US3850648A - Flowable hectographic compositions - Google Patents
Flowable hectographic compositions Download PDFInfo
- Publication number
- US3850648A US3850648A US00306437A US30643772A US3850648A US 3850648 A US3850648 A US 3850648A US 00306437 A US00306437 A US 00306437A US 30643772 A US30643772 A US 30643772A US 3850648 A US3850648 A US 3850648A
- Authority
- US
- United States
- Prior art keywords
- composition
- hectographic
- parts
- fatty acid
- dye
- Prior art date
- 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 - Lifetime
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 74
- 230000009969 flowable effect Effects 0.000 title claims abstract description 10
- 235000014113 dietary fatty acids Nutrition 0.000 claims abstract description 33
- 239000000194 fatty acid Substances 0.000 claims abstract description 33
- 229930195729 fatty acid Natural products 0.000 claims abstract description 33
- 150000004665 fatty acids Chemical class 0.000 claims abstract description 33
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims abstract description 11
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 10
- 239000003381 stabilizer Substances 0.000 claims abstract description 5
- 239000000975 dye Substances 0.000 claims description 29
- 239000001993 wax Substances 0.000 claims description 17
- 239000003921 oil Substances 0.000 claims description 7
- 125000002947 alkylene group Chemical group 0.000 claims description 6
- 239000001003 triarylmethane dye Substances 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 abstract description 3
- 239000013078 crystal Substances 0.000 description 11
- 238000003860 storage Methods 0.000 description 9
- 235000013869 carnauba wax Nutrition 0.000 description 6
- 239000004203 carnauba wax Substances 0.000 description 6
- 235000019198 oils Nutrition 0.000 description 6
- 229940099259 vaseline Drugs 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000004166 Lanolin Substances 0.000 description 5
- 235000019388 lanolin Nutrition 0.000 description 5
- 229940039717 lanolin Drugs 0.000 description 5
- 239000002480 mineral oil Substances 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- 235000010446 mineral oil Nutrition 0.000 description 4
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 4
- BOWVQLFMWHZBEF-KTKRTIGZSA-N oleoyl ethanolamide Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)NCCO BOWVQLFMWHZBEF-KTKRTIGZSA-N 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 3
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 3
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 3
- 239000005642 Oleic acid Substances 0.000 description 3
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000003760 tallow Substances 0.000 description 3
- 235000021314 Palmitic acid Nutrition 0.000 description 2
- 210000000988 bone and bone Anatomy 0.000 description 2
- 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 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 238000007046 ethoxylation reaction Methods 0.000 description 2
- 238000010348 incorporation Methods 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- DSEKYWAQQVUQTP-XEWMWGOFSA-N (2r,4r,4as,6as,6as,6br,8ar,12ar,14as,14bs)-2-hydroxy-4,4a,6a,6b,8a,11,11,14a-octamethyl-2,4,5,6,6a,7,8,9,10,12,12a,13,14,14b-tetradecahydro-1h-picen-3-one Chemical compound C([C@H]1[C@]2(C)CC[C@@]34C)C(C)(C)CC[C@]1(C)CC[C@]2(C)[C@H]4CC[C@@]1(C)[C@H]3C[C@@H](O)C(=O)[C@@H]1C DSEKYWAQQVUQTP-XEWMWGOFSA-N 0.000 description 1
- TWJNQYPJQDRXPH-UHFFFAOYSA-N 2-cyanobenzohydrazide Chemical compound NNC(=O)C1=CC=CC=C1C#N TWJNQYPJQDRXPH-UHFFFAOYSA-N 0.000 description 1
- 244000060011 Cocos nucifera Species 0.000 description 1
- 235000013162 Cocos nucifera Nutrition 0.000 description 1
- OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 description 1
- 235000021360 Myristic acid Nutrition 0.000 description 1
- TUNFSRHWOTWDNC-UHFFFAOYSA-N Myristic acid Natural products CCCCCCCCCCCCCC(O)=O TUNFSRHWOTWDNC-UHFFFAOYSA-N 0.000 description 1
- 239000005662 Paraffin oil Substances 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- 235000019484 Rapeseed oil Nutrition 0.000 description 1
- 244000000231 Sesamum indicum Species 0.000 description 1
