CA1108944A - Capsule manufacture - Google Patents

Capsule manufacture

Info

Publication number: CA1108944A
Authority: CA; Canada
Prior art keywords: poly; urea; maleic anhydride; formaldehyde; aqueous
Prior art date: 1976-12-30
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

Application number

CA288,871A

Other languages

English (en)

French (fr)

Inventor

Robert W. Brown

Peter L. Foris

Paul S. Phillips, Jr.

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Appvion LLC

Original Assignee

Appleton Papers Inc

Priority date (The priority date 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 date listed.)

1976-12-30

Filing date

1977-10-17

Publication date

1981-09-15

1976-12-30 Priority claimed from US05/755,831 external-priority patent/US4089802A/en

1977-10-17 Application filed by Appleton Papers Inc filed Critical Appleton Papers Inc

1981-09-15 Application granted granted Critical

1981-09-15 Publication of CA1108944A publication Critical patent/CA1108944A/en

Status Expired legal-status Critical Current

Links

239000002775 capsule Substances 0.000 title claims abstract description 130
238000004519 manufacturing process Methods 0.000 title claims abstract description 53
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims abstract description 149
239000000463 material Substances 0.000 claims abstract description 81
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims abstract description 64
239000004202 carbamide Substances 0.000 claims abstract description 64
238000000034 method Methods 0.000 claims abstract description 52
230000008569 process Effects 0.000 claims abstract description 46
238000006116 polymerization reaction Methods 0.000 claims abstract description 33
229920000642 polymer Polymers 0.000 claims abstract description 28
238000009833 condensation Methods 0.000 claims abstract description 14
230000005494 condensation Effects 0.000 claims abstract description 14
238000006243 chemical reaction Methods 0.000 claims abstract description 13
239000007791 liquid phase Substances 0.000 claims abstract description 9
238000005191 phase separation Methods 0.000 claims abstract description 8
239000000243 solution Substances 0.000 claims description 64
239000003607 modifier Substances 0.000 claims description 60
229960004279 formaldehyde Drugs 0.000 claims description 48
235000019256 formaldehyde Nutrition 0.000 claims description 46
-1 poly(methyl vinyl Chemical group 0.000 claims description 43
GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 claims description 40
239000000839 emulsion Substances 0.000 claims description 25
239000012071 phase Substances 0.000 claims description 25
239000000047 product Substances 0.000 claims description 22
239000011162 core material Substances 0.000 claims description 19
239000007788 liquid Substances 0.000 claims description 18
229920002125 Sokalan® Polymers 0.000 claims description 17
239000002245 particle Substances 0.000 claims description 16
239000007787 solid Substances 0.000 claims description 15
229920001807 Urea-formaldehyde Polymers 0.000 claims description 13
230000015572 biosynthetic process Effects 0.000 claims description 13
239000007864 aqueous solution Substances 0.000 claims description 12
WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 claims description 7
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 7
229920002554 vinyl polymer Polymers 0.000 claims description 7
ODGAOXROABLFNM-UHFFFAOYSA-N polynoxylin Chemical compound O=C.NC(N)=O ODGAOXROABLFNM-UHFFFAOYSA-N 0.000 claims description 6
LNTHITQWFMADLM-UHFFFAOYSA-N gallic acid Chemical compound OC(=O)C1=CC(O)=C(O)C(O)=C1 LNTHITQWFMADLM-UHFFFAOYSA-N 0.000 claims description 4
OIPPWFOQEKKFEE-UHFFFAOYSA-N orcinol Chemical compound CC1=CC(O)=CC(O)=C1 OIPPWFOQEKKFEE-UHFFFAOYSA-N 0.000 claims description 4
239000000654 additive Substances 0.000 claims description 3
230000000996 additive effect Effects 0.000 claims description 3
229940074391 gallic acid Drugs 0.000 claims description 2
235000004515 gallic acid Nutrition 0.000 claims description 2
150000001875 compounds Chemical class 0.000 claims 2
QUBQYFYWUJJAAK-UHFFFAOYSA-N oxymethurea Chemical compound OCNC(=O)NCO QUBQYFYWUJJAAK-UHFFFAOYSA-N 0.000 abstract description 31
239000003981 vehicle Substances 0.000 abstract description 30
229950005308 oxymethurea Drugs 0.000 abstract description 18
239000003094 microcapsule Substances 0.000 abstract description 10
239000012895 dilution Substances 0.000 abstract description 9
238000010790 dilution Methods 0.000 abstract description 9
