Process for laundering paint soiled garments

A process for laundering garments soiled with a one component paint, a two component paint, a waterborne paint, a powder coat paint or a mixture thereof comprising the steps of exposing the soiled garment to an acid ester; subsequently washing the garment by exposing the garment to at least one detergent and to at least one alkali to remove paint solids adhered to the garment in the presence of a coating solvent to prevent the redeposition of the paint solids removed from the garment by the detergent and the alkali and, subsequently drying the garment.

FIELD OF THE INVENTION 
This invention relates to a process for laundering garments which are 
soiled by paint, such as overalls worn by workers in automobile paint 
facilities. 
BACKGROUND TO THE INVENTION 
In various manufacturing operations, workers are supplied with garments 
such as overalls or other forms of overclothes. These garments become 
soiled during the course of work. Typically, these garments require 
laundering after each wearing. Exemplary of this is car manufacturing 
plants. The exterior paint layer of a car forms an integral part of the 
car's anticorrosion systems. To ensure the proper formation of the 
exterior paint layer, cars are typically painted in strictly controlled 
environments. Since small particulates can compromise the integrity of the 
paint, workers in the paint facilities wear overclothes which are supplied 
by the manufacturer to prevent, or limit, the contamination of the 
environment. Typically, these garments become soiled with paint and, by 
the end of each shift, the garments require laundering. 
Various processes have been developed to launder such garments. For 
example, paint soiled garments may be collected and sent to a commercial 
laundry where they may be washed in a detergent containing bleach or an 
alkali solution. These garments are then returned to the paint spray 
facility. One difficulty with such processes is that they do not 
thoroughly clean the garments. The washed garments will generally still 
contain residual paint. Such residue reduces the useful life of the 
garment. Over a course of several washings, this residual paint will 
continue to build up. Typically, such garments are used and washed only 
about 30 times before they are discarded. 
SUMMARY OF THE INVENTION 
In accordance with the invention, there is provided a process for 
laundering garments soiled with a one component paint, a waterborne paint, 
a powder coat paint or a mixture thereof comprising the steps of: 
(a) exposing the soiled garment to an acid ester; 
(b) subsequently washing the garment by exposing the garment to at least 
one detergent and to at least one alkali to remove paint solids adhered to 
the garment in the presence of a coating solvent to prevent the 
redeposition of the paint solids removed from the garment by the detergent 
and the alkali; and, 
(c) subsequently drying the garment. 
The ester is preferably a basic acid ester, more preferably a di-basic acid 
ester and, most preferably, an aliphatic di-basic acid ester. The 
detergent is preferably a nonionic detergent. The solvent is preferably an 
aromatic solvent, more preferably a light aromatic solvent, and most 
preferably solvent naphtha. After the drying step, the garment preferably 
contains a paint repelling amount of said solvent. 
The garment is preferably exposed to the ester prior to the paint curing on 
the garment. 
The garment is preferably treated to contain a paint repelling amount of an 
aromatic solvent prior to the garment being first soiled with paint. 
In an alternate embodiment, there is provided a process for laundering 
garments soiled with a one component paint, a two component paint, a 
waterborne paint, a powder coat paint or a mixture thereof comprising the 
steps of: 
(a) exposing the soiled garment to an acid ester prior to the paint curing 
on the garment; 
(b) subsequently washing the garment by exposing the garment to at least 
one detergent and to at least one alkali to remove paint solids adhered to 
the garment in the presence of a coating solvent to prevent the 
redeposition of the paint solids removed from the garment by the detergent 
and the alkali; and, 
(c) subsequently drying the garment. 
DESCRIPTION OF THE PREFERRED EMBODIMENT 
The process is for use in laundering garments which are soiled with paints. 
Various different paints are employed in industry. For example, in the 
automotive field, several different paints are utilized including one 
component paints, two component paints, waterborne paints and powder coat 
paints. One component paints typically have a high level of solids and 
generally dry (or cure) in about 48 hours at room temperature. Two 
component paints typically comprise a first component which includes the 
paint solids and a second component which may generally be described as a 
fixer. The fixer acts as a catalyst so as to increase the rate of drying. 
