GB1564931A - Dye solvents - Google Patents
Dye solvents Download PDFInfo
- Publication number
- GB1564931A GB1564931A GB5094376A GB5094376A GB1564931A GB 1564931 A GB1564931 A GB 1564931A GB 5094376 A GB5094376 A GB 5094376A GB 5094376 A GB5094376 A GB 5094376A GB 1564931 A GB1564931 A GB 1564931A
- Authority
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- United Kingdom
- Prior art keywords
- ether
- solvent
- chromogen
- arylalkyl
- solvent according
- 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
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- 239000002904 solvent Substances 0.000 title claims description 56
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 claims description 24
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 24
- 239000000203 mixture Substances 0.000 claims description 22
- MHDVGSVTJDSBDK-UHFFFAOYSA-N dibenzyl ether Chemical compound C=1C=CC=CC=1COCC1=CC=CC=C1 MHDVGSVTJDSBDK-UHFFFAOYSA-N 0.000 claims description 18
- -1 benzyl a-methylbenzyl ether Chemical compound 0.000 claims description 17
- 125000004432 carbon atom Chemical group C* 0.000 claims description 16
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 239000003795 chemical substances by application Substances 0.000 claims description 12
- WNZQDUSMALZDQF-UHFFFAOYSA-N isobenzofuranone Natural products C1=CC=C2C(=O)OCC2=C1 WNZQDUSMALZDQF-UHFFFAOYSA-N 0.000 claims description 12
- 239000000463 material Substances 0.000 claims description 11
- 230000001235 sensitizing effect Effects 0.000 claims description 10
- 150000001911 terphenyls Chemical class 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 239000003085 diluting agent Substances 0.000 claims description 7
- 239000004927 clay Substances 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 238000005984 hydrogenation reaction Methods 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000001624 naphthyl group Chemical class 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 125000006267 biphenyl group Chemical class 0.000 claims description 3
- 230000004888 barrier function Effects 0.000 claims description 2
- 150000001555 benzenes Chemical class 0.000 claims description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims description 2
- 239000002480 mineral oil Substances 0.000 claims description 2
- 235000015112 vegetable and seed oil Nutrition 0.000 claims description 2
- 239000008158 vegetable oil Substances 0.000 claims description 2
- 235000010446 mineral oil Nutrition 0.000 claims 1
- 150000002170 ethers Chemical class 0.000 description 8
- LIZLYZVAYZQVPG-UHFFFAOYSA-N (3-bromo-2-fluorophenyl)methanol Chemical compound OCC1=CC=CC(Br)=C1F LIZLYZVAYZQVPG-UHFFFAOYSA-N 0.000 description 4
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 239000003086 colorant Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 150000002431 hydrogen Chemical group 0.000 description 2
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 2
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 2
- 239000003350 kerosene Substances 0.000 description 2
- 239000003094 microcapsule Substances 0.000 description 2
- PGFIEPSTTMPZQL-UHFFFAOYSA-N 1-[1-(1-naphthalen-1-yl-2-phenylethoxy)-2-phenylethyl]naphthalene Chemical compound C(C1=CC=CC=C1)C(C1=CC=CC2=CC=CC=C12)OC(CC1=CC=CC=C1)C1=CC=CC2=CC=CC=C12 PGFIEPSTTMPZQL-UHFFFAOYSA-N 0.000 description 1
- TVBYFUMVFJKKNJ-UHFFFAOYSA-N 1-cyclohex-2-en-1-yl-4-cyclohex-3-en-1-ylbenzene Chemical group C1CCC=CC1C1=CC=C(C2CC=CCC2)C=C1 TVBYFUMVFJKKNJ-UHFFFAOYSA-N 0.000 description 1
