Use of mixture of aliphatic C.sub.10 branched olefins in augmenting or enhancing the aroma of perfumed alkaline metal hypochlorite solutions

Described are methods for augmenting or enhancing the aroma of perfumes and perfumed articles by adding thereto perfume aroma augmenting or enhancing quantities of C.sub.10 -branched olefin mixtures produced by dimerizing isoamylene, (2-methyl-2-butene) as well as perfume compositions, colognes and perfumed articles including solid or liquid anionic, cationic, nonionic or zwitterionic detergents, fabric softener compositions, hair preparations and deodorant compositions as well as bleaching compositions containing same.

BACKGROUND OF THE INVENTION 
The instant invention provides mixtures of C.sub.10 branched chain olefins 
which are used to augment or enhance the aroma of perfume compositions, 
colognes and perfumed articles. 
Chemical compounds which can provide a woody, piney and herbaceous aroma 
are desirable in the art of perfumery. Many of the natural materials which 
provide such fragrances and contribute such desired nuances to perfumery 
compositions are high in cost, unobtainable at times, vary in quality from 
one batch to another and/or are generally subject to the usual variations 
of natural products. 
There is, accordingly, a continuing effort to find synthetic materials 
which will replace, enhance or augment the fragrance notes provided by 
natural essential oils or compositions thereof. Unfortunately, many of the 
synthetic materials either have the desired nuances only to a relatively 
small degree, or they contribute undesirable or unwanted odor to the 
compositions. 
Aliphatic hydrocarbons are well known in the art of perfumery, e.g. 
myrcene, 2-methyl-6-methylene-2,7-octadiene, a constituent of lemon grass 
oil. Also found in lemon oil as well as in Bergamot oil, according to 
Gildemeister and Hoffmann, (Die Atherischen Ole, 3rd edition, Volume 1, 
page 301) is octylene, a long chain olefin containing eight carbon atoms. 
Arctander, "Perfume and Flavor Chemicals, (Aroma Chemicals)", 1969, Vol. I, 
at monograph 974, discloses the use of "di-isoprene" in perfumery. 
Arctander states that di-isoprene is a mixture of 
2,6-dimethyl-2,6-octadiene; 2,7-dimethyl-2,6-octadiene; and 
3,6-dimethyl-2,6-octadiene. Arctander states that this material has a 
sweet, diffusive, somewhat "gassy" odor and, overall, is of very "little 
interest to the perfumer." At monograph 1074, Arctander discloses 
"dipentene" having a use in perfumery and indicates that this "dipentene" 
is 1-methyl-4-iso-propenyl-1-cyclohexene and indicates that it is useful 
in perfumery as a "lift" in citrusy fragrances and in the reconstruction 
of many essential oils such as Bergamot, Lime and Lemon. 
Nothing in the prior art discloses the use of di-isoamylene having one of 
the generic structures: 
##STR1## 
where one of the dashed lines is a carbon-carbon double bond and the other 
of the dashed lines is a carbon-carbon single bond in each molecule for 
augmenting or enhancing the aroma of perfumes, colognes or perfumed 
articles. 
"Di-isoamylene" is indicated to be synthesized in the following references: 
i--Murphy & Lane, Ind. Eng. Chem., Prod. Res. Dev., Vol. 14, No. 3, 1975 p. 
167 (Title: Oligomerization of 2-Methyl-2-Butene in Sulfuric Acid and 
Sulfuric-Phosphoric Acid Mixtures). 
