DE3020148A1 - Konzentrierte mikrokapselsuspensionen fuer reaktionsdurchschreibepapiere - Google Patents
Konzentrierte mikrokapselsuspensionen fuer reaktionsdurchschreibepapiereInfo
- Publication number
- DE3020148A1 DE3020148A1 DE19803020148 DE3020148A DE3020148A1 DE 3020148 A1 DE3020148 A1 DE 3020148A1 DE 19803020148 DE19803020148 DE 19803020148 DE 3020148 A DE3020148 A DE 3020148A DE 3020148 A1 DE3020148 A1 DE 3020148A1
- Authority
- DE
- Germany
- Prior art keywords
- production
- polyaddition
- polyisocyanates
- microcapsules
- concentrated
- 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- Withdrawn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
- 239000000725 suspension Substances 0.000 title claims abstract description 30
- 239000003094 microcapsule Substances 0.000 title claims abstract description 26
- 238000006243 chemical reaction Methods 0.000 title claims abstract description 9
- 238000000034 method Methods 0.000 claims abstract description 34
- 238000004519 manufacturing process Methods 0.000 claims abstract description 20
- 239000005056 polyisocyanate Substances 0.000 claims abstract description 19
- 229920001228 polyisocyanate Polymers 0.000 claims abstract description 19
- 150000001875 compounds Chemical class 0.000 claims abstract description 9
- 239000002243 precursor Substances 0.000 claims abstract description 8
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 7
- 239000007900 aqueous suspension Substances 0.000 claims abstract 3
- 239000000975 dye Substances 0.000 claims description 10
- 238000005538 encapsulation Methods 0.000 claims 1
- 239000002775 capsule Substances 0.000 description 20
- 239000011248 coating agent Substances 0.000 description 11
- 238000000576 coating method Methods 0.000 description 10
- 239000011162 core material Substances 0.000 description 9
- 239000012074 organic phase Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 239000006185 dispersion Substances 0.000 description 7
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 6
- -1 malachite green lactone Chemical class 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 239000000084 colloidal system Substances 0.000 description 5
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
- 239000008346 aqueous phase Substances 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 4
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 4
- 239000012948 isocyanate Substances 0.000 description 4
- 150000002513 isocyanates Chemical class 0.000 description 4
- 229920002689 polyvinyl acetate Polymers 0.000 description 4
- 230000001681 protective effect Effects 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 125000006267 biphenyl group Chemical group 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 239000001569 carbon dioxide Substances 0.000 description 3
- 229910002092 carbon dioxide Inorganic materials 0.000 description 3
- 239000003995 emulsifying agent Substances 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 235000019198 oils Nutrition 0.000 description 3
- 229920000768 polyamine Polymers 0.000 description 3
- 239000011118 polyvinyl acetate Substances 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 239000002002 slurry Substances 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
- 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 description 2
- BANXPJUEBPWEOT-UHFFFAOYSA-N 2-methyl-Pentadecane Chemical compound CCCCCCCCCCCCCC(C)C BANXPJUEBPWEOT-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 2
- 238000012695 Interfacial polymerization Methods 0.000 description 2
- 239000005058 Isophorone diisocyanate Substances 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- ZKURGBYDCVNWKH-UHFFFAOYSA-N [3,7-bis(dimethylamino)phenothiazin-10-yl]-phenylmethanone Chemical compound 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 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 235000012216 bentonite Nutrition 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 235000005687 corn oil Nutrition 0.000 description 2
- 239000002285 corn oil Substances 0.000 description 2
- 235000012343 cottonseed oil Nutrition 0.000 description 2
