CA1299459C - Detergent composition containing ethylenediamine-n,n'disuccinic acid - Google Patents
Detergent composition containing ethylenediamine-n,n'disuccinic acidInfo
- Publication number
- CA1299459C CA1299459C CA000551358A CA551358A CA1299459C CA 1299459 C CA1299459 C CA 1299459C CA 000551358 A CA000551358 A CA 000551358A CA 551358 A CA551358 A CA 551358A CA 1299459 C CA1299459 C CA 1299459C
- Authority
- CA
- Canada
- Prior art keywords
- alkali metal
- composition
- mixtures
- group
- alkyl
- 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 - Lifetime
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 154
- 239000003599 detergent Substances 0.000 title claims abstract description 73
- VKZRWSNIWNFCIQ-UHFFFAOYSA-N 2-[2-(1,2-dicarboxyethylamino)ethylamino]butanedioic acid Chemical compound OC(=O)CC(C(O)=O)NCCNC(C(O)=O)CC(O)=O VKZRWSNIWNFCIQ-UHFFFAOYSA-N 0.000 title claims abstract description 62
- 239000004094 surface-active agent Substances 0.000 claims abstract description 38
- 150000003839 salts Chemical class 0.000 claims abstract description 25
- 101001095815 Homo sapiens E3 ubiquitin-protein ligase RING2 Proteins 0.000 claims abstract 2
- 101001057193 Homo sapiens Membrane-associated guanylate kinase, WW and PDZ domain-containing protein 1 Proteins 0.000 claims abstract 2
- 101000740048 Homo sapiens Ubiquitin carboxyl-terminal hydrolase BAP1 Proteins 0.000 claims abstract 2
- 101000740049 Latilactobacillus curvatus Bioactive peptide 1 Proteins 0.000 claims abstract 2
- 102100027240 Membrane-associated guanylate kinase, WW and PDZ domain-containing protein 1 Human genes 0.000 claims abstract 2
- -1 alkaline earth Chemical compound 0.000 claims description 60
- 125000000217 alkyl group Chemical group 0.000 claims description 50
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 29
- 239000002253 acid Substances 0.000 claims description 29
- 229910052783 alkali metal Inorganic materials 0.000 claims description 23
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 22
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 22
- 239000004744 fabric Substances 0.000 claims description 21
- 150000001340 alkali metals Chemical class 0.000 claims description 20
- 150000003863 ammonium salts Chemical class 0.000 claims description 18
- 239000002736 nonionic surfactant Substances 0.000 claims description 16
- 150000007513 acids Chemical class 0.000 claims description 15
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 15
- 239000007788 liquid Substances 0.000 claims description 15
- 239000003945 anionic surfactant Substances 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 12
- 239000003093 cationic surfactant Substances 0.000 claims description 8
- 150000008051 alkyl sulfates Chemical class 0.000 claims description 7
- 239000002563 ionic surfactant Substances 0.000 claims description 6
- 150000003467 sulfuric acid derivatives Chemical class 0.000 claims description 6
- 229910000288 alkali metal carbonate Inorganic materials 0.000 claims description 5
- 150000008041 alkali metal carbonates Chemical class 0.000 claims description 5
- 229910052910 alkali metal silicate Inorganic materials 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 239000002888 zwitterionic surfactant Substances 0.000 claims description 5
- 239000001205 polyphosphate Substances 0.000 claims description 4
- 235000011176 polyphosphates Nutrition 0.000 claims description 4
- 229920000388 Polyphosphate Polymers 0.000 claims description 3
- 229910052816 inorganic phosphate Inorganic materials 0.000 claims description 3
- VKZRWSNIWNFCIQ-WDSKDSINSA-N (2s)-2-[2-[[(1s)-1,2-dicarboxyethyl]amino]ethylamino]butanedioic acid Chemical compound OC(=O)C[C@@H](C(O)=O)NCCN[C@H](C(O)=O)CC(O)=O VKZRWSNIWNFCIQ-WDSKDSINSA-N 0.000 claims description 2
- 238000013019 agitation Methods 0.000 claims 3
- 239000007864 aqueous solution Substances 0.000 claims 3
- 238000004900 laundering Methods 0.000 claims 3
- 229910000318 alkali metal phosphate Inorganic materials 0.000 claims 2
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims 1
