CA1104881A - Methode de production de microcapsules a paroi d'encapsulage secondaires, et microcapsules ainsi obtenues - Google Patents

Methode de production de microcapsules a paroi d'encapsulage secondaires, et microcapsules ainsi obtenues

Info

Publication number: CA1104881A
Authority: CA; Canada
Prior art keywords: microcapsules; capsule wall; aqueous dispersion; aldehyde; condensation polymer
Prior art date: 1977-06-24
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

CA302,327A

Other languages

English (en)

Inventor

Yu-Sun Lee

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.)

Mead Corp

Original Assignee

Mead Corp

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.)

1977-06-24

Filing date

1978-05-01

Publication date

1981-07-14

1978-05-01 Application filed by Mead Corp filed Critical Mead Corp

1981-07-14 Application granted granted Critical

1981-07-14 Publication of CA1104881A publication Critical patent/CA1104881A/fr

Status Expired legal-status Critical Current

Links

239000003094 microcapsule Substances 0.000 title claims abstract description 142
239000002775 capsule Substances 0.000 title claims abstract description 63
238000000034 method Methods 0.000 title claims abstract description 31
230000008569 process Effects 0.000 title claims abstract description 26
239000006185 dispersion Substances 0.000 claims abstract description 52
235000010977 hydroxypropyl cellulose Nutrition 0.000 claims abstract description 41
239000000463 material Substances 0.000 claims abstract description 41
229920002153 Hydroxypropyl cellulose Polymers 0.000 claims abstract description 38
150000001299 aldehydes Chemical class 0.000 claims abstract description 38
229920000642 polymer Polymers 0.000 claims abstract description 37
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract description 35
238000009833 condensation Methods 0.000 claims abstract description 35
230000005494 condensation Effects 0.000 claims abstract description 35
239000000203 mixture Substances 0.000 claims abstract description 33
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 31
239000001863 hydroxypropyl cellulose Substances 0.000 claims abstract description 27
239000008199 coating composition Substances 0.000 claims abstract description 24
LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 claims abstract description 20
238000002156 mixing Methods 0.000 claims abstract description 20
HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 claims abstract description 19
239000003431 cross linking reagent Substances 0.000 claims abstract description 18
238000004519 manufacturing process Methods 0.000 claims abstract description 17
239000007795 chemical reaction product Substances 0.000 claims abstract description 14
239000002243 precursor Substances 0.000 claims abstract description 14
WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 claims abstract description 11
SXRSQZLOMIGNAQ-UHFFFAOYSA-N Glutaraldehyde Chemical compound O=CCCCC=O SXRSQZLOMIGNAQ-UHFFFAOYSA-N 0.000 claims abstract description 10
229940015043 glyoxal Drugs 0.000 claims abstract description 10
IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 claims abstract description 9
239000012948 isocyanate Substances 0.000 claims abstract description 8
150000002513 isocyanates Chemical class 0.000 claims abstract description 8
238000007757 hot melt coating Methods 0.000 claims abstract description 7
150000001263 acyl chlorides Chemical class 0.000 claims abstract description 6
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical class ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims abstract description 6
125000002947 alkylene group Chemical group 0.000 claims abstract description 5
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical class ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims abstract description 5
238000001914 filtration Methods 0.000 claims abstract description 3
229940071676 hydroxypropylcellulose Drugs 0.000 claims abstract 12
230000001376 precipitating effect Effects 0.000 claims abstract 7
GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 claims description 50
239000000123 paper Substances 0.000 claims description 48
239000003921 oil Substances 0.000 claims description 46
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 41
238000000576 coating method Methods 0.000 claims description 28
239000000243 solution Substances 0.000 claims description 27
239000011248 coating agent Substances 0.000 claims description 21
239000000758 substrate Substances 0.000 claims description 20
239000002199 base oil Substances 0.000 claims description 18
239000002245 particle Substances 0.000 claims description 12
QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims description 8
239000007864 aqueous solution Substances 0.000 claims description 8
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 claims description 8
YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 claims description 8
COVFEVWNJUOYRL-UHFFFAOYSA-N digallic acid Chemical compound OC(=O)C1=CC(O)=C(O)C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)=C1 COVFEVWNJUOYRL-UHFFFAOYSA-N 0.000 claims description 8
RRAFCDWBNXTKKO-UHFFFAOYSA-N eugenol Chemical compound COC1=CC(CC=C)=CC=C1O RRAFCDWBNXTKKO-UHFFFAOYSA-N 0.000 claims description 8
LHGVFZTZFXWLCP-UHFFFAOYSA-N guaiacol Chemical compound COC1=CC=CC=C1O LHGVFZTZFXWLCP-UHFFFAOYSA-N 0.000 claims description 8
RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 claims description 8
QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 claims description 8
238000001035 drying Methods 0.000 claims description 7
239000012943 hotmelt Substances 0.000 claims description 7
239000007788 liquid Substances 0.000 claims description 7
239000005056 polyisocyanate Substances 0.000 claims description 7
229920001228 polyisocyanate Polymers 0.000 claims description 7
239000002253 acid Substances 0.000 claims description 6
WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 claims description 6
239000007787 solid Substances 0.000 claims description 6
-1 naphtha-lenediols Chemical compound 0.000 claims description 5
TUSDEZXZIZRFGC-UHFFFAOYSA-N 1-O-galloyl-3,6-(R)-HHDP-beta-D-glucose Natural products OC1C(O2)COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC1C(O)C2OC(=O)C1=CC(O)=C(O)C(O)=C1 TUSDEZXZIZRFGC-UHFFFAOYSA-N 0.000 claims description 4
VGVRPFIJEJYOFN-UHFFFAOYSA-N 2,3,4,6-tetrachlorophenol Chemical class OC1=C(Cl)C=C(Cl)C(Cl)=C1Cl VGVRPFIJEJYOFN-UHFFFAOYSA-N 0.000 claims description 4
NPBVQXIMTZKSBA-UHFFFAOYSA-N Chavibetol Natural products COC1=CC=C(CC=C)C=C1O NPBVQXIMTZKSBA-UHFFFAOYSA-N 0.000 claims description 4
229920002707 Digallic acid Polymers 0.000 claims description 4
239000005770 Eugenol Substances 0.000 claims description 4
239000001263 FEMA 3042 Substances 0.000 claims description 4
LRBQNJMCXXYXIU-PPKXGCFTSA-N Penta-digallate-beta-D-glucose Natural products OC1=C(O)C(O)=CC(C(=O)OC=2C(=C(O)C=C(C=2)C(=O)OC[C@@H]2[C@H]([C@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)O2)OC(=O)C=2C=C(OC(=O)C=3C=C(O)C(O)=C(O)C=3)C(O)=C(O)C=2)O)=C1 LRBQNJMCXXYXIU-PPKXGCFTSA-N 0.000 claims description 4
JPYHHZQJCSQRJY-UHFFFAOYSA-N Phloroglucinol Natural products CCC=CCC=CCC=CCC=CCCCCC(=O)C1=C(O)C=C(O)C=C1O JPYHHZQJCSQRJY-UHFFFAOYSA-N 0.000 claims description 4
UVMRYBDEERADNV-UHFFFAOYSA-N Pseudoeugenol Natural products COC1=CC(C(C)=C)=CC=C1O UVMRYBDEERADNV-UHFFFAOYSA-N 0.000 claims description 4
239000011230 binding agent Substances 0.000 claims description 4
229960002217 eugenol Drugs 0.000 claims description 4
LRBQNJMCXXYXIU-QWKBTXIPSA-N gallotannic acid Chemical compound OC1=C(O)C(O)=CC(C(=O)OC=2C(=C(O)C=C(C=2)C(=O)OC[C@H]2[C@@H]([C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)O2)OC(=O)C=2C=C(OC(=O)C=3C=C(O)C(O)=C(O)C=3)C(O)=C(O)C=2)O)=C1 LRBQNJMCXXYXIU-QWKBTXIPSA-N 0.000 claims description 4
229960001867 guaiacol Drugs 0.000 claims description 4
150000004780 naphthols Chemical class 0.000 claims description 4
QCDYQQDYXPDABM-UHFFFAOYSA-N phloroglucinol Chemical compound OC1=CC(O)=CC(O)=C1 QCDYQQDYXPDABM-UHFFFAOYSA-N 0.000 claims description 4
229960001553 phloroglucinol Drugs 0.000 claims description 4
235000015523 tannic acid Nutrition 0.000 claims description 4
229920002258 tannic acid Polymers 0.000 claims description 4
229940033123 tannic acid Drugs 0.000 claims description 4
