CA1153635A - Process for the production of microcapsules from a melamine-formaldehyde precondensate - Google Patents
Process for the production of microcapsules from a melamine-formaldehyde precondensateInfo
- Publication number
- CA1153635A CA1153635A CA000374007A CA374007A CA1153635A CA 1153635 A CA1153635 A CA 1153635A CA 000374007 A CA000374007 A CA 000374007A CA 374007 A CA374007 A CA 374007A CA 1153635 A CA1153635 A CA 1153635A
- Authority
- CA
- Canada
- Prior art keywords
- dispersion
- precondensate
- mixture
- microcapsules
- added
- 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
Links
- 239000003094 microcapsule Substances 0.000 title claims abstract description 88
- 238000000034 method Methods 0.000 title claims abstract description 59
- IVJISJACKSSFGE-UHFFFAOYSA-N formaldehyde;1,3,5-triazine-2,4,6-triamine Chemical compound O=C.NC1=NC(N)=NC(N)=N1 IVJISJACKSSFGE-UHFFFAOYSA-N 0.000 title claims abstract description 39
- 230000008569 process Effects 0.000 title claims abstract description 39
- 229920000877 Melamine resin Polymers 0.000 title claims abstract description 37
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 10
- 239000006185 dispersion Substances 0.000 claims abstract description 111
- 239000000463 material Substances 0.000 claims abstract description 52
- 239000007788 liquid Substances 0.000 claims abstract description 35
- 230000002378 acidificating effect Effects 0.000 claims abstract description 13
- 229920003169 water-soluble polymer Polymers 0.000 claims abstract description 10
- 238000007171 acid catalysis Methods 0.000 claims abstract description 4
- 229920000642 polymer Polymers 0.000 claims description 37
- 238000009833 condensation Methods 0.000 claims description 20
- 230000005494 condensation Effects 0.000 claims description 20
- 230000036961 partial effect Effects 0.000 claims description 18
- 230000015572 biosynthetic process Effects 0.000 claims description 11
- 239000012736 aqueous medium Substances 0.000 claims description 9
- 229920002134 Carboxymethyl cellulose Polymers 0.000 claims description 7
- 229920001807 Urea-formaldehyde Polymers 0.000 claims description 7
- ODGAOXROABLFNM-UHFFFAOYSA-N polynoxylin Chemical compound O=C.NC(N)=O ODGAOXROABLFNM-UHFFFAOYSA-N 0.000 claims description 7
- 239000002243 precursor Substances 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 6
- 239000001768 carboxy methyl cellulose Substances 0.000 claims description 6
- 235000010948 carboxy methyl cellulose Nutrition 0.000 claims description 6
- 239000008112 carboxymethyl-cellulose Substances 0.000 claims description 6
- 150000002148 esters Chemical class 0.000 claims description 5
- 230000000087 stabilizing effect Effects 0.000 claims description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
- 229920003171 Poly (ethylene oxide) Polymers 0.000 claims description 4
- 229920002472 Starch Polymers 0.000 claims description 4
- 238000006482 condensation reaction Methods 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 229920005989 resin Polymers 0.000 claims description 4
- 239000011347 resin Substances 0.000 claims description 4
- 235000019698 starch Nutrition 0.000 claims description 4
- 239000008107 starch Substances 0.000 claims description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 3
- 239000004952 Polyamide Substances 0.000 claims description 3
- 235000010443 alginic acid Nutrition 0.000 claims description 3
- 229920000615 alginic acid Polymers 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 3
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 claims description 3
- 229920002647 polyamide Polymers 0.000 claims description 3
- 229920001451 polypropylene glycol Polymers 0.000 claims description 3
- 239000004814 polyurethane Substances 0.000 claims description 3
- 229920002635 polyurethane Polymers 0.000 claims description 3
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 2
- FHVDTGUDJYJELY-UHFFFAOYSA-N 6-{[2-carboxy-4,5-dihydroxy-6-(phosphanyloxy)oxan-3-yl]oxy}-4,5-dihydroxy-3-phosphanyloxane-2-carboxylic acid Chemical compound O1C(C(O)=O)C(P)C(O)C(O)C1OC1C(C(O)=O)OC(OP)C(O)C1O FHVDTGUDJYJELY-UHFFFAOYSA-N 0.000 claims description 2
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical group NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 2
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 claims description 2
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 2
- 239000004354 Hydroxyethyl cellulose Substances 0.000 claims description 2
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical group SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 claims description 2
- 229920000881 Modified starch Polymers 0.000 claims description 2
- 229940072056 alginate Drugs 0.000 claims description 2
- 150000001408 amides Chemical class 0.000 claims description 2
- 235000019426 modified starch Nutrition 0.000 claims description 2
- 229920000768 polyamine Polymers 0.000 claims description 2
- 150000003573 thiols Chemical class 0.000 claims description 2
- 229920001285 xanthan gum Polymers 0.000 claims description 2
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 claims 1
- 229940071826 hydroxyethyl cellulose Drugs 0.000 claims 1
- 239000002609 medium Substances 0.000 claims 1
- 230000003019 stabilising effect Effects 0.000 abstract description 11
- 230000003993 interaction Effects 0.000 abstract description 3
- 239000000203 mixture Substances 0.000 description 76
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 63
- 239000000243 solution Substances 0.000 description 58
- 239000008367 deionised water Substances 0.000 description 40
- 239000007787 solid Substances 0.000 description 38
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 36
- 239000000725 suspension Substances 0.000 description 31
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 27
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 18
- 229920001577 copolymer Polymers 0.000 description 16
- 238000005538 encapsulation Methods 0.000 description 12
- 238000003756 stirring Methods 0.000 description 12
- 238000007792 addition Methods 0.000 description 11
- 235000019270 ammonium chloride Nutrition 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 239000000376 reactant Substances 0.000 description 7
- KEQXNNJHMWSZHK-UHFFFAOYSA-L 1,3,2,4$l^{2}-dioxathiaplumbetane 2,2-dioxide Chemical compound [Pb+2].[O-]S([O-])(=O)=O KEQXNNJHMWSZHK-UHFFFAOYSA-L 0.000 description 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 5
- -1 ammonium chloride Chemical class 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 239000003350 kerosene Substances 0.000 description 5
- 230000035484 reaction time Effects 0.000 description 5
- 230000008901 benefit Effects 0.000 description 4
- 239000002775 capsule Substances 0.000 description 4
- 238000003801 milling Methods 0.000 description 4
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 3
- 229910019142 PO4 Inorganic materials 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 229910021641 deionized water Inorganic materials 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 235000021317 phosphate Nutrition 0.000 description 3
- 239000004033 plastic Substances 0.000 description 3
- 229920003023 plastic Polymers 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 230000009257 reactivity Effects 0.000 description 3
- IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 238000005354 coacervation Methods 0.000 description 2
- 238000004581 coalescence Methods 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
- MGWAVDBGNNKXQV-UHFFFAOYSA-N diisobutyl phthalate Chemical compound CC(C)COC(=O)C1=CC=CC=C1C(=O)OCC(C)C MGWAVDBGNNKXQV-UHFFFAOYSA-N 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 230000002209 hydrophobic effect Effects 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- 239000000661 sodium alginate Substances 0.000 description 2
- 235000010413 sodium alginate Nutrition 0.000 description 2
- 229940005550 sodium alginate Drugs 0.000 description 2
- 150000001911 terphenyls Chemical class 0.000 description 2
- 229940035658 visco-gel Drugs 0.000 description 2
- LIZLYZVAYZQVPG-UHFFFAOYSA-N (3-bromo-2-fluorophenyl)methanol Chemical compound OCC1=CC=CC(Br)=C1F LIZLYZVAYZQVPG-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 1
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
- 229920002126 Acrylic acid copolymer Polymers 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- OPFTUNCRGUEPRZ-QLFBSQMISA-N Cyclohexane Natural products CC(=C)[C@@H]1CC[C@@](C)(C=C)[C@H](C(C)=C)C1 OPFTUNCRGUEPRZ-QLFBSQMISA-N 0.000 description 1
- MQIUGAXCHLFZKX-UHFFFAOYSA-N Di-n-octyl phthalate Chemical compound CCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC MQIUGAXCHLFZKX-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 229920002873 Polyethylenimine Polymers 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 229920006322 acrylamide copolymer Polymers 0.000 description 1
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical class OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 1
- 238000005054 agglomeration Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 229920006320 anionic starch Polymers 0.000 description 1
- IWLBIFVMPLUHLK-UHFFFAOYSA-N azane;formaldehyde Chemical compound N.O=C IWLBIFVMPLUHLK-UHFFFAOYSA-N 0.000 description 1
- 238000010923 batch production Methods 0.000 description 1
- 239000004490 capsule suspension Substances 0.000 description 1
- 229920003090 carboxymethyl hydroxyethyl cellulose Polymers 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 238000001246 colloidal dispersion Methods 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 150000001924 cycloalkanes Chemical class 0.000 description 1
- XOVJAYNMQDTIJD-UHFFFAOYSA-N cyclopentobarbital Chemical compound C1CC=CC1C1(CC=C)C(=O)NC(=O)NC1=O XOVJAYNMQDTIJD-UHFFFAOYSA-N 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical class C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- FWQHNLCNFPYBCA-UHFFFAOYSA-N fluoran Chemical class C12=CC=CC=C2OC2=CC=CC=C2C11OC(=O)C2=CC=CC=C21 FWQHNLCNFPYBCA-UHFFFAOYSA-N 0.000 description 1
- 239000003517 fume Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002466 imines Chemical class 0.000 description 1
- PXZQEOJJUGGUIB-UHFFFAOYSA-N isoindolin-1-one Chemical compound C1=CC=C2C(=O)NCC2=C1 PXZQEOJJUGGUIB-UHFFFAOYSA-N 0.000 description 1
- 239000011344 liquid material Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- KNRMURHAZMNRGD-UHFFFAOYSA-N n,n'-dibenzylethanedithioamide Chemical compound C=1C=CC=CC=1CNC(=S)C(=S)NCC1=CC=CC=C1 KNRMURHAZMNRGD-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 125000005498 phthalate group Chemical class 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- 125000005506 phthalide group Chemical class 0.000 description 1
- 229920000867 polyelectrolyte Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000008439 repair process Effects 0.000 description 1
- 239000011369 resultant mixture Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 description 1
- 229940093635 tributyl phosphate Drugs 0.000 description 1
- 239000000230 xanthan gum Substances 0.000 description 1
- 235000010493 xanthan gum Nutrition 0.000 description 1
- 229940082509 xanthan gum Drugs 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
-
- 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
- B01J13/18—In situ polymerisation with all reactants being present in the same phase
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/249921—Web or sheet containing structurally defined element or component
- Y10T428/249994—Composite having a component wherein a constituent is liquid or is contained within preformed walls [e.g., impregnant-filled, previously void containing component, etc.]
