CA1062073A - Produit photosensible a base d'un compose diazo et d'un polymere greffe de type isocyanate - Google Patents

Produit photosensible a base d'un compose diazo et d'un polymere greffe de type isocyanate

Info

Publication number: CA1062073A
Authority: CA; Canada
Prior art keywords: light; isocyanate; accordance; composition; parts
Prior art date: 1975-03-27
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired

Application number

CA240,375A

Other languages

English (en)

Other versions

CA240375S (en

Inventor

Shane H. Hsieh

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

CNA Holdings LLC

Original Assignee

American Hoechst Corp

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1975-03-27

Filing date

1975-11-25

Publication date

1979-09-11

1975-03-27 Priority claimed from US05/562,662 external-priority patent/US4014655A/en

1975-11-25 Application filed by American Hoechst Corp filed Critical American Hoechst Corp

1979-09-11 Application granted granted Critical

1979-09-11 Publication of CA1062073A publication Critical patent/CA1062073A/fr

Status Expired legal-status Critical Current

Links

239000012948 isocyanate Substances 0.000 title claims abstract description 36
150000002513 isocyanates Chemical class 0.000 title claims abstract description 31
150000008049 diazo compounds Chemical group 0.000 title claims abstract description 7
239000000203 mixture Substances 0.000 title claims description 34
229920000578 graft copolymer Polymers 0.000 title description 2
238000000576 coating method Methods 0.000 claims abstract description 32
239000011248 coating agent Substances 0.000 claims abstract description 30
238000007639 printing Methods 0.000 claims abstract description 14
229920001568 phenolic resin Polymers 0.000 claims abstract description 10
239000003960 organic solvent Substances 0.000 claims abstract description 9
239000007859 condensation product Substances 0.000 claims abstract description 7
150000002148 esters Chemical class 0.000 claims abstract description 7
239000008199 coating composition Substances 0.000 claims abstract description 6
239000012670 alkaline solution Substances 0.000 claims abstract description 5
150000001408 amides Chemical class 0.000 claims abstract description 5
229920002120 photoresistant polymer Polymers 0.000 claims abstract description 4
229920005989 resin Polymers 0.000 claims description 35
239000011347 resin Substances 0.000 claims description 35
239000000243 solution Substances 0.000 claims description 28
239000000463 material Substances 0.000 claims description 22
229920003986 novolac Polymers 0.000 claims description 21
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical group [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 13
229910052782 aluminium Inorganic materials 0.000 claims description 13
238000000034 method Methods 0.000 claims description 10
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 9
239000010949 copper Substances 0.000 claims description 9
229910052802 copper Inorganic materials 0.000 claims description 9
125000005442 diisocyanate group Chemical group 0.000 claims description 6
SLGWESQGEUXWJQ-UHFFFAOYSA-N formaldehyde;phenol Chemical compound O=C.OC1=CC=CC=C1 SLGWESQGEUXWJQ-UHFFFAOYSA-N 0.000 claims description 4
239000005011 phenolic resin Substances 0.000 claims description 4
239000005056 polyisocyanate Substances 0.000 claims description 4
229920001228 polyisocyanate Polymers 0.000 claims description 4
VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 2
229910052804 chromium Inorganic materials 0.000 claims description 2
239000011651 chromium Substances 0.000 claims description 2
WOAHJDHKFWSLKE-UHFFFAOYSA-N 1,2-benzoquinone Chemical compound O=C1C=CC=CC1=O WOAHJDHKFWSLKE-UHFFFAOYSA-N 0.000 claims 3
239000000758 substrate Substances 0.000 abstract description 6
AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 abstract description 4
KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 abstract description 4