- 239000002385 cottonseed oil Substances 0.000 description 2
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 2
- 150000004985 diamines Chemical class 0.000 description 2
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 2
- FLKPEMZONWLCSK-UHFFFAOYSA-N diethyl phthalate Chemical compound CCOC(=O)C1=CC=CC=C1C(=O)OCC FLKPEMZONWLCSK-UHFFFAOYSA-N 0.000 description 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
- 230000002209 hydrophobic effect Effects 0.000 description 2
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229910052901 montmorillonite Inorganic materials 0.000 description 2
- 150000002790 naphthalenes Chemical class 0.000 description 2
- 239000012188 paraffin wax Substances 0.000 description 2
- 239000000575 pesticide Substances 0.000 description 2
- 229920001568 phenolic resin Polymers 0.000 description 2
- 239000005011 phenolic resin Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000001694 spray drying Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 150000004897 thiazines Chemical class 0.000 description 2
- 125000001834 xanthenyl group Chemical class C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 description 2
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
- WOGVOIWHWZWYOZ-UHFFFAOYSA-N 1,1-diisocyanatoethane Chemical compound O=C=NC(C)N=C=O WOGVOIWHWZWYOZ-UHFFFAOYSA-N 0.000 description 1
- 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 1
- RTTZISZSHSCFRH-UHFFFAOYSA-N 1,3-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC(CN=C=O)=C1 RTTZISZSHSCFRH-UHFFFAOYSA-N 0.000 description 1
- IKYNWXNXXHWHLL-UHFFFAOYSA-N 1,3-diisocyanatopropane Chemical compound O=C=NCCCN=C=O IKYNWXNXXHWHLL-UHFFFAOYSA-N 0.000 description 1
- OHLKMGYGBHFODF-UHFFFAOYSA-N 1,4-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=C(CN=C=O)C=C1 OHLKMGYGBHFODF-UHFFFAOYSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- OVBFMUAFNIIQAL-UHFFFAOYSA-N 1,4-diisocyanatobutane Chemical compound O=C=NCCCCN=C=O OVBFMUAFNIIQAL-UHFFFAOYSA-N 0.000 description 1
- LLAPDLPYIYKTGQ-UHFFFAOYSA-N 1-aminoethyl Chemical group C[CH]N LLAPDLPYIYKTGQ-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
- 229940043268 2,2,4,4,6,8,8-heptamethylnonane Drugs 0.000 description 1
- SAMBPHSTNUKQPJ-UHFFFAOYSA-N 2-benzyl-6-phenylphenol Chemical group C1=CC=C(C=2C=CC=CC=2)C(O)=C1CC1=CC=CC=C1 SAMBPHSTNUKQPJ-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
- RNLHGQLZWXBQNY-UHFFFAOYSA-N 3-(aminomethyl)-3,5,5-trimethylcyclohexan-1-amine Chemical compound CC1(C)CC(N)CC(C)(CN)C1 RNLHGQLZWXBQNY-UHFFFAOYSA-N 0.000 description 1
- KFMASHHCLJTUDI-UHFFFAOYSA-N 4-[2-[2,2-bis[4-(dimethylamino)phenyl]-1-phenylethoxy]-1-[4-(dimethylamino)phenyl]-2-phenylethyl]-n,n-dimethylaniline Chemical compound C1=CC(N(C)C)=CC=C1C(C=1C=CC(=CC=1)N(C)C)C(C=1C=CC=CC=1)OC(C=1C=CC=CC=1)C(C=1C=CC(=CC=1)N(C)C)C1=CC=C(N(C)C)C=C1 KFMASHHCLJTUDI-UHFFFAOYSA-N 0.000 description 1
- TYMLOMAKGOJONV-UHFFFAOYSA-N 4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1 TYMLOMAKGOJONV-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- ODYFMMXCYGDDCM-UHFFFAOYSA-N C1(=CC=CC=C1)C.C(CCCCCN=C=O)N=C=O Chemical compound C1(=CC=CC=C1)C.C(CCCCCN=C=O)N=C=O ODYFMMXCYGDDCM-UHFFFAOYSA-N 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-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
- MQIUGAXCHLFZKX-UHFFFAOYSA-N Di-n-octyl phthalate Natural products CCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC MQIUGAXCHLFZKX-UHFFFAOYSA-N 0.000 description 1
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 244000043261 Hevea brasiliensis Species 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical class CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 1
- 229920001800 Shellac Polymers 0.000 description 1
- 240000006394 Sorghum bicolor Species 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 125000003710 aryl alkyl group Chemical class 0.000 description 1
- 150000008378 aryl ethers Chemical class 0.000 description 1
- 229960000892 attapulgite Drugs 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 description 1