Two component paints generally dry in about 18 to 24 hours at room 
temperature. Waterborne paints have lower solid levels and generally dry 
in about 24 hours at room temperature. Similarly, powder coat paints will 
also cure in about 24 hours at room temperature. Preferably, this process 
is used on garments which are soiled with a one component paint, a two 
component paint, a waterborne paint, a powder coat paint or mixtures 
thereof. 
The garments which are soiled with the paint may be made from a variety of 
materials. For example, the garment may be made from a woven synthetic 
fabric (such as nylon or polyester) or a woven natural fibre (such as 
cotton or rayon). The garment may also be made from a non-woven fabric 
such as TYVEK.TM. (a spunbonded olefin). Some laminates may also be 
utilized. Some of the chemicals utilized in this process may have a 
deleterious effect on laminates. In particular, the chemicals may attack 
the adhesive which is used to bond the laminate layers together such that 
the individual layers of the laminate may separate from each other during 
the laundering process. The adhesive utilized in some laminates, such as 
TETRATEX.TM. are not attacked by the chemicals used in the instant 
application and may be laundered by this process. There are numerous 
laminates which are available for use by industry. A person skilled in the 
art will be able to determine which laminates may be utilized according to 
this process. 
The soiled garments are preferably laundered prior to the paint fully 
drying (curing). If the garments can not be laundered while the paint is 
still tacky and the paint is a one component paint, a waterborne paint, a 
powder coat paint or a mixture thereof, then while the laundering process 
may remove a substantial amount (for example about 60%), the process will 
not necessarily remove all of the paint soil. If the paint is a two 
component paint in which the catalyst has fully cured, then the process 
will not remove the cured paint. 
If the laundry facility is located near the plant where the garments are 
soiled, then the garments may be immediately shipped, for example after 
the shift during which they are soiled, to the laundry facility for 
cleaning. In other cases, the laundry facility may be located at some 
distance from the plant or the laundry facility may not be able to clean 
the garments shortly after they are soiled (e.g. the laundry facility is 
closed for the weekend or holidays). 
If the garments can not be laundered while the paint is still tacky, then 
the garments are preferably treated so as to delay the curing of the 
paint. In such cases, the garments may be sealed in a package (e.g. 1 mil 
polyethylene) and then shipped to the laundry facility. Garments which are 
stained with a one component paint, a waterborne paint or a powder coat 
paint are preferably stored at a temperature below about 100.degree. F. 
and at a moisture content above about 35%. Paints soiled with a two 
component paint are preferably stored at a temperature less than about 
50.degree. F. (more preferably less than about 40.degree. F.) and at a 
moisture level above about 40% and more preferably above about 45% 
moisture. 
Once the used garments are placed in a package, excess air is preferably 
removed from the package and the packages are then sealed and stored under 
the conditions set out above. Garments treated in this manner may be 
stored, once packaged, for up to 48 hours, more preferably up to about 24 
hours, and most preferably up to about 12 hours prior to laundering. It 
should be noted, that by the time the garments are packaged, some of the 
paint on the garments may be up to about 8 hours old. 
At the laundry facility, the garments are pretreated with an ester. The 
garment is then washed, rinsed and dried. The dried garment may then be 
shipped back to the paint facility. 
As stated above, the soiled garments are first pretreated by exposing the 
garment to an acid ester. Preferably, the ester is a basic acid ester, 
more preferably, the ester is a di-basic acid ester and most preferably, 
the di-basic acid ester is an aliphatic di-basic acid ester. The ester may 
be of the general formula: 
EQU R.sup.1 OOR.sup.2 OOR.sup.3 
wherein R.sup.1 and R.sup.3 are the same or different and are selected from 
the group consisting of hydrogen and a lower alkyl group having 1 to 10 
carbons; and, 
wherein R.sup.2 is a lower alkyl group having 1 to 10 carbons. 
Examples of such di-basic acid esters include dimethyl glutarate, dimethyl 
succinate and dimethyl adipate. 