- 235000013361 beverage Nutrition 0.000 abstract description 2
- 235000013305 food Nutrition 0.000 abstract description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 41
- 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 24
- 235000015424 sodium Nutrition 0.000 description 24
- 150000001875 compounds Chemical class 0.000 description 23
- 239000011734 sodium Substances 0.000 description 23
- 239000000463 material Substances 0.000 description 22
- 229910052708 sodium Inorganic materials 0.000 description 22
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical class OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 20
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 19
- 229910000323 aluminium silicate Inorganic materials 0.000 description 18
- 239000013522 chelant Substances 0.000 description 17
- 238000005342 ion exchange Methods 0.000 description 17
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
- 239000007859 condensation product Substances 0.000 description 14
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 238000011282 treatment Methods 0.000 description 12
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 10
- 239000003795 chemical substances by application Substances 0.000 description 10
- 229910052700 potassium Inorganic materials 0.000 description 10
- 239000011591 potassium Substances 0.000 description 10
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Natural products OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 9
- 235000014113 dietary fatty acids Nutrition 0.000 description 9
- 239000000194 fatty acid Substances 0.000 description 9
- 229930195729 fatty acid Natural products 0.000 description 9
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 9
- 239000002689 soil Substances 0.000 description 9
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 8
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- 150000004665 fatty acids Chemical class 0.000 description 8
- 239000002245 particle Substances 0.000 description 8
- 229920005646 polycarboxylate Polymers 0.000 description 8
- 238000004140 cleaning Methods 0.000 description 7
- 238000009472 formulation Methods 0.000 description 7
- 159000000001 potassium salts Chemical class 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 150000001412 amines Chemical class 0.000 description 6
- 239000007844 bleaching agent Substances 0.000 description 6
- 150000007942 carboxylates Chemical class 0.000 description 6
- 239000004927 clay Substances 0.000 description 6
- 235000001727 glucose Nutrition 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- 230000002209 hydrophobic effect Effects 0.000 description 6
- 239000004615 ingredient Substances 0.000 description 6
- YDSWCNNOKPMOTP-UHFFFAOYSA-N mellitic acid Chemical class OC(=O)C1=C(C(O)=O)C(C(O)=O)=C(C(O)=O)C(C(O)=O)=C1C(O)=O YDSWCNNOKPMOTP-UHFFFAOYSA-N 0.000 description 6
- 229910052698 phosphorus Inorganic materials 0.000 description 6
- 239000011574 phosphorus Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 239000003760 tallow Substances 0.000 description 6
- 235000013162 Cocos nucifera Nutrition 0.000 description 5
- 244000060011 Cocos nucifera Species 0.000 description 5
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 5
- QPCDCPDFJACHGM-UHFFFAOYSA-N N,N-bis{2-[bis(carboxymethyl)amino]ethyl}glycine Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(=O)O)CCN(CC(O)=O)CC(O)=O QPCDCPDFJACHGM-UHFFFAOYSA-N 0.000 description 5
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical class OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 5
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 5
- 150000001298 alcohols Chemical class 0.000 description 5
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical group OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 5
- 229910000019 calcium carbonate Inorganic materials 0.000 description 5
- 235000010216 calcium carbonate Nutrition 0.000 description 5
- 150000001720 carbohydrates Chemical group 0.000 description 5
- 239000008103 glucose Substances 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 235000014786 phosphorus Nutrition 0.000 description 5