230000000694 effects Effects 0.000 abstract description 7
238000005538 encapsulation Methods 0.000 abstract description 7
238000011065 in-situ storage Methods 0.000 abstract description 4
229920000867 polyelectrolyte Polymers 0.000 abstract description 4
150000001338 aliphatic hydrocarbons Chemical class 0.000 abstract description 3
238000006068 polycondensation reaction Methods 0.000 abstract description 2
239000008135 aqueous vehicle Substances 0.000 abstract 1
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 51
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 48
229940044600 maleic anhydride Drugs 0.000 description 39
229960001755 resorcinol Drugs 0.000 description 19
235000011121 sodium hydroxide Nutrition 0.000 description 17
238000012360 testing method Methods 0.000 description 17
206010001497 Agitation Diseases 0.000 description 13
238000013019 agitation Methods 0.000 description 13
239000000975 dye Substances 0.000 description 10
238000005755 formation reaction Methods 0.000 description 9
238000003756 stirring Methods 0.000 description 9
239000011248 coating agent Substances 0.000 description 8
238000000576 coating method Methods 0.000 description 8
239000007858 starting material Substances 0.000 description 8
239000000203 mixture Substances 0.000 description 7
229920002451 polyvinyl alcohol Polymers 0.000 description 7
241000254173 Coleoptera Species 0.000 description 6
238000006482 condensation reaction Methods 0.000 description 6
ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 6
125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 5
229920005989 resin Polymers 0.000 description 5
239000011347 resin Substances 0.000 description 5
230000008901 benefit Effects 0.000 description 4
239000008098 formaldehyde solution Substances 0.000 description 4
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
239000012615 aggregate Substances 0.000 description 3
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
229940083608 sodium hydroxide Drugs 0.000 description 3
YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
229920002472 Starch Polymers 0.000 description 2
239000002253 acid Substances 0.000 description 2
239000011230 binding agent Substances 0.000 description 2
238000009835 boiling Methods 0.000 description 2
230000008859 change Effects 0.000 description 2
230000018109 developmental process Effects 0.000 description 2
238000004945 emulsification Methods 0.000 description 2
UPBDXRPQPOWRKR-UHFFFAOYSA-N furan-2,5-dione;methoxyethene Chemical compound COC=C.O=C1OC(=O)C=C1 UPBDXRPQPOWRKR-UHFFFAOYSA-N 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
230000002209 hydrophobic effect Effects 0.000 description 2
239000004615 ingredient Substances 0.000 description 2
OSWPMRLSEDHDFF-UHFFFAOYSA-N methyl salicylate Chemical compound COC(=O)C1=CC=CC=C1O OSWPMRLSEDHDFF-UHFFFAOYSA-N 0.000 description 2
239000003921 oil Substances 0.000 description 2
235000019198 oils Nutrition 0.000 description 2
230000000379 polymerizing effect Effects 0.000 description 2
239000000376 reactant Substances 0.000 description 2
239000002002 slurry Substances 0.000 description 2
239000002904 solvent Substances 0.000 description 2
239000000758 substrate Substances 0.000 description 2
229940045136 urea Drugs 0.000 description 2
239000000080 wetting agent Substances 0.000 description 2
229940100445 wheat starch 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
KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical class [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 1
239000005995 Aluminium silicate Substances 0.000 description 1
235000016068 Berberis vulgaris Nutrition 0.000 description 1
241000335053 Beta vulgaris Species 0.000 description 1
241000661938 Capsus Species 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
229920002261 Corn starch Polymers 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
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
239000005977 Ethylene Substances 0.000 description 1
229920000881 Modified starch Polymers 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
230000002411 adverse Effects 0.000 description 1
230000032683 aging Effects 0.000 description 1
235000012211 aluminium silicate Nutrition 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
150000008064 anhydrides Chemical group 0.000 description 1
239000010425 asbestos Substances 0.000 description 1
230000009286 beneficial effect Effects 0.000 description 1
230000003115 biocidal effect Effects 0.000 description 1
