CA1064309A - Diazotype a deux composants avec couche exterieure de resine - Google Patents

Diazotype a deux composants avec couche exterieure de resine

Info

Publication number: CA1064309A
Authority: CA; Canada
Prior art keywords: diazotype; resin; material according; diazotype material; base
Prior art date: 1974-11-18
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

CA233,293A

Other languages

English (en)

Other versions

CA233293S (en

Inventor

Andrew M. Barba

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.)

GAF Corp

Original Assignee

GAF 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.)

1974-11-18

Filing date

1975-08-12

Publication date

1979-10-16

1975-08-12 Application filed by GAF Corp filed Critical GAF Corp

1979-10-16 Application granted granted Critical

1979-10-16 Publication of CA1064309A publication Critical patent/CA1064309A/fr

Status Expired legal-status Critical Current

Links

229920005989 resin Polymers 0.000 title claims abstract description 30
239000011347 resin Substances 0.000 title claims abstract description 30
239000000463 material Substances 0.000 claims abstract description 64
230000001235 sensitizing effect Effects 0.000 claims abstract description 23
239000000203 mixture Substances 0.000 claims abstract description 15
229920003180 amino resin Polymers 0.000 claims abstract description 9
239000003822 epoxy resin Substances 0.000 claims abstract description 9
229920000647 polyepoxide Polymers 0.000 claims abstract description 9
238000000576 coating method Methods 0.000 claims description 14
239000011248 coating agent Substances 0.000 claims description 13
125000000664 diazo group Chemical class [N-]=[N+]=[*] 0.000 claims description 13
239000004922 lacquer Substances 0.000 claims description 11
229920001807 Urea-formaldehyde Polymers 0.000 claims description 8
229920002301 cellulose acetate Polymers 0.000 claims description 8
229920000728 polyester Polymers 0.000 claims description 8
150000001299 aldehydes Chemical class 0.000 claims description 7
150000008049 diazo compounds Chemical class 0.000 claims description 7
239000004372 Polyvinyl alcohol Substances 0.000 claims description 6
-1 amino compound Chemical class 0.000 claims description 6
ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 claims description 6
229920002451 polyvinyl alcohol Polymers 0.000 claims description 6
235000019422 polyvinyl alcohol Nutrition 0.000 claims description 6
238000006149 azo coupling reaction Methods 0.000 claims description 5
IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 claims description 5
NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 claims description 4
125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 claims description 4
239000007795 chemical reaction product Substances 0.000 claims description 4
229920003023 plastic Polymers 0.000 claims description 4
239000004033 plastic Substances 0.000 claims description 4
238000010424 printmaking Methods 0.000 claims description 4
GZCGUPFRVQAUEE-SLPGGIOYSA-N aldehydo-D-glucose Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O GZCGUPFRVQAUEE-SLPGGIOYSA-N 0.000 claims description 3
229920000642 polymer Polymers 0.000 claims description 3
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
229920001187 thermosetting polymer Polymers 0.000 claims description 3
239000004634 thermosetting polymer Substances 0.000 claims description 3
229920000877 Melamine resin Polymers 0.000 claims description 2
IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 claims description 2
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 2
WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 claims description 2
HGBOYTHUEUWSSQ-UHFFFAOYSA-N valeric aldehyde Natural products CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 claims description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 2
231100000202 sensitizing Toxicity 0.000 abstract description 17
LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 abstract description 4
239000000654 additive Substances 0.000 description 7
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
150000001875 compounds Chemical class 0.000 description 6
239000007787 solid Substances 0.000 description 6
238000000034 method Methods 0.000 description 5
ODGAOXROABLFNM-UHFFFAOYSA-N polynoxylin Chemical compound O=C.NC(N)=O ODGAOXROABLFNM-UHFFFAOYSA-N 0.000 description 5
239000004593 Epoxy Substances 0.000 description 4
230000000996 additive effect Effects 0.000 description 4
JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
239000008199 coating composition Substances 0.000 description 3
230000008878 coupling Effects 0.000 description 3
238000010168 coupling process Methods 0.000 description 3
238000005859 coupling reaction Methods 0.000 description 3
150000001989 diazonium salts Chemical class 0.000 description 3
239000003960 organic solvent Substances 0.000 description 3
239000003381 stabilizer Substances 0.000 description 3
YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
OJGMBLNIHDZDGS-UHFFFAOYSA-N N-Ethylaniline Chemical compound CCNC1=CC=CC=C1 OJGMBLNIHDZDGS-UHFFFAOYSA-N 0.000 description 2
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
