DE2222697A1 - Pfropfpolymerisierte Mikrokapseln,ihre Herstellung und Verwendung - Google Patents
Pfropfpolymerisierte Mikrokapseln,ihre Herstellung und VerwendungInfo
- Publication number
- DE2222697A1 DE2222697A1 DE19722222697 DE2222697A DE2222697A1 DE 2222697 A1 DE2222697 A1 DE 2222697A1 DE 19722222697 DE19722222697 DE 19722222697 DE 2222697 A DE2222697 A DE 2222697A DE 2222697 A1 DE2222697 A1 DE 2222697A1
- Authority
- DE
- Germany
- Prior art keywords
- microcapsules
- polymer
- core
- coating
- solid
- 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.)
- Pending
Links
- 239000003094 microcapsule Substances 0.000 title claims description 135
- 238000004519 manufacturing process Methods 0.000 title claims description 10
- 229920000642 polymer Polymers 0.000 claims description 109
- 239000002775 capsule Substances 0.000 claims description 77
- 238000000576 coating method Methods 0.000 claims description 59
- 239000011248 coating agent Substances 0.000 claims description 52
- 239000002245 particle Substances 0.000 claims description 47
- 239000007787 solid Substances 0.000 claims description 46
- 238000006116 polymerization reaction Methods 0.000 claims description 41
- 239000012876 carrier material Substances 0.000 claims description 26
- 229920002472 Starch Polymers 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 24
- 235000019698 starch Nutrition 0.000 claims description 24
- 238000011049 filling Methods 0.000 claims description 22
- 239000008107 starch Substances 0.000 claims description 21
- 239000007788 liquid Substances 0.000 claims description 17
- 229920002678 cellulose Polymers 0.000 claims description 15
- 239000001913 cellulose Substances 0.000 claims description 15
- 229920000609 methyl cellulose Polymers 0.000 claims description 14
- 239000001923 methylcellulose Substances 0.000 claims description 14
- 235000010981 methylcellulose Nutrition 0.000 claims description 14
- 229920002451 polyvinyl alcohol Polymers 0.000 claims description 14
- 239000000758 substrate Substances 0.000 claims description 13
- 230000008569 process Effects 0.000 claims description 12
- 239000000126 substance Substances 0.000 claims description 12
- 239000004372 Polyvinyl alcohol Substances 0.000 claims description 10
- 235000019422 polyvinyl alcohol Nutrition 0.000 claims description 9
- 229920003043 Cellulose fiber Polymers 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 230000009172 bursting Effects 0.000 claims description 6
- 238000003466 welding Methods 0.000 claims description 6
- 229920001169 thermoplastic Polymers 0.000 claims description 5
- 238000002844 melting Methods 0.000 claims description 4
- 230000008018 melting Effects 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 3
- 238000005253 cladding Methods 0.000 claims 1
- 238000010348 incorporation Methods 0.000 claims 1
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 52
- 239000011162 core material Substances 0.000 description 46
- 239000000178 monomer Substances 0.000 description 46
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- 239000003431 cross linking reagent Substances 0.000 description 25
- 239000003995 emulsifying agent Substances 0.000 description 25
- 239000000725 suspension Substances 0.000 description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 25
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 23
- 239000004793 Polystyrene Substances 0.000 description 22
- 229920002223 polystyrene Polymers 0.000 description 22
- 239000000463 material Substances 0.000 description 19
- 239000000243 solution Substances 0.000 description 19
- 239000003054 catalyst Substances 0.000 description 18
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- 229920001807 Urea-formaldehyde Polymers 0.000 description 14
- 239000003795 chemical substances by application Substances 0.000 description 14
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- 239000000047 product Substances 0.000 description 11
- 239000004342 Benzoyl peroxide Substances 0.000 description 10
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 10
- 235000019400 benzoyl peroxide Nutrition 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- 238000005538 encapsulation Methods 0.000 description 10
- 239000000853 adhesive Substances 0.000 description 9
- 230000001070 adhesive effect Effects 0.000 description 9
- -1 methyl vinyl ketone Chemical compound 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- 239000012071 phase Substances 0.000 description 9
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 8
- 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 description 8
- 230000015572 biosynthetic process Effects 0.000 description 8
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 7
- 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 7
- 239000002609 medium Substances 0.000 description 7
- 239000003921 oil Substances 0.000 description 7
- 235000019198 oils Nutrition 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 235000013877 carbamide Nutrition 0.000 description 6
- 239000000835 fiber Substances 0.000 description 6
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 6
