CA1123997A - Lithographic ink vehicle containing addition polymers and aliphatic hydrocarbon solvent - Google Patents

Lithographic ink vehicle containing addition polymers and aliphatic hydrocarbon solvent

Info

Publication number: CA1123997A
Authority: CA; Canada
Prior art keywords: polymer; methacrylate; ink; solvent; copolymer
Prior art date: 1977-02-07
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

CA295,526A

Other languages

English (en)

French (fr)

Inventor

Graham Swift

Harry J. Cenci

Raymond F. Jenkins

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.)

Rohm and Haas Co

Original Assignee

Rohm and Haas Co

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.)

1977-02-07

Filing date

1978-01-24

Publication date

1982-05-18

1978-01-24 Application filed by Rohm and Haas Co filed Critical Rohm and Haas Co

1982-05-18 Application granted granted Critical

1982-05-18 Publication of CA1123997A publication Critical patent/CA1123997A/en

Status Expired legal-status Critical Current

Links

229920000642 polymer Polymers 0.000 title claims abstract description 56
239000002904 solvent Substances 0.000 title claims abstract description 24
150000001338 aliphatic hydrocarbons Chemical class 0.000 title claims abstract description 7
239000000178 monomer Substances 0.000 claims abstract description 30
229920001577 copolymer Polymers 0.000 claims abstract description 24
229940119545 isobornyl methacrylate Drugs 0.000 claims abstract description 18
IAXXETNIOYFMLW-COPLHBTASA-N [(1s,3s,4s)-4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl] 2-methylprop-2-enoate Chemical compound C1C[C@]2(C)[C@@H](OC(=O)C(=C)C)C[C@H]1C2(C)C IAXXETNIOYFMLW-COPLHBTASA-N 0.000 claims abstract description 16
RUMACXVDVNRZJZ-UHFFFAOYSA-N 2-methylpropyl 2-methylprop-2-enoate Chemical compound CC(C)COC(=O)C(C)=C RUMACXVDVNRZJZ-UHFFFAOYSA-N 0.000 claims abstract description 10
239000002253 acid Substances 0.000 claims abstract description 4
CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims description 13
239000000049 pigment Substances 0.000 claims description 12
238000000034 method Methods 0.000 claims description 11
NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 10
239000011230 binding agent Substances 0.000 claims description 10
239000004215 Carbon black (E152) Substances 0.000 claims description 9
229930195733 hydrocarbon Natural products 0.000 claims description 9
150000002430 hydrocarbons Chemical class 0.000 claims description 9
CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 6
239000000758 substrate Substances 0.000 claims description 6
SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 5
239000000203 mixture Substances 0.000 claims description 5
JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 claims description 4
NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 4
LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 claims description 4
229920002554 vinyl polymer Polymers 0.000 claims description 4
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 description 3
BEWCNXNIQCLWHP-UHFFFAOYSA-N 2-(tert-butylamino)ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCNC(C)(C)C BEWCNXNIQCLWHP-UHFFFAOYSA-N 0.000 claims description 3
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 3
AQNSVANSEBPSMK-UHFFFAOYSA-N dicyclopentenyl methacrylate Chemical compound C12CC=CC2C2CC(OC(=O)C(=C)C)C1C2.C12C=CCC2C2CC(OC(=O)C(=C)C)C1C2 AQNSVANSEBPSMK-UHFFFAOYSA-N 0.000 claims description 3
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 3
PSGCQDPCAWOCSH-UHFFFAOYSA-N (4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl) prop-2-enoate Chemical compound C1CC2(C)C(OC(=O)C=C)CC1C2(C)C PSGCQDPCAWOCSH-UHFFFAOYSA-N 0.000 claims description 2
229930195734 saturated hydrocarbon Natural products 0.000 claims description 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
FGERRMPOTZKDOB-UHFFFAOYSA-N 2-(1,3-oxazolidin-3-yl)ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCN1CCOC1 FGERRMPOTZKDOB-UHFFFAOYSA-N 0.000 claims 1
