CA1037969A - Process for the manufacture of cyano-substituted bis-styryl compounds - Google Patents
Process for the manufacture of cyano-substituted bis-styryl compoundsInfo
- Publication number
- CA1037969A CA1037969A CA213,866A CA213866A CA1037969A CA 1037969 A CA1037969 A CA 1037969A CA 213866 A CA213866 A CA 213866A CA 1037969 A CA1037969 A CA 1037969A
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- Canada
- Prior art keywords
- chlorine
- formula
- hydrogen
- bis
- styryl
- Prior art date
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/315—Compounds containing carbon-to-nitrogen triple bonds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
Abstract of the Disclosure The present invention relates to the manufacture of cyano-substituted bis-styryl compounds, to new cyano-substituted bis-styryl compounds as well as to their use for brightening organic materials.
Description
7~
The present invention relates to the manufacture of cyano-substituted bis-styryl compounds, to novel cyano-substituted bis-styryl compounds and to their use for bright-ening or~anic materials of h:igh molecular wei~ht.
The manufacture of styryl compounds by the anil syn-thesis is taught in British Patents 1 131 484 and 1 222 863.The present invention is based on the surprising observation that, by means of the anil synthesis, it is possible to react toluene derivatives which are substituted in a very specific manner by the cyano group to yield bis-styryl compounds with retention of the cyano group.
Accordingly, the present invention provides a process ~or the manufacture of bis-styryl compounds of ~he formula R2 R2 ~ ~
(I) X2 ~ - CH - CH - A - CH --CH- ~ X2 ' `~ `
R X Xl Rl wherein A represents 1,4-, 1,5- or 2,6-naphthylene, 1,4-phenylene or 4,4'-bisphenyléne, either Xl represents the cyano radical and X2 represents hydrogen,chloride or fluorine or X2 represents the cyano radical and X represents ~ -hydrogen, chlorine or alkyl with 1 to 4 carbon atoms, each of Rl and R2 independently represents hydrogen, chlorine, -~
~A ,~
fluorine or alkoxy with 1 to 4 carbon atom5, which comprises reacting a toluene derivative of the formula ` ~ ~
R2, .
(II) X2- ~ CH3 Rl X
wherein X , X , Rl and R have the meanings assigned to them hereinbefore, with a Schiff's base of the formula (III) ~N = CH--A--CH =N ~3 , ;
,, , Yl , , Y
; wherein Yl represents chlorine or hydrogen, preferably chlorine in the 2-position, and A has the meaning previously assigned to it, in dimethyl formamide and in the presence of sodium alco-holate at temperature of 0C to 40C.
The preferred naphthylene radical is the 2,6-naphth~
lene radical. Preferred alkyl and alkoxy are respectively methyl and methoxy. Fluorine represents by X2, Rl and R2 is of less significance than the other indicated possibilities.
The compounds of the formula (I) which contain in addition to the obligatory cyano radical one or more - ~ubstituents which are different from hydrogen of the kind , ~ .
- 3 - ~ ~
:.. . - . . . ~.
7~
defined in respect of Xl, X2, Rl and R , are novel.
Novel compounds with a particularly interesting utility havc the formula R~ R~
(IV) X4 ~ CH = CH--A -CH = CH ~ ~ X4 R3 3 x3 R~ ^:
wherein one of the symbols X3 and X4 represents the cyano radical and the other represents hydrogen or chlorine, and each of R3 and R4 independently represents hydrogen or ~-: chlorine, but at least one, and at most two, of the symbols X , X , R and R represents chlorine, and wherein A has the meaning previously assigned to it.
` Of primary interest within the scope of the formula ; ~: (IV) are the compounds of the formula ~ ~4 R ~ X3 ~3 wh~rcin X3, X4, and R3 and R4 have the meanings previously assi~ncd to them. -Compounds of the formula -~ 7~9 : .
(Vl) ~ CH = }1 ~ ~ - C}l- Cll CN . CN
.`. ,,~
have a particularly interesting utility in respect of their ;~:~
application for treating spinning masses~ especially those on a polyester basis, with fluorescent brighteners.
