US3298775A - Process for bleaching textile fibres and new bleaching compositions - Google Patents
Process for bleaching textile fibres and new bleaching compositions Download PDFInfo
- Publication number
- US3298775A US3298775A US269765A US26976563A US3298775A US 3298775 A US3298775 A US 3298775A US 269765 A US269765 A US 269765A US 26976563 A US26976563 A US 26976563A US 3298775 A US3298775 A US 3298775A
- Authority
- US
- United States
- Prior art keywords
- bleaching
- anhydride
- active oxygen
- anhydrides
- source
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 238000004061 bleaching Methods 0.000 title claims description 41
- 239000000203 mixture Substances 0.000 title claims description 25
- 238000000034 method Methods 0.000 title claims description 13
- 239000004753 textile Substances 0.000 title claims description 12
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 29
- 239000001301 oxygen Substances 0.000 claims description 29
- 229910052760 oxygen Inorganic materials 0.000 claims description 29
- LGRFSURHDFAFJT-UHFFFAOYSA-N phthalic anhydride Chemical compound C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 claims description 13
- 150000001875 compounds Chemical class 0.000 claims description 12
- 239000000835 fiber Substances 0.000 claims description 9
- 238000007654 immersion Methods 0.000 claims description 3
- YZCKVEUIGOORGS-UHFFFAOYSA-N Hydrogen atom Chemical compound [H] YZCKVEUIGOORGS-UHFFFAOYSA-N 0.000 claims 2
- 150000008064 anhydrides Chemical class 0.000 description 34
- 239000007787 solid Substances 0.000 description 11
- ROFZMKDROVBLNY-UHFFFAOYSA-N 4-nitro-2-benzofuran-1,3-dione Chemical class [O-][N+](=O)C1=CC=CC2=C1C(=O)OC2=O ROFZMKDROVBLNY-UHFFFAOYSA-N 0.000 description 9
- 239000000243 solution Substances 0.000 description 8
- 238000012360 testing method Methods 0.000 description 7
- -1 benzoic Chemical class 0.000 description 5
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 5
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 230000003287 optical effect Effects 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000011707 mineral Substances 0.000 description 3
- 235000010755 mineral Nutrition 0.000 description 3
- 150000002978 peroxides Chemical class 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 229960001922 sodium perborate Drugs 0.000 description 3
- YKLJGMBLPUQQOI-UHFFFAOYSA-M sodium;oxidooxy(oxo)borane Chemical compound [Na+].[O-]OB=O YKLJGMBLPUQQOI-UHFFFAOYSA-M 0.000 description 3
- PGYZAKRTYUHXRA-UHFFFAOYSA-N 2,10-dinitro-12h-[1,4]benzothiazino[3,2-b]phenothiazin-3-one Chemical compound S1C2=CC(=O)C([N+]([O-])=O)=CC2=NC2=C1C=C1SC3=CC=C([N+](=O)[O-])C=C3NC1=C2 PGYZAKRTYUHXRA-UHFFFAOYSA-N 0.000 description 2
- BTTRMCQEPDPCPA-UHFFFAOYSA-N 4-chlorophthalic anhydride Chemical compound ClC1=CC=C2C(=O)OC(=O)C2=C1 BTTRMCQEPDPCPA-UHFFFAOYSA-N 0.000 description 2
- MMVIDXVHQANYAE-UHFFFAOYSA-N 5-nitro-2-benzofuran-1,3-dione Chemical class [O-][N+](=O)C1=CC=C2C(=O)OC(=O)C2=C1 MMVIDXVHQANYAE-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- 241001274216 Naso Species 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000012736 aqueous medium Substances 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 229910021538 borax Inorganic materials 0.000 description 2
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 description 2
- 239000002609 medium Substances 0.000 description 2
- 150000004967 organic peroxy acids Chemical class 0.000 description 2
- 238000005502 peroxidation Methods 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- 235000010339 sodium tetraborate Nutrition 0.000 description 2
- MWNQXXOSWHCCOZ-UHFFFAOYSA-L sodium;oxido carbonate Chemical compound [Na+].[O-]OC([O-])=O MWNQXXOSWHCCOZ-UHFFFAOYSA-L 0.000 description 2
- BSVBQGMMJUBVOD-UHFFFAOYSA-N trisodium borate Chemical compound [Na+].[Na+].[Na+].[O-]B([O-])[O-] BSVBQGMMJUBVOD-UHFFFAOYSA-N 0.000 description 2
- KFIRODWJCYBBHY-UHFFFAOYSA-N 3-nitrophthalic acid Chemical class OC(=O)C1=CC=CC([N+]([O-])=O)=C1C(O)=O KFIRODWJCYBBHY-UHFFFAOYSA-N 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical class CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000004755 animal textile Substances 0.000 description 1
- 239000006172 buffering agent Substances 0.000 description 1
- 230000003139 buffering effect Effects 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 238000004737 colorimetric analysis Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- VTIIJXUACCWYHX-UHFFFAOYSA-L disodium;carboxylatooxy carbonate Chemical compound [Na+].[Na+].[O-]C(=O)OOC([O-])=O VTIIJXUACCWYHX-UHFFFAOYSA-L 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000012770 industrial material Substances 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical class O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000006396 nitration reaction Methods 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 150000004965 peroxy acids Chemical class 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229940045872 sodium percarbonate Drugs 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- RVEZZJVBDQCTEF-UHFFFAOYSA-N sulfenic acid Chemical compound SO RVEZZJVBDQCTEF-UHFFFAOYSA-N 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000004758 synthetic textile Substances 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- D06L4/10—Bleaching fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods; Bleaching leather or furs using agents which develop oxygen
- D06L4/12—Bleaching fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods; Bleaching leather or furs using agents which develop oxygen combined with specific additives
Definitions
- the present invention relates to new bleaching compo- United States Patent sitions "for textile fibres' and more particularly to solid and stable compositions Which, in aqueous solution, give oxidising agents having high activity and which are effective at only slightly raised temperatures.
- organic peracids and their salts have the properties of bleaching vegetable, animal or synthetic textile fibres, but the use thereof in practice is made diflicult. because such materials cannot be satisfactorily and sometimes because of their liquid condition.
- the anhydrides employed in these known processes are simple unsubstituted anhydrides, such as benzoic, phthalic, succinic, maleic, glutaric, acetic, propionic and like anhydrides.
- the use thereof presents various disadvantages, however, particularly when they must be employed for bleaching operations at normal temperatures and at pH values below 10.
- the anhydrides of lower monoacids such as acetic, propionic and butyric acids are liquid at normal temperatures andthus are not suitable for the preparation of solid bleaching compounds ready for use.
- solid anhydrides certain of them, such as the benzoic and phthalic anhydrides, have very low solubility in aqueous media and this limits the peroxidation reaction and gives a heterogeneous character to the bleaching.
- Certain dicarboxylic acid anhydrides have the serious disadvantage of having little reactivity in weakly alkaline medium at the relatively low temperature of 50 to 80 C.; this is the case with tetrahydrophthalic and maleic anhydrides, which only form a small amount of organic per compounds in aqueous medium. In the case of numerous solid anhydrides, the oxygen of the initial per compound is thus not satisfactorily utilized.
- the anhydrides of organic diacids ofiering particular interest are the nitrophthalic anhydrides, preferably 3- nitrophthalic anhydride, and the halophthalic anhydrides, such as 4-chlorophthalic anhydride.
- the substituted anhydrides react with the hydrogen peroxide, even in weakly alkaline medium, in order to form corresponding peracids much more completely than the unsubstituted phthalic anhydride.
- a solid source of active oxygen such as: monohydrated or tetrahydrated perborate, percarbonate, perpyrophosphate, urea peroxyhydrate and in general the mineral or organic peroxyhydrates, as well as the mineral or organic peroxides.
- the active oxygen concentration of the bleaching bath is preferably between 20 and 500 mg. of active oxygen per litre.
- the material to be bleached is treated with a solution adjusted to a pH value between 7 and 11. There are used, per molecule of peroxide, 0.4 to 2 molecules of carboxylic acid anhydride substituted by at least one electrophilic group, preferably 0.8 to 1.5 molecules.
- the bleaching can be carried out at slightly elevated temperatures, for example, in the range from 30 to C. and preferably at about 60 C.
- a sulphur black solution with an optical density equal to 0.6 green filter, thickness 10 mm.
- this solution is buffered to an alkaline pH value by a mixture of sodium carbonate and bicarbonate, or by any other buffering system such as those formed from sodium borate.
- This solution is brought to 60 C. and the per compound and the anhydride are added, separately or mixed before use, and the bleaching bath is kept at 60 C. for 20 minutes.
- the sample is then quickly cooled to normal temperature and its optical density is measured by colorimetry. The result is expressed as a percentage of decoloration, related to a comparison sample not provided with active oxygen and placed under the same operational conditions.
- Example 1 Under the conditions described above, the operation takes place in the absence of organic anhydrides, using sodium borate in its monohydrated form NaBO .H O or tetrahydrated form NaBO .4H O. An average degree of decoloration of 5% is obtained. When the temperature is brought to 92 C., always under the same general conditions, the average degree of decoloration is 40%.
- Example 2 Under the test conditions previously described and at a temperature of 60 C., the action of the unsubstituted anhydrides and that of the substituted dicarboxylic anhydrides are compared, the active oxygen being supplied by monohydrated sodium perborate.
- Example 3 Under the same conditions as in Example 2, a mixture of 3-nitrophthalic and 4-nitrophthalic anhydrides is used, obtained by the mixture of acids resulting from 'a phthalic anhydride nitration by means of :a sulphonitric mixture being transformed into anhydride. For a molar ratio of 1 between the anhydride and the active oxygen, a degree of decoloration of 45% is obtained. For a molar ratio of 1.3, a degree of decoloration of 68% is obtained.
- Example 4 Always under the same conditions, the degree of decoloration obtained is compared, the source of active oxygen being on the one hand monohydrated sodium perborate with 15.7% of active oxygen and on the other hand sodium percarbonate with 11.7% of active oxygen, the anhydride in both cases being a sample of 3-nitrophthalic anhydride (melting point 160-163 C.), the molar ratio between the anhydride and the active oxygen being equal to 1.3.
- a degree of decoloration of 49% is obtained with the perborate and of 53 with the percarbonate.
- a mixture formed of 3.4 parts of monohydrated sodium perborate NaBO .H O and 6.6 parts of nitrophthalic anhydride, having a decolouring power of 40%, measured by the test previously described, did not show either a lowering of its active oxygen content or a loss of decolouring power after having been stored for 2 months under normal conditions, i.e., in a standard package, and at ambient temperature.
- a process for bleaching textile fibers comprising immersion in a bleaching bath containing as a source of active oxygen a peroxygen compound and containing a source of active oxygen, comprising additionally adding to the bleaching bath a phthalic acid anhydride having in its molecule at least one hydrogen atom replaced by an electronegative group.
- a bleaching composition for textile fibers containing as a source of active oxygen a peroxygen compound and a phthalic acid anhydride having in its molecule at least one hydrogen atom replaced by an electronega-tive group.
- a method of bleaching comprising passing textile fibers through a bleaching solution comprising a mixture of a source of active oxygen selected from the group consisting of perborates, percarbonates, perpyrophosphates, peroxyhydrates and peroxides, and a phthalic anhydride acid wherein at least one hydrogen atom in the anhydride molecule is replaced by an electrophilic radical selected from the group consisting of N0 Cl, Br, H and NaSO 16.
Landscapes
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Detergent Compositions (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR894538A FR1328962A (fr) | 1962-04-14 | 1962-04-14 | Procédé de blanchiment de fibres textiles et nouvelles compositions utilisables dans ce procédé |
Publications (1)
Publication Number | Publication Date |
---|---|
US3298775A true US3298775A (en) | 1967-01-17 |
Family
ID=8776927
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US269765A Expired - Lifetime US3298775A (en) | 1962-04-14 | 1963-04-01 | Process for bleaching textile fibres and new bleaching compositions |
Country Status (5)
Country | Link |
---|---|
US (1) | US3298775A (en。) |
BE (1) | BE630532A (en。) |
DE (1) | DE1444001A1 (en。) |
FR (1) | FR1328962A (en。) |
GB (1) | GB968806A (en。) |
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3528115A (en) * | 1967-12-22 | 1970-09-15 | Du Pont | Bleaching fabrics with peracetic acid formed in situ thereon |
US4110074A (en) * | 1977-10-03 | 1978-08-29 | Fmc Corporation | Mixed carboxylic/sulfonic anhydrides in peroxygen bleaching |
US4111651A (en) * | 1977-10-03 | 1978-09-05 | Fmc Corporation | Sulfonic anhydrides in peroxygen bleaching |
US4202786A (en) * | 1978-12-22 | 1980-05-13 | Fmc Corporation | Peroxygen bleaching and compositions therefor |
US4207070A (en) * | 1978-10-10 | 1980-06-10 | Fmc Corporation | Peroxygen bleaching and compositions therefor |
US4212757A (en) * | 1978-12-22 | 1980-07-15 | Fmc Corporation | Peroxygen bleaching and compositions therefor |
-
0
- BE BE630532D patent/BE630532A/xx unknown
-
1962
- 1962-04-14 FR FR894538A patent/FR1328962A/fr not_active Expired
-
1963
- 1963-04-01 US US269765A patent/US3298775A/en not_active Expired - Lifetime
- 1963-04-04 DE DE19631444001 patent/DE1444001A1/de active Pending
- 1963-04-09 GB GB14208/63A patent/GB968806A/en not_active Expired
Non-Patent Citations (1)
Title |
---|
None * |
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3528115A (en) * | 1967-12-22 | 1970-09-15 | Du Pont | Bleaching fabrics with peracetic acid formed in situ thereon |
US4110074A (en) * | 1977-10-03 | 1978-08-29 | Fmc Corporation | Mixed carboxylic/sulfonic anhydrides in peroxygen bleaching |
US4111651A (en) * | 1977-10-03 | 1978-09-05 | Fmc Corporation | Sulfonic anhydrides in peroxygen bleaching |
US4207070A (en) * | 1978-10-10 | 1980-06-10 | Fmc Corporation | Peroxygen bleaching and compositions therefor |
US4202786A (en) * | 1978-12-22 | 1980-05-13 | Fmc Corporation | Peroxygen bleaching and compositions therefor |
US4212757A (en) * | 1978-12-22 | 1980-07-15 | Fmc Corporation | Peroxygen bleaching and compositions therefor |
Also Published As
Publication number | Publication date |
---|---|
DE1444001A1 (de) | 1969-04-30 |
BE630532A (en。) | |
FR1328962A (fr) | 1963-06-07 |
GB968806A (en) | 1964-09-02 |
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