CA1052195A - Production of dual walled microcapsules by reducing ph to polymerize aminoaldehyde precondensate - Google Patents
Production of dual walled microcapsules by reducing ph to polymerize aminoaldehyde precondensateInfo
- Publication number
- CA1052195A CA1052195A CA230,762A CA230762A CA1052195A CA 1052195 A CA1052195 A CA 1052195A CA 230762 A CA230762 A CA 230762A CA 1052195 A CA1052195 A CA 1052195A
- Authority
- CA
- Canada
- Prior art keywords
- continuous phase
- set forth
- phase
- microcapsules
- solution
- 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 45
- 238000004519 manufacturing process Methods 0.000 title abstract description 8
- 230000009977 dual effect Effects 0.000 title 1
- 238000000034 method Methods 0.000 claims abstract description 34
- 239000000463 material Substances 0.000 claims abstract description 33
- 239000007788 liquid Substances 0.000 claims abstract description 11
- 239000002775 capsule Substances 0.000 claims description 49
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 30
- 238000012696 Interfacial polycondensation Methods 0.000 claims description 23
- 239000000376 reactant Substances 0.000 claims description 22
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical group NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 claims description 17
- 229920001807 Urea-formaldehyde Polymers 0.000 claims description 16
- LXEJRKJRKIFVNY-UHFFFAOYSA-N terephthaloyl chloride Chemical group ClC(=O)C1=CC=C(C(Cl)=O)C=C1 LXEJRKJRKIFVNY-UHFFFAOYSA-N 0.000 claims description 12
- GZCGUPFRVQAUEE-SLPGGIOYSA-N aldehydo-D-glucose Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O GZCGUPFRVQAUEE-SLPGGIOYSA-N 0.000 claims description 6
- 238000006116 polymerization reaction Methods 0.000 claims description 6
- 230000002844 continuous effect Effects 0.000 claims description 4
- 238000006068 polycondensation reaction Methods 0.000 claims description 4
- 239000002244 precipitate Substances 0.000 claims description 4
- 229920003176 water-insoluble polymer Polymers 0.000 claims description 4
- 238000004132 cross linking Methods 0.000 claims 1
- 239000002243 precursor Substances 0.000 abstract description 17
- 238000006243 chemical reaction Methods 0.000 abstract description 8
- 239000006227 byproduct Substances 0.000 abstract description 4
- 239000000243 solution Substances 0.000 description 67
- 238000000576 coating method Methods 0.000 description 38
- 239000002002 slurry Substances 0.000 description 38
- 239000011248 coating agent Substances 0.000 description 33
- 239000012071 phase Substances 0.000 description 29
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 24
- 239000000839 emulsion Substances 0.000 description 22
- 239000004927 clay Substances 0.000 description 18
- 229920005989 resin Polymers 0.000 description 18
- 239000011347 resin Substances 0.000 description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 239000000203 mixture Substances 0.000 description 13
- 239000004952 Polyamide Substances 0.000 description 11
- 239000007864 aqueous solution Substances 0.000 description 11
- IMROMDMJAWUWLK-UHFFFAOYSA-N Ethenol Chemical compound OC=C IMROMDMJAWUWLK-UHFFFAOYSA-N 0.000 description 10
- 239000002253 acid Substances 0.000 description 10
- 238000007792 addition Methods 0.000 description 10
- 230000015572 biosynthetic process Effects 0.000 description 10
- 239000001768 carboxy methyl cellulose Substances 0.000 description 10
- 238000005755 formation reaction Methods 0.000 description 10
- 229920002647 polyamide Polymers 0.000 description 10
- ODGAOXROABLFNM-UHFFFAOYSA-N polynoxylin Chemical compound O=C.NC(N)=O ODGAOXROABLFNM-UHFFFAOYSA-N 0.000 description 10
- 229920002451 polyvinyl alcohol Polymers 0.000 description 10
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 9
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 230000002378 acidificating effect Effects 0.000 description 8
- 230000000875 corresponding effect Effects 0.000 description 8
- 229920000642 polymer Polymers 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- 239000011230 binding agent Substances 0.000 description 6