- UJIUKTDUCYLQBN-UHFFFAOYSA-N 1-methyl-4-[(4-methylphenyl)methoxymethyl]benzene Chemical compound C1=CC(C)=CC=C1COCC1=CC=C(C)C=C1 UJIUKTDUCYLQBN-UHFFFAOYSA-N 0.000 description 1
- BHNHHSOHWZKFOX-UHFFFAOYSA-N 2-methyl-1H-indole Chemical compound C1=CC=C2NC(C)=CC2=C1 BHNHHSOHWZKFOX-UHFFFAOYSA-N 0.000 description 1
- VXVRAGONKSWKEZ-UHFFFAOYSA-N 3,3-bis(1,2-dimethylindol-3-yl)-2-benzofuran-1-one Chemical compound C1=CC=C2C(C3(C4=CC=CC=C4C(=O)O3)C3=C(N(C4=CC=CC=C43)C)C)=C(C)N(C)C2=C1 VXVRAGONKSWKEZ-UHFFFAOYSA-N 0.000 description 1
- QUURGNIUKDDPDS-UHFFFAOYSA-N 3,3-bis(2-methyl-1h-indol-3-yl)-2-benzofuran-1-one Chemical class C1=CC=C2C(C3(C4=CC=CC=C4C(=O)O3)C=3C4=CC=CC=C4NC=3C)=C(C)NC2=C1 QUURGNIUKDDPDS-UHFFFAOYSA-N 0.000 description 1
- ABJAMKKUHBSXDS-UHFFFAOYSA-N 3,3-bis(6-amino-1,4-dimethylcyclohexa-2,4-dien-1-yl)-2-benzofuran-1-one Chemical compound C1=CC(C)=CC(N)C1(C)C1(C2(C)C(C=C(C)C=C2)N)C2=CC=CC=C2C(=O)O1 ABJAMKKUHBSXDS-UHFFFAOYSA-N 0.000 description 1
- KNNGWESDZOFDIV-UHFFFAOYSA-N 3,3-bis[4-(methylamino)phenyl]-2-benzofuran-1-one Chemical compound C1=CC(NC)=CC=C1C1(C=2C=CC(NC)=CC=2)C2=CC=CC=C2C(=O)O1 KNNGWESDZOFDIV-UHFFFAOYSA-N 0.000 description 1
- MQJTWPAGXWPEKU-UHFFFAOYSA-N 3-[4-(dimethylamino)phenyl]-3-(1,2-dimethylindol-3-yl)-2-benzofuran-1-one Chemical compound C1=CC(N(C)C)=CC=C1C1(C=2C3=CC=CC=C3N(C)C=2C)C2=CC=CC=C2C(=O)O1 MQJTWPAGXWPEKU-UHFFFAOYSA-N 0.000 description 1
- OPLBFHRSNKSMKD-UHFFFAOYSA-N 3H-2-benzofuran-1-one 1H-indole Chemical class C1=CC=C2NC=CC2=C1.C1=CC=C2C(=O)OCC2=C1 OPLBFHRSNKSMKD-UHFFFAOYSA-N 0.000 description 1
- LXIQJYAYQYNRCS-UHFFFAOYSA-N 4-(4-phenylbutoxy)butylbenzene Chemical compound C=1C=CC=CC=1CCCCOCCCCC1=CC=CC=C1 LXIQJYAYQYNRCS-UHFFFAOYSA-N 0.000 description 1
- RNRINRUTVAFUCG-UHFFFAOYSA-N 5-(dimethylamino)-3,3-bis(1,2-dimethylindol-3-yl)-2-benzofuran-1-one Chemical compound C1=CC=C2C(C3(C=4C5=CC=CC=C5N(C)C=4C)OC(=O)C4=CC=C(C=C43)N(C)C)=C(C)N(C)C2=C1 RNRINRUTVAFUCG-UHFFFAOYSA-N 0.000 description 1
- KJFCMURGEOJJFA-UHFFFAOYSA-N 5-(dimethylamino)-3,3-bis(9-ethylcarbazol-3-yl)-2-benzofuran-1-one Chemical compound C1=CC=C2C3=CC(C4(C5=CC(=CC=C5C(=O)O4)N(C)C)C=4C=C5C6=CC=CC=C6N(C5=CC=4)CC)=CC=C3N(CC)C2=C1 KJFCMURGEOJJFA-UHFFFAOYSA-N 0.000 description 1
- UJIFZLCSKDRXCZ-UHFFFAOYSA-N 6-(dimethylamino)-3-[4-(dimethylamino)phenyl]-3-(1-methylpyrrol-2-yl)-2-benzofuran-1-one Chemical compound C1=CC(N(C)C)=CC=C1C1(C=2N(C=CC=2)C)C2=CC=C(N(C)C)C=C2C(=O)O1 UJIFZLCSKDRXCZ-UHFFFAOYSA-N 0.000 description 1
- IPAJDLMMTVZVPP-UHFFFAOYSA-N Crystal violet lactone Chemical compound C1=CC(N(C)C)=CC=C1C1(C=2C=CC(=CC=2)N(C)C)C2=CC=C(N(C)C)C=C2C(=O)O1 IPAJDLMMTVZVPP-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 239000005662 Paraffin oil Substances 0.000 description 1
- ZKURGBYDCVNWKH-UHFFFAOYSA-N [3,7-bis(dimethylamino)phenothiazin-10-yl]-phenylmethanone Chemical group C12=CC=C(N(C)C)C=C2SC2=CC(N(C)C)=CC=C2N1C(=O)C1=CC=CC=C1 ZKURGBYDCVNWKH-UHFFFAOYSA-N 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 239000004359 castor oil Chemical class 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 239000002285 corn oil Chemical class 0.000 description 1
- 235000005687 corn oil Nutrition 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000005538 encapsulation Methods 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000005562 fading Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Chemical class 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
