Cleaning compositions for solid surfaces – auxiliary compositions – Cleaning compositions or processes of preparing – Specific organic component
Reexamination Certificate
1998-10-23
2001-03-27
Hardee, John (Department: 1751)
Cleaning compositions for solid surfaces, auxiliary compositions
Cleaning compositions or processes of preparing
Specific organic component
C510S495000, C554S048000, C562S102000
Reexamination Certificate
active
06207637
ABSTRACT:
BACKGROUND OF THE INVENTION
The present invention relates to compositions based on the reaction product of an alkylenediamine with at least two equivalents of an acrylamidoalkanesulfonic acid or a salt thereof, and formulations containing such material. Such aqueous solutions or dispersions are useful for cleaning soiled articles or surfaces, e.g., for degreasing.
A variety of reaction products of acrylamidoalkanesulfonic acids are known for various uses. British Patent 1,550,420, Aug. 15, 1979, discloses aminodi- and aminopolyalkylamidoalkane sulfonic acids and salts of the formula
R
6
can be a group derived from a polyvalent amine, such as
where Q′ is -[-CH
2
CHR
1
-C(═O)-NH—CR
2
R
3
CR
4
R
5
-SO
3
]
n
M
U.S. Pat. No. 5,115,083, Piedrahita et al., May 19, 1992, discloses catalysts for curing aminoplast compositions. One such catalyst is an acid, or an ammonium or metal salt of a reaction product of at least one amine and a sulfo compound. Sulfo compounds include 2-acrylamido-2-methylpropane sulfonic acid. The amines can be primary or secondary amines, and react by the Michael addition. Exemplified amines are 2-amino-2-methylpropanol and triethyl amine. Other amines include alkylene polyamine represented by the formula
R
6
is independently preferably hydrogen; or an aliphatic or hydroxy-substituted aliphatic group of up to about 30 carbon atoms.
U.S. Pat. No. 5,079,081, Lal, Jan. 7, 1992, and related U.S. Pat. No. 5,101,012, Mar. 31, 1992, disclose compositions and polymer fabrics treated therewith. The composition is prepared by reacting (a) the reaction product of a hydrocarbyl substituted carboxylic acid or anhydride and a polyamine, wherein the reaction product has at least one NH group capable of addition to a double bond, with (b) a sulfo compound such as 2-acrylamido-2-methylpropane sulfonic acid. The sulfo compound is reacted with the amine-containing compound at an equivalent ratio of about (1:1-10), preferably about (1:1-1.1).
SUMMARY OF THE INVENTION
In one embodiment, the present invention provides a composition of matter which is the reaction product of an alkylenediamine, each amino group thereof being a primary or secondary amino group; with at least two equivalents of an acrylamidoalkanesulfonic acid or a salt thereof, wherein each amine nitrogen atom of said alkylenediamine is reacted with a single molecule of the acrylamidoalkane sulfonic acid or salt thereof. In one embodiment, the subject composition can be represented by the structure
wherein n is 2 to 6; R
1
and R
7
are each independently hydrogen, hydrocarbyl groups, hydroxyhydrocarbyl groups, alkoxyhydrocarbyl groups, aminohydrocarbyl groups, aminohydrocarbyl groups wherein the amine nitrogen is substituted by
alkoxy-terminated or amine-terminated polyether groups, or a mixture thereof; R
2
through R
6
are each independently hydrogen or hydrocarbyl groups, and each X is independently hydrogen, metal, or ammonium or substituted ammonium.
The present invention further provides a method of cleaning a soiled article or surface, comprising contacting with said article or surface an aqueous solution or dispersion of a composition of matter represented by the structure
wherein n is 2 to 6; R
1
and R
7
are each independently hydrogen, hydrocarbyl groups, hydroxyhydrocarbyl groups, alkoxyhydrocarbyl groups, aminohydrocarbyl groups, aminohydrocarbyl groups wherein the amine nitrogen is substituted by
alkoxy-terminated or amine-terminated polyether groups, additional groups of the structure
or mixtures thereof; R
2
through R
6
are each independently hydrogen or hydrocarbyl groups; and each X is independently hydrogen, metal, or ammonium or substituted ammonium.
DETAILED DESCRIPTION OF THE INVENTION
Various preferred features and embodiments will be described below by way of non-limiting illustration.