If the garment is only lightly soiled, (for example only a few locations on 
the garment are soiled with paint), then a solution containing the ester 
may be sprayed on to the spots which require treatment. Alternately, if 
the garment is heavily soiled, then the entire garment may be soaked in a 
solution containing the ester. Preferably, the solution contains from 
about 20 to about 100 wt. % ester, more preferably from about 45 to about 
100 wt. %, and most preferably, from about 85 to about 100 wt. %. The 
ester acts to stop the paint from setting. Without being limited by 
theory, it is believed that the ester acts to stop the curing 
(polymerization) process. In addition, the ester commences to break up the 
chemical bonds in the paint. This prepares the paint for the washing 
process during which the paint is removed from the garment. 
The ester may be applied at various temperatures to the soiled garment. Due 
to the volatility of the ester, it is preferred to apply the ester at a 
temperature from about 60.degree. to about 150.degree. F. More preferably, 
the ester is applied at room temperature (about 60.degree. to about 
72.degree. F.). 
Once the garment has been treated by exposure to the ester, the garment 
proceeds to the washing step. The washing step assists in breaking up 
additional paint solids which remain on the fabric and taking the paint 
solids into solution. The garment is preferably washed shortly (e.g. 1 
hour) after the pretreatment step before the ester volatilizes. At this 
time, the fabric is washed in the presence of at least one detergent and 
at least one alkali compound. The detergent may be any of those known in 
the art for paint solids. The detergent isolates the solid paint particles 
and takes these into solution so that the paint solids may be removed. The 
detergent may be an anionic or a nonionic detergent. Preferably, the 
detergent is selected from the group consisting of ethoxylates and 
phosphates. 
Generally, in order for detergents to take the solid paint particles into 
solution, a complimentary solvent must be provided for the detergent. 
Preferably, the solvent is an organic solvent. More preferably, the 
solvent is an aromatic solvent. Most preferably, the solvent is a light 
aromatic solvent such as solvent naphtha. 
The alkali may be any of those which is known in the art. The alkali acts 
to break up the molecular structure of the paint so that it may be 
solubilized by a detergent. The alkali may be an hydroxide (e.g. sodium 
hydroxide) or a silicate (e.g. sodium orthosilicate). 
The detergent and alkali may be mixed together in any order with the 
garment and applied to the garment in any manner known in the laundering 
art. In order to thoroughly expose all portions of the garment to the 
detergent and the alkali, the garments are preferably immersed in water 
into which the detergent and the alkali are subsequently added. It will be 
appreciated that, in order to assist the mixing of the chemicals with the 
garments, the garments may be agitated during the washing process. 
Accordingly, the garments may be added to a suitable washing machine to 
which water is added. The detergent and alkali are then added to the 
garments as described above. 
The concentration of alkali in the wash water is preferably from about 0.5 
to about 1.5 g/l, more preferably from about 0.9 to about 1.5 g/l and, 
most preferably from about 1 to about 1.5 g/l. The concentration of the 
detergent may range from about 1 to about 3 g/l, more preferably from 
about 1.5 to about 3 g/l and, most preferably from about 2 to about 3 g/l. 
The solvent for the detergent is present in a sufficient amount to 
solubilize the paint solids. The concentration of the solvent may range 
from about 0.5 to about 2 vol %, more preferably from about 1 to about 2 
vol % and, most preferably from about 1.5 to about 2 vol %. 
The alkali and detergent may be repeatedly applied to the garment so that 
the garment is washed a plurality of times. The number of washes to which 
the garment is subjected will vary depending upon the degree of the curing 
of the paint, the degree of soiling of the paint and the type of paint. 
Preferably, the garment is washed with the alkali and the detergent at 
least twice and, more preferably, three times during the wash cycle. 
In order to increase the effectiveness of the detergent, the washing step 
may occur at an elevated temperature (e.g. above about 90.degree. F. but 
sufficiently low so as not to damage the fabric). Preferably, the washing 
step may occur at a temperature from about 90.degree. to about 160.degree. 