- 235000003434 Sesamum indicum Nutrition 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 235000019486 Sunflower oil Nutrition 0.000 description 1
- -1 Vaseline Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 235000013871 bee wax Nutrition 0.000 description 1
- 239000012166 beeswax Substances 0.000 description 1
- 229940082483 carnauba wax Drugs 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 150000002148 esters Chemical class 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
- 238000000227 grinding Methods 0.000 description 1
- 239000000976 ink Substances 0.000 description 1
- 235000020778 linoleic acid Nutrition 0.000 description 1
- OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000003801 milling Methods 0.000 description 1
- 239000012170 montan wax Substances 0.000 description 1
- 239000010697 neat foot oil Substances 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 235000021313 oleic acid Nutrition 0.000 description 1
- 125000005429 oxyalkyl group Chemical group 0.000 description 1
- 239000012186 ozocerite Substances 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 239000010491 poppyseed oil Substances 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000002600 sunflower oil Substances 0.000 description 1
- 238000010345 tape casting Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000010023 transfer printing Methods 0.000 description 1
- PHYFQTYBJUILEZ-IUPFWZBJSA-N triolein Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C/CCCCCCCC)COC(=O)CCCCCCC\C=C/CCCCCCCC PHYFQTYBJUILEZ-IUPFWZBJSA-N 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- LLWJPGAKXJBKKA-UHFFFAOYSA-N victoria blue B Chemical compound [Cl-].C1=CC(N(C)C)=CC=C1C(C=1C=CC(=CC=1)N(C)C)=C(C=C1)C2=CC=CC=C2C1=[NH+]C1=CC=CC=C1 LLWJPGAKXJBKKA-UHFFFAOYSA-N 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
- C09D11/03—Printing inks characterised by features other than the chemical nature of the binder
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
- B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
- B41M5/00—Duplicating or marking methods; Sheet materials for use therein
- B41M5/025—Duplicating or marking methods; Sheet materials for use therein by transferring ink from the master sheet
- B41M5/06—Duplicating or marking methods; Sheet materials for use therein by transferring ink from the master sheet using master sheets coated with jelly-like materials, e.g. gelatin
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S516/00—Colloid systems and wetting agents; subcombinations thereof; processes of
- Y10S516/01—Wetting, emulsifying, dispersing, or stabilizing agents
- Y10S516/07—Organic amine, amide, or n-base containing
Definitions
- hectographic compositions the dyes are dispersed in a wax composition with the aid of grinding equipment.
- the resulting hectographic compositions are transferred, in the molten state, to tanks from which they are applied to a paper by, say, a printing or knife-coating technique. Hectographic papers of this kind may then be used for making copies in a simple manner by transfer printing.
- compositions During storage and processing of hectographic compositions in the liquid state, a considerable increase in viscosity frequently occurs. Before the coating operation commences or is complete the compositions become so thick that the production rate must be reduced considerably. When stored forv long periods, the compositions stiffen irreversibly and thus become useless for coating operations.
- hectographic compositions remain stable and flowable on storage when they contain alkoxylated fatty acid alkanolamides in a concentration of from 1 to by weight based on the total weight of the composition.
- the alkoxylated fatty acid alkanolamides used as additives in the hectographic compositions of the invention are fatty acid amides containing oxyalkyl groups, preferably obtained by alkoxylating fatty acid alkanolamides.
- the ethanolamides and in particular the monoethanolamides are especially preferred.
- Particularly suitable fatty acids are the higher fatty acids or mixtures thereof such as palmitic acid, stearic acid, oleic acid, tallow fatty acid, coconut fatty acid and similar acids.
- the fatty acid alkanolamides are reacted with alkylene oxides, preferably ethylene oxide.
- the molar ratio of fatty acid alkanolamide to alkylene oxide in this reaction is conveniently from 1:5 to 1:25 and preferably from 1:8 to 1:15.
- the alkoxylated fatty acid alkanolamide is incorporated in the hectographic composition of the invention in an amount of from 1 to 20% and preferably from 2 to 10% by weight before, during or after the dye component has been ground together with the wax component for dispersion therein.
- the alkoxylated fatty acid alkanolamide may be added to the dye component during its manufacture or during milling thereof, or it may be added to the wax component before this is mixed with the dye.
- the dye component forms the major component of the hectographic composition, usually being present therein in an amount of from to 60% by weight based on the total weight of the composition, and suitable dyes for use in the present invention are all conventional hectographic dyes, particularly triarylmethane dyes such as Crystal Violet (C.l. No. 42,555), Methyl Violet (C.l. No. 43,535) and Victoria Blue B (C.l. No. 44,045), as well as mixtures of said dyes.
- triarylmethane dyes such as Crystal Violet (C.l. No. 42,555), Methyl Violet (C.l. No. 43,535) and Victoria Blue B (C.l. No. 44,045), as well as mixtures of said dyes.
- Suitable waxes for use in the hectographic composition are any of the usual natural and synthetic waxes and oils such as carnauba wax, lanolin, Vaseline, paraffin wax, ozocerite, beeswax, montan waxes crude or modified (ester wax), mineral oils, paraffin oil.
- chine oil spindle oil, neats foot oil, bone oil, peanut oil, castor oil, sunflower oil, rapeseed oil, poppy seed oil and olein, either alone or in the form of mixtures.
- hectographic compositions of the invention remain stable and flowable when stored for long periods and when subjected to the elevated temperatures normally used in further processing and they are thus eminently suitable for coating hectographic papers.
- non-ionic emulsifiers are used in order to reduce the hardness of diand tri-arylmethane dyes and thus to make such dyes more suitable for hectographic applications, such emulsifiers have no or no appreciable viscosity stabilizing effect in hectographic compositions.
- EXAMPLE 1 354 Parts of moisture-containing Crystal Violet (solids content 200 parts) are melted over a water bath to form a solution. 10 Parts of reaction product of 1 mole of oleic monoethanolamide and 10 moles of ethylene oxide are stirred into said solution. The composition is stirred and the water evaporated therefrom until it stiffens, whereupon it is dried in a vacuum drying cabinet at C until the moisture level is only about 2%. The resulting lumps are milled to a dye powder which is suitable for incorporation in hectographic compositions such as is described for example in Example 4.
- EXAMPLE 2 20 Parts of a reaction product of 1 mole of tallow fatty acid monoethanolamide (monoethanol mixture obtained from an acid mixture of 47% of oleic acid, 29% of palmitic acid, 18% of steariic acid, 3% of myristic acid and 3% of linoleic acid) and 12 moles of ethylene oxide are homogeneously mixed with 30 parts of water and then stirred into 354 parts of a dye melt as described in Example 1, the resulting mixture being further processed as described in Example 1. There is obtained a Crystal Violet dye composition suitable for incorporation in a hectographic composition as described in Example 5 for example.
- tallow fatty acid monoethanolamide monoethanol mixture obtained from an acid mixture of 47% of oleic acid, 29% of palmitic acid, 18% of steariic acid, 3% of myristic acid and 3% of linoleic acid
- EXAMPLE 3 300 Parts of Crystal Violet (solids content parts) and 60 parts of Methyl Violet (solids content 30 parts) are melted over a water bath and mixed with 25 parts of a reaction product of 1 mole of oleic ethanolamide and 10 moles of ethylene oxide. The mixture is processed as described in Example 1 to give a dye composition having a moisture content of about 3%.
- EXAMPLE 4 144 Parts of a wax mixture consisting of 36 parts of carnauba wax, 36 parts of Vaseline, 51 parts of lanolin and 21 parts of mineral oil are ground together with 156 parts of Crystal Violet dye powder as obtained in Example 1 using 600 parts of steatite spheres in a stirred ball mill at 95C, the speed of rotation being 800 rpm. After 90 minutes, the resulting hectographic compositionis removed from the spheres and its viscosity is measured in an Epprecht viscometer (measuring system B, velocity stage I) at 95C immediately and during a storage period of 24 hours. The test results show an initial viscosity of 580 centipoise, which does not change in the course of 24 hours. A control dye composition not containing the ethoxylated oleic monoethanolamide shows an initial viscosity of 700 centipoise which rises in the course of 24 hours at 95C to 1,500 centipoise.
- EXAMPLE 5 The Crystal Violet dye composition obtained in Example 2 is ground together with a wax composition in a stirred ball mill following the procedure described in Example 4. Viscosity measurements show an initial viscosity of from 520 to 550 centipoise at 95C, the viscosity remaining at this level throughout a storage period of 24 hours at 95C.
- EXAMPLE 6 48 Parts of a wax mixture consisting of 12 parts of carnauba wax, 12 parts of vaseline, 17 parts of lanolin and 7 parts of mineral oil are ground together with 52 parts of the dye composition obtained in Example 1 on a three-roll mill, the mixture being passed through the mill 4 times at room temperature and a pressure of 60 atmospheres gage and twice at 95C at a pressure of from 10 to atmospheres gage.
- the viscosity of the hectographic composition thus obtained is the same after storage for 4 days at 95C as before storage, i.e. 370 centipoise.
- the control dye composition prepared without said ethoxylation product shows a rise in viscosity over the said period of from 480 to 1,500 centipolse.
- EXAMPLE 7 13 Parts of carnauba wax, 17 parts of vaseline, 13 parts of bone oil, 2 parts of oleic acid and 55 parts of Crystal Violet are ground together with 2.75 parts or 5 parts or 10 parts of a reaction product of 1 mole of tallow fatty acid monoethanolamide and 12 moles of ethylene oxide in the three-roll mill as described in Example 5. Viscosity measurements of the resulting hectographic composition give initial values of 510, 440 and 370 centipoise at 95C respectively, these values not changing over a storage period of 24 hours at 95C. The corresponding composition not containing the ethoxylation product shows an initial viscosity of 1,100 centipoise and values above 2,000 centipoise after storage for 24 hours at 95C.
- EXAMPLE 8 354 Parts of moisture-containing Crystal Violet (solids content 200 parts) are melted over a water bath to form a solution. 4 parts of a reaction product of l mole of oleic monoethanolamide and 10 moles of ethylene oxide are stirred into said solution. Further treatment of the composition is as described in Example 1. 156 Parts of the resulting Crystal Violet dye powder are ground together with 144 parts of a wax mixture consisting of 36 parts of carnauba wax, 36 parts of vaseline, 51 parts of lanolin and 21 parts of mineral oil, as described in Example 4, to form a hectographic composition. Viscosity measurements carried out in the manner described above give an initial viscosity of 600 centipoise at C, this showing no change over 24 hours.
- EXAMPLE 9 354 Parts of moisture-containing Crystal Violet (solids content 200 parts) are melted over a water bath to form a solution. 40 Parts of a reaction product of 1 mole of oleic monoethanolamide and 10 moles of ethylene oxide are stirred into said solution. Further treatment of the composition is as described in Example 1. 156 Parts of the resulting Crystal Violet dye powder are ground together with 144 parts of a wax mixture consisting of 36 parts of carnauba wax, 36 parts of Vaseline, 51 parts of lanolin and 21 parts of mineral oil as described in Example 4 to provide a hectographic composition. The viscosity measurements carried out as described above give an initial viscosity of 500 centipoise at 95C, this showing no change over 24 hours.
- a flowable hectographic composition consisting essentially of (a) a hectographic dye, (b) a wax and (c) as a viscosity stabilizer an alkoxylated fatty acid alkanolamide in a concentration of from 1 to 20% by weight ofthe total weight of the hectographic compositron.
- composition as claimed in claim 1 wherein the concentration of said alkoxylated fatty acid alkanolamide is about 2 to 10% by weight.
- composition as claimed in claim 1 wherein said wax is a substance selected from the class consisting of natural and synthetic waxes, mixtures thereof, and admixtures thereof with oils.
- composition as claimed in claim 1 in which the molar ratio of the fatty acid alkanolamide to the alkylene oxide is about 1:5 to 1:25.
- composition as claimed in claim 1 in which the molar ratio of the fatty acid alkanolamide to the alkylene oxide is about 1:8 to 1:15.
Landscapes
- Chemical & Material Sciences (AREA)
- Wood Science & Technology (AREA)
- General Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Paints Or Removers (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Medicinal Preparation (AREA)
- Cosmetics (AREA)
- Duplication Or Marking (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE2156762A DE2156762C3 (de) | 1971-11-16 | 1971-11-16 | Fliessfähige Hektographenmassen |
Publications (1)
Publication Number | Publication Date |
---|---|
US3850648A true US3850648A (en) | 1974-11-26 |
Family
ID=5825227
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US00306437A Expired - Lifetime US3850648A (en) | 1971-11-16 | 1972-11-14 | Flowable hectographic compositions |
Country Status (6)
Country | Link |
---|---|
US (1) | US3850648A (en:Method) |
JP (1) | JPS4858907A (en:Method) |
CH (1) | CH565852A5 (en:Method) |
DE (1) | DE2156762C3 (en:Method) |
FR (1) | FR2160444B1 (en:Method) |
GB (1) | GB1405160A (en:Method) |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4752381A (en) * | 1987-05-18 | 1988-06-21 | Nalco Chemical Company | Upgrading petroleum and petroleum fractions |
US5000786A (en) * | 1987-11-02 | 1991-03-19 | Seiko Epson Corporation | Ink composition and ink jet recording apparatus and method |
US5308390A (en) * | 1992-09-17 | 1994-05-03 | Deluxe Corporation | Ink composition and method of making and using such composition |
US5431721A (en) * | 1992-09-17 | 1995-07-11 | Deluxe Corporation | Ink varnish and composition and method of making the same |
US5549741A (en) * | 1992-09-17 | 1996-08-27 | Deluxe Corporation | Ink varnish composition |
Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2752255A (en) * | 1953-04-29 | 1956-06-26 | Wallace G Clarke | Crystal violet composition |
US2752254A (en) * | 1953-04-29 | 1956-06-26 | Gen Aniline & Film Corp | Hectograph black |
US2824812A (en) * | 1954-12-20 | 1958-02-25 | Gen Aniline & Film Corp | Hectograph composition |
US3097219A (en) * | 1961-08-07 | 1963-07-09 | Commercial Solvents Corp | Oxyalkylated carboxylic acid amides and production thereof |
US3565658A (en) * | 1968-07-19 | 1971-02-23 | Phillips Petroleum Co | Carbon black dispersing agent |
US3755244A (en) * | 1971-06-02 | 1973-08-28 | Hercules Inc | Polyolefin pigment dispersions |
-
1971
- 1971-11-16 DE DE2156762A patent/DE2156762C3/de not_active Expired
-
1972
- 1972-10-05 CH CH1459972A patent/CH565852A5/xx not_active IP Right Cessation
- 1972-11-13 JP JP47113069A patent/JPS4858907A/ja active Pending
- 1972-11-14 US US00306437A patent/US3850648A/en not_active Expired - Lifetime
- 1972-11-14 FR FR7240344A patent/FR2160444B1/fr not_active Expired
- 1972-11-15 GB GB5272372A patent/GB1405160A/en not_active Expired
Patent Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2752255A (en) * | 1953-04-29 | 1956-06-26 | Wallace G Clarke | Crystal violet composition |
US2752254A (en) * | 1953-04-29 | 1956-06-26 | Gen Aniline & Film Corp | Hectograph black |
US2824812A (en) * | 1954-12-20 | 1958-02-25 | Gen Aniline & Film Corp | Hectograph composition |
US3097219A (en) * | 1961-08-07 | 1963-07-09 | Commercial Solvents Corp | Oxyalkylated carboxylic acid amides and production thereof |
US3565658A (en) * | 1968-07-19 | 1971-02-23 | Phillips Petroleum Co | Carbon black dispersing agent |
US3755244A (en) * | 1971-06-02 | 1973-08-28 | Hercules Inc | Polyolefin pigment dispersions |
Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4752381A (en) * | 1987-05-18 | 1988-06-21 | Nalco Chemical Company | Upgrading petroleum and petroleum fractions |
US5000786A (en) * | 1987-11-02 | 1991-03-19 | Seiko Epson Corporation | Ink composition and ink jet recording apparatus and method |
US5124719A (en) * | 1987-11-02 | 1992-06-23 | Seiko Epson Corporation | Ink jet recording method |
US5308390A (en) * | 1992-09-17 | 1994-05-03 | Deluxe Corporation | Ink composition and method of making and using such composition |
US5338351A (en) * | 1992-09-17 | 1994-08-16 | Deluxe Corporation | Ink composition and method of making, using and recovering such composition |
US5382282A (en) * | 1992-09-17 | 1995-01-17 | Deluxe Corporation | Ink composition and method of making, using and recovering such composition |
US5431721A (en) * | 1992-09-17 | 1995-07-11 | Deluxe Corporation | Ink varnish and composition and method of making the same |
US5549741A (en) * | 1992-09-17 | 1996-08-27 | Deluxe Corporation | Ink varnish composition |
Also Published As
Publication number | Publication date |
---|---|
FR2160444A1 (en:Method) | 1973-06-29 |
DE2156762B2 (de) | 1974-04-04 |
JPS4858907A (en:Method) | 1973-08-18 |
FR2160444B1 (en:Method) | 1977-07-22 |
DE2156762C3 (de) | 1974-11-07 |
DE2156762A1 (de) | 1973-05-30 |
GB1405160A (en) | 1975-09-03 |
CH565852A5 (en:Method) | 1975-08-29 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US3840383A (en) | Colored inorganic pigments | |
US2272057A (en) | Resin emulsion | |
US3565658A (en) | Carbon black dispersing agent | |
US2426248A (en) | Manufacture of carbon transfer ink | |
US2971922A (en) | Organophilic mineral compositions | |
US3850648A (en) | Flowable hectographic compositions | |
US2893886A (en) | Iron blue pigment composition and process for its manufacture | |
US4655960A (en) | Foam inhibitors for aqueous synthetic resin compositions | |
US2374931A (en) | Wax composition | |
US2868734A (en) | Liquid defoaming composition | |
US2450534A (en) | Emulsion printing inks | |
US3298849A (en) | Amine modified clay and method | |
US2234934A (en) | Wax suspension | |
US4655961A (en) | Foam inhibitors for aqueous dispersions and solutions of synthetic resins | |
US2392657A (en) | Induline ink toners and carbon inks | |
US3708334A (en) | Method of marking the skin or fur of animals | |
JPS59142835A (ja) | 油含有量の高い安定な水中油型エマルジヨン | |
US2288351A (en) | Wax emulsion | |
US2392658A (en) | Methyl violet ink toners and carbon inks | |
US2225392A (en) | Waxing and polishing composition | |
US2606842A (en) | Stabilized rosin size | |
US2514312A (en) | Stabilized iron carbonyl | |
US2501127A (en) | Basic zinc salicylate | |
US2545125A (en) | Image-forming composition and a process of making it | |
US2543487A (en) | Composition for treating mineral wool |