The pre~erred compounds of the formulae (IV) and (V) are those in which X3 represents the cyano radical. ;~
The compounds of the formulae (IV) to ~VI) are obtained according to the invention by reaction of a toluene --~
derivative of the formula :
R~
(VII) 4 ~ CH3 `~
or Cl H ~ `
(VIII) ~ CH3 - "~
, with a Schiff's base of the formula (III) or of the formula ~ .
~ ' ~37~
~ - N - C}l- ~ - ~ CH-= N
(IX) 1 Y
wherein Yl has the meaning assigned to it hereinbefore.
- The reaction according to the invention of the ;~
toluene derivative with the Schiff's base takes pla e in the ;~
presence of dimethyl formamide as solvent and of sodium alcoholates.
These sodium alcoholates can be represented by the formula (X) n 2n~1 wherein n is an integer from 1 to 5. Examples of such sodium alcoholates are sodium methylate, sodium ethylate, sodium `~
isopropylate, sodium tert. butylate. The use of sodium methyl-ate is preferred. It is, of course, also possible to use -`~
mixture of such bases . ;~
In general, there are used equivalent to double the equivalent amounts of toluene derivative based on- the amoun~
of Schiff's base, i.e. 2 to 4 moles of toluene derivative for each mole of Schiff's base. Normally, at least the equivalent amount of alcohol is used, i.e. at least 2 moles per mole of ; : . . : ~. ~ . . : .
~3~ 9~ ~
Schiff's ~ase.However, it is advantage~us to use a surplus of alcoholate, for example up to 12 moles per mole of Schiff's base.
The process according to the invention is advantage-ously carried out excluding air at temperatures between 0C and about 40C, preferably between 15C and 30C. On carrying out the reaction at room, temperature, no external supply of heat is necessary. As a rule, the reaction time is from ~ hour to 24 hours.
The final products can be processed from the reaction mixture by conventional methods which are known per se.
The compounds of the formulae (I) and (IV) to tVI) defined hereinbefore can be used for the fluorescent brighten~
ing of organic materials of high molecular weight. They are particularly suitable for spinning masses, in particular for polyester spinning masses. As a rule, 0.001 to 2 per cent by weight preferably 0.01 to O.S per cent by weight of fluorescent brightener of the formula (I) or (IV) to (VI), based on the weight of the polymer, is added to the spinning melts or solutions. . -The following Examples illustrate the invention, but without being limitative thereof. Parts and percentages are by weight.
7~3 EXAMPLE ~
5.37 g of the Schiff's base from 2 moles of o-chloro- : .
aniline and 1 mole of diphenyl-~,4'-dicarbaldehyde of the formula (1) ~ N = CH ~ - CH - N -Cl Cl (melting point: 187.5C to 188C) and 2.93 g of p-tolunitrile ~ ~
are dissolved with stirring in 150 ml of dimethyl formamide -:
and the resultant solution is then cooled to 20~C. After displacement of the air by nitrogen, 2.7 g of sodium methylate are added and the reaction mixture is stirred for 16 hours at : `
20C to 25C excluding air, in the course of which a dark violet colouration occurs gradually. Then 600 ml of methanol are added. The mixture is cooled to 0C to 5C and the preci- -`
pitated product is then filtered off with suction, washed with 100 ml of methanol and dried . Yield : 4.08 g ( 80% of theory) ~
of 4,4'-di-(p-cyano-styryl)-biphenol of the formula ~ :
The present invention relates to the manufacture of cyano-substituted bis-styryl compounds, to novel cyano-substituted bis-styryl compounds and to their use for bright-ening or~anic materials of h:igh molecular wei~ht.
The manufacture of styryl compounds by the anil syn-thesis is taught in British Patents 1 131 484 and 1 222 863.The present invention is based on the surprising observation that, by means of the anil synthesis, it is possible to react toluene derivatives which are substituted in a very specific manner by the cyano group to yield bis-styryl compounds with retention of the cyano group.
