GB2041964A - Perfumed soap composition - Google Patents
Perfumed soap composition Download PDFInfo
- Publication number
- GB2041964A GB2041964A GB8003395A GB8003395A GB2041964A GB 2041964 A GB2041964 A GB 2041964A GB 8003395 A GB8003395 A GB 8003395A GB 8003395 A GB8003395 A GB 8003395A GB 2041964 A GB2041964 A GB 2041964A
- Authority
- GB
- United Kingdom
- Prior art keywords
- composition
- soap
- silicon
- silicon compound
- fragrance
- 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.)
- Granted
Links
- 239000000344 soap Substances 0.000 title claims abstract description 50
- 239000000203 mixture Substances 0.000 title claims abstract description 33
- 150000003377 silicon compounds Chemical class 0.000 claims abstract description 25
- 229910052710 silicon Inorganic materials 0.000 claims abstract description 11
- 239000010703 silicon Substances 0.000 claims abstract description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 5
- -1 monoterpene alcohols Chemical class 0.000 claims description 19
- 239000003205 fragrance Substances 0.000 claims description 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- IPZJQDSFZGZEOY-UHFFFAOYSA-N dimethylmethylene Chemical compound C[C]C IPZJQDSFZGZEOY-UHFFFAOYSA-N 0.000 claims description 7
- 239000007788 liquid Substances 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 239000007787 solid Substances 0.000 claims description 6
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 5
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 claims description 5
- 239000000194 fatty acid Substances 0.000 claims description 5
- 229930195729 fatty acid Natural products 0.000 claims description 5
- 229910000077 silane Inorganic materials 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 5
- 125000005083 alkoxyalkoxy group Chemical group 0.000 claims description 4
- 125000004122 cyclic group Chemical group 0.000 claims description 4
- 150000004665 fatty acids Chemical class 0.000 claims description 4
- 235000011837 pasties Nutrition 0.000 claims description 4
- 150000002989 phenols Chemical class 0.000 claims description 4
- 229930003651 acyclic monoterpene Natural products 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 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 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 2
- 229910052708 sodium Inorganic materials 0.000 claims description 2
- 239000011734 sodium Substances 0.000 claims description 2
- 229930003658 monoterpene Natural products 0.000 claims 1
- 235000002577 monoterpenes Nutrition 0.000 claims 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims 1
- GLZPCOQZEFWAFX-UHFFFAOYSA-N KU0063794 Natural products CC(C)=CCCC(C)=CCO GLZPCOQZEFWAFX-UHFFFAOYSA-N 0.000 abstract description 24
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 abstract description 15
- QMVPMAAFGQKVCJ-UHFFFAOYSA-N citronellol Chemical compound OCCC(C)CCC=C(C)C QMVPMAAFGQKVCJ-UHFFFAOYSA-N 0.000 abstract description 14
- GLZPCOQZEFWAFX-YFHOEESVSA-N Geraniol Natural products CC(C)=CCC\C(C)=C/CO GLZPCOQZEFWAFX-YFHOEESVSA-N 0.000 abstract description 10
- 239000005792 Geraniol Substances 0.000 abstract description 10
- 229940113087 geraniol Drugs 0.000 abstract description 10
- QMVPMAAFGQKVCJ-SNVBAGLBSA-N (R)-(+)-citronellol Natural products OCC[C@H](C)CCC=C(C)C QMVPMAAFGQKVCJ-SNVBAGLBSA-N 0.000 abstract description 7
- JGQFVRIQXUFPAH-UHFFFAOYSA-N beta-citronellol Natural products OCCC(C)CCCC(C)=C JGQFVRIQXUFPAH-UHFFFAOYSA-N 0.000 abstract description 7
- 235000000484 citronellol Nutrition 0.000 abstract description 7
- 229940067107 phenylethyl alcohol Drugs 0.000 abstract description 7
- 239000002304 perfume Substances 0.000 abstract description 5
- 239000004615 ingredient Substances 0.000 abstract description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 8
- 150000001298 alcohols Chemical class 0.000 description 8
- 238000000034 method Methods 0.000 description 6
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- 125000000962 organic group Chemical group 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- BFXIKLCIZHOAAZ-UHFFFAOYSA-N methyltrimethoxysilane Chemical compound CO[Si](C)(OC)OC BFXIKLCIZHOAAZ-UHFFFAOYSA-N 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- OOCCDEMITAIZTP-QPJJXVBHSA-N (E)-cinnamyl alcohol Chemical compound OC\C=C\C1=CC=CC=C1 OOCCDEMITAIZTP-QPJJXVBHSA-N 0.000 description 2