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229940107698 malachite green Drugs 0.000 description 1
- 230000000873 masking effect Effects 0.000 description 1
- 125000005506 phthalide group Chemical group 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000003549 soybean oil Chemical class 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 125000005023 xylyl group Chemical group 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
Landscapes
- Color Printing (AREA)
- Carbon And Carbon Compounds (AREA)
- Coloring (AREA)
Description
(54) DYE SOLVENTS
(71) We, MONSANTO EUROPE S.A., a Belgian Company, of Avenue de Tervuren,270--272, 1150 Bruxelles, Belgium, do hereby declare the invention, for which we pray that a patent may be granted to us, and the method by which it is to be performed, to be particularly described in and by the following statement: This invention relates to solvents and solutions which are useful in the production of carbonless copying paper.
The most widely used form of carbonless copying paper comprises a two-sheet system in which the under surface of the top sheet has a coating of mircrocapsules of a solution of a colourless chromogen, while the upper surface of the lower (receiver) sheet has an absorbent coating including a sensitizing agent for the chromogen. When a marking instrument is applied to the top sheet, the microcapsules are locally ruptured, thereby releasing the chromogen solution from the affected microcapsules to react with the underlying sensitizing agent and form coloured marks on the receiver sheet corresponding to the marks applied to the top sheet.
It is important that the marks on the receiver sheet should rapidly develop to a legible intensity of colour. Speed and intensity of colour development are dependent on various factors, including the nature of the solvent and the nature of the sensitizing agent.
For example, the hydrogenated terphenyls, which are amongst the solvents which have been proposed for use as chromogen solvents in carbonless copying paper systems, give a rapid development of colour with clay coated receiver sheets but a low colour intensity, and with resin-coated receiver sheets, give both relatively slow colour development and low colour intensity. We have now discovered that the addition of certain di(arylalkyl)ethers to a hydrogenated terphenyl gives a solvent having a considerably improved performance in carbonless copying paper systems compared with the hydrogenated terphenyls alone.
The di(arylalkyl)ethers useful in the present invention are those of the formula
wherein each R represents hydrogen, an alkyl group or a cycloalkyl group, each R' represents an alkyl group or a halogen atom, each n is an integer of from 1 to 6 and each m is 0 or an integer of from 1 to v, and each Rm'-(Ar) represents an aryl group when m is 0 or an alkyl- and/or halogen-substituted aryl group when m is a said integer. Each Rq'(Ar) can, for example, be an unsubstituted or alkyl- and/or halogen-substituted phenyl, naphthyl or biphenyl group. Each symbol R, Ar, R', n and m can have a value which is the same as or different from that or those of the other symbols R, Ar, R', n and m respectively in the formula.
The solvent of the present invention accordingly comprises a mixture of a hydrogenated terphenyl and a di(arylalkyl)ether as defined above.
The invention also includes a solution, in a solvent of the invention, of a chromogen suitable for use in a carbonless copying paper system.
