EP0325996A1 - Microcapsules contenant un formateur de couleur - Google Patents
Microcapsules contenant un formateur de couleur Download PDFInfo
- Publication number
- EP0325996A1 EP0325996A1 EP89100748A EP89100748A EP0325996A1 EP 0325996 A1 EP0325996 A1 EP 0325996A1 EP 89100748 A EP89100748 A EP 89100748A EP 89100748 A EP89100748 A EP 89100748A EP 0325996 A1 EP0325996 A1 EP 0325996A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- microcapsules
- parts
- alkanols
- color formers
- microcapsules containing
- 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.)
- Withdrawn
Links
- 239000003094 microcapsule Substances 0.000 title claims abstract description 22
- 239000007788 liquid Substances 0.000 claims abstract description 19
- 239000011162 core material Substances 0.000 claims abstract description 15
- 239000000203 mixture Substances 0.000 claims description 13
- XUJLWPFSUCHPQL-UHFFFAOYSA-N 11-methyldodecan-1-ol Chemical compound CC(C)CCCCCCCCCCO XUJLWPFSUCHPQL-UHFFFAOYSA-N 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 2
- 239000000243 solution Substances 0.000 description 13
- 238000001816 cooling Methods 0.000 description 5
- 239000006185 dispersion Substances 0.000 description 5
- 238000000034 method Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 229920000877 Melamine resin Polymers 0.000 description 3
- 238000005984 hydrogenation reaction Methods 0.000 description 3
- LIZLYZVAYZQVPG-UHFFFAOYSA-N (3-bromo-2-fluorophenyl)methanol Chemical compound OCC1=CC=CC(Br)=C1F LIZLYZVAYZQVPG-UHFFFAOYSA-N 0.000 description 2
- IAUKWGFWINVWKS-UHFFFAOYSA-N 1,2-di(propan-2-yl)naphthalene Chemical compound C1=CC=CC2=C(C(C)C)C(C(C)C)=CC=C21 IAUKWGFWINVWKS-UHFFFAOYSA-N 0.000 description 2
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- IVJISJACKSSFGE-UHFFFAOYSA-N formaldehyde;1,3,5-triazine-2,4,6-triamine Chemical compound O=C.NC1=NC(N)=NC(N)=N1 IVJISJACKSSFGE-UHFFFAOYSA-N 0.000 description 2
- 150000002596 lactones Chemical class 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 229920000536 2-Acrylamido-2-methylpropane sulfonic acid Polymers 0.000 description 1
- XHZPRMZZQOIPDS-UHFFFAOYSA-N 2-Methyl-2-[(1-oxo-2-propenyl)amino]-1-propanesulfonic acid Chemical compound OS(=O)(=O)CC(C)(C)NC(=O)C=C XHZPRMZZQOIPDS-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- PLLBRTOLHQQAQQ-UHFFFAOYSA-N 8-methylnonan-1-ol Chemical compound CC(C)CCCCCCCO PLLBRTOLHQQAQQ-UHFFFAOYSA-N 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 description 1
- 241000294754 Macroptilium atropurpureum Species 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 238000005538 encapsulation Methods 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 229920000591 gum Polymers 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000001863 hydroxypropyl cellulose Substances 0.000 description 1
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 125000005506 phthalide group Chemical group 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- -1 rhodamine lactones Chemical class 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000001911 terphenyls Chemical class 0.000 description 1
- IAQRGUVFOMOMEM-ONEGZZNKSA-N trans-but-2-ene Chemical compound C\C=C\C IAQRGUVFOMOMEM-ONEGZZNKSA-N 0.000 description 1
Classifications
-
- 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
- B41M5/124—Duplicating or marking methods; Sheet materials for use therein using pressure to make a masked colour visible, e.g. to make a coloured support visible, to create an opaque or transparent pattern, or to form colour by uniting colour-forming components
- B41M5/165—Duplicating or marking methods; Sheet materials for use therein using pressure to make a masked colour visible, e.g. to make a coloured support visible, to create an opaque or transparent pattern, or to form colour by uniting colour-forming components characterised by the use of microcapsules; Special solvents for incorporating the ingredients
- B41M5/1655—Solvents
Definitions
- microcapsules The production and use of chemical copying systems containing microcapsules is known. Such systems with paper as a carrier material are manufactured on a large scale technically.
- the microcapsules of the prior art contain high-boiling, as a rule, aromatic liquids or polychlorinated alkanes as the core liquid. To reduce the cost, aliphatics are often added to the aromatics, the aromatic liquid serving as a solvent for the color formers. Aliphatics alone are not suitable, since they do not have sufficient dissolving power for the color formers of the prior art for use in copy systems.
- the object of the invention was to provide further liquids suitable as core liquid for microcapsules.
- the invention relates to microcapsules containing color formers, which are characterized in that, as the core material, they contain a solution of the color formers in at least one C8 to C14 alkanol (core liquid) which is liquid at room temperature.
- core liquid C8 to C14 alkanol
- the alkanols to be used according to the invention have clear advantages in the solution properties compared to the core solvents of the prior art.
- the alkanols allow the production of stable solutions of color formers which are otherwise critical in terms of solubility, so that improved mixtures can be produced for the encapsulation.
- the alkanols to be used according to the invention dissolve the known color formers rapidly at temperatures up to 95 ° C. and, after cooling, give stable solutions from which the color formers do not crystallize out. Copy systems made with these microcapsules provide clear, clear copies.
- alkanols As core liquid come at room temperature liquid C8 to C14 alkanols or mixtures of these alkanols.
- the boiling point should be> 180 ° C.
- the alkanols generally have primary hydroxyl groups.
- the alkyl radical of the alkanols can be linear or branched.