- MSHFRERJPWKJFX-UHFFFAOYSA-N 4-Methoxybenzyl alcohol Chemical compound COC1=CC=C(CO)C=C1 MSHFRERJPWKJFX-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- GLZPCOQZEFWAFX-JXMROGBWSA-N Nerol Natural products CC(C)=CCC\C(C)=C\CO GLZPCOQZEFWAFX-JXMROGBWSA-N 0.000 description 2
- BCKXLBQYZLBQEK-KVVVOXFISA-M Sodium oleate Chemical compound [Na+].CCCCCCCC\C=C/CCCCCCCC([O-])=O BCKXLBQYZLBQEK-KVVVOXFISA-M 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000003599 detergent Substances 0.000 description 2
- RRAFCDWBNXTKKO-UHFFFAOYSA-N eugenol Chemical compound COC1=CC(CC=C)=CC=C1O RRAFCDWBNXTKKO-UHFFFAOYSA-N 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- ZYTMANIQRDEHIO-KXUCPTDWSA-N isopulegol Chemical compound C[C@@H]1CC[C@@H](C(C)=C)[C@H](O)C1 ZYTMANIQRDEHIO-KXUCPTDWSA-N 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- PYJBVGYZXWPIKK-UHFFFAOYSA-M potassium;tetradecanoate Chemical compound [K+].CCCCCCCCCCCCCC([O-])=O PYJBVGYZXWPIKK-UHFFFAOYSA-M 0.000 description 2
- 230000000717 retained effect Effects 0.000 description 2
- RYYKJJJTJZKILX-UHFFFAOYSA-M sodium octadecanoate Chemical compound [Na+].CCCCCCCCCCCCCCCCCC([O-])=O RYYKJJJTJZKILX-UHFFFAOYSA-M 0.000 description 2
- 229940045870 sodium palmitate Drugs 0.000 description 2
- GGXKEBACDBNFAF-UHFFFAOYSA-M sodium;hexadecanoate Chemical compound [Na+].CCCCCCCCCCCCCCCC([O-])=O GGXKEBACDBNFAF-UHFFFAOYSA-M 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 239000003039 volatile agent Substances 0.000 description 2
- NOOLISFMXDJSKH-UTLUCORTSA-N (+)-Neomenthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@@H]1O NOOLISFMXDJSKH-UTLUCORTSA-N 0.000 description 1
- 239000001871 (1R,2R,5S)-5-methyl-2-prop-1-en-2-ylcyclohexan-1-ol Substances 0.000 description 1
- VAJVDSVGBWFCLW-UHFFFAOYSA-N 3-Phenyl-1-propanol Chemical compound OCCCC1=CC=CC=C1 VAJVDSVGBWFCLW-UHFFFAOYSA-N 0.000 description 1
- NPBVQXIMTZKSBA-UHFFFAOYSA-N Chavibetol Natural products COC1=CC=C(CC=C)C=C1O NPBVQXIMTZKSBA-UHFFFAOYSA-N 0.000 description 1
- NOOLISFMXDJSKH-UHFFFAOYSA-N DL-menthol Natural products CC(C)C1CCC(C)CC1O NOOLISFMXDJSKH-UHFFFAOYSA-N 0.000 description 1
- 239000005770 Eugenol Substances 0.000 description 1
- 239000004166 Lanolin Substances 0.000 description 1
- 235000019482 Palm oil Nutrition 0.000 description 1
- DYUQAZSOFZSPHD-UHFFFAOYSA-N Phenylpropyl alcohol Natural products CCC(O)C1=CC=CC=C1 DYUQAZSOFZSPHD-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- UVMRYBDEERADNV-UHFFFAOYSA-N Pseudoeugenol Natural products COC1=CC(C(C)=C)=CC=C1O UVMRYBDEERADNV-UHFFFAOYSA-N 0.000 description 1
- 241000220317 Rosa Species 0.000 description 1
- 239000004902 Softening Agent Substances 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000005864 Sulphur Substances 0.000 description 1
- BOTDANWDWHJENH-UHFFFAOYSA-N Tetraethyl orthosilicate Chemical compound CCO[Si](OCC)(OCC)OCC BOTDANWDWHJENH-UHFFFAOYSA-N 0.000 description 1
- ADKPKEZZYOUGBZ-UHFFFAOYSA-N [C].[O].[Si] Chemical compound [C].[O].[Si] ADKPKEZZYOUGBZ-UHFFFAOYSA-N 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 230000002009 allergenic effect Effects 0.000 description 1
- OOCCDEMITAIZTP-UHFFFAOYSA-N allylic benzylic alcohol Natural products OCC=CC1=CC=CC=C1 OOCCDEMITAIZTP-UHFFFAOYSA-N 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- YHWCPXVTRSHPNY-UHFFFAOYSA-N butan-1-olate;titanium(4+) Chemical compound [Ti+4].CCCC[O-].CCCC[O-].CCCC[O-].CCCC[O-] YHWCPXVTRSHPNY-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 125000004965 chloroalkyl group Chemical group 0.000 description 1
- 239000003240 coconut oil Substances 0.000 description 1
- 235000019864 coconut oil Nutrition 0.000 description 1
- 239000008139 complexing agent Substances 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229960002217 eugenol Drugs 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 230000009969 flowable effect Effects 0.000 description 1
- 238000001030 gas--liquid chromatography Methods 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 150000005826 halohydrocarbons Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 229940095045 isopulegol Drugs 0.000 description 1
- 229940039717 lanolin Drugs 0.000 description 1
- 235000019388 lanolin Nutrition 0.000 description 1
- 238000004900 laundering Methods 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 229940041616 menthol Drugs 0.000 description 1
- ZYTMANIQRDEHIO-UHFFFAOYSA-N neo-Isopulegol Natural products CC1CCC(C(C)=C)C(O)C1 ZYTMANIQRDEHIO-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000003346 palm kernel oil Substances 0.000 description 1
