CA1110806A - Compositions containing silicon compounds - Google Patents

Compositions containing silicon compounds

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Publication number
CA1110806A
CA1110806A CA313,503A CA313503A CA1110806A CA 1110806 A CA1110806 A CA 1110806A CA 313503 A CA313503 A CA 313503A CA 1110806 A CA1110806 A CA 1110806A
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silicon
composition
compound
fragrance
essential
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CA313,503A
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French (fr)
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Bryan E. Cooper
Alan J. Mcardle
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    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/643—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicon in the main chain
    • D06M15/6436—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicon in the main chain containing amino groups
    • 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
    • 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
    • C08G77/38—Polysiloxanes modified by chemical after-treatment
    • 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
    • C11D3/162—Organic compounds containing Si
    • 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
    • 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
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
    • D06M13/46—Compounds containing quaternary nitrogen atoms
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/50—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with organometallic compounds; with organic compounds containing boron, silicon, selenium or tellurium atoms
    • D06M13/503—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with organometallic compounds; with organic compounds containing boron, silicon, selenium or tellurium atoms without bond between a carbon atom and a metal or a boron, silicon, selenium or tellurium atom
    • D06M13/507—Organic silicon compounds without carbon-silicon bond
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/50—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with organometallic compounds; with organic compounds containing boron, silicon, selenium or tellurium atoms
    • D06M13/51—Compounds with at least one carbon-metal or carbon-boron, carbon-silicon, carbon-selenium, or carbon-tellurium bond
    • D06M13/513—Compounds with at least one carbon-metal or carbon-boron, carbon-silicon, carbon-selenium, or carbon-tellurium bond with at least one carbon-silicon bond
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/643—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicon in the main chain
    • D06M15/65—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicon in the main chain containing epoxy groups

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Textile Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Inorganic Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Detergent Compositions (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Fats And Perfumes (AREA)
  • Silicon Polymers (AREA)

Abstract

Asstract of the Disclosure A textile fabric conditioner composition comprising a fatty alkyl quaternary ammonium compound and an ingredient for imparting fragrance to the treated fabric. The fragrance imparting ingredient consists of one or more silicon compounds having at least one silicon-bonded -OR
group in which 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.

Description

This invention relates to a fabric conditioner composition containing at least one silicon compound as a fragrance imparting component.
It is often desired to impart to substrates, for example fabrics such as wearing apparel and bed linen, a fresh and pleasant smell. As the fragrance imparting substances there are usually employed the essential oils either individually or as blends. The fragrance imparted by such oils is however generally of short duration.
U.S. Patent No. 3,215,719 discloses that a long lasting fragrance may be imparted to textiles if there are applied thereto certain silicate esters of essential alcohols. According to the teaching of said U.S. patent a particularly useful method of treating the textile is to pad it through an aqueous dispersion of the silicate ester. Such a method relies on a single relatively heavy application of the perfume which eventually dissipates. A more desirable arrangement would be that which involved a more frequent application of a lower add on of perfume, provided that such application could be carried out during a routine operation, such as laundering, to which the fabrics are periodically subjected. Such a technique would enable a more frequent change of fragrance, if desired, and would also permit renewal of the fragrance by a sinyle household operation.
According to this invention there is provided a fabric conditioner composition comprising a fatty alkyl X q~

quaternary ammonium compound and as a fragrance imparting component at least one silicon compound having in the molecule 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 phenols, any other substituents attached to silicon being selected from hydrogen atoms and organic groups free of sulphur and phosphorous, said organic groups being joined 1~ to silicon through a silicone to carbon or silicon-oxygen-carbon linkage.
The invention also includes a process for preparing such a fabric conditioner composition which comprises mixing a fatty alkyl quaternary compound and a silicon compound as hereinabove defined.
Any silicon compound containing at least one of the specified silicon-bonded -OR groups in the molecule may be employed in the composition of this invention. Thus, the silicon compound may be for example a silane, di- or poly-silane a siloxane or asilalkylene-siloxane. Preferred as the silicon compounds are ti) silanes represented by the general formula R'nSitOR)4-n and (ii) siloxanes having at least one structural unit of the formula ~r 8~6 ~RO)bSio4 a b any remaining units in the siloxane having the formula R.csio4 c ~~- (II)
-2 wherein R is as defined hereinabove, R' and R" each represent a hydrogen atom or an organic group free of sulphur and phosphorus and attacheed to the silicon atom through a silicon to carbon or silicon-oxygen-carbon linkage, n is O, 1, 2 or 3, a has a value of O, 1 or 2, b has a value of O, 1 or 2, the sum of a and b being not greater than 3 and c has a value of O, 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 2Q essential aliphatic-substituted 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 desixed more than one type of OR group may be present in a given molecule of the silicon compound. Depending on the nature of fragrance desired the silicon compound may have ~ groups derived from, for example, both geraniol and phenylethyl alcohol or from nerol and anisyl alcohol.

