Drug – bio-affecting and body treating compositions – Inorganic active ingredient containing – Heavy metal or compound thereof
Reexamination Certificate
1998-07-22
2002-03-26
Bawa, Raj (Department: 1619)
Drug, bio-affecting and body treating compositions
Inorganic active ingredient containing
Heavy metal or compound thereof
C424S045000, C424S070110, C424S070100, C424S070170, C424SDIG001, C424SDIG002
Reexamination Certificate
active
06361801
ABSTRACT:
FIELD OF THE INVENTION
The present invention relates generally to an alkyl allyl amine, more particularly to a polymer formed from an alkyl allyl amine, and even more particularly the present invention relates to a hair fixative composition utilized in styling gels, mousses or sprays (aerosol or pump) which includes a polymerizate of an alkyl allyl amine. It is preferable that the aqueous hair styling composition of the present invention contain a low concentration of volatile organic compounds (VOCs), with it being preferable that the VOCs make up 80% or less of the overall concentration of the hair spray formulation, and even more preferably that the VOCs make up 55% or less of the overall concentration of the hair spray formulation.
BACKGROUND OF THE INVENTION
Hair fixing or styling formulations are used to hold hair in a particular shape or configuration. They can take the form of, for example, hair sprays (aerosol or pump), styling gels, spray-on gels, or mousses. Hair styling formulations normally form a thin film of hair fixative resin when applied to the hair. This thin film of resin holds adjacent hairs together to retain a particular shape or configuration. When the hair styling composition is formulated as a spray it is most common to use a propellant (i.e. an aerosol) in the hair styling formulation. This normally adds to the overall VOC content of the hair spray formulation.
Hair fixing or styling formulations typically contain one or more volatile organic compound (VOC). VOCs as defined by the Environmental Protection Agency (EPA) contain at least one carbon atom and are typically used as solvents or propellants in the hair styling compositions. VOCs contribute to ground level air pollution in the presence of sunlight and air, and are volatile under ambient conditions. VOCs include, for example, C
1
to C
12
straight or branched chain alcohols such as methanol, ethanol, propanol, isopropanol, or butanol; C
1
to C
12
straight or branched chain hydrocarbons such as methane, ethane, propane, isopropane, isobutane, pentane, isopentane, or butane; or ethers such as dimethyl ether, or dimethoxymethane.
Aerosol hair sprays traditionally were formulated to contain 90-95% VOC in the form of ethanol and hydrocarbon propellants. In April 1996, the EPA published the first nationwide VOC regulations for consumer and commercial products, requiring all hair spray to meet an 80% VOC limit by March 1997. Air pollution issues in heavily populated metropolitan areas such as California are required to have more stringent regulations than the EPA, making these areas the bellwether for mass VOC regulations. The California Air Resources Board has had an 80% VOC limit in effect since 1993 and currently plans to enforce a 55% VOC limit on hair sprays by mid-year 1999. Other states with highly populated areas, such as New York, Connecticut and Texas, have also considered enacting a 55% VOC limit.
The 55% VOC limit is much more of a challenge from a technical perspective than the 80% limit because the addition of large amounts of water to the hair spray formulation negatively affects both the hold performance and spray characteristics of the hair spray. Water impacts hold performance because it contributes to an increase in solution viscosity and surface tension. This results in increased initial curl droop and extends both tack time and dry time. Spray performance is impacted because an increase in viscosity (generally greater than 15 centipoise) of the spray solution leads to coarser, wetter sprays which are inefficient in coating the hair. In addition, the introduction of water causes compatibility problems in the ethanol/hydrocarbon solvent/propellant systems used for hair sprays, and can also lead to corrosion problems in steel cans used as vessels for the hair sprays.
Water can also cause the composition, when sprayed, to form droplets or beads on the hair. These beads leave undesirable visible residue on the hair when dried, and can impart a raspy feel to the hair when combed. Water soluble hair fixative resins, when used in low VOC hair styling formulations, are also more likely to become tacky after being applied to the hair. The water soluble hair fixative resins in a low VOC hair styling formulations may also have poor curl retention properties due to their inability to dry completely when applied to the hair.
These undesirable properties become particularly severe when the hair styling formulation contains 15 weight percent or more water. As a result, hair styling formulators have begun to redesign their hair styling compositions in order to formulate hair styling compositions or hair sprays which achieve low VOC levels, but yet which are acceptable for their intended use. In this regard, hair style formulators have focussed on using solvents which are not classified as VOCs and on developing resins which are suitable in low VOC formulations. A resin is considered suitable when it can be applied to the hair in a carrier at low VOC and form a smooth feeling film and is resistant to cracking or breaking when combed. An example of a low VOC hair styling formulation already developed is U.S. Pat. No. 5,176,898 to Goldberg, et al., which discloses an aqueous hair spray formulation having less than 80 weight percent VOC. The aqueous hair spray formulation contains from 1 to 10 weight percent volatile silicone, preferably cyclomethicone or dimethicone copolyol, from 15 to 40 weight percent water/alcohol solution, from 5 to 60 weight percent propellant, from 1 to 10 weight percent water soluble hair fixative resin, and from 0.05 to 3.0 weight percent neutralizer/plasticizer.
SUMMARY OF THE INVENTION
The present invention is directed to an alkyl allyl monomer and polymers thereof, particularly an alkyl allyl monomers useful in a hairspray formulation. More particularly the present invention is directed to a hair spray formulation which satisfies low VOC standards now in place and those anticipated in the future, and which overcomes a number of undesirable characteristics found in known low VOC hair spray formulations (i.e., decreased hold, increased tackiness, larger particle size, poor spray patterns, increased drying times, instability due to hydrolysis, increased can corrosion and poor compatibility with the solvent.
The present invention is directed to an alkyl allyl amine represented by the formula:
wherein R
1
represents hydrogen or an allyl, R
2
represents hydrogen or methyl, n is an integer from 0 to 6, R
4
, R
5
and R
6
each independently represent a hydrogen atom, an alkyl group having from 1 to 22 carbon atoms, a cycloalkyl group having 3 to 22 carbon atoms, a cycloalkylene (i.e. an aryl group) having 6 to 22 carbon atoms or an alkylaryl group having from 7 to 22 carbon atoms.
It is preferable that at least one of R
4
, R
5
or R
6
represent a substituent other than hydrogen, and more preferable that the alkyl portion of the alkyl allyl amine represented in formula (2) below be a branched alkyl group, more preferably, a tertiary alkyl group, more preferably a tertiary butyl group, and most preferably a tertiary octyl group:
The alkyl group may also include methylene spacers (n≧1) before the alkyl group begins to branch. The alkyl group may also include a hetero atom or a functional group. It is preferable that the alkyl allyl amine be a tertiary octyl mono allyl amine represented by formula (3) below:
wherein R
2
represents hydrogen or methyl.
There appears to be a beneficial effect when the alkyl allyl amines of the present invention are symmetrical. It is speculated that the benefit is due to a more rigid polymer structure. Thus, it is more preferable that R
1
of Formula (1) represent an allyl group, with R
2
and R
3
each independently representing a hydrogen or methyl group, with it being most preferred that R
2
and R
3
be the same, and even more preferred that both R
2
and R
3
both be hydrogen. Formula (4) below illustrates a preferred alkyl diallyl amine which has a substantial degree of “symmetry”:
wherein R
2
and R
3
each independently represe
Carpenter Michael M.
Chen Shih-ruey T.
Ding Hong
Lin Fu-Mei Chen
Parsons Jennifer R.
Bawa Raj
Breininger Thomas M.
Calgon Corporation
Martin Michael B.
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