- 235000019865 palm kernel oil Nutrition 0.000 description 1
- 239000002540 palm oil Substances 0.000 description 1
- 230000002085 persistent effect Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 229940114930 potassium stearate Drugs 0.000 description 1
- ANBFRLKBEIFNQU-UHFFFAOYSA-M potassium;octadecanoate Chemical compound [K+].CCCCCCCCCCCCCCCCCC([O-])=O ANBFRLKBEIFNQU-UHFFFAOYSA-M 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- 229940095696 soap product Drugs 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
- 239000000126 substance Substances 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 description 1
- FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 description 1
- 235000012141 vanillin Nutrition 0.000 description 1
- 229940117960 vanillin Drugs 0.000 description 1
- 238000005406 washing Methods 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
- C11D9/00—Compositions of detergents based essentially on soap
- C11D9/04—Compositions of detergents based essentially on soap containing compounding ingredients other than soaps
- C11D9/44—Perfumes; Colouring materials; Brightening agents ; Bleaching agents
- C11D9/442—Perfumes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
-
- 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
- C11D3/50—Perfumes
- C11D3/502—Protected perfumes
- C11D3/507—Compounds releasing perfumes by thermal or chemical activation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Detergent Compositions (AREA)
Abstract
A soap composition which contains as a fragrance-imparting ingredient at least one silicon compound having attached to silicon at least one group -OR in which R represents the residue remaining after removal of the hydroxyl group from a perfume alcohol e.g. geraniol, citronellol or phenylethyl alcohol.
Description
SPECIFICATION
Soap composition
This invention relates to soap compositions containing certain silicon compounds as fragranceimparting ingredients.
Soaps are widely employed as cleansing agents for the skin and other substrates. In the form of, for example, shaving soaps they are also employed as softening agents. It is usual to incorporate a perfume into many types of soap, especially when the soap is intended for personal cleansing and for the laundering of wearing apparel. The perfume endows the soap product with an aesthetic appeal and also enables a pleasant fragrance to be imparted to the substrate washed with the soap. Typical of the perfumes usually employed are those based on the essential alcohols e.g. geraniol, citronellol and phenylethyl alcohol.
We have now found that certain silicon-modified essential alcohols can be employed as fragrance-imparting additives for soaps. We have also found that the fragrance imparted by such silicon compounds is usually at least as persistent as that imparted by the corresponding siliconfree alcohols and at least in some cases can persist for a longer period.
According to this invention there is provided a liquid, pasty or solid soap composition which contains as a fragrance-imparting component at least one silicon compound having attached to silicon at least one group of the general formula -OR wherein R represents the residue remaining after removal of the hydroxyl group from an alcohol selected from cyclic and acyclic monoterpene alcohols, essential aryl-substituted aliphatic alcohols and essential aliphaticsubstituted phenols.
This invention also provides a process for preparing a soap composition which comprises forming a liquid, pasty or solid soap composition containing a silicon-containing fragranceimparting component of the type hereabove defined.
Any silicon compound containing at least one of the specified silicon-bonded -OR groups in the molecule may be employed in the compositions of this invention. Thus, the silicon compound may be for example a silane, di- or poly-silane, a siloxane or a silalkylene-siloxane.
Preferred as the silicon compounds are (i) silanes represented by the general formula RlnSi(OR)4 n and (ii) siloxanes having at least one structural unit of the formula
any remaining units in the siloxane having the formula
where R is as defined hereinabove, R' and R" each represent a hydrogen atom or an organic group free of sulphur and phosphorus and attached to the silicon atom through a silicon to carbon or silicon-oxygen-carbon linkage, n is 0, 1, 2 or 3, a has a value of 0, 1 or 2, b has a value of 1 or 2, the sum of a and b being not greater than 3, and c has a value of 0, 1, 2 or 3.