- 238000002156 mixing Methods 0.000 description 6
- 238000012546 transfer Methods 0.000 description 6
- 229920000578 graft copolymer Polymers 0.000 description 5
- 239000004816 latex Substances 0.000 description 5
- 229920000126 latex Polymers 0.000 description 5
- 239000004800 polyvinyl chloride Substances 0.000 description 5
- 229920000915 polyvinyl chloride Polymers 0.000 description 5
- 229920001187 thermosetting polymer Polymers 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
- 239000008346 aqueous phase Substances 0.000 description 4
- 239000007900 aqueous suspension Substances 0.000 description 4
- 239000004202 carbamide Substances 0.000 description 4
- 230000003197 catalytic effect Effects 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000004945 emulsification Methods 0.000 description 4
- 125000001165 hydrophobic group Chemical group 0.000 description 4
- 239000003605 opacifier Substances 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 3
- IMROMDMJAWUWLK-UHFFFAOYSA-N Ethenol Chemical compound OC=C IMROMDMJAWUWLK-UHFFFAOYSA-N 0.000 description 3
- 108010010803 Gelatin Proteins 0.000 description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 3
- 230000009471 action Effects 0.000 description 3
- 239000012736 aqueous medium Substances 0.000 description 3
- 239000011230 binding agent Substances 0.000 description 3
- 239000004490 capsule suspension Substances 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 238000004132 cross linking Methods 0.000 description 3
- 239000002612 dispersion medium Substances 0.000 description 3
- 239000008273 gelatin Substances 0.000 description 3
- 229920000159 gelatin Polymers 0.000 description 3
- 235000019322 gelatine Nutrition 0.000 description 3
- 235000011852 gelatine desserts Nutrition 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- 230000002209 hydrophobic effect Effects 0.000 description 3
- 239000003999 initiator Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 229920003023 plastic Polymers 0.000 description 3
- 239000004033 plastic Substances 0.000 description 3
- 239000006223 plastic coating Substances 0.000 description 3
- 239000002685 polymerization catalyst Substances 0.000 description 3
- ODGAOXROABLFNM-UHFFFAOYSA-N polynoxylin Chemical compound O=C.NC(N)=O ODGAOXROABLFNM-UHFFFAOYSA-N 0.000 description 3
- 229910052700 potassium Inorganic materials 0.000 description 3
- 239000011591 potassium Substances 0.000 description 3
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000006188 syrup Substances 0.000 description 3
- 235000020357 syrup Nutrition 0.000 description 3
- 229920005992 thermoplastic resin Polymers 0.000 description 3
- 239000004416 thermosoftening plastic Substances 0.000 description 3
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
- TUAMRELNJMMDMT-UHFFFAOYSA-N 3,5-xylenol Chemical compound CC1=CC(C)=CC(O)=C1 TUAMRELNJMMDMT-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 2
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 2
- 230000001464 adherent effect Effects 0.000 description 2
- 238000005054 agglomeration Methods 0.000 description 2
- 230000002776 aggregation Effects 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 239000011952 anionic catalyst Substances 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- FUSUHKVFWTUUBE-UHFFFAOYSA-N buten-2-one Chemical compound CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 description 2
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- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 2
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- SLGWESQGEUXWJQ-UHFFFAOYSA-N formaldehyde;phenol Chemical compound O=C.OC1=CC=CC=C1 SLGWESQGEUXWJQ-UHFFFAOYSA-N 0.000 description 2
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- YAMHXTCMCPHKLN-UHFFFAOYSA-N imidazolidin-2-one Chemical compound O=C1NCCN1 YAMHXTCMCPHKLN-UHFFFAOYSA-N 0.000 description 2
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- 230000002427 irreversible effect Effects 0.000 description 2
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- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 2
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- 229920003169 water-soluble polymer Polymers 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
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- QPVRKFOKCKORDP-UHFFFAOYSA-N 1,3-dimethylcyclohexa-2,4-dien-1-ol Chemical compound CC1=CC(C)(O)CC=C1 QPVRKFOKCKORDP-UHFFFAOYSA-N 0.000 description 1
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- STMDPCBYJCIZOD-UHFFFAOYSA-N 2-(2,4-dinitroanilino)-4-methylpentanoic acid Chemical compound CC(C)CC(C(O)=O)NC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O STMDPCBYJCIZOD-UHFFFAOYSA-N 0.000 description 1
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 1
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- 150000001299 aldehydes Chemical class 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 150000001348 alkyl chlorides Chemical class 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