Accordingly, the present invention provides a process ~or the manufacture of bis-styryl compounds of ~he formula R2 R2 ~ ~
(I) X2 ~ - CH - CH - A - CH --CH- ~ X2 ' `~ `
R X Xl Rl wherein A represents 1,4-, 1,5- or 2,6-naphthylene, 1,4-phenylene or 4,4'-bisphenyléne, either Xl represents the cyano radical and X2 represents hydrogen,chloride or fluorine or X2 represents the cyano radical and X represents ~ -hydrogen, chlorine or alkyl with 1 to 4 carbon atoms, each of Rl and R2 independently represents hydrogen, chlorine, -~
~A ,~
fluorine or alkoxy with 1 to 4 carbon atom5, which comprises reacting a toluene derivative of the formula ` ~ ~
R2, .
(II) X2- ~ CH3 Rl X
wherein X , X , Rl and R have the meanings assigned to them hereinbefore, with a Schiff's base of the formula (III) ~N = CH--A--CH =N ~3 , ;
,, , Yl , , Y
; wherein Yl represents chlorine or hydrogen, preferably chlorine in the 2-position, and A has the meaning previously assigned to it, in dimethyl formamide and in the presence of sodium alco-holate at temperature of 0C to 40C.
The preferred naphthylene radical is the 2,6-naphth~
lene radical. Preferred alkyl and alkoxy are respectively methyl and methoxy. Fluorine represents by X2, Rl and R2 is of less significance than the other indicated possibilities.
The compounds of the formula (I) which contain in addition to the obligatory cyano radical one or more - ~ubstituents which are different from hydrogen of the kind , ~ .
- 3 - ~ ~
:.. . - . . . ~.
7~
defined in respect of Xl, X2, Rl and R , are novel.
Novel compounds with a particularly interesting utility havc the formula R~ R~
(IV) X4 ~ CH = CH--A -CH = CH ~ ~ X4 R3 3 x3 R~ ^:
wherein one of the symbols X3 and X4 represents the cyano radical and the other represents hydrogen or chlorine, and each of R3 and R4 independently represents hydrogen or ~-: chlorine, but at least one, and at most two, of the symbols X , X , R and R represents chlorine, and wherein A has the meaning previously assigned to it.
` Of primary interest within the scope of the formula ; ~: (IV) are the compounds of the formula ~ ~4 R ~ X3 ~3 wh~rcin X3, X4, and R3 and R4 have the meanings previously assi~ncd to them. -Compounds of the formula -~ 7~9 : .
(Vl) ~ CH = }1 ~ ~ - C}l- Cll CN . CN
.`. ,,~
have a particularly interesting utility in respect of their ;~:~
application for treating spinning masses~ especially those on a polyester basis, with fluorescent brighteners.
The pre~erred compounds of the formulae (IV) and (V) are those in which X3 represents the cyano radical. ;~
The compounds of the formulae (IV) to ~VI) are obtained according to the invention by reaction of a toluene --~
derivative of the formula :
R~
(VII) 4 ~ CH3 `~
or Cl H ~ `
(VIII) ~ CH3 - "~
, with a Schiff's base of the formula (III) or of the formula ~ .
~ ' ~37~
~ - N - C}l- ~ - ~ CH-= N
(IX) 1 Y
wherein Yl has the meaning assigned to it hereinbefore.
- The reaction according to the invention of the ;~
toluene derivative with the Schiff's base takes pla e in the ;~
presence of dimethyl formamide as solvent and of sodium alcoholates.
These sodium alcoholates can be represented by the formula (X) n 2n~1 wherein n is an integer from 1 to 5. Examples of such sodium alcoholates are sodium methylate, sodium ethylate, sodium `~
isopropylate, sodium tert. butylate. The use of sodium methyl-ate is preferred. It is, of course, also possible to use -`~
mixture of such bases . ;~
In general, there are used equivalent to double the equivalent amounts of toluene derivative based on- the amoun~
of Schiff's base, i.e. 2 to 4 moles of toluene derivative for each mole of Schiff's base. Normally, at least the equivalent amount of alcohol is used, i.e. at least 2 moles per mole of ; : . . : ~. ~ . . : .
~3~ 9~ ~
Schiff's ~ase.However, it is advantage~us to use a surplus of alcoholate, for example up to 12 moles per mole of Schiff's base.