- 229910000029 sodium carbonate Inorganic materials 0.000 description 5
- 238000001694 spray drying Methods 0.000 description 5
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 4
- BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical group [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 description 4
- 102000004190 Enzymes Human genes 0.000 description 4
- 108090000790 Enzymes Proteins 0.000 description 4
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 4
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
- 229930182556 Polyacetal Natural products 0.000 description 4
- 238000007792 addition Methods 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- 125000000129 anionic group Chemical group 0.000 description 4
- 229910001424 calcium ion Inorganic materials 0.000 description 4
- 235000019864 coconut oil Nutrition 0.000 description 4
- 239000003240 coconut oil Substances 0.000 description 4
- 229910052681 coesite Inorganic materials 0.000 description 4
- 229910052906 cristobalite Inorganic materials 0.000 description 4
- 229940012017 ethylenediamine Drugs 0.000 description 4
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 4
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 4
- 229920000728 polyester Polymers 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 229920006324 polyoxymethylene Polymers 0.000 description 4
- 229960004063 propylene glycol Drugs 0.000 description 4
- 235000013772 propylene glycol Nutrition 0.000 description 4
- 239000000377 silicon dioxide Substances 0.000 description 4
- 235000012239 silicon dioxide Nutrition 0.000 description 4
- 229940001593 sodium carbonate Drugs 0.000 description 4
- 235000019832 sodium triphosphate Nutrition 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 229910052682 stishovite Inorganic materials 0.000 description 4
- 230000002194 synthesizing effect Effects 0.000 description 4
- HLZKNKRTKFSKGZ-UHFFFAOYSA-N tetradecan-1-ol Chemical compound CCCCCCCCCCCCCCO HLZKNKRTKFSKGZ-UHFFFAOYSA-N 0.000 description 4
- 229910052905 tridymite Inorganic materials 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 3
- RAEOEMDZDMCHJA-UHFFFAOYSA-N 2-[2-[bis(carboxymethyl)amino]ethyl-[2-[2-[bis(carboxymethyl)amino]ethyl-(carboxymethyl)amino]ethyl]amino]acetic acid Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(=O)O)CCN(CCN(CC(O)=O)CC(O)=O)CC(O)=O RAEOEMDZDMCHJA-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical class C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 229910019142 PO4 Inorganic materials 0.000 description 3
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 3
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 3
- 244000269722 Thea sinensis Species 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000004996 alkyl benzenes Chemical class 0.000 description 3
- 150000001768 cations Chemical class 0.000 description 3
- 239000002738 chelating agent Substances 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- 125000003147 glycosyl group Chemical group 0.000 description 3
- 229910001385 heavy metal Inorganic materials 0.000 description 3
- 125000001165 hydrophobic group Chemical group 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 3
- MGFYIUFZLHCRTH-UHFFFAOYSA-N nitrilotriacetic acid Chemical class OC(=O)CN(CC(O)=O)CC(O)=O MGFYIUFZLHCRTH-UHFFFAOYSA-N 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- 239000002304 perfume Substances 0.000 description 3
- 235000021317 phosphate Nutrition 0.000 description 3
- 125000001453 quaternary ammonium group Chemical group 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 2
- 239000001124 (E)-prop-1-ene-1,2,3-tricarboxylic acid Substances 0.000 description 2
- PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 2
- CFPOJWPDQWJEMO-UHFFFAOYSA-N 2-(1,2-dicarboxyethoxy)butanedioic acid Chemical class OC(=O)CC(C(O)=O)OC(C(O)=O)CC(O)=O CFPOJWPDQWJEMO-UHFFFAOYSA-N 0.000 description 2
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- CYEJMVLDXAUOPN-UHFFFAOYSA-N 2-dodecylphenol Chemical compound CCCCCCCCCCCCC1=CC=CC=C1O CYEJMVLDXAUOPN-UHFFFAOYSA-N 0.000 description 2