DIRJJQCGNXNXPL-UHFFFAOYSA-N 2-(2-hydroxyphenyl)benzene-1,3-diol Chemical class OC1=CC=CC=C1C1=C(O)C=CC=C1O DIRJJQCGNXNXPL-UHFFFAOYSA-N 0.000 claims description 3
229940079877 pyrogallol Drugs 0.000 claims description 3
238000007864 suspending Methods 0.000 claims description 3
NXPPAOGUKPJVDI-UHFFFAOYSA-N naphthalene-1,2-diol Chemical class C1=CC=CC2=C(O)C(O)=CC=C21 NXPPAOGUKPJVDI-UHFFFAOYSA-N 0.000 claims description 2
LNTHITQWFMADLM-UHFFFAOYSA-N gallic acid Chemical compound OC(=O)C1=CC(O)=C(O)C(O)=C1 LNTHITQWFMADLM-UHFFFAOYSA-N 0.000 claims 6
IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 claims 6
229940074391 gallic acid Drugs 0.000 claims 3
235000004515 gallic acid Nutrition 0.000 claims 3
150000003739 xylenols Chemical class 0.000 claims 3
238000001816 cooling Methods 0.000 claims 1
238000010438 heat treatment Methods 0.000 claims 1
238000002360 preparation method Methods 0.000 abstract description 6
238000009740 moulding (composite fabrication) Methods 0.000 description 13
239000012071 phase Substances 0.000 description 13
238000006243 chemical reaction Methods 0.000 description 9
150000001875 compounds Chemical class 0.000 description 9
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
230000000052 comparative effect Effects 0.000 description 7
239000011541 reaction mixture Substances 0.000 description 7
238000003756 stirring Methods 0.000 description 7
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
239000008346 aqueous phase Substances 0.000 description 6
235000019256 formaldehyde Nutrition 0.000 description 6
229960004279 formaldehyde Drugs 0.000 description 6
239000002244 precipitate Substances 0.000 description 6
QTKIQLNGOKOPOE-UHFFFAOYSA-N 1,1'-biphenyl;propane Chemical group CCC.C1=CC=CC=C1C1=CC=CC=C1 QTKIQLNGOKOPOE-UHFFFAOYSA-N 0.000 description 5
230000015572 biosynthetic process Effects 0.000 description 5
239000000376 reactant Substances 0.000 description 5
WNZQDUSMALZDQF-UHFFFAOYSA-N 2-benzofuran-1(3H)-one Chemical compound C1=CC=C2C(=O)OCC2=C1 WNZQDUSMALZDQF-UHFFFAOYSA-N 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
239000000839 emulsion Substances 0.000 description 4
229920001223 polyethylene glycol Polymers 0.000 description 4
229960000583 acetic acid Drugs 0.000 description 3
230000002776 aggregation Effects 0.000 description 3
238000004220 aggregation Methods 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
238000004132 cross linking Methods 0.000 description 3
239000003995 emulsifying agent Substances 0.000 description 3
239000004615 ingredient Substances 0.000 description 3
229920003986 novolac Polymers 0.000 description 3
239000002904 solvent Substances 0.000 description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
241000410737 Verasper moseri Species 0.000 description 2
239000004202 carbamide Substances 0.000 description 2
238000005354 coacervation Methods 0.000 description 2
239000012153 distilled water Substances 0.000 description 2
239000012065 filter cake Substances 0.000 description 2
FWQHNLCNFPYBCA-UHFFFAOYSA-N fluoran Chemical compound C12=CC=CC=C2OC2=CC=CC=C2C11OC(=O)C2=CC=CC=C21 FWQHNLCNFPYBCA-UHFFFAOYSA-N 0.000 description 2
239000008098 formaldehyde solution Substances 0.000 description 2
238000009472 formulation Methods 0.000 description 2
229960000587 glutaral Drugs 0.000 description 2
VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
230000006872 improvement Effects 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
150000002989 phenols Chemical class 0.000 description 2
238000001556 precipitation Methods 0.000 description 2
239000000047 product Substances 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
QKOWXXDOHMJOMQ-UHFFFAOYSA-N 1,3,5-tris(6-isocyanatohexyl)biuret Chemical compound O=C=NCCCCCCNC(=O)N(CCCCCCN=C=O)C(=O)NCCCCCCN=C=O QKOWXXDOHMJOMQ-UHFFFAOYSA-N 0.000 description 1
DGXAGETVRDOQFP-UHFFFAOYSA-N 2,6-dihydroxybenzaldehyde Chemical compound OC1=CC=CC(O)=C1C=O DGXAGETVRDOQFP-UHFFFAOYSA-N 0.000 description 1
241000272165 Charadriidae Species 0.000 description 1
238000006873 Coates reaction Methods 0.000 description 1
241000518994 Conta Species 0.000 description 1
229920000084 Gum arabic Polymers 0.000 description 1
239000005057 Hexamethylene diisocyanate Substances 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