229940026213 2-(3-oxazolidinyl)ethyl methacrylate Drugs 0.000 claims 1
LUCXVPAZUDVVBT-UHFFFAOYSA-N methyl-[3-(2-methylphenoxy)-3-phenylpropyl]azanium;chloride Chemical compound Cl.C=1C=CC=CC=1C(CCNC)OC1=CC=CC=C1C LUCXVPAZUDVVBT-UHFFFAOYSA-N 0.000 claims 1
230000007704 transition Effects 0.000 abstract description 3
125000003277 amino group Chemical group 0.000 abstract 1
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 13
239000007787 solid Substances 0.000 description 12
239000000976 ink Substances 0.000 description 11
-1 2-ethylhexyl Chemical group 0.000 description 7
238000009835 boiling Methods 0.000 description 7
239000011572 manganese Substances 0.000 description 7
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 5
239000011347 resin Substances 0.000 description 5
229920005989 resin Polymers 0.000 description 5
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
229920001519 homopolymer Polymers 0.000 description 4
238000006116 polymerization reaction Methods 0.000 description 4
239000008096 xylene Substances 0.000 description 4
239000006229 carbon black Substances 0.000 description 3
DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical group C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 description 2
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
241000016649 Copaifera officinalis Species 0.000 description 2
239000004868 Kauri gum Substances 0.000 description 2
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
239000000654 additive Substances 0.000 description 2
125000001931 aliphatic group Chemical group 0.000 description 2
150000001336 alkenes Chemical class 0.000 description 2
229920000180 alkyd Polymers 0.000 description 2
XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 2
238000004821 distillation Methods 0.000 description 2
230000009477 glass transition Effects 0.000 description 2
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 2
239000000463 material Substances 0.000 description 2
150000002734 metacrylic acid derivatives Chemical class 0.000 description 2
229910052751 metal Inorganic materials 0.000 description 2
239000002184 metal Substances 0.000 description 2
229920003229 poly(methyl methacrylate) Polymers 0.000 description 2
229920000058 polyacrylate Polymers 0.000 description 2
229920000915 polyvinyl chloride Polymers 0.000 description 2
239000004800 polyvinyl chloride Substances 0.000 description 2
HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 2
GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 description 2
ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 2
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
150000003738 xylenes Chemical class 0.000 description 2
DTGKSKDOIYIVQL-MRTMQBJTSA-N (-)-isoborneol Chemical compound C1C[C@@]2(C)[C@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-MRTMQBJTSA-N 0.000 description 1
JHPBZFOKBAGZBL-UHFFFAOYSA-N (3-hydroxy-2,2,4-trimethylpentyl) 2-methylprop-2-enoate Chemical compound CC(C)C(O)C(C)(C)COC(=O)C(C)=C JHPBZFOKBAGZBL-UHFFFAOYSA-N 0.000 description 1
NAQCKZRDENMSDA-UHFFFAOYSA-N 1,3-oxazolidin-2-yl prop-2-enoate Chemical class C=CC(=O)OC1NCCO1 NAQCKZRDENMSDA-UHFFFAOYSA-N 0.000 description 1
PQDKOKTULASSPO-UHFFFAOYSA-N 2-(1,3-oxazolidin-2-yl)ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCC1NCCO1 PQDKOKTULASSPO-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
MFYSUUPKMDJYPF-UHFFFAOYSA-N 2-[(4-methyl-2-nitrophenyl)diazenyl]-3-oxo-n-phenylbutanamide Chemical compound C=1C=CC=CC=1NC(=O)C(C(=O)C)N=NC1=CC=C(C)C=C1[N+]([O-])=O MFYSUUPKMDJYPF-UHFFFAOYSA-N 0.000 description 1
FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 1
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 1
241001269524 Dura Species 0.000 description 1
LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 1
239000000020 Nitrocellulose Substances 0.000 description 1
239000004952 Polyamide Substances 0.000 description 1
229920001800 Shellac Polymers 0.000 description 1
238000005299 abrasion Methods 0.000 description 1
229920006243 acrylic copolymer Polymers 0.000 description 1
229920006397 acrylic thermoplastic Polymers 0.000 description 1
239000008186 active pharmaceutical agent Substances 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
IRERQBUNZFJFGC-UHFFFAOYSA-L azure blue Chemical compound [Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Al+3].[Al+3].[Al+3].[Al+3].[Al+3].[Al+3].[S-]S[S-].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-] IRERQBUNZFJFGC-UHFFFAOYSA-L 0.000 description 1
SMDHCQAYESWHAE-UHFFFAOYSA-N benfluralin Chemical compound CCCCN(CC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O SMDHCQAYESWHAE-UHFFFAOYSA-N 0.000 description 1
230000000903 blocking effect Effects 0.000 description 1
244000309464 bull Species 0.000 description 1
CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
229920002678 cellulose Polymers 0.000 description 1
238000012512 characterization method Methods 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
229910017052 cobalt Inorganic materials 0.000 description 1
239000010941 cobalt Substances 0.000 description 1
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
DTGKSKDOIYIVQL-UHFFFAOYSA-N dl-isoborneol Natural products C1CC2(C)C(O)CC1C2(C)C DTGKSKDOIYIVQL-UHFFFAOYSA-N 0.000 description 1
WNAHIZMDSQCWRP-UHFFFAOYSA-N dodecane-1-thiol Chemical compound CCCCCCCCCCCCS WNAHIZMDSQCWRP-UHFFFAOYSA-N 0.000 description 1
238000001035 drying Methods 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 description 1
JEIPFZHSYJVQDO-UHFFFAOYSA-N ferric oxide Chemical compound O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
238000011010 flushing procedure Methods 0.000 description 1
238000009472 formulation Methods 0.000 description 1
238000005227 gel permeation chromatography Methods 0.000 description 1
239000011521 glass Substances 0.000 description 1
230000005484 gravity Effects 0.000 description 1
239000003999 initiator Substances 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
239000007788 liquid Substances 0.000 description 1
JYNBEDVXQNFTOX-FMQUCBEESA-N lithol rubine Chemical compound OS(=O)(=O)C1=CC(C)=CC=C1\N=N\C1=C(O)C(C(O)=O)=CC2=CC=CC=C12 JYNBEDVXQNFTOX-FMQUCBEESA-N 0.000 description 1
235000010187 litholrubine BK Nutrition 0.000 description 1
SGGOJYZMTYGPCH-UHFFFAOYSA-L manganese(2+);naphthalene-2-carboxylate Chemical compound [Mn+2].C1=CC=CC2=CC(C(=O)[O-])=CC=C21.C1=CC=CC2=CC(C(=O)[O-])=CC=C21 SGGOJYZMTYGPCH-UHFFFAOYSA-L 0.000 description 1
238000005259 measurement Methods 0.000 description 1
229920001220 nitrocellulos Polymers 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
125000000160 oxazolidinyl group Chemical group 0.000 description 1
239000013618 particulate matter Substances 0.000 description 1
229920002647 polyamide Polymers 0.000 description 1
239000002685 polymerization catalyst Substances 0.000 description 1
239000003505 polymerization initiator Substances 0.000 description 1
239000004926 polymethyl methacrylate Substances 0.000 description 1
229920000056 polyoxyethylene ether Polymers 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
239000001054 red pigment Substances 0.000 description 1
IOVGROKTTNBUGK-SJCJKPOMSA-N ritodrine Chemical compound N([C@@H](C)[C@H](O)C=1C=CC(O)=CC=1)CCC1=CC=C(O)C=C1 IOVGROKTTNBUGK-SJCJKPOMSA-N 0.000 description 1
229920006395 saturated elastomer Polymers 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
239000004408 titanium dioxide Substances 0.000 description 1
238000005809 transesterification reaction Methods 0.000 description 1
235000013799 ultramarine blue Nutrition 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/02—Printing inks
- C09D11/10—Printing inks based on artificial resins
- C09D11/106—Printing inks based on artificial resins containing macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- C09D11/107—Printing inks based on artificial resins containing macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds from unsaturated acids or derivatives thereof

Landscapes

Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Life Sciences & Earth Sciences (AREA)
Engineering & Computer Science (AREA)
Materials Engineering (AREA)
Wood Science & Technology (AREA)
Organic Chemistry (AREA)
Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Inks, Pencil-Leads, Or Crayons (AREA)
Polymerisation Methods In General (AREA)
Macromonomer-Based Addition Polymer (AREA)

CA295,526A 1977-02-07 1978-01-24 Lithographic ink vehicle containing addition polymers and aliphatic hydrocarbon solvent Expired CA1123997A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US76639177A	1977-02-07	1977-02-07
US766,391		1977-02-07

Publications (1)

Publication Number	Publication Date
CA1123997A true CA1123997A (en)	1982-05-18

Family

ID=25076301

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA295,526A Expired CA1123997A (en)	1977-02-07	1978-01-24	Lithographic ink vehicle containing addition polymers and aliphatic hydrocarbon solvent

Country Status (13)

Country	Link
JP (1)	JPS5398385A (da)
AU (1)	AU517975B2 (da)
BE (1)	BE863624A (da)
CA (1)	CA1123997A (da)
CH (1)	CH627776A5 (da)
DE (1)	DE2803943A1 (da)
DK (1)	DK54578A (da)
FR (2)	FR2401209A1 (da)
GB (2)	GB1563669A (da)
IT (1)	IT7867238A0 (da)
NL (1)	NL7801394A (da)
NO (1)	NO780399L (da)
SE (1)	SE7801356L (da)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4162997A (en) *	1978-03-02	1979-07-31	Hercules Incorporated	Heat-fusible pastes for printing inks, adhesives and moldings
DE3337890A1 (de) *	1983-10-19	1985-05-09	Röhm GmbH, 6100 Darmstadt	Formmassen fuer optisch ablesbare datentraeger
EP0240928A3 (en) *	1986-04-07	1989-03-29	Ppg Industries, Inc.	Lithographic ink compositions
US7163779B2 (en) *	2003-12-12	2007-01-16	Konica Minolta Medical & Graphic, Inc.	Planographic printing plate material process, planographic printing plate and printing process
JP6392317B2 (ja) *	2014-02-25	2018-09-19	株式会社Ｔ＆ＫＴｏｋａ	インキ組成物、印刷物および印刷方法
JP7664015B2 (ja) *	2020-11-27	2025-04-17	花王株式会社	水性インク

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3394029A (en) *	1965-02-24	1968-07-23	Hercules Inc	Polyolefins coated with terpene acrylate polymers
US3681298A (en) *	1970-08-03	1972-08-01	Rohm & Haas	Copolymer containing isobornyl methacrylate
US3784532A (en) *	1970-09-18	1974-01-08	Rohm & Haas	Bulk polymerization process modified with solvent to reduce residual monomer content
US3940353A (en) *	1972-04-15	1976-02-24	Rohm And Haas Company	Pigment dispersions and lacquers containing copolymer of isobornyl methacrylate

1978
- 1978-01-23 GB GB2634/78A patent/GB1563669A/en not_active Expired
- 1978-01-23 GB GB1744/79A patent/GB1563670A/en not_active Expired
- 1978-01-24 CA CA295,526A patent/CA1123997A/en not_active Expired
- 1978-01-30 DE DE19782803943 patent/DE2803943A1/de not_active Withdrawn
- 1978-02-03 AU AU32997/78A patent/AU517975B2/en not_active Expired
- 1978-02-03 JP JP1061778A patent/JPS5398385A/ja active Pending
- 1978-02-03 BE BE184876A patent/BE863624A/xx unknown
- 1978-02-06 CH CH126178A patent/CH627776A5/fr not_active IP Right Cessation
- 1978-02-06 SE SE7801356A patent/SE7801356L/xx unknown
- 1978-02-06 DK DK54578A patent/DK54578A/da not_active Application Discontinuation
- 1978-02-06 NO NO780399A patent/NO780399L/no unknown
- 1978-02-06 IT IT7867238A patent/IT7867238A0/it unknown
- 1978-02-07 NL NL7801394A patent/NL7801394A/xx not_active Application Discontinuation
- 1978-02-07 FR FR7803433A patent/FR2401209A1/fr active Granted
- 1978-09-25 FR FR7827435A patent/FR2396032A1/fr not_active Withdrawn

Also Published As

Publication number	Publication date
IT7867238A0 (it)	1978-02-06
AU517975B2 (en)	1981-09-10
DE2803943A1 (de)	1978-08-10
AU3299778A (en)	1979-08-09
FR2401209A1 (fr)	1979-03-23
GB1563669A (en)	1980-03-26
BE863624A (fr)	1978-08-03
CH627776A5 (en)	1982-01-29
NO780399L (no)	1978-08-08
GB1563670A (en)	1980-03-26
FR2401209B1 (da)	1982-10-15
DK54578A (da)	1978-08-08
JPS5398385A (en)	1978-08-28
NL7801394A (nl)	1978-08-09
FR2396032A1 (fr)	1979-01-26
SE7801356L (sv)	1978-08-08

Legal Events

Date	Code	Title	Description
1999-05-18	MKEX	Expiry

Publication	Publication Date	Title
US4289678A (en)	1981-09-15	Acrylic thickener for publication gravure inks, method of preparing said thickener, ink containing the same and method of printing
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