A further aspect of the invention is a pressure-sensitive mark-recording system comprising (a) sheet material, (b) mark-forming components supported by the sheet material and arranged in juxtaposition but in unreactive condition, the said components comprising a chromogen and a sensitizer, for example an acid clay, for the chromogen to produce a colour when brought into contact with the chromogen in the presence of a solvent for the chromogen, and (c) a solvent of the invention supported by the sheet material but separated from the sensitizing agent by a physical barrier which is rupturable on the application of a marking instrument to the sheet material.
Especially in systems employing clay coated receiver sheets, the effect of the di(arylalkyl) ethers is apparent at low concentrations in the hydrogenated terphenyls, and a feature of the present invention is a solvent comprising a mixture of a hydrogenated terphenyl and a di(arylalkyl)ether as defined above, in which mixture the proportion by weight of the di (arylalkyl)ether is not more than 15%.
The hydrogenated terphenyls which can be used as a component of the solvent of the present invention include mixtures in various proportions of fully hydrogenated terphenyls, partially hydrogenated terphenyls, for example hexahydroterphenyl ands and dodecahydroterphenyls, and terphenyl itself. Commercially available hydrogenated terphenyis include Santosol 340 and Santosol 300, which are terphenyls partially hydrogenated to different extents, the latter having a higher degree of residual aromaticity than the former.
The preferred di(arylalkyl)ethers for use in the present invention are those wherein the number of carbon atoms in the two
groups does not exceed the total number of carbon atoms in the two Ar nuclei. Further features of preferred di(arylalkyl)ethers are that each R is hydrogen or an alkyl group of from 1 to 6 carbon atoms, especially a methyl group, and that if R represents a cycloalkyl group, this is a cyclohexyl group.
R' in the above formula is preferably an alkyl group of from 1 to 12 carbon atoms, more especially an alkyl group of from 1 to 4 carbon atoms, for example methyl, ethyl, isopropyl or t-butyl. Preferably R' and the value of m are such that the total number of carbon atoms in Rm' does not exceed 6.
Thus (Ar)Rmt can, for example, represent a phenyl, tolyl, xylyl, ethylphenyl, naphthyl, methylnaphthyl, isopropylnaphthyl, biphenyl or t-butylbiphenyl radical. If a halogen atom, R' is preferably chlorine, such that --(Ar)3R,: may represent, for example, a chlorophenyl radical.
In respect of n, preferred di(arylalkyl)ethers for use in the present invention are those in which each n has the value 1 or 2.
Specific examples of di(arylalkyl)ethers within the above formula are: dibenzyl ether, benzyl a-methylbenzyl ether, di(a-methyl benzyl ) ether, di(a-ethylbenzyl)ether, di (,a- dimethylbenzyl)ether, di(4 - methylbenzyl)ether, benzyl -naphthylmethyl ether, benzyl P-phenethyl ether and di(4-phenyl-n-butyl)ether.
As indicated above, certain preferred solvents of the present invention contain not more than 15% by weight of di(arylalkyl)ether. The latter component may be a single compound or a mixture of different di(arylalkyl)ethers. The composition of the solvent corresponding to maximum efficiency, as judged by print intensity after a given time, will vary, depending on the particular hydrogenated terphenyl and ether or ether mixture employed, but usually maximum efficiency is observed with the amount of ether not more than 10% of the weight of the mixture, for example within the range 1% to 10% or 1.5% to 7.5% by weight.
The solvents of the present invention may be used alone or in combination with diluents in forming solutions of chromogens for use in the production of carbonless copying paper.
The diluent, if used, is usually an inert liquid miscible in all proportions with the solvent of the invention, and may, for example, be used in an amount of up to three times the weight of the solvent. Examples of suitable diluents include mineral and vegetable oils, such as kerosene, paraffin oil, alkylated benzenes, castor oil, soybean oil, and corn oil.
These diluents function to alter such physical properties of the solvent, for instance viscosity or vapor pressure, as may be desired for optimum handling or processing. In using the solvents of the invention in the production of carbonless copying paper systems, they may also be mixed with other compounds which are not merely diluents, but are themselves active in the sense of enhancing the speed or intensity of print development in carbonless copying paper systems. Such compounds generally have at least one aromatic nucleus in the molecular structure, and include for example certain aromatic naphthas, Cl~l2 alkyl-naphthalenes and -biphenyls, and benzyl alkyl-benzenes.