125000000524 functional group Chemical group 0.000 abstract description 4
QVEIBLDXZNGPHR-UHFFFAOYSA-N naphthalene-1,4-dione;diazide Chemical class [N-]=[N+]=[N-].[N-]=[N+]=[N-].C1=CC=C2C(=O)C=CC(=O)C2=C1 QVEIBLDXZNGPHR-UHFFFAOYSA-N 0.000 abstract description 4
239000007788 liquid Substances 0.000 abstract 1
239000002952 polymeric resin Substances 0.000 abstract 1
230000002311 subsequent effect Effects 0.000 abstract 1
229920003002 synthetic resin Polymers 0.000 abstract 1
125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 27
229920000642 polymer Polymers 0.000 description 16
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
-1 hydroxy, amino Chemical group 0.000 description 12
235000010210 aluminium Nutrition 0.000 description 11
150000001875 compounds Chemical class 0.000 description 11
XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 7
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
239000005057 Hexamethylene diisocyanate Substances 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
239000013078 crystal Substances 0.000 description 6
RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 6
239000011877 solvent mixture Substances 0.000 description 6
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 6
239000002253 acid Substances 0.000 description 5
239000007795 chemical reaction product Substances 0.000 description 5
HNHVTXYLRVGMHD-UHFFFAOYSA-N n-butyl isocyanate Chemical compound CCCCN=C=O HNHVTXYLRVGMHD-UHFFFAOYSA-N 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
QWDQYHPOSSHSAW-UHFFFAOYSA-N 1-isocyanatooctadecane Chemical compound CCCCCCCCCCCCCCCCCCN=C=O QWDQYHPOSSHSAW-UHFFFAOYSA-N 0.000 description 4
TXTIIWDWHSZBRK-UHFFFAOYSA-N 2,4-diisocyanato-1-methylbenzene;2-ethyl-2-(hydroxymethyl)propane-1,3-diol Chemical compound CCC(CO)(CO)CO.CC1=CC=C(N=C=O)C=C1N=C=O TXTIIWDWHSZBRK-UHFFFAOYSA-N 0.000 description 4
JCYPECIVGRXBMO-UHFFFAOYSA-N 4-(dimethylamino)azobenzene Chemical compound C1=CC(N(C)C)=CC=C1N=NC1=CC=CC=C1 JCYPECIVGRXBMO-UHFFFAOYSA-N 0.000 description 4
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
SJJISKLXUJVZOA-UHFFFAOYSA-N Solvent yellow 56 Chemical compound C1=CC(N(CC)CC)=CC=C1N=NC1=CC=CC=C1 SJJISKLXUJVZOA-UHFFFAOYSA-N 0.000 description 4
238000007654 immersion Methods 0.000 description 4
239000004615 ingredient Substances 0.000 description 4
238000004519 manufacturing process Methods 0.000 description 4
VZXPHDGHQXLXJC-UHFFFAOYSA-N 1,6-diisocyanato-5,6-dimethylheptane Chemical compound O=C=NC(C)(C)C(C)CCCCN=C=O VZXPHDGHQXLXJC-UHFFFAOYSA-N 0.000 description 3
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
239000007983 Tris buffer Substances 0.000 description 3
UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 3
229910000147 aluminium phosphate Inorganic materials 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
239000012975 dibutyltin dilaurate Substances 0.000 description 3
239000011888 foil Substances 0.000 description 3
230000002209 hydrophobic effect Effects 0.000 description 3
238000012986 modification Methods 0.000 description 3
230000004048 modification Effects 0.000 description 3
229960004838 phosphoric acid Drugs 0.000 description 3
235000011007 phosphoric acid Nutrition 0.000 description 3
239000000047 product Substances 0.000 description 3
230000002035 prolonged effect Effects 0.000 description 3
FMDGXCSMDZMDHZ-UHFFFAOYSA-N 1-isocyanato-4-methoxybenzene Chemical class COC1=CC=C(N=C=O)C=C1 FMDGXCSMDZMDHZ-UHFFFAOYSA-N 0.000 description 2
YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 2
229910021578 Iron(III) chloride Inorganic materials 0.000 description 2
229930192627 Naphthoquinone Natural products 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
239000004433 Thermoplastic polyurethane Substances 0.000 description 2
ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 2
238000005266 casting Methods 0.000 description 2
229920001577 copolymer Polymers 0.000 description 2
