DE69515807T2 - Neue, Terpenderivat- oder Abietinsäurederivatlösungsmittel enthaltende Mikrokapseln, hauptsächlich für chemische Kopierpapiere und mit diesen Mikrokapseln verschichtete druckempfindliche Papiere - Google Patents
Neue, Terpenderivat- oder Abietinsäurederivatlösungsmittel enthaltende Mikrokapseln, hauptsächlich für chemische Kopierpapiere und mit diesen Mikrokapseln verschichtete druckempfindliche PapiereInfo
- Publication number
- DE69515807T2 DE69515807T2 DE1995615807 DE69515807T DE69515807T2 DE 69515807 T2 DE69515807 T2 DE 69515807T2 DE 1995615807 DE1995615807 DE 1995615807 DE 69515807 T DE69515807 T DE 69515807T DE 69515807 T2 DE69515807 T2 DE 69515807T2
- Authority
- DE
- Germany
- Prior art keywords
- terpene
- abietic acid
- derivatives
- microcapsules
- esters
- 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 - Fee Related
Links
- 239000003094 microcapsule Substances 0.000 title claims description 53
- 235000007586 terpenes Nutrition 0.000 title claims description 52
- BTXXTMOWISPQSJ-UHFFFAOYSA-N 4,4,4-trifluorobutan-2-one Chemical class CC(=O)CC(F)(F)F BTXXTMOWISPQSJ-UHFFFAOYSA-N 0.000 title claims description 49
- 239000002904 solvent Substances 0.000 title claims description 33
- 150000003505 terpenes Chemical class 0.000 title claims description 25
- 239000000126 substance Substances 0.000 title description 3
- -1 terpene alcohols Chemical class 0.000 claims description 52
- 239000000203 mixture Substances 0.000 claims description 33
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 claims description 26
- BQACOLQNOUYJCE-FYZZASKESA-N Abietic acid Natural products CC(C)C1=CC2=CC[C@]3(C)[C@](C)(CCC[C@@]3(C)C(=O)O)[C@H]2CC1 BQACOLQNOUYJCE-FYZZASKESA-N 0.000 claims description 25
- 235000015112 vegetable and seed oil Nutrition 0.000 claims description 21
- 239000008158 vegetable oil Substances 0.000 claims description 21
- 239000003795 chemical substances by application Substances 0.000 claims description 17
- 239000003921 oil Substances 0.000 claims description 17
- 235000019198 oils Nutrition 0.000 claims description 17
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 15
- 239000000194 fatty acid Substances 0.000 claims description 15
- 229930195729 fatty acid Natural products 0.000 claims description 15
- 150000002148 esters Chemical class 0.000 claims description 14
- 239000002480 mineral oil Substances 0.000 claims description 14
- 229930004725 sesquiterpene Natural products 0.000 claims description 11
- 150000004354 sesquiterpene derivatives Chemical class 0.000 claims description 11
- 235000010446 mineral oil Nutrition 0.000 claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 8
- 230000002209 hydrophobic effect Effects 0.000 claims description 8
- 239000003153 chemical reaction reagent Substances 0.000 claims description 7
- IRAQOCYXUMOFCW-OSFYFWSMSA-N cedr-8-ene Chemical compound C1[C@]23[C@H](C)CC[C@H]3C(C)(C)[C@@H]1C(C)=CC2 IRAQOCYXUMOFCW-OSFYFWSMSA-N 0.000 claims description 6
- 238000006116 polymerization reaction Methods 0.000 claims description 6
- WUOACPNHFRMFPN-SECBINFHSA-N (S)-(-)-alpha-terpineol Chemical compound CC1=CC[C@@H](C(C)(C)O)CC1 WUOACPNHFRMFPN-SECBINFHSA-N 0.000 claims description 5
