CA1210886A - Adhesive cyanoacrylate compositions with reduced adhesion to skin - Google Patents
Adhesive cyanoacrylate compositions with reduced adhesion to skinInfo
- Publication number
- CA1210886A CA1210886A CA000444642A CA444642A CA1210886A CA 1210886 A CA1210886 A CA 1210886A CA 000444642 A CA000444642 A CA 000444642A CA 444642 A CA444642 A CA 444642A CA 1210886 A CA1210886 A CA 1210886A
- Authority
- CA
- Canada
- Prior art keywords
- weight
- percent
- composition
- cyanoacrylate
- vinyl acetate
- 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
- 239000000203 mixture Substances 0.000 title claims abstract description 282
- 230000001070 adhesive effect Effects 0.000 title claims abstract description 88
- 239000000853 adhesive Substances 0.000 title claims abstract description 87
- 229920001651 Cyanoacrylate Polymers 0.000 title claims abstract description 54
- MWCLLHOVUTZFKS-UHFFFAOYSA-N Methyl cyanoacrylate Chemical compound COC(=O)C(=C)C#N MWCLLHOVUTZFKS-UHFFFAOYSA-N 0.000 title claims abstract description 54
- 229920001577 copolymer Polymers 0.000 claims abstract description 74
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 claims abstract description 59
- 239000004014 plasticizer Substances 0.000 claims abstract description 50
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 claims abstract description 32
- FGBJXOREULPLGL-UHFFFAOYSA-N ethyl cyanoacrylate Chemical compound CCOC(=O)C(=C)C#N FGBJXOREULPLGL-UHFFFAOYSA-N 0.000 claims abstract description 30
- -1 2-cyanoacrylic acid ester Chemical class 0.000 claims abstract description 19
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims abstract description 18
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims abstract description 18
- 239000011976 maleic acid Substances 0.000 claims abstract description 18
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims abstract description 18
- 229920001897 terpolymer Polymers 0.000 claims abstract description 17
- 239000003112 inhibitor Substances 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 16
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims description 14
- 238000010539 anionic addition polymerization reaction Methods 0.000 claims description 11
- IRIAEXORFWYRCZ-UHFFFAOYSA-N Butylbenzyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCC1=CC=CC=C1 IRIAEXORFWYRCZ-UHFFFAOYSA-N 0.000 claims description 8
- 238000010526 radical polymerization reaction Methods 0.000 claims description 7
- NXQMCAOPTPLPRL-UHFFFAOYSA-N 2-(2-benzoyloxyethoxy)ethyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCCOCCOC(=O)C1=CC=CC=C1 NXQMCAOPTPLPRL-UHFFFAOYSA-N 0.000 claims description 6
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 claims description 6
- 230000008569 process Effects 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 5
- PZTAGFCBNDBBFZ-UHFFFAOYSA-N tert-butyl 2-(hydroxymethyl)piperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCCCC1CO PZTAGFCBNDBBFZ-UHFFFAOYSA-N 0.000 claims description 3
- 150000001558 benzoic acid derivatives Chemical class 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 239000004830 Super Glue Substances 0.000 abstract description 15
- 125000004494 ethyl ester group Chemical group 0.000 abstract 1
- 210000003491 skin Anatomy 0.000 description 67
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 62
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 25
- 238000012360 testing method Methods 0.000 description 21
- 238000002360 preparation method Methods 0.000 description 20
- 229920005989 resin Polymers 0.000 description 18
- 239000011347 resin Substances 0.000 description 18
- 239000004800 polyvinyl chloride Substances 0.000 description 16
- CGLQOIMEUPORRI-UHFFFAOYSA-N 2-(1-benzoyloxypropan-2-yloxy)propyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCC(C)OC(C)COC(=O)C1=CC=CC=C1 CGLQOIMEUPORRI-UHFFFAOYSA-N 0.000 description 15
- 239000003153 chemical reaction reagent Substances 0.000 description 15
- 229920002554 vinyl polymer Polymers 0.000 description 15
- 239000002904 solvent Substances 0.000 description 14