- RGTXVXDNHPWPHH-UHFFFAOYSA-N butane-1,3-diamine Chemical compound CC(N)CCN RGTXVXDNHPWPHH-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
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- VKIRRGRTJUUZHS-UHFFFAOYSA-N cyclohexane-1,4-diamine Chemical compound NC1CCC(N)CC1 VKIRRGRTJUUZHS-UHFFFAOYSA-N 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
- JBSLOWBPDRZSMB-FPLPWBNLSA-N dibutyl (z)-but-2-enedioate Chemical compound CCCCOC(=O)\C=C/C(=O)OCCCC JBSLOWBPDRZSMB-FPLPWBNLSA-N 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- KORSJDCBLAPZEQ-UHFFFAOYSA-N dicyclohexylmethane-4,4'-diisocyanate Chemical compound C1CC(N=C=O)CCC1CC1CCC(N=C=O)CC1 KORSJDCBLAPZEQ-UHFFFAOYSA-N 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical class C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
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- 238000001704 evaporation Methods 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 235000021323 fish oil Nutrition 0.000 description 1
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- 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
- 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
- 239000004009 herbicide Substances 0.000 description 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
- KUVMKLCGXIYSNH-UHFFFAOYSA-N isopentadecane Natural products CCCCCCCCCCCCC(C)C KUVMKLCGXIYSNH-UHFFFAOYSA-N 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 229940107698 malachite green Drugs 0.000 description 1
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- ODZZIKZQNODXFS-UHFFFAOYSA-N n,n'-dimethyl-n'-[2-(methylamino)ethyl]ethane-1,2-diamine Chemical compound CNCCN(C)CCNC ODZZIKZQNODXFS-UHFFFAOYSA-N 0.000 description 1
- JVKAWJASTRPFQY-UHFFFAOYSA-N n-(2-aminoethyl)hydroxylamine Chemical compound NCCNO JVKAWJASTRPFQY-UHFFFAOYSA-N 0.000 description 1
- 229920003052 natural elastomer Polymers 0.000 description 1
- 229920001194 natural rubber Polymers 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
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- 229910052625 palygorskite Inorganic materials 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical class OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- 235000015277 pork Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000011257 shell material Substances 0.000 description 1
- 239000004208 shellac Substances 0.000 description 1
- ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
- 229940113147 shellac Drugs 0.000 description 1
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- 125000006850 spacer group Chemical group 0.000 description 1
- 150000003413 spiro compounds Chemical class 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 125000001273 sulfonato group Chemical class [O-]S(*)(=O)=O 0.000 description 1
- 150000001911 terphenyls Chemical class 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J13/00—Colloid chemistry, e.g. the production of colloidal materials or their solutions, not otherwise provided for; Making microcapsules or microballoons
- B01J13/02—Making microcapsules or microballoons
- B01J13/06—Making microcapsules or microballoons by phase separation
- B01J13/14—Polymerisation; cross-linking
- B01J13/16—Interfacial polymerisation
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Dispersion Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Manufacturing Of Micro-Capsules (AREA)
- Color Printing (AREA)
- Polyurethanes Or Polyureas (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19803020148 DE3020148A1 (de) | 1980-05-28 | 1980-05-28 | Konzentrierte mikrokapselsuspensionen fuer reaktionsdurchschreibepapiere |
| DE8181103743T DE3160942D1 (en) | 1980-05-28 | 1981-05-15 | Concentrated suspension of microcapsules, a process for its preparation and its use in transfer-copying paper |
| EP81103743A EP0040770B1 (de) | 1980-05-28 | 1981-05-15 | Konzentrierte Mikrokapselsuspension, ein Verfahren zu ihrer Herstellung und ihre Verwendung für Reaktionsdurchschreibepapier |
| AT81103743T ATE4675T1 (de) | 1980-05-28 | 1981-05-15 | Konzentrierte mikrokapselsuspension, ein verfahren zu ihrer herstellung und ihre verwendung fuer reaktionsdurchschreibepapier. |