- OVKDFILSBMEKLT-UHFFFAOYSA-N alpha-Terpineol Natural products CC(=C)C1(O)CCC(C)=CC1 OVKDFILSBMEKLT-UHFFFAOYSA-N 0.000 claims description 5
- RUJPNZNXGCHGID-UHFFFAOYSA-N (Z)-beta-Terpineol Natural products CC(=C)C1CCC(C)(O)CC1 RUJPNZNXGCHGID-UHFFFAOYSA-N 0.000 claims description 4
- 240000002791 Brassica napus Species 0.000 claims description 4
- 235000004977 Brassica sinapistrum Nutrition 0.000 claims description 4
- 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 claims description 4
- 229940088601 alpha-terpineol Drugs 0.000 claims description 4
- UODXCYZDMHPIJE-UHFFFAOYSA-N menthanol Chemical compound CC1CCC(C(C)(C)O)CC1 UODXCYZDMHPIJE-UHFFFAOYSA-N 0.000 claims description 4
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 claims description 4
- QJVXKWHHAMZTBY-GCPOEHJPSA-N syringin Chemical compound COC1=CC(\C=C\CO)=CC(OC)=C1O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 QJVXKWHHAMZTBY-GCPOEHJPSA-N 0.000 claims description 4
- 238000005809 transesterification reaction Methods 0.000 claims description 4
- NPNUFJAVOOONJE-ZIAGYGMSSA-N β-(E)-Caryophyllene Chemical compound C1CC(C)=CCCC(=C)[C@H]2CC(C)(C)[C@@H]21 NPNUFJAVOOONJE-ZIAGYGMSSA-N 0.000 claims description 4
- JQCVPZXMGXKNOD-UHFFFAOYSA-N 1,2-dibenzylbenzene Chemical class C=1C=CC=C(CC=2C=CC=CC=2)C=1CC1=CC=CC=C1 JQCVPZXMGXKNOD-UHFFFAOYSA-N 0.000 claims description 3
- AWNOGHRWORTNEI-UHFFFAOYSA-N 2-(6,6-dimethyl-4-bicyclo[3.1.1]hept-3-enyl)ethyl acetate Chemical compound CC(=O)OCCC1=CCC2C(C)(C)C1C2 AWNOGHRWORTNEI-UHFFFAOYSA-N 0.000 claims description 3
- UZZYXZWSOWQPIS-UHFFFAOYSA-N 3-fluoro-5-(trifluoromethyl)benzaldehyde Chemical compound FC1=CC(C=O)=CC(C(F)(F)F)=C1 UZZYXZWSOWQPIS-UHFFFAOYSA-N 0.000 claims description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 3
- 244000105624 Arachis hypogaea Species 0.000 claims description 3
- 244000068988 Glycine max Species 0.000 claims description 3
- 235000010469 Glycine max Nutrition 0.000 claims description 3
- 244000020551 Helianthus annuus Species 0.000 claims description 3
- 235000003222 Helianthus annuus Nutrition 0.000 claims description 3
- PDSNLYSELAIEBU-UHFFFAOYSA-N Longifolene Chemical compound C1CCC(C)(C)C2C3CCC2C1(C)C3=C PDSNLYSELAIEBU-UHFFFAOYSA-N 0.000 claims description 3
- ZPUKHRHPJKNORC-UHFFFAOYSA-N Longifolene Natural products CC1(C)CCCC2(C)C3CCC1(C3)C2=C ZPUKHRHPJKNORC-UHFFFAOYSA-N 0.000 claims description 3
- 240000007817 Olea europaea Species 0.000 claims description 3
- 235000004443 Ricinus communis Nutrition 0.000 claims description 3
- 244000000231 Sesamum indicum Species 0.000 claims description 3
- 235000003434 Sesamum indicum Nutrition 0.000 claims description 3
- 244000044822 Simmondsia californica Species 0.000 claims description 3
- 235000004433 Simmondsia californica Nutrition 0.000 claims description 3
- 240000008042 Zea mays Species 0.000 claims description 3
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 claims description 3
- 235000002017 Zea mays subsp mays Nutrition 0.000 claims description 3
- 150000004996 alkyl benzenes Chemical class 0.000 claims description 3