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- ZAVUGVPMYAZPGN-UHFFFAOYSA-N benzoyl benzenecarboperoxoate;n,n-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1.C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 ZAVUGVPMYAZPGN-UHFFFAOYSA-N 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
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- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 1
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Inorganic materials [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 1
- ZOMBKNNSYQHRCA-UHFFFAOYSA-J calcium sulfate hemihydrate Chemical compound O.[Ca+2].[Ca+2].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O ZOMBKNNSYQHRCA-UHFFFAOYSA-J 0.000 description 1
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- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 235000019864 coconut oil Nutrition 0.000 description 1
- 239000003240 coconut oil Substances 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- WNAHIZMDSQCWRP-UHFFFAOYSA-N dodecane-1-thiol Chemical compound CCCCCCCCCCCCS WNAHIZMDSQCWRP-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000002320 enamel (paints) Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000004676 glycans Chemical class 0.000 description 1
- 229940015043 glyoxal Drugs 0.000 description 1
- 239000011507 gypsum plaster Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000000976 ink Substances 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 150000007974 melamines Chemical class 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 239000007764 o/w emulsion Substances 0.000 description 1
- 239000001254 oxidized starch Substances 0.000 description 1
- 235000013808 oxidized starch Nutrition 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- UCUUFSAXZMGPGH-UHFFFAOYSA-N penta-1,4-dien-3-one Chemical class C=CC(=O)C=C UCUUFSAXZMGPGH-UHFFFAOYSA-N 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920006254 polymer film Polymers 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229940096992 potassium oleate Drugs 0.000 description 1
- MLICVSDCCDDWMD-KVVVOXFISA-M potassium;(z)-octadec-9-enoate Chemical compound [K+].CCCCCCCC\C=C/CCCCCCCC([O-])=O MLICVSDCCDDWMD-KVVVOXFISA-M 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 239000010865 sewage Substances 0.000 description 1
- WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical compound [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 description 1
- 229910000342 sodium bisulfate Inorganic materials 0.000 description 1
- 235000002639 sodium chloride Nutrition 0.000 description 1
- 229940001584 sodium metabisulfite Drugs 0.000 description 1
- 239000004296 sodium metabisulphite Substances 0.000 description 1
- 239000012798 spherical particle Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- WODGXFMUOLGZSY-UHFFFAOYSA-J tetrasodium phosphonatooxy phosphate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]P([O-])(=O)OOP([O-])([O-])=O WODGXFMUOLGZSY-UHFFFAOYSA-J 0.000 description 1
- 239000012815 thermoplastic material Substances 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- LMYRWZFENFIFIT-UHFFFAOYSA-N toluene-4-sulfonamide Chemical compound CC1=CC=C(S(N)(=O)=O)C=C1 LMYRWZFENFIFIT-UHFFFAOYSA-N 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 238000006276 transfer reaction Methods 0.000 description 1
- 238000002604 ultrasonography Methods 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000004018 waxing Methods 0.000 description 1
- 239000002023 wood 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
- B41M5/1243—Inert particulate additives, e.g. protective stilt materials
-
- 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
- Y10T428/24—Structurally defined web or sheet [e.g., overall dimension, etc.]
- Y10T428/24802—Discontinuous or differential coating, impregnation or bond [e.g., artwork, printing, retouched photograph, etc.]
- Y10T428/24826—Spot bonds connect components
-
- 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
- Y10T428/25—Web or sheet containing structurally defined element or component and including a second component containing structurally defined particles
- Y10T428/254—Polymeric or resinous material
-
- 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
- Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
- Y10T428/2982—Particulate matter [e.g., sphere, flake, etc.]
- Y10T428/2984—Microcapsule with fluid core [includes liposome]
-
- 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
- Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
- Y10T428/2982—Particulate matter [e.g., sphere, flake, etc.]
- Y10T428/2984—Microcapsule with fluid core [includes liposome]
- Y10T428/2985—Solid-walled microcapsule from synthetic polymer
- Y10T428/2987—Addition polymer from unsaturated monomers only
-
- 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
- Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
- Y10T428/2982—Particulate matter [e.g., sphere, flake, etc.]
- Y10T428/2989—Microcapsule with solid core [includes liposome]
-
- 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
- Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
- Y10T428/2982—Particulate matter [e.g., sphere, flake, etc.]