KQWGXHWJMSMDJJ-UHFFFAOYSA-N cyclohexyl isocyanate Chemical compound O=C=NC1CCCCC1 KQWGXHWJMSMDJJ-UHFFFAOYSA-N 0.000 description 2
238000011161 development Methods 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 2
150000002791 naphthoquinones Chemical class 0.000 description 2
229920005615 natural polymer Polymers 0.000 description 2
229920006267 polyester film Polymers 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
238000010992 reflux Methods 0.000 description 2
239000001488 sodium phosphate Substances 0.000 description 2
239000002904 solvent Substances 0.000 description 2
239000000126 substance Substances 0.000 description 2
229920002803 thermoplastic polyurethane Polymers 0.000 description 2
125000004149 thio group Chemical group *S* 0.000 description 2
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 2
RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 2
229910000406 trisodium phosphate Inorganic materials 0.000 description 2
235000019801 trisodium phosphate Nutrition 0.000 description 2
ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 1
229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 description 1
VGHSXKTVMPXHNG-UHFFFAOYSA-N 1,3-diisocyanatobenzene Chemical compound O=C=NC1=CC=CC(N=C=O)=C1 VGHSXKTVMPXHNG-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
BCMYXYHEMGPZJN-UHFFFAOYSA-N 1-chloro-2-isocyanatoethane Chemical compound ClCCN=C=O BCMYXYHEMGPZJN-UHFFFAOYSA-N 0.000 description 1
ADAKRBAJFHTIEW-UHFFFAOYSA-N 1-chloro-4-isocyanatobenzene Chemical class ClC1=CC=C(N=C=O)C=C1 ADAKRBAJFHTIEW-UHFFFAOYSA-N 0.000 description 1
GFNKTLQTQSALEJ-UHFFFAOYSA-N 1-isocyanato-4-nitrobenzene Chemical class [O-][N+](=O)C1=CC=C(N=C=O)C=C1 GFNKTLQTQSALEJ-UHFFFAOYSA-N 0.000 description 1
YIDSTEJLDQMWBR-UHFFFAOYSA-N 1-isocyanatododecane Chemical compound CCCCCCCCCCCCN=C=O YIDSTEJLDQMWBR-UHFFFAOYSA-N 0.000 description 1
BDQNKCYCTYYMAA-UHFFFAOYSA-N 1-isocyanatonaphthalene Chemical compound C1=CC=C2C(N=C=O)=CC=CC2=C1 BDQNKCYCTYYMAA-UHFFFAOYSA-N 0.000 description 1
DYQFCTCUULUMTQ-UHFFFAOYSA-N 1-isocyanatooctane Chemical compound CCCCCCCCN=C=O DYQFCTCUULUMTQ-UHFFFAOYSA-N 0.000 description 1
KUBDPQJOLOUJRM-UHFFFAOYSA-N 2-(chloromethyl)oxirane;4-[2-(4-hydroxyphenyl)propan-2-yl]phenol Chemical compound ClCC1CO1.C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 KUBDPQJOLOUJRM-UHFFFAOYSA-N 0.000 description 1
MGOLNIXAPIAKFM-UHFFFAOYSA-N 2-isocyanato-2-methylpropane Chemical compound CC(C)(C)N=C=O MGOLNIXAPIAKFM-UHFFFAOYSA-N 0.000 description 1
PYSRRFNXTXNWCD-UHFFFAOYSA-N 3-(2-phenylethenyl)furan-2,5-dione Chemical compound O=C1OC(=O)C(C=CC=2C=CC=CC=2)=C1 PYSRRFNXTXNWCD-UHFFFAOYSA-N 0.000 description 1
UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 1
WTQZSMDDRMKJRI-UHFFFAOYSA-N 4-diazoniophenolate Chemical class [O-]C1=CC=C([N+]#N)C=C1 WTQZSMDDRMKJRI-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
229920000178 Acrylic resin Polymers 0.000 description 1
239000004925 Acrylic resin Substances 0.000 description 1
208000023514 Barrett esophagus Diseases 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
239000004698 Polyethylene Substances 0.000 description 1
229920001800 Shellac Polymers 0.000 description 1
229920000147 Styrene maleic anhydride Polymers 0.000 description 1
RCTGMCJBQGBLKT-UHFFFAOYSA-N Sudan IV Chemical compound CC1=CC=CC=C1N=NC(C=C1C)=CC=C1N=NC1=C(O)C=CC2=CC=CC=C12 RCTGMCJBQGBLKT-UHFFFAOYSA-N 0.000 description 1
XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
AMPCGOAFZFKBGH-UHFFFAOYSA-O [4-[[4-(dimethylamino)phenyl]-[4-(methylamino)phenyl]methylidene]cyclohexa-2,5-dien-1-ylidene]-dimethylazanium Chemical compound C1=CC(NC)=CC=C1C(C=1C=CC(=CC=1)N(C)C)=C1C=CC(=[N+](C)C)C=C1 AMPCGOAFZFKBGH-UHFFFAOYSA-O 0.000 description 1
238000005299 abrasion Methods 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
239000003513 alkali Substances 0.000 description 1
WLDHEUZGFKACJH-UHFFFAOYSA-K amaranth Chemical compound [Na+].[Na+].[Na+].C12=CC=C(S([O-])(=O)=O)C=C2C=C(S([O-])(=O)=O)C(O)=C1N=NC1=CC=C(S([O-])(=O)=O)C2=CC=CC=C12 WLDHEUZGFKACJH-UHFFFAOYSA-K 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