The solvents may also contain certain additives specifically intended to alter or control the final properties of the fluid, as for example viscosity control agents, vapor pressure control agents, freezing point depressants, odor masking agents and antioxidants.
The chromogen used in the present invention is usually an aromatic compound containing a double bond system which is converted to a more highly polarized conjugated and coloured form when reacted with an acidic sensitizing material. A particularly preferred class of chromogens include compounds of the phthalide type, for instance crystal violet lactone which is 3,3 - bis(p - dimethylaminophenyl) - 6 - dimethylaminophthalide, and malachite green lactone which is 3,3 - bis (p - dimethylaminophenyl) phthalide.Other phthalide-derived chromogenic materials in dude 3,3 - bis(p - m - dipropylaminophenyl)phthalide, 3,3 - bis(p - methylaminophenyl)phthalide, 3 - (phenyl) - 3 - (indole - 3 yl) - phthalides such as 3 - (p - dimethylaminophenyl) - 3 -(1,2 - dimethyl - indol3 - yl)phthalide, 3,3 - bis(methylindol - 3yl)phthalides such as 3,3 - bis(l,2- dimethyl- indol - 3 - yl)phthalide, 3 - (phenyl) - 3 (heterocyclic - substituted)phthalides such as 3 - (p - dimethylaminophenyl) - 3 - (1- methylpyrr - 2 - yl) - 6 - dimethylaminophthalide, indole and carbazole-substituted phthalides such as 3,3 - bis( 1,2 - dimethylindol - 3 - yl) - 5 - dimethylaminophthalide and 3,3 - bis(9 - ethylcarbazol - 3 - yl)5 - dimethylaminophthalide, and substituted indole phthalides such as 3 - (1,2 - dimethylindol - 3 - yl) - 3 - (2 - methylindol - 3 yl ) phthalide.
Other chromogens useful in the practice of this invention include indole-substituted pyromellitides, for instance 3,5 - bis - (p - diethylaminophenyl) - 3,5 - bis( 1,2 - dimethylindol3 - yl)pyromellitide, 3,7 - bis - (p - diethylaminophenyl) - 3,7 - bis - (1,2 - dimethylindol - 3 - yl)pyromellitide, 3,3,7,7 - tetrakis1,2 - dimethylindol - 3 - yl)pyromellitide and 3,3,5,5 - tetrakis - (1,2 - dimethylindol- 3yl)pyromellitide; and leucauramines and substituted leucauramines such as for instance pxylyl-leucauramine and phenyl-leucauramine.
Also included are orthohydroxybenzoacetophenone, 2,4 - bis[p - (p - dimethylamino- phenylazo)anilinej - 6 - hydroxyl - sym-triazine, N,3,3 - trimethylindolinobenzospiropyrans, and N,3,3 - trimethylindolino - p- naphthospiropiranes.
An auxiliary coloring agent can be employed with the above chromogens to provide fade resistance where fading is a problem. Many phthalide compounds such as crystal violet lactone for example, are characterized by rapid color development with a normal tendency to fade during the course of time. One suitable auxiliary coloring agent is benzoyl leuco methylene blue which oxidizes when released on the paper to slowly form a permanent blue colour. The combination of a phthalide chromogen and such a colorless oxidizable auxiliary coloring agent provides a composition having both rapid color development and fade resistance.
The mark-recording system of the present invention can be prepared according to well known conventional procedures. Descriptions of methods for preparing both the dyecarrying paper and coated receiving paper are to be found in the literature.