FFPOAADRIDYUKW-UHFFFAOYSA-N buta-1,3-diene;furan-2,5-dione Chemical compound C=CC=C.O=C1OC(=O)C=C1 FFPOAADRIDYUKW-UHFFFAOYSA-N 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
239000001913 cellulose Substances 0.000 description 1
229920002678 cellulose Polymers 0.000 description 1
239000002801 charged material Substances 0.000 description 1
229920001429 chelating resin Polymers 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000004927 clay Substances 0.000 description 1
239000008199 coating composition Substances 0.000 description 1
229940110456 cocoa butter Drugs 0.000 description 1
235000019868 cocoa butter Nutrition 0.000 description 1
239000000084 colloidal system Substances 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
239000002131 composite material Substances 0.000 description 1
230000000332 continued effect Effects 0.000 description 1
229920001577 copolymer Polymers 0.000 description 1
239000007771 core particle Substances 0.000 description 1
239000008120 corn starch Substances 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
230000008021 deposition Effects 0.000 description 1
230000001627 detrimental effect Effects 0.000 description 1
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
238000004821 distillation Methods 0.000 description 1
239000002001 electrolyte material Substances 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
230000001804 emulsifying effect Effects 0.000 description 1
230000001747 exhibiting effect Effects 0.000 description 1
239000003337 fertilizer Substances 0.000 description 1
239000002657 fibrous material Substances 0.000 description 1
239000007888 film coating Substances 0.000 description 1
238000009501 film coating Methods 0.000 description 1
238000001914 filtration Methods 0.000 description 1
229940013317 fish oils Drugs 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
235000019634 flavors Nutrition 0.000 description 1
239000003205 fragrance Substances 0.000 description 1
239000007789 gas Substances 0.000 description 1
239000011521 glass Substances 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
230000006872 improvement Effects 0.000 description 1
125000001041 indolyl group Chemical group 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
239000002917 insecticide Substances 0.000 description 1
239000002198 insoluble material Substances 0.000 description 1
150000002500 ions Chemical class 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
FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
230000007246 mechanism Effects 0.000 description 1
239000002609 medium Substances 0.000 description 1
229910044991 metal oxide Inorganic materials 0.000 description 1
229960001047 methyl salicylate Drugs 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
239000011707 mineral Substances 0.000 description 1
235000010446 mineral oil Nutrition 0.000 description 1
239000002480 mineral oil Substances 0.000 description 1
238000002156 mixing Methods 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
235000019426 modified starch Nutrition 0.000 description 1
235000008390 olive oil Nutrition 0.000 description 1
239000004006 olive oil Substances 0.000 description 1
239000003973 paint Substances 0.000 description 1
230000035699 permeability Effects 0.000 description 1
239000000049 pigment Substances 0.000 description 1
229920000058 polyacrylate Polymers 0.000 description 1
229920000136 polysorbate Polymers 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
230000001681 protective effect Effects 0.000 description 1
230000036647 reaction Effects 0.000 description 1
229910052895 riebeckite Inorganic materials 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
239000011343 solid material Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
230000007704 transition Effects 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G12/00—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen
- C08G12/02—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes
- C08G12/04—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with acyclic or carbocyclic compounds
- C08G12/10—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with acyclic or carbocyclic compounds with acyclic compounds having the moiety X=C(—N<)2 in which X is O, S or —N
- C08G12/12—Ureas; Thioureas
- 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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Dispersion Chemistry (AREA)
Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Manufacturing Of Micro-Capsules (AREA)
Color Printing (AREA)