- 229920000915 polyvinyl chloride Polymers 0.000 description 12
- 239000000758 substrate Substances 0.000 description 12
- 239000011118 polyvinyl acetate Substances 0.000 description 11
- 229920002689 polyvinyl acetate Polymers 0.000 description 11
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- NLCKLZIHJQEMCU-UHFFFAOYSA-N cyano prop-2-enoate Chemical compound C=CC(=O)OC#N NLCKLZIHJQEMCU-UHFFFAOYSA-N 0.000 description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 9
- 230000005484 gravity Effects 0.000 description 9
- 239000007788 liquid Substances 0.000 description 9
- 239000007787 solid Substances 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- HIZCTWCPHWUPFU-UHFFFAOYSA-N Glycerol tribenzoate Chemical compound C=1C=CC=CC=1C(=O)OCC(OC(=O)C=1C=CC=CC=1)COC(=O)C1=CC=CC=C1 HIZCTWCPHWUPFU-UHFFFAOYSA-N 0.000 description 7
- 150000002148 esters Chemical class 0.000 description 7
- 238000009472 formulation Methods 0.000 description 7
- 238000002156 mixing Methods 0.000 description 7
- 229920000642 polymer Polymers 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 210000003811 finger Anatomy 0.000 description 6
- 150000002500 ions Chemical class 0.000 description 6
- 125000000129 anionic group Chemical group 0.000 description 5
- 230000006378 damage Effects 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 239000000499 gel Substances 0.000 description 5
- 230000009477 glass transition Effects 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 239000000178 monomer Substances 0.000 description 5
- IJVRPNIWWODHHA-UHFFFAOYSA-N 2-cyanoprop-2-enoic acid Chemical compound OC(=O)C(=C)C#N IJVRPNIWWODHHA-UHFFFAOYSA-N 0.000 description 4
- 229920001756 Polyvinyl chloride acetate Polymers 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 229920002432 poly(vinyl methyl ether) polymer Polymers 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000002791 soaking Methods 0.000 description 4
- 238000003860 storage Methods 0.000 description 4
- WCLDITPGPXSPGV-UHFFFAOYSA-N tricamba Chemical compound COC1=C(Cl)C=C(Cl)C(Cl)=C1C(O)=O WCLDITPGPXSPGV-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 229920001971 elastomer Polymers 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 229920001289 polyvinyl ether Polymers 0.000 description 3
- 238000009877 rendering Methods 0.000 description 3
- 239000005060 rubber Substances 0.000 description 3
- 229910001220 stainless steel Inorganic materials 0.000 description 3
- 239000010935 stainless steel Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 210000001519 tissue Anatomy 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 101100040225 Arabidopsis thaliana RS40 gene Proteins 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- GQPLMRYTRLFLPF-UHFFFAOYSA-N Nitrous Oxide Chemical compound [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 102100026827 Protein associated with UVRAG as autophagy enhancer Human genes 0.000 description 2
- 101710102978 Protein associated with UVRAG as autophagy enhancer Proteins 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 210000000988 bone and bone Anatomy 0.000 description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 210000002615 epidermis Anatomy 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 2
- 229920001519 homopolymer Polymers 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 2
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
- 238000005191 phase separation Methods 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- XINQFOMFQFGGCQ-UHFFFAOYSA-L (2-dodecoxy-2-oxoethyl)-[6-[(2-dodecoxy-2-oxoethyl)-dimethylazaniumyl]hexyl]-dimethylazanium;dichloride Chemical compound [Cl-].[Cl-].CCCCCCCCCCCCOC(=O)C[N+](C)(C)CCCCCC[N+](C)(C)CC(=O)OCCCCCCCCCCCC XINQFOMFQFGGCQ-UHFFFAOYSA-L 0.000 description 1
- UTPYTEWRMXITIN-YDWXAUTNSA-N 1-methyl-3-[(e)-[(3e)-3-(methylcarbamothioylhydrazinylidene)butan-2-ylidene]amino]thiourea Chemical compound CNC(=S)N\N=C(/C)\C(\C)=N\NC(=S)NC UTPYTEWRMXITIN-YDWXAUTNSA-N 0.000 description 1
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 1