| US06/265,537 US4428978A (en) | 1980-05-28 | 1981-05-20 | Concentrated microcapsule suspensions for reaction copying papers |
| JP7818281A JPS5724629A (en) | 1980-05-28 | 1981-05-25 | Manufacture of aqueous suspension |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19803020148 DE3020148A1 (de) | 1980-05-28 | 1980-05-28 | Konzentrierte mikrokapselsuspensionen fuer reaktionsdurchschreibepapiere |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE3020148A1 true DE3020148A1 (de) | 1981-12-03 |
Family
ID=6103379
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19803020148 Withdrawn DE3020148A1 (de) | 1980-05-28 | 1980-05-28 | Konzentrierte mikrokapselsuspensionen fuer reaktionsdurchschreibepapiere |
| DE8181103743T Expired DE3160942D1 (en) | 1980-05-28 | 1981-05-15 | Concentrated suspension of microcapsules, a process for its preparation and its use in transfer-copying paper |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE8181103743T Expired DE3160942D1 (en) | 1980-05-28 | 1981-05-15 | Concentrated suspension of microcapsules, a process for its preparation and its use in transfer-copying paper |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US4428978A (en, 2012) |
| EP (1) | EP0040770B1 (en, 2012) |
| JP (1) | JPS5724629A (en, 2012) |
| AT (1) | ATE4675T1 (en, 2012) |
| DE (2) | DE3020148A1 (en, 2012) |
Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5922792A (ja) * | 1982-07-30 | 1984-02-06 | Kanzaki Paper Mfg Co Ltd | 感熱記録体用塗液の調成法 |
| DE3442268C1 (de) * | 1984-03-09 | 1990-08-02 | Papierfabrik August Koehler AG, 7602 Oberkirch | Verfahren zum Einkapseln geloester Reaktionspartner von Farbreaktionssystemen,die danach erhaeltlichen Kapseln sowie deren Verwendung in Farbreaktionspapieren |
| DE3480345D1 (en) * | 1984-05-28 | 1989-12-07 | Joachim Schmidt | Use of isocyanate or isothiocyanate polymers for making microcapsules |
| FR2591124B1 (fr) * | 1985-12-10 | 1988-02-12 | Rhone Poulenc Spec Chim | Procede de microencapsulation par polyaddition-interfaciale. |
| US4681806A (en) * | 1986-02-13 | 1987-07-21 | Minnesota Mining And Manufacturing Company | Particles containing releasable fill material and method of making same |
| DE3635821A1 (de) * | 1986-10-22 | 1988-04-28 | Bayer Ag | Mikrokapseln mit verbesserten waenden |
| US4940738A (en) * | 1988-01-07 | 1990-07-10 | The Standard Register Company | High solids CB printing ink containing a protective colloid blend |
| US4940739A (en) * | 1988-01-07 | 1990-07-10 | The Standard Register Company | Process for making a high solids CB printing ink |
| US4889877A (en) * | 1988-01-07 | 1989-12-26 | The Standard Register Company | High solids CB printing ink |
| FR2649019B1 (fr) * | 1989-06-30 | 1991-10-18 | Hutchinson | Microcapsules contenant des substances amphiphiles hydrosolubles |
| US5225118A (en) * | 1990-08-15 | 1993-07-06 | Boise Cascade Corporation | Process for manufacturing polyurea microcapsules and product therefrom |
| US5204184A (en) * | 1990-09-10 | 1993-04-20 | The Standard Register Company | Microencapsulation using tertiary aliphatic isocyanate capsule wall material |
| US5164126A (en) * | 1991-03-05 | 1992-11-17 | Appleton Papers Inc. | Process for microencapsulation |
| US5591255A (en) * | 1993-12-29 | 1997-01-07 | Chromatic Technologies, Inc. | Thermochromic ink formulations, nail lacquer and methods of use |
| DE4436535A1 (de) * | 1994-10-13 | 1996-04-18 | Bayer Ag | Verfahren zur Mikroverkapselung unter Verwendung öllöslicher Emulgatoren |
| DE19541054B4 (de) * | 1995-11-03 | 2006-09-07 | Giesecke & Devrient Gmbh | Pigmente und Verfahren zu ihrer Herstellung |
| US6610351B2 (en) | 2000-04-12 | 2003-08-26 | Quantag Systems, Inc. | Raman-active taggants and their recognition |
| CN104144968A (zh) | 2011-12-15 | 2014-11-12 | 富士胶片亨特化学品美国有限公司 | 用于聚酰胺酰亚胺树脂的低毒性溶剂系统和溶剂系统的制备 |
| US9029441B2 (en) | 2011-12-15 | 2015-05-12 | Fujifilm Hunt Chemicals Us, Inc. | Low toxicity solvent system for polyamideimide and polyamide amic acid resins and coating solutions thereof |
| US20130183620A1 (en) * | 2012-01-18 | 2013-07-18 | Yuka Ogo | Chemical coating composition for forming a laser-markable material and a laser-markable material |
