopol in cosmetics and the potential for the formation of carcinogenic nitrosamines theoretically exists (and if the established precautions are not followed, it can be realized in practice), but for this, restrictions are introduced to minimize these risks [1]... Nitrosamines are found almost everywhere in the environment; moreover, they are formed in the human digestive tract as a result of the reaction between secondary amines or amides and nitrite ions. Bronopol itself is not a nitrosating agent, but under conditions under which it decomposes (alkaline environment and / or elevated temperature), it can release nitrite ions, potentially capable of producing nitrosamines - if anything, because for this reaction there is only nitrite is not enough. Accordingly, bronopol is not used where there is a risk of formation of nitrosamines, and cosmetic raw materials, which may contain trace amounts of secondary amines or amides, undergo thorough cleaning and strict control

Bronopol ( INN ; kimyasal adı 2-bromo-2-nitro-1,3-propandiol ), antimikrobiyal olarak kullanılan organik bir bileşiktir . Ticari örnekler sarı görünse de beyaz bir katıdır.

Bildirilen ilk bronopol sentezi 1897'de idi. [ Alıntı gerekli ]

Bronopol 1960'lı yılların başında The Boots Company PLC tarafından icat edildi ve ilk uygulamalar farmasötikler için bir koruyucu idi . Kullanımdaki düzeylerde düşük memeli toksisitesi ve bakterilere , özellikle Gram-negatif türlere karşı yüksek aktivitesinden dolayı , [1] bronopol şampuan ve kozmetik gibi birçok tüketici ürününde koruyucu olarak popüler oldu . Daha sonra kağıt fabrikaları , petrol arama gibi diğer endüstriyel ortamlarda antimikrobiyal olarak kabul edildi. ve üretim tesislerinin yanı sıra soğutma suyu dezenfeksiyon tesisleri.

Uygulamalar

Kişisel bakım ürünlerinde ( kozmetik , tuvalet malzemeleri ) bronopol kullanımı , potansiyel nitrozamin oluşumu nedeniyle 1980'lerin sonundan bu yana azalmıştır . Bronopol kendi başına bir nitrozlama maddesi olmasa da, ayrıştığı koşullar altında ( alkalin çözeltisi ve / veya yüksek sıcaklıklar) nitrit ve düşük seviyelerde formaldehit açığa çıkarabilir ve bu ayrışma ürünleri kişisel bakımdaki herhangi bir kirletici ikincil amin veya amid ile reaksiyona girebilir önemli seviyelerde nitrozamin üretmek için formülasyon (bu maddelerin toksisitesi nedeniyle, 'önemli' terimi milyarda 10s kadar düşük seviyeler anlamına gelir).

Kişisel bakım ürünleri imalatçıları bu nedenle düzenleyici makamlar tarafından formülasyondan amin veya amidlerin uzaklaştırılması, bronopolün bir formülasyondan çıkarılması veya nitrosamin inhibitörlerinin kullanılması anlamına gelebilecek nitrozaminlerin oluşumundan kaçınmaları için talimat verilir.

Bronopol'un Kanada'daki kozmetik ürünlerinde kullanımı kısıtlanmıştır. [3]

140 ° C'nin üzerindeki sıcaklıklarda bronopol, egzotermik olarak hidrojen bromür ve azot oksitleri salarak ayrışır .

Bronopol, polar olmayan çözücülerde az çözünür ancak polar organik çözücüler için yüksek bir afinite gösterir.

Bronopol, Standartlaştırılmış bir Kimyasal Allerjendir. Bronopanın fizyolojik etkisi, Artan Histamin Salımı ve Hücre-aracılı Bağışıklıktır. Bronopolün kimyasal sınıflandırması Allergens'dir.