The process according to the invention is advantage-ously carried out excluding air at temperatures between 0C and about 40C, preferably between 15C and 30C. On carrying out the reaction at room, temperature, no external supply of heat is necessary. As a rule, the reaction time is from ~ hour to 24 hours.
The final products can be processed from the reaction mixture by conventional methods which are known per se.
The compounds of the formulae (I) and (IV) to tVI) defined hereinbefore can be used for the fluorescent brighten~
ing of organic materials of high molecular weight. They are particularly suitable for spinning masses, in particular for polyester spinning masses. As a rule, 0.001 to 2 per cent by weight preferably 0.01 to O.S per cent by weight of fluorescent brightener of the formula (I) or (IV) to (VI), based on the weight of the polymer, is added to the spinning melts or solutions. . -The following Examples illustrate the invention, but without being limitative thereof. Parts and percentages are by weight.
7~3 EXAMPLE ~
5.37 g of the Schiff's base from 2 moles of o-chloro- : .
aniline and 1 mole of diphenyl-~,4'-dicarbaldehyde of the formula (1) ~ N = CH ~ - CH - N -Cl Cl (melting point: 187.5C to 188C) and 2.93 g of p-tolunitrile ~ ~
are dissolved with stirring in 150 ml of dimethyl formamide -:
and the resultant solution is then cooled to 20~C. After displacement of the air by nitrogen, 2.7 g of sodium methylate are added and the reaction mixture is stirred for 16 hours at : `
20C to 25C excluding air, in the course of which a dark violet colouration occurs gradually. Then 600 ml of methanol are added. The mixture is cooled to 0C to 5C and the preci- -`
pitated product is then filtered off with suction, washed with 100 ml of methanol and dried . Yield : 4.08 g ( 80% of theory) ~
of 4,4'-di-(p-cyano-styryl)-biphenol of the formula ~ :
(2) NC ~ CH = CH ~ - ~ CH = CH - ~ CN ~ ~
, ., . .. .- ` - - ., ~ . , . .. . . . . ~ . . ~
: ~37 ~ ~ g as a brownish yellow powder with a melting point of 269C to 270C. Two recrystallisations from o-diehlorobenzene (fuller's earth) yield 3.2 g (63.9% o~ theory) of light, greenish yellow, glistening needles and spikes which melt at 276C to 277C.
Analysis: C H N (408.48) calculated: C 88.21 H 4.94 N 6.86 found : C 87.90 H 4.97 N 6.75 :~
The following 4,4'-distyryl-biphenyl derivatives can be manufactured in similar manner:
, ., . .. .- ` - - ., ~ . , . .. . . . . ~ . . ~
: ~37 ~ ~ g as a brownish yellow powder with a melting point of 269C to 270C. Two recrystallisations from o-diehlorobenzene (fuller's earth) yield 3.2 g (63.9% o~ theory) of light, greenish yellow, glistening needles and spikes which melt at 276C to 277C.
Analysis: C H N (408.48) calculated: C 88.21 H 4.94 N 6.86 found : C 87.90 H 4.97 N 6.75 :~
The following 4,4'-distyryl-biphenyl derivatives can be manufactured in similar manner:
(3) 4,4'-di-(o-cyano-styryl)-biphenyl; melting point: ~ .
274 to 275 C;
274 to 275 C;
(4) 4,4'-di-(2-cyano-4-chloro-styryl)-biphenyl; melting point:
281 to 282 C; ~ :
281 to 282 C; ~ :
(5) 4,4'-di-(2-methyl-4-cyano-styryl~-biphenyl; melting point; ~:
249 to 250 C;
(~) 4,~-di-(2-cyano-5-methoxy-styryl)-biphenyl;
(7) 4,4'-di-~3-chloro-4-cyano-styryl)-biphenyl;
~8) 4,4'-di-(3-methoxy-4-cyano-styryl)-biphenyl. ;~
- ., With stirring 5.37 g of the Schiff's base ~rom 2 moles of o-~hloroaniline and 1 mole of 4,4'-dicarb~ldehyde of the formula (1) and 3.79 g of 3-chloro-4-methyl-benzonitrile are dissolved in 50 ml of dimeithyl formamide and the resultant solution is then cooled to 20C. After displacement of the air by nitrogen, 5.4 g of sodium methylate are add~d. The reaction ~ ~
product begins to precipitate a~ter about 30 seconds. The ~ `;
reaction is brought to completion by stirring for about 30 ;
. minutes at 20C to 25C. Then 600 ml of methanol are added and the reaction mixture is cooled to 0C to 5C. The product which has precipitated is filtered off by suction, washed with lG0 ml o~ methanol and dried . Yield: 5.1 g (- 8S.5% of theory) o~
4,4'-di- (2-chloro-4-cyano-styryl)-biphenyl of the formula (9) NC~--CH--CH~ CX=C~ CN
lS Cl Cl - .
