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ALKYLPHENOL ETHOXYLATE (APE)

APEO

Alkylphenols, including nonylphenol and octylphenol, are key breakdown products of alkylphenol ethoxylate (APE) surfactants, once common in household detergents and other cleaning products and also used in a number of industrial applications.
Alkylphenols and APEs have been detected in water, sediment, mussel, small fish, and cormorant egg samples from the Bay, sometimes at relatively high concentrations. 

Alkylphenols and some APEs are known endocrine disruptors. 
While concentrations measured in the Bay have mostly been below those known to cause chronic toxicity in marine organisms, there is new evidence that the existing levels of alkylphenols and APEs, in combination with pyrethroid pesticides, may be aecting Bay fish populations through endocrine disruption. 
A recent RMP report on APEs presents additional information on use and production, fate in wastewater treatment plants and the environment, potential impacts, and information gaps.

Alkylphenols are a family of synthetic organic compounds consisting of chains of carbon atoms, typically branched and consisting of eight or nine carbon atoms, aached to a six-carbon phenol ring.
Alkylphenols are used to make APE surfactants, detergent-like compounds that have been widely used since the 1940s.

Eighty to eighty-ve percent of the APEs in use in the US are nonylphenol ethoxylates.
Octylphenol ethoxylates are the next most common APE.

Once released into the environment, APEs often break down into alkylphenols like nonylphenols and octylphenols.
The US Environmental Protection Agency (USEPA) has identified nonylphenol ethoxylates as priorities for voluntary phase-out.

Alkylphenols and their precursors, alkylphenol etoxylates, are a group of manmade chemicals used mainly as surfactants in domestic and industrial applications worldwide. 
It has been well established that they have endocrine disruption activity, hepatotoxic, genotoxic and other negative effects on animal and human health. 
In spite of the effort to reduce their use, they persist in the environment not only in industrial but also in remote regions, and were detected in the variety of natural matrices including air, water, soil as well as food products, and human blood and urine worldwide.

Alkylphenol ethoxylates are designed to improve stability performance of a wide range of polymer systems at the usage level of 0.5-3.0% (based on total monomers). 
The low ethoxylated Igepal products are also suitable for being used as the wetting agents. 
Alkylphenol ethoxylate are only suitable for solventborne system if their HLB value below 10.0. 

Provide a better stability for your waterborne coatings formulations.
The binders emulsified with these Igepal nonionics can be formulated into a broad range of applications, paints and coatings, adhesives, paper, textile, etc. 

They can be added during the polymerization as well as the post additives for improvement of mechanical, freeze thaw and chemical stability. 
When added during the polymerization, the stability of pre-monomer emulsion can be improved as well.

APEs are among the chemicals found at the highest concentrations in wastewater effluent and sediment.
APEs break down into chemicals such as nonylphenol and octylphenol, which are persistent, with half-lives estimated at up to 60 years in marine sediments. 

Nonylphenol can also bioaccumulate in some aquatic animals. 
These chemicals have been widely detected in surface water and sediment, and build up in fish and other wildlife. 
Large amounts are released to the environment just from their use in commercial laundry detergents—estimated at more than two million pounds released to wastewater treatment plants just in California.

Much of the concern about release of APEs into the environment is due to their toxic effects on fish and wildlife. 
Nonylphenol, for example, feminizes male fish and otherwise affects reproduction in fish and invertebrates.
Alkylphenol ethoxylate also affects growth and harms the immune system.

There are also concerns about the effects of APEs on human health, including reproductive, nervous system, and immune effects.

The state of California has begun to address APEs by proposing nonylphenol ethoxylates in laundry detergent as a priority product-chemical combination and opening the door for restriction. 
California should move forward with restrictions, and other states should follow suit. 
The Washington State Legislature is currently considering listing APEs as a priority chemical class and directing the Department of Ecology to consider restrictions on use.

Manufacturers, retailers, and users should ensure alkylphenol ethoxylates are not present in products they make, sell, or use. 
Some manufacturers and retailers have already taken this action.

Alkylphenols and their ethoxylates (APEs) are a family of chemicals used mainly as surfactants in commercial detergents and cleaners. 
They are also used in paints, pesticides and other agrochemicals, personal-care products, in industrial processes, and oilfields. 
Their breakdown products include persistent toxic chemicals that build up in fish and wildlife.

Why Alkylphenol Ethoxylates (APE) are Restricted:
Legislation around the world restricts the presence of APEO in finished products.
Leading apparel and footwear brands have restricted or banned the use of APEO in production of their products.

APEOs can degrade into alkylphenols in the environment.
Some APs are very toxic to aquatic life with long lasting effects.
Some APs are suspected of damaging human fertility and unborn children.

Applications of Alkylphenol Ethoxylate:
Alkylphenol ethoxylates are very effective and efficient. 

In most applications, these nonionics deliver significant performance improvement at a low usage level, such as:
Stability: mechanical, chemical, freeze thaw and pre-monomer emulsion
Wetting: pigment, substrates, etc
Color acceptance
Less water sensitivity versus the anionics
Less foaming tendency versus the anionics

Coatings:
Since the first use of waterborne coatings, additives have been incorporated to enhance the properties of the final coating. 
These additives include co-solvents, pigments, preservatives, defoamers, rheology modifiers and others. 