Although a preferred embodiment of this invention comprises a two-sheet system wherein the sensitizing agent, for example the acid clay, is carried by one sheet and a marking fluid comprising a chromogen and solvent is carried by a second sheet, the invention is not limited to such systems alone. The only essential requirement is that the chromogen and the sensitizing agent be maintained in a separate or unreactive condition until pressure is applied to the system and that upon the application of pressure the chromogen and sensitizing agent are brought into reactive content.Thus it is possible to have the chromogen and sensitizing agent present in a dry and unreactive state on a common carrier and to have the solvent alone carried on a separate sheet whereupon the application of pressure would release the solvent into the chromogen-acidic material mixture and promote localized reaction and colour development. Obviously, many other arrangements, configurations and relationships of the solvent and the mark forming materials with respect to their encapsulation and location on the supporting sheet or webs can be envisaged, and such arrangements are within the scope of the present invention. For example, it is possible to coat a single paper or support member with all the components of this system to form a single self-contained unit which can be marked by the movement of a stylus or other pressure-imparting means upon the surface of the pauper.Such papers are particularly useful for use in inkless recording instruments.
The invention is illustrated by the following
Example.
EXAMPLE.
A series of solvents each consisting of a mixture of equal parts by weight of kerosene and a "main solvent" was prepared. The "main solvent" was a mixture of dibenzyl ether (DBE) and partially hydrogenated terphenyls (PHT) produced by the hydrogenation of terphenyl using approximately 30% of the amount of hydrogen which would be required for full hydrogenation in the proportions shown in the Table below. Crystal violet lactone was dissolved in a sample of each solvent to give a solution containing 1.5% by weight of crystal violet lactone.
The effect of the varying proportions of dibenzyl ether on print intensity was assessed by a laboratory procedure as follows:
A thin and even layer of the solution was
applied onto an acid clay coated sheet (C.F.
receiver sheet) by means of a rubber stamp.
This operation was carried out several times
on the same receiver sheet, in order to transfer.
a weighable amount of solution.
The prints obtained in this manner were
allowed to develop until they reached their
maximum intensity. (About 2 hours).
The print intensities were measured at
several points on the surface by means of a
MacBeth digital reflectometer, averaged, and
related to 1 mg of dye(s) + solvent solution transferred per unit area of receiver sheet.
The final figure which can thereby be associated with each solvent enables to rank it with respect to its "efficiency".
The results were as follows:
Composition of the Main Solvent PHT DBE Efficiency 100% 0% .38 99% 1% .40 97% 3% .43 92.5% 7.5% .45 90% 10% .46 80% 20% .46 75% 25% .47 66.6% 33.3NO .47 50% 50% .46 0% 100% f .46 The results show the marked improvement in efficiency obtained by the addition of not more than 10 or 15% by weight of dibenzyl ether to the hydrogenated terphenyls.
WHAT WE CLAIM IS:
1. A solvent comprising a mixture of a hydrogenated terphenyl and a di(arylalkyl)ether of the formula:
wherein each R represents hydrogen, an alkyl group or a cycloalkyl group, each R' represents an alkyl group or a halogen atom, each n is an integer of from 1 to 6, each m is 0 or an integer of from 1 to 3, and each
Rmt(A) represents an aryl group when m is 0 or an alkyl- and/or halogen-substituted aryl group when m is a said integer.
2. A solvent according to Claim 1 in which the proportion by weight ot the di(arylalkyl)
ether in the mixture is not more than 15%.
3. A solvent according to either of Claims
1 and 2 in which the hydrogenated terphenyl
is a product obtained by the partial hydro
genation of terphenyl, and which contains
hexahydroterphenyls, dodecahydroterphenyls and residual terphenyl.
4. A solvent according to any of Claims 1 to 3 wherein the di(arylalkyl)ether is one wherein each R represents hydrogen or an alkyl group of from 1 to 6 carbon atoms, each
R' represents an alkyl group of from 1 to 4 carbon atoms and each m is 0 or has a value such that the total number of carbon atoms in Rrn' does not exceed 6, each Rm'( Ar)- represents an unsubstituted or alkyl-substituted
phenyl, naphthyl or biphenyl group, and each
n has a value such that the total number of
carbon atoms in the two
groups does not exceed the total number of carbon atoms in the two Ar nuclei.
5. A solvent according to Claim 4 wherein the di(arylalkyl)ether is one wherein each R represents hydrogen or a methyl group and each n has the value 1 or 2.
6. A solvent according to Claim 15 wherein the di(arylalkyl)ether is dibenzyl ether, benzyl a-methylbenzyl ether, di(a-methylbenzyl ) ether or benzyl a-naphthylmethyl ether.
