Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
  • C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
  • C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
  • C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
  • C07D251/40—Nitrogen atoms
  • C07D251/54—Three nitrogen atoms
  • C07D251/68—Triazinylamino stilbenes
• • D—TEXTILES; PAPER
  • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
  • D06L—DRY-CLEANING, WASHING OR BLEACHING FIBRES, FILAMENTS, THREADS, YARNS, FABRICS, FEATHERS OR MADE-UP FIBROUS GOODS; BLEACHING LEATHER OR FURS
  • D06L4/00—Bleaching fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods; Bleaching leather or furs
  • D06L4/60—Optical bleaching or brightening

Definitions

• X and Y taken together may form a morpholino ring.
• These compounds maintain their brightening effect on fabrics which are treated with cationic softeners either after, or concurrently, with the application of the brightener agent.
• This invention relates to optical brightening agents and to compositions containing these new brightening agents.
• the new compounds of this invention are optical brighteners of the bis-triazinylarnino stilbene type. This class of compounds is finding rapidly increasing application in the textile, paper, detergent and other laundry product industries. The increased brightness which results from incorporating relatively minor amounts of such brighteners into paper, textiles, detergents and other 1aun-. dry products greatly enhances the appearance and consequently, the marketable value of the finished products.
• Optical brighteners improve the appearance of these products by neutralizing the familiar yellow tinge that is usually apparent in untreated products of the type mentioned. This yellow tinge is caused by the absorption of short wavelength light. Optical brighteners neutralize the yellow tinge resulting therefrom by absorbing invisible ultraviolet radiation and emitting the energy thereof in the form of visible blue to blue-violet light.
• the fluorescent properties of the optical brighteners of this invention are strikingly apparent under ultraviolet light in darkroom conditions.
• the housewife may launder her family clothes with a relatively expensive detergent in order to achieve a brighter wash by virtue of the optical brightener contained in the detergent, and then in finishing the wash by the routine use of a cationic fabric softener, almost completely destroy the bright-White affect of the brightener for which she paid a premium price in purchasing her detergent.
• optical brightening agents which I have discovered, besides being very useful for the usual applications of optical brighteners, surprisingly maintain their brightening affect on fabrics which are treated with cationic softeners either after, or concurrently, with the application of the brightener agent.
• a has a value of 1-3
• b has a value of 0-1
• 0 has a value of 0-1
• d has a value of O-l; or X and Y taken together may form a morpholino ring.
• alkaline salts of the compound of the above formula are also encompassed Within the scope of the invention.
• Typical basic cations forming such salts are alkaline and alkaline earth metal cations, and cations derived from ammonia and mono-, di-, and tri-alkanolamines.
• X and Y both are CHZCHQOH, and 1 has a value of 0.
• the preferred compound of this invention is: 4,4'-bis ⁇ [-anilino 6 [N-(3-aminopropyl) diethanolamino]-l,3,5 triazin 2 yl]-amino ⁇ stilbene-2,2'-disulfonic acid.
• the brightener compounds of this invention may be applied to substrates comprised of cellulose, polyamides, and proteinaceous fibers, and other substrates, from dilute aqueous solutions.
• the compounds of this invention are generally employed in their salt form, however, the acid form may be isolated if desired.
• the compounds which I have discovered are particularly advantageous not only because of the high degree of brightness which they impart to fabrics, but because the fabrics substantially maintain their bright appearance even after treatment with cationic fabric softeners.
• the brighteners currently on the market are masked or quenched when the fabrics containing them are subsequently or simultaneously treated with cationic softeners.
• the application of the brighteners of this invention to fabrics can be effected by conventional methods well known to the art.
• the fabric can be padded with the brightener during the manufacture at the mill, or in the more familar manner, the brightener may be incorporated into detergent compositions and thus be applied to the fabric during the laundry operation.
• the brighteners of this invention can be incorporated into cationic softener compositions and thus applied to the fabric at the same time the softener is applied.
• an aqueous solution of from about 0.05% to about 2% of brightener compound is employed.
• Typical cationic softeners on the market are dialkyl dimethyl ammonium chloride solutions in which the alkyl groups generally are 12-18 carbon atoms in length.
• the alkyl groups in some formulations may be ethoxylated.
• l-methyl-l-alkylamid-ethyl-2-alkyl imidazolinium methosulfate type soft'eners are representative of other cat onic softeners also available.
• Typical detergent formulations comprise:
• EXAMPLE 1 A slurry of 150 grams of 4,4-bis-[(6-anilino 4-chloro- 1,3,5-triazin-2-yl) amino]stilbene- 2,2-disulfonic acid in 1200 ml. of water was prepared. To this slurry 71 grams of N-(3-aminopropyl)-diethanolamine are added with stirring and the mixture heated to 90 C. The pH decreased to 9.5-10 and thereafter was maintained at 10.5- 11 by the addition of 16 grams of 50% sodium hydroxide. The reaction mixture was then cooled to room temperature. The mother liquor was decanted, and 1200 ml. of water and 300 grams sodium chloride added. The solids were ground in a wet slurry with 400 ml.
• EXAMPLE 3 276 grams of water and 300 grams of ice were placed in a flask and grams of cyanuric chloride and 66 grams of sulfanilic acid added. The mixture was stirred for 1 hour at 0 C. After 3 hours dropwise addition of 269 grams of 15% sodium carbonate was accomplished, bring ing the pH to 7. At the end of the addition, 1052 grams of 6.46% diaminostilbenedisulfonic acid/Na CO solution were added all at once. The mixture was heated to 70 C. and a pH 8-8.5 maintained. Thereafter the temperature was raised to -95 (3., and 400 ml. of hot water and grams sodium chloride added; followed by seeding. Then the mixture was air cooled to 45 C. and filtered.
• Example 4 The procedure of Example 1 is re eated but the N-(3- aminopropyl)-diethanolamine is replaced with N,N-dimethyl-1,3-propanediamine.
• the resultant product is 4,4- bis ⁇ [4-anilino-6-[N,N dimethyl 1,3 propanediamino]- 1,3,5-triazin-2-yl]-amino ⁇ -stilbene-2,2-disulfonic acid.
• EXAMPLE 5 The procedure of Example 1 is repeated but the N-(3- aminopropyl) diethanola-mine is replaced with 4 (3- aminopropyl)morpholine.- The resultant product is 4,4- bis ⁇ [4 anilino 6 [4 (3 aminopropyl)morpholino]- 1,3,5 triazin 2 yl] amino ⁇ stilbene 2,2 disulfonic acid.
• Example 6 The procedure of Example 1 is repeated but the N-(3- aminopropyl) diethanolarnine is replaced with (3.3- diamino N methyldipropylamine). The resultant product is 4,4 bis ⁇ [4 anilino 6 [(3,3' diamino N- methyldipropylamino)] 1,3,5 triazin 2 yl] amino ⁇ - stilbene-2,2'-disulfonic acid.
• EXAMPLE 7 Softener formulations were made up using the brighteners of Examples 1, 4, 5, and 6. Each formulation was comprised of: 5 ml. triethanolamine, 10 ml. methyl Cellosolve, 31 ml. water, 4 gms. distearyl-dimethyl ammonium chloride, 160 mg. of a brightener compound of this invention. The pH of each formulation was adjusted to 5 with acetic acid.
• EXAMPLE 8 Additional batches of softener formulations were made with the brightener compounds of Examples 1, 4, 5, and 6 in the same manner as Example 7; the pH was again adjusted to 5, this time with formic acid.

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• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Engineering & Computer Science (AREA)
• Textile Engineering (AREA)
• Detergent Compositions (AREA)
• Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)

Applications Claiming Priority (1)

Publications (1)

Family

ID=24241500

Family Applications (1)

Country Status (5)

Cited By (4)

Families Citing this family (1)

Citations (1)

• 1966
  • 1966-06-29 US US561330A patent/US3546218A/en not_active Expired - Lifetime
• 1967
  • 1967-06-26 CH CH904767A patent/CH474601A/de not_active IP Right Cessation
  • 1967-06-28 FR FR112290A patent/FR1529366A/fr not_active Expired
  • 1967-06-28 GB GB29800/67A patent/GB1129548A/en not_active Expired
• 1968
  • 1968-06-18 BE BE716764D patent/BE716764A/xx unknown

Patent Citations (1)

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