Bronopol veya 2-Bromo-2-nitro-1,3-propandiol, geniş spektrumlu antimikrobiyal özelliklere sahip inorganik bir bileşiktir. İlk olarak 1897'de sentezlenen bronopol, 1984 yılında ABD'de, endüstriyel bakterisit, inceltici ve koruyucu maddeler için koruyucu olarak kullanıldı [F13]. Bronopol, petrol sahası sistemleri, hava yıkama sistemleri, klima veya nemlendirme sistemleri, soğutma suyu sistemleri, papermiller, emici killer, tüketici ürünleri de dahil olmak üzere çeşitli ticari ve endüstriyel uygulamalar için bir mikrobisid veya mikrobiyostat olarak kullanılır [F13]. Diğer alifatik halojen-nitro bileşiklerine kıyasla, bronopol normal koşullarda sulu ortamda hidrolize daha stabildir [A32792]. _Pseudomonas aeruginosa dahil olmak üzere çeşitli bakterilere karşı inhibitör aktivite, in vitro olarak gösterilmiştir [A32792]. Bronopol, Kanada'daki antibakteriyel OTC ürünlerinde kullanılmak üzere onaylanmıştır.

2-BROMO-2-NITROPROPANE-1,3-DIOL beyaz kristallerdir. Kolayca tutuşturun ve kolayca yanık. Güçlü şok altında patlayabilir. Isındığında zehirli gazları açığa çıkarır. Cilt emilimi, inhalasyon veya yutulmasıyla toksiktir.

2005-06'da, alerjik kontakt dermatitten şüphelenilen kişilerin yama testlerinde (% 3.4) 15. en yaygın allerjen oldu. Solventlerde formaldehit, dezenfektan ve koruyucu yerine kullanılır. Cilt ve kişisel bakım ürünlerinde ve topikal ilaçlarda yaygındır.

Özellikler: Aktif madde Bronopol içeren biosidal ürünler, endüstriyel ve tüketici ürünlerinin muhafazası için ve endüstriyel ve proses suyunun şartlandırılmasında kullanılır. Bronopol, suda çözünürdür ve proteinler ve non iyoniklerle uyumludur. Mantarsal aktivitesi zayıftır, pH 8'in üzerinde zayıf stabilite gösterir, nitrozamin oluşumuyla ilişkilidir, algılanabilir formaldehit salar. Tipik kullanım konsantrasyonu % 0,01-0,04 arasındadır.

Çözünürlük ve karışabilirlik: Bronopol kolaylıkla sulu formülasyon sistemlerine dahil edilebilir. Konsantre sulu çözeltileri düşük sıcaklıkta kristallenmeye eğilim gösterirler. Bronopol polar olmayan çözücülerde zayıf bir şekilde çözünür, fakat organik polar solventlere yüksek ilgi gösterir.

Sulu olmayan sistemlerde, hammaddelerin dikkatli bir seçimiyle uygun taşıyıcı bir solvent kullanımıyla, Bronopol'ün etkili düzeyini elde etmek mümkündür.

Depolama kararlılığı: Ortam sıcaklığında, kapalı ambalajında depolandığında, Bronopol'ün kristal tipleri en az 3 yıl, sıvı formülasyonları en az 2 yıl stabildir. Kristal maddenin sulu çözeltileri hazırlandığında, bronopol en çok sistemin pH'ı asidik olduğunda kararlıdır. Tamponların varlığında, Bronopol'ün konsantre çözeltileri kendi kendini kararlı yapmaya eğilim gösterir. Stabilite için en iyi pH, 4 civarındadır ve Bronopol'ün seyreltik çözeltilerindeki çalışmalardan elde edilen veriler, pH=4'de ve oda sıcaklığında ömrünün 5 yıldan fazla olduğunu ortaya koyar. pH ve sıcaklık artışlarında sulu bronopol çözeltileri daha az kararlı olurlar.

Uyumluluk: Bronopol çözeltilerinin (%20) konsantre sulu çözeltilerinin paslanmaz çelikte (321 tipi), katı PVC, Polietilen (XDG33), plastikleşmiş PVC, silikon kauçuk, nylon ve polipropilenle uyumlu olduğunu gösterir. Seyreltilmiş sulu bir bronopol çözeltisi (% 0,02)(kullanım düzeyinin temsilcisi); paslanmaz çelik (321), alüminyum, prinç, bakır, katı PVC, polietilen (WJ611) ve polietilen (XD633) ile uyumlu olduğu görülür.

Antimikrobiyal aktivite: Bronopol, antimikrobiyal hareketin kompleks bir tarzına sahiptir. Bakteri azaltan anaerobik sülfat içeren Bronopol bakterilerin bütün gruplarına karşı geniş bir spektruma sahiptir. Bakterilerin çoğunluğu 6,25 ve 50 ppm arasında durdurulur.