7. A solvent according to any of Claims
1 to 6, in which the proportion by weight of
**WARNING** end of DESC field may overlap start of CLMS **.
Claims (16)
1. A solvent comprising a mixture of a hydrogenated terphenyl and a di(arylalkyl)ether of the formula:
wherein each R represents hydrogen, an alkyl group or a cycloalkyl group, each R' represents an alkyl group or a halogen atom, each n is an integer of from 1 to 6, each m is 0 or an integer of from 1 to 3, and each
Rmt(A) represents an aryl group when m is 0 or an alkyl- and/or halogen-substituted aryl group when m is a said integer.
2. A solvent according to Claim 1 in which the proportion by weight ot the di(arylalkyl)
ether in the mixture is not more than 15%.
3. A solvent according to either of Claims
1 and 2 in which the hydrogenated terphenyl
is a product obtained by the partial hydro
genation of terphenyl, and which contains
hexahydroterphenyls, dodecahydroterphenyls and residual terphenyl.
4. A solvent according to any of Claims 1 to 3 wherein the di(arylalkyl)ether is one wherein each R represents hydrogen or an alkyl group of from 1 to 6 carbon atoms, each
R' represents an alkyl group of from 1 to 4 carbon atoms and each m is 0 or has a value such that the total number of carbon atoms in Rrn' does not exceed 6, each Rm'( Ar)- represents an unsubstituted or alkyl-substituted
phenyl, naphthyl or biphenyl group, and each
n has a value such that the total number of
carbon atoms in the two
groups does not exceed the total number of carbon atoms in the two Ar nuclei.
5. A solvent according to Claim 4 wherein the di(arylalkyl)ether is one wherein each R represents hydrogen or a methyl group and each n has the value 1 or 2.
6. A solvent according to Claim 15 wherein the di(arylalkyl)ether is dibenzyl ether, benzyl a-methylbenzyl ether, di(a-methylbenzyl ) ether or benzyl a-naphthylmethyl ether.
7. A solvent according to any of Claims
1 to 6, in which the proportion by weight of
the di(arylalkyl)ether in the mixture is from 1% to 10%.
8. A solvent according to any of Claims 1 to 7 which is a mixture of the hydrogenated terphenyl and di ( arylalkyl ) ether or is a combination of such a mixture with not more than 3 parts by weight of an inert liquid diluent per part by weight of the mixture.
9. A solvent according to Claim 8 in which the diluent is a mineral or vegetable oil or an alkylated benzene.
10. A solution, in a solvent according to any of Claims 1 to 9, of a chromogen suitable for use in a carbonless copying paper system.
11. A solution according to Claim 10 in which the chromogen is a phthalide compound.
12. A pressure-sensitive mark-recording system comprising (a) sheet material, (b) mark-forming components supported by the sheet material and arranged in juxtaposition but in unreactive condition, the said components comprising a chromogen and a sensitizer for the chromogen to produce a colour when brought into contact with the chromogen in the presence of a solvent for the chromogen, and (c) a solvent according to any of Claims 1 to 9 supported by the sheet material but separated from the sensitizing agent by a physical barrier which is rupturable on the application of a marking instrument to the sheet material.
13. A pressure-sensitive mark-recording system according to Claim 12 in which the sensitizer for the chromogen is an acid clay.
14. A pressure sensitive mark-recording system according to Claim 13 wherein the chromogen is dissolved in the solvent, and the solvent is a solvent according to Claim 2.
