CA1133309A - Substances vesiculaires d'enregistrement contenant un polyelectrolyte cationique derive d'un copolymere contenant des groupements aminoacrylates et d'acide itaconique - Google Patents

Substances vesiculaires d'enregistrement contenant un polyelectrolyte cationique derive d'un copolymere contenant des groupements aminoacrylates et d'acide itaconique

Info

Publication number: CA1133309A
Authority: CA; Canada
Prior art keywords: mole; copolymer; recording material; itaconic acid; vehicle
Prior art date: 1978-09-01
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

CA316,877A

Other languages

English (en)

Inventor

John A. Pope

Stuart C. Rennison

Ronald J. Stacey

Maxwell J. Barton

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.)

Bexford Ltd

Original Assignee

Bexford Ltd

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.)

1978-09-01

Filing date

1978-11-24

Publication date

1982-10-12

1978-11-24 Application filed by Bexford Ltd filed Critical Bexford Ltd

1982-10-12 Application granted granted Critical

1982-10-12 Publication of CA1133309A publication Critical patent/CA1133309A/fr

Status Expired legal-status Critical Current

Links

239000000463 material Substances 0.000 title claims abstract description 39
LVHBHZANLOWSRM-UHFFFAOYSA-N itaconic acid Chemical group OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 title claims abstract description 15
229920000867 polyelectrolyte Polymers 0.000 title claims abstract description 13
229920001577 copolymer Polymers 0.000 title claims description 28
125000002091 cationic group Chemical group 0.000 title claims description 5
YTLYLLTVENPWFT-UPHRSURJSA-N (Z)-3-aminoacrylic acid Chemical compound N\C=C/C(O)=O YTLYLLTVENPWFT-UPHRSURJSA-N 0.000 title claims 3
JKNCOURZONDCGV-UHFFFAOYSA-N 2-(dimethylamino)ethyl 2-methylprop-2-enoate Chemical compound CN(C)CCOC(=O)C(C)=C JKNCOURZONDCGV-UHFFFAOYSA-N 0.000 claims abstract description 17
JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 claims abstract description 14
239000003795 chemical substances by application Substances 0.000 claims abstract description 14
230000001235 sensitizing effect Effects 0.000 claims abstract description 13
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 22
VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 14
239000007789 gas Substances 0.000 claims description 11
229910052757 nitrogen Inorganic materials 0.000 claims description 11
239000000203 mixture Substances 0.000 claims description 10
238000003384 imaging method Methods 0.000 claims description 5
230000035699 permeability Effects 0.000 claims description 5
238000010438 heat treatment Methods 0.000 claims description 4
238000000149 argon plasma sintering Methods 0.000 claims description 3
230000005540 biological transmission Effects 0.000 claims description 2
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 claims description 2
229910052753 mercury Inorganic materials 0.000 claims description 2
229920001169 thermoplastic Polymers 0.000 claims 4
239000004416 thermosoftening plastic Substances 0.000 claims 4
229920000642 polymer Polymers 0.000 abstract description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 8
230000035945 sensitivity Effects 0.000 abstract description 2
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
-1 polypropylene Polymers 0.000 description 19
239000011248 coating agent Substances 0.000 description 14
238000000576 coating method Methods 0.000 description 14
239000000243 solution Substances 0.000 description 14
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 11
239000002904 solvent Substances 0.000 description 7
238000000034 method Methods 0.000 description 6
229920000139 polyethylene terephthalate Polymers 0.000 description 6
239000005020 polyethylene terephthalate Substances 0.000 description 6
229920003023 plastic Polymers 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
VXIVSQZSERGHQP-UHFFFAOYSA-N chloroacetamide Chemical compound NC(=O)CCl VXIVSQZSERGHQP-UHFFFAOYSA-N 0.000 description 4
239000004033 plastic Substances 0.000 description 4
NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-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
QDHUQRBYCVAWEN-UHFFFAOYSA-N amino prop-2-enoate Chemical class NOC(=O)C=C QDHUQRBYCVAWEN-UHFFFAOYSA-N 0.000 description 3
239000000969 carrier Substances 0.000 description 3
239000012954 diazonium Substances 0.000 description 3
150000001989 diazonium salts Chemical class 0.000 description 3
150000002734 metacrylic acid derivatives Chemical class 0.000 description 3
SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-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
XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 2
BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 2
238000010521 absorption reaction Methods 0.000 description 2
125000000217 alkyl group Chemical group 0.000 description 2
150000001450 anions Chemical class 0.000 description 2
WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
238000004132 cross linking Methods 0.000 description 2
238000011161 development Methods 0.000 description 2
125000004985 dialkyl amino alkyl group Chemical group 0.000 description 2