In the silicon compounds employed according to this invention the group R represents the residue remaining after removal of the hydroxyl group from an alcohol selected from cyclic and acyclic monoterpene alcohols, essential aryl-substituted aliphatic alcohols and essential aliphaticsubstituted phenols. Such alcohols are well known substances and include geraniol, citronellol, nerol, rhodinol, menthol, isopulegol, eugenol, vanillin, phenylethyl alcohol, phenylpropyl alcohol, anisyl alcohol, and cinnamyl alcohol. If desired more than one type of OR group may be present in a given molecule of the silicon compound. Depending on the nature of the fragrance desired the silicon compound may have R groups derived from, for example, both geraniol and phenylethyl alcohol or from nerol and anisyl alcohol.The preferred alcohols are the rose alcohols and essential aryl-substituted aliphatic alcohols. Preferably, therefore, R represents a group selected from -CH2CH = C(CH3)(CH2)2CH = C(CH3)2, -(CH2)2CH3CH(CH2)2CH = C(CH3)2, -(CH2)2C6H5, -(CH2)3C6H5, -CH2PhOCH3 in which Ph represents phenylene, and -CH2CH = CHC6H5.
Any substituents present in the silicon compounds in addition to the OR groups are hydrogen atoms and/or organic groups bonded to silicon through an SiC or SiOC linkage. Such organic groups, including R' and R", are preferably monovalent hydrocarbon groups, for example alkyl, alkenyl, aryl, alkaryl or aralkyl or monovalent groups composed of carbon, hydrogen and oxygen, for example alkoxy, alkoxyalkoxy or aryloxy. The SiC bonded organic groups may, however, also be monovalent halohydrocarbon groups such as chloroalkyl and choloroaryl.
Specific examples of the organic substituents which may be present in addition to the OR groups are methyl, ethyl, propyl, butyl, 2,4,4-trimethylpentyl, octadecyl, phenyl, benzyl, tolyl, methoxy, ethoxy, butoxy, methoxyethoxy, phenoxy, benzyloxy, -(CH2)3(OCH2CH2)8OC4H9.
-CH2CH2OCH2CH3,
-(CH2)3NH2, -(CH2)3NH(CH2)2NH2, -CH2CH2CH(CH3)NH(CH2)2NH2 and
+ -(CH2)3N(CH3)2C18H37CI.
Preferably any substituents present in addition to the OR groups are selected from hydrogen atoms, methyl groups and alkoxy and alkoxyalkoxy groups having less than 5 carbon atoms.
When siloxanes are employed as the silicon compounds according to this invention they may be homopolymers containing only units of general formula (I) or they may consist of such units together with one or more units defined by general formula (Il) hereinabove. Depending on the proportions and types of units present the siloxanes may have on average from less than 1.0 up to 3 total substituents per silicon atom and may vary from freely flowing liquid to resinous solids.
Examples of the silicon compounds which can be employed as the fragrance-imparting component in the compositions of this invention are CH3(OCH3)2SiOR (CH3)3SiOR (OC2H5)3SiOR
Si(OR)4
C6H5Si(OR)3
CH2 = CHSi(OC2H5)(0R)2
C8H17Si(OR)3 HSi(OR)3 Cl(CH2)3Si(OR)3 H2N(CH2)2NH(CH2)3Si(CH3)(OR)2
and partial hydrolysates of alkoxy silanes, e.g. of Si(OC2H5)4 and CH3Si(OCH3)3, wherein some or all of the alkoxy groups have been replaced by OR groups.
The silicon compounds employed according to this invention may be prepared by the reaction of the appropriate alcohol, e.g. geraniol or phenylethyl alcohol, with a silicon compound having silicon-bonded chlorine atoms or hydrogen atoms. It is usually preferred however to prepare the desired silicon compound by reacting the essential alcohol with a silicon compound having alkoxy or alkoxyalkoxy groups whereby some or all of such groups are replaced by the alcohol residue. Some reaction can take place merely by bringing the two reactants together. It is preferred, however, to expedite the reaction by the use of elevated temperatures and/or suitable catalysts such as potassium carbonate, sodium hydroxide and metal organic compounds, e.g.
tetrabutyl titanate.