as a yellow powder with a melting point of 283C to 284C.
Two recrystallisations from o-dichlorobenzene (fuller' 5 earth) yield 3.4 g (=57% of theory) of fine, greenish yellow crystals with a melting point of 296C to 297C.
......... .................................................................. . ' Analysis C30Hl8C12N2 (477~4) c~lculated: C 75,48 H 3,80 N 5,87 found : C 75~23 H 3,84 N 5~76 The following distyryl derivatives can be manufactu-red in similar manner:
(10~ 4,4'-di- (2-cyano-3-chloro-styryl)-biphenyl;
melting point: 315 to 316 C.
(11) 4,4'-di- (2-cyano-5-chloro-styryl)-biphenyl;
melting point: 299 to 300 C. ;
(12) 1,4--di(2-chloro-4-cyano-styryl)-benzene;
melting point: 299 to 300 C. ~: :
(13) 1,4-di- (2-cyano-3-chloro-styryl)-benzene;
melting point: 314 to 315 C. :
(14) 1,4-di- (2-cyano-5-chloro-styryl)-benzene; .
melting point: 309 to 310 C.
(15) 2,5-di- (2-chloro-4-cyano-styryl)-naphthalene;
melting point: > 360 C. . ~;~
(16) 2, 6-di- (2-cyano-3-chloro-styryl)-naphthalene; ~
melting point: 354 to 355 C. ~:
(17) 2,6-di-(2-cyanb-5-chloro-styryl)-naphthalene;
melting point: 358 to 359 C.
. ;
1~37~g~g ,~
.` 100 g of polyester granules of terephthalic acid ethylene glycol polyester are intimately mixed with O.OS g of ~-`
one of the compounds of the formula (2), (3), (4), (5), (10) : 5 or (ll) and the mixture is melted with stirring at 285C.
The melt is spun through conventional spinnerets to yield highly brightened polyester fibres.
It is also possible to add the above mentioned ~ .
compounds to the starting materials before or during the ~ :~
polycondensation to give the polyester. `~
'-~ . '., , . ~:'.
,.
,`, ','~
, " "~
' ~'``''''
249 to 250 C;
(~) 4,~-di-(2-cyano-5-methoxy-styryl)-biphenyl;
(7) 4,4'-di-~3-chloro-4-cyano-styryl)-biphenyl;
~8) 4,4'-di-(3-methoxy-4-cyano-styryl)-biphenyl. ;~
- ., With stirring 5.37 g of the Schiff's base ~rom 2 moles of o-~hloroaniline and 1 mole of 4,4'-dicarb~ldehyde of the formula (1) and 3.79 g of 3-chloro-4-methyl-benzonitrile are dissolved in 50 ml of dimeithyl formamide and the resultant solution is then cooled to 20C. After displacement of the air by nitrogen, 5.4 g of sodium methylate are add~d. The reaction ~ ~
product begins to precipitate a~ter about 30 seconds. The ~ `;
reaction is brought to completion by stirring for about 30 ;
. minutes at 20C to 25C. Then 600 ml of methanol are added and the reaction mixture is cooled to 0C to 5C. The product which has precipitated is filtered off by suction, washed with lG0 ml o~ methanol and dried . Yield: 5.1 g (- 8S.5% of theory) o~
4,4'-di- (2-chloro-4-cyano-styryl)-biphenyl of the formula (9) NC~--CH--CH~ CX=C~ CN
lS Cl Cl - .
as a yellow powder with a melting point of 283C to 284C.
Two recrystallisations from o-dichlorobenzene (fuller' 5 earth) yield 3.4 g (=57% of theory) of fine, greenish yellow crystals with a melting point of 296C to 297C.
......... .................................................................. . ' Analysis C30Hl8C12N2 (477~4) c~lculated: C 75,48 H 3,80 N 5,87 found : C 75~23 H 3,84 N 5~76 The following distyryl derivatives can be manufactu-red in similar manner:
(10~ 4,4'-di- (2-cyano-3-chloro-styryl)-biphenyl;
melting point: 315 to 316 C.
(11) 4,4'-di- (2-cyano-5-chloro-styryl)-biphenyl;
melting point: 299 to 300 C. ;
(12) 1,4--di(2-chloro-4-cyano-styryl)-benzene;
melting point: 299 to 300 C. ~: :
(13) 1,4-di- (2-cyano-3-chloro-styryl)-benzene;
melting point: 314 to 315 C. :
(14) 1,4-di- (2-cyano-5-chloro-styryl)-benzene; .
melting point: 309 to 310 C.
(15) 2,5-di- (2-chloro-4-cyano-styryl)-naphthalene;
melting point: > 360 C. . ~;~
(16) 2, 6-di- (2-cyano-3-chloro-styryl)-naphthalene; ~
melting point: 354 to 355 C. ~:
(17) 2,6-di-(2-cyanb-5-chloro-styryl)-naphthalene;
melting point: 358 to 359 C.
. ;
1~37~g~g ,~
.` 100 g of polyester granules of terephthalic acid ethylene glycol polyester are intimately mixed with O.OS g of ~-`
one of the compounds of the formula (2), (3), (4), (5), (10) : 5 or (ll) and the mixture is melted with stirring at 285C.
The melt is spun through conventional spinnerets to yield highly brightened polyester fibres.
It is also possible to add the above mentioned ~ .
compounds to the starting materials before or during the ~ :~
polycondensation to give the polyester. `~
'-~ . '., , . ~:'.
,.
,`, ','~
, " "~
' ~'``''''
Claims (12)
1. A process for the manufacture of bis-styryl compounds of the formula , wherein A represents 1,4-, 1,5- or 2,6-naphthylene, 1,4-phenylene or 4,4'-bis-phenylene, either X1 represents the cyano radical and X2 represents hydrogen, chlorine or fluorine, or X2 represents the cyano radical and X1 represents hydrogen, chlorine or alkyl with 1 to 4 carbon atoms, each of R1 and R2 independently represents hydrogen, chlorine, fluorine or alkoxy with 1 to 4 carbon atoms, which comprises reacting a toluene derivative of the formula wherein X1, X2, R1 and R2 have the meanings assigned to them hereinbefore, with a Schiff's base of the formula , wherein Y1 represents chlorine or hydrogen and A has the meaning assigned to it hereinbefore, in dimethyl formamide and in the presence of sodium alcoholate at temperatures of 0°C to 40°C.
2. A process according to claim 1, which comprises the use of a toluene derivative of the formula , wherein one of the symbols X3 and X4 represents the cyano radical and the other represents hydrogen or chlorine and each of R3 and R4 independently represents hydrogen or chlorine, but at least one, and at most two, of the symbols X3, X4, R3 and R4 represents chlorine.
3. A process according to claim 1, which comprises reacting a toluene derivative of the formula , wherein one of the symbols X3 and X4 represents the cyano radical and the other represents hydrogen or chlorine, and each of R3 and R4 independently represents hydrogen or chlorine, but at least one, and at most two, of the symbols X3, X4, R3 and R4 represents chlorine, with a Schiff's base of the formula wherein Y1 represents chlorine or hydrogen.
4. A process according to claim 1, which comprises reacting a toluene derivative of the formula with a Schiff's base of the formula , wherein Y1 represents chlorine or hydrogen.
5. A process according to claim 1, which comprises carrying out the reaction in the presence of sodium methylate and at a temperature of 15°C to 30°C.