- XFDQLDNQZFOAFK-UHFFFAOYSA-N 2-benzoyloxyethyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCCOC(=O)C1=CC=CC=C1 XFDQLDNQZFOAFK-UHFFFAOYSA-N 0.000 description 1
- UAWUVIQLUGFRLQ-UHFFFAOYSA-N 2-cyanopent-2-enoic acid Chemical class CCC=C(C#N)C(O)=O UAWUVIQLUGFRLQ-UHFFFAOYSA-N 0.000 description 1
- JIGUICYYOYEXFS-UHFFFAOYSA-N 3-tert-butylbenzene-1,2-diol Chemical compound CC(C)(C)C1=CC=CC(O)=C1O JIGUICYYOYEXFS-UHFFFAOYSA-N 0.000 description 1
- YWLXLRUDGLRYDR-ZHPRIASZSA-N 5beta,20-epoxy-1,7beta,10beta,13alpha-tetrahydroxy-9-oxotax-11-ene-2alpha,4alpha-diyl 4-acetate 2-benzoate Chemical compound O([C@H]1[C@H]2[C@@](C([C@H](O)C3=C(C)[C@@H](O)C[C@]1(O)C3(C)C)=O)(C)[C@@H](O)C[C@H]1OC[C@]12OC(=O)C)C(=O)C1=CC=CC=C1 YWLXLRUDGLRYDR-ZHPRIASZSA-N 0.000 description 1
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
- 101800000244 Allatostatin-3 Proteins 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 102100024133 Coiled-coil domain-containing protein 50 Human genes 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 1
- 101000910772 Homo sapiens Coiled-coil domain-containing protein 50 Proteins 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
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 206010052428 Wound Diseases 0.000 description 1
- 208000027418 Wounds and injury Diseases 0.000 description 1
- MINJAOUGXYRTEI-UHFFFAOYSA-N [3-benzoyloxy-2,2-bis(benzoyloxymethyl)propyl] benzoate Chemical compound C=1C=CC=CC=1C(=O)OCC(COC(=O)C=1C=CC=CC=1)(COC(=O)C=1C=CC=CC=1)COC(=O)C1=CC=CC=C1 MINJAOUGXYRTEI-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007824 aliphatic compounds Chemical class 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-M benzoate Chemical compound [O-]C(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-M 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- JLQUFIHWVLZVTJ-UHFFFAOYSA-N carbosulfan Chemical compound CCCCN(CCCC)SN(C)C(=O)OC1=CC=CC2=C1OC(C)(C)C2 JLQUFIHWVLZVTJ-UHFFFAOYSA-N 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 229940051157 d&c yellow no. 11 Drugs 0.000 description 1
- 239000011928 denatured alcohol Substances 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 210000005224 forefinger Anatomy 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- UPBDXRPQPOWRKR-UHFFFAOYSA-N furan-2,5-dione;methoxyethene Chemical compound COC=C.O=C1OC(=O)C=C1 UPBDXRPQPOWRKR-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- XJRBAMWJDBPFIM-UHFFFAOYSA-N methyl vinyl ether Chemical compound COC=C XJRBAMWJDBPFIM-UHFFFAOYSA-N 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- 239000010705 motor oil Substances 0.000 description 1
- APVPOHHVBBYQAV-UHFFFAOYSA-N n-(4-aminophenyl)sulfonyloctadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(=O)NS(=O)(=O)C1=CC=C(N)C=C1 APVPOHHVBBYQAV-UHFFFAOYSA-N 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 239000001272 nitrous oxide Substances 0.000 description 1
- 239000000123 paper Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 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
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 239000002952 polymeric resin Substances 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- IZMJMCDDWKSTTK-UHFFFAOYSA-N quinoline yellow Chemical compound C1=CC=CC2=NC(C3C(C4=CC=CC=C4C3=O)=O)=CC=C21 IZMJMCDDWKSTTK-UHFFFAOYSA-N 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- NZCRJKRKKOLAOJ-XRCRFVBUSA-N rifaximin Chemical compound OC1=C(C(O)=C2C)C3=C4N=C5C=C(C)C=CN5C4=C1NC(=O)\C(C)=C/C=C/[C@H](C)[C@H](O)[C@@H](C)[C@@H](O)[C@@H](C)[C@H](OC(C)=O)[C@H](C)[C@@H](OC)\C=C\O[C@@]1(C)OC2=C3C1=O NZCRJKRKKOLAOJ-XRCRFVBUSA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 230000037380 skin damage Effects 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 210000003813 thumb Anatomy 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J4/00—Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16
- C09J4/06—Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond in combination with a macromolecular compound other than an unsaturated polymer of groups C09J159/00 - C09J187/00