- 235000005822 corn Nutrition 0.000 claims description 3
- IRAQOCYXUMOFCW-UHFFFAOYSA-N di-epi-alpha-cedrene Natural products C1C23C(C)CCC3C(C)(C)C1C(C)=CC2 IRAQOCYXUMOFCW-UHFFFAOYSA-N 0.000 claims description 3
- DUNCVNHORHNONW-UHFFFAOYSA-N myrcenol Chemical compound CC(C)(O)CCCC(=C)C=C DUNCVNHORHNONW-UHFFFAOYSA-N 0.000 claims description 3
- 229930008383 myrcenol Natural products 0.000 claims description 3
- 235000020232 peanut Nutrition 0.000 claims description 3
- 229920006395 saturated elastomer Polymers 0.000 claims description 3
- 150000001911 terphenyls Chemical class 0.000 claims description 3
- FAMPSKZZVDUYOS-OWEBEESNSA-N (1e,4z,8e)-2,6,6,9-tetramethylcycloundeca-1,4,8-triene Chemical compound C\C1=C/CC(C)(C)\C=C/C\C(C)=C\CC1 FAMPSKZZVDUYOS-OWEBEESNSA-N 0.000 claims description 2
- WRFXXJKURVTLSY-UHFFFAOYSA-N 2,6-dimethyloctan-2-ol Chemical compound CCC(C)CCCC(C)(C)O WRFXXJKURVTLSY-UHFFFAOYSA-N 0.000 claims description 2
- 235000017060 Arachis glabrata Nutrition 0.000 claims description 2
- 235000010777 Arachis hypogaea Nutrition 0.000 claims description 2
- 235000018262 Arachis monticola Nutrition 0.000 claims description 2
- 240000007124 Brassica oleracea Species 0.000 claims description 2
- 235000003899 Brassica oleracea var acephala Nutrition 0.000 claims description 2
- 240000006240 Linum usitatissimum Species 0.000 claims description 2
- 235000004431 Linum usitatissimum Nutrition 0.000 claims description 2
- FAMPSKZZVDUYOS-UHFFFAOYSA-N alpha-Caryophyllene Natural products CC1=CCC(C)(C)C=CCC(C)=CCC1 FAMPSKZZVDUYOS-UHFFFAOYSA-N 0.000 claims description 2
- NPNUFJAVOOONJE-UHFFFAOYSA-N beta-cariophyllene Natural products C1CC(C)=CCCC(=C)C2CC(C)(C)C21 NPNUFJAVOOONJE-UHFFFAOYSA-N 0.000 claims description 2
- 239000003139 biocide Substances 0.000 claims description 2
- NPNUFJAVOOONJE-UONOGXRCSA-N caryophyllene Natural products C1CC(C)=CCCC(=C)[C@@H]2CC(C)(C)[C@@H]21 NPNUFJAVOOONJE-UONOGXRCSA-N 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 claims description 2
- 239000000975 dye Substances 0.000 claims description 2
- 239000000796 flavoring agent Substances 0.000 claims description 2
- 235000019634 flavors Nutrition 0.000 claims description 2
- 235000004426 flaxseed Nutrition 0.000 claims description 2
- FWQHNLCNFPYBCA-UHFFFAOYSA-N fluoran Chemical class C12=CC=CC=C2OC2=CC=CC=C2C11OC(=O)C2=CC=CC=C21 FWQHNLCNFPYBCA-UHFFFAOYSA-N 0.000 claims description 2
- 235000013305 food Nutrition 0.000 claims description 2
- 239000000417 fungicide Substances 0.000 claims description 2
- 239000004009 herbicide Substances 0.000 claims description 2
- QBNFBHXQESNSNP-UHFFFAOYSA-N humulene Natural products CC1=CC=CC(C)(C)CC=C(/C)CCC1 QBNFBHXQESNSNP-UHFFFAOYSA-N 0.000 claims description 2
- 239000000575 pesticide Substances 0.000 claims description 2
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 2
- 229940127557 pharmaceutical product Drugs 0.000 claims description 2
- XHXUANMFYXWVNG-UHFFFAOYSA-N (+/-)-Menthyl acetate Chemical compound CC(C)C1CCC(C)CC1OC(C)=O XHXUANMFYXWVNG-UHFFFAOYSA-N 0.000 claims 1
- XOEUNIAGBKGZLU-UHFFFAOYSA-N 3,3-bis(2-methyl-1-octylindol-3-yl)-2-benzofuran-1-one Chemical compound C1=CC=C2C(C3(C4=CC=CC=C4C(=O)O3)C3=C(C)N(C4=CC=CC=C43)CCCCCCCC)=C(C)N(CCCCCCCC)C2=C1 XOEUNIAGBKGZLU-UHFFFAOYSA-N 0.000 claims 1
- 241001133760 Acoelorraphe Species 0.000 claims 1
- 235000011301 Brassica oleracea var capitata Nutrition 0.000 claims 1
- 235000001169 Brassica oleracea var oleracea Nutrition 0.000 claims 1
- 125000001931 aliphatic group Chemical group 0.000 claims 1
- 239000003205 fragrance Substances 0.000 claims 1
- 238000005984 hydrogenation reaction Methods 0.000 claims 1
- WUOACPNHFRMFPN-UHFFFAOYSA-N alpha-terpineol Chemical compound CC1=CCC(C(C)(C)O)CC1 WUOACPNHFRMFPN-UHFFFAOYSA-N 0.000 description 26
- SQIFACVGCPWBQZ-UHFFFAOYSA-N delta-terpineol Natural products CC(C)(O)C1CCC(=C)CC1 SQIFACVGCPWBQZ-UHFFFAOYSA-N 0.000 description 26
- 229940116411 terpineol Drugs 0.000 description 26
- 239000000243 solution Substances 0.000 description 13
- 239000011248 coating agent Substances 0.000 description 9
- 238000000576 coating method Methods 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- 239000000839 emulsion Substances 0.000 description 7
- 229920000159 gelatin Polymers 0.000 description 7
- 235000019322 gelatine Nutrition 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 150000004665 fatty acids Chemical class 0.000 description 6
- 239000012071 phase Substances 0.000 description 6
- 230000008569 process Effects 0.000 description 6
- 108010010803 Gelatin Proteins 0.000 description 5
- 238000005538 encapsulation Methods 0.000 description 5
- 239000008273 gelatin Substances 0.000 description 5
- 235000011852 gelatine desserts Nutrition 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- ROKSAUSPJGWCSM-UHFFFAOYSA-N 2-(7,7-dimethyl-4-bicyclo[3.1.1]hept-3-enyl)ethanol Chemical compound C1C2C(C)(C)C1CC=C2CCO ROKSAUSPJGWCSM-UHFFFAOYSA-N 0.000 description 4
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 230000032683 aging Effects 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000000084 colloidal system Substances 0.000 description 4
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 4
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 4
- 150000004702 methyl esters Chemical class 0.000 description 4
- 230000003287 optical effect Effects 0.000 description 4
- 239000002245 particle Substances 0.000 description 4
- WNZQDUSMALZDQF-UHFFFAOYSA-N 2-benzofuran-1(3H)-one Chemical class C1=CC=C2C(=O)OCC2=C1 WNZQDUSMALZDQF-UHFFFAOYSA-N 0.000 description 3
- LWLRMRFJCCMNML-UHFFFAOYSA-N 2-ethylhexyl dodecanoate Chemical compound CCCCCCCCCCCC(=O)OCC(CC)CCCC LWLRMRFJCCMNML-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
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- 125000000129 anionic group Chemical group 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
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- OVXRPXGVKBHGQO-UYWIDEMCSA-N methyl (1r,4ar,4br,10ar)-1,4a-dimethyl-7-propan-2-yl-2,3,4,4b,5,6,10,10a-octahydrophenanthrene-1-carboxylate Chemical compound C1CC(C(C)C)=CC2=CC[C@H]3[C@@](C(=O)OC)(C)CCC[C@]3(C)[C@H]21 OVXRPXGVKBHGQO-UYWIDEMCSA-N 0.000 description 3
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- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
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- PHYFQTYBJUILEZ-UHFFFAOYSA-N Trioleoylglycerol Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC(OC(=O)CCCCCCCC=CCCCCCCCC)COC(=O)CCCCCCCC=CCCCCCCCC PHYFQTYBJUILEZ-UHFFFAOYSA-N 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000009172 bursting Effects 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- OIDPCXKPHYRNKH-UHFFFAOYSA-J chrome alum Chemical compound [K]OS(=O)(=O)O[Cr]1OS(=O)(=O)O1 OIDPCXKPHYRNKH-UHFFFAOYSA-J 0.000 description 1
- 235000020971 citrus fruits Nutrition 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 238000005354 coacervation Methods 0.000 description 1
- 239000008199 coating composition Substances 0.000 description 1
- 229940071160 cocoate Drugs 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- PHMQYKDOTWAOBI-UHFFFAOYSA-N decanoic acid;propane-1,2-diol Chemical compound CC(O)CO.CCCCCCCCCC(O)=O PHMQYKDOTWAOBI-UHFFFAOYSA-N 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- XSNQECSCDATQEL-UHFFFAOYSA-N dihydromyrcenol Chemical compound C=CC(C)CCCC(C)(C)O XSNQECSCDATQEL-UHFFFAOYSA-N 0.000 description 1
- 229930008394 dihydromyrcenol Natural products 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 229930004069 diterpene Natural products 0.000 description 1
- 125000000567 diterpene group Chemical group 0.000 description 1
- QYDYPVFESGNLHU-UHFFFAOYSA-N elaidic acid methyl ester Natural products CCCCCCCCC=CCCCCCCCC(=O)OC QYDYPVFESGNLHU-UHFFFAOYSA-N 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- MFGZXPGKKJMZIY-UHFFFAOYSA-N ethyl 5-amino-1-(4-sulfamoylphenyl)pyrazole-4-carboxylate Chemical compound NC1=C(C(=O)OCC)C=NN1C1=CC=C(S(N)(=O)=O)C=C1 MFGZXPGKKJMZIY-UHFFFAOYSA-N 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 230000008570 general process Effects 0.000 description 1
- 229940113087 geraniol Drugs 0.000 description 1
- 244000048394 giant Jersey kale Species 0.000 description 1
- 238000001033 granulometry Methods 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000002427 irreversible effect Effects 0.000 description 1
- XUGNVMKQXJXZCD-UHFFFAOYSA-N isopropyl palmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC(C)C XUGNVMKQXJXZCD-UHFFFAOYSA-N 0.000 description 1
- 229920000126 latex Polymers 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- QYDYPVFESGNLHU-KHPPLWFESA-N methyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC QYDYPVFESGNLHU-KHPPLWFESA-N 0.000 description 1
- 229940073769 methyl oleate Drugs 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- WASNIKZYIWZQIP-AWEZNQCLSA-N nerolidol Natural products CC(=CCCC(=CCC[C@@H](O)C=C)C)C WASNIKZYIWZQIP-AWEZNQCLSA-N 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 231100000956 nontoxicity Toxicity 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
- 239000002304 perfume Substances 0.000 description 1
- 239000010665 pine oil Substances 0.000 description 1
- 239000001739 pinus spp. Substances 0.000 description 1
- 229920001495 poly(sodium acrylate) polymer Polymers 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- NNMHYFLPFNGQFZ-UHFFFAOYSA-M sodium polyacrylate Chemical compound [Na+].[O-]C(=O)C=C NNMHYFLPFNGQFZ-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000003784 tall oil Substances 0.000 description 1
- TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 description 1
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 1
- 150000003626 triacylglycerols Chemical class 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
- 229940036248 turpentine Drugs 0.000 description 1
- 239000002023 wood Substances 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)
- Manufacturing Of Micro-Capsules (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9414545A FR2727633A1 (fr) | 1994-12-02 | 1994-12-02 | Microcapsules contenant a titre de solvant un derive terpenique ou d'acide abietique et papiers sensibles a la pression revetus de ces microcapsules |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69515807D1 DE69515807D1 (de) | 2000-04-27 |
| DE69515807T2 true DE69515807T2 (de) | 2000-12-07 |
Family
ID=9469441
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1995615807 Expired - Fee Related DE69515807T2 (de) | 1994-12-02 | 1995-12-01 | Neue, Terpenderivat- oder Abietinsäurederivatlösungsmittel enthaltende Mikrokapseln, hauptsächlich für chemische Kopierpapiere und mit diesen Mikrokapseln verschichtete druckempfindliche Papiere |
Country Status (3)
| Country | Link |
|---|---|
| EP (1) | EP0714786B1 (enrdf_load_stackoverflow) |
| DE (1) | DE69515807T2 (enrdf_load_stackoverflow) |
| FR (1) | FR2727633A1 (enrdf_load_stackoverflow) |
Family Cites Families (31)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2712507A (en) | 1953-06-30 | 1955-07-05 | Ncr Co | Pressure sensitive record material |
| US2730457A (en) | 1953-06-30 | 1956-01-10 | Ncr Co | Pressure responsive record materials |
| US3016308A (en) | 1957-08-06 | 1962-01-09 | Moore Business Forms Inc | Recording paper coated with microscopic capsules of coloring material, capsules and method of making |
| FR1349561A (fr) * | 1962-01-29 | 1964-01-17 | Minnesota Mining & Mfg | Feuilles contenant des capsules |
| FR1571089A (enrdf_load_stackoverflow) * | 1968-08-05 | 1969-06-13 | ||
| US4063754A (en) * | 1976-05-07 | 1977-12-20 | The Mead Corporation | Process for the production of pressure sensitive carbonless record sheets using novel hot melt systems and products thereof |
| US4342473A (en) * | 1978-06-26 | 1982-08-03 | Champion International Corporation | Pressure-sensitive copy systems containing phenolic ester as color-stabilizers |
| GB2058111B (en) | 1979-06-08 | 1983-08-03 | Kanzaki Paper Mfg Co Ltd | Microcapsule dispersions |
| DE2940786A1 (de) | 1979-10-08 | 1981-04-16 | Basf Ag, 6700 Ludwigshafen | Verfahren zur herstellung von mikrokapseln |
| DE3016170A1 (de) | 1980-04-26 | 1981-10-29 | Bayer Ag, 5090 Leverkusen | Mikrokapseln mit definierter oeffnungstemperatur, verfahren zu deren herstellung sowie deren verwendung |
| JPS57133093A (en) | 1981-02-12 | 1982-08-17 | Jujo Paper Co Ltd | Developing sheet for pressure sensitive copying paper |
| JPS58138689A (ja) | 1982-02-13 | 1983-08-17 | Mitsubishi Paper Mills Ltd | 感圧記録系 |
| US4444699A (en) | 1982-04-20 | 1984-04-24 | Appleton Papers Inc. | Capsule manufacture |
| JPS59155092A (ja) | 1983-02-23 | 1984-09-04 | Fuji Photo Film Co Ltd | 顕色剤シ−トの製造方法 |
| JPS60107384A (ja) | 1983-11-16 | 1985-06-12 | Fuji Photo Film Co Ltd | 感圧記録シ−ト |
| US4629800A (en) | 1984-03-09 | 1986-12-16 | Kanzaki Paper Manufacturing Co., Ltd. | Fluoran compounds |
| DE3421865A1 (de) | 1984-06-13 | 1985-12-19 | Bayer Ag, 5090 Leverkusen | Kontinuierliche herstellung von mikrokapseldispersionen |
| GB8511202D0 (en) | 1985-05-02 | 1985-06-12 | Wiggins Teape Group Ltd | Record material |
| DE3532878A1 (de) | 1985-09-14 | 1987-03-26 | Basf Ag | Kontinuierliches verfahren zur herstellung von mikrokapseln mit waenden aus melamin-formaldehydkondensaten in waessriger dispersion |
| US4898780A (en) | 1985-11-08 | 1990-02-06 | The Standard Register Company | Production of microcapsules |
| FR2591124B1 (fr) | 1985-12-10 | 1988-02-12 | Rhone Poulenc Spec Chim | Procede de microencapsulation par polyaddition-interfaciale. |
| DE3605552A1 (de) | 1986-02-21 | 1987-08-27 | Bayer Ag | Hochkonzentrierte, stabile loesungen von farbbildnern |
| DE3633116A1 (de) | 1986-09-30 | 1988-04-07 | Feldmuehle Ag | Druckempfindliches aufzeichnungsmaterial |
| CA1329035C (en) | 1987-12-03 | 1994-05-03 | Joseph Gerald O'connor | Method for producing amine-formaldehyde microcapsules and photosensitive microcapsules produced thereby |
| US4785048A (en) | 1988-02-08 | 1988-11-15 | Moore Business Forms, Inc. | Polyurea and polyurea-epoxy microcapsules |
| GB8809648D0 (en) | 1988-04-23 | 1988-05-25 | Wiggins Teape Group Ltd | Production of microcapsules |
| JP2632004B2 (ja) | 1988-06-15 | 1997-07-16 | 富士写真フイルム株式会社 | 感圧記録シート用マイクロカプセルの製造法 |
| DE4006570C1 (enrdf_load_stackoverflow) | 1990-03-02 | 1991-05-23 | Papierfabrik August Koehler Ag, 7602 Oberkirch, De | |
| US5236780A (en) * | 1990-03-16 | 1993-08-17 | Brother Kogyo Kabushiki Kaisha | Image-retransferable sheet |
| FR2692480B1 (fr) * | 1992-06-22 | 1995-12-08 | Technico Flor Sa | Nouvelles compositions cosmetiques ou alimentaires renfermant du copaiba. |
| FR2718059B1 (fr) * | 1994-03-31 | 1996-06-28 | Copigraph | Procédé de production de microcapsules à fort taux d'extrait sec contenant un liquide hydrophobe, microcapsules obtenues par ledit procédé et procédé d'obtention d'un papier sensible à la pression à l'aide de ces microcapsules. |
-
1994
- 1994-12-02 FR FR9414545A patent/FR2727633A1/fr active Granted
-
1995
- 1995-12-01 DE DE1995615807 patent/DE69515807T2/de not_active Expired - Fee Related
- 1995-12-01 EP EP95402716A patent/EP0714786B1/fr not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| FR2727633B1 (enrdf_load_stackoverflow) | 1997-02-28 |
| EP0714786A1 (fr) | 1996-06-05 |
| FR2727633A1 (fr) | 1996-06-07 |
| EP0714786B1 (fr) | 2000-03-22 |
| DE69515807D1 (de) | 2000-04-27 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8364 | No opposition during term of opposition | ||
| 8327 | Change in the person/name/address of the patent owner |
Owner name: ARJO WIGGINS BELGIUM S.A., NIVELLES, BE |
|
| 8339 | Ceased/non-payment of the annual fee |