8~6 The preferred alcohols are the rose alcohols and essential aryl-substitued aliphatic alcohols.
Preferably, therefore, R represents a group selected from -cH2cH~c(cH3)(cH2)2cH=c(cH3)~
-(CH )2CH3CH(CH2)2CH=C(CH3)2 (CH2)2C6 5, 2 3 6 5 -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, al~enyl, aryl, alkaryl or aralkyl or monovalent groups o~osed of carbon,- hydrogen and oxygen, for example alkoxy, alkoxyalkoxy or aryloxy. The SiC bonded organic groups may, however, also be monovalent halo-hydrocarbon groups such as chloroalkyl and chloroaryl.
Specific examples of the organic substituents which may be present in addition to the OR groups are methyl, 2~ ethyl, propyl, butyl, 2,4,4-trimethylpentyl, octadecyl, phenyl, benzyl, tolyl, methoxy, ethoxy, butoxy, methoxy-ethoxy, phenoxy, benzyloxy, -(CH2)3~0CH2CH2)80C4Hg, ~ .
-CH2cH2cH2cH3 ~ - tCH2) 3CH2cH CH2 - (CH2) 3NH2, 2)31~ (C~2)2NH2, -CH2cH2cH(cH3)NH(cH2)2~H2 an~
(CH2)3N(CH3)2C18H37Cl. Preferably any substituents present in addition to the OR groups are selected from ~' 8~6 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 (II) hereinabove. Depending on the proportions and types of units present the siloxanes may have from less than 1.0 up to 3 total sub-stituents 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(0CH3)2SiOR
(CH3)3 (OC2H51 3SioR
Si(OR)4 C~H5Si(OR)3 CH2~CHSi(OC2H5)(0R)2 C8H17Si(OR)3 HSi(OR)3 Cl(CH2)3 ( )3 H2N(CH232NH(CH2)3S (CH3)(0 )2 Cl(cl8H37)N(cH2)3si(OR)3 (CH3)2 X

8~6 OR OR
CH3~2Si - Si(CH3?2 r CH31 r, 3 1 (- 313 - SiO- _ - SiO - Si(CH ) _ OR _ 20 - H _ 15 C6H5 OCH3 ~6H5 CH3 - Si OSi- - OSi - CH3 and OR CH OR

partial hydrolysates of alkoxy silanes, e.g. 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. stannous octoate.

~ ~, ~836 As the quaternary ammonium compound lngredient of the fabric conditioner compositions of this invention there may be employed any such compounds which are capable of imparting softness and/or lubricity to textile fabrics. Examples of the types of quaternary ammonium compounds which can be employed are the alkyldimethyl ammonium compounds represented by the formula Q2N(CH3)2 ~ X

amido alkoxylated ammonium compounds represented by the formula (CH2CH20) nH
[Q HNCH2CH2 - N - CH2CH2NH - Q] X and amido imidazolines represented by the formula Q - C ~ N

CH2 2NH& Q

in which general formulae, n is an integer, Q represents a fatty alkyl group, and X represents for example chlorine, bromine, iodine or the methylsulphate ICH3SO4) group, The preferred classes of quaternary ammonium compounds are the di(fattyalkyl) dimethyl ammonium compounds, (fattyalkyl)-dimethylaryl ammonium compounds and the (fattyalkyl) ~attyamido imidazolinium compounds particularly those wherein the fatty alkyl group has from 8 to 18 carbon 8~6 atoms. It is also preferred to employ the chloride, iodide or methylsulpha~e. Specific examples of such preferred compounds are di-tallow di-methyl ammonium chloride, di-tallow di-methyl ammonium iodide and 2-heptadecyl-l-methyl-l-(2'-stearoylamido-ethyl)-imidazolinium methyl sulphate.
The fabric conditioner compositions of this invention may be prepared by mixing the silicon compound and the quaternary ammonium compound. The proportion of silicon compound employed is not critical and will depend, for example, on the degree of fragrance desired and on the particular silicon compound(s) employed. Thus, a silane having four OR groups per molecule should be more effective than the same weight of a high molecular weight siloxane having four such OR groups per molecule. In general we prefer to employ the silicon compound in a proportion of fxom 0.01 to 20 per cent, more preferably 0.05 to 5 per cent, by weight, based on the total weight of the composition. More than one silicon compound may be incorporated into the fabric conditioner composition. For example, in order to achieve a particular fragrance se~eral silicon compounds containing different OR groups may be blended together. Alternatively, there may be employed a single silicon compound wherein the OR groups are derived from two or more different essential alcohols.
Also, if desired, the silicon compound~s) may be employed in conjunction with one or more of the essential alcohols per _ .

8~6 In addition to the silicon compound and quaternary ammonium compound the compositions of this invention may contain other ingredients which are normally found in fabric conditioners, for example diluents, such as isopropanol and water, and optical brighteners.
The compositions of this invention can be employed to treat fabrics (e.g. ~ool, cotton and synthetics~ in the same manner as for conventional fabric conditioner.
Usually such compositions are dispersed in the wash or rinse water to provide an add-on of about 0.01 to about 1% by weight based on the weight of the fabric. The compositions of this invention impart softness and/or lubricity to the treated fabric. They also impart a fragrance which is characteristic of the alcohol(s) from which the OR residues are derived and which is detectable for at least several days after treatment.
The following examples in which Me represents methyl, X represents -OCH2CH=C(CH3)(CH2)2CH-c(cH3)2 y ~ -O(CH2)2C~3CH(c~2)2cH C(CH3)2 Z " -O(CH2)2C6H5 illustrate the invention.
Example 1.
MeSi(OMe)3 (0.1 mole; 13.6g.) was refluxed with geraniol (0.2 mole; 30.8 g.) under a positive nitrogen pressure for 28 hours during which time methyl alcohol was removed by means of a Dean and 5tark apE-a~atus.
The resulting reaction mixture (Silane Al was analysed by gas-liquid chromatography and found to have the following composition by weight:
MeSi(:OMe)3/MeOH 2.4%
HOCH2CH=C(CH3)(CH2)2CH-C(CH3)2 14.2%
MeSi(OMe)2X 13.0~
MeSi(OMe)X2 48.6%
MeSiX3 21.9%
Using a similar procedure two more silane mixtures Silane B and Silane C were prepared by reacting MeSi(OMe)3 with respectively citronellol and 2-phenyl-ethyl alcohol. The silane mixtures had the following composition:
_ilane B
MeSi(OMe)3/MeOH 1.7%
HO(CH2)2(CH3)CH(CH2)2CH-(CH3)2 14.7%
MeSi(OMe)2Y 8.6%
MeSi(OMe)Y2 44.8~
MeSiY3 30.2%
Silane C
MeSi(OMe)3/MeOH 9.6%
HOZ 8.3%
~esi(oMe)2z 4.6%
Mesi(oMe)z2 43.6 MeZ2SiOSiZ2Me 33.9%

Silanes A, B and C were each mixed into different samples of an 8% by weight solution of a dimethyl di(fatty-alkyl) ammonium chloride in water the silanes being incorporated in proportion of 0.4% by weight based on the total weight of the composition. The compositions were then made up into 0.6% by weight solutions in warm (45 C) water. Pieces of Terry (cotton) cloth were treated by rinsing in the solutions and the pieces hung up to dry at normal atmospheric temperatures. For control purposes cloth samples were treated with similar solutions except that they were prepared from mixtures containing 0.2~ by weight of the essential alcohol in place of the silane.
After l hour each of the cloth samples carried a strong fragrance characteristic of the alcohol or respectively the alcohol used to prepare the silane.
After 24 hours the cloths obtained using the silicon compounds carried a much stronger fragrance than those obtained using the alcohols. The fragrance present on the silane-treated samples was quite strong after four days whereas the alcohol treated cloths were indistinguish-able in odour from an untreated cloth.
Example 2.
Geraniol (36 g.) was mixed with a poly(methyl-hydrogen)siloxane of average composition Me3SirOSiHMe~250SiMe3 30 g.) and anhydrous potassium carbonate (0.1 g.) The mixture was heated at 80 - 95C for 16 hours during which hydrogen was evolved. Filtration of the reaction mixture yielded a water white viscous polymer having the average composition Me3Si rOSiMeH]5 1OSiMeX]200SiMe3 The siloxane was mixed with the quaternary ammonium isopropanol solution described in Example 1 in a proportion of 0.4~ by weight. The resulting product (0.6~) was dissolved in water (99.4%) and the aqeous solution employed to treat Terry cloth as described in Example 1.
After 24 hours the siloxane-treated cloths carried a geraniol fragrance which was much stronger than that of a control sample prepared using the unmodified parent alcohol. This fragrance persisted for at least four days whereas the control sample was odourless after that time.
Example 3.
Example 2 was repeated employing cinnamic alcohol 2Q in place of the geraniol. In this case the cinnamic odour of the siloxane-treated cloth was weaker after 24 hours than that of the control cloth. After 4 days, however, the strength of fragrance on the siloxane-treated cloth had increased significantly.
Example 4.
Water (2.2 g.) was added with stirring to MeSi~OMe33 (27.2 g.). The mixture was heat~d to reflux .~

(72C) and methanol collected by a Dean and Stark apparatus. Geraniol (24.3 g.) was then added to the partial hydrolysis product thus obtained and the mixture heated for 15 hours at 90C. The methanol generated was removed via the Dean and Stark apparatus to yield a pale yellow, siloxane polymer having CH3,-OCH3 and X groups bonded to the silicon atoms.
The siloxane polymer was evaluated as a fabric conditioner ingredient by the technique described in Example 1. After 24 hours the geraniol fragrance was just perceptible but the strength of the odour had increased significantly after 4 days. The control sample prepared using the alcohol itself was odourless after this time.
Similar results were obtained when phenyl trimethoxysilane was reacted with geraniol and the resulting silane mix~ure evaluated as described above.

_ 14 -.~

Claims (4)

The embodiment of the invention in which an exclusive property or privilege is claimed are defined as follows :
1. A fabric conditioner composition comprising a fatty alkyl quaternary ammonium compound and as a fragrance-imparting component at least one silicon compound having in the molecule 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, any other substituents attached to silicon being selected from hydrogen atoms and organic groups free of sulphur and phosphorus, said organic groups being joined to silicon through a silicon to carbon or silicon-oxygen-carbon linkage.
2. A composition as claimed in Claim 1 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, -CH2PhOCH3, in which Ph represents phenylene, and -CH2CH=CH C6H5.
3. A composition as claimed in Claim 1 wherein the silicon compound is present in a proportion of from 0.05 to 5 per cent by weight based on the total weight of the composition.
4. A composition as claimed in Claim 1 wherein the quaternary ammonium compound is a di(fattyalkyl)dimethyl ammonium compound, a (fattyalkyl)dimethyl aryl ammonium compound or a fatty alkyl fattyamido imidazolinium compound.
CA313,503A 1977-10-15 1978-10-16 Compositions containing silicon compounds Expired CA1110806A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB4297177 1977-10-15
GB42971/77 1977-10-15

Publications (1)

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CA1110806A true CA1110806A (en) 1981-10-20

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CA313,503A Expired CA1110806A (en) 1977-10-15 1978-10-16 Compositions containing silicon compounds

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JP (2) JPS5493006A (en)
BE (2) BE871243A (en)
CA (1) CA1110806A (en)
DE (2) DE2844788C2 (en)
FR (2) FR2405992A1 (en)
GB (2) GB2007703B (en)
IT (2) IT1100671B (en)
NL (2) NL7810309A (en)
SE (1) SE426249B (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8680040B2 (en) 2006-12-20 2014-03-25 Henkel Ag & Co. Kgaa 1-aza-3,7-dioxabicyclo[3,3,0]octane compounds and monocyclic oxazolidines as pro-fragrances
CN106366109A (en) * 2016-08-08 2017-02-01 南雄鼎成新材料科技有限公司 Preparation method for aroma-releasing long-acting physical antibacterial agent

Families Citing this family (32)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IT1209302B (en) * 1979-02-01 1989-07-16 Dow Corning Ltd SOAP-BASING COMPOSITION CONTAINING SILICON COMPOUNDS SUCH AS LONG-LAST PERFUMED INGREDIENTS
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BE871243A (en) 1979-04-13
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JPS5493006A (en) 1979-07-23
GB2011967B (en) 1982-02-17
IT7828661A0 (en) 1978-10-11
DE2844788A1 (en) 1979-04-26
FR2406020B1 (en) 1981-11-06
FR2405992A1 (en) 1979-05-11
JPS5643280B2 (en) 1981-10-12
NL7810309A (en) 1979-04-18
FR2405992B1 (en) 1980-10-31
DE2844789A1 (en) 1979-04-26
SE426249B (en) 1982-12-20
JPS5459498A (en) 1979-05-14
IT1100671B (en) 1985-09-28
GB2007703A (en) 1979-05-23
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DE2844788C2 (en) 1987-04-16
IT7828683A0 (en) 1978-10-12
BE871242A (en) 1979-04-13
FR2406020A1 (en) 1979-05-11
GB2011967A (en) 1979-07-18

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