One of the most important is the wetting agent/dispersing aid. 
A wetting agent is a surface-active material that lowers the interfacial tension at phase boundaries.

Thus, the additive improves surface and pigment wetting. 
More often, the wetting agent is a non-ionic surfactant, and over the past 40 years the leading surfactants utilized for this purpose have been based on alkylphenol ethoxylates. 
For much of this time, these nonionic surfactants provided the optimum cost/performance properties desired by coatings formulators.

In 2006, sales of APEOs in the coatings market consisted of 22,700 metric tons octylphenol (OPEs) and 17,700 metric tons nonylphenol (NPEs) ethoxylates. 
These amounts were used both directly in coatings formulations and for emulsion polymerization.
These particular ethoxylates were preferred as wetting agents because they provided cost effectiveness while maintaining adaptable properties for many coating and non-coating applications. 

Alkylphenol ethoxylates in general possess a number of structural, compositional and performance attributes that have helped the surfactants to become the lead wetting aid in North America.

Uses of Alkylphenol Ethoxylate:
APE are primarily used as detergents in the textile wet processing industry but they are also used in the leather industry as degreasing products and in small quantities as emulsifiers or wetting agents in some dyestuff and pigment preparations. 

Uses in the Supply Chain:
APE are common ingredients in many chemical formulations used to produce apparel and footwear materials.
They have been widely used as surfactants or emulsifiers in detergents, scouring agents, dye-dispersing agents, printing pastes, spinning oils and wetting agents.

APEs are commonly used as surfactants in detergents and cleaning products for industrial and institutional seings. 
They are now less common in products for the home.

APEs have been added to pesticide formulations as “inert ingredients” to enhance performance.
They are also used in paper production, leather and textile processing, metalworking, as oilfield chemicals and for dispersal of petroleum spills, and as ingredients in paints, adhesives, personal care products, and spermicidal lubricants.

May Be Found In:
Industrial laundry detergent,
Scouring agents (e.g., wool and leather),
Wetting agents,
Softeners,
Spinning oils (yarn and fabric),
Emulsifier/dispersing agents for dyes and prints,
Impregnating agents,
Degreasing agents for leather hides,
Leather-finishing preparations,
De-gumming agents for silk production,
Dyes and pigment preparations,
Polyester padding,
Down/feather fillings,
Binders for interlinings,
Facility cleaning products.

General Properties of Alkylphenol Ethoxylate:
Alkylphenols and APEs entering the water column have a strong tendency to bind to sediment particles.

APEs can be broken down by microbes or sunlight into alkylphenols and other compounds in the Bay, depending on environmental conditions. 
The environmental fate of these breakdown products is not well understood.

Nonylphenol itself does not break down easily and is considered a persistent pollutant in aquatic environments.
Alkylphenols and APEs are somewhat volatile, so a portion of these chemicals may be removed from the Bay by transfer into the air.

Alkylphenols and APEs are known to accumulate inwildlife, especially invertebrates and sh. 
Most studies have focused on nonylphenol and octylphenol, as they are readily accumulated and stored in fat tissues and there is concern for toxicity, particularly endocrine disruption.

Exposure of Alkylphenol Ethoxylate:
APEs are among the chemicals found at the highest concentrations in U.S. house dust.
They are also found in air, drinking water, and food.
As a result, APEs have been detected in human urine, cord blood, and breast milk.

Consumers can avoid products that list nonylphenol or octylphenol ethoxylates as ingredients, and ask policymakers, manufacturers, and retailers to restrict or eliminate use of these chemicals.

Safer Alternatives of Alkylphenol Ethoxylate:
The following substances have been identified as examples of safer alternatives by the U.S. Environmental Protection Agency Design for the Environment Program (DfE).
They may be suitable for your production needs. 
Any chosen alternative must be compliant with the limits stated above as well as any brand specific limits.

CAS Number   -   Substance:
68439-46-3   -   C9-11 alcohols, ethoxylated (6EO)
68131-39-5   -   C12-15 alcohols, ethoxylated (9EO)
64366-70-7   -   Oxirane, methyl-, polymer with oxirane, mono(2 ethylhexyl ether); Ecosurf EH-9
68515-73-1   -   Glucopyranose, oligomeric, decyl octyl glycosides
68411-30-3   -   Benzenesulfonic acid, C10-13-alkyl derivs., sodium salt
151-21-3   -   Sodium lauryl sulfate
9004-82-4   -   Polyoxy(1,2-ethanediyl), alpha-sulfo-omegadodecyloxy-, sodium salt
1338-41-6   -   Sorbitan monostearate 

CAS Number - Substance:
9002-93-1 - Polyethylene glycol 4-(tert-octylphenyl) ether
9036-19-5 - Polyethylene glycol mono(octyl)phenyl ether
68987-90-6 - Poly (oxy-1,2-ethanediyl), alpha-(octylphenyl)-omega-hydroxy-, branched

Other Names of Alkylphenol Ethoxylate:
Nonylphenol Ethoxylates (NPEOs; NPEs):
Polyethylene glycol nonylphenyl ether
Octylphenol Ethoxylates (OPEOs; OPEs):
Polyethylene glycol octylphenyl ether
 

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