In one embodiment, the composition which is a subject of the present invention is the reaction product of an alkylenediamine, each amino group thereof being a primary or secondary amino group; with at least two equivalents of an acrylamidoalkanesulfonic acid or a salt thereof, wherein each amine nitrogen atom of said alkylenediamine is reacted with a single (that is, one) molecule of the acrylamidoalkane sulfonic acid or salt thereof.
Alkylene diamines are well known materials having a general structure H
2
N-(C
n
H
2n
)-NH
2
in their unsubstituted form. In this formula, n is a number of at least 2, generally 2 through 6, preferably 2 through 4, and in one preferred embodiment, 3. Such materials correspond to ethylene diamine, propylene diamines, butylene diamines, pentylene diamines, and hexylene diamines (such as hexamethylene diamine), and include both the normal or linear materials as well as the branched materials. The nitrogen atoms can be located in the &agr;,&bgr; positions or in other positions such as the &agr;,&ohgr; positions, as in the case of 1,3-propylene diamine, which is a preferred material.
The diamine in the present invention is preferably an N-substituted alkylenediamine, that is, one in which one hydrogen atom of one or of both of the nitrogen atoms is replaced by an atom other than hydrogen. The substituted alkylenediamine can then be represented by the structure R
1
NH-(C
n
H
2n
)-NHR
7
, where R
1
and R
7
are each independently hydrogen, hydrocarbyl groups, hydroxyhydrocarbyl groups, alkoxyhydrocarbyl groups, aminohydrocarbyl groups, aminohydrocarbyl groups wherein the amine nitrogen is substituted by
alkoxy-terminated or amine-terminated polyether groups, or a mixture thereof. For the substituted material, at least one of R
1
and R
7
is other than hydrogen. If R
1
or R
7
contain an amino group, then by a strict definition the overall molecule might not be called a “diamine,” yet for the purposes of the present invention, such materials will be considered to be diamines.
In the preferred material, the diamine is monosubstituted by a hydrocarbon group or an alkoxyalkyl group such as an alkoxypropyl group. The preferred hydrocarbon substituent is an aliphatic hydrocarbon group containing 1 to 30 carbon atoms, preferably 4 to 24 carbon atoms, more preferably 8 to 18 carbon atoms. In one embodiment, R
1
can be the hydrocarbon group or mixture of hydrocarbon groups corresponding to the hydrocarbon portion of cocoamine, tallowamine, or oleylamine. The length of the hydrocarbon substituent will affect to some extent the properties of the resulting compound. When a relatively long hydrocarbon substituent is used, e.g., having 10 or 12 to 18 or more carbon atoms, the hydrocarbon portion will impart a measure of hydrophobic character to the composition and the composition will tend to have the properties of a surfactant. When a relatively short hydrocarbon substituent is used, e.g., having 4 to 10 or 12 carbon atoms, the composition will have the properties of a hydrotrope, that is, a material which can serve to increase the solubility of a nonionic surfactant in a formulation.
In a preferred embodiment, the N-substituted alkylenediamine is a mono-N—C
10-18
hydrocarbon-substituted propylene diamine. In another preferred embodiment, the N-substituted alkylenediamine is a mono-N—C
4-10
hydrocarbon-substituted propylene diamine.
The diamine is reacted with at least two equivalents of an acrylamidoalkanesulfonic acid or a salt thereof. Acrylamidoalkanesulfonic acids and salts are materials represented by the formula
in which R
2
through R
6
are each independently hydrogen or hydrocarbyl groups, and X is hydrogen, metal, or ammonium or substituted ammonium. In the preferred embodiments, R
2
is hydrogen or a lower hydrocarbyl or alkyl radical and each of R
4
, R
5
, and R
6
is independently hydrogen or an alkyl or hydrocarbyl radical, and R
3
is hydrogen, an alkyl or hydrocarbyl radical, or an SO
3
H -substituted alkyl group. The term “lower” as used in this context designates radicals containing up to 7 carbon atoms. The term “acrylamidoalkanesulfonic acid” thus includes derivatives of methacrylic acid (where R
2
is methyl), ethacrylic acid, and the
Grisso Bryan A.
Jahnke Richard W.
Pike Philip W.
Esposito Michael F.
Hardee John
Shold David M.
The Lubrizol Corporation
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