229920001730 Moisture cure polyurethane Polymers 0.000 description 1
101100270435 Mus musculus Arhgef12 gene Proteins 0.000 description 1
239000002202 Polyethylene glycol Substances 0.000 description 1
235000015076 Shorea robusta Nutrition 0.000 description 1
244000166071 Shorea robusta Species 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 1
239000000205 acacia gum Substances 0.000 description 1
230000009471 action Effects 0.000 description 1
239000000853 adhesive Substances 0.000 description 1
230000001070 adhesive effect Effects 0.000 description 1
238000013019 agitation Methods 0.000 description 1
RGCKGOZRHPZPFP-UHFFFAOYSA-N alizarin Chemical compound C1=CC=C2C(=O)C3=C(O)C(O)=CC=C3C(=O)C2=C1 RGCKGOZRHPZPFP-UHFFFAOYSA-N 0.000 description 1
239000003125 aqueous solvent Substances 0.000 description 1
235000019568 aromas Nutrition 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
230000008901 benefit Effects 0.000 description 1
235000010290 biphenyl Nutrition 0.000 description 1
150000004074 biphenyls Chemical class 0.000 description 1
OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical compound NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 description 1
239000004359 castor oil Substances 0.000 description 1
235000019438 castor oil Nutrition 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
239000001913 cellulose Substances 0.000 description 1
235000010980 cellulose Nutrition 0.000 description 1
229940106135 cellulose Drugs 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
230000002844 continuous effect Effects 0.000 description 1
239000013078 crystal Substances 0.000 description 1
230000001419 dependent effect Effects 0.000 description 1
230000001627 detrimental effect Effects 0.000 description 1
238000009826 distribution Methods 0.000 description 1
239000003814 drug Substances 0.000 description 1
230000009977 dual effect Effects 0.000 description 1
230000000694 effects Effects 0.000 description 1
238000004945 emulsification Methods 0.000 description 1
238000005538 encapsulation Methods 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
230000001747 exhibiting effect Effects 0.000 description 1
239000004744 fabric Substances 0.000 description 1
239000000835 fiber Substances 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
235000013355 food flavoring agent Nutrition 0.000 description 1
SLGWESQGEUXWJQ-UHFFFAOYSA-N formaldehyde;phenol Chemical compound O=C.OC1=CC=CC=C1 SLGWESQGEUXWJQ-UHFFFAOYSA-N 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
239000011521 glass Substances 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
230000036541 health Effects 0.000 description 1
RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
238000003384 imaging method Methods 0.000 description 1
230000003993 interaction Effects 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
239000003350 kerosene Substances 0.000 description 1
150000002596 lactones Chemical class 0.000 description 1
239000004816 latex Substances 0.000 description 1
229920000126 latex Polymers 0.000 description 1
235000019988 mead Nutrition 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
238000003801 milling Methods 0.000 description 1
230000035699 permeability Effects 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
229920001568 phenolic resin Polymers 0.000 description 1
HCTVWSOKIJULET-LQDWTQKMSA-M phenoxymethylpenicillin potassium Chemical compound [K+].N([C@H]1[C@H]2SC([C@@H](N2C1=O)C([O-])=O)(C)C)C(=O)COC1=CC=CC=C1 HCTVWSOKIJULET-LQDWTQKMSA-M 0.000 description 1
239000002985 plastic film Substances 0.000 description 1
229920006255 plastic film Polymers 0.000 description 1
229920000136 polysorbate Polymers 0.000 description 1
239000000843 powder Substances 0.000 description 1
230000002028 premature Effects 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
230000009467 reduction Effects 0.000 description 1
239000002002 slurry Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
239000007921 spray Substances 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
230000002459 sustained effect Effects 0.000 description 1
238000003828 vacuum filtration Methods 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1

