NL8104757A - ONE OR TWO COMPONENT DIAZOTYPIE MATERIAL. - Google Patents

Description

VO 238 ^

One or two component diazotype material.

The invention relates to a diazotype material with improved light stability of the image dyes.

The image dyes of. Diazotype materials have been subjected to a significant load by irradiation in the reader and by duplicating diazo materials on diazo materials. Therefore, in addition to maintaining all other essential properties, such as sensitivity, resolution, coupling activity and duplicability, the light stability of the dyes is an essential parameter of efficiently operating diazo systems.

10 It is possible to a limited extent by suitable substitution. diazonium and / or coupler components improve the bleaching resistance of the azo dyes formed. However, the effect of this is only minor, while the synthesis is rather laborious.

It has therefore proved more favorable to add certain compounds to the diazo-15 system which reduce bleaching under the conditions prevailing in the reading and exposure apparatus. In addition, these bleach inhibitors must meet several additional conditions, such as be compatible with the system, have an appropriate absorption maximum (absorb as much as possible in a shorter wavelength range than the diazo components), be stable in the processing process and be easily accessible. To date, sterically hindered phenols (DE-PS 1,772.9S1), ethylenediamines (DS-AS 1,797,322) and 3-anilinopyrazoins (DD-WP G 03 c / 221.629) have been used as additives. The disadvantage of these compounds consists in the rather low activity and in part also in the cumbersome synthesis required for the preparation of the compounds. Phosphoric anilides (DD-WP G 03 c / 222.0ö2) are fairly easy to prepare, but have an adverse effect on duplicability. It is inherent in all the compounds described so far that they only maintain light stability for a certain period of time, but they are not decomposed themselves.

The object of the invention is to considerably improve the light stability of diazo materials.

The compounds hitherto used to increase the light stability have the drawback that. they show too little effect in the long run.

The object of the invention is to find additives for diazotype materials, which stabilize the image dyes in such a way that even with light effect for several hours no or only slight bleaching effects occur. All other properties of the material must be retained. Which. the object is achieved according to the invention in that it contains one or two-component endiazotypic material with bleaching creme, one or more Cu (II) salts of organic carboxylic acids.

. It can be used. Cu (. II) salts of organic carboxylic acids,. such as e.g. straight-chain saturated aliphatic mono-carboxylic acids (capric acid), branched saturated aliphatic (methyl-ethyl-acetic acid), straight-chain, unsaturated aliphatic (propiolic acid), branched 15 unsaturated aliphatic (inethacrylic acid), aromatic (salicylic acid), ar-aliphatic (mandelic acid), cyclic aliphatic (cyclohemanecarboxylic acid), heterocyclic (isonicotinic acid), saturated aliphatic dicaronic acids (adipic acid), unsaturated aliphatic (malexic acid), aromatic (phthalic acid), hydromycarboxylic acids (lactic acid), halocarboxylic acids (α, β-dichloro-20-propionic acid) (henzic acid) and tricaronic acids (citric acid). The Cu (II) salts are synthetically readily accessible (Gmelins Hand-buch der Organisehen Chemie, Bd .. Cu) and when used as inhibitors lead to a significant increase in the lightfastness of the diazo materials. They exhibit good compatibility with the system, so that all other requirements of a diazo system, such as duplicability, thermal stability and sensitivity, are fully met.

The copper salts are mixed with a diazonium salt, a., To prepare a diazotype casting solution. stabilizing acid and optionally with one or more couplers and then dissolved in a polymer solution. This casting solution is then applied to a support. Suitable diazonium salts include 2-aminobenzenediazonium, k-aminobenzenediazonium, U-thiobenzenediazonium salts and phenylenediamine. Suitable couplers are all known couplers which contain a hydroxyl group in the o-position, such as e.g. 2-hydromy-3-naphthamide, 2,3-dihydroxynaphthalene, resorcinol and β-naphthol. Cellulose derivatives, vinyl polymers, copolymers of vinyl 8104757 3 ** v * can be used as the binder.

chloride and vinyl acetate, polystyrenes, copolymer and of alkyl acrylate and and acrylic acid and polyethylene oxides. The material may also contain the usual additives, such as a stabilizing acid, development accelerators and plasticizers. Carrier materials for the photosensitive layer 5 may be polymeric films from e.g. polyethylene terephthalate, cellulose triacetate, further paper, "transparent paper, glass and metal.

The invention is further elucidated by means of the following example.