- Y10T428/2991—Coated
- Y10T428/2998—Coated including synthetic resin or polymer
-
- 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
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31855—Of addition polymer from unsaturated monomers
- Y10T428/3188—Next to cellulosic
- Y10T428/31895—Paper or wood
- Y10T428/31899—Addition polymer of hydrocarbon[s] only
-
- 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
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31942—Of aldehyde or ketone condensation product
- Y10T428/31949—Next to cellulosic
- Y10T428/31964—Paper
- Y10T428/31967—Phenoplast
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Dispersion Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Manufacturing Of Micro-Capsules (AREA)
- Color Printing (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05142772 US3824114A (en) | 1971-05-12 | 1971-05-12 | Method of applying graft copolymer to cellulosic substrate and resultant article |
| US05235008 US3844816A (en) | 1971-05-12 | 1972-03-15 | Grafted, polymeric microcapsular system |
| CA141,809A CA982888A (en) | 1971-05-12 | 1972-05-10 | Grafted, polymeric microcapsular system |
| CA225,155A CA979749A (en) | 1971-05-12 | 1975-04-22 | Grafted, polymeric microcapsular system |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2222697A1 true DE2222697A1 (de) | 1972-11-23 |
Family
ID=27425582
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19722222697 Pending DE2222697A1 (de) | 1971-05-12 | 1972-05-09 | Pfropfpolymerisierte Mikrokapseln,ihre Herstellung und Verwendung |
Country Status (7)
| Country | Link |
|---|---|
| US (3) | US3824114A (https=) |
| BE (1) | BE783309A (https=) |
| CA (2) | CA982888A (https=) |
| DE (1) | DE2222697A1 (https=) |
| FR (1) | FR2137758A1 (https=) |
| GB (1) | GB1392858A (https=) |
| NL (1) | NL7206428A (https=) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2638324A1 (de) * | 1975-08-27 | 1977-03-10 | Nippon Oil Co Ltd | Kompressoroel-zusammensetzung mit ausgezeichneter oxydationsstabilitaet |
| DE2941714A1 (de) * | 1977-09-22 | 1981-04-23 | Hercules Inc., 19899 Wilmington, Del. | Papiererzeugnis aus cellulosefasern und einem organischem pigment |
| EP0218887A3 (en) * | 1985-09-14 | 1987-05-06 | Basf Aktiengesellschaft | Continuous process for producing aqueous dispersions of microcapsules with melamine-formaldehyde condensation product walls |
Families Citing this family (49)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3930101A (en) * | 1972-09-21 | 1975-12-30 | Champion Int Corp | Inorganic pigment-loaded polymeric microcapsular system |
| US4000087A (en) * | 1974-07-29 | 1976-12-28 | Moore Business Forms, Inc. | Microcapsules useful in carbonless copying systems and process for their preparation |
| US4064294A (en) * | 1975-06-02 | 1977-12-20 | Ppg Industries, Inc. | In-situ production of microcapsules on a substrate |
| US4154462A (en) * | 1975-10-30 | 1979-05-15 | Champion International Corporation | Transfer sheet coated with microcapsules and oil-absorptive particles |
| US4403063A (en) * | 1977-06-03 | 1983-09-06 | Hercules Incorporated | Organic pigments |
| US4281082A (en) * | 1977-06-03 | 1981-07-28 | Hercules Incorporated | Organic pigments |
| US4282060A (en) * | 1977-06-03 | 1981-08-04 | Hercules Incorporated | Organic pigments |
| US4414353A (en) * | 1977-06-03 | 1983-11-08 | Hercules Incorporated | Organic pigments |
| US4343729A (en) * | 1977-06-03 | 1982-08-10 | Hercules Incorporated | Organic pigments |
| US4353818A (en) * | 1977-06-03 | 1982-10-12 | Hercules Incorporated | Organic pigments |
| US4293666A (en) * | 1977-06-03 | 1981-10-06 | Hercules Incorporated | Organic pigments |
| US4403062A (en) * | 1977-06-03 | 1983-09-06 | Hercules Incorporated | Organic pigments |
| US4404310A (en) * | 1977-06-03 | 1983-09-13 | Hercules Incorporated | Organic pigments |