- PSZAEHPBBUYICS-UHFFFAOYSA-N 2-methylidenepropanedioic acid Chemical compound OC(=O)C(=C)C(O)=O PSZAEHPBBUYICS-UHFFFAOYSA-N 0.000 description 2
- 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 244000299507 Gossypium hirsutum Species 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- KKCBUQHMOMHUOY-UHFFFAOYSA-N Na2O Inorganic materials [O-2].[Na+].[Na+] KKCBUQHMOMHUOY-UHFFFAOYSA-N 0.000 description 2
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 2
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 2
- 229910021536 Zeolite Inorganic materials 0.000 description 2
- 229940091181 aconitic acid Drugs 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- 150000001335 aliphatic alkanes Chemical group 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 125000005037 alkyl phenyl group Chemical group 0.000 description 2
- 125000005211 alkyl trimethyl ammonium group Chemical group 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 description 2
- WQZGKKKJIJFFOK-PHYPRBDBSA-N alpha-D-galactose Chemical group OC[C@H]1O[C@H](O)[C@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-PHYPRBDBSA-N 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- CMFFZBGFNICZIS-UHFFFAOYSA-N butanedioic acid;2,3-dihydroxybutanedioic acid Chemical compound OC(=O)CCC(O)=O.OC(=O)CCC(O)=O.OC(=O)C(O)C(O)C(O)=O CMFFZBGFNICZIS-UHFFFAOYSA-N 0.000 description 2
- HXDRSFFFXJISME-UHFFFAOYSA-N butanedioic acid;2,3-dihydroxybutanedioic acid Chemical compound OC(=O)CCC(O)=O.OC(=O)C(O)C(O)C(O)=O HXDRSFFFXJISME-UHFFFAOYSA-N 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 125000002091 cationic group Chemical group 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- GTZCVFVGUGFEME-IWQZZHSRSA-N cis-aconitic acid Chemical compound OC(=O)C\C(C(O)=O)=C\C(O)=O GTZCVFVGUGFEME-IWQZZHSRSA-N 0.000 description 2
- HNEGQIOMVPPMNR-IHWYPQMZSA-N citraconic acid Chemical compound OC(=O)C(/C)=C\C(O)=O HNEGQIOMVPPMNR-IHWYPQMZSA-N 0.000 description 2
- 229940018557 citraconic acid Drugs 0.000 description 2
- 229940096386 coconut alcohol Drugs 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 235000011389 fruit/vegetable juice Nutrition 0.000 description 2
- 239000001530 fumaric acid Substances 0.000 description 2
- 229960002598 fumaric acid Drugs 0.000 description 2
- 229930182830 galactose Chemical group 0.000 description 2
- 229940083124 ganglion-blocking antiadrenergic secondary and tertiary amines Drugs 0.000 description 2
- 229930182478 glucoside Natural products 0.000 description 2
- 150000008131 glucosides Chemical class 0.000 description 2
- 150000004676 glycans Polymers 0.000 description 2
- HHLFWLYXYJOTON-UHFFFAOYSA-N glyoxylic acid Chemical compound OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 description 2
- 235000019674 grape juice Nutrition 0.000 description 2
- 150000002402 hexoses Chemical class 0.000 description 2
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 238000005304 joining Methods 0.000 description 2
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 229940043348 myristyl alcohol Drugs 0.000 description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 2
- 229920000233 poly(alkylene oxides) Polymers 0.000 description 2
- 229920000058 polyacrylate Polymers 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 229920005862 polyol Polymers 0.000 description 2
- 150000003077 polyols Chemical class 0.000 description 2
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- 235000011181 potassium carbonates Nutrition 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- NNHHDJVEYQHLHG-UHFFFAOYSA-N potassium silicate Chemical compound [K+].[K+].[O-][Si]([O-])=O NNHHDJVEYQHLHG-UHFFFAOYSA-N 0.000 description 1
- 229910052913 potassium silicate Inorganic materials 0.000 description 1
- 235000019353 potassium silicate Nutrition 0.000 description 1
