Distyryl compounds

• US 4,317,782 A
• Filed: 02/22/1979
• Issued: 03/02/1982
• Est. Priority Date: 02/22/1978
• Status: Expired due to Term

• Current Assignee: Bayer AG
• Original Assignee: Bayer AG
• Inventors: Eckstein, Udo, Siegel, Edgar
• Primary Examiner(s): Sutto, Anton H.
• Application Number:
  US06/013,894
• Time in Patent Office: 1,104 Days
• Field of Search: 260/932, 260/956, 260/346.22, 260/940, 260/941, 260/947, 260/951, 260/465 K, 260/505 C, 542/412, 560/8, 560/14, 562/429, 562/465
• US Class Current: 558/162
• CPC Class Codes: C07F 9/3229 Esters of aromatic acids (P-C aromatic linkage)
• CPC Class Codes: C07F 9/3834 Aromatic acids (P-C aromatic linkage)
• CPC Class Codes: C07F 9/4021 Esters of aromatic acids (P-C aromatic linkage)
• CPC Class Codes: C07F 9/4056 Esters of arylalkanephosphonic acids C07F9/4025 takes precedence
• CPC Class Codes: C07F 9/5325 Aromatic phosphine oxides or thioxides (P-C aromatic linkage)
• CPC Class Codes: D06M 13/288 Phosphonic or phosphonous acids or derivatives thereof
• CPC Class Codes: H01S 3/20 Liquids
• CPC Class Codes: H01S 3/213 including an organic dye

Abstract

Distyryl compounds of the formula ##STR1## wherein A denotes 1,4-phenylene, 4,4'"'"'-biphenylylene, 4,4"-terphenylylene, 1,4-, 1,5- or 2,6-naphthylene, 9,10-dihydro-2,7-phenanthrenylene or 2,7-dibenzofuranylene,

R¹ denotes an optionally functionally modified phosphonic acid, phosphonyl or phosphinyl group,

R² denotes hydrogen, an optionally functionally modified phosphonic acid, phosphonyl or phosphinyl group, sulpho, carboxyl, alkoxycarbonyl, aryloxycarbonyl, aralkoxycarbonyl, aminocarbonyl, cyano, halogen, alkyl, aralkyl, alkenyl, hydroxyl, alkoxy, aralkoxy, cycloalkoxy, aryloxy or alkylmercapto and

R³ and R⁴ denote hydrogen, halogen, alkyl, alkenyl, aryl, aralkyl, alkoxy, alkoxycarbonyl, aminocarbonyl, cyano, sulpho, aminosulphonyl, acyl, acylamino, hydroxyl, aryloxy, aralkoxy, alkenyloxy, carboxyl or acyloxy

and wherein

the cyclic and acyclic radicals can contain non-chromophoric substituents, processes for the preparation of these compounds and their use for whitening synthetic, semi-synthetic and natural organic, high-molecular materials and for the production of laser radiation.

Claims

1. Distyryl compounds of the formula (II) ##STR35## wherein B denotes 1,4-phenylene, 4,4'"'"'-biphenylene, 1,4- and 2,6-naphthylene, 9,10-dihydro-2,7-phenanthrenylene or 2,7-dibenzofuranylene,

R⁵ denotes a radical of the formula ##STR36## R⁶ denotes hydrogen, chlorine, C₁ -C₄ -alkyl, sulpho, carboxyl, C₁ -C₄ -alkoxy, C₁ -C₄ -alkoxycarbonyl, cyano or a radical of the formula ##STR37## R⁷ and R⁸ denote hydrogen, chlorine, C₁ -C₄ -alkyl, phenyl which is optionally substituted by methyl, methoxy or chlorine, C₁ -C₄ -alkoxy, C₁ -C₄ -alkoxycarbonl, cyano, C₁ -C₄ -alkylsulphonyl, C₁ -C₄ -alkylcarbonyl, hydroxyl or carboxyl, R⁹ and R¹⁰ denote C₁ -C₄ -alkyl, benzyl, phenyl which is optionally substituted by methyl, methoxy or chlorine or a group of the formula (OCH₂ CH₂)_n -OR¹¹ wherein

R¹¹ is hydrogen, C₁ -C₄ -alkyl, benzyl or phenyl and

n is 0 to 7,

it being possible for the phosphonic acid group also to be in the form of a salt.

2. Distyryl compounds according to claim 1, of the formula (III) ##STR38## wherein D denotes 1,4-phenylene, 4,4'"'"'-biphenylylene or 9,10-dihydro--2,7-phenanthrenylene and R¹² denotes hydrogen, chlorine, C₁ -C₄ -alkyl, phenyl, C₁ -C₄ -alkoxy, C₁ -C₄ -alkoxycarbonyl, cyano, C₁ -C₄ alkylcarbonyl, hydroxyl or carboxyl or a radical of the formula ##STR39## in which R⁹ and R₁₀ have the meaning given in claim 2.

3. A distyryl compound according to claim 1 wherein B denotes 1,4-phenylene or 4,4'"'"'-biphenylene.