238000001035 drying Methods 0.000 description 2
235000011194 food seasoning agent Nutrition 0.000 description 2
125000000524 functional group Chemical group 0.000 description 2
229920001519 homopolymer Polymers 0.000 description 2
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
239000011976 maleic acid Substances 0.000 description 2
BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
230000000717 retained effect Effects 0.000 description 2
238000012552 review Methods 0.000 description 2
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 1
YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 1
PXGZQGDTEZPERC-UHFFFAOYSA-N 1,4-cyclohexanedicarboxylic acid Chemical compound OC(=O)C1CCC(C(O)=O)CC1 PXGZQGDTEZPERC-UHFFFAOYSA-N 0.000 description 1
OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 1
OYUNTGBISCIYPW-UHFFFAOYSA-N 2-chloroprop-2-enenitrile Chemical compound ClC(=C)C#N OYUNTGBISCIYPW-UHFFFAOYSA-N 0.000 description 1
CFKMVGJGLGKFKI-UHFFFAOYSA-N 4-chloro-m-cresol Chemical compound CC1=CC(O)=CC=C1Cl CFKMVGJGLGKFKI-UHFFFAOYSA-N 0.000 description 1
JQVAPEJNIZULEK-UHFFFAOYSA-N 4-chlorobenzene-1,3-diol Chemical compound OC1=CC=C(Cl)C(O)=C1 JQVAPEJNIZULEK-UHFFFAOYSA-N 0.000 description 1
GTFYDURVGNMGDR-UHFFFAOYSA-N 4-n,4-n-diethylbenzene-1,4-diamine;4-n,4-n-dimethylbenzene-1,4-diamine Chemical compound CN(C)C1=CC=C(N)C=C1.CCN(CC)C1=CC=C(N)C=C1 GTFYDURVGNMGDR-UHFFFAOYSA-N 0.000 description 1
NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
241000256844 Apis mellifera Species 0.000 description 1
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 description 1
239000004952 Polyamide Substances 0.000 description 1
239000004743 Polypropylene Substances 0.000 description 1
239000004793 Polystyrene Substances 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 description 1
239000002253 acid Substances 0.000 description 1
150000003926 acrylamides Chemical class 0.000 description 1
150000001350 alkyl halides Chemical class 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
125000000129 anionic group Chemical group 0.000 description 1
239000012736 aqueous medium Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
239000004305 biphenyl Substances 0.000 description 1
235000010290 biphenyl Nutrition 0.000 description 1
KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
229920002678 cellulose Polymers 0.000 description 1
229920002301 cellulose acetate Polymers 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
239000008199 coating composition Substances 0.000 description 1
239000003431 cross linking reagent Substances 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
150000001991 dicarboxylic acids Chemical class 0.000 description 1
238000010981 drying operation Methods 0.000 description 1
239000000975 dye Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
XJELOQYISYPGDX-UHFFFAOYSA-N ethenyl 2-chloroacetate Chemical compound ClCC(=O)OC=C XJELOQYISYPGDX-UHFFFAOYSA-N 0.000 description 1
229940083124 ganglion-blocking antiadrenergic secondary and tertiary amines Drugs 0.000 description 1
150000002334 glycols Chemical class 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
230000014759 maintenance of location Effects 0.000 description 1
125000005395 methacrylic acid group Chemical class 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
239000011707 mineral Substances 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
150000002762 monocarboxylic acid derivatives Chemical class 0.000 description 1
239000000178 monomer Substances 0.000 description 1
CNXZLZNEIYFZGU-UHFFFAOYSA-N n-(4-amino-2,5-diethoxyphenyl)benzamide Chemical compound C1=C(N)C(OCC)=CC(NC(=O)C=2C=CC=CC=2)=C1OCC CNXZLZNEIYFZGU-UHFFFAOYSA-N 0.000 description 1
WPUMVKJOWWJPRK-UHFFFAOYSA-N naphthalene-2,7-dicarboxylic acid Chemical compound C1=CC(C(O)=O)=CC2=CC(C(=O)O)=CC=C21 WPUMVKJOWWJPRK-UHFFFAOYSA-N 0.000 description 1
SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
229940070805 p-chloro-m-cresol Drugs 0.000 description 1
150000002989 phenols Chemical class 0.000 description 1
ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 1
IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
229920002492 poly(sulfone) Polymers 0.000 description 1
229920002647 polyamide Polymers 0.000 description 1
239000004417 polycarbonate Substances 0.000 description 1
229920000515 polycarbonate Polymers 0.000 description 1
229920000728 polyester Polymers 0.000 description 1
229920001155 polypropylene Polymers 0.000 description 1
229920002223 polystyrene Polymers 0.000 description 1
229920000166 polytrimethylene carbonate Polymers 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
238000012545 processing Methods 0.000 description 1
230000005588 protonation Effects 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
239000001117 sulphuric acid Substances 0.000 description 1
235000011149 sulphuric acid Nutrition 0.000 description 1
230000008961 swelling Effects 0.000 description 1
230000002522 swelling effect Effects 0.000 description 1
238000012360 testing method Methods 0.000 description 1
239000012815 thermoplastic material Substances 0.000 description 1