| JP6151725B2 (ja) | 2012-03-08 | 2017-06-21 | コンセホ・スペリオール・デ・インベスティガシオネス・シエンティフィカスＣｏｎｓｅｊｏ Ｓｕｐｅｒｉｏｒ Ｄｅ Ｉｎｖｅｓｔｉｇａｃｉｏｎｅｓ Ｃｉｅｎｔｉｆｉｃａｓ | フォトクロミック特性を有するコーティング、そのコーティングの製造方法、ならびに光学物品および光沢表面に適用可能なそれらの使用 |
| EP2954373B1 (en) * | 2013-02-06 | 2019-04-24 | Fujifilm Hunt Chemicals US, Inc. | Chemical coating for a laser-markable material |
| US9815941B2 (en) | 2014-04-17 | 2017-11-14 | Cymer-Dayton, Llc | Low toxicity solvent system for polyamdieimide and polyamide amic acid resin manufacture |
| US9725617B2 (en) | 2014-04-17 | 2017-08-08 | Fujifilm Hunt Chemicals U.S.A., Inc. | Low toxicity solvent system for polyamideimide and polyamide amic acid resin coating |
| GB201804038D0 (en) * | 2018-03-14 | 2018-04-25 | Givaudan Sa | Improvements in or realating to organic compounds |
| FR3092502A1 (fr) | 2019-02-12 | 2020-08-14 | Européenne D'application Des Cristaux Liquides | Formulation de microcapsules à membrane aminoplaste renforcée |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| GB1091141A (en) * | 1963-12-13 | 1967-11-15 | Wallace & Tiernan Inc | Encapsulating liquids or solids by interfacial polymerisation |
| DE1222067B (de) * | 1964-11-07 | 1966-08-04 | Bayer Ag | Verfahren zur Herstellung von einheitlichen organischen Polyisocyanaten |
| ES390653A1 (es) | 1970-04-28 | 1974-03-16 | Fuji Photo Film Co Ltd | Procedimiento para la produccion de microcapsulas conte- niendo liquido aceitoso. |
| US3677787A (en) | 1970-10-21 | 1972-07-18 | Us Navy | Method of rehardening encapsulating compositions |
| US3886085A (en) * | 1971-08-31 | 1975-05-27 | Fuji Photo Film Co Ltd | Process for producing fine oil-containing microcapsules having strong protective shells and microcapsules produced thereby |
| BE790373A (fr) * | 1971-10-21 | 1973-02-15 | Fuji Photo Film Co Ltd | Feuille d'enregistrement sensible a la pression comportant des micro-capsules ayant des parois en polyuree |
| US3914511A (en) * | 1973-10-18 | 1975-10-21 | Champion Int Corp | Spot printing of color-forming microcapsules and co-reactant therefor |
| DE2541001A1 (de) * | 1975-09-13 | 1977-03-17 | Eupaco Papier Vertrieb Gmbh & | Verfahren zur herstellung von zonenweise durchschreibenden farbreaktionspapieren |
| DE2557407A1 (de) * | 1975-12-19 | 1977-06-30 | Bayer Ag | Verfahren zur herstellung von polyurethan-polyharnstoff-hohlperlen |
| DE2655048A1 (de) * | 1976-12-04 | 1978-06-08 | Bayer Ag | Mikroverkapselung mit modifizierten aliphatischen polyisocyanaten |
| US4140516A (en) | 1977-05-31 | 1979-02-20 | Stauffer Chemical Company | Encapsulation process employing phase transfer catalysts |
| DE2738509A1 (de) | 1977-08-26 | 1979-03-08 | Bayer Ag | Reaktionsdurchschreibepapiere |
| DE2756586A1 (de) * | 1977-12-19 | 1979-06-21 | Renker Gmbh | Verfahren zum beschichten von oberflaechen mit einer mikrokapsel-dispersion |
| DE2833651A1 (de) * | 1978-08-01 | 1980-02-21 | Basf Ag | Verfahren zum aufbringen von mikrokapseln auf traegermaterial |
| DE2909950A1 (de) | 1979-03-14 | 1980-10-02 | Bayer Ag | Mikrokapseln |
| DE2909906A1 (de) * | 1979-03-14 | 1980-10-02 | Bayer Ag | Verfahren zur kontinuierlichen herstellung von mikrokapseln |
| DE2930408A1 (de) | 1979-07-26 | 1981-02-12 | Bayer Ag | Reaktionsdurchschreibepapier |
-
1980
- 1980-05-28 DE DE19803020148 patent/DE3020148A1/de not_active Withdrawn
-
1981
- 1981-05-15 EP EP81103743A patent/EP0040770B1/de not_active Expired
- 1981-05-15 DE DE8181103743T patent/DE3160942D1/de not_active Expired
- 1981-05-15 AT AT81103743T patent/ATE4675T1/de active
- 1981-05-20 US US06/265,537 patent/US4428978A/en not_active Expired - Lifetime
- 1981-05-25 JP JP7818281A patent/JPS5724629A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5724629A (en) | 1982-02-09 |
| EP0040770B1 (de) | 1983-09-21 |
| JPH0119934B2 (en, 2012) | 1989-04-13 |
| US4428978A (en) | 1984-01-31 |
| ATE4675T1 (de) | 1983-10-15 |
| EP0040770A1 (de) | 1981-12-02 |
| DE3160942D1 (en) | 1983-10-27 |
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Legal Events
| Date | Code | Title | Description |
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| 8130 | Withdrawal |