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F259/00—Macromolecular compounds obtained by polymerising monomers on to polymers of halogen containing monomers as defined in group C08F14/00
- C08F259/02—Macromolecular compounds obtained by polymerising monomers on to polymers of halogen containing monomers as defined in group C08F14/00 on to polymers containing chlorine
- C08F259/04—Macromolecular compounds obtained by polymerising monomers on to polymers of halogen containing monomers as defined in group C08F14/00 on to polymers containing chlorine on to polymers of vinyl chloride
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Materials For Medical Uses (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/446,254 US4444933A (en) | 1982-12-02 | 1982-12-02 | Adhesive cyanoacrylate compositions with reduced adhesion to skin |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1210886A true CA1210886A (en) | 1986-09-02 |
Family
ID=23771911
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000444642A Expired CA1210886A (en) | 1982-12-02 | 1984-01-04 | Adhesive cyanoacrylate compositions with reduced adhesion to skin |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US4444933A (enExample) |
| JP (1) | JPS60166361A (enExample) |
| AU (1) | AU568831B2 (enExample) |
| CA (1) | CA1210886A (enExample) |
| DE (1) | DE3400577C2 (enExample) |
| GB (1) | GB2152070B (enExample) |
Families Citing this family (114)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS59147067A (ja) * | 1983-02-09 | 1984-08-23 | Alpha Giken:Kk | α−シアノアクリレ−ト系耐熱性瞬間接着剤組成物 |
| WO1987004921A1 (en) * | 1986-02-13 | 1987-08-27 | Krazy Glue Inc. | Nail polish remover and conditioner composition |
| US4837260A (en) * | 1986-05-23 | 1989-06-06 | Toagosei Chemical Industry Co., Ltd. | Cyanoacrylate compositions |
| US4816307A (en) * | 1987-01-20 | 1989-03-28 | Honeycutt Travis W | Novel infectious waste containment |
| US4900500A (en) * | 1987-01-20 | 1990-02-13 | Isolyser Co., Inc. | Point-of-use infectious waste disposal system |
| US5306490A (en) * | 1992-04-20 | 1994-04-26 | Medlogic, Inc. | Methods for retarding blister formation by use of cyanoacrylate adhesives |
| JP2616345B2 (ja) * | 1992-05-29 | 1997-06-04 | 東亞合成株式会社 | 接着剤組成物 |
| US6323275B2 (en) | 1992-05-28 | 2001-11-27 | Toagosei Co., Ltd. | Cyanoacrylate adhesive composition |
| GB2268503B (en) * | 1992-05-28 | 1996-07-31 | Toa Gosei Chem Ind | Cyanoacrylate adhesive composition |
| JP2590673B2 (ja) * | 1992-05-29 | 1997-03-12 | 東亞合成株式会社 | 接着剤組成物 |
| US6342213B1 (en) | 1992-06-09 | 2002-01-29 | Medlogic Global Corporation | Methods for treating non-suturable wounds by use of cyanoacrylate adhesives |
| US5328944A (en) * | 1992-07-14 | 1994-07-12 | Loctite Corporation | Cyanoacrylate adhesives with improved cured thermal properties |
| US5254132A (en) * | 1992-09-01 | 1993-10-19 | Medlogic, Inc. | Methods for treating suturable wounds by use of sutures and cyanoacrylate adhesives |
| US5424343A (en) * | 1992-10-08 | 1995-06-13 | Loctite Corporation | Thermally resistant cyanoacrylates employing substituted napthasultone additive |
| US5288794A (en) * | 1992-10-23 | 1994-02-22 | Loctite Corporation | Cyanoacrylate adhesives with improved cured thermal properties utilizing substituted aromatic additive |
| US5403591A (en) * | 1993-06-25 | 1995-04-04 | Medlogic Global Corporation | Methods for inhibiting skin ulceration by use of cyanoacrylate adhesives |
| JPH0782531A (ja) * | 1993-09-17 | 1995-03-28 | Three Bond Co Ltd | 接着剤組成物 |
| US5762955A (en) | 1994-02-04 | 1998-06-09 | Smith; Stephen Jay | Method for application and maintenance of medication on body tissue |
| WO1995022998A1 (en) * | 1994-02-24 | 1995-08-31 | Medlogic Global Corporation | Methods for reducing skin irritation from artificial devices by use of cyanoacrylate adhesives |
| US6492434B1 (en) | 1994-06-23 | 2002-12-10 | Flowers Park Ltd. | Methods for inhibiting skin ulceration by use of cyanoacrylate adhesives |
| JPH0812946A (ja) | 1994-06-28 | 1996-01-16 | Taoka Chem Co Ltd | 改質されたα−シアノアクリレート系接着剤組成物 |