YKYOUMDCQGMQQO-UHFFFAOYSA-L cadmium dichloride Chemical compound Cl[Cd]Cl YKYOUMDCQGMQQO-UHFFFAOYSA-L 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
239000012954 diazonium Substances 0.000 description 2
229910001873 dinitrogen Inorganic materials 0.000 description 2
229920003986 novolac Polymers 0.000 description 2
230000008569 process Effects 0.000 description 2
GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
239000008096 xylene Substances 0.000 description 2
239000011592 zinc chloride Substances 0.000 description 2
235000005074 zinc chloride Nutrition 0.000 description 2
NJLLALPCADBTIS-UHFFFAOYSA-N 2,5-dibutoxy-4-morpholin-4-ylbenzenediazonium Chemical compound C1=C([N+]#N)C(OCCCC)=CC(N2CCOCC2)=C1OCCCC NJLLALPCADBTIS-UHFFFAOYSA-N 0.000 description 1
WFXLRLQSHRNHCE-UHFFFAOYSA-N 2-(4-amino-n-ethylanilino)ethanol Chemical compound OCCN(CC)C1=CC=C(N)C=C1 WFXLRLQSHRNHCE-UHFFFAOYSA-N 0.000 description 1
XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
WXHLLJAMBQLULT-UHFFFAOYSA-N 2-[[6-[4-(2-hydroxyethyl)piperazin-1-yl]-2-methylpyrimidin-4-yl]amino]-n-(2-methyl-6-sulfanylphenyl)-1,3-thiazole-5-carboxamide;hydrate Chemical compound O.C=1C(N2CCN(CCO)CC2)=NC(C)=NC=1NC(S1)=NC=C1C(=O)NC1=C(C)C=CC=C1S WXHLLJAMBQLULT-UHFFFAOYSA-N 0.000 description 1
ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
RGCITEKHKXPDDH-UHFFFAOYSA-N 4-(diethylamino)benzenediazonium Chemical compound CCN(CC)C1=CC=C([N+]#N)C=C1 RGCITEKHKXPDDH-UHFFFAOYSA-N 0.000 description 1
PHNDZBFLOPIMSM-UHFFFAOYSA-N 4-morpholin-4-ylaniline Chemical compound C1=CC(N)=CC=C1N1CCOCC1 PHNDZBFLOPIMSM-UHFFFAOYSA-N 0.000 description 1
QNGVNLMMEQUVQK-UHFFFAOYSA-N 4-n,4-n-diethylbenzene-1,4-diamine Chemical compound CCN(CC)C1=CC=C(N)C=C1 QNGVNLMMEQUVQK-UHFFFAOYSA-N 0.000 description 1
GZVHEAJQGPRDLQ-UHFFFAOYSA-N 6-phenyl-1,3,5-triazine-2,4-diamine Chemical compound NC1=NC(N)=NC(C=2C=CC=CC=2)=N1 GZVHEAJQGPRDLQ-UHFFFAOYSA-N 0.000 description 1
229920002799 BoPET Polymers 0.000 description 1
229920008347 Cellulose acetate propionate Polymers 0.000 description 1
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
239000005041 Mylar™ Substances 0.000 description 1
239000004698 Polyethylene Substances 0.000 description 1
239000004793 Polystyrene Substances 0.000 description 1
229920001756 Polyvinyl chloride acetate Polymers 0.000 description 1
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
UGZICOVULPINFH-UHFFFAOYSA-N acetic acid;butanoic acid Chemical compound CC(O)=O.CCCC(O)=O UGZICOVULPINFH-UHFFFAOYSA-N 0.000 description 1
239000002253 acid Substances 0.000 description 1
150000008043 acidic salts Chemical class 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
230000004888 barrier function Effects 0.000 description 1
229920000402 bisphenol A polycarbonate polymer Polymers 0.000 description 1
KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
239000004327 boric acid Substances 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
229920006217 cellulose acetate butyrate Polymers 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
229930003836 cresol Natural products 0.000 description 1
230000002939 deleterious effect Effects 0.000 description 1
238000006193 diazotization reaction Methods 0.000 description 1
GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 1
GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical class C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 1
230000000694 effects Effects 0.000 description 1
238000005516 engineering process Methods 0.000 description 1
YAMHXTCMCPHKLN-UHFFFAOYSA-N imidazolidin-2-one Chemical compound O=C1NCCN1 YAMHXTCMCPHKLN-UHFFFAOYSA-N 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
239000007788 liquid Substances 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
229910001629 magnesium chloride Inorganic materials 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
230000007246 mechanism Effects 0.000 description 1
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
229910052753 mercury Inorganic materials 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
239000003607 modifier Substances 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
239000002985 plastic film Substances 0.000 description 1
229920006255 plastic film Polymers 0.000 description 1
229920000515 polycarbonate Polymers 0.000 description 1
239000004417 polycarbonate Substances 0.000 description 1
229920000573 polyethylene Polymers 0.000 description 1
229920006324 polyoxymethylene Polymers 0.000 description 1
229920002223 polystyrene Polymers 0.000 description 1
239000011118 polyvinyl acetate Substances 0.000 description 1
229920002689 polyvinyl acetate Polymers 0.000 description 1
239000004800 polyvinyl chloride Substances 0.000 description 1
230000002028 premature Effects 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
239000000047 product Substances 0.000 description 1
230000005855 radiation Effects 0.000 description 1
230000009467 reduction Effects 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
238000000926 separation method Methods 0.000 description 1
229910052709 silver Inorganic materials 0.000 description 1
239000004332 silver Substances 0.000 description 1
238000003860 storage Methods 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
229920001169 thermoplastic Polymers 0.000 description 1