ii--Whitmore & Mosher, Vol. 68, J. Am. Chem. Soc., February, 1946, p. 281 
(Title: The Depolymerization of 3,4,5,5-Tetramethyl-2-hexene and 
3,5,5-Trimethyl-2-heptene in Relation to the Dimerization of Isoamylenes) 
iii--Whitmore & Stahly, Vol. 67, J. Am. Chem. Soc., December, 1945, p. 2158 
(Title: The Polymerization of Olefins. VIII The Depolymerization of 
Olefins in Relation to Intramolecular Rearrangements. II) 
iv--U.S. Pat. No. 3,627,700, issued on Dec. 14, 1971, (Zuech) 
v--U.S. Pat. No. 3,538,181, issued on Nov. 3, 1970, (Banks) 
vi--U.S. Pat. No. 3,461,184, issued on Aug. 12, 1969 (Hay, et al) 
vii--Gurwitsch, Chemische Berichte, 1912, Vol. 2, p. 796 (Production of 
Di-isoamylene From Isoamylene Using Mercury Acetate Catalyst) 
United Kingdom Pat. No. 796,130 published on June 4, 1958 discloses the 
synthesis of polyalkylindanes by means of, interalia, reacting 
alpha-methylstyrene with trimethylethene (2-methyl-butene-2) in the 
presence of an acid catalyst such as, sulfuric acid or boron trifluoride 
methyletherate. It is further indicated that such compounds are useful 
intermediates in the production of perfumery compounds. Apparently 
however, the more volatile di-isoamylenes produced as side-products in the 
reaction of 2-methyl-butene-2 with alpha-methylstyrene are discarded. 
Thus, nothing in the prior art discloses the use of any of the 
di-isoamylenes of our invention in augmenting or enhancing the aroma of 
perfume compositions, perfumed articles or colognes.

THE INVENTION 
It has now been determined that dimers of isoamylene produced according to 
the reaction: 
##STR2## 
wherein one of the dashed lines in each of the molecules is a 
carbon-carbon double bond and the other of the dashed lines in each of the 
molecules is a carbon-carbon single bond, are capable of imparting or 
augmenting or enhancing a variety of fragrances to consumable materials. 
Briefly our invention contemplates augmenting or enhancing fragrances of 
such consumable materials as perfumes, perfumed articles (e.g. solid or 
liquid anionic, cationic, nonionic or zwitterionic detergents, cosmetic 
powders, fabric softener compositions and dryer-added fabric softener 
articles) and colognes by adding thereto, a small, but effective amount of 
at least one of the compounds defined according to one of the generic 
structures: 
##STR3## 
wherein, in each of the molecules, one of the dashed lines is a 
carbon-carbon double bond and the other of the dashed lines is a 
carbon-carbon single bond. 
The di-isoamylene compounds of our invention augment or enhance woody, 
piney and herbaceous aroma characteristics of perfumes, perfumed articles 
and colognes, thereby causing one or more of said di-isoamylene compounds 
to be useful particularly in pine fragrances. 
The di-isoamylene derivatives of our invention having the structures: 
##STR4## 
wherein in each of the molecules, one of the dashed lines is a 
carbon-carbon double bond and the other of the dashed lines is a 
carbon-carbon single bond may be prepared by reacting 2-methyl-2-butene in 
the presence of an acidic catalyst which may be a Lewis acid such as, zinc 
chloride, aluminum chloride, aluminum bromide, diethyl aluminum chloride, 
diethyl aluminum bromide, ethyl di-aluminum chloride and ethyl di-aluminum 
bromide, boron trifluoride, boron trifluoride ethyrate, or any of the 
other catalysts enumerated in the following references: 
i--Murphy & Lane, Ind. Eng. Chem., Prod. Res. Dev., Vol. 14, No. 3, 1975 p. 
167 (Title: Oligomerization of 2-Methyl-2-Butene in Sulfuric and 
Sulfuric-Phosphoric Acid Mixtures). 