- the preferred alkanols are those obtained by hydrogenation of oxo reaction products from ⁇ -1-C7 to C13 olefins.
- the alkanols can be used alone or as a mixture with the organic liquids known as core liquid, e.g. aromatic hydrocarbons from the group of alkylnaphthalenes, terphenyls and / or alkylbenzenes and polychlorinated paraffins can be used.
- core liquid e.g. aromatic hydrocarbons from the group of alkylnaphthalenes, terphenyls and / or alkylbenzenes and polychlorinated paraffins can be used.
- Suitable color formers are the known ones, for example those from the group of the lactones, such as crystal violet lactone, the fluorans such as fluoranlactones, rhodamine lactones, diazarhodamine lactones, phthalides, spirodipyrans such as dibenzodipyrans or mixtures of these compounds.
- alkanols their mixtures with the known core liquids which contain the color formers in solution, can be enclosed in microcapsules by known processes, e.g. according to the processes of EP-A 26 914, EP-A 82 635, EP-A 133 295 and US-A 2 800 457.
- As wall materials e.g. Hydroxypropyl cellulose, carboxymethyl cellulose, gelatin, gum prabicum and melamine-formaldehyde precondensation products.
- the invention is illustrated by the following examples.
- the parts specified below are parts by weight.
- the dispersion is stirred for a further 0.5 hours, then stirred at 60 at 2000 rpm for 1 hour. The temperature is then raised to 75 ° C. and stirring is continued at 500 rpm for 2 hours. After cooling, the dispersion is adjusted to pH 7 with triethanolamine.
- the finished microcapsule dispersion contains microcapsules with an average diameter of 5-6 ⁇ m after particle size measurement in the Coulter Counter TF.
- the solids content is about 40%.
- 32 parts of the microcapsule dispersion obtained according to b) are mixed with by slow stirring 5.1 parts of cellulose flour (Arbocel 600/50 from Rettenmayer, Holzmühle, Germany), 5.1 parts of acrylic ester copolymer (50% dispersion in water) and 57.8 parts of water mixed.
- This coating color was applied with a 30 ⁇ m spiral doctor blade on coating base paper of 50 g / m2); Application weight atro 8 g / m2.
- the donor sheet (CB) obtained was written together with CF sheets (activated clay) (CB) in a typewriter (Olympia, Standard 200). The intensity of the copy is determined on the third copy.
- the carbon copy sentence is written on a surface of approx. 5 x 5 cm with small letters next to each other and one above the other.
- the reflectance of the blank papers was measured with 88% and that of the 3rd copy with 37%. I.e. the copy has an intensity of 51% and thus corresponds to the intensity of copies obtained with microcapsules containing color former solutions in diisopropylnaphthalene and aliphatic hydrocarbons.
- the isotridecanol mixture was obtained from tetramer propylene by oxosynthesis and hydrogenation of the oxo product.
- the solution obtained was encapsulated in microcapsules according to Example 1 b).
- Example 1 5.5 parts of the color former mixture specified in Example 1 are dissolved at 95 ° C. in 75.0 parts of the isotridecanol mixture used in Example 1 and 19.5 parts of di-isopropylnaphthalene (KMC 113 from the trade). The solution remains clear even after cooling. This solution was encapsulated according to the procedure described in Example 1 b). The CB papers coated with these microcapsules give easily readable copies with CF papers.
Landscapes
- Color Printing (AREA)
- Manufacturing Of Micro-Capsules (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19883802271 DE3802271A1 (de) | 1988-01-27 | 1988-01-27 | Farbbildner enthaltende mikrokapseln |
| DE3802271 | 1988-01-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| EP0325996A1 true EP0325996A1 (fr) | 1989-08-02 |
Family
ID=6346036
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP89100748A Withdrawn EP0325996A1 (fr) | 1988-01-27 | 1989-01-18 | Microcapsules contenant un formateur de couleur |
Country Status (3)
| Country | Link |
|---|---|
| EP (1) | EP0325996A1 (fr) |
| JP (1) | JPH024438A (fr) |
| DE (1) | DE3802271A1 (fr) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US11640795B2 (en) | 2018-08-29 | 2023-05-02 | Boe Technology Group Co., Ltd. | Shift register unit, gate drive circuit and drive method |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4132796C2 (de) * | 1991-10-02 | 1994-02-24 | Andre Nuyken | Verwendung einer chemisch druckanzeigenden Beschichtung auf einem Trägermaterial zur Herstellung von Fußabdrücken |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2856331A1 (de) * | 1977-12-27 | 1979-07-05 | Fuji Photo Film Co Ltd | Aufzeichnungsmaterial |
-
1988
- 1988-01-27 DE DE19883802271 patent/DE3802271A1/de not_active Withdrawn
-
1989
- 1989-01-18 EP EP89100748A patent/EP0325996A1/fr not_active Withdrawn
- 1989-01-25 JP JP1014227A patent/JPH024438A/ja active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2856331A1 (de) * | 1977-12-27 | 1979-07-05 | Fuji Photo Film Co Ltd | Aufzeichnungsmaterial |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US11640795B2 (en) | 2018-08-29 | 2023-05-02 | Boe Technology Group Co., Ltd. | Shift register unit, gate drive circuit and drive method |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH024438A (ja) | 1990-01-09 |
| DE3802271A1 (de) | 1989-08-03 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PUAI | Public reference made under article 153(3) epc to a published international application that has entered the european phase |
Free format text: ORIGINAL CODE: 0009012 |
|
| AK | Designated contracting states |
Kind code of ref document: A1 Designated state(s): DE FR GB |
|
| STAA | Information on the status of an ep patent application or granted ep patent |
Free format text: STATUS: THE APPLICATION HAS BEEN WITHDRAWN |
|
| 18W | Application withdrawn |
Withdrawal date: 19890810 |