- 230000003247 decreasing effect Effects 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 239000000178 monomer Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 230000033458 reproduction Effects 0.000 description 5
- 239000004372 Polyvinyl alcohol Substances 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 229920003180 amino resin Polymers 0.000 description 4
- -1 butyl benzyl adi-pate Chemical compound 0.000 description 4
- 239000012065 filter cake Substances 0.000 description 4
- 230000007935 neutral effect Effects 0.000 description 4
- 206010001497 Agitation Diseases 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 241001391944 Commicarpus scandens Species 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000013019 agitation Methods 0.000 description 3
- 239000000084 colloidal system Substances 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 150000002790 naphthalenes Chemical class 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- DHBXNPKRAUYBTH-UHFFFAOYSA-N 1,1-ethanedithiol Chemical compound CC(S)S DHBXNPKRAUYBTH-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- YLZSIUVOIFJGQZ-UHFFFAOYSA-N bis[4-(dimethylamino)phenyl]methanol Chemical compound C1=CC(N(C)C)=CC=C1C(O)C1=CC=C(N(C)C)C=C1 YLZSIUVOIFJGQZ-UHFFFAOYSA-N 0.000 description 2
- 235000012970 cakes Nutrition 0.000 description 2
- 239000013065 commercial product Substances 0.000 description 2
- 238000006482 condensation reaction Methods 0.000 description 2
- 238000004945 emulsification Methods 0.000 description 2
- 238000005538 encapsulation Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- VYMPLPIFKRHAAC-UHFFFAOYSA-N 1,2-ethanedithiol Chemical compound SCCS VYMPLPIFKRHAAC-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- DECACTMEFWAFRE-UHFFFAOYSA-N 6-o-benzyl 1-o-octyl hexanedioate Chemical compound CCCCCCCCOC(=O)CCCCC(=O)OCC1=CC=CC=C1 DECACTMEFWAFRE-UHFFFAOYSA-N 0.000 description 1
- 229930185605 Bisphenol Natural products 0.000 description 1
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 1
- XTJFFFGAUHQWII-UHFFFAOYSA-N Dibutyl adipate Chemical compound CCCCOC(=O)CCCCC(=O)OCCCC XTJFFFGAUHQWII-UHFFFAOYSA-N 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- 238000012695 Interfacial polymerization Methods 0.000 description 1
- 229920000877 Melamine resin Polymers 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 229920002396 Polyurea Polymers 0.000 description 1
- YSMRWXYRXBRSND-UHFFFAOYSA-N TOTP Chemical compound CC1=CC=CC=C1OP(=O)(OC=1C(=CC=CC=1)C)OC1=CC=CC=C1C YSMRWXYRXBRSND-UHFFFAOYSA-N 0.000 description 1
- 241001422033 Thestylus Species 0.000 description 1
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000003849 aromatic solvent Substances 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
- 235000010290 biphenyl Nutrition 0.000 description 1
- 150000004074 biphenyls Chemical class 0.000 description 1
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 238000005354 coacervation Methods 0.000 description 1
- 239000003240 coconut oil Substances 0.000 description 1
- 235000019864 coconut oil Nutrition 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000002385 cottonseed oil Substances 0.000 description 1
- 235000012343 cottonseed oil Nutrition 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 229940100539 dibutyl adipate Drugs 0.000 description 1
- 125000005442 diisocyanate group Chemical group 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 235000021463 dry cake Nutrition 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- IVJISJACKSSFGE-UHFFFAOYSA-N formaldehyde;1,3,5-triazine-2,4,6-triamine Chemical compound O=C.NC1=NC(N)=NC(N)=N1 IVJISJACKSSFGE-UHFFFAOYSA-N 0.000 description 1
- SLGWESQGEUXWJQ-UHFFFAOYSA-N formaldehyde;phenol Chemical compound O=C.OC1=CC=CC=C1 SLGWESQGEUXWJQ-UHFFFAOYSA-N 0.000 description 1
- 238000009472 formulation Methods 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
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000003209 petroleum derivative Substances 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 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