| US4348257A (en) * | 1977-06-03 | 1982-09-07 | Hercules Incorporated | Organic pigments |
| SE433234B (sv) * | 1977-09-22 | 1984-05-14 | Hercules Inc | Pappersprodukt innehallande organiska partiklar |
| FR2415535A1 (fr) * | 1978-01-30 | 1979-08-24 | Ato Chimie | Feuilles thermoplastiques multicouches |
| JPS54107881A (en) * | 1978-02-14 | 1979-08-24 | Fuji Photo Film Co Ltd | Preparation of minute capsule |
| US4211437A (en) * | 1978-04-25 | 1980-07-08 | Appleton Papers Inc. | Stilt capsules for pressure-sensitive record material |
| US4456724A (en) * | 1978-05-25 | 1984-06-26 | Hercules Incorporated | Organic pigments |
| JPS553969A (en) * | 1978-06-26 | 1980-01-12 | Mitsubishi Paper Mills Ltd | Single layer self-color developing pressure-sensitive recording paper |
| US4264678A (en) * | 1979-05-29 | 1981-04-28 | Gaf Corporation | Core-shell polymers |
| US4248939A (en) * | 1979-10-12 | 1981-02-03 | Hercules Incorporated | Process for double coating paper and product thereof |
| US4434267A (en) | 1980-06-16 | 1984-02-28 | Hercules Incorporated | Organic pigments |
| US4469555A (en) * | 1980-06-23 | 1984-09-04 | Hercules Incorporated | Organic pigments |
| US4586060A (en) * | 1980-07-29 | 1986-04-29 | Vassiliades Anthony E | Microencapsulation process multi-walled microcapsules, transfer sheet record material and its production |
| IL63220A (en) * | 1981-07-01 | 1985-09-29 | Yeda Res & Dev | Process for production of polyacrolein microspheres |
| US4391928A (en) * | 1981-09-04 | 1983-07-05 | Nl Industries, Inc. | Opacifying polymeric particle and uses |
| US4483959A (en) * | 1981-10-13 | 1984-11-20 | Hercules Incorporated | Organic pigments |
| US4565764A (en) * | 1982-09-10 | 1986-01-21 | Canon Kabushiki Kaisha | Microcapsule toner and process of making same |
| US5112541A (en) * | 1988-01-29 | 1992-05-12 | Idemitsu Kosan Company, Ltd. | Microencapsulated lubricating fluids and additives and method of making same |
| US5248558A (en) * | 1990-03-22 | 1993-09-28 | Eastman Kodak Company | Case-hardened gelatin-grafted polymer particles |
| US5281355A (en) * | 1992-04-29 | 1994-01-25 | Lever Brothers Company, Division Of Conopco, Inc. | Heavy duty liquid detergent compositions containing a capsule which comprises a component subject to degradation and a composite polymer |
| US5281357A (en) * | 1993-03-25 | 1994-01-25 | Lever Brothers Company, Division Of Conopco, Inc. | Protease containing heavy duty liquid detergent compositions comprising capsules comprising non-proteolytic enzyme and composite polymer |
| US5385959A (en) * | 1992-04-29 | 1995-01-31 | Lever Brothers Company, Division Of Conopco, Inc. | Capsule which comprises a component subject to degradation and a composite polymer |
| US5529719A (en) * | 1995-03-27 | 1996-06-25 | Xerox Corporation | Process for preparation of conductive polymeric composite particles |
| US6818685B1 (en) * | 1998-07-09 | 2004-11-16 | W. R. Grace & Co. -Conn. | Ink-receptive coatings and recording medium prepared therefrom |
| US6374707B1 (en) * | 1999-10-29 | 2002-04-23 | Steven F. Browning | Eye bolt wrench |
| US6866906B2 (en) | 2000-01-26 | 2005-03-15 | International Paper Company | Cut resistant paper and paper articles and method for making same |
| RO122629B1 (ro) | 2000-09-06 | 2009-10-30 | Appleton Papers Inc. | Adeziv microîncapsulat in situ şi procedeu de obţinere a acestuia |
| RU2387752C2 (ru) * | 2002-09-13 | 2010-04-27 | Интернэшнл Пейпер Компани | Бумага с улучшенной жесткостью и пухлостью и способ для ее изготовления |
| GB0229806D0 (en) * | 2002-12-20 | 2003-01-29 | Unilever Plc | Fabric care composition |
| GB2417495B8 (en) * | 2003-08-26 | 2011-09-07 | Univ Do Minho | Double walled microcapsules with an outer thermoplastic wall and application process thereof |
| GB0412854D0 (en) * | 2004-06-09 | 2004-07-14 | Unilever Plc | Fabric care composition |
| MX2007011113A (es) * | 2005-03-11 | 2007-11-15 | Int Paper Co | Composiciones que contienen micro-esferas expansibles y un compuesto ionico, asi como metodos para producir y utilizar las mismas. |
| GB0710369D0 (en) * | 2007-06-01 | 2007-07-11 | Unilever Plc | Improvements relating to perfume particles |
| US8382945B2 (en) * | 2008-08-28 | 2013-02-26 | International Paper Company | Expandable microspheres and methods of making and using the same |
| US8809477B2 (en) * | 2010-02-01 | 2014-08-19 | Johns Manville | Formaldehyde-free protein-containing binder compositions |
| US9988517B2 (en) * | 2012-06-05 | 2018-06-05 | Empire Technology Development Llc | Physical colorants for plastics based on the Christiansen effect |
| CN113088126B (zh) * | 2021-05-24 | 2022-03-22 | 中国科学院宁波材料技术与工程研究所 | 微胶囊、微胶囊化鳞片和/或纤维及其制备方法与应用 |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2655453A (en) * | 1952-04-23 | 1953-10-13 | Ncr Co | Manifold sheet having a crushresistant transfer film |
| US3281263A (en) * | 1961-03-17 | 1966-10-25 | Dow Chemical Co | Method for modifying polymeric substances with high energy radiation |
| US3429827A (en) * | 1962-11-23 | 1969-02-25 | Moore Business Forms Inc | Method of encapsulation |
| US3577515A (en) * | 1963-12-13 | 1971-05-04 | Pennwalt Corp | Encapsulation by interfacial polycondensation |
| US3405071A (en) * | 1963-12-30 | 1968-10-08 | Ibm | Process of making microcapsules |
| US3386851A (en) * | 1965-09-16 | 1968-06-04 | Jerry W. Harlan | Preparation of polymer-coated solid materials suitable as fillers for organic polymers |
| US3516941A (en) * | 1966-07-25 | 1970-06-23 | Minnesota Mining & Mfg | Microcapsules and process of making |
| US3481759A (en) * | 1966-08-22 | 1969-12-02 | Minnesota Mining & Mfg | Impact marking carbonless paper |
| US3657144A (en) * | 1967-06-05 | 1972-04-18 | Ncr Co | Encapsulation process |
| FR1589881A (https=) * | 1967-10-27 | 1970-04-06 | ||
| SE336469B (https=) * | 1968-07-05 | 1971-07-05 | Electrolux Ab | |
| US3617334A (en) * | 1968-11-08 | 1971-11-02 | Ncr Co | Pressure-sensitive sheet material |
-
1971
- 1971-05-12 US US05142772 patent/US3824114A/en not_active Expired - Lifetime
-
1972
- 1972-03-15 US US05235008 patent/US3844816A/en not_active Expired - Lifetime
- 1972-05-04 GB GB2090372A patent/GB1392858A/en not_active Expired
- 1972-05-09 DE DE19722222697 patent/DE2222697A1/de active Pending
- 1972-05-10 CA CA141,809A patent/CA982888A/en not_active Expired
- 1972-05-10 FR FR7216787A patent/FR2137758A1/fr not_active Withdrawn
- 1972-05-10 BE BE783309A patent/BE783309A/xx unknown
- 1972-05-12 NL NL7206428A patent/NL7206428A/xx unknown
-
1974
- 1974-05-21 US US05/471,885 patent/US4115474A/en not_active Expired - Lifetime
-
1975
- 1975-04-22 CA CA225,155A patent/CA979749A/en not_active Expired
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2638324A1 (de) * | 1975-08-27 | 1977-03-10 | Nippon Oil Co Ltd | Kompressoroel-zusammensetzung mit ausgezeichneter oxydationsstabilitaet |
| DE2941714A1 (de) * | 1977-09-22 | 1981-04-23 | Hercules Inc., 19899 Wilmington, Del. | Papiererzeugnis aus cellulosefasern und einem organischem pigment |
| EP0218887A3 (en) * | 1985-09-14 | 1987-05-06 | Basf Aktiengesellschaft | Continuous process for producing aqueous dispersions of microcapsules with melamine-formaldehyde condensation product walls |
Also Published As
| Publication number | Publication date |
|---|---|
| US4115474A (en) | 1978-09-19 |
| NL7206428A (https=) | 1972-11-14 |
| GB1392858A (en) | 1975-04-30 |
| FR2137758A1 (https=) | 1972-12-29 |
| CA982888A (en) | 1976-02-03 |
| CA979749A (en) | 1975-12-16 |
| US3844816A (en) | 1974-10-29 |
| US3824114A (en) | 1974-07-16 |
| BE783309A (fr) | 1972-11-10 |
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|---|---|---|---|
| OHJ | Non-payment of the annual fee |