Benzyl­tributyl­ammonium 6-hydroxy­naphthalene-2-sulfonate

Kazuya Uta; Yohei Sato; Jin Mizuguchi

doi:10.1107/S1600536809001329

. 2009 Jan 17;65(Pt 2):o319. doi: 10.1107/S1600536809001329

Benzyltributylammonium 6-hydroxynaphthalene-2-sulfonate

Kazuya Uta ^a, Yohei Sato ^a, Jin Mizuguchi ^a,^*

PMCID: PMC2968198 PMID: 21581924

Abstract

The title compound, C₁₉H₃₄N⁺·C₁₀H₇O₄S⁻, is a charge-control agent for toners used in electrophotography. Intermoleclar O—H⋯O hydrogen bonding between the OH group of one anion and the sulfonate O atom of a neighboring anion leads to the formation of one-dimensional chains along the b axis. In addition, C—H⋯O hydrogen bonds are observed. One of the n-butyl chains of the cation is disordered over two sites in a 0.88:0.12 ratio.

Related literature

For general background to charge-control agents for toners, see: Nash et al. (2001 ▶). For a related structure, see: Mizuguchi et al. (2007 ▶).

Experimental

Crystal data

C₁₉H₃₄N⁺·C₁₀H₇O₄S⁻
M _r = 499.70
Monoclinic,
a = 16.9616 (4) Å
b = 10.4422 (2) Å
c = 17.6700 (4) Å
β = 116.2570 (11)°
V = 2806.73 (11) Å³
Z = 4
Cu Kα radiation
μ = 1.28 mm⁻¹
T = 296.1 K
0.50 × 0.25 × 0.04 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T _min = 0.720, T _max = 0.954
24483 measured reflections
5103 independent reflections
2818 reflections with F ² > 2σ(F ²)
R _int = 0.032

Refinement

R[F ² > 2σ(F ²)] = 0.055
wR(F ²) = 0.191
S = 1.10
5103 reflections
328 parameters
H-atom parameters constrained
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.40 e Å⁻³

Data collection: PROCESS-AUTO (Rigaku, 1998 ▶); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2006 ▶); program(s) used to solve structure: SIR2004 (Burla et al., 2003 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ▶); software used to prepare material for publication: CrystalStructure.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809001329/ci2755sup1.cif

e-65-0o319-sup1.cif^{(28.1KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809001329/ci2755Isup2.hkl

e-65-0o319-Isup2.hkl^{(249.9KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4O⋯O2ⁱ	0.82	1.88	2.696 (3)	177
C12—H12B⋯O2ⁱⁱ	0.96	2.52	3.470 (4)	173
C16—H16B⋯O3ⁱ	0.98	2.34	3.251 (4)	155

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Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

The authors express their sincere thanks to Mr O. Yamate at Orient Chemical Industries, Ltd. for the preparation of the sample.

supplementary crystallographic information

Comment

Quaternary ammonium salts (for example, benzyltributylammonium 4-hydroxynaphthalene-1-sulfonate: P-51 from Orient Chemical Industries) are well known charge-control agents (CCAs) for toners used in electrophotography. CCAs are usually added to toners to create a desired charge level and polarity (Nash et al., 2001). The above compounds are characterized by high melting point above 433 K. The present high thermal stability is required for the toner manufacturing process which includes kneading of various toner components such as polymer, colorant, wax and CCA at 403–453 K. However, ordinary quaternary ammonium salts used in electrochemistry as supporting electrolytes exhibit much lower melting points below 373 K. Previously, we have investigated why P-51 alone possesses such a high melting point from the standpoint of the crystal structure. Then, we found chains of O—H···O intermolecular hydrogen bonds between the OH group of one anion and the sulfonate O atom of the neighboring one (Mizuguchi et al., 2007). The formation of the hydrogen bond is found to be responsible for the high thermal stability of P-51. A s an extension of this study, the present paper deals with the structure of the title compound, which is one of the P-51 derivatives.

Fig. 1 shows the ORTEPIII plot (Burnett & Johnson, 19966) of the title molecule. The ions have no crystallographically imposed symmetry. Fig. 2 shows a hydrogen-bonded anionic chain along the b axis between the OH group of one anion and the sulfonate O atom of the neighboring one. In addition, C—H···O hydrogen bonds are observed in the crystal structure (Table 1). The hydrogen-bonding network is found to greatly contribute to the high melting point of the title compound (433 K), just as in the case of P-51 (462 K).

Experimental

The title compound was obtained from Orient Chemical Industries Ltd., and was recrystallized from a methanol solution. After 48 h, a number of colourless crystals were obtained in the form of platelets.