The compositions of this invention can be based on any soap component. Soaps are predominantly the alkali metal salts, most usually the sodium and potassium, of the higher fatty acids, particularly those having from about 1 2 to about 1 8 carbon atoms. Such fatty acids may be derived from e.g. tallow, coconut oil, palm oil, palm kernel oil and lard. The soap component may therefore comprise, for example, sodium palmitate, sodium stearate, sodium oleate, potassium stearate or potassium myristate. Although the composition may be based on one soap, commercial soap cleansing agents generally contain two or more soaps, for example, mixtures of sodium palmitate, sodium stearate and sodium oleate. Shaving soaps generally contain the potassium salts of the fatty acids such as potassium myristate.In addition to the soap and fragrance-imparting components, the soap compositions of this invention may contain additives to improve the performance of the soap or to obtain special effects therein. Examples of such additives are superfatting agents e.g. lanolin and derivatives thereof, fatty alcohols and fatty acid monoglycerides, antibacterial agents, dyes, pigments, complexing agents, thickening agents and lubricants. The soap compositions of this invention may take the form of flowable liquids or pastes, for example as in some shaving soaps and creams, or they may be solid masses such as blocks, bars, tablets or similar shaped, non-powdered, non-granular materials, for example as is the case with most toilet soaps.
The soap compositions of this invention can be prepared by any of the techniques conventional in soap-making. Suitable techniques are widely practised and well described in the technical literature. The proportion of the fragrance-imparting component incorporated into the composition is not critical and may vary from very small, e.g. 0.01% by weight, to relatively large amounts, depending generally on the intensity and durability of fragrance desired.
Preferably the fragrance-imparting silicon compound is present in a proportion of from 0.1 to 5% by weight based on the total weight of the composition. More than one silicon-containing fragrance-imparting compound may be incorporated into the soap composition. As with conventional organic perfumes several compounds may be blended to achieve a particular fragrance. Alternatively, there may be employed one or more silicon compounds wherein the OR groups are derived from two or more different essential alcohols. Also, if desired the silicon compounds(s) may be employed in conjunction with one or more of the essential alcohols per se.
The following examples in which the parts are expressed by weight,
Me represents the methyl group.
X ,, -OCH2CH = C(CH3)(CH2)2CH = C(CH3)2
Y ,, -O(CH2)2CH3CH(CH2)2CH = C(CH3)2 z ,, -O(CH2)2C6H5 illustrate the invention.
Example 1
Me Si(OMe)3 (13.6 parts) was refluxed with geraniol (30.8 parts) under a positive nitrogen pressure for 28 hours during which methyl alcohol was removed by means of a Dean and Stark apparatus. The resulting reaction mixture (Silane A) was found by gas-liquid chromatography to have the follow composition by weight.
Me Si(OMe)3/MeOH 2.4%
HO CH2CH = C(CH3)(CH2)2CH = C(CH3)2 14.2%
Me Si(OMe)2 X 13.0% Me Si(OMe) X2 48.5%
Me SiX3 21.9%
Ten parts of an unperfumed, non-allergenic soap sold as simple soap was chopped into flakes and rendered to a creamy consistency by thoroughly mixing the flakes with pentane (10 parts) and Silane A (0.5 parts). The soap was moulded into a block and the pentane removed under vacuum with the application of mild heat.
For comparison a further block of soap was prepared using the same ingredients and method except that Silane A was replaced with the same amount of geraniol. Each block was used to wash one hand of a test subject and the presence of residual geraniol fragrance on each hand checked over a period of time. After 3 hours no residual fragrance was detectable on the hand washed with the comparison soap whereas the hand washed with the silane-containing soap retained a geraniol fragrance for about 5 hours.
Example 2
Employing a 20 litre reaction vessel citronellol (9.378 kg.) was reacted with methyl trimethoxysilane (4.08 kg.) in the presence of a catalyst. The silane was added to the citroneliol at a rate of 44 g. per minute and external heat provided. A vigorously exothermic reaction occurred during which the reaction temperature rose from 50 to 80"C. The reaction mixture was then allowed to cool and volatiles, predominantly methyl alcohol, were removed under vacuum,
The product remaining (Silane B) contained the following:
Me Si(OMe)2Y 11.0% by wt.
Me Si(OMe)Y2 36.6% by wt.
Me Si Y3 38.3% bywt.
together with small percentages of unreacted starting materials and by-products e.g. methyl alcohol.
Silane B was incorporated into an unperfumed soap employing the procedure and proportions of Example 1. For comparison a similar soap composition was prepared except that Silane B was replaced with the same amount of citronellol. The soaps were compared for residual fragrance by the washing test described in Example 1. The hand which had been washed with the soap containing Silane B retained the citronellol fragrance for about 5 hours. No residual fragrance was detectable after 0.5 hour on the hand washed with the control soap.
Example 3
Employing the same general procedure described in Example 2 phenylethyl alcohol (7.32 kg.) was reacted with methyltrimethoxysilane (4.08 kg.). After removal of volatiles under vacuum the product (9.2 kg.) (Silane C) contained
Me Si(OMe)2Z 10.5% by wt.
Me Si(OMe)Z2 32.8% by wt.
Me Z2 Si O Si Z2 Me 45.7% by wt.
together with small percentages of unreacted starting materials and by-products e.g. methyl alcohol.