Example —2 10 A diazo system of 4.5-10 mol of diazonium salt, 5.3 x -2 -2 -3 -1 10 mol of coupler, 1.7-10 mol of p-toluenesulfonic acid and 10 to 10 mol of 3

Cu (11) salts of an organic carboxylic acid were applied in 1000 ml of a 10 # * cellulose acetate solution. This solution was poured 2 onto 10-15 m of polyethylene terephthalate backsheet to obtain a transparent film. The image dye was formed by development in basic medium and subjected to a Xeno test for 15 hours. The results are shown in the table below. As diazonium salt and the following compounds were used: (I) 2,5-diethayay-4-morpholino-benzenediazonium tetrachloroborate 20 (II) 2,5-dibutoxy-4-morpholino-benzenediazonium tetrachloroacetate, as coupler: (1) 2-hydroxy- 3-naphthoic acid-o-anisidide (2} 2-hydroxy-3-naphthoic acid- [2,4-dimethoxy-5-chloro anilide] (3) 2-hydroxy-3-naphthoic acid- [2-methyl-4-chloroanilide] 25 (4) 2-hydroxy-3-naphthoic acid- [2-methyl-4-methoxyanilide] (5) 2-hydroxy-3-naphthoic acid- [2-methyl-3-nitroanilide] (6) resorcinol (7) 0- naphthol.

__ 8104757 k- S-i o 43 ra g S ^ ¾¾.¾¾ ¾¾.¾¾.¾¾¾¾ ϊί. Q. H ^ ^ ¾.

0 .0 · r- ON O O r- 0 \ -4 * “Ό CO CM t- 0 O w ΙΛ w 0 \ ΙΛ 1Λ J CM IA CM -S '+4 -S' 0 & ^

& 0 S3 0 -P O +3 W N

Ö 0 0 -P

o o M C! ^

000 ftX +3 MO

000 ^ ¾¾¾¾¾¾¾% ¾% .¾¾. ^ ¾¾.¾¾.¾¾.¾¾ ΪΛ -¾¾.

J Jj ti

p 3 O IA O O OO CO O O O IA CM O

+ 5 + 3 * - r- 1 * · • H IA 0 d f-s; & cd --- * ·

H VO VO VO

Pt

Jj * r · r \ fl t- W W Cl r ~ T- VO LA τ ~ τ- Ρ m § +3 3 0 CQ Η 0

0 0 HHHH HH HHH H

«0 OO HWHHHHH HHHH Η H

N ft £ 4 0 3

• t-i O

Ö o Η Η Η Η Η Η H ^ ^ 'd ^ ^ 0000000 OQOO O O, 3 3 33333 SSSS 3 3

<Ö CM CM CM CM CM CM CM CMCUCMCM CM CM

• H I I 1 I I I I 1111 II

0 0000000 * 0000 o o e {r · r— τ— t— ► * - r- τ— r— t— r- t— O) ... * ··· * ··· * *

<D

> NO CO IA CO t- CO CO ON CM CM CM co 1-

0 CO t- UO C— -4 'r · * * “OC ~ C ~ t ~ C— CM

^ Q λ η λ «λ λ Λ η λ ft * A

0.5 t \ i W Ο 4 σ \ CM CM CMt- ’~ t“ CM CM

-P

ra 0 -Ρ +3 Ρ 0, -¾ • Η 0 +5 0 ρ ö 5 2¾¾ u ο ® ö 0 0 5 · Η Η ο 0 0 0 ft> ϊ 54 +3 fj OO +3 ft 0 0 3? Η 0 0 0 0 0ft po 0 Η

0 1 II II

G. , .— '.—,

H HHHH

H HHHH

3 3 3 3 3 £ +3 0 0 ÏSJ *> P Sj 0 Ρ Λ 0 0 0-0 + 3 Ü0 p ra 60 p cm 0 «k · Η · Η 0> -

> 0 0 +3 Ό +3 O

O O 0 0 p

Ö Ρ O «Η N 0 I

S U 0 «H 0> 0 0 O H O 0 *“

<0 g 0> O O

8104757 .....- 5

Vi 0 a 1 «« V. Η ^ Η ^ Η Η H -¾¾¾¾.

ai ^ t— ^ o o c \ ~ τ-νοσ \ * - ί2 5 v cm ia co ir \ co on ir \ cm co m oj On

D

<D <73 60 C ai +3 O +3 m n C <u <u -P

0 o. u s Vi <u υ o a M g 3) §i K H W -¾¾.¾¾¾¾.¾¾ ^ .¾¾

'□ yyk CO O O O O C \ CO O CO <~ irvO

+ 3 + 3'S »1 6 -

Ss - ^ r-f NQ ^ <0 ^ 60 Pi ^ ^ _ O O C C H CU ^? Ci £ .i23 -Cw

YOU

<a> è +3 3 3 pj'dö Μ H W W W η η Η H ,, | ~ j

OO H M f-i Μ Η H HHHH HiH

Ή t) ft 3 S «· Η O

O o <

Hr + HHi — li-f '^ {' λ'λ'ο η λ OOOOOQ OQQO 00 ssssss sss a & s Ό CM CM OJ 04 OJ OJ OJCMCMOO 'v10! 1 • S' o 'o' o 'o' o 'o' o 'o' oo 'o' o S3 r- t- r <- <- r- r- r- - r- r- «............