Classifications

- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
- G03C1/00—Photosensitive materials
- G03C1/52—Compositions containing diazo compounds as photosensitive substances
- G03C1/60—Compositions containing diazo compounds as photosensitive substances with macromolecular additives

Landscapes

Physics & Mathematics (AREA)
Spectroscopy & Molecular Physics (AREA)
Chemical & Material Sciences (AREA)
Engineering & Computer Science (AREA)
Materials Engineering (AREA)
General Physics & Mathematics (AREA)
Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
Photosensitive Polymer And Photoresist Processing (AREA)

CA233,293A 1974-11-18 1975-08-12 Diazotype a deux composants avec couche exterieure de resine Expired CA1064309A (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US52492374A	1974-11-18	1974-11-18

Publications (1)

Publication Number	Publication Date
CA1064309A true CA1064309A (fr)	1979-10-16

Family

ID=24091200

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA233,293A Expired CA1064309A (fr)	1974-11-18	1975-08-12	Diazotype a deux composants avec couche exterieure de resine

Country Status (8)

Country	Link
JP (1)	JPS5168223A (fr)
BE (1)	BE835645A (fr)
CA (1)	CA1064309A (fr)
CH (1)	CH613786A5 (fr)
DE (1)	DE2541469A1 (fr)
FR (1)	FR2291526A1 (fr)
GB (1)	GB1526812A (fr)
NL (1)	NL7513438A (fr)

1975
- 1975-08-12 CA CA233,293A patent/CA1064309A/fr not_active Expired
- 1975-09-09 GB GB3708775A patent/GB1526812A/en not_active Expired
- 1975-09-17 DE DE19752541469 patent/DE2541469A1/de not_active Withdrawn
- 1975-10-06 CH CH1296975A patent/CH613786A5/xx not_active IP Right Cessation
- 1975-10-24 JP JP12827175A patent/JPS5168223A/ja active Pending
- 1975-11-14 FR FR7534809A patent/FR2291526A1/fr not_active Withdrawn
- 1975-11-17 BE BE161931A patent/BE835645A/fr unknown
- 1975-11-18 NL NL7513438A patent/NL7513438A/xx not_active Application Discontinuation

Also Published As

Publication number	Publication date
CH613786A5 (en)	1979-10-15
NL7513438A (nl)	1976-05-20
GB1526812A (en)	1978-10-04
FR2291526A1 (fr)	1976-06-11
JPS5168223A (ja)	1976-06-12
BE835645A (fr)	1976-05-17
DE2541469A1 (de)	1976-05-20

Publication	Publication Date	Title
US2501874A (en)	1950-03-28	Photographic diazo-sensitized glassine paper
US3102811A (en)	1963-09-03	Process for producing images, using light sensitive aromatic 1,2-dialdehydes and elements therefor
US3224878A (en)	1965-12-21	Thermographic diazotype reproduction material, method of making and method of using
CA1064309A (fr)	1979-10-16	Diazotype a deux composants avec couche exterieure de resine
US3661591A (en)	1972-05-09	Diazotype materials
EP0080241B1 (fr)	1987-09-09	Matériau diazotype
EP0002323B1 (fr)	1981-10-07	Matériaux d'enregistrement vésiculaire
US2873207A (en)	1959-02-10	Diazotype reproduction material and method
US4403028A (en)	1983-09-06	Light sensitive diazonium salts and diazotype materials
US2536989A (en)	1951-01-02	Diazotype layers containing resorcinol derivatives
US4131468A (en)	1978-12-26	Diazotype materials
US4152156A (en)	1979-05-01	Duplication-proof photographic film
US4088492A (en)	1978-05-09	Diazotype materials with hydroxypropyl cellulose ether as anti-slip material
US3754916A (en)	1973-08-28	Heat developable diazo type sheets
US3679413A (en)	1972-07-25	Photographic process which produces neutral dye image in diazotype material
US2162456A (en)	1939-06-13	Photographic printing material
US3836369A (en)	1974-09-17	Diazo photosensitive composition
US2542566A (en)	1951-02-20	2, 2', 4, 4'-tetrahydroxybiphenyl coupling component for diazotype layers
US3113865A (en)	1963-12-10	Heat developable diazo sulfones
US3915709A (en)	1975-10-28	Backwetting coating for diazo microfilm
US3191030A (en)	1965-06-22	Process of making and using thermographic reproduction paper
US4108664A (en)	1978-08-22	Light-sensitive negative-working film containing a diazo oxide sensitizer and a p-toluenesulfonyl halide or a 2,4-dihalo-S-triazine
US2437868A (en)	1948-03-16	Diazotype layers containing resorcinol monoesters
US3485631A (en)	1969-12-23	Vesicular photographic materials
US3694247A (en)	1972-09-26	Heat-sensitive copying material