Silane C was incorporated into a soap composition and the product tested according to the procedures described in Example 1. The soap containing Silane C imparted a fragrance which persisted for 2 hours. The fragrance imparted by the control soap containing phenyl-ethyl alcohol was detectable for only 0.5 hr.
Example 4
A trimethylsiloxy-terminated polymer of MeHSiO units having a molecular weight of about 2500 (30 parts) was mixed with anhydrous potassium carbonate (0.1 part). This mixture was heated to 40"C, and 36 parts of a mixture of equal weights of geraniol, citronellol and phenylethyl alcohol added dropwise during 45 minutes. Heating was continued and the temperature of the reaction mixture maintained at about 1 30 C for 5 hours. Hydrogen was evolved during the reaction to leave a colourless, viscous, liquid siloxane having silicon-bonded
Me, X, Y and Z groups together with residual unreacted silicon bonded hydrogen atoms.
This siloxane was incorporated into a soap and its fragrance imparting properties tested as described in Example 1. It was found that the fragrance imparted to the skin by the soap persisted for at least 6 hours.
Claims (8)
1. A liquid, pasty or solid soap composition which contains as a fragrance imparting component at least one silicon compound having attached to silicon at least one group of the general formula -OR wherein R represents the residue remaining after removal of the hydroxyl group from an alcohol selected from cyclic and acylic monoterpene alcohols, essential arylsubstituted aliphatic alcohols and essential aliphatic-substituted phenols.
2. A soap composition as claimed in claim 1 wherein the soap component comprises at least one sodium or potassium salt of a C,2 to C,8 fatty acid.
3. A composition as claimed in claim 1 or claim 2 wherein the silicon compound is a silane or a siloxane.
4. A composition as claimed in any one of the preceding claims wherein R represents a group selected from -CH2CH = C(CH3)(CH2)2CH = C(CH3)2 -(CH2)2CH3CH(CH2)2CH = C(CH3)2, -(CH2)2C6H5, -(CH2)3C6H5, -CH2Ph O CH3, in which Ph represents phenylene and -CH2CH = CH C8H5
5. A composition as claimed in any one of the preceding claims wherein any substituents present in the silicon compound in addition to the -OR groups are selected from hydrogen atoms, methyl groups and alkoxy and alkoxyalkoxy groups having less than 5 carbon atoms.
6. A composition as claimed in any one of the preceding claims wherein the silicon compound is present in a proportion of from 0.1 to 5% by weight based on the total weight of the soap composition.
7. A composition as claimed in claim 1 substantially as described with reference to the
Examples herein.
8. A process for preparing a soap composition which comprises forming a liquid, pasty or solid soap composition which contains as a fragrance-imparting component at least one silicon compound having attached to silicon at least one group of the general formula -OR wherein R represents the residue remaining after removal of the hydroxyl group from an alcohol selected from cyclic and acyclic monoterpene alcohols, essential aryl-substituted aliphatic alcohols and essential aliphatic-substituted phenols.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB7903633 | 1979-02-01 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| GB2041964A true GB2041964A (en) | 1980-09-17 |
| GB2041964B GB2041964B (en) | 1983-02-02 |
Family
ID=10502901
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB8003395A Expired GB2041964B (en) | 1979-02-01 | 1980-01-31 | Perfumed soap composition |
Country Status (7)
| Country | Link |
|---|---|
| JP (1) | JPS55129499A (en) |
| BE (1) | BE881464A (en) |
| CH (1) | CH643295A5 (en) |
| DE (1) | DE3003494A1 (en) |
| FR (1) | FR2447963A1 (en) |
| GB (1) | GB2041964B (en) |
| IT (1) | IT1209302B (en) |
Cited By (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5154849A (en) * | 1990-11-16 | 1992-10-13 | The Procter & Gamble Company | Mild skin cleansing toilet bar with silicone skin mildness/moisturizing aid |
| WO1996028497A1 (en) * | 1995-03-15 | 1996-09-19 | Firmenich S.A. | Novel polysiloxanes, use thereof in fragrances, and method for preparing same |