239000002585 base Substances 0.000 description 1
230000001680 brushing effect Effects 0.000 description 1
239000000969 carrier Substances 0.000 description 1
239000004359 castor oil Substances 0.000 description 1
235000019438 castor oil Nutrition 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
229940000425 combination drug Drugs 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 1
ZXJXZNDDNMQXFV-UHFFFAOYSA-M crystal violet Chemical compound [Cl-].C1=CC(N(C)C)=CC=C1[C+](C=1C=CC(=CC=1)N(C)C)C1=CC=C(N(C)C)C=C1 ZXJXZNDDNMQXFV-UHFFFAOYSA-M 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
AYOHIQLKSOJJQH-UHFFFAOYSA-N dibutyltin Chemical compound CCCC[Sn]CCCC AYOHIQLKSOJJQH-UHFFFAOYSA-N 0.000 description 1
238000001035 drying Methods 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000001914 filtration Methods 0.000 description 1
DYDNPESBYVVLBO-UHFFFAOYSA-N formanilide Chemical compound O=CNC1=CC=CC=C1 DYDNPESBYVVLBO-UHFFFAOYSA-N 0.000 description 1
235000013350 formula milk Nutrition 0.000 description 1
238000009472 formulation Methods 0.000 description 1
ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
LNCPIMCVTKXXOY-UHFFFAOYSA-N hexyl 2-methylprop-2-enoate Chemical compound CCCCCCOC(=O)C(C)=C LNCPIMCVTKXXOY-UHFFFAOYSA-N 0.000 description 1
ANJPRQPHZGHVQB-UHFFFAOYSA-N hexyl isocyanate Chemical compound CCCCCCN=C=O ANJPRQPHZGHVQB-UHFFFAOYSA-N 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
238000010348 incorporation Methods 0.000 description 1
238000002329 infrared spectrum Methods 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
239000010410 layer Substances 0.000 description 1
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238000002844 melting Methods 0.000 description 1
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WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
GEMHFKXPOCTAIP-UHFFFAOYSA-N n,n-dimethyl-n'-phenylcarbamimidoyl chloride Chemical compound CN(C)C(Cl)=NC1=CC=CC=C1 GEMHFKXPOCTAIP-UHFFFAOYSA-N 0.000 description 1
238000007645 offset printing Methods 0.000 description 1
239000003921 oil Substances 0.000 description 1
239000000123 paper Substances 0.000 description 1
DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 1
235000021317 phosphate Nutrition 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
239000004033 plastic Substances 0.000 description 1
229920003023 plastic Polymers 0.000 description 1
238000007747 plating Methods 0.000 description 1
238000006068 polycondensation reaction Methods 0.000 description 1
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229920000573 polyethylene Polymers 0.000 description 1
229920000151 polyglycol Polymers 0.000 description 1
239000010695 polyglycol Substances 0.000 description 1
239000013047 polymeric layer Substances 0.000 description 1
229920002689 polyvinyl acetate Polymers 0.000 description 1
239000011118 polyvinyl acetate Substances 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
239000012260 resinous material Substances 0.000 description 1
238000012552 review Methods 0.000 description 1
PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical compound [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 description 1
238000007761 roller coating Methods 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
239000004208 shellac Substances 0.000 description 1
229940113147 shellac Drugs 0.000 description 1
235000013874 shellac Nutrition 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
229920001897 terpolymer Polymers 0.000 description 1
LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
230000003313 weakening effect Effects 0.000 description 1
239000011701 zinc Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
235000005074 zinc chloride Nutrition 0.000 description 1
JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical class [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 1

