Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
  • C07D249/16—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms condensed with carbocyclic rings or ring systems
  • C07D249/22—Naphthotriazoles
  • C07D249/24—Naphthotriazoles with stilbene radicals directly attached in position 2
• • 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
  • C11D3/40—Dyes ; Pigments
  • C11D3/42—Brightening agents ; Blueing agents

Definitions

• the present invention concerns washing agents, which contain, in addition to detergent (wash-active) substances, at least one optical brightener of the formula defined below, as well as to washing liquors prepared therewith; the invention further relates to a method for the optical brightening, i.e. for the improvement of the degree of whiteness, of polymeric esters of aromatic dicarboxylic acids with polyvalent alcohols, particularly of polyethyleneglycol terephthalate fibers, with the aid of such washing agents and liquors.
• optical brighteners are incorporated into almost all white textiles before use to increase their degree of whiteness.
• fibers brightened in this way do not retain the improved degree of whiteness for as long as desired because optical brighteners turn yellow or grey in time due to deterioration under the eifect of light, moisture and/or atmospheric oxygen.
• optical brighteners are added to the washing agents used for the care thereof. Since, in the household and commercial laundering there are usually present fibers of many kinds and origin, the washing agents must contain brighteners which produce good white effects on as many types of fiber as possible under the washing conditions conventional in households and laundries.
• polyester fiber material is usually pad-dyed with dispersions or solutions of 'ice brightener and then given a heat treatment at l-220 C.
• Use can be made of a purely aqueous type of treatment, i.e. with aqueous liquors which, in addition to optical ibrighteners having afiinity to the fiber, also contain dispersing agents, e.g. polyglycol ether of higher alkanols or alkyl phenols, and carriers, e.g. phenyl phenols or polychlorobenzene compounds.
• dispersing agents e.g. polyglycol ether of higher alkanols or alkyl phenols
• carriers e.g. phenyl phenols or polychlorobenzene compounds.
• many brighteners suitable for terephthalic acid polyester fibers have injurious effects on other types of fibers which may be present in the Wash.
• optical brighteners having aflinity to polyester from the class of 7-triazinylamino-3-phenyl coumarins, 7-naphthotriaZolyl-(2)-3-phenyl coumarins or his [alkylbenzoxazolyl (2)]-thiophenes on repeated washing produce undesirable green shadings or even green colourings on synthetic polyamide fibers and such optical brighteners from the class of Z-styryl-benzoxazoles produce such undesirable shadings or colourings even on cotton which is washed at the same time. This does not recommend their use in household or commercial laundering agents or liquors.
• polyester brightener for practical use in washing liquors, should cause no shading or discoloration effects on other types of fiber.
• R represents hydrogen, an alkyl group having 1 to 4 carbon atoms or an alkoxyalkyl or hydroxyalkyl group having 2 to 5 carbon atoms or an alkoxyalkoxyalkyl group having 5 to 8 carbon atoms,
• R represents hydrogen or an alkyl group having 1 to 4 carbon atoms
• R and R together with the nitrogen atom linking them may also represent a saturated 6-membered ring optionally containing further hetero atoms.
• Alkyl groups symbolised by R and R preferably have straight chains; however, they can also be branched, containing secondary carbon atoms.
• Alkoxyalkyl groups represented by R are especially the ,B-methoxy-ethyl, S-ethoxyethyl, ,B-propoxyethyl, por -methoxypropyl and ,6- or 'y-ethoxypropyl groups.
• Hydroxyalkyl groups represented by R are, for instance, the ⁇ 3 hydroxyethyl, 'y hydroxypropyl and a-hydroxybutyl groups.
• Alkoxyalkoxyalkyl groups represented by R preferably have 2 to 3 carbon atoms per 'alkoxy or alkyl group.
• R represents hydrogen, the methyl or ethyl group and R represents the methyl or ethyl group.
• Washing agents according to the invention contain, as detergents, e.g. surface active ionogenic substances such as soaps, in particular, alkali metal salts of higher fatty acids, soluble salts of higher fatty alcohol sulfates, of higher and/ or polyalkyl substituted arylsulfonic acids, of sulfocarboxylic acid esters of medium to higher alcohols, and of higher alkanoylamino-alkyl or -aryl-carboxylic r -sulfonic acids or salts of fatty acid glycerol-sulfates, or surface active non-ionogenic substances, e.g. fatty alcohol or higher alkylphenol polyglycol ethers.
• surface active ionogenic substances such as soaps, in particular, alkali metal salts of higher fatty acids, soluble salts of higher fatty alcohol sulfates, of higher and/ or polyalkyl substituted arylsulfonic acids, of sulfocar
• the washing agent can contain the usual fillers and auxiliaries, e.g. neutral salts such as sodium sulfate; alkaline earth metal-binding substances such as alkali polyand polymetaphosphates; alkali metal silicates; metal-binding substances, e.g. complexons such as soluble salts of ethylenediamine-tetra-acetic acid; foam stabilisers such as alkanolamides of higher fatty acids; antistatics; plasticisers; fatty skin protectives such as lanolin; dirt carriers in the liquor such as carboxymethylcellulose or melamine; dyestuffs; perfume and also bleaching agents such as alkali metal salts of perboric acid.
• neutral salts such as sodium sulfate
• alkaline earth metal-binding substances such as alkali polyand polymetaphosphates
• alkali metal silicates alkali metal silicates
• metal-binding substances e.g. complexons such as soluble salts of ethylened
• the content of brightener of Formula I in the washing liquor is preferably 0.0002 to 0.05% by weight calculated on the material to be brightened, or 0.0004 to 0.04 g. of brightener per liter washing liquor.
• Other preferred washing conditions are treatment times of 5-30 minutes, temperatures of 50 95 C., and circulation of the washing liquor.
• the optical brighteners of Formula I are incorporated in suitable amounts into the usual household and laundry washing agents.
• the present application provides washing agents which are characterised by a content of 0.02 to 0.5%, preferably of 0.05 to 0.1%, of an optical brightener of the Formula I, calculated on the total weight of the agent.
• the optical brighteners of Formula I are incorporated into the washing agents by known methods, either by mixing the dry ingredients or milling the various components, or by mixing the optical brightener with a moist paste of the washing agent and subsequently drying and crushing, e.g. pulverising, or by spraying a solution of brightener in a volatile solvent onto the washing agent and then removing the solvent.
• the finely distributed optical brightener can also be added directly to an otherwise ready-for-use washing liquor, advantageously by mixing the latter with a solution of the brightener in a water soluble organic solvent.
• Fiber material having a content of polyethyleneglycol terephthalate fibers washed repeatedly over long periods of use with washing agents according to the invention or in washing liquors according to the invention has a pleasant, white appearance.
• EXAMPLE 1 5 g. of a fabric made from polyglycol terephthalate staple fibres, e.g. from Dacron, are introduced into 100 ml. of a 92 hot washing liquor which contains 0.4 g. of a washing agent consisting of:
• the fabric is rinsed, first with lukewarm and then with cold water.
• the washing process described above is performed 10 times with the same fabric but with a new washing liquor each time.
• a polyester fabric having a beautiful white effect in daylight is obtained. If the white effect of the fabric obtained after washing 10 times is measured with a fiuorometer produced by Messr. Schildknecht, Ziirich, Switzerland, then a fluorescence value of 44 is determined. If the fabric so washed is compared with the white scale described in SVF (Schweizerische vertex von Fabereifachleute) 19 (1964), No. 6, p. 480, then its degree of whiteness is 160.
• the 5 g. of polyglycol terephthalate fabric are replaced by 5 g. of a synthetic polyamide fabric, e.g. nylon, or by 5 g. of a cellulose diacetate fabric and the procedure given above is followed, then a very beautiful white shading is also obtained on these fabrics.
• the polyamide fabric so treated has a fluorescence value of and a degree of whiteness of 200 and the cellulose diacetate fabric has a fluorescence value of 55 and a degree of whiteness of 140.
• the white effect on cotton is slighter but clearly discernable. There is no tendency towards green shading.
• polyglycol terephthalate fabric has a degree of whiteness of 150, 160, and 160 respectively, whilst nylon fabric has a degree of whiteness of 205, 190, and 180 respectively. No green shading can be determined on cotton.
• Example 2 5 g. of a fabric made from polyglycol terephthalate staple fibres, e.g. Dacron, are introduced into 100 ml. of a washing liquor at 92 which contains 0.5 g. of a washing agent consisting of:
• the fabric is washed, with light mechanical circulation, in this liquor for 12 minutes at 92. After this washing,
• the fabric is rinsed first with lukewarm and then with cold Water.
• the washing process described above is performed 10 times in all with a new washing liquor each time.
• a polyglycol terephthalate fabric having a beautiful white effect in daylight is obtained.
• the polyglycol terephthalate staple fibre fabric is replaced by the same amount of a synthetic polyamide fabric, e.g. nylon or Perlon, or cellulose diacetate fabric, then with otherwise the same procedure as given, these substrata are also brightened. .
• the brightening effect obtained on cotton fabric is slight but clearly discernable. There is no tendency to green shading.
• Example 3 0.0002 g. of the optical brightener 2-(stilbyl-4")-(naphtho-1,2':4,5)-1,2,3-triazole-2"-sulphonic acid monoethylamide are dissolved in 0.2 g. of ethylene glycol monoethyl ether and the solution is added to 100 ml. of a washing liquor containing 0.6 g. of a washing agent consisting of: 1
• g. of a polyglycol terephthalate staple fibre fabric e.g. Dacron
• a polyglycol terephthalate staple fibre fabric e.g. Dacron
• the fabric is rinsed, first with lukewarm and then with cold water. This washing process is performed, in all, 10 times.
• the fabric so treated has a beautiful white effect in daylight.
• the polyglycol terephthalate staple fibre fabric is replaced by an equal amount of a synthetic polyamide fabric, e.g.- nylon or Perlon, or by cellulose diacetate fabric, these substrata are also brightened. :If the polyglycol terephthalate staple fibres are replaced by an equal amount of cotton fabric then the brightening effect obtained is slight but clearly discernable. No green shading of the cotton fabric canbe determined.
• a synthetic polyamide fabric e.g.- nylon or Perlon
• Example 4 At a temperature of 70, 5 g. of a polyglycol terephthalate staple fibre, e.g. Dacron, are introduced into 100 ml. of a washing liquor which contains 0.5 g. of a washing agent consisting of:
• Example 5 5 g. of a fabric made from polyethyleneglycol terephthalate fibers (e.g. Dacron) are treated by the same procedure as in Example 1, but using in lieu of the 0.4 g. of washing agent employed therein, (a) 0.5 g.
• a fabric made from polyethyleneglycol terephthalate fibers e.g. Dacron
• washing agent consisting of 16 parts of sodium dodecylbenzene sulfonate 4 parts of sodium lauryl sulfate 35 parts of pentasodium tripolyphosphate 7 parts of tetrasodium pyrophosphate 7 parts of sodium disilicate [Na (SiO 2 parts of magnesium metasilicate 1 part of carboxymethylcellulose 0.5 part of sodium ethylenediamine-tetra-acetate 25 parts of sodium sulfate 2.5 parts of water in combination with the same amount of the same optical brightener as in the said Example 1.
• the fluorescence value of the laundered fabric determined in the same manner as in Example 1, but with a Harrison fluorometer, is 64.
• Example 6 Example 3 is repeated, but there are used in the washing liquor in lieu of 0.6 g. of the washing agent employed in Example 3, 0.5 g. of a washing agent consisting of 40 parts of soap (mixture of sodium salt of coconut oil fatty acid and sodium stearate in a weight ratio of about 1:2)
• Example 19 1000 g. of usual household laundry, consisting of polyglycol terephthalate fibre fabrics, synthetic polyamide fibre fabrics and cotton fabrics or mixed fabrics containing these fibres are introduced into 20 litres of an 85-90 hot washing liquor which contains 80 g. of a washing agent, consisting of 25 parts of sodium dodecylbenzene sulphonate,
• the washing procedure described above is performed, in all, times with a new washing liquor each time. Fabrics are obtained which have a beautiful white effect in daylight, regardless of which type of fibers they are made of.
• the reaction mixture is then slowly heated to 1l5l20 while introducing further monomethylamine and it is stirred at this temperature for 6 hours. After cooling, the crystal mass is filtered off, washed first with water, then well with alcohol, dried and then recrystallised from boiling chlorobenzene.
• the 2 (stilbyl 4") (naphtho- 1,2'24,5)-1,2,3-triazole2"-sulphonic acid monomethylamide is obtained as a yellowish powder which melts at 222223.
• a process for improving the degree of whiteness of polyglycolterephthalate fibers comprising treating the said fibers with an aqueous washing liquor which contains a washing agent composition consisting essentially of (a) from about 0.02 to 0.5%, calculated on the total weight of said agent, of a compound of the formula R1 S O z N 9 wherein R represents hydrogen, an alkyl group having 1 to 4 carbon atoms, or an alkoxyalkyl or hydroxyalkyl group having 2 to 5 carbon atoms, or an alkoxyalkoxyalkyl group having 5 to 8 carbon atoms, and R represents hydrogen or an alkyl group having 1 to 4 carbon atoms, and R and R together with the nitrogen atom linking them may also represent a saturated sixmembered ring which optionally contains further hetero atoms, and (b) a surface active anionic substance, or a surface active nonionic substance in sufiicient amount to simultaneously wash and optically brighten said fiber.
• a washing agent composition consisting essentially of (a)
• a process for improving the degree of whiteness of a material made from polyglycolterephthalate fibers in a load of laundry containing the same as well as materials made from one or several kinds of fibers selected from polyamide, cellulose diacetate and cotton fibers comprising treating said laundry with an aqueous washing liquor which contains a washing agent composition as defined in claim 1, in suflicient amount to simultaneously wash and optically brighten at least said polyglycol material without deteriorating ton material present.

Landscapes

• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Life Sciences & Earth Sciences (AREA)
• Engineering & Computer Science (AREA)
• Chemical Kinetics & Catalysis (AREA)
• Oil, Petroleum & Natural Gas (AREA)
• Wood Science & Technology (AREA)
• Detergent Compositions (AREA)
• Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)

Applications Claiming Priority (1)

Publications (1)

Family

ID=4248015

Family Applications (1)

Country Status (6)

Cited By (1)

• 1966
  • 1966-03-04 CH CH307366A patent/CH464419A/de unknown
• 1967
  • 1967-03-03 FR FR97379A patent/FR1513043A/fr not_active Expired
  • 1967-03-03 BE BE695010D patent/BE695010A/xx unknown
  • 1967-03-03 DE DE19671617104 patent/DE1617104A1/de active Pending
  • 1967-03-03 GB GB10197/67A patent/GB1107696A/en not_active Expired
  • 1967-11-20 US US684481A patent/US3583925A/en not_active Expired - Lifetime

Also Published As

Similar Documents