- VIDIKYSEHMODFW-UHFFFAOYSA-M potassium;3-carboxyoxy-2-methoxy-3-oxopropanoate Chemical compound [K+].COC(C([O-])=O)C(=O)OC(O)=O VIDIKYSEHMODFW-UHFFFAOYSA-M 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 150000003138 primary alcohols Chemical class 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- ROSDSFDQCJNGOL-UHFFFAOYSA-N protonated dimethyl amine Natural products CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 150000004023 quaternary phosphonium compounds Chemical class 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000011369 resultant mixture Substances 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 150000003333 secondary alcohols Chemical class 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910001388 sodium aluminate Inorganic materials 0.000 description 1
- 239000000429 sodium aluminium silicate Substances 0.000 description 1
- 235000012217 sodium aluminium silicate Nutrition 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M sodium bicarbonate Substances [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- FQENQNTWSFEDLI-UHFFFAOYSA-J sodium diphosphate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]P([O-])(=O)OP([O-])([O-])=O FQENQNTWSFEDLI-UHFFFAOYSA-J 0.000 description 1
- 235000019983 sodium metaphosphate Nutrition 0.000 description 1
- 229940048086 sodium pyrophosphate Drugs 0.000 description 1
- 229910052911 sodium silicate Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 230000003381 solubilizing effect Effects 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000000707 stereoselective effect Effects 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- JDVPQXZIJDEHAN-UHFFFAOYSA-N succinamic acid Chemical class NC(=O)CCC(O)=O JDVPQXZIJDEHAN-UHFFFAOYSA-N 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 235000011044 succinic acid Nutrition 0.000 description 1
- 230000001180 sulfating effect Effects 0.000 description 1
- DIORMHZUUKOISG-UHFFFAOYSA-N sulfoformic acid Chemical compound OC(=O)S(O)(=O)=O DIORMHZUUKOISG-UHFFFAOYSA-N 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 1
- 150000004026 tertiary sulfonium compounds Chemical class 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical class NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 1
- 235000019818 tetrasodium diphosphate Nutrition 0.000 description 1
- 239000001577 tetrasodium phosphonato phosphate Substances 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- UNXRWKVEANCORM-UHFFFAOYSA-I triphosphate(5-) Chemical compound [O-]P([O-])(=O)OP([O-])(=O)OP([O-])([O-])=O UNXRWKVEANCORM-UHFFFAOYSA-I 0.000 description 1
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 235000019871 vegetable fat Nutrition 0.000 description 1
- 235000020681 well water Nutrition 0.000 description 1
- 239000002349 well water Substances 0.000 description 1
- 229910009112 xH2O Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/16—Organic compounds
- C11D3/26—Organic compounds containing nitrogen
- C11D3/33—Amino carboxylic acids
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Detergent Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/929,549 US4704233A (en) | 1986-11-10 | 1986-11-10 | Detergent compositions containing ethylenediamine-N,N'-disuccinic acid |
| US929,549 | 1986-11-10 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1299459C true CA1299459C (en) | 1992-04-28 |
Family
ID=25458037
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000551358A Expired - Lifetime CA1299459C (en) | 1986-11-10 | 1987-11-09 | Detergent composition containing ethylenediamine-n,n'disuccinic acid |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US4704233A (enExample) |
| EP (1) | EP0267653B1 (enExample) |
| JP (1) | JPH0832914B2 (enExample) |
| AT (1) | ATE80177T1 (enExample) |
| AU (1) | AU589877B2 (enExample) |
| CA (1) | CA1299459C (enExample) |
| DE (1) | DE3781510T2 (enExample) |
| DK (1) | DK170174B1 (enExample) |
| EG (1) | EG18325A (enExample) |
| FI (1) | FI86554C (enExample) |
| GR (1) | GR3006314T3 (enExample) |
| IE (1) | IE60182B1 (enExample) |
| MA (1) | MA21105A1 (enExample) |
| MX (1) | MX165545B (enExample) |
| PH (1) | PH23087A (enExample) |
| TR (1) | TR23210A (enExample) |