F., more preferably from about 130 to about 160.degree. F. and, most 
preferably about 145.degree. F. The higher temperature ranges are 
preferably utilized as the higher temperatures aid the solubility of the 
detergent and alkali. However, the use of higher temperatures in the 
presence of higher alkali concentrations is deleterious to some fabrics, 
such as polyester, and accordingly lower temperatures are preferably used 
for these fabrics. In addition, if the garments are soiled with a two 
component paint, it is preferred that at least the initial washing steps, 
if not all washing steps occur at the lower end of the range (about 
90.degree. to about 145.degree. F.). If at least one of the washing steps 
occurs at the higher end of the temperature range, then the temperature of 
the garments is preferably gradually reduced so as to avoid temperature 
shock to which some fabrics such as polyester are prone. 
Subsequent to the washing step, the garments are rinsed with water to 
remove all, or substantially all, of the residual chemicals. To this end, 
the garments may be repeatedly exposed to water. For example, the garments 
may be run through a plurality of rinse cycles in a washing machine 
whereby in each rinse cycle the garments are soaked in water and the water 
is then removed by draining the water and subjecting the garments to 
centrifugal action (such as in a spin dryer of a washing machine) at high 
r.p.m. 
After the rinse step, the garments are dried. The garments may be dried by 
a combination of centrifugal action (such as by a spin dry cycle of a 
washing machine) and by exposing the garments to an elevated temperature 
below the degradation temperature of the fabric (such as in a dryer). The 
temperature at which the clothes are dried is based upon the fabric which 
is utilized. For example, if the garments comprise polyester, then the 
clothes are preferably dried at a temperature up to about 145.degree. F. 
Above this temperature, the polyester fibre will degrade. 
The garments are preferably exposed to an aromatic solvent such that at 
least a portion of the aromatic solvent remains in the garment when the 
garment is next worn. It has surprisingly been found that leaving residual 
amounts of an aromatic solvent on the garment increases the soil 
repellency of the fabric. Without being limited by theory, it is believed 
that the presence of small amounts of an aromatic solvent in the 
interstices of the fabric itself acts as an anti-redeposition agent which 
aids in reducing the adhesion between the paint and the fabric of the 
garment. Preferably, the residual amount of aromatic solvent in the dried 
garment is from about 0.1 to about 1 vol %, more preferably from about 0.3 
to about 1 vol % and, most preferably from about 0.5 to about 1 vol %. If 
greater than about 1 vol % is used, then the solvent may cause skin 
irritation for the individual who wears the garment. 
The aromatic solvent may be added during the washing process and, 
preferably, the organic solvent is the same as that which is added with 
the detergent in the washing step. Accordingly, the garments are 
preferably not completely dried. Preferably, the garments are dried so as 
to contain from about 1 to about 5 wt. % moisture, more preferably from 
about 3 to about 5 wt. % and, most preferably, about 5% moisture. 
Depending upon the chemicals which are utilized, the pH of the garments 
subsequent to the rinse step may vary broadly, e.g. from about 4 to about 
12. Preferably, the pH of the garments is adjusted so as to increase the 
longevity of the garments and decrease, or eliminate, any skin irritation 
which may be caused to the worker. Preferably, the pH is neutralized to a 
skin normal pH (e.g. from about 5.5 to about 6.5). If the pH of the 
garment after the rinsing cycle is acidic, then the pH is neutralized by 
the addition of a basic compound such as sodium hydroxide. Alternately, if 
the pH of the garments after the washing cycle are basic, then the 
garments may be neutralized by an acidic compound such as hydrofluosilicic 
acid or phosphoric acid. 
After the drying step, the garments are ready to be used. If the garments 
are to be used shortly after the washing step, then the garments may be 
sent to the plant where they are to be used. However, over time, the 
aromatic solvent which is preferably applied to the garments will 
evaporate from the clothing reducing the degree of soil repellency of the 
garment. The rate of deterioration of the soil repellency will vary 
depending upon the volatility of the aromatic solvent which is used and 
the temperature at which the garments are stored. Generally, the garments 
may be stored for up to about one week if a light aromatic solvent is 
utilized before the soil repellency deteriorates to an undesirable level. 
If the garments are not to be used immediately, the garments are 
preferably sealed (such as by packaging them in 1 mil polyethylene bags 
from which the excess air has been removed). 
In an alternate embodiment, the garments are preferably treated by exposing 
them to an aromatic solvent before they are first soiled. As discussed 
above with respect to the washing step, the aromatic solvent adds a degree 
of soil repellency to the fabric thereby reducing the adherence of paint 
to the garment. The aromatic solvent is preferably a light aromatic 
solvent such as solvent naphtha. The garment is exposed to the aromatic 
solvent so that a portion of the aromatic solvent is retained in the 
interstices of the fabric. Preferably, the fabric contains from about 0.1 
to about 1 vol %, more preferably from about 0.3 to about 1 vol % and, 
most preferably from about 0.5 to about 1 vol % of the aromatic solvent. 
The aromatic solvent may be applied to the fabric by subjecting the 
garment to a preliminary washing step in which an aromatic solvent is 
added to the garment while in a washing machine, preferably with 
agitation. 
As discussed above, the aromatic solvent is volatile. Accordingly, 
depending upon the amount of time before the garment is soiled, it is 
preferred to seal the garment in, e.g. a 1 mil polyethylene bag, so as to 
retain the aromatic solvent in the fabric. 
In many cases, paint facilities are operated as cleanrooms so as to reduce 
the contaminants which are included in the coat of paint which is applied. 
In particular, paint facilities have varying cleanroom standards which 
must be met by any article, including garments, which are brought into the 
paint facility. For example, automobile companies typically require that 
garments utilized in a paint facility have less than about 1% of particles 
less than 10.mu. in size removed therefrom. Accordingly, if the garments 
laundered according to this invention are to be used in the cleanroom, 
then the garments are preferably washed in a cleanroom environment and 
sealed subsequent to the washing/drying operation. In addition, in order 
to control the contamination of the garments, the garments, subsequent to 
soiling, are preferably packaged in a sealed container. 
New garments typically also contain various soils from the manufacturing 
process as well as loose fibre and threads. In such a case, the 
preliminary washing step for new garments which are to be utilized in a 
cleanroom environment preferably also includes subjecting the garments to 
the washing/drying steps described above. These steps aid in removing 
soils from the manufacturing process and residual fibres from the garments 
so that the garments meet the requisite cleanroom standard. These and 
other advantages of the instant invention will be more fully and 
particularly understood in connection with the following description of 
the Examples.

EXAMPLE 1-COMATIVE EXAMPLE 
Forty coveralls, each of which was manufactured from 100% polyester, were 
soiled with a PPG Canada Inc. one component high-solids automotive paint. 
To this end, the coveralls were worn by workers at a paint spray facility 
using this paint for a standard eight hour shift. After the shift, the 
coveralls (about 20% of each of which were covered with paint) were 
removed by the workers and immediately shipped for laundering. The 
laundering of the garments commenced within about 3 hours of the end of 
the shift. 
The garments were placed in a Wascomat FL184.TM. commercial washing machine 
having liquid chemical feed by micro processor controlled peristaltic 
pumps. The coveralls were subjected to three washing cycles. In the first 
cycle, fourteen gallons of water at 86.degree. F., 16 oz. of solution A 
and 4 oz. of solid mixture B were added to the washing machine. 
Solution A: 
solvent naphtha--60 wt. % 
nonylphenol ethoxolate--40 wt. % 
Solid Mixture B: 
sodium tripolyphosphate--16.5 wt. % 
NaOH--10 wt. % 
CaCl.sub.2 --3.5 wt. % 
soda ash--21 wt. % 
sodium orthosilicate--36.5 wt % 
nonylphenol--12.5 wt. % 
The coveralls were agitated in this mixture for 10 minutes and the wash 
water was then drained from the washing machine. In the second cycle, 14 
gallons of water at 160.degree. F. with 8 oz. of solution A and 4 oz. of 
solid mixture B were added to the washing machine. The coveralls were 
washed in the washing machine with agitation for 5 minutes at the end of 
which time the water was drained. In the third cycle, 14 gallons of water 
at 160.degree. F. and 8 oz. of the solid mixture B were added to the 
washing machine. The coveralls were washed in the washing machine with 
agitation for 5 minutes at the end of which time the water was drained 
from the washing machine. 
The coveralls were then rinsed in four cycles. In the first cycle, 16 
gallons of water at 160.degree. F. were added to the washing machine. The 
coveralls were agitated in the washing machine for 2 minutes at the end of 
which time the water was drained from the washing machine. This cycle was 
repeated three times. Each additional rinse cycle used water at 
140.degree. F., 120.degree. F. and 100.degree. F. respectively. 
The coveralls were then subjected to a pH adjusting rinse. According to 
this step, 14 gallons of water at 86.degree. F. and 2 oz of a solution 
comprising 20 wt. % of hydrofluosilicic acid were added to the washing 
machine. The coveralls were agitated in this mixture for 2 minutes at the 
end of which time the rinse water was drained from the washing machine. 
The coveralls had a pH from about 5.5 to about 6.5. 
The coveralls were dried by placing them in a steam injected Heubsch 
commercial drier for 22 minutes. At the end of this time, the coveralls, 
which had a moisture content of about 10% (as was determined by a 
hygrometer) were removed from the drier and examined. Only about 80% of 
the hard paint which had been present the coveralls when they were 
received from the paint facility had been removed. In addition, red and 
black pigments, which were present in the paint, were still visible on 
about 15% of each coverall (i.e. only about 50% removal). The hard paint 
which was left on the garment would limit the number of times which the 
garments could be worn. In addition, the hard paint could flake off during 
use and contaminate a car which is being painted. Accordingly, these 
garments could be worn for only about 75 times before they would have to 
be discarded. 
EXAMPLE 2 
The same experiment was repeated with the following variations. Ten 100% 
polyester overalls were utilized in the same paint facility for an 8 hour 
shift. When the coveralls were returned for laundering, the coveralls were 
first placed in a polyethylene wash basin and immersed in a solution of 
di-basic esters (66 wt. % dimethyl glutarate, 17 wt. % dimethyl adipate 
and 16.5 wt. % dimethyl succinate) for 24 hours. The coveralls were then 
subjected to the same washing and drying steps as set out above. 
Virtually all (about 99%) of the hard paint was removed from the 10 
coveralls. In addition, most of the pigment (about 75%) was also removed 
from the 10 coveralls. In particular, the red and black pigments which 
were present in the paint were only slightly visible in the coveralls. 
Accordingly, this garment could be worn, on average, about 200-300 times. 
EXAMPLE 3 
Two 100% polyester coveralls which had not been previously soiled by paint 
were washed according to the process set out in Example 1. The coveralls, 
once dried, were each placed in a one mil. plastic bags. The excess air 
was evacuated from the bags and the bags were sealed. 
The sealed bags were taken to the same automotive paint facility referred 
to in Example 1. In order to heavily soil the coveralls, the coveralls 
were pressed against a paint soiled paint booth wall. Above about 50% of 
each garment was covered with the one component paint. The garments were 
returned for laundering. 
The coveralls were placed in a stainless steel soaking tank and immersed in 
one gallon of the di-basic esther solution referred to in Example 2 for 10 
minutes with agitation. The coveralls were then removed from the di-basic 
esther solution and washed according to the process of Example 1. 
Despite the fact that the garments had been heavily soiled with paint, 
virtually all (about 95%) of the hard paint and pigment were removed from 
the two coveralls. 
EXAMPLE 4 
One clean overall of 100% polyester, which had not previously been soiled 
with paint, was washed according to the process set out in claim 1, dried 
and sealed in a one mil. plastic bag from the which the excess air had 
been removed. The clean garment was taken to an automotive paint spray 
facility which applies a two stage (i.e. a coloured base coat as well as 
clear top coat) two component low-solids automotive paint. The paint was 
manufactured by the Red Spot Paint and Varnish Co. The coverall was worn 
by a paint booth operator for an eight hour shift. The soiled garment was 
then placed in a one mil. plastic bag and placed in a cold polyethylene 
container (at a temperature of about 40.degree. F.) and transported back 
for laundering. 
The soiled coverall was placed in a stainless steel soaking tank in one 
gallon of the di-basic acid esther solution of Example 2 for 24 hours. At 
the end of the 24 hours, the coverall was placed in the same washing 
machine referred to in Example 1 and rinsed for 2 minutes in 16 gallons of 
water at 86.degree. F. 
The coverall was then subjected to three wash cycles. In the first wash 
cycle, 14 gallons of water at 86.degree. F. were added to the washing 
machine with 16 oz. of solution A and 4 oz. solid mixture B. The coverall 
was washed for 12 minutes with agitation at the end of which time the 
water was drained from the washing machine. The second washing cycle 
utilized 14 gallons of water at 86.degree. F., 8 oz. of solution A and 4 
oz of solid mixture B. The coverall was washed with agitation for 6 
minutes at the end of which time the water was drained from the washing 
machine. The third washing cycle utilized 14 gallons of water at 
140.degree. F. with 8 oz. of solid mixture B. The coverall was washed for 
10 minutes with agitation at the end of which time the water was drained 
from the washing machine. 
The coverall was then subjected to two rinse cycles, each of which used 16 
gallons of water and agitation for 2 minutes. The rinse water for the 
first cycle was at 125.degree. F. and the water temperature for the second 
rinse cycle 105.degree. F. 
The coverall was then subjected to the same pH adjusting rinse as was used 
in Example 1 and dried according to the same process as used in Example 1. 
Approximately 33% of the coverall had been covered with paint. As a result 
of the laundering operation, most (about 90%) of the hard paint which was 
on the garment was removed. In addition, (about 90%) of the pigment was 
also removed from the coverall. 
EXAMPLE 5 
Three clean coveralls made of 100% polyester, which had not been previously 
soiled with paint, were prewashed according to the process of Example 1, 
dried and individual sealed in one mil. plastic bags from which the excess 
air had been evacuated. The sealed garments were then taken to an 
automotive paint facility where they were heavily soiled with BASF.TM. 
waterborne automotive paint (approximately 50% coverage) by removing the 
garments from the plastic bags and pressing the garments against the wall 
of the paint booth. The soiled garments were then each placed in a one 
mil. plastic bag, placed in a polyethylene container at about 45.degree. 
F. and transported back for laundering. 
The soiled garments were removed from the plastic bag and immersed in two 
gallons of the di-basic esther solution of Example 2 for 24 hours. At the 
end of this period, the soaked coveralls were placed in the same washing 
machine which was used in Example 1 and rinsed for two minutes in 16 
gallons of water at 86.degree. F. The garments were then washed and dried 
according to the procedure of Example 1 except that the wash water for the 
second wash cycle was at 86.degree. F. 
As a result of the washing operation, virtually all of the hard paint and 
pigment (approximately 95%) were removed from the coveralls. 
EXAMPLE 6 
One clean coverall made of 100% polyester, which had not been previously 
soiled with paint, was prewashed according to the process of Example 1, 
dried and individual sealed in one mil. plastic bags from which the excess 
air had been evacuated. The sealed garment was then taken to an automotive 
paint facility where it was soiled with a PPG Canada Inc. powder coat 
automotive paint. In order to soil the coverall, the coverall was worn by 
a paint spray operator for a standard eight hour shift at the end of which 
time approximately 25% of the coverall was covered with paint. The soiled 
coverall was then placed in a one mil. plastic bag, placed in a 
polyethylene container at about 45.degree. F. and transported back for 
laundering. 
The soiled garment was removed from the plastic bag and immersed in two 
gallons of the di-basic esther solution of Example 2 for 24 hours. At the 
end of this period, the soaked coverall was placed in the same washing 
machine which was used in Example 1 and washed and dried according to the 
procedure of Example 1. 
Visual observation at the end of the drying cycle determined that all of 
the hard paint and pigment (approximately 99%), were removed from the 
coverall. Accordingly, with this level of removal, the garment could be 
cycled for at least about 200 wearings before it would have to be 
discarded.