The invention provides surfactant compounds of formulas I-IX, which can be used in methods for aiding the solubilization, digestion, preparation, analysis, and/or characterization of biological material, for example, proteins or cell membranes. The compounds can also aid in the recovery of peptides generated during protein digestion, particularly for in-gel digestion protocol. Additionally, the compounds can improve enzymatic protein deglycosylation without interfering with downstream sample preparation steps and mass spectrometric analysis. The compounds can be specifically useful as digestion aids that can be decomposed by an acid, by heat, or a combination thereof. Decomposition of the surfactants allows for facile separation from isolated samples, and/or allows for analysis of the sample without interfering with the sensitivity of various analytical techniques.

The invention provides surfactant compounds of formulas I-IX, which can be used in methods for aiding the solubilization, digestion, preparation, analysis, and/or characterization of biological material, for example, proteins or cell membranes. The compounds can also aid in the recovery of peptides generated during protein digestion, particularly for in-gel digestion protocol. Additionally, the compounds can improve enzymatic protein deglycosylation without interfering with downstream sample preparation steps and mass spectrometric analysis. The compounds can be specifically useful as digestion aids that can be decomposed by an acid, by heat, or a combination thereof. Decomposition of the surfactants allows for facile separation from isolated samples, and/or allows for analysis of the sample without interfering with the sensitivity of various analytical techniques.

A salt represented by formula (I):

##STR00001##

In formula (I), R.sup.1, R.sup.2, R.sup.3 and R.sup.4 each independently represent a halogen atom or a perfluoroalkyl group having 1 to 6 carbon atoms, R.sup.5, R.sup.6 and R.sup.7 each independently represent a halogen atom, a hydroxy group, a fluorinated alkyl group having 1 to 6 carbon atoms or an alkyl group having 1 to 12 carbon atoms, and —CH.sub.2— included in the alkyl group may be replaced by —O— or —CO—, m5 represents an integer of 0 to 3, m6 represents an integer of 0 to 3, m7 represents an integer of 0 to 3, R.sup.8 and R.sup.9 each independently represent a hydrogen atom or an alkyl group having 1 to 12 carbon atoms, and —CH.sub.2— included in the alkyl group may be replaced by —O— or —CO—, and AI.sup.− represents an organic anion.

A patterning process, including: forming the first resist film from first resist material containing an acid generator and thermosetting compound having a hydroxy group and/or carboxy group protected by an acid-labile group; forming the second resist film on first resist film from a second resist material containing a metal compound (A) and a sensitizer; irradiating the first and second resist film with a high energy beam or an electron beam to perform pattern exposure to deprotect the hydroxy group and/or carboxy group in a pattern exposed portion of first resist film and to form a crosslinked portion of the component (A) with the deprotected hydroxy and/or carboxy group on the pattern exposed portion; and developing the second resist film with a developer to give a metal film pattern composed of the crosslinked portion. This provides a method for forming a thin film resist pattern with higher resolution and higher sensitivity.

A patterning process, including: forming the first resist film from first resist material containing an acid generator and thermosetting compound having a hydroxy group and/or carboxy group protected by an acid-labile group; forming the second resist film on first resist film from a second resist material containing a metal compound (A) and a sensitizer; irradiating the first and second resist film with a high energy beam or an electron beam to perform pattern exposure to deprotect the hydroxy group and/or carboxy group in a pattern exposed portion of first resist film and to form a crosslinked portion of the component (A) with the deprotected hydroxy and/or carboxy group on the pattern exposed portion; and developing the second resist film with a developer to give a metal film pattern composed of the crosslinked portion. This provides a method for forming a thin film resist pattern with higher resolution and higher sensitivity.

Provided is a novel nanoparticle, a contrast agent for magnetic resonance imaging containing the same, and a zwitterionic ligand compound used in production of the nanoparticle. The contrast agent for MRI of the present invention can be suitably used as a contrast agent for MRI in a medical field. The nanoparticle and the zwitterionic ligand compound of the present invention are applicable to various pharmaceutical compositions and the like, including a contrast agent for MRI, and can be used widely in the fields of pharmaceuticals, biotechnology, and the like, including various diagnosis methods and examination reagents.

Provided is a novel nanoparticle, a contrast agent for magnetic resonance imaging containing the same, and a zwitterionic ligand compound used in production of the nanoparticle. The contrast agent for MRI of the present invention can be suitably used as a contrast agent for MRI in a medical field. The nanoparticle and the zwitterionic ligand compound of the present invention are applicable to various pharmaceutical compositions and the like, including a contrast agent for MRI, and can be used widely in the fields of pharmaceuticals, biotechnology, and the like, including various diagnosis methods and examination reagents.

Sulfate and sulfonate derivatives of unsaturated fatty alcohols, processes for making them, and methods of using them are disclosed. In one aspect, a monounsaturated fatty alcohol composition is made by reducing a metathesis-derived monounsaturated alkyl ester. The fatty alcohol composition is then converted to a sulfate or sulfonate derivative by one or more of alkoxylation, sulfation, sulfonation, and sulfitation. Of particular interest are the sulfate and ether sulfate derivatives. Microscopy studies indicate that the unsaturated sodium sulfates in particular have a lamellar phase that should enable formulation at high actives levels. Sulfate compositions comprising 40 to 60 wt. % of a monounsaturated fatty primary alcohol sulfate and 40 to 60 wt. % of a secondary hydroxyalkyl primary alcohol sulfate are also disclosed. The derivatives and sulfate compositions are valuable for many end-use applications, including, for example, agricultural dispersants, water-soluble herbicides, anionic emulsifiers for agricultural use, hard surface cleaners, light-duty liquid detergents, personal cleansers, gas well foamers for oilfield applications, laundry detergents, enhanced oil recovery compositions, latex paints, and specialty foams.

Sulfate and sulfonate derivatives of unsaturated fatty alcohols, processes for making them, and methods of using them are disclosed. In one aspect, a monounsaturated fatty alcohol composition is made by reducing a metathesis-derived monounsaturated alkyl ester. The fatty alcohol composition is then converted to a sulfate or sulfonate derivative by one or more of alkoxylation, sulfation, sulfonation, and sulfitation. Of particular interest are the sulfate and ether sulfate derivatives. Microscopy studies indicate that the unsaturated sodium sulfates in particular have a lamellar phase that should enable formulation at high actives levels. Sulfate compositions comprising 40 to 60 wt. % of a monounsaturated fatty primary alcohol sulfate and 40 to 60 wt. % of a secondary hydroxyalkyl primary alcohol sulfate are also disclosed. The derivatives and sulfate compositions are valuable for many end-use applications, including, for example, agricultural dispersants, water-soluble herbicides, anionic emulsifiers for agricultural use, hard surface cleaners, light-duty liquid detergents, personal cleansers, gas well foamers for oilfield applications, laundry detergents, enhanced oil recovery compositions, latex paints, and specialty foams.

This invention relates to an anionic-cationic-nonionic surfactant as substantially represented by the formula (I), production and use thereof in tertiary oil recovery. The anionic-cationic-nonionic surfactant of this invention exhibits significantly improved interfacial activity and stability as compared with the prior art. With the present anionic-cationic-nonionic surfactant, a flooding fluid composition for tertiary oil recovery with improved oil displacement efficiency and oil washing capability as compared with the prior art could be produced. ##STR00001## In the formula (I), each group is as defined in the specification.