- Y10T428/249995—Constituent is in liquid form
- Y10T428/249997—Encapsulated liquid
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Dispersion Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Manufacturing Of Micro-Capsules (AREA)
- Color Printing (AREA)
- Phenolic Resins Or Amino Resins (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8011461 | 1980-04-08 | ||
| GB8011461 | 1980-04-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1153635A true CA1153635A (en) | 1983-09-13 |
Family
ID=10512630
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000374007A Expired CA1153635A (en) | 1980-04-08 | 1981-03-27 | Process for the production of microcapsules from a melamine-formaldehyde precondensate |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US4396670A (en:Method) |
| JP (1) | JPS56155636A (en:Method) |
| AT (1) | AT382796B (en:Method) |
| AU (1) | AU539624B2 (en:Method) |
| BE (1) | BE888297A (en:Method) |
| BR (1) | BR8102014A (en:Method) |
| CA (1) | CA1153635A (en:Method) |
| CH (1) | CH649228A5 (en:Method) |
| DE (1) | DE3114035A1 (en:Method) |
| DK (1) | DK156781A (en:Method) |
| ES (1) | ES501139A0 (en:Method) |
| FI (1) | FI71235C (en:Method) |
| FR (1) | FR2479835A1 (en:Method) |
| GR (1) | GR75211B (en:Method) |
| HK (1) | HK68284A (en:Method) |
| IT (1) | IT1200580B (en:Method) |
| LU (1) | LU83287A1 (en:Method) |
| NL (1) | NL8101684A (en:Method) |
| NO (1) | NO811164L (en:Method) |
| NZ (1) | NZ196601A (en:Method) |
| PT (1) | PT72791B (en:Method) |
| SE (1) | SE454651B (en:Method) |
| ZA (1) | ZA811973B (en:Method) |
Families Citing this family (111)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4454083A (en) * | 1981-12-21 | 1984-06-12 | Appleton Papers Inc. | Continuous microencapsulation |
| US4561981A (en) * | 1984-01-27 | 1985-12-31 | Characklis William G | Treatment of fouling with microcapsules |
| DE3447298C1 (de) * | 1984-12-24 | 1986-04-24 | Papierfabrik August Koehler AG, 7602 Oberkirch | Verfahren zur Mikroverkapselung von Ölen mit darin gelösten Farbreaktionspartnern und danach hergestellte Mikrokapseln |
| DE3545803C2 (de) * | 1984-12-24 | 1991-02-14 | Papierfabrik August Koehler AG, 7602 Oberkirch | Verfahren zur Mikroverkapselung von Ölen mit darin gelösten Farbreaktionspartnern, danach hergestellte Mikrokapseln und deren Verwendung in Farbreaktionsaufzeichnungssystemen |
| US5089339A (en) * | 1984-12-24 | 1992-02-18 | Pietsch Guenter | Aminoplast microencapsulation system |
| US4594370A (en) * | 1985-03-29 | 1986-06-10 | The Mead Corporation | Amine-formaldehyde microencapsulation process |
| US4822769A (en) * | 1985-06-12 | 1989-04-18 | Nashua Corporation | High solids content coated back paper |
| DE3532878A1 (de) * | 1985-09-14 | 1987-03-26 | Basf Ag | Kontinuierliches verfahren zur herstellung von mikrokapseln mit waenden aus melamin-formaldehydkondensaten in waessriger dispersion |
| US4690825A (en) * | 1985-10-04 | 1987-09-01 | Advanced Polymer Systems, Inc. | Method for delivering an active ingredient by controlled time release utilizing a novel delivery vehicle which can be prepared by a process utilizing the active ingredient as a porogen |