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- CMXPERZAMAQXSF-UHFFFAOYSA-M sodium;1,4-bis(2-ethylhexoxy)-1,4-dioxobutane-2-sulfonate;1,8-dihydroxyanthracene-9,10-dione Chemical compound [Na+].O=C1C2=CC=CC(O)=C2C(=O)C2=C1C=CC=C2O.CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC CMXPERZAMAQXSF-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 235000015096 spirit Nutrition 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- ZJHHPAUQMCHPRB-UHFFFAOYSA-N urea urea Chemical compound NC(N)=O.NC(N)=O ZJHHPAUQMCHPRB-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 229920002554 vinyl polymer Polymers 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
- B01J13/18—In situ polymerisation with all reactants being present in the same phase
-
- 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)
- Color Printing (AREA)
- Manufacturing Of Micro-Capsules (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US50541574A | 1974-09-12 | 1974-09-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1052195A true CA1052195A (en) | 1979-04-10 |
Family
ID=24010214
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA230,762A Expired CA1052195A (en) | 1974-09-12 | 1975-07-04 | Production of dual walled microcapsules by reducing ph to polymerize aminoaldehyde precondensate |
Country Status (11)
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5547139A (en) * | 1978-09-30 | 1980-04-03 | Mitsubishi Paper Mills Ltd | Improved small capsule |
| NZ196601A (en) | 1980-04-08 | 1982-12-21 | Wiggins Teape Group Ltd | Production of microcapsules |
| JPS56144739A (en) * | 1980-04-10 | 1981-11-11 | Mitsubishi Paper Mills Ltd | Preparation of microcapsule |
| US4601863A (en) * | 1984-02-09 | 1986-07-22 | Kanzaki Paper Manufacturing Co., Ltd. | Process for producing powder of microcapsules |
| JPS60237864A (ja) * | 1984-05-08 | 1985-11-26 | Mitsubishi Electric Corp | 高電圧サイリスタ変換装置 |
| DE60100150T2 (de) * | 2000-01-13 | 2004-02-19 | Kureha Kagaku Kogyo K.K. | Mikrokapsel und sein Herstellungsverfahren |
| EP1658131B1 (en) * | 2003-08-26 | 2016-09-21 | Devan-Micropolis SA | Double walled microcapsules with an outer thermoplastic wall and application process thereof |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH540715A (de) * | 1970-05-26 | 1973-10-15 | Ciba Geigy Ag | Verfahren zur Einkapselung von in einer Flüssigkeit fein verteilter Substanz |
| DE2323243C3 (de) * | 1973-05-09 | 1980-02-28 | Robert Bosch Gmbh, 7000 Stuttgart | Verfahren zur Herstellung einer verschleißfesten Hartmetallschicht auf einem Metallgegenstand, insbesondere auf der Schneide eines Stahl-Sägeblattes |
| JPS5813212B2 (ja) * | 1973-07-17 | 1983-03-12 | 富士写真フイルム株式会社 | マイクロカプセル ノ セイゾウホウ |
-
1975
- 1975-07-04 CA CA230,762A patent/CA1052195A/en not_active Expired
- 1975-07-11 AU AU82961/75A patent/AU502339B2/en not_active Expired
- 1975-07-16 ZA ZA00754567A patent/ZA754567B/xx unknown
- 1975-08-20 GB GB34627/75A patent/GB1502440A/en not_active Expired
- 1975-08-20 JP JP10107475A patent/JPS5413874B2/ja not_active Expired
- 1975-08-21 DE DE2537238A patent/DE2537238C2/de not_active Expired
- 1975-08-29 BE BE159591A patent/BE832897A/xx not_active IP Right Cessation
- 1975-09-03 FR FR7526985A patent/FR2284366A1/fr active Granted
- 1975-09-08 CH CH1163775A patent/CH615363A5/de not_active IP Right Cessation
- 1975-09-09 IT IT51255/75A patent/IT1047055B/it active
- 1975-09-12 NL NL7510799A patent/NL7510799A/xx not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| DE2537238A1 (de) | 1976-03-25 |
| JPS5147578A (enrdf_load_stackoverflow) | 1976-04-23 |
| IT1047055B (it) | 1980-09-10 |
| NL7510799A (nl) | 1976-03-16 |
| AU502339B2 (en) | 1979-07-19 |
| AU8296175A (en) | 1977-01-13 |
| DE2537238C2 (de) | 1984-11-08 |
| ZA754567B (en) | 1976-06-30 |
| FR2284366B1 (enrdf_load_stackoverflow) | 1983-04-22 |
| GB1502440A (en) | 1978-03-01 |
| CH615363A5 (en) | 1980-01-31 |
| BE832897A (fr) | 1975-12-16 |
| JPS5413874B2 (enrdf_load_stackoverflow) | 1979-06-02 |
| FR2284366A1 (fr) | 1976-04-09 |
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