15. A solvent according to Claim 1 substantially as described in the Example.
16. A solution according to Claim 10 substantially as described in the Example.
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB5094376A GB1564931A (en) | 1976-12-07 | 1976-12-07 | Dye solvents |
| DE19772753816 DE2753816C3 (en) | 1976-12-07 | 1977-12-02 | Solvent mixture and its use in copier papers |
| BE183179A BE861512A (en) | 1976-12-07 | 1977-12-05 | DYE SOLVENTS FOR THE PREPARATION OF CARBON-FREE COPIING PAPERS |
| AU31209/77A AU514639B2 (en) | 1976-12-07 | 1977-12-05 | Dye solvents |
| ES464808A ES464808A1 (en) | 1976-12-07 | 1977-12-06 | Dye solvents |
| FR7736665A FR2373590A1 (en) | 1976-12-07 | 1977-12-06 | DYE SOLVENTS FOR THE PREPARATION OF CARBON-FREE COPIING PAPERS |
| JP14579177A JPS5371914A (en) | 1976-12-07 | 1977-12-06 | Dye solvent |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB5094376A GB1564931A (en) | 1976-12-07 | 1976-12-07 | Dye solvents |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1564931A true GB1564931A (en) | 1980-04-16 |
Family
ID=10458035
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB5094376A Expired GB1564931A (en) | 1976-12-07 | 1976-12-07 | Dye solvents |
Country Status (7)
| Country | Link |
|---|---|
| JP (1) | JPS5371914A (en) |
| AU (1) | AU514639B2 (en) |
| BE (1) | BE861512A (en) |
| DE (1) | DE2753816C3 (en) |
| ES (1) | ES464808A1 (en) |
| FR (1) | FR2373590A1 (en) |
| GB (1) | GB1564931A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0057740A1 (en) * | 1981-02-09 | 1982-08-18 | Diamond Shamrock Corporation | Pressure sensitive recording sheets |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4822418A (en) * | 1981-03-27 | 1989-04-18 | Dataproducts Corporation | Drop on demand ink jet ink comprising dubutyl sebecate |
| US4793264A (en) * | 1981-12-07 | 1988-12-27 | Dataproducts Corporation | Low corrosion impulse ink jet ink containing anti-oxidant |
| US4659383A (en) * | 1981-12-17 | 1987-04-21 | Exxon Printing Systems, Inc. | High molecular weight, hot melt impulse ink jet ink |
| US4484948A (en) * | 1981-12-17 | 1984-11-27 | Exxon Research And Engineering Co. | Natural wax-containing ink jet inks |
| US4758276A (en) * | 1981-12-17 | 1988-07-19 | Dataproducts Corporation | Stearic acid-containing ink jet inks |
| US5350446A (en) * | 1984-11-05 | 1994-09-27 | Dataproducts Corporation | Hot melt impulse ink jet ink with dispersed solid pigment in a hot melt vehicle |
| JPS6475283A (en) * | 1987-09-17 | 1989-03-20 | Nippon Kokan Kk | Solvent for pressure-sensitive copying paper |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1371807A (en) * | 1970-10-27 | 1974-10-30 | Fuji Photo Film Co Ltd | Pressure-sensitive recording material |
| DE2342758A1 (en) * | 1973-08-24 | 1975-04-10 | Pelikan Werke Wagner Guenther | Colour reaction system with metal carboxylate or sulphonate - as developer using org ether cpd as solvent for colour former |
| JPS5321328B2 (en) * | 1973-10-31 | 1978-07-01 |
-
1976
- 1976-12-07 GB GB5094376A patent/GB1564931A/en not_active Expired
-
1977
- 1977-12-02 DE DE19772753816 patent/DE2753816C3/en not_active Expired
- 1977-12-05 BE BE183179A patent/BE861512A/en not_active IP Right Cessation
- 1977-12-05 AU AU31209/77A patent/AU514639B2/en not_active Expired
- 1977-12-06 ES ES464808A patent/ES464808A1/en not_active Expired
- 1977-12-06 FR FR7736665A patent/FR2373590A1/en active Granted
- 1977-12-06 JP JP14579177A patent/JPS5371914A/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0057740A1 (en) * | 1981-02-09 | 1982-08-18 | Diamond Shamrock Corporation | Pressure sensitive recording sheets |
Also Published As
| Publication number | Publication date |
|---|---|
| DE2753816A1 (en) | 1978-06-08 |
| FR2373590A1 (en) | 1978-07-07 |
| DE2753816B2 (en) | 1980-04-24 |
| DE2753816C3 (en) | 1980-12-11 |
| AU3120977A (en) | 1979-06-14 |
| JPS5371914A (en) | 1978-06-26 |
| FR2373590B1 (en) | 1981-01-09 |
| ES464808A1 (en) | 1978-09-01 |
| BE861512A (en) | 1978-06-05 |
| AU514639B2 (en) | 1981-02-19 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |
Effective date: 19921117 |