£ t— VO O VO O Ό O O O! A OO

S C— CM IA CM CA CM C \ On ON IA O O

¢., Q A · II «n> i" "" * * o a cnoj’-oj'-cM r · r— * - \ o σ \ i- +3 "* 3 d +3

t a II

£ H ld o H

Se aJ g>? C5 ^ <lï ü 3 S -Η H o <0 la o a ^ 3 i i '^ c. , u-1 H W Hl H Hl H W_ rj Ξ3 3 ^ O α O o +> 3 3 3 3 a o 6J «tJ" 'Ö 2— S3 Ij ca * 3 a 60 S + i a ®

3 o o a o o -h a o o o * H

pp anöo o araa ^ aMa-p aj tj fj .η -H ar— u · η o cn j, Γί is t> - Saairfo Ss aa 3a 3 Vi O o 3 3 3 ϋ3ί-ι? · ιθ3ο · Ρ 3 3 OV fcj a I ovoo os 2 'pu U 3 Η UU SiSi S? en · 33 o a <u o a · oasis o «2¾ <JCJ g 3>> O S« J O O S® S3 8104757 • "............. 6 Η

O

* P

"11¾¾ ^ · 65. ^ ¾¾.¾¾¾¾¾¾.

0 .yy N— 1— T * ~ r ~ v— r— dj _4 * LA ΙΛ ΙΛ ΙΛ UN ΙΛ ΙΛ Ö fa 0 4) * d ω a

«Β +5 O + a to N

a 0 0 43 o o fa a h 0 0) o S4 * £ 1¾ Λ 2 3 1¾¾ ^ s. -¾¾ ^ ¾¾¾¾¾¾¾¾¾ p ^ ^ co t- ON t- oo co co + 3 + 3 r- t- T- Ol CV1 r- T- • 4 1Λ ® D «“ g -— H MU) HP, _ OQ, N ^ ^ ^ SO T— r- T- T »» - t— 1—

Stó "w" ^ - WW * - "W

0> § 43, .3 c

Η Η O

H§B h h h hhhhh

NP, Η H H HHHHH

W «5 g • HO.

«A a a Ê4

Η Η H HHHHH

O O O O O O O O

g g s aaass

"Ö CU CU CU CU CU CU CU CU

• H I II I I I I I

(U o o o o o o o r <r- T— t— r— r- r- 1

H

O · · ♦

> r- ^ LTS O LA O CO

(U o OJ CO CM CV IA CO OJ

0 t% A A A A A A A

0.0 CO · t— r- T-T— "T— -r-T—

-P

03 + D

o) S -y S g s • Η O +3 43 43

a a a +3 43 43 a 43 O

a%, aaaaaa 0 43 8 aa aa ^ a-rj 0 oo 0 h? 4 0 43 a Ο Η hh a + 3pyo a λ aa 43 · η> 3 a «a 0 aa η α p, η · η a 1 1 1 2 1 2 ^ - - ·

ö H H * ”h HHHHH

Η Η H HHHHH

'a' a 'a -' a ^ Ί2 'p' p 0 0 0 uooOo I & fa h - «a

a a p a N

43 a a 0 a b 3 3 S3 0 n - 0 0 a * a ^ p a 420 43¾ a 43 0 a a 42 a, a to p, 0 «b ·? a 0 0 so 43 ncjh 65 ο · η no aaa aa rüwo-H amaaahaa 0 paa 3 N a · Η H 43 ΟΗ · Η Ο · Η 3 Ο * HA a £ *> Ü;> aa 43 a μ 43 + 3 -0 434365 4343 aawp 0 aa 43 paaaaaaaa 03 SP ^ H43 oh a 3h64 Sato as 0 0 a 0

a P a · η 43 w ο · Η a a · η> a ο · η η -Ο -P

aa oH00'HH0 * HHa'rjapa> j0 <30 g a g w ό a> -aao na +3 & a 43 8104757

Claims (3)

One- or two-component diazotype material with bleaching inhibitors, characterized in that the bleaching inhibitor material contains one or more Cu (H) salts of organic carboxylic acids. A one or three component diazotype material with bleaching inhibitors according to claim 1, characterized in that the bleaching inhibitor material contains one or more Cu (II) salts of organic monocarboxylic acids. One- or two-component diazo typology with bleaching inhibitors according to claim 1, characterized in that the material as 10 bleaching inhibitor contains one or more Cu (II) salts of organic dicarbonzurai. One or two-component diazotype material with bleach inhibitors according to claim 1, characterized in that the bleach inhibitor material contains one or more Cu (11) salts of organic tri-carboxylic acids. v 4 8104757