Landscapes

Photosensitive Polymer And Photoresist Processing (AREA)

CA240,375A 1975-03-27 1975-11-25 Produit photosensible a base d'un compose diazo et d'un polymere greffe de type isocyanate Expired CA1062073A (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US05/562,662 US4014655A (en)	1974-04-10	1975-03-27	Plant for continuous production of explosive containing explosive oil

Publications (1)

Publication Number	Publication Date
CA1062073A true CA1062073A (fr)	1979-09-11

Family

ID=24247225

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA240,375A Expired CA1062073A (fr)	1975-03-27	1975-11-25	Produit photosensible a base d'un compose diazo et d'un polymere greffe de type isocyanate

Country Status (1)

Country	Link
CA (1)	CA1062073A (fr)

1975
- 1975-11-25 CA CA240,375A patent/CA1062073A/fr not_active Expired

Publication	Publication Date	Title
US4189320A (en)	1980-02-19	Light-sensitive o-quinone diazide compositions and photographic reproduction processes and structures
US4316949A (en)	1982-02-23	Photoreactive oligomer composition and printing plate
DE3812278C2 (de)	1995-10-05	Lichtempfindliches Gemisch
US4898803A (en)	1990-02-06	Light-sensitive o-quinone diazide composition with acidic polyurethane resin
US4983491A (en)	1991-01-08	Photosensitive diazo resin composition with polyurethane resin having carboxyl group in its main chain
CA1282627C (fr)	1991-04-09	Resine photosensible negative pour la solarisation
US4408532A (en)	1983-10-11	Lithographic printing plate with oleophilic area of radiation exposed adduct of diazo resin and sulfonated polymer
US4337307A (en)	1982-06-29	Light-sensitive diazo composition and material with branched polyurethane resin
CA2045917C (fr)	1995-04-11	Resine photosensible positive
US4931381A (en)	1990-06-05	Image reversal negative working O-quinone diazide and cross-linking compound containing photoresist process with thermal curing treatment
US4839254A (en)	1989-06-13	Photosensitive mixture and photosensitive recording material produced therefrom with polymeric binder which is reaction product of (thio) phosphinic acidiso (thio) cyanate and active hydrogen containing polymer
US4618562A (en)	1986-10-21	Aqueous developable lithographic printing plates containing an admixture of diazonium salts and polymers and composition therefor
US5091287A (en)	1992-02-25	Photoreactive oligomer composition and printing plate
JP2584672B2 (ja)	1997-02-26	感光性組成物
US5340685A (en)	1994-08-23	Light-sensitive composition containing diazo resin, polyurethane resin and fluorine atom-containing copolymer surfactant
US4401743A (en)	1983-08-30	Aqueous developable photosensitive composition and printing plate
EP0651893B1 (fr)	1999-01-20	Diazonaphthoquinone sulfonates d'hexahydroxybenzophenone et resines photosensibles positives utilisant ces derniers comme sensibilisateurs
JPH0425842A (ja)	1992-01-29	感光性組成物
CA1062073A (fr)	1979-09-11	Produit photosensible a base d'un compose diazo et d'un polymere greffe de type isocyanate
EP0040470A2 (fr)	1981-11-25	Composition photosensible développable à l'eau et plaque d'impression
JP2584671B2 (ja)	1997-02-26	感光性組成物
DE2617088A1 (de)	1976-11-11	Lichtempfindliche kopiermasse
EP0326714B1 (fr)	1994-01-19	Condensats diazonium photosensibles en trois dimensions
EP0671660A2 (fr)	1995-09-13	Matériau servant à la réalisation de cadres de connexion
WO1993006528A1 (fr)	1993-04-01	Compositions pour couches produisant une image positive