Bronopol'ün mantarlara karşı aktivitesi daha değişiktir ve genel olarak çoğalmayı durdurmak için daha yüksek dozlar gerekir. Maya ve küflerin çoğunun durdurulmasında 400-1600 ppm aralığına ihtiyaç duyulur. Bununla birlikte bozucu mantar 6400 ppm'in aşırısını ister ve bu yüzden her zaman tek başına Bronopol'le ekonomik dozaj oranları kontrol edilemez. Bu gibi durumlarda, diğer aktiflerle kombinasyon içinde kullanımı tavsiye edilir. Bronopol endüstride aşağıda belirtilen uygulamalara sahiptir:

Kağıt endüstrisi biositleri: Proses suyu muamelesinde ve fabrika (öğütme) katkılarının korunmasında. Kalsiyum karbonat bazlı tipik kağıt fabrika (öğütme) katkısı koruyucusu olarak etkilidir.

Su ve sıvıyağ alanı biositleri:

Yağ geri kazanımının yükseltilmesi ve soğutma kuleleri gibi endüstriyel suların şartlandırılması.

Bronopol, (delici çamurlarda) mikrobiyal kirlenmeyi kontrol etmek için kabiliyetlidir. Yapılan testlerde bütün düzeylerdeki kontaminasyonu temizleyebildiğini gösterir.

Endüstriyel ürün muhafazası:

Polimer emülsiyon yapıştırıcılar ve endüstriyel katkılar gibi teknik ürünlerin muhafazası. Bronopol, ev ürünlerinin farklı bir aralığında çok düşük düzeylerde uygulanmak üzere yeterli bir şekilde etkili olmasına rağmen, uzun süre koruma saplamak için de yeterli bir kararlılıktadır.

Bronopol veya 2-Bromo-2-nitro-1,3-propandiol, geniş spektrumlu antimikrobiyal özelliklere sahip inorganik bir bileşiktir. İlk olarak 1897'de sentezlenen bronopol, 1984 yılında ABD'de, endüstriyel bakterisit, inceltici ve koruyucu maddeler için koruyucu olarak kullanıldı [F13]. Bronopol, petrol sahası sistemleri, hava yıkama sistemleri, klima veya nemlendirme sistemleri, soğutma suyu sistemleri, papermiller, emici killer, tüketici ürünleri de dahil olmak üzere çeşitli ticari ve endüstriyel uygulamalar için bir mikrobisid veya mikrobiyostat olarak kullanılır [F13]. Diğer alifatik halojen-nitro bileşiklerine kıyasla, bronopol normal koşullarda sulu ortamda hidrolize daha stabildir [A32792]. _Pseudomonas aeruginosa dahil olmak üzere çeşitli bakterilere karşı inhibitör aktivite, in vitro olarak gösterilmiştir [A32792]. Bronopol, Kanada'daki antibakteriyel OTC ürünlerinde kullanılmak üzere onaylanmıştır.

2-BROMO-2-NITROPROPANE-1,3-DIOL beyaz kristallerdir. Kolayca tutuşturun ve kolayca yanık. Güçlü şok altında patlayabilir. Isındığında zehirli gazları açığa çıkarır. Cilt emilimi, inhalasyon veya yutulmasıyla toksiktir.

2005-06'da, alerjik kontakt dermatitten şüphelenilen kişilerin yama testlerinde (% 3.4) 15. en yaygın allerjen oldu. Solventlerde formaldehit, dezenfektan ve koruyucu yerine kullanılır. Cilt ve kişisel bakım ürünlerinde ve topikal ilaçlarda yaygındır.

Özellikler: Aktif madde Bronopol içeren biosidal ürünler, endüstriyel ve tüketici ürünlerinin muhafazası için ve endüstriyel ve proses suyunun şartlandırılmasında kullanılır. Bronopol, suda çözünürdür ve proteinler ve non iyoniklerle uyumludur. Mantarsal aktivitesi zayıftır, pH 8'in üzerinde zayıf stabilite gösterir, nitrozamin oluşumuyla ilişkilidir, algılanabilir formaldehit salar. Tipik kullanım konsantrasyonu % 0,01-0,04 arasındadır.

