Claims
- 1. A process for preparing a light-sensitive naphthoquinonediazide-sulfonic acid ester which is non-explosive, comprising the steps of (I) reacting a naphthoquinonediazidesulfonyl halide in the presence of a base and a solvent with a mixture comprising:
- A. a polymeric compound having recurring units, each of said recurring units containing at least one phenolic hydroxyl group, and
- B. a low molecular weight compound corresponding to the formula ##STR2## wherein (1a) R denotes a single bond or one from the group consisting of CO, S, O, SO.sub.2 and CR.sub.6 R.sub.7 ;
- (b) R.sub.1, R.sub.2, R.sub.3, and R.sub.5 represent hydrogen, halogen, hydroxyl groups, alkyl groups having 1 to 4 carbon atoms or alkoxy groups having 1 to 4 carbon atoms; and
- (c) R.sub.6 and R.sub.7 represent hydrogen or alkyl groups having 1 to 4 carbon atoms; or wherein
- (2a) two of the radicals R.sub.3, R.sub.4, and R.sub.5 and the radicals R.sub.1 and R.sub.2 in each case jointly form a fused aromatic ring; and
- (b) at least one of the radicals R.sub.1, R.sub.2, R.sub.3, R.sub.4, and R.sub.5 represents a hydroxyl group, wherein (i) said polymeric compound and said low molecular weight compound are present in a ratio in the range of 0.1-20:1 and (ii) said ester has a diazo nitrogen content of between about 2% and about 9%; and (II) isolating the reaction product of step (I).
- 2. A process according to claim 1, wherein said naphthoquinonediazidesulfonyl halide is formed from a monosulfonic acid compound.
- 3. A process according to claim 1, wherein said naphthoquinonediazidesulfonyl halide is formed from a disulfonic acid compound.
- 4. A process according to claim 1, wherein said low molecular weight compound containing at least one phenolic hydroxyl group is selected from the group consisting of 2,4-dihydroxybenzophenone; 2,3,4-trihydroxybenzophenone; 2,4,2',4'-tetrahydroxydiphenyl sulfide; 2,2'-dihydroxydinaphthylmethane; 4,4'dihydroxy-2,2'-dimethyl-5,5-di-tert-butyldiphenyl sulfide; 4,4'-dihydroxydiphenyl sulfide; 4,6-bis-(2,4-dihydroxyphenylthio)-resorcinol; 2,3,2',4'-tetrahydroxy-3,5,5'-tetrabromodiphenyl sulfone; 2,3,2',4'-tetrahydroxy-3,5,3',5'-tetrabromobiphyenyl, and 2,4-dihydroxy-3,5-dibromobenzophenone.
- 5. A process according to claim 1, wherein said polymeric compound having recurring units comprises a phenolic resin.
- 6. A process according to claim 5, wherein said polymeric compound having recurring units comprises a resin selected from the group consisting of phenol-formaldehyde novolac resins and cresol-formaldehyde novolac resins.
- 7. A process according to claim 1, wherein the weight ratio of polymeric compound having recurring units to said low molecular weight compound lies in the range from 0.1 to 20 parts by weight of said polymeric compound per 1 part by weight of said low molecular weight compound.
- 8. A process according to claim 7, wherein the weight ratio of polymeric compound having recurring units to said low molecular weight compound lies in the range from 0.3 to 12 parts by weight of said polymeric compound per 1 part by weight of said low molecular weight compound.
- 9. A process according to claim 1, wherein the proportion of naphthoquinonediazidesulfonyl halide reacted with said reaction mixture is sufficient to completely esterify all of the phenolic hydroxyl groups of said low molecular weight compound.
- 10. A process according to claim 1, wherein said esterified reaction product has a diazo nitrogen content from about 2 to about 9 weight percent.
- 11. A process according to claim 10, wherein said esterified reaction product has a diazo nitrogen content from 3 to 8 weight percent.
- 12. A process according to claim 11, wherein said esterified reaction product has a diazo nitrogen content from 4.5 to 7.5 weight percent.
- 13. A process according to claim 1, wherein a solvent solution of said naphthoquinonediazidesulfonyl halide is added to a solvent solution of said mixture of phenolic compounds.
- 14. A process according to claim 1, wherein said reaction is effected in the presence of a base.
- 15. A process according to claim 1, wherein said low molecular weight compound contains at least two phenolic hydroxyl groups.
- 16. A process according to claim 1, wherein said naphthoquinonediazidesulfonyl halide is a 1,2-naphthoquinone-2-diazide-sulfonyl chloride.
- 17. A process according to claim 1, wherein said diazo nitrogen content is between about 3% and about 8%.
- 18. A process according to claim 17, wherein said nitrogen content is between about 4.5% and about 7%.
- 19. A process according to claim 1, wherein said reaction product is isolated by precipitation.
- 20. A process according to claim 1, wherein said reaction product is isolated by evaporating said solvent.
Priority Claims (1)
Number |
Date |
Country |
Kind |
3100077 |
Jan 1981 |
DEX |
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Parent Case Info
This is a division of application Ser. No. 333,338 filed on Dec. 22, 1981, Pat. No. 4,424,270.
US Referenced Citations (7)
Foreign Referenced Citations (2)
Number |
Date |
Country |
1113759 |
May 1968 |
GBX |
1330932 |
Sep 1973 |
GBX |
Divisions (1)
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Number |
Date |
Country |
Parent |
333338 |
Dec 1981 |
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