Classifications

- B—PERFORMING OPERATIONS; TRANSPORTING
- B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
- B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
- B41M5/00—Duplicating or marking methods; Sheet materials for use therein
- B41M5/124—Duplicating or marking methods; Sheet materials for use therein using pressure to make a masked colour visible, e.g. to make a coloured support visible, to create an opaque or transparent pattern, or to form colour by uniting colour-forming components
- B41M5/165—Duplicating or marking methods; Sheet materials for use therein using pressure to make a masked colour visible, e.g. to make a coloured support visible, to create an opaque or transparent pattern, or to form colour by uniting colour-forming components characterised by the use of microcapsules; Special solvents for incorporating the ingredients
- 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)
Dispersion Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Color Printing (AREA)
Manufacturing Of Micro-Capsules (AREA)

CA302,327A 1977-06-24 1978-05-01 Methode de production de microcapsules a paroi d'encapsulage secondaires, et microcapsules ainsi obtenues Expired CA1104881A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US80952177A	1977-06-24	1977-06-24
US809,521		1977-06-24

Publications (1)

Publication Number	Publication Date
CA1104881A true CA1104881A (fr)	1981-07-14

Family

ID=25201522

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA302,327A Expired CA1104881A (fr)	1977-06-24	1978-05-01	Methode de production de microcapsules a paroi d'encapsulage secondaires, et microcapsules ainsi obtenues

Country Status (4)

Country	Link
JP (1)	JPS5417377A (fr)
CA (1)	CA1104881A (fr)
DE (1)	DE2826939A1 (fr)
GB (1)	GB1603448A (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5346931A (en) *	1991-02-09	1994-09-13	Basf Aktiengesellschaft	Color former preparations
US9056948B2 (en)	2010-03-12	2015-06-16	Follmann & Co. Gesellschaft Fuer Chemie-Werkstoffe Und Verfahrenstechnik Mbh & Co. Kg	Microcapsules and production thereof
CN113453794A (zh) *	2018-12-18	2021-09-28	国际香料和香精公司	羟乙基纤维素微胶囊

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3044113A1 (de)	1980-11-24	1982-07-15	Basf Ag, 6700 Ludwigshafen	Mikrokapseln enthaltende wachsmassen
PT78129B (en) *	1983-08-18	1986-05-19	Moore Business Forms Inc	Microcapsules with reduced permeability
JPS60149489A (ja) *	1984-01-17	1985-08-06	Kureha Chem Ind Co Ltd	部分感圧紙
US4601863A (en) *	1984-02-09	1986-07-22	Kanzaki Paper Manufacturing Co., Ltd.	Process for producing powder of microcapsules
DE19852928C1 (de) *	1998-11-17	2000-08-03	Steffen Panzner	Strukturen in Form von Hohlkugeln
DE102009012455A1 (de) *	2009-03-12	2010-09-23	Follmann & Co. Gesellschaft Für Chemie-Werkstoffe Und -Verfahrenstechnik Mbh & Co. Kg	Verbesserte Mikrokapseln und ihre Herstellung

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS5030030A (fr) *	1973-07-19	1975-03-26
CA1040018A (fr) *	1974-06-19	1978-10-10	Dale R. Shackle	Microcapsules d'hydroxypropylcellulose reticulee

1978
- 1978-05-01 CA CA302,327A patent/CA1104881A/fr not_active Expired
- 1978-05-23 JP JP6157078A patent/JPS5417377A/ja active Pending
- 1978-05-31 GB GB2487678A patent/GB1603448A/en not_active Expired
- 1978-06-20 DE DE19782826939 patent/DE2826939A1/de not_active Withdrawn

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5346931A (en) *	1991-02-09	1994-09-13	Basf Aktiengesellschaft	Color former preparations
US9056948B2 (en)	2010-03-12	2015-06-16	Follmann & Co. Gesellschaft Fuer Chemie-Werkstoffe Und Verfahrenstechnik Mbh & Co. Kg	Microcapsules and production thereof
CN113453794A (zh) *	2018-12-18	2021-09-28	国际香料和香精公司	羟乙基纤维素微胶囊
CN113453794B (zh) *	2018-12-18	2023-06-27	国际香料和香精公司	羟乙基纤维素微胶囊

Also Published As

Publication number	Publication date
JPS5417377A (en)	1979-02-08
DE2826939A1 (de)	1979-01-18
GB1603448A (en)	1981-11-25

Legal Events

Date	Code	Title	Description
1998-07-14	MKEX	Expiry

Publication	Publication Date	Title
US4025455A (en)	1977-05-24	Cross-linked hydroxypropylcellulose microcapsules and process for making
US4356108A (en)	1982-10-26	Encapsulation process
CA1103825A (fr)	1981-06-23	Methode de production de revetements micro- capsulaires a teneur de colorants, et composes ainsi obtenus
US3875074A (en)	1975-04-01	Formation of microcapsules by interfacial cross-linking of emulsifier, and microcapsules produced thereby
US4601863A (en)	1986-07-22	Process for producing powder of microcapsules
US4681806A (en)	1987-07-21	Particles containing releasable fill material and method of making same
CA1149239A (fr)	1983-07-05	Obtention de microcapsules par condensation d'un precondensat de melamine-formaldehyde en presence de polymeres renfermant des groupements sulfoniques
EP0327748B1 (fr)	1991-10-16	Microcapsules en polyurée ou en polyurée-époxy
EP0633059A1 (fr)	1995-01-11	Procédé de fabrication de microcapsules de polyurées et produit obtenu
US4201404A (en)	1980-05-06	Pressure-sensitive marking materials
US4066568A (en)	1978-01-03	Method of producing microcapsules
US4317743A (en)	1982-03-02	Process for making microcapsules and resulting product
CA1104881A (fr)	1981-07-14	Methode de production de microcapsules a paroi d'encapsulage secondaires, et microcapsules ainsi obtenues
KR900005823B1 (ko)	1990-08-13	서방성(徐放性) 마이크로캡슐
EP0046415B1 (fr)	1984-12-27	Microcapsules pour copiage sensible à la pression
US4898780A (en)	1990-02-06	Production of microcapsules
US4209188A (en)	1980-06-24	Microcapsules, method of making same, and carbonless copying system including said microcapsules
US5196149A (en)	1993-03-23	Preparation of high solids, low viscosity carbonless paper gelatin base microcapsules
US4586060A (en)	1986-04-29	Microencapsulation process multi-walled microcapsules, transfer sheet record material and its production
CH615363A5 (en)	1980-01-31	Double-walled microcapsules with liquid filling material and process for preparing them
JPH0379061B2 (fr)	1991-12-17
CA1109258A (fr)	1981-09-22	Methode de production de compositions de revetement microcapsulaires nouveau genre radiocurables
CA1153887A (fr)	1983-09-20	Production de microcapsules
US5064470A (en)	1991-11-12	High solids, low viscosity carbonless paper gelatin base microcapsule system
JPS607935A (ja)	1985-01-16	マイクロカプセルの製造方法