ii--Whitmore & Mosher, Vol. 68, J. Am. Chem. Soc., February, 1946, p. 281 
(Title: The Depolymerization of 3,4,5,5-Tetramethyl-2-hexene and 
3,5,5-Trimethyl-2-heptene in Relation to the Dimerization of Isoamylenes) 
iii--Whitmore & Stahly, Vol. 67, J. Am. Chem. Soc., December, 1945, p. 2158 
(Title: The Polymerization of Olefins. VIII The Depolymerization of 
Olefins in Relation to Intramolecular Rearrangements. II) 
iv--U.S. Pat. No. 3,627,700, issued on Dec. 14, 1971, (Zuech) 
v--U.S. Pat. No. 3,538,181, issued on Nov. 3, 1970, (Banks) 
vi--U.S. Pat. No. 3,461,184, issued on Aug. 12, 1969 (Hay, et al) 
vii--Gurwitsch, Chemische Berichte, 1912, Vol. 2, p. 796 (Production of 
Di-isoamylene From Isoamylene Using Mercury Acetate Catalyst) 
Depending upon the conditions of reaction, including temperature, pressure, 
mole ratio of 2-methyl-2-butene:catalyst concentration of 
2-methyl-2-butene in solvent, concentration of catalyst in solvent and 
time of reaction, the ratio and nature of isomers will vary in an as yet 
undetermined fashion. In any event, this invention contemplates all 
isomers of di-isoamylene defined according to the generic structures: 
##STR5## 
wherein in each of the molecules, the dashed line represents a 
carbon-carbon single bond or a carbon-carbon double bond taken alone or in 
admixture in all proportions, when used in augmenting or enhancing the 
aroma of perfume compositions, perfumed articles, and colognes. 
As olfactory agents, the di-isoamylene derivatives, taken alone or in 
admixture, of our invention can be formulated into, or used as components 
of a "perfume composition" or can be used as components of a "perfumed 
article", or the perfume composition may be added to perfumed articles. 
The term "perfume composition" is used herein to mean a mixture of organic 
compounds including, for example, alcohols, aldehydes, ketones, nitriles, 
ethers, lactones, natural essential oils, synthetic essential oils and 
hydrocarbons other than the di-isoamylene derivatives of our invention 
which are admixed so that the combined odors of the individual components 
produce a pleasant or desired fragrance. Such perfume compositions usually 
contain (a) the main note or the "bouquet" or foundation stone of the 
composition; (b) modifiers which round off and accompany the main note; 
(c) fixatives which include odorous substances which lend a particular 
note to the perfume throughout all stages of evaporation, and substances 
which retard evaporation; and (d) top notes which are usually low boiling, 
fresh-smelling materials. 
In perfume compositions, the individual component will contribute its 
particular olfactory characteristics, but the overall effect of the 
perfume composition will be the sum of the effects of each of the 
ingredients and in certain instances, a synergistic effect as a result of 
the addition of certain ingredients. Thus, the individual compounds of 
this invention, or mixtures thereof, can be used to alter the aroma 
characteristics of a perfume composition, for example, by highlighting or 
moderating the olfactory reaction contributed by another ingredient in the 
composition. 
The amount of the di-isoamylene derivatives of this invention which will be 
effective in perfume compositions depends on many factors, including the 
other ingredients, their amounts and the effects which are desired. It has 
been found that perfume compositions containing as little as 0.05% of the 
di-isoamylene derivatives of this invention, or even less, can be used to 
impart an interesting, herbaceous, piney and woody aroma to soaps, liquid 
or solid anionic, cationic, nonionic or zwitterionic, detergents, 
cosmetics, cosmetic powders, liquid and solid fabric softeners, 
dryer-added fabric softener articles (e.g. BOUNCE.RTM. a registered 
trademark of the Procter & Gamble Company of Cinncinati, Ohio), optical 
brightener compositions and other products. The amount employed can range 
up to 70% or even higher, and will depend on considerations of cost, 
nature of the end product, and the effect desired on the finished product 
and particular fragrance sought. Thus, for example, when fragrancing 
liquid bleach compositions containing alkalihypochloride such as, for 
example, sodium hypochloride, for example CLOROX.RTM., (registered 
trademark of CLOROX, Inc.). The amount employed can be as high as 100% of 
the fragrance involved in the liquid bleach. Indeed, a distinctive aspect 
of our invention is the use of one or more of the di-isoamylene 
derivatives in a stable liquid bleach composition. 
The di-isoamylene derivatives of this invention, taken alone or in 
admixture, can be used alone, or in a perfume composition as an olfactory 
component in detergents, soaps, space odorants and deodorants; perfumes; 
colognes, toilet waters; bath salts; hair preparations, such as lacquers, 
brillantines, pomades and shampoos; cosmetic preparations, such as creams, 
deodorants, hand lotions, sunscreens; powders, such as talcs, dusting 
powders, face powders and the like; liquid bleaches, such as sodium 
hypochloride--containing bleaches; floor waxes; automobile aromas and 
automobile polish compositions. When used as an olfactory component of a 
perfumed article, as little as 0.01% of one or more of the di-isoamylene 
derivatives, will suffice to impart an interesting, herbaceous, piney and 
woody aroma. Generally, no more than 0.5% is required to impart such 
aromas, however, in view of the rather low cost of the di-isoamylene 
derivatives of our invention, up to 100% of the perfume composition, can 
be one or more of the di-isoamylene derivatives. 
In addition, the perfume composition can contain a vehicle or carrier for 
the di-isoamylene derivatives, alone, or with other ingredients. The 
vehicle can be a liquid such as a non-toxic alcohol such as ethanol, a 
glycol such as propylene glycol, or the like. The carrier can be an 
absorbent solid, such as a gum or components for encapsulating the 
composition such as gelatin which can be used to form a capsule wall 
surrounding the perfume oil, as by means of coacervation. 
It will thus be apparent that the di-isoamylene derivatives of our 
invention can be utilized to alter, modify, augment or enhance sensory 
properties, particularly organoleptic properties such as fragrances of a 
wide variety of consumable materials. 
The following examples serve to illustrate our invention, and this 
invention is to be considered restricted thereto only as indicated in the 
appended claims. 
All parts and percentages given herein are by weight unless otherwise 
specified. 
EXAMPLE I 
Preparation of Di-isoamylene Derivatives 
##STR6## 
(wherein in each of the molecules indicated, one of the dashed lines is a 
carbon-carbon double bond and the other of the dashed lines are 
carbon-carbon single bonds). 
Di-isoamylene is prepared according to one of the procedures set forth in 
the following references: 
i--Murphy & Lane, Ind. Eng. Chem., Prod. Res. Dev., Vol. 14, No. 3, 1975 p. 
167 (Title: Oligomerization of 2-Methyl-2-Butene in Sulfuric and 
Sulfuric-Phosphoric Acid Mixtures). 
ii--Whitmore & Mosher, Vol. 68, J. Am. Chem. Soc., February, 1946, p. 281 
(Title: The Depolymerization of 3,4,5,5-Tetramethyl-2-hexene and 
3,5,5-Trimethyl-2-heptene in Relation to the Dimerization of Isoamylenes) 
iii--Whitmore & Stahyl, Vol. 67, J. Am. Chem. Soc., December, 1945, p. 2158 
(Title: The Polymerization of Olefins. VIII The Depolymerization of 
Olefins in Relation to Intramolecular Rearrangements. II) 
iv--U.S. Pat. No. 3,627,700, issued on Dec. 14, 1971, (Zuech) 
v--U.S. Pat. No. 3,538,181, issued on Nov. 3, 1970, (Banks) 
vi--U.S. Pat. No. 3,461,184, issued on Aug. 12, 1969 (Hay, et al) 
vii--Gurwitsch, Chemische Berichte, 1912, Vol. 2, p. 796 (Production of 
Di-isoamylene From Isoamylene Using Mercury Acetate Catalyst) 
As an illustration, and not by way of limitation, the following Example 
sets forth the preparation of di-isoamylenes useful in producing the 
fragrances of our invention: 
Over a period of ten hours, 2-methyl-2-butene is pumped through a 
5'.times.5/8 (0.625 inch) tube packed with 15.0 g of polystyrene sulfonic 
acid catalyst, at a temperature of 100.degree. C. and at a pressure of 400 
psig. 
The resulting material was distilled in a fractionation column in order to 
separate the di-isoamylene from the higher molecular weight polymers, 
which are formed during the reaction as by-products. 
FIG. 1A represents the GLC profile for the reaction product of Example I 
using a 70% sulfuric acid catalyst at 35.degree. C. 
FIG. 1B represents the GLC profile for the reaction product of Example I 
using an Amberlyst.RTM. 15 acetic ion exchange resin catalyst at a 
temperature of 150.degree. C. 
FIG. 1C represents the GLC profile for the reaction product of Example I, 
using an Amberlyst.RTM. 15 catalyst at 100.degree. C. 
FIG. 1D represents the GLC profile for the reaction product of Example I, 
using a sulfuric acid catalyst and an alpha-methylstyrene diluent at 
35.degree. C. according to the conditions of United Kingdom Patent 
Specification No. 796,130 (crude reaction product) 
FIG. 1E represents the GLC profile for the reaction product of Example I, 
using a sulfuric acid catalyst, at 35.degree. C. and an 
alpha-methylstyrene diluent according to the conditions of United Kingdom 
Patent Specification No. 796,130 (distilled reaction product). 
FIG. 2A represents the NMR spectrum for Peak 1 of the GLC profile of FIG. 
1E. 
FIG. 2B represents the infra-red spectrum for Peak 1 of the GLC profile of 
FIG. 1E. 
FIG. 3A represents the NMR spectrum for Peak 2 of the GLC profile of FIG. 
1E. 
FIG. 3B represents the infra-red spectrum for Peak 2 of the GLC profile of 
FIG. 1E. 
FIG. 4 represents the NMR spectrum for Peak 2 of the GLC profile of FIG. 
1B. 
EXAMPLE II 
The di-isoamylene produced according to Example I has a woody, piney, 
herbaceous note which may be utilized to a great extent in inexpensive 
functional products. The following pine fragrance demonstrates the use of 
this material in perfume compositions. In this case it is used as 47.9%. 
______________________________________ 
Di-isoamylene 479 
Isobornyl Acetate 100 
Camphor 10 
Terpineol 25 
Fir Balsam Absolute (50% in Diethyl 
Phthalate 20 
Coumarin 4 
Linalool 30 
Anethol 2 
Fenchyl Alcohol 10 
Lemon Terpenes Washed 50 
Borneol 35 
Galbanum Oil 5 
Turpentine Russian 150 
Pinus Pumilionus 50 
Eucalyptol 50 
2,2,6-trimethyl-1-cyclohexene- 
1-carboxaldehyde 5 
Maltol 1% in Diethyl Phthalate 
5 
______________________________________ 
The presence of the di-isoamylene supports the pine notes and produces a 
considerable savings in the cost of the formulation. 
EXAMPLE III 
Preparation of a Cosmetic Powder Composition 
A cosmetic powder is prepared by mixing in a ball mill, 100 g of talcum 
powder with 0.25 g of the perfume composition prepared according to 
Example II. It has an excellent, piney aroma with woody and herbaceous 
nuances. 
EXAMPLE IV 
PERFUMED LIQUID DETERGENT 
Concentrated liquid detergents (Lysine salt of n-dodecylbenzene sulfonic 
acid as more specifically described in U.S. Pat. No. 3,948,818, issued on 
Apr. 6, 1976) with herbaceous, woody and piney aroma nuances are prepared 
containing 0.10%, 0.15%, 0.20%, 0.25%, 0.30% and 0.35% of the fragrance 
prepared according to Example II. They are prepared by adding and 
homogeneously mixing the appropriate quantity of fragrance formulation 
prepared according to Example II in the liquid detergent. The detergents 
all possess excellent piney aromas with woody and herbaceous undertones, 
the intensity increasing with greater concentrations of perfume 
composition of Example II. 
EXAMPLE V 
PREATION OF A COLOGNE AND HANDKERCHIEF PERFUME 
The composition prepared according to Example II is incorporated into a 
cologne at concentrations of 2.0%, 2.5%, 3.0%, 3.5%, 4.0%, 4.5% and 5.0% 
in 85% aqueous food grade ethanol; and into a handkerchief perfume at 
concentrations of 15%, 20%, 25% and 30% (in 95% aqueous food grade 
ethanol). A distinctive and definite herbaceous, woody, piney aroma is 
imparted to the cologne and to the handkerchief perfume at all levels 
indicated above. 
EXAMPLE VI 
PREATION OF SOAP COMPOSITION 
One hundred grams of soap chips (IVORY.RTM., produced by the Procter & 
Gamble Company, Cinncinati, Ohio) are mixed with one gram of the 
formulation of Example II until homogeneous compositions are obtained. In 
each of the cases, the homogeneous compositions are heated under three 
atmospheric pressure at 180.degree. C. for a period of three hours and the 
resulting liquids are placed into soap molds. The resulting soap cakes, on 
cooling, manifest excellent herbaceous, woody and piney aromas with an 
emphasis on the piney aspects of the aroma. 
EXAMPLE VII 
PREATION OF A SOLID DETERGENT COMPOSITION 
A detergent is prepared from the following ingredients according to Example 
1 of Canadian Pat. No. 1,007,948: 
______________________________________ 
Ingredient Percent by Weight 
______________________________________ 
"Neodol 45-11 (a C.sub.14 --C.sub.15 
12 
Alcohol ethoxylated with 
11 moles of ethylene oxide 
Sodium carbonate 55 
Sodium citrate 20 
Sodium sulfate, water 
q.s. 
brighteners 
______________________________________ 
This detergent is a "phosphate-free" detergent. A total of 100 grams of 
this detergent is admixed with 0.10, 0.15, 0.20 and 0.25 grams of the pine 
perfume of Example II. The detergent sample has an excellent herbaceous, 
woody and piney aroma. 
EXAMPLE VIII 
PREATION OF A COSMETIC POWDER COMPOSITION 
A cosmetic powder is prepared by admixing in a ball mill, 100 g of talcum 
powder with 0.25 g of one of the di-isoamylene compounds prepared 
according to Example I. The resulting cosmetic powder has an excellent 
herbaceous, piney and woody aroma. 
EXAMPLE IX 
PERFUMED LIQUID DETERGENT 
Concentrated liquid detergents (Lysine salt of n-dodecylbenzene sulfonic 
acid as more specifically described in U.S. Pat. No. 3,948,818, issued on 
April 6, 1976) with herbaceous, woody and piney aroma notes are prepared 
containing 0.10%, 0.15%, 0.20% and 0.25% of one or more of the 
di-isoamylenes prepared according to Example I. They are prepared by 
adding and homogeneously mixing the appropriate quantity of di-isoamylene 
composition in the liquid detergent. The detergents all possess piney, 
woody and herbaceous nuances, the intensity of each characteristic 
increasing with greater concentrations of di-isoamylene composition of 
Example I. 
EXAMPLE X 
PREATION OF COLOGNES AND HANDKERCHIEF PERFUMES 
The di-isoamylene derivatives prepared according to Example I are 
incorporated into colognes at concentrations of 2.0%, 2.5%, 3.0%, 3.5%, 
4.0% and 4.5% in 85% aqueous food grade ethanol; and into handkerchief 
perfumes at concentrations of 15%, 20%, 25% and 30% (in 95% aqueous 
ethanol). Distinctive herbaceous, woody and piney nuances are imparted to 
the colognes and to the handkerchief perfumes at various levels indicated 
above. 
EXAMPLE XI 
Utilizing the procedure of Example I of column 15 of U.S. Pat. No. 
3,632,396, a nonwoven cloth substrate useful as a dryer-added 
fabric-softening article of manufacture prepared wherein the substrate, 
the substrate coating and the outer coating and the perfuming material are 
as follows: 
1. a water "dissolvable" paper ("Dissolvo Paper"). 
2. Adogen 448 (m.p. about 140.degree. F.) as the substrate coating; and 
3. An outer coating having the following formulation (m.p. about 
150.degree. F.): 
57 percent C.sub.20-22 HAPS 
22 percent isopropyl alcohol 
20 percent antistatic agent 
1 percent of one or more of the di-isoamylene derivatives of Example I. 
Fabric-softening compositions prepared according to Example I having woody, 
piney and herbaceous aroma characteristics essentially consist of a 
substrate having a weight of about 3 grams per 100 square inches of 
substrate coating of about 1.85 grams per 100 square inches of substrate 
and an outer coating of about 1.4 grams per 100 square inches of 
substrate, thereby providing a total aromatized substrate and outer 
coating weight ratio of about 1:1 by weight of the substrate. The woody, 
herbaceous and piney aroma is imparted in a pleasant manner to the head 
space in the dryer on operation thereof, using the said dryer-added fabric 
softening nonwoven fabric. 
In the following examples, Aromox DMC-W and Aromox DMMC-W are 30% aqueous 
solutions of dimethyl cocoamine oxide; and Aromox NCMDW is a 40% aqueous 
solution of N-cocomorpholine oxide produced by Armac Division of AKZO of 
Chicago, Ill. 
EXAMPLE XII 
Four drops of one of the di-isoamylene compositions prepared according to 
Example I is added to two grams of Aromox DMC-W to produce a clear premix. 
The clear premix is added to 200 grams of CLOROX with stirring resulting 
in a clear stable single phase solution. Sufficient 1 M aqueous NaOH is 
added to bring the pH of the mixture up to 12.8. The solution remains 
substantially stable at 120.degree. F. for a period of seven days. When 
the 5% aqueous sodium hypochlorite solution is used as a laundry bleach, 
the resulting laundry on dry-out in an atmosphere of 65% relative humidity 
yields substantially no characteristic "hypochlorite" odor but does not 
have a faint pleasant "woody/piney/herbaceous" aroma. Furthermore, no such 
characteristic "hypochlorite" aroma is retained on the hands of the 
individual handling such laundry in both the wet and the dry states. 
EXAMPLE XIII 
Aromox DMMC-W in various quantities is mixed with 0.1 gram of one of the 
di-isoamylene compositions prepared according to Example I. The resulting 
premixes are then added to 200 grams of an aqueous 5% sodium hypochlorite 
solution. Sufficient 12.5 M aqueous NaOH is added to bring the pH of the 
mixture up to 13. The following results are obtained: 
______________________________________ 
Percentage Aromox 
Clarity of hypochlorite solu- 
DMMC-W tion after addition of premix 
______________________________________ 
0.23% Clear after three days 
0.15% Clear after three days 
0.08% Initially slightly turbid; 
two phases exist after 
three days. 
______________________________________ 
EXAMPLE XIV 
Two grams of Aromox DMMC-W is admixed with eight drops of one of the 
di-isoamylene compositions of Example I. The premix is then added with 
stirring to 200 grams of a 7% aqueous solution of lithium hypochlorite. 
Sufficient 3 M aqueous LiOH is added to bring the pH of the solution to 
13.4. The mixture is then heated to 120.degree. F. and maintained at that 
temperature with stirring for a period of 1 week. The resulting solution 
remains clear in a single phase. When used as a laundry bleach, the 
resulting bleach laundry on dry-out in an atmosphere of 50% relative 
humidity retains a "clean fresh" woody, herbaceous, piney aroma; whereas 
without the use of the di-isoamylene prepared according to Example I, the 
bleached laundry has a faint characteristic disagreeable "hypochlorite" 
aroma. 
EXAMPLE XV 
Two grams of Aromox DMMC-W is admixed with eight drops of one of the 
di-isoamylene compositions of Example I. This premix is then added, with 
stirring to 200 grams of a mixture containing 4.5% aqueous medium sodium 
hypochlorite and 4.5% aqueous lithium hypochlorite. Sufficient 4 M aqueous 
LiOH is added to bring the pH of the solution of 13.4. The mixture is then 
heated to 120.degree. F. and maintained at that temperature for a period 
of one week. The resulting solution remains clear in a single phase. When 
used as a laundry bleach, the resulting bleached laundry on dry-out in an 
atmosphere of 50% relative humidity retains a "clean fresh", woody, 
herbaceous, piney aroma; whereas without the use of the di-isoamylene 
prepared according to Example I, the bleached laundry has a faint 
characteristic disagreeable "hypochlorite" aroma. 
EXAMPLE XVI 
Two grams of Aromox DMMC-W is admixed with eight drops of one of the 
di-isoamylene products produced according to Example I. This premix is 
then added with stirring to 200 grams of a mixture containing 4.5% aqueous 
sodium hypochlorite and 4.5% aqueous lithium hypochlorite. Sufficient 2 M 
aqueous NaOH is added to bring the pH of the solution to 13.4. The mixture 
is then heated to 110.degree. F. and maintained at that temperature with 
stirring for a period of 2 weeks. The resulting solution remains clear as 
a single phase when used as a laundry bleach. The resulting bleached 
laundry, on dryout in an atmosphere of 50% relative humidity, retains a 
"woody, herbaceous, piney" aroma whereas without the use of the 
di-isoamylene composition of Example I, the bleached laundry has a faint 
characteristic disagreeable "hypochlorite" aroma. 
EXAMPLE XVII 
Four drops of one of the di-isoamylene mixtures produced according to 
Example I, is added to 1.5 grams of ARomox NCMDW to produce a clear 
premix. The clear premix is added to 200 grams of CLOROX with stirring 
resulting in a clear stable single phase solution. Sufficient 1 M aqueous 
NaOH is added to bring the pH of the mixture up to 12.8. The solution 
remains substantially stable at 120.degree. F. for a period of 7 days. 
When the 5% aqueous sodium hypochlorite solution is used as a laundry 
bleach, the resulting laundry on dry-out in an atmosphere of 65% relative 
humidity yields substantially no characteristic "hypochlorite" odor but 
does have a faint pleasant "woody, herbaceous, piney" aroma. Furthermore, 
no such characteristic "hypochlorite" aroma is retained on the hands of 
the individual handling such laundry in both the wet and the dry states. 
EXAMPLE XVIII 
Four drops of one of the di-isoamylene mixtures produced according to 
Example I, is added to 1 gram n-undecyl dimethyl amide oxide to produce a 
clear premix. The clear premix is added to 200 grams of CLOROX with 
stirring resulting in a clear stable single phase solution. Sufficient 1 M 
aqueous NaOH is added to bring the pH of the mixture up to 12.8. The 
solution remains substantially stable at 120.degree. F. for a period of 7 
days. When the 5% aqueous sodium hypochlorite solution is used as a 
laundry bleach, the resulting laundry on dry-out in an atmosphere of 65% 
relative humidity yields substantially no characteristic "hypochlorite" 
odor but does have a faint pleasant "woody, herbaceous, piney" aroma. 
Furthermore, no such characteristic "hypochlorite" aroma is retained on 
the hands of the individual handling such laundry in both the wet and the 
dry states. 
EXAMPLE XIX 
Four drops of one of the di-isoamylene mixtures produced according to 
Example I is added to 1 gram of n-dodecyl dimethyl amine oxide to produce 
a clear premix. The clear premix is added to 200 grams of CLOROX with 
stirring resulting in a clear stable single phase solution. Sufficient 1 M 
aqueous NaOH is added to bring the pH of the mixture up to 12.8. The 
solution remains substantially stable at 120.degree. F. for a period of 7 
days. When the 5% aqueous sodium hypochlorite solution is used as a 
laundry bleach, the resulting laundry on dry-out in an atmosphere of 65% 
relative humidity yields substantially no characteristic "hypochlorite": 
odor but does have a faint pleasant "woody, herbaceous, piney" aroma. 
Furthermore, no such characteristic "hypochlorite" aroma is retained on 
the hands of the individual handling such laundry in both the wet and the 
dry states. 
EXAMPLE XX 
One gram of n-tridecyl dimethyl amine oxide is admixed with eight drops of 
one of the di-isoamyline compositions of Example I. This premix is then 
added with stirring to 200 grams of a 7% aqueous solution of lithium 
hypochlorite. Sufficient 3 M aqueous LiOH is added to bring the pH of the 
solution to 13.4. The mixture is then heated to 120.degree. F. and 
maintained at that temperature with stirring for a period of one week. The 
resulting solution remains clear in a single phase. When used as a laundry 
bleach, the resulting bleached laundry on dry-out in an atmosphere of 50% 
relative humidity retains a "clean fresh, woody, herbaceous, piney" aroma; 
whereas without the use of one of the di-isoamyline compositions of 
Example I, the bleached laundry has a faint characteristic disagreeable 
"hypochlorite" aroma.