| DE3709586C1 (de) * | 1987-03-24 | 1988-07-14 | Koehler August Papierfab | Verfahren zur Mikroverkapselung von hydrophoben OElen,die danach erhaeltlichen Mikrokapseln und deren Verwendung |
| JPS63268777A (ja) * | 1987-04-25 | 1988-11-07 | Kanzaki Paper Mfg Co Ltd | マイクロカプセルインキ組成物 |
| US4766176A (en) * | 1987-07-20 | 1988-08-23 | Dow Corning Corporation | Storage stable heat curable organosiloxane compositions containing microencapsulated platinum-containing catalysts |
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1981
- 1981-03-24 NZ NZ19660181A patent/NZ196601A/xx unknown
- 1981-03-24 ZA ZA00811973A patent/ZA811973B/xx unknown
- 1981-03-24 AU AU68693/81A patent/AU539624B2/en not_active Ceased
- 1981-03-24 US US06/247,150 patent/US4396670A/en not_active Expired - Lifetime
- 1981-03-27 CA CA000374007A patent/CA1153635A/en not_active Expired
- 1981-03-31 SE SE8102051A patent/SE454651B/sv not_active IP Right Cessation
- 1981-04-02 PT PT7279181A patent/PT72791B/pt unknown
- 1981-04-03 FI FI811041A patent/FI71235C/fi not_active IP Right Cessation
- 1981-04-03 NO NO811164A patent/NO811164L/no unknown
- 1981-04-03 BR BR8102014A patent/BR8102014A/pt unknown
- 1981-04-03 NL NL8101684A patent/NL8101684A/nl not_active Application Discontinuation
- 1981-04-06 AT AT159381A patent/AT382796B/de not_active IP Right Cessation
- 1981-04-06 IT IT2094781A patent/IT1200580B/it active
- 1981-04-06 GR GR64592A patent/GR75211B/el unknown
- 1981-04-06 BE BE0/204386A patent/BE888297A/fr not_active IP Right Cessation
- 1981-04-07 DE DE3114035A patent/DE3114035A1/de active Granted
- 1981-04-07 LU LU83287A patent/LU83287A1/fr unknown
- 1981-04-07 DK DK156781A patent/DK156781A/da not_active IP Right Cessation
- 1981-04-07 ES ES501139A patent/ES501139A0/es active Granted
- 1981-04-07 FR FR8106943A patent/FR2479835A1/fr active Granted
- 1981-04-08 CH CH2371/81A patent/CH649228A5/de not_active IP Right Cessation
- 1981-04-08 JP JP5287881A patent/JPS56155636A/ja active Granted
-
1984
- 1984-08-30 HK HK682/84A patent/HK68284A/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| AU6869381A (en) | 1981-10-15 |
| IT1200580B (it) | 1989-01-27 |
| US4396670A (en) | 1983-08-02 |
| JPH0347139B2 (en:Method) | 1991-07-18 |
| FI71235C (fi) | 1986-12-19 |
| SE454651B (sv) | 1988-05-24 |
| ZA811973B (en) | 1982-04-28 |
| ATA159381A (de) | 1986-09-15 |
| FR2479835B1 (en:Method) | 1983-06-10 |
| LU83287A1 (fr) | 1981-12-02 |
| DK156781A (da) | 1981-10-09 |
| DE3114035C2 (en:Method) | 1988-03-31 |
| AU539624B2 (en) | 1984-10-11 |
| NL8101684A (nl) | 1981-11-02 |
| ES8202491A1 (es) | 1982-02-01 |
| NZ196601A (en) | 1982-12-21 |
| FR2479835A1 (fr) | 1981-10-09 |
| GR75211B (en:Method) | 1984-07-13 |
| SE8102051L (sv) | 1981-10-09 |
| JPS56155636A (en) | 1981-12-01 |
| ES501139A0 (es) | 1982-02-01 |
| IT8120947A0 (it) | 1981-04-06 |
| FI811041L (fi) | 1981-10-09 |
| DE3114035C3 (en:Method) | 1993-05-13 |
| AT382796B (de) | 1987-04-10 |
| BR8102014A (pt) | 1981-10-13 |
| PT72791A (en) | 1981-05-01 |
| DE3114035A1 (de) | 1982-02-11 |
| FI71235B (fi) | 1986-09-09 |
| NO811164L (no) | 1981-10-09 |
| PT72791B (en) | 1982-07-26 |
| CH649228A5 (de) | 1985-05-15 |
| HK68284A (en) | 1984-09-07 |
| BE888297A (fr) | 1981-07-31 |
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