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Preformed peracids are also known. They offer a weight efficiency advantage
since
no hydrogen peroxide is required and there is no “wasted” leaving group. The
main issue
with preformed peracids is stability—both of the raw material itself and in finished
product.
Phthalimidoperoxycaproic acid (PAP) is probably the best known. Metal bleach
catalysts
also offer great promise of weight efficiency. Bleach catalysts are transition metal
compounds,
typically Mn, Fe, Cu, or Co, with various chelating organic ligands. They react
with appropriate oxygen sources to form high valent metal oxides that are potent
oxidizing
agents. Most are designed for use with hydrogen peroxide, but the obvious goal is
to
develop a catalyst that works with molecular oxygen. To date there is no
successful
commercial example, but the search continues within many academic and
corporate labs.
In some regards photobleaches (normally metal phthalocyanines) could be
considered as
bleach catalysts. They generate singlet oxygen, a powerful bleaching species, on
exposure
to light and air. Because of the need for sunlight, and because the bleach is only
really
effective while the clothing is still wet, the utility of photobleach is greatest in
areas where
consumers air dry their laundry outside. Figure 4 presents the exemplary
structure of
common bleaches and chelants.
F. Chelating Agents
Chelants are often formulated in detergents because metal ions in the wash are
almost
always a detriment to end performance. Many highly colored stains incorporate
metals.
Removal of the metal can often decolorize the stain and/or make it easier to
remove by
destabilizing its structure. Examples include porphyrins found in blood and
tannins in tea.
Metal ions can also catalytically decompose bleach in a formulation, leading to
significantly
reduced performance. Finally, metals often find their way onto fabric surfaces,
either
as insoluble salts as with calcium or magnesium fatty acids, or as metal oxides.
Both lead
to a multicycle dinginess and fabric feel issues.
What chelant is used depends largely on local environmental regulations.
Diethylene
triamine pentaacetic acid (DTPA) is commonly used in North America. It’s an
analog of
the more well-known ethylenediaminetetraacetate (EDTA), but has a better
environmental
profile. In Europe, however, DTPA is banned due to concerns with aquatic toxicity.
As a
result, European formulations rely more on phosphonate-based chelants such as
diethylene
triamine penta(methylene phosphonic) acid (DTPMP) or ethylene diamine
tetra(methylene
phosphonic) acid (DDTMP). In an interesting twist, these materials cannot be used
in
North America due to bans on phosphorous in laundry detergents.
In environmental terms, ethylene diamine disuccinic acid (EDDS) represents the
best achievement thus far. The molecule has two chiral centers and only the S,S-
isomer
is fully biodegradable. This makes it a more expensive chelant than the
phosphonate
chelants mentioned previously. It is used in some European granules today. HEDP,
1-
hydroxyethyidene-1,1-diphosphonic acid, is not truly a chelant in the sense of the
materials
mentioned above, but because it also helps control deposition of metals on fabrics
it
deserves mention in the same section. HEDP works more by inhibiting crystal
growth.