CA288,871A 1976-12-30 1977-10-17 Capsule manufacture Expired CA1108944A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US05/755,831 US4089802A (en)	1974-07-10	1976-12-30	Capsule manufacture
US755,831		1985-07-15

Publications (1)

Publication Number	Publication Date
CA1108944A true CA1108944A (en)	1981-09-15

Family

ID=25040823

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA288,871A Expired CA1108944A (en)	1976-12-30	1977-10-17	Capsule manufacture

Country Status (6)

Country	Link
JP (1)	JPS6012904B2 (de)
AT (1)	AT361894B (de)
AU (1)	AU517421B2 (de)
BE (1)	BE862372R (de)
CA (1)	CA1108944A (de)
ZA (1)	ZA777149B (de)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS57135038A (en) *	1981-02-13	1982-08-20	Kanzaki Paper Mfg Co Ltd	Preparation of microcapsule
JPS6294703U (de) *	1985-12-04	1987-06-17
JP6827433B2 (ja)	2018-03-02	2021-02-10	株式会社東芝	半導体装置

1977
- 1977-10-17 CA CA288,871A patent/CA1108944A/en not_active Expired
- 1977-12-01 ZA ZA00777149A patent/ZA777149B/xx unknown
- 1977-12-19 AU AU31766/77A patent/AU517421B2/en not_active Expired
- 1977-12-22 JP JP52153660A patent/JPS6012904B2/ja not_active Expired
- 1977-12-27 AT AT931277A patent/AT361894B/de not_active IP Right Cessation
- 1977-12-27 BE BE183891A patent/BE862372R/xx not_active IP Right Cessation

Also Published As

Publication number	Publication date
AU517421B2 (en)	1981-07-30
AU3176677A (en)	1979-06-28
JPS5384882A (en)	1978-07-26
ATA931277A (de)	1980-09-15
BE862372R (fr)	1978-04-14
JPS6012904B2 (ja)	1985-04-04
AT361894B (de)	1981-04-10
ZA777149B (en)	1978-09-27

Legal Events

Date	Code	Title	Description
1998-09-15	MKEX	Expiry

Publication	Publication Date	Title
US4089802A (en)	1978-05-16	Capsule manufacture
US4100103A (en)	1978-07-11	Capsule manufacture
FI64898C (fi)	1984-02-10	Foerfarande foer inkapsling av finfoerdelat material och anvaendning av de medelst foerfarandet erhaollna mikrokapslarna
CA1149239A (en)	1983-07-05	Process for preparation of microcapsules by condensing melamine-formaldehyde precondensate in presence of polymer possessing sulfonic acid groups
US4396670A (en)	1983-08-02	Process for the production of microcapsules
US4233178A (en)	1980-11-11	Micro-capsules and method for their production
US5118756A (en)	1992-06-02	Reaction system modifier suitable for use in the productions of microcapsules
US4525520A (en)	1985-06-25	Method of preparing microcapsules
US3755190A (en)	1973-08-28	Capsule manufacture
US4201404A (en)	1980-05-06	Pressure-sensitive marking materials
US4729792A (en)	1988-03-08	Microcapsules, printing inks and their production
EP0492793A1 (de)	1992-07-01	Melamine-Formaldehyde Mikroverkapselung in wässriger Lösung welche eine hoche Konzentration organischer Lösungsmittel enthält
US3607775A (en)	1971-09-21	Process for encapsulating minute particles by use of autogenously polymerizable capsule wall material
US4753968A (en)	1988-06-28	Process for preparing microcapsules
US4089834A (en)	1978-05-16	Water-resistant micro-capsular opacifier system and products
KR840001591B1 (ko)	1984-10-11	압력-민감성 기록지용 미세캡슐의 제조방법
CA1108942A (en)	1981-09-15	Capsule manufacture
US5196149A (en)	1993-03-23	Preparation of high solids, low viscosity carbonless paper gelatin base microcapsules
US4000345A (en)	1976-12-28	Substrate having coating thereon comprising microcapsular opacifying agents, and method of preparing same
KR100381370B1 (ko)	2003-04-23	마이크로 캡슐의 제조방법
US5064470A (en)	1991-11-12	High solids, low viscosity carbonless paper gelatin base microcapsule system
JPS6012904B2 (ja)	1985-04-04	微小カプセルの製造方法
NL8500662A (nl)	1985-07-01	Werkwijze voor het bereiden in massa van microcapsules met een wandje van polymeer materiaal.
JPS6351877B2 (de)	1988-10-17
JPS62250943A (ja)	1987-10-31	マイクロカプセルの製造方法