| US5580565A (en) * | 1994-09-01 | 1996-12-03 | Medlogic Global Corporation | Use of cyanoacrylate adhesives for providing a protective barrier film for the skin |
| US5480935A (en) * | 1994-09-01 | 1996-01-02 | Medlogic Global Corporation | Cyanoacrylate adhesive compositions |
| US6001213A (en) * | 1994-10-13 | 1999-12-14 | Loctite Corporation | Methods for forming non-environmentally hazardous, non-volatile adhesive promoter compositions for curing adhesives |
| US5567266A (en) * | 1994-10-13 | 1996-10-22 | Loctite Corporation | Non-environmentally hazardous, non-volatile adhesive promoter composition for curing adhesives |
| US20020018689A1 (en) * | 1995-06-07 | 2002-02-14 | Badejo Ibraheem T. | Adhesive applicators with improved polymerization initiators |
| US5981621A (en) * | 1996-02-29 | 1999-11-09 | Closure Medical Corporation | Monomeric compositions effective as wound closure devices |
| US6217603B1 (en) | 1997-08-29 | 2001-04-17 | Closure Medical Corporation | Methods of applying monomeric compositions effective as wound closure devices |
| DE19621850A1 (de) * | 1996-05-31 | 1997-12-04 | Henkel Kgaa | Cycanacrylat-Klebstoff |
| US5684042A (en) * | 1997-01-10 | 1997-11-04 | Medlogic Global Corporation | Cyanoacrylate compositions comprising an antimicrobial agent |
| US5990214A (en) * | 1997-07-31 | 1999-11-23 | Velsicol Chemical Corporation | Liquid glycol benzoate compositions |
| US6010444A (en) * | 1997-09-05 | 2000-01-04 | Isolyser Company, Inc. | Infectious waste containment system |
| US6090397A (en) * | 1997-11-03 | 2000-07-18 | Medlogic Global Corporation | Kits containing cyanoacrylate compositions comprising an antimicrobial agent |
| US6001345A (en) * | 1997-11-03 | 1999-12-14 | Medlogic Global Corporation | Application of cyanoacrylate/anti-microbial compositions to the peri-wound or peri-mucosal area |
| US6475502B1 (en) | 1997-11-03 | 2002-11-05 | Flowers Park Ltd. | Kits containing cyanoacrylate compositions comprising an antimicrobial agent |
| DE19752893A1 (de) * | 1997-11-28 | 1999-08-12 | Henkel Kgaa | Cyanacrylat-Klebstoff mit einem Ester-Zusatz |
| GB9820457D0 (en) | 1998-09-18 | 1998-11-11 | Medlogic Global Corp | Methods for sterilizing cyanoacrylate compositions |
| US6703003B1 (en) * | 1998-12-15 | 2004-03-09 | Three Bond Co., Ltd. | Manicure composition for nail |
| ATE531397T1 (de) | 1999-05-29 | 2011-11-15 | Tyco Healthcare | Bioabsorbierbare mischungen und daraus hergestellte chirurgische artikel |
| FR2811218B1 (fr) | 2000-07-05 | 2003-02-28 | Patrice Suslian | Dispositif implantable destine a corriger l'incontinence urinaire |
| GB0025068D0 (en) * | 2000-10-12 | 2000-11-29 | Browning Healthcare Ltd | Apparatus and method for treating female urinary incontinence |
| US20060205995A1 (en) * | 2000-10-12 | 2006-09-14 | Gyne Ideas Limited | Apparatus and method for treating female urinary incontinence |
| US8167785B2 (en) * | 2000-10-12 | 2012-05-01 | Coloplast A/S | Urethral support system |
| US6579916B1 (en) | 2000-11-21 | 2003-06-17 | Medlogic Global Corporation | Methods for sterilizing cyanoacrylate compositions |
| US6977278B1 (en) | 2001-01-08 | 2005-12-20 | Loctite (R&D) Ltd. | Cyanoacrylate compositions curable to flexible polymeric materials |
| GB0108088D0 (en) | 2001-03-30 | 2001-05-23 | Browning Healthcare Ltd | Surgical implant |
| US8403954B2 (en) | 2001-05-22 | 2013-03-26 | Sanostec Corp. | Nasal congestion, obstruction relief, and drug delivery |
| US6822052B2 (en) * | 2001-05-24 | 2004-11-23 | Henkel Corporation | Toughened cyanoacrylate adhesives containing alkene-acrylate copolymers and method for production |
| US6849082B2 (en) | 2001-10-19 | 2005-02-01 | Spartan Products Inc. | Method for curing cyanoacrylate adhesives |
| WO2003041686A2 (en) * | 2001-11-14 | 2003-05-22 | Medlogic Global Limited | Improved therapy for topical diseases |
| US7255874B1 (en) | 2001-12-21 | 2007-08-14 | Closure Medical Corporation | Biocompatible polymers and adhesives: compositions, methods of making and uses related thereto |