6. Bis-styryl compounds of the formula wherein A represents 1,4-, 1,5- or 2,6-naphthylene, 1,4-phenylene or 4,4'-bis-phenylene, one of the symbols X3 and X4 represents the cyano radical and the other represents hydrogen or chlorine, and each of R3 and R4 independently re-presents hydrogen or chlorine, and at least one, and at most two, of the symbols X3, X4, R3 and R4 represents chlorine.
7. Bis-styryl compounds according to claim 6, of the formula wherein one of the symbols X3 and X4 represents the cyano radical and the other represents hydrogen or chlorine, and each of R3 and R4 independently re-presents hydrogen or chlorine, and at least one, and at most two, of the sym-bols X3, X4, R3 and R4 represents chlorine.
8. Bis-styryl compounds according to claim 6, of the formula
9. A method of optically brightening organic materials of high molecu-lar weight which comprises applying thereto or incorporating therein a bis-styryl compound as defined in claim 6.
10. A method according to claim 9, in which the styryl compound is as defined in claim 7 and the organic material is a polyester spinning mass.
11. A method according to claim 9, in which the styryl compound is as defined in claim 8 and the organic material is a polyester spinning mass.
12. Organic materials of high molecular weight, which contain 0.001 to 2 percent by weight of a compound as defined in claim 7 or 8.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1624673A CH582134A5 (en) | 1973-11-19 | 1973-11-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1037969A true CA1037969A (en) | 1978-09-05 |
Family
ID=4415656
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA213,866A Expired CA1037969A (en) | 1973-11-19 | 1974-11-15 | Process for the manufacture of cyano-substituted bis-styryl compounds |
Country Status (9)
| Country | Link |
|---|---|
| JP (1) | JPS5084631A (en) |
| BE (1) | BE822271A (en) |
| CA (1) | CA1037969A (en) |
| CH (1) | CH582134A5 (en) |
| DE (1) | DE2453357A1 (en) |
| FR (1) | FR2251549B1 (en) |
| GB (1) | GB1470461A (en) |
| IT (1) | IT1023275B (en) |
| NL (1) | NL7414619A (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3339383A1 (en) * | 1983-10-29 | 1985-05-09 | Bayer Ag, 5090 Leverkusen | DISTYRYLIC COMPOUNDS |
| DE3347576A1 (en) * | 1983-12-30 | 1985-07-11 | Bayer Ag, 5090 Leverkusen | 1,4-BIS (STYRYL) BENZOLES AND THE USE THEREOF AS OPTICAL BRIGHTENERS |
| KR100274871B1 (en) * | 1998-11-12 | 2000-12-15 | 김순택 | Photoluminescence compound and display device adopting photoluminescence compound as color-developing substance |
| CN1364154A (en) * | 1999-02-11 | 2002-08-14 | 西巴特殊化学品控股有限公司 | Bis-styrylbiphenyl compounds |
-
1973
- 1973-11-19 CH CH1624673A patent/CH582134A5/xx not_active IP Right Cessation
-
1974
- 1974-11-08 NL NL7414619A patent/NL7414619A/en not_active Application Discontinuation
- 1974-11-11 DE DE19742453357 patent/DE2453357A1/en active Pending
- 1974-11-12 GB GB4897574A patent/GB1470461A/en not_active Expired
- 1974-11-14 FR FR7437561A patent/FR2251549B1/fr not_active Expired
- 1974-11-15 CA CA213,866A patent/CA1037969A/en not_active Expired
- 1974-11-15 IT IT54070/74A patent/IT1023275B/en active
- 1974-11-18 JP JP49132605A patent/JPS5084631A/ja active Pending
- 1974-11-18 BE BE150571A patent/BE822271A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| BE822271A (en) | 1975-05-20 |
| GB1470461A (en) | 1977-04-14 |
| CH582134A5 (en) | 1976-11-30 |
| FR2251549A1 (en) | 1975-06-13 |
| IT1023275B (en) | 1978-05-10 |
| FR2251549B1 (en) | 1979-02-23 |
| DE2453357A1 (en) | 1975-05-22 |
| NL7414619A (en) | 1975-05-21 |
| JPS5084631A (en) | 1975-07-08 |
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