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| US5531927A (en) * | 1992-03-20 | 1996-07-02 | Bio-Safe Specialty Products, Inc. | Stain removing compositions and methods of using the same |
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| US5269974A (en) * | 1992-09-01 | 1993-12-14 | The Procter & Gamble Company | Liquid or gel dishwashing detergent composition containing alkyl amphocarboxylic acid and magnesium or calcium ions |
| DE69322744T2 (de) * | 1992-11-16 | 1999-07-22 | The Procter & Gamble Co., Cincinnati, Ohio | Stabile, nichtionische Tensidemulsionen, welche Viskositätskontrollmittel enthalten |
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| US5569443A (en) * | 1994-11-18 | 1996-10-29 | The Dow Chemical Company | Method for removing hydrogen sulfide from a gas using polyamino disuccinic acid |
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| GB9322648D0 (en) * | 1993-11-03 | 1993-12-22 | Ass Octel | Process for the production of s.s.e.d.d.s |
| AU7932094A (en) * | 1993-11-03 | 1995-05-23 | Procter & Gamble Company, The | Control of calcium carbonate precipitation in automatic dishwashing |
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| GB9407942D0 (en) * | 1994-04-21 | 1994-06-15 | Procter & Gamble | Detergent compositions containing diamine tetracarboxylic acid or salts thereof |
| WO1995029220A1 (en) * | 1994-04-21 | 1995-11-02 | The Procter & Gamble Company | Detergent compositions containing diamine tetracarboxylic acid or salts thereof |
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| US5466867A (en) * | 1994-07-11 | 1995-11-14 | Albemarle Corporation | Method for producing [S,S]-ethylenediamine-N,N'-disuccinic acid from its calcium salt |
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| GB9422762D0 (en) * | 1994-11-11 | 1995-01-04 | Ass Octel | Use of a compound |
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| EP3561032A1 (en) | 2018-04-27 | 2019-10-30 | The Procter & Gamble Company | Antimicrobial hard surface cleaners comprising alkylpyrrolidones |
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| EP3569683B1 (en) | 2018-05-15 | 2020-10-14 | The Procter & Gamble Company | Liquid acidic hard surface cleaning compositions providing improved maintenance of surface shine, and prevention of water marks and splash marks |
| EP3569682B1 (en) | 2018-05-15 | 2022-12-07 | The Procter & Gamble Company | Liquid hard surface cleaning compositions having improved viscosity |
| EP3572491B1 (en) | 2018-05-24 | 2025-02-19 | The Procter & Gamble Company | Spray container comprising a detergent composition |
| EP3572489A1 (en) | 2018-05-24 | 2019-11-27 | The Procter & Gamble Company | Spray container comprising a detergent composition |
| EP3572492A1 (en) | 2018-05-24 | 2019-11-27 | The Procter & Gamble Company | Fine mist hard surface cleaning spray |
| EP3572490A1 (en) | 2018-05-24 | 2019-11-27 | The Procter & Gamble Company | Spray container comprising a detergent composition |
| JP7485617B2 (ja) | 2018-06-07 | 2024-05-16 | エコラボ ユーエスエー インコーポレイティド | 酵素による深鍋および平鍋用洗剤 |
| US20200015651A1 (en) | 2018-07-13 | 2020-01-16 | The Procter & Gamble Company | Cleaning article comprising multiple sheets and methods thereof |
| EP3771338A1 (en) | 2019-07-29 | 2021-02-03 | The Procter & Gamble Company | Acidic antimicrobial composition |
| EP3783091A1 (en) | 2019-08-20 | 2021-02-24 | The Procter & Gamble Company | Cleaning composition |
| EP3825392A1 (en) | 2019-11-21 | 2021-05-26 | Dalli-Werke GmbH & Co. KG | Detergent tablet comprising an effervescent system |
| EP4053254B1 (en) | 2021-03-04 | 2025-09-03 | The Procter & Gamble Company | Hard surface cleaning composition comprising polyalkylene glycol |
| CA3228918A1 (en) | 2021-08-10 | 2023-02-16 | Nippon Shokubai Co., Ltd. | Polyalkylene-oxide-containing compound |
| JP2024535405A (ja) | 2021-09-27 | 2024-09-30 | エスエイチピーピー グローバル テクノロジーズ べスローテン フェンノートシャップ | フィルム押出組成物および関連する押出フィルム、金属化フィルム、ならびにキャパシタ |
| EP4282944A1 (en) | 2022-05-27 | 2023-11-29 | Dalli-Werke GmbH & Co. KG | Unit dose for personal care or household care composition |
| CA3211776A1 (en) | 2022-09-08 | 2024-03-08 | The Procter & Gamble Company | Cleaning implement |