| ATE390141T1 (de) * | 2002-02-20 | 2008-04-15 | Spartan Products Inc | Verfahren zur härtung von cyanoacrylat- klebstoffen |
| US20030158579A1 (en) | 2002-02-20 | 2003-08-21 | Max Azevedo | Method for curing cyanoacrylate adhesives |
| AU2003229899A1 (en) * | 2002-04-11 | 2003-10-27 | Gyne Ideas Limited | Apparatus and method for treating female urinary incontinence |
| US8097007B2 (en) | 2002-08-02 | 2012-01-17 | C. R. Bard, Inc. | Self-anchoring sling and introducer system |
| ES2213467B1 (es) | 2002-09-29 | 2005-06-01 | Condensia Quimica, S.A. | Mezcla de plastificantes para la dispersibilidad acuosa de resinas. |
| US20040131827A1 (en) * | 2003-01-06 | 2004-07-08 | Loctite (R&D) Limited | Toughened cyanoacrylate compositions |
| US7390851B1 (en) | 2003-01-06 | 2008-06-24 | Loctite (R&D) Limited | Toughened cyanoacrylate compositions |
| GB0307082D0 (en) | 2003-03-27 | 2003-04-30 | Gyne Ideas Ltd | Drug delivery device and method |
| US7909808B2 (en) * | 2003-06-13 | 2011-03-22 | Medlogic Global Limited | Dual-ended applicator for dispensing two fluids |
| US20040253039A1 (en) * | 2003-06-13 | 2004-12-16 | Stenton Richard J. | Disposable applicator for topical composition |
| DE102004001493A1 (de) * | 2004-01-09 | 2005-08-04 | Henkel Kgaa | Spaltüberbrückender Cyanacrylat-Klebstoff |
| US20050197421A1 (en) * | 2004-03-03 | 2005-09-08 | Loomis Gary L. | Process for preparation of cyanoacrylate compositions |
| GB0411360D0 (en) | 2004-05-21 | 2004-06-23 | Mpathy Medical Devices Ltd | Implant |
| US20050287216A1 (en) * | 2004-06-29 | 2005-12-29 | Loomis Gary L | Medical imaging agents for injectable compositions |
| US8061917B2 (en) * | 2005-06-10 | 2011-11-22 | Medlogic Global Limited | Liquid applicator and method of use |
| US8071675B2 (en) * | 2005-12-19 | 2011-12-06 | Loctite (R&D) Limited | Cyanoacrylate composite forming system |
| US8092819B2 (en) * | 2006-01-27 | 2012-01-10 | Cook Medical Technologies LLC. | Implantable medical device coated with a bioactive agent |
| US8702751B2 (en) * | 2006-06-30 | 2014-04-22 | Advanced Medical Solutions (Plymouth) Limited | Surgical adhesive applicator |
| US7772306B2 (en) * | 2006-07-18 | 2010-08-10 | Glustitch, Inc. | Cyanoacrylate compositions having increased stability under irradiation |
| US20080152614A1 (en) * | 2006-12-22 | 2008-06-26 | 3M Innovative Properties Company | Method and kit for skin lesion prevention and/or protection |
| US8518076B2 (en) * | 2007-01-08 | 2013-08-27 | Advanced Medical Solutions (Plymouth) Limited | Surgical adhesive applicator |
| US8729121B2 (en) | 2007-06-25 | 2014-05-20 | Adhezion Biomedical, Llc | Curing accelerator and method of making |
| JP2011503108A (ja) * | 2007-11-12 | 2011-01-27 | ヴァロー メディカル、 インク． | 医療グレードシアノアクリレートの単一バイアル製剤 |
| WO2009064291A1 (en) | 2007-11-14 | 2009-05-22 | Spartan Medical Products, Llc | Cyanoacrylate tissue adhesives |
| US20090246262A1 (en) * | 2008-03-28 | 2009-10-01 | Valor Medical, Inc. | Easily applied field dressing for wounds |
| US8342765B2 (en) * | 2008-06-12 | 2013-01-01 | Advanced Medical Solutions (Plymouth) Limited | Liquid applicator |
| US8293838B2 (en) * | 2008-06-20 | 2012-10-23 | Adhezion Biomedical, Llc | Stable and sterile tissue adhesive composition with a controlled high viscosity |
| US8198344B2 (en) * | 2008-06-20 | 2012-06-12 | Adhezion Biomedical, Llc | Method of preparing adhesive compositions for medical use: single additive as both the thickening agent and the accelerator |
| US20110117047A1 (en) | 2008-06-23 | 2011-05-19 | Adhezion Biomedical, Llc | Cyanoacrylate tissue adhesives with desirable permeability and tensile strength |
| US8173722B2 (en) * | 2008-07-10 | 2012-05-08 | Aesculap Ag | Adhesive compositions for use in surgical therapy |
| US8609128B2 (en) * | 2008-10-31 | 2013-12-17 | Adhezion Biomedical, Llc | Cyanoacrylate-based liquid microbial sealant drape |
| US8652510B2 (en) | 2008-10-31 | 2014-02-18 | Adhezion Biomedical, Llc | Sterilized liquid compositions of cyanoacrylate monomer mixtures |
| US9254133B2 (en) | 2008-10-31 | 2016-02-09 | Adhezion Biomedical, Llc | Sterilized liquid compositions of cyanoacrylate monomer mixtures |