Landscapes

Paints Or Removers (AREA)

CA316,877A 1978-09-01 1978-11-24 Substances vesiculaires d'enregistrement contenant un polyelectrolyte cationique derive d'un copolymere contenant des groupements aminoacrylates et d'acide itaconique Expired CA1133309A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GB35386/78		1978-09-01
GB7835386		1978-09-01

Publications (1)

Publication Number	Publication Date
CA1133309A true CA1133309A (fr)	1982-10-12

Family

ID=10499409

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA316,877A Expired CA1133309A (fr)	1978-09-01	1978-11-24	Substances vesiculaires d'enregistrement contenant un polyelectrolyte cationique derive d'un copolymere contenant des groupements aminoacrylates et d'acide itaconique

Country Status (1)

Country	Link
CA (1)	CA1133309A (fr)

1978
- 1978-11-24 CA CA316,877A patent/CA1133309A/fr not_active Expired

Legal Events

Date	Code	Title	Description
1999-10-12	MKEX	Expiry

Publication	Publication Date	Title
CA1206657A (fr)	1986-06-24	Methode de preparation de melanges aqueux stables a granules de polymere, et emploi desdits melanges dans des elements photographiques
US4920004A (en)	1990-04-24	Gelatin-grafted polymer particles
GB1234755A (en)	1971-06-09	Photographic film
US3513010A (en)	1970-05-19	Conversion foil
US4167414A (en)	1979-09-11	Reflective opaque polyester film base support for inverse transfer negative emulsions
US4219616A (en)	1980-08-26	Recording materials for vesicular imaging
US3075841A (en)	1963-01-29	Mordant treating process and elements containing same
US3589905A (en)	1971-06-29	Inking properties of matte-surfaced polyester sheeting
US3661589A (en)	1972-05-09	Interfacial vesicular print materials and methods of preparation
CA1133309A (fr)	1982-10-12	Substances vesiculaires d'enregistrement contenant un polyelectrolyte cationique derive d'un copolymere contenant des groupements aminoacrylates et d'acide itaconique
US3563749A (en)	1971-02-16	Light-sensitive reproduction material
CA1133308A (fr)	1982-10-12	Substances vesiculaires d'enregistrement contenant un polyelectrolyte cationique comme vehicule thermoplastique de l'agent sensibilisant
US4215191A (en)	1980-07-29	Light-sensitive vesicular recording materials and process of using
US3620743A (en)	1971-11-16	Vehicles for vesicular photographic materials
US3622335A (en)	1971-11-23	Copolymers of an alpha acrylonitrile and a styrene used as vehicles in vesicular materials
US4093463A (en)	1978-06-06	Water soluble binder overcoat on vesicular element containing N2 -releasing agent
US5223372A (en)	1993-06-29	Chemical mat film and a photosensitive film comprising an o-naphthoquinine diazide compound and a binder coated over the chemical mat film
EP0012521B1 (fr)	1983-03-23	Matériaux pour l'enregistrement vésiculaire et procédé pour leur préparation
US3647454A (en)	1972-03-07	Title-backed photosensitive microfiche
GB2095854A (en)	1982-10-06	Image forming material
US5604083A (en)	1997-02-18	Antistatic film bases and photographic elements comprising said antistatic film bases
US2755186A (en)	1956-07-17	Photographic films
US4293633A (en)	1981-10-06	Reflex copying process onto light-sensitive recording materials
CA1148404A (fr)	1983-06-21	Produit d'enregistrement renfermant un compose diazoique et une couche filtrante comprenant un polymere insoluble et un colorant thermostable
GB1565903A (en)	1980-04-23	Vesicular image recording materials