| EP4349174A1 (en) | 2022-10-05 | 2024-04-10 | The Procter & Gamble Company | Antimicrobial composition comprising a modified alkyl glycoside and an alkenediol |
| EP4349175A1 (en) | 2022-10-05 | 2024-04-10 | The Procter & Gamble Company | Antimicrobial composition comprising a modified alkyl glycoside and an organic acid |
| WO2025104259A2 (en) | 2023-11-17 | 2025-05-22 | Basf Se | Crystalline forms of s,s-ethylenediamine-n,n'-disuccinic acid, respective methods and uses |
| WO2025165928A1 (en) | 2024-01-30 | 2025-08-07 | The Procter & Gamble Company | Powered spray dispenser |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3158635A (en) * | 1959-03-18 | 1964-11-24 | Stauffer Chemical Co | Bis-adduction products and methods of preparing same |
| US3151084A (en) * | 1961-03-13 | 1964-09-29 | Swift & Co | Solubilizer for synthetic detergent |
| DE2125249A1 (de) * | 1971-05-21 | 1972-11-30 | Chemische Werke Hüls AG, 4370 Mari | Gerüstsubstanzen für Wasch- und Reinigungsmittel |
| FR2195594B1 (enExample) * | 1972-08-09 | 1974-10-25 | Santerre Orsan | |
| US3920564A (en) * | 1972-09-20 | 1975-11-18 | Colgate Palmolive Co | Softener-detergent composition |
| CA1037816A (en) * | 1973-10-26 | 1978-09-05 | Jack T. Inamorato | Liquid hydroxyalkyl iminodicarboxylate detergents |
| JPS5851994B2 (ja) * | 1979-12-05 | 1983-11-19 | 呉羽化学工業株式会社 | 無リン洗剤組成物 |
| US4412943A (en) * | 1981-02-23 | 1983-11-01 | Kao Soap Co., Ltd. | Liquid detergent composition |
| US4397776A (en) * | 1981-03-17 | 1983-08-09 | The Procter & Gamble Company | Liquid detergent compositions containing alpha-amine oxide surfactants |
| US4486339A (en) * | 1982-08-04 | 1984-12-04 | The Dow Chemical Company | Sequestering agent |
| US4507219A (en) * | 1983-08-12 | 1985-03-26 | The Proctor & Gamble Company | Stable liquid detergent compositions |
| US4560492A (en) * | 1984-11-02 | 1985-12-24 | The Procter & Gamble Company | Laundry detergent composition with enhanced stain removal |
-
1986
- 1986-11-10 US US06/929,549 patent/US4704233A/en not_active Expired - Lifetime
-
1987
- 1987-11-02 DK DK573287A patent/DK170174B1/da not_active IP Right Cessation
- 1987-11-06 EP EP87202158A patent/EP0267653B1/en not_active Expired - Lifetime
- 1987-11-06 PH PH36042A patent/PH23087A/en unknown
- 1987-11-06 DE DE8787202158T patent/DE3781510T2/de not_active Expired - Lifetime
- 1987-11-06 AT AT87202158T patent/ATE80177T1/de not_active IP Right Cessation
- 1987-11-09 IE IE300487A patent/IE60182B1/en not_active IP Right Cessation
- 1987-11-09 CA CA000551358A patent/CA1299459C/en not_active Expired - Lifetime
- 1987-11-09 MA MA21346A patent/MA21105A1/fr unknown
- 1987-11-10 TR TR773/87A patent/TR23210A/xx unknown
- 1987-11-10 EG EG649/87A patent/EG18325A/xx active
- 1987-11-10 MX MX009205A patent/MX165545B/es unknown
- 1987-11-10 JP JP62284090A patent/JPH0832914B2/ja not_active Expired - Lifetime
- 1987-11-10 AU AU80955/87A patent/AU589877B2/en not_active Expired
- 1987-11-10 FI FI874959A patent/FI86554C/fi not_active IP Right Cessation
-
1992
- 1992-11-24 GR GR920402673T patent/GR3006314T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ATE80177T1 (de) | 1992-09-15 |
| IE60182B1 (en) | 1994-06-15 |
| US4704233A (en) | 1987-11-03 |
| DK573287A (da) | 1988-05-11 |
| DK573287D0 (da) | 1987-11-02 |
| TR23210A (tr) | 1989-06-21 |
| MX165545B (es) | 1992-11-19 |
| EG18325A (en) | 1992-10-30 |
| GR3006314T3 (enExample) | 1993-06-21 |
| EP0267653B1 (en) | 1992-09-02 |
| FI86554B (fi) | 1992-05-29 |
| FI86554C (fi) | 1992-09-10 |
| JPS63199295A (ja) | 1988-08-17 |
| DE3781510T2 (de) | 1993-03-18 |
| EP0267653A2 (en) | 1988-05-18 |
| DE3781510D1 (de) | 1992-10-08 |
| MA21105A1 (fr) | 1988-07-01 |
| AU8095587A (en) | 1988-05-12 |
| EP0267653A3 (en) | 1989-03-15 |
| FI874959A0 (fi) | 1987-11-10 |
| IE873004L (en) | 1988-05-10 |
| FI874959L (fi) | 1988-05-11 |
| AU589877B2 (en) | 1989-10-19 |
| PH23087A (en) | 1989-04-10 |
| DK170174B1 (da) | 1995-06-06 |
| JPH0832914B2 (ja) | 1996-03-29 |
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