| GB2319527A (en) * | 1996-11-22 | 1998-05-27 | Gen Electric | Fragrance releasing non-volatile polysiloxanes |
| EP0982313A2 (en) * | 1998-08-28 | 2000-03-01 | General Electric Company | Fragrance releasing olefinic silanes |
| EP0982023A2 (en) * | 1998-08-28 | 2000-03-01 | General Electric Company | Emulsions of fragrance releasing silicon compounds |
| US6054547A (en) * | 1998-08-28 | 2000-04-25 | General Electric Company | Fragrance releasing non-volatile polymeric-siloxanes |
| US6075111A (en) * | 1998-08-28 | 2000-06-13 | General Electric Company | Fragrance releasing non-volatile polymeric siloxanes |
| WO2001068037A2 (en) * | 2000-03-16 | 2001-09-20 | Henkel Kommanditgesellschaft Auf Aktien | Silicic acid ester mixtures |
| WO2008065072A1 (en) | 2006-11-27 | 2008-06-05 | Henkel Ag & Co. Kgaa | Cleansing or care product |
| WO2008113820A2 (en) * | 2007-03-19 | 2008-09-25 | Momentive Performance Materials Gmbh | Reactive polyorganosiloxanes modified with aromatic substances |
| DE102007012910A1 (en) * | 2007-03-19 | 2008-09-25 | Momentive Performance Materials Gmbh | Fragrance-modified, branched polyorganosiloxanes |
| US7576170B2 (en) | 2003-12-19 | 2009-08-18 | Momentive Performance Materials | Cyclic siloxane compositions for the release of active ingredients |
| US7579495B2 (en) | 2003-12-19 | 2009-08-25 | Momentive Performance Materials Inc. | Active-releasing cyclic siloxanes |
| US8557262B2 (en) | 2008-09-12 | 2013-10-15 | Firmenich Sa | Divinyl ether derivatives capable of releasing active aldehydes and ketones and methods of use for perfuming surfaces |
| US8822404B2 (en) | 2010-06-10 | 2014-09-02 | Firmenich Sa | Perfuming compositions and uses thereof |
| US9000052B2 (en) | 2008-10-21 | 2015-04-07 | Firmenich Sa | Perfuming compositions and uses thereof |
| US9101783B2 (en) | 2009-06-19 | 2015-08-11 | Firmenich Sa | Malodor counteracting compositions and method for their use to counteract sweat malodor |
| US11192904B2 (en) | 2014-11-14 | 2021-12-07 | The Procter & Gamble Company | Silicone compounds comprising a benefit agent moiety |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19841147A1 (en) * | 1998-09-09 | 2000-03-16 | Henkel Kgaa | Kiselsäureester |
| DE102008053519A1 (en) | 2008-02-20 | 2009-09-03 | Henkel Ag & Co. Kgaa | Esterified oligomeric or polymeric silicic acid with a surfactant comprising an alkoxy group useful e.g. in washing or cleaning agent and cosmetic products, and for cleaning of textiles and hard surfaces |
| MX343010B (en) | 2011-10-27 | 2016-10-21 | Firmenich & Cie | Perfuming compositions and uses thereof. |
| WO2013064412A2 (en) | 2011-11-04 | 2013-05-10 | Firmenich Sa | Perfuming compositions and uses thereof |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3271305A (en) * | 1961-09-01 | 1966-09-06 | Dan River Mills Inc | Textile treatments and treated textiles |
| US3215719A (en) * | 1961-09-01 | 1965-11-02 | Dan River Mills Inc | Silicate esters of essential alcohols |
| GB1365063A (en) * | 1970-07-01 | 1974-08-29 | Bush Boake Allen Ltd | Oligomeric organic titanium and zirconium compounds and solid was hing compositions comprising them |
| IT1100671B (en) * | 1977-10-15 | 1985-09-28 | Dow Corning Ltd | DETERGENT COMPOSITIONS |
-
1980
- 1980-01-25 IT IT8019457A patent/IT1209302B/en active
- 1980-01-31 DE DE19803003494 patent/DE3003494A1/en active Granted
- 1980-01-31 BE BE0/199198A patent/BE881464A/en unknown
- 1980-01-31 JP JP1084380A patent/JPS55129499A/en active Pending
- 1980-01-31 GB GB8003395A patent/GB2041964B/en not_active Expired
- 1980-01-31 FR FR8002132A patent/FR2447963A1/en active Granted
- 1980-02-01 CH CH84880A patent/CH643295A5/en not_active IP Right Cessation
Cited By (32)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5154849A (en) * | 1990-11-16 | 1992-10-13 | The Procter & Gamble Company | Mild skin cleansing toilet bar with silicone skin mildness/moisturizing aid |
| WO1996028497A1 (en) * | 1995-03-15 | 1996-09-19 | Firmenich S.A. | Novel polysiloxanes, use thereof in fragrances, and method for preparing same |
| GB2319527B (en) * | 1996-11-22 | 2001-05-09 | Gen Electric | Fragrance releasing non-volatile polymeric siloxanes |
| GB2319527A (en) * | 1996-11-22 | 1998-05-27 | Gen Electric | Fragrance releasing non-volatile polysiloxanes |
| FR2756291A1 (en) * | 1996-11-22 | 1998-05-29 | Gen Electric | NON-VOLATILE POLYMERIC SILICONES RELEASING AGREABLE ODOR |
| US6322777B1 (en) | 1998-08-28 | 2001-11-27 | General Electric Company | Fragrance releasing non-volatile polymeric siloxanes |
| EP0982313A2 (en) * | 1998-08-28 | 2000-03-01 | General Electric Company | Fragrance releasing olefinic silanes |
| US6054547A (en) * | 1998-08-28 | 2000-04-25 | General Electric Company | Fragrance releasing non-volatile polymeric-siloxanes |
| US6075111A (en) * | 1998-08-28 | 2000-06-13 | General Electric Company | Fragrance releasing non-volatile polymeric siloxanes |
| US6077923A (en) * | 1998-08-28 | 2000-06-20 | General Electric Company | Fragrance releasing non-volatile polymeric siloxanes |
| US6083901A (en) * | 1998-08-28 | 2000-07-04 | General Electric Company | Emulsions of fragrance releasing silicon compounds |
| US6153578A (en) * | 1998-08-28 | 2000-11-28 | General Electric Company | Fragrance releasing olefinic silanes |
| EP0982023A2 (en) * | 1998-08-28 | 2000-03-01 | General Electric Company | Emulsions of fragrance releasing silicon compounds |
| EP0982023A3 (en) * | 1998-08-28 | 2001-06-20 | General Electric Company | Emulsions of fragrance releasing silicon compounds |
| US6046156A (en) * | 1998-08-28 | 2000-04-04 | General Electric Company | Fragrance releasing olefinic silanes |
| EP0982313A3 (en) * | 1998-08-28 | 2001-10-24 | General Electric Company | Fragrance releasing olefinic silanes |
| US7098178B2 (en) | 2000-03-16 | 2006-08-29 | Henkel Kommanditgesellschaft Auf Aktien (Henkel Kgaa) | Silicic acid ester mixtures |
| WO2001068037A2 (en) * | 2000-03-16 | 2001-09-20 | Henkel Kommanditgesellschaft Auf Aktien | Silicic acid ester mixtures |
| WO2001068037A3 (en) * | 2000-03-16 | 2002-02-14 | Henkel Kgaa | Silicic acid ester mixtures |
| US7576170B2 (en) | 2003-12-19 | 2009-08-18 | Momentive Performance Materials | Cyclic siloxane compositions for the release of active ingredients |
| EP2281545A1 (en) | 2003-12-19 | 2011-02-09 | General Electric Company | Cyclic siloxane compositions for the release of active ingredients |
| US7579495B2 (en) | 2003-12-19 | 2009-08-25 | Momentive Performance Materials Inc. | Active-releasing cyclic siloxanes |
| WO2008065072A1 (en) | 2006-11-27 | 2008-06-05 | Henkel Ag & Co. Kgaa | Cleansing or care product |
| WO2008113820A2 (en) * | 2007-03-19 | 2008-09-25 | Momentive Performance Materials Gmbh | Reactive polyorganosiloxanes modified with aromatic substances |
| WO2008113820A3 (en) * | 2007-03-19 | 2009-01-08 | Momentive Performance Mat Inc | Reactive polyorganosiloxanes modified with aromatic substances |
| DE102007012909A1 (en) * | 2007-03-19 | 2008-09-25 | Momentive Performance Materials Gmbh | Fragrance-modified, reactive polyorganosiloxanes |
| DE102007012910A1 (en) * | 2007-03-19 | 2008-09-25 | Momentive Performance Materials Gmbh | Fragrance-modified, branched polyorganosiloxanes |
| US8557262B2 (en) | 2008-09-12 | 2013-10-15 | Firmenich Sa | Divinyl ether derivatives capable of releasing active aldehydes and ketones and methods of use for perfuming surfaces |
| US9000052B2 (en) | 2008-10-21 | 2015-04-07 | Firmenich Sa | Perfuming compositions and uses thereof |
| US9101783B2 (en) | 2009-06-19 | 2015-08-11 | Firmenich Sa | Malodor counteracting compositions and method for their use to counteract sweat malodor |
| US8822404B2 (en) | 2010-06-10 | 2014-09-02 | Firmenich Sa | Perfuming compositions and uses thereof |
| US11192904B2 (en) | 2014-11-14 | 2021-12-07 | The Procter & Gamble Company | Silicone compounds comprising a benefit agent moiety |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2447963A1 (en) | 1980-08-29 |
| GB2041964B (en) | 1983-02-02 |
| DE3003494A1 (en) | 1980-08-07 |
| DE3003494C2 (en) | 1987-11-05 |
| IT8019457A0 (en) | 1980-01-25 |
| BE881464A (en) | 1980-07-31 |
| CH643295A5 (en) | 1984-05-30 |
| IT1209302B (en) | 1989-07-16 |
| FR2447963B1 (en) | 1983-07-29 |
| JPS55129499A (en) | 1980-10-07 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PCNP | Patent ceased through non-payment of renewal fee |