Çözünürlük ve karışabilirlik: Bronopol kolaylıkla sulu formülasyon sistemlerine dahil edilebilir. Konsantre sulu çözeltileri düşük sıcaklıkta kristallenmeye eğilim gösterirler. Bronopol polar olmayan çözücülerde zayıf bir şekilde çözünür, fakat organik polar solventlere yüksek ilgi gösterir.

Sulu olmayan sistemlerde, hammaddelerin dikkatli bir seçimiyle uygun taşıyıcı bir solvent kullanımıyla, Bronopol'ün etkili düzeyini elde etmek mümkündür.

Depolama kararlılığı: Ortam sıcaklığında, kapalı ambalajında depolandığında, Bronopol'ün kristal tipleri en az 3 yıl, sıvı formülasyonları en az 2 yıl stabildir. Kristal maddenin sulu çözeltileri hazırlandığında, bronopol en çok sistemin pH'ı asidik olduğunda kararlıdır. Tamponların varlığında, Bronopol'ün konsantre çözeltileri kendi kendini kararlı yapmaya eğilim gösterir. Stabilite için en iyi pH, 4 civarındadır ve Bronopol'ün seyreltik çözeltilerindeki çalışmalardan elde edilen veriler, pH=4'de ve oda sıcaklığında ömrünün 5 yıldan fazla olduğunu ortaya koyar. pH ve sıcaklık artışlarında sulu bronopol çözeltileri daha az kararlı olurlar.

Uyumluluk: Bronopol çözeltilerinin (%20) konsantre sulu çözeltilerinin paslanmaz çelikte (321 tipi), katı PVC, Polietilen (XDG33), plastikleşmiş PVC, silikon kauçuk, nylon ve polipropilenle uyumlu olduğunu gösterir. Seyreltilmiş sulu bir bronopol çözeltisi (% 0,02)(kullanım düzeyinin temsilcisi); paslanmaz çelik (321), alüminyum, prinç, bakır, katı PVC, polietilen (WJ611) ve polietilen (XD633) ile uyumlu olduğu görülür.

Antimikrobiyal aktivite: Bronopol, antimikrobiyal hareketin kompleks bir tarzına sahiptir. Bakteri azaltan anaerobik sülfat içeren Bronopol bakterilerin bütün gruplarına karşı geniş bir spektruma sahiptir. Bakterilerin çoğunluğu 6,25 ve 50 ppm arasında durdurulur.

Bronopol'ün mantarlara karşı aktivitesi daha değişiktir ve genel olarak çoğalmayı durdurmak için daha yüksek dozlar gerekir. Maya ve küflerin çoğunun durdurulmasında 400-1600 ppm aralığına ihtiyaç duyulur. Bununla birlikte bozucu mantar 6400 ppm'in aşırısını ister ve bu yüzden her zaman tek başına Bronopol'le ekonomik dozaj oranları kontrol edilemez. Bu gibi durumlarda, diğer aktiflerle kombinasyon içinde kullanımı tavsiye edilir. Bronopol endüstride aşağıda belirtilen uygulamalara sahiptir:

Kağıt endüstrisi biositleri: Proses suyu muamelesinde ve fabrika (öğütme) katkılarının korunmasında. Kalsiyum karbonat bazlı tipik kağıt fabrika (öğütme) katkısı koruyucusu olarak etkilidir.

Su ve sıvıyağ alanı biositleri:

Yağ geri kazanımının yükseltilmesi ve soğutma kuleleri gibi endüstriyel suların şartlandırılması.

Bronopol, (delici çamurlarda) mikrobiyal kirlenmeyi kontrol etmek için kabiliyetlidir. Yapılan testlerde bütün düzeylerdeki kontaminasyonu temizleyebildiğini gösterir.

Endüstriyel ürün muhafazası:

Polimer emülsiyon yapıştırıcılar ve endüstriyel katkılar gibi teknik ürünlerin muhafazası. Bronopol, ev ürünlerinin farklı bir aralığında çok düşük düzeylerde uygulanmak üzere yeterli bir şekilde etkili olmasına rağmen, uzun süre koruma saplamak için de yeterli bir kararlılıktadır.