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Alkylated aminoalkylpiperazine surfactants and their use in photoresist developers
| Details |
Inventors: Lassila, Kevin Rodney; Carr, Richard V. C; Minnich, Kristen Elaine;
Assignee: Air Products and Chemicals, Inc. (Allentown, PA)
Primary Examiner: Le; Hoa Van
Assistant Examiner:
Attorney, Agent or Firm: Leach; Michael
This invention provides water-based compositions, particularly coating, ink, fountain solution, adhesive, agricultural and photoresist developing/electronics cleaning compositions, manifesting reduced equilibrium and dynamic surface tension by the incorporation of a surface tension reducing amount of certain alkylated aminoalkylpiperazine compounds of the structure ##STR1## where one of R.sup.1 and R.sup.2 is a C5-C14 alkyl or cycloalkyl group and the other is H, or both or R.sup.1 and R.sup.2 are C5 to C8 alkyl groups, and n is 2 or 3. |
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DETAILED DESCRIPTION OF THE INVENTION This invention relates to the use of compounds of the formula ##STR7## where one of R.
sup.
1 and R.
sup.
2 is a C5-C14 alkyl or cycloalkyl group and the other is H, or both of R.
sup.
1 and R.
sup.
2 are C5 to C8 alkyl groups, and n is 2 or 3, for the reduction of equilibrium and dynamic surface tension in water-based compositions containing an organic compound, particularly coating, ink, adhesive, agricultural and electronics processing compositions containing organic compounds such as polymeric resins, organic bases, herbicides, fungicides, insecticides or plant growth modifying agents.
It is desirable that an aqueous solution of the alkylated aminoalkylpiperazine demonstrates a dynamic surface tension of less than 45 dynes/cm at a concentration of .
ltoreq.
5 wt % in water at 23.
degree.
C.
and 1 bubble/second according to the maximum-bubble-pressure method.
The maximum-bubble-pressure method of measuring surface tension is described in Langmuir 1986, 2, 428-432, which is incorporated by reference.
In one aspect of the invention the alkylated aminoalkylpiperazines of the above formula display excellent ability to reduce equilibrium and dynamic surface tension while producing substantially no foam.
These materials can be prepared by reductive alkylation of the parent aminoalkylpiperazines with aldehydes and ketones using well-established procedures.
The essential aspects of the preparation are the reaction of an aldehyde or ketone with the aminoalkylpiperazine to make an imine or eneamine intermediate which then reacts with hydrogen in the presence of a suitable hydrogenation catalyst to form the corresponding saturated derivative: ##STR8## The imine or eneamine derivative may be preformed or may be prepared in situ.
The reductive alkylation procedure is the method of choice for the production of these materials, but the products may also be prepared by reaction of an aminoalkyl piperazine with an alkyl halide.
This reaction is illustrated for the reaction of aminoethylpiperazine with an alkyl chloride: ##STR9## where in the product, at least one of R
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