| DE102009012187A1 (de) * | 2009-02-26 | 2010-09-02 | Aesculap Aktiengesellschaft | Medizinische Klebstoffzusammensetzung |
| DK2269517T3 (da) | 2009-07-01 | 2014-01-06 | Advanced Medical Solutions Plymouth Ltd | Væskeapplikator |
| JP4605671B1 (ja) * | 2009-12-25 | 2011-01-05 | 田岡化学工業株式会社 | エチル−２−シアノアクリレート接着剤組成物 |
| US9309019B2 (en) | 2010-05-21 | 2016-04-12 | Adhezion Biomedical, Llc | Low dose gamma sterilization of liquid adhesives |
| PL2616520T3 (pl) | 2010-09-15 | 2018-08-31 | Henkel IP & Holding GmbH | Dwuczęściowe, cyjanoakrylanowe/kationowo utwardzalne układy klejowe |
| WO2013111036A1 (en) | 2012-01-23 | 2013-08-01 | Henkel Ireland Limited | Two-part, cyanoacrylate/free radically curable adhesive systems |
| US8981027B2 (en) | 2013-03-15 | 2015-03-17 | Henkel IP & Holding GmbH | Two-part, cyanoacrylate/cationically curable adhesive systems |
| CN105246872B (zh) | 2013-05-21 | 2019-08-13 | 汉高知识产权控股有限责任公司 | 氰基丙烯酸酯组合物 |
| JP2015024575A (ja) * | 2013-07-26 | 2015-02-05 | 大日本印刷株式会社 | 熱転写記録材料及び印画物 |
| US9421297B2 (en) | 2014-04-02 | 2016-08-23 | Adhezion Biomedical, Llc | Sterilized compositions of cyanoacrylate monomers and naphthoquinone 2,3-oxides |
| US9974471B1 (en) | 2014-10-24 | 2018-05-22 | Verily Life Sciences Llc | Analyte detection system and method for intradermal implantation of biocompatible optode nanosensors |
| GB2534548B (en) | 2014-12-29 | 2020-08-12 | Adv Med Solutions Ltd | Adhesive applicator |
| US9993499B2 (en) * | 2015-03-04 | 2018-06-12 | Stacey Bone | Product for and method of protecting and increasing friction of animal paws |
| US10098574B1 (en) | 2015-07-07 | 2018-10-16 | Verily Life Sciences Llc | Porous microneedles through sacrificial sugar incorporation, analyte detection system, and method for intradermal optode nanosensor implantation |
| EP3124509A1 (en) | 2015-07-31 | 2017-02-01 | Afinitica Technologies, S. L. | Fast light curing cyanoacrylate compositions |
| CN115006537A (zh) | 2016-01-26 | 2022-09-06 | 利维申制药有限公司 | α-肾上腺素能药剂的组合物和用途 |
| GB2549975B (en) | 2016-05-05 | 2022-04-13 | Adv Med Solutions Ltd | Liquid applicator |
| KR102713236B1 (ko) | 2017-02-09 | 2024-10-04 | 페머시스 인크. | 생분해성 시아노아크릴레이트를 포함하는 조성물 및 방법 |
| ES3037954T3 (en) | 2018-05-02 | 2025-10-08 | Femasys Inc | Devices for controlled delivery |
| GB2576792B (en) | 2018-08-13 | 2022-09-14 | Henkel Ag & Co Kgaa | A two-part cyanoacrylate curable adhesive system |
| GB2576791B (en) | 2018-08-13 | 2022-09-14 | Henkel Ag & Co Kgaa | A two-part cyanoacrylate curable adhesive system |
| GB2576704B (en) * | 2018-08-16 | 2022-01-12 | Henkel IP & Holding GmbH | Cyanoacrylate compositions |
| JP7582938B2 (ja) | 2018-10-18 | 2024-11-13 | ヘンケル・アクチェンゲゼルシャフト・ウント・コムパニー・コマンディットゲゼルシャフト・アウフ・アクチェン | ２パートシアノアクリレート／フリーラジカル硬化性接着剤系 |
| EP3924438A4 (en) | 2019-02-11 | 2022-11-16 | Henkel AG & Co. KGaA | TWO-PART CYANOACRYLATE/FREE-ADICAL BONDING SYSTEMS |
| GB2582537B (en) | 2019-03-04 | 2022-02-23 | Henkel IP & Holding GmbH | Two-part, cyanoacrylate/cationically curable adhesive systems |
| CN112442320B (zh) * | 2020-11-26 | 2022-06-21 | 山东禹王和天下新材料有限公司 | 一种机器用橡皮筋胶及其制备方法 |
| CN112552829B (zh) * | 2020-11-26 | 2022-08-09 | 山东禹王和天下新材料有限公司 | 一种无味睫毛嫁接胶及其制备方法与应用 |
| EP4089124A1 (en) * | 2021-05-12 | 2022-11-16 | Unecol Adhesive Ideas, S.L. | Method for bonding a thermoplastic piping system without the use of solvent-based adhesives, and associated adhesive without the use of solvents |
| EP4547727A1 (en) | 2022-06-28 | 2025-05-07 | Henkel AG & Co. KGaA | Method of underwater bonding |
| GB2633319B (en) | 2023-09-04 | 2026-03-25 | Henkel Ag & Co Kgaa | Method of underwater bonding |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2794788A (en) * | 1952-11-01 | 1957-06-04 | Eastman Kodak Co | Adhesive compositions containing alkyl esters of cyanoacrylic acid |
| US2804073A (en) * | 1953-01-26 | 1957-08-27 | Protective Teatments Inc | Fluid surgical dressing |
| US2784127A (en) * | 1954-06-02 | 1957-03-05 | Eastman Kodak Co | Plasticized monomeric adhesive compositions and articles prepared therefrom |
| US3223083A (en) * | 1960-09-09 | 1965-12-14 | President And Directors Of Geo | Method for adhesively securing together skin and other soft tissue and bone |
| US3667472A (en) * | 1961-10-19 | 1972-06-06 | Borden Inc | Adhesive for living tissue |
| GB1123360A (en) * | 1966-01-21 | 1968-08-14 | American Cyanamid Co | Thickening of alpha-cyanoacrylates |
| US3507822A (en) * | 1967-08-18 | 1970-04-21 | Torao Miyami | Tooth coating composition |
| US3564078A (en) * | 1968-05-17 | 1971-02-16 | Eastman Kodak Co | Alpha-cyanoacrylate adhesive compositions |
| US3654239A (en) * | 1970-11-20 | 1972-04-04 | Eastman Kodak Co | Process for the preparation of poly-(alpha-cyanoacrylates) |
| IE35430B1 (en) * | 1971-01-06 | 1976-02-18 | Intercontinental Chem Co Ltd | High-viscosity cyanoacrylate adhesive compositions and processes for their preparation |
| IE34874B1 (en) * | 1971-01-13 | 1975-09-03 | Intercontinental Chem Co Ltd | Cyanoacrylate adhesive compositions |
| US4196271A (en) * | 1975-12-24 | 1980-04-01 | Toagosei Chemical Industry Co., Ltd. | Adhesive composition |
| IE45626B1 (en) * | 1976-07-14 | 1982-10-20 | Loctite Ltd | Filled cyanoacrylate adhesive compositions |
| JPS5335744A (en) * | 1976-09-16 | 1978-04-03 | Toagosei Chem Ind Co Ltd | Composite adhesives |
-
1982
- 1982-12-02 US US06/446,254 patent/US4444933A/en not_active Expired - Lifetime
-
1983
- 1983-12-29 AU AU22940/83A patent/AU568831B2/en not_active Ceased
- 1983-12-29 GB GB08334535A patent/GB2152070B/en not_active Expired
-
1984
- 1984-01-04 CA CA000444642A patent/CA1210886A/en not_active Expired
- 1984-01-10 DE DE3400577A patent/DE3400577C2/de not_active Expired - Lifetime
- 1984-01-27 JP JP59013191A patent/JPS60166361A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| US4444933A (en) | 1984-04-24 |
| AU2294083A (en) | 1985-07-04 |
| DE3400577A1 (de) | 1985-07-18 |
| AU568831B2 (en) | 1988-01-14 |
| GB2152070B (en) | 1987-09-09 |
| JPH0518874B2 (enExample) | 1993-03-15 |
| JPS60166361A (ja) | 1985-08-29 |
| GB8334535D0 (en) | 1984-02-01 |
| DE3400577C2 (de) | 1994-09-15 |
| GB2152070A (en) | 1985-07-31 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4444933A (en) | Adhesive cyanoacrylate compositions with reduced adhesion to skin | |
| CA1272322A (en) | Methacrylate-based compositions | |
| Shantha et al. | Developments and applications of cyanoacrylate adhesives | |
| US3971766A (en) | Pressure-sensitive adhesive and pressure-sensitive adhesive tape or drape | |
| US5486426A (en) | Cold sealable cohesive polymer coated polyolefin substrate | |
| US3983297A (en) | Pressure-sensitive adhesive tape or drape | |
| US5459184A (en) | Moisture-actuated hot melt adhesive | |
| US4170612A (en) | Pressure sensitive adhesive compositions | |
| US3282773A (en) | Adhesive composition and method of bonding using alpha-cyanoacrylate esters and vinyl aromatics | |
| EP0068696B1 (en) | Cured pressure sensitive adhesives | |
| EP0297902A2 (en) | Cold sealable terpolymers, their preparation, articles comprising them and their use to effect sealing | |
| US4340532A (en) | Adhesive compositions containing alkoxy alkyl acrylates or methacrylates | |
| US4370380A (en) | Pressure-sensitive adhesive | |
| US4337325A (en) | Pressure-sensitive adhesive | |
| TWI287564B (en) | Wet-stick adhesives, articles, and methods | |
| TR27653A (tr) | Mükemmel hcfc dayanikliliklari olan termoplastik recine bilesimleri hazirlanmasi icin islem. | |
| JPS60219242A (ja) | 粘着付与剤および圧感接着剤中におけるそれらの使用法 | |
| Denchev et al. | Thermal behaviour and adhesive properties of some cyanoacrylate adhesives with increased heat resistance | |
| CA2027467A1 (en) | Dispersion of fine particles of a polymer | |
| US3325459A (en) | Sheet materials | |
| GB2073758A (en) | Pressure-sensitive adhesives | |
| EP0309901A3 (en) | Water-borne acrylic/polyester resin | |
| US3165489A (en) | Adhesives from copolymers of ethylene and n-vinyl-n-methyl-acetamide | |
| JPS5817238B2 (ja) | 水性接着剤組成物 | |
| JPS6016447B2 (ja) | 接着剤の製造方法 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |