CH650489A5 - Ligninaddukt und verfahren zu dessen herstellung. - Google Patents
Ligninaddukt und verfahren zu dessen herstellung. Download PDFInfo
- Publication number
- CH650489A5 CH650489A5 CH1162/81A CH116281A CH650489A5 CH 650489 A5 CH650489 A5 CH 650489A5 CH 1162/81 A CH1162/81 A CH 1162/81A CH 116281 A CH116281 A CH 116281A CH 650489 A5 CH650489 A5 CH 650489A5
- Authority
- CH
- Switzerland
- Prior art keywords
- lignin
- adduct
- dye
- benzyl alcohol
- broth
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 36
- 238000004519 manufacturing process Methods 0.000 title description 6
- WVDDGKGOMKODPV-UHFFFAOYSA-N benzyl alcohol Substances OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 claims description 87
- 239000000975 dye Substances 0.000 claims description 76
- 229920005610 lignin Polymers 0.000 claims description 73
- 229920001732 Lignosulfonate Polymers 0.000 claims description 54
- -1 hydroxyl-benzyl Chemical group 0.000 claims description 48
- 235000019445 benzyl alcohol Nutrition 0.000 claims description 34
- 239000000463 material Substances 0.000 claims description 31
- 239000000203 mixture Substances 0.000 claims description 27
- 235000019357 lignosulphonate Nutrition 0.000 claims description 22
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 21
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 claims description 20
- 238000006243 chemical reaction Methods 0.000 claims description 17
- 150000001875 compounds Chemical class 0.000 claims description 15
- 239000000987 azo dye Substances 0.000 claims description 12
- 230000008569 process Effects 0.000 claims description 12
- 239000011541 reaction mixture Substances 0.000 claims description 8
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 239000011593 sulfur Substances 0.000 claims description 6
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 5
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 230000000694 effects Effects 0.000 claims description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000001741 organic sulfur group Chemical group 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 239000002270 dispersing agent Substances 0.000 description 75
- 239000000047 product Substances 0.000 description 44
- 239000007787 solid Substances 0.000 description 26
- 235000010633 broth Nutrition 0.000 description 24
- 238000001914 filtration Methods 0.000 description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- 238000006722 reduction reaction Methods 0.000 description 15
- 230000009467 reduction Effects 0.000 description 14
- 238000004040 coloring Methods 0.000 description 11
- 238000000227 grinding Methods 0.000 description 11
- 238000003801 milling Methods 0.000 description 11
- 239000000123 paper Substances 0.000 description 11
- 239000000243 solution Substances 0.000 description 10
- 229920000742 Cotton Polymers 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- 239000004744 fabric Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000006260 foam Substances 0.000 description 6
- 238000005187 foaming Methods 0.000 description 6
- 235000000346 sugar Nutrition 0.000 description 6
- 239000008399 tap water Substances 0.000 description 6
- 235000020679 tap water Nutrition 0.000 description 6
- 239000006185 dispersion Substances 0.000 description 5
- 239000012153 distilled water Substances 0.000 description 5
- 239000002245 particle Substances 0.000 description 5
- COCWIIAFGQLMGS-UHFFFAOYSA-N 3-[n-ethyl-3-methyl-4-[(5-nitro-1,3-thiazol-2-yl)diazenyl]anilino]propane-1,2-diol Chemical compound CC1=CC(N(CC(O)CO)CC)=CC=C1N=NC1=NC=C([N+]([O-])=O)S1 COCWIIAFGQLMGS-UHFFFAOYSA-N 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 238000010411 cooking Methods 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 239000004576 sand Substances 0.000 description 4
- 238000010186 staining Methods 0.000 description 4
- 150000008163 sugars Chemical class 0.000 description 4
- 239000002253 acid Substances 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 238000004043 dyeing Methods 0.000 description 3
- 239000012467 final product Substances 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- 238000006277 sulfonation reaction Methods 0.000 description 3
- 238000010947 wet-dispersion method Methods 0.000 description 3
- NLXFWUZKOOWWFD-UHFFFAOYSA-N 1-(2-hydroxyethylamino)-4-(methylamino)anthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(NCCO)=CC=C2NC NLXFWUZKOOWWFD-UHFFFAOYSA-N 0.000 description 2
- FDTLQXNAPKJJAM-UHFFFAOYSA-N 2-(3-hydroxyquinolin-2-yl)indene-1,3-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C1C1=NC2=CC=CC=C2C=C1O FDTLQXNAPKJJAM-UHFFFAOYSA-N 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000013256 coordination polymer Substances 0.000 description 2
- 230000006326 desulfonation Effects 0.000 description 2
- 238000005869 desulfonation reaction Methods 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 229920005611 kraft lignin Polymers 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 239000006072 paste Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 230000001603 reducing effect Effects 0.000 description 2
- 230000004044 response Effects 0.000 description 2
- 229920005552 sodium lignosulfonate Polymers 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 238000010561 standard procedure Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000000542 sulfonic acid group Chemical group 0.000 description 2
- 238000010998 test method Methods 0.000 description 2
- HXXLWTPFYWMBSC-UHFFFAOYSA-N 2-[3-chloro-4-[(2,6-dichloro-4-nitrophenyl)diazenyl]-n-(2-hydroxyethyl)anilino]ethanol Chemical compound ClC1=CC(N(CCO)CCO)=CC=C1N=NC1=C(Cl)C=C([N+]([O-])=O)C=C1Cl HXXLWTPFYWMBSC-UHFFFAOYSA-N 0.000 description 1
- 229910001369 Brass Inorganic materials 0.000 description 1
- 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 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000010951 brass Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000011363 dried mixture Substances 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000004676 glycans Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 239000002655 kraft paper Substances 0.000 description 1
- 235000012054 meals Nutrition 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-M naphthalene-1-sulfonate Chemical compound C1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-M 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 235000021110 pickles Nutrition 0.000 description 1
- 238000005554 pickling Methods 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 238000004537 pulping Methods 0.000 description 1
- 229940079877 pyrogallol Drugs 0.000 description 1
- 150000004053 quinones Chemical class 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011122 softwood Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 239000012085 test solution Substances 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- 238000000108 ultra-filtration Methods 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08H—DERIVATIVES OF NATURAL MACROMOLECULAR COMPOUNDS
- C08H6/00—Macromolecular compounds derived from lignin, e.g. tannins, humic acids
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
- C09B67/0084—Dispersions of dyes
- C09B67/0085—Non common dispersing agents
- C09B67/0086—Non common dispersing agents anionic dispersing agents
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/44—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders
- D06P1/46—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders using compositions containing natural macromolecular substances or derivatives thereof
- D06P1/48—Derivatives of carbohydrates
- D06P1/50—Derivatives of cellulose
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/44—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders
- D06P1/64—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders using compositions containing low-molecular-weight organic compounds without sulfate or sulfonate groups
- D06P1/651—Compounds without nitrogen
- D06P1/65106—Oxygen-containing compounds
- D06P1/65118—Compounds containing hydroxyl groups
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Textile Engineering (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Molecular Biology (AREA)
- Dispersion Chemistry (AREA)
- Biochemistry (AREA)
- Materials Engineering (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
- Coloring (AREA)
- Compounds Of Unknown Constitution (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/123,696 US4308203A (en) | 1980-02-22 | 1980-02-22 | Sulfonated lignin dispersants and dyestuffs |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH650489A5 true CH650489A5 (de) | 1985-07-31 |
Family
ID=22410314
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1162/81A CH650489A5 (de) | 1980-02-22 | 1981-02-20 | Ligninaddukt und verfahren zu dessen herstellung. |
Country Status (9)
| Country | Link |
|---|---|
| JP (1) | JPS6045931B2 (enrdf_load_stackoverflow) |
| CH (1) | CH650489A5 (enrdf_load_stackoverflow) |
| DE (2) | DE3050990C2 (enrdf_load_stackoverflow) |
| FI (1) | FI65791C (enrdf_load_stackoverflow) |
| FR (1) | FR2476651A1 (enrdf_load_stackoverflow) |
| GB (1) | GB2069996B (enrdf_load_stackoverflow) |
| IT (1) | IT1142318B (enrdf_load_stackoverflow) |
| NO (2) | NO153732C (enrdf_load_stackoverflow) |
| SE (1) | SE452768B (enrdf_load_stackoverflow) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS60190482A (ja) * | 1984-03-05 | 1985-09-27 | リ−ド・リグニン・インコ−ポレ−テツド | リグニンアダクト組成物およびその製法、用途 |
| WO2019039609A1 (ja) * | 2017-08-24 | 2019-02-28 | 日本製紙株式会社 | リグニン誘導体化合物及びその用途 |
| CN116621885B (zh) * | 2023-05-23 | 2024-04-19 | 宁夏中盛新科技有限公司 | 2-氨基-4-乙酰氨基苯甲醚生产废水的资源化处理方法 |
-
1980
- 1980-07-23 SE SE8005328A patent/SE452768B/sv not_active IP Right Cessation
- 1980-07-24 NO NO802235A patent/NO153732C/no unknown
- 1980-08-11 DE DE3050990A patent/DE3050990C2/de not_active Expired
- 1980-08-11 DE DE3030315A patent/DE3030315C2/de not_active Expired
- 1980-09-09 FI FI802819A patent/FI65791C/fi not_active IP Right Cessation
- 1980-09-16 JP JP55128468A patent/JPS6045931B2/ja not_active Expired
- 1980-10-31 GB GB8035153A patent/GB2069996B/en not_active Expired
- 1980-12-09 FR FR8026090A patent/FR2476651A1/fr active Granted
-
1981
- 1981-02-20 IT IT47852/81A patent/IT1142318B/it active
- 1981-02-20 CH CH1162/81A patent/CH650489A5/de not_active IP Right Cessation
- 1981-03-13 NO NO81810875A patent/NO154967C/no unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FR2476651A1 (fr) | 1981-08-28 |
| NO810875L (no) | 1981-08-24 |
| DE3050990A1 (enrdf_load_stackoverflow) | 1985-07-04 |
| SE8005328L (sv) | 1981-08-23 |
| NO802235L (no) | 1981-08-24 |
| FI802819A7 (fi) | 1981-08-23 |
| NO154967B (no) | 1986-10-13 |
| IT8147852A0 (it) | 1981-02-20 |
| DE3050990C2 (de) | 1986-11-06 |
| NO153732B (no) | 1986-02-03 |
| FR2476651B1 (enrdf_load_stackoverflow) | 1983-05-20 |
| DE3030315A1 (de) | 1981-09-17 |
| FI65791B (fi) | 1984-03-30 |
| GB2069996A (en) | 1981-09-03 |
| JPS56118093A (en) | 1981-09-16 |
| JPS6045931B2 (ja) | 1985-10-12 |
| NO153732C (no) | 1986-05-14 |
| DE3030315C2 (de) | 1985-11-21 |
| SE452768B (sv) | 1987-12-14 |
| GB2069996B (en) | 1983-11-16 |
| FI65791C (fi) | 1984-07-10 |
| NO154967C (no) | 1987-01-21 |
| IT1142318B (it) | 1986-10-08 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |