WO1995011334A1 - Deinking chemicals - Google Patents
Deinking chemicals Download PDFInfo
- Publication number
- WO1995011334A1 WO1995011334A1 PCT/US1994/011386 US9411386W WO9511334A1 WO 1995011334 A1 WO1995011334 A1 WO 1995011334A1 US 9411386 W US9411386 W US 9411386W WO 9511334 A1 WO9511334 A1 WO 9511334A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- alkoxylated
- weight
- wastepaper
- aliphatic
- deinking
- Prior art date
Links
- 239000002761 deinking Substances 0.000 title claims abstract description 41
- 239000000126 substance Substances 0.000 title abstract description 15
- 239000010893 paper waste Substances 0.000 claims abstract description 40
- -1 phosphate ester Chemical class 0.000 claims abstract description 29
- 239000004359 castor oil Substances 0.000 claims abstract description 23
- 238000007639 printing Methods 0.000 claims abstract description 23
- 235000019438 castor oil Nutrition 0.000 claims abstract description 22
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 claims abstract description 22
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 19
- 239000000543 intermediate Substances 0.000 claims abstract description 17
- 150000001412 amines Chemical class 0.000 claims abstract description 16
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 claims abstract description 13
- 235000014113 dietary fatty acids Nutrition 0.000 claims abstract description 13
- 239000000194 fatty acid Substances 0.000 claims abstract description 13
- 229930195729 fatty acid Natural products 0.000 claims abstract description 13
- 150000001298 alcohols Chemical class 0.000 claims abstract description 12
- 150000004665 fatty acids Chemical class 0.000 claims abstract description 12
- 239000002245 particle Substances 0.000 claims abstract description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 11
- 150000004670 unsaturated fatty acids Chemical class 0.000 claims abstract description 10
- 235000021122 unsaturated fatty acids Nutrition 0.000 claims abstract description 10
- 150000001875 compounds Chemical class 0.000 claims abstract description 9
- 150000001408 amides Chemical class 0.000 claims abstract description 8
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 37
- 238000000034 method Methods 0.000 claims description 35
- 239000000203 mixture Substances 0.000 claims description 26
- 125000001931 aliphatic group Chemical group 0.000 claims description 25
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 18
- 239000000463 material Substances 0.000 claims description 15
- 239000000243 solution Substances 0.000 claims description 14
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 12
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 10
- 150000001735 carboxylic acids Chemical class 0.000 claims description 10
- 239000003054 catalyst Substances 0.000 claims description 8
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 claims description 7
- 239000000600 sorbitol Substances 0.000 claims description 7
- 230000021615 conjugation Effects 0.000 claims description 6
- 230000001172 regenerating effect Effects 0.000 claims description 6
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 claims description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 5
- 239000007864 aqueous solution Substances 0.000 claims description 5
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 4
- 229910052910 alkali metal silicate Inorganic materials 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 claims description 4
- 150000004056 anthraquinones Chemical class 0.000 claims description 4
- 150000003014 phosphoric acid esters Chemical class 0.000 claims description 3
- 229920000642 polymer Polymers 0.000 claims description 3
- 230000001590 oxidative effect Effects 0.000 claims description 2
- 239000007787 solid Substances 0.000 claims description 2
- 238000006482 condensation reaction Methods 0.000 claims 4
- 239000004115 Sodium Silicate Substances 0.000 claims 3
- 239000007844 bleaching agent Substances 0.000 claims 3
- 229910052911 sodium silicate Inorganic materials 0.000 claims 3
- 238000009896 oxidative bleaching Methods 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 1
- 150000007513 acids Chemical class 0.000 claims 1
- 239000000725 suspension Substances 0.000 abstract description 30
- 238000005188 flotation Methods 0.000 abstract description 11
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical class OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 abstract description 9
- 238000005406 washing Methods 0.000 abstract description 6
- 229910019142 PO4 Inorganic materials 0.000 abstract description 4
- 239000010452 phosphate Substances 0.000 abstract description 4
- 238000006243 chemical reaction Methods 0.000 description 22
- 239000000976 ink Substances 0.000 description 21
- 239000000047 product Substances 0.000 description 11
- 239000000835 fiber Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 239000002202 Polyethylene glycol Substances 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
- 229920001223 polyethylene glycol Polymers 0.000 description 6
- 238000010926 purge Methods 0.000 description 6
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 5
- 229920002582 Polyethylene Glycol 600 Polymers 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- 239000000945 filler Substances 0.000 description 4
- 230000008929 regeneration Effects 0.000 description 4
- 238000011069 regeneration method Methods 0.000 description 4
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical class CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 125000005456 glyceride group Chemical group 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 235000019198 oils Nutrition 0.000 description 3
- 235000019353 potassium silicate Nutrition 0.000 description 3
- UIIMBOGNXHQVGW-UHFFFAOYSA-N sodium;hydron;carbonate Chemical compound [Na+].OC(O)=O UIIMBOGNXHQVGW-UHFFFAOYSA-N 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- QGLWBTPVKHMVHM-KTKRTIGZSA-N (z)-octadec-9-en-1-amine Chemical compound CCCCCCCC\C=C/CCCCCCCCN QGLWBTPVKHMVHM-KTKRTIGZSA-N 0.000 description 2
- DPUOLQHDNGRHBS-UHFFFAOYSA-N Brassidinsaeure Natural products CCCCCCCCC=CCCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-UHFFFAOYSA-N 0.000 description 2
- 244000060011 Cocos nucifera Species 0.000 description 2
- 235000013162 Cocos nucifera Nutrition 0.000 description 2
- URXZXNYJPAJJOQ-UHFFFAOYSA-N Erucic acid Natural products CCCCCCC=CCCCCCCCCCCCC(O)=O URXZXNYJPAJJOQ-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- 235000019485 Safflower oil Nutrition 0.000 description 2
- 238000006887 Ullmann reaction Methods 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- DPUOLQHDNGRHBS-KTKRTIGZSA-N erucic acid Chemical compound CCCCCCCC\C=C/CCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-KTKRTIGZSA-N 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 150000002191 fatty alcohols Chemical class 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000006317 isomerization reaction Methods 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 229940055577 oleyl alcohol Drugs 0.000 description 2
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 229920002523 polyethylene Glycol 1000 Polymers 0.000 description 2
- 229910052573 porcelain Inorganic materials 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 235000005713 safflower oil Nutrition 0.000 description 2
- 239000003813 safflower oil Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 150000003626 triacylglycerols Chemical class 0.000 description 2
- 238000001291 vacuum drying Methods 0.000 description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- 238000005698 Diels-Alder reaction Methods 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 1
- 235000019482 Palm oil Nutrition 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- 235000019484 Rapeseed oil Nutrition 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 235000019486 Sunflower oil Nutrition 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- OGBUMNBNEWYMNJ-UHFFFAOYSA-N batilol Chemical class CCCCCCCCCCCCCCCCCCOCC(O)CO OGBUMNBNEWYMNJ-UHFFFAOYSA-N 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 235000012343 cottonseed oil Nutrition 0.000 description 1
- 239000002385 cottonseed oil Substances 0.000 description 1
- JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 description 1
- 239000010685 fatty oil Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 125000001145 hydrido group Chemical group *[H] 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 238000007648 laser printing Methods 0.000 description 1
- 239000000944 linseed oil Substances 0.000 description 1
- 235000021388 linseed oil Nutrition 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 229920000847 nonoxynol Polymers 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical class CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 238000007645 offset printing Methods 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 235000021313 oleic acid Nutrition 0.000 description 1
- 150000002889 oleic acids Chemical class 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 150000002924 oxiranes Chemical class 0.000 description 1
- 125000000466 oxiranyl group Chemical group 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 239000002540 palm oil Substances 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 238000012643 polycondensation polymerization Methods 0.000 description 1
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical class CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical class O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- UKLNMMHNWFDKNT-UHFFFAOYSA-M sodium chlorite Chemical compound [Na+].[O-]Cl=O UKLNMMHNWFDKNT-UHFFFAOYSA-M 0.000 description 1
- 229960002218 sodium chlorite Drugs 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 235000020354 squash Nutrition 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000002600 sunflower oil Substances 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
Classifications
-
- D—TEXTILES; PAPER
- D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
- D21C—PRODUCTION OF CELLULOSE BY REMOVING NON-CELLULOSE SUBSTANCES FROM CELLULOSE-CONTAINING MATERIALS; REGENERATION OF PULPING LIQUORS; APPARATUS THEREFOR
- D21C5/00—Other processes for obtaining cellulose, e.g. cooking cotton linters ; Processes characterised by the choice of cellulose-containing starting materials
- D21C5/02—Working-up waste paper
- D21C5/025—De-inking
- D21C5/027—Chemicals therefor
-
- D—TEXTILES; PAPER
- D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
- D21B—FIBROUS RAW MATERIALS OR THEIR MECHANICAL TREATMENT
- D21B1/00—Fibrous raw materials or their mechanical treatment
- D21B1/04—Fibrous raw materials or their mechanical treatment by dividing raw materials into small particles, e.g. fibres
- D21B1/12—Fibrous raw materials or their mechanical treatment by dividing raw materials into small particles, e.g. fibres by wet methods, by the use of steam
- D21B1/30—Defibrating by other means
- D21B1/32—Defibrating by other means of waste paper
- D21B1/325—Defibrating by other means of waste paper de-inking devices
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02W—CLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO WASTEWATER TREATMENT OR WASTE MANAGEMENT
- Y02W30/00—Technologies for solid waste management
- Y02W30/50—Reuse, recycling or recovery technologies
- Y02W30/64—Paper recycling
Definitions
- This invention relates to a process for regenerating wastepaper, and more specifically, to the use therefor of castor oil derivatives as deinking chemicals which have been prepared by reacting the hydroxy groups of castor oil with an alkoxylated fatty acid, alcohol, amine, amide, phosphate ester, polyhydroxy alcohol, or sorbitan.
- the invention relates to a process for regenerating wastepaper, and more specifically, to the use therefor of deinking chemicals prepared by isomerizing dienoic or trienoic compounds to conjugated intermediates and then reacting the intermediates with unsaturated fatty acids, alcohols, amines, sorbitan esters or sorbitol esters and .hen alkoxylating the reaction product.
- the conjugated intermediates are reacted with alkoxylated unsaturated fatty acids, alcohols, amines, sorbitan esters or sorbitol esters .
- wastepaper is used in large quantities for the production of, for example, newsprint and hygiene paper. Brightness and color are important quality features for papers of this type.
- the printing inks have to be removed from the printed wastepaper. This is normally done by deinking processes essentially comprising two steps, namely:
- the second step can be carried out by washing or flotation (Ullmanns Encyclopadie der ischen Chemie, 4th Edition. Vol. 17, pages 570-571 (1979)).
- flotation which utilizes the difference in wetability between printing inks and paper fibers, air is forced or drawn through the fiber suspension. Small air bubbles attach themselves to the printing ink particles and form a froth at the surface of the water which is removed.
- the deinking of wastepaper is normally carried out at alkaline pH values in the presence of alkali metal hydroxides, alkali metal silicates, oxidative bleaches and surfactants at temperatures in the range from 30 to 50°C.
- Anionic and/or nonionic surfactants for example soaps, ethoxylated fatty alcohols and/or ethoxylated alkyl phenols are mainly used as surfactants (Wochenblatt fur Textilfabrikation 17, 646 to 649 (1985)). Discussion of Related Art
- DE-OS 31 01 444 relates to a process for the deinking of wastepaper using a compound corresponding to the following general formula
- R is a C 7 _ 21 alkyl or alkenyl group
- R 1 is a hydro ⁇ gen atom or a C ⁇ _ 1Q alkyl, alkenyl or acyl group
- AO represents C 3 H 6 0 or C 4 H 8 0 groups or a mixture of C 2 H 4 0, C 3 H 6 0 and C 4 H 8 0 groups
- m is an integer of 1 to 100
- n is an integer of 1 to 100.
- ethoxylated castor oils for the deinking of printed wastepaper is known, for example, from JP 78/52705, reported in Chem. Abstr. 89. 131445J (1978), and from DE 21 48 590.
- the Japanese patent describes mixtures of castor oil with 10 to 400% ethylene oxide and ethoxylated nonylphenol which are suitable for the removal of printing inks from printed wastepaper.
- the process disclosed in DE- PS 21 48 590 is concerned with organic materials, for example paper, which are bleached with sodium chlorite in the presence of organic compounds containing at least one ethylene oxide and/or propylene oxide unit. Suitable organic compounds containing at least one alkylene oxide unit include inter alia ethoxylated castor oil.
- DE 39 23 393 discloses a process for regenerating wastepaper containing printing ink using an alkoxylation product of a C 10 -C 22 carboxylic acid or derivative thereof containing an OH group in one or more of the 9, 10, 13 and 14 positions on the carboxylic acid moiety.
- the alkoxylation product is obtained by epoxidizing unsaturated c ⁇ o ⁇ c 22 carboxylic acids or derivatives thereof, the oxirane ring of the epoxide is then opened by reaction with hydrogen or a protic compound to form hydroxy groups, and this material is then alkoxylated to the final product.
- Japan 291952/88 (equivalent to European patent application number 89311550.1) is directed to a deinking composition
- a deinking composition comprising a reaction product obtained by reacting a glyceride mixture derived from natural oil and fat with ethylene oxide and propylene oxide.
- the glyceride mixture contains 5 to 10%/wt of monoglycerides, 30 to 45%/wt of diglycerides, and 50 to 70%/wt of triglycerides.
- the reaction product has a molar ratio of ethylene oxide to propylene oxide of between 1.8 to 2.2 wherein the mole number of added ethylene oxide is between 30 to 80 per mole of glycerides.
- German patent application 40 32 050.2 filed October 9, 1990 relates to regenerating printed wastepaper using the reaction product of alkoxylated aliphatic alcohols, amines, carboxylic acids, and carboxylic amides with epoxidized triglycerides such as C 10 - C 22 carboxylic acid derivatives.
- castor oil derivatives which have been prepared by reacting the hydroxy groups of castor oil with an alkoxylated fatty acid, alcohol, amine, amide, phosphate ester, polyhydroxy alcohol, or sorbitan are eminently suitable in processes for the deinking and regeneration of printed wastepaper.
- the present invention relates to a process for the regeneration of wastepaper wherein printed wastepaper is refined in known manner in the presence of deinking compounds obtained by reaction of the hydroxy groups of castor oil with an alkoxylated material selected from the group consisting of alkoxylated aliphatic C j -C ⁇ alcohols, alkoxylated aliphatic amines, alkoxylated aliphatic C 1 -C 22 carboxylic acids, alkoxylated aliphatic C- ⁇
- the castor oil employed in preparing the castor oil derivatives in accordance with this invention may be any naturally occurring castor oil containing double bonds and hydroxy groups, or the castor oil may be hydrogenated.
- the castor oil is reacted with aliphatic C 1 -C 22 alcohols alkoxylated with from 2 to 200 moles of ethylene oxide, for example ethoxylated methanol and/or ethoxylated fatty alcohols, aliphatic amines alkoxylated with from 2 to 200 moles of ethylene oxide, for example ethoxylated propylamine, dodecylamine, stearyla ine, oleylamine and/or coconut fatty amine, aliphatic C ⁇ 22 carboxylic acids and/or the amides thereof alkoxylated with from 2 to 200 moles of ethylene oxide, for example ethoxylated propionic acid, stearic acid, oleic acid and/or coconut fatty acid (J.
- aliphatic C 1 -C 22 alcohols alkoxylated with from 2 to 200 moles of ethylene oxide
- ethylene oxide for example ethoxylated methanol and/or ethoxylated
- phosphate esters alkoxylated with from 2 to 200 moles of ethylene oxide for example, a C 12 -C 15 alcohol phosphate ester alkoxylated with 5 moles of ethylene oxide, sorbitol alkoxylated with from 2 to 200 moles of ethylene oxide, for example, sorbitol alkoxylated with 40 moles of ethylene oxide, sorbitan alkoxylated with from 2 to 200 moles of ethylene oxide, for example, sorbitan alkoxylated with 40 moles of ethylene oxide, and polyhydroxy alcohols alkoxylated with 2 to 200 moles of ethylene oxide, for example, glycerol alkoxylated with 26 moles of ethylene oxide. It is particularly preferred that the castor oil be reacted with an alkoxylated carboxylic acid, alkoxylated alcohol, or alkoxylated sorbitol.
- the afore-mentioned alkoxylated materials may be obtained by known industrial methods, preferably by alkoxylation with ethylene oxide, propylene oxide and/or butylene oxide and more preferably with ethylene oxide and/or propylene oxide, optionally in the presence of catalysts, for example potassium hydroxide and/or sodium methylate, at temperatures of 110 to 200°C and preferably at temperatures of 140 to 175°C and under pressures of 10 5 to 2•10 6 Pa and preferably under pressures of 3 •10 5 to 5•10 5 Pa (cf_. for example "Chemische Technologie", Vol. 7, pages 131 to 132, Carl-Hanser-Verlag, Munchen/Wein (1986)).
- catalysts for example potassium hydroxide and/or sodium methylate
- deinking chemicals prepared by isomerizing dienoic or trienoic compounds to conjugated intermediates thereof and then reacting the intermediates with unsaturated fatty acids, alcohols, amines, sorbitan esters or sorbitol esters and then alkoxylating the reaction product are eminently suitable in processes for the deinking and regeneration of printed wastepaper.
- the conjugated intermediates are reacted with alkoxylated unsaturated fatty acids, alcohols, amines, sorbitan esters or sorbitol esters.
- the present invention also relates to a process for the regeneration of wastepaper wherein printed wastepaper is refined in known manner in the presence of deinking chemicals obtained by isomerizing dienoic or trienoic fatty acids in the presence of a conjugation catalyst to form conjugated double bonds therein, and then reacting the conjugated intermediates with an alkoxylated or nonalkoxylated unsaturated fatty acid, alcohol, amine, sorbitan ester or sorbitol ester via the Diels-Alder condensation polymerization reaction method, and the printing ink particles are subsequently removed from the fiber suspensions in known manner by flotation and/or washing.
- dienoic or trienoic fatty acids are isomerized in the presence of a conjugation catalyst, e.g. anthraquinone and similar compounds, to conjugated intermediates having double bonds by heating the fatty acids or oils at a temperature of from about 260°C to about
- a conjugation catalyst e.g. anthraquinone and similar compounds
- the conjugated intermediates are then reacted with an alkoxylated or non-alkoxylated unsaturated fatty acid, alcohol, amine, sorbitan ester or sorbitol ester. If the reaction is performed with non-alkoxylated forms of the afore-mentioned materials, then following the reaction, the products are alkoxylated to provide the deinking chemicals of this invention.
- the fatty acids suitable for isomerization herein include unsaturated C 10 *" c 22 carboxylic acids which have at least 2 or 3 double bonds in the 9-, 12-, and/or 15- positions, preferably predominantly of unsaturated C 16 _ 22 carboxylic acids which have at least 2 or 3 double bonds in the 9-, 12- and/or 15-positions, such as olive oil, linseed oil, sunflower oil, safflower oil, soybean oil, peanut oil, cottonseed oil, rapeseed oil which is rich in erucic acid and/or low in erucic acid, palm oil, lard and/or tallow.
- the conjugated dienoic structures readily react with any activated double bond to form ring structures. This reaction requires low energy and occurs readily at a reaction temperature of 200-350°C.
- the alkoxylated reactant suitable herein includes alkoxylated aliphatic C 2 -C 22 alcohols, alkoxylated aliphatic amines, alkoxylated aliphatic C 2 -C 22 carboxylic acids, and alkoxylated aliphatic C 2 -C 22 carboxylic acid amides; preferably, aliphatic C 2 -C 22 alcohols alkoxylated with from 2 to 200 moles of ethylene oxide, for example, ethoxylated oleyl alcohol or ethoxylated alkenyl alcohols, aliphatic amines alkoxylated with from 2 to 200 moles of ethylene oxide, for example ethoxylated oleylamine, aliphatic C 2 -C 22 carboxylic acids or the amides thereof alkoxylated with from 2 to 200 moles of ethylene oxide, for example ethoxylated oleic acid.
- the reactions be C ed out with aliphatic C 2 -C 2 alcohols alkoxylated with from 2 to 200 moles of ethylene oxide or aliphatic amines alkoxylated with from 2 to 200 moles of ethylene oxide.
- the reaction products may then be alkoxylated by known industrial methods, preferably with ethylene oxide, propylene oxide and/or butylene oxide and more preferably with ethylene oxide and/or propylene oxide, optionally in the presence of catalysts, for example potassium hydroxide and/or sodium methylate, at temperatures of 110 to 200°C and preferably at temperatures of 140 to 175°C and under pressures of 10 5 to 2•10 6 Pa and preferably under pressures of 3 ⁇ 10 5 to 5-10 5 Pa (cf. for example "chemische Technologie", Vol. 7, pages 131 to 132, Carl-Hanser-Verlag, M ⁇ nchen/Wein (1986)).
- catalysts for example potassium hydroxide and/or sodium methylate
- the deinking chemicals in accordance with this invention are employed by addition to paper stock suspensions in quantities of preferably 0.01 to 5% by weight and, more preferably, 0.1 to 0.8% by weight, based on air dry paper stock.
- Air-dry paper stock means that an equilibrium state of internal moisture has established itself in the paper stock. This equilibrium state depends both on the temperature and on the relative humidity of the air.
- the deinking result i.e., the removal of printing inks from printed wastepaper
- the deinking chemicals of this invention in combination with, for example, C 10 -C 22 fatty acids, such as Olinor® 4010, Olinor® 4020 and/or 01inor®DG40 (all products of Henkel Corporation) , enzymes, surfactants such as ethoxylated C 6 -C 22 alcohols, ethoxylated alkylphenols, polymers such as polyacrylamides and/or polydimethylaminoethyl methacrylic acid, and/or copolymers of the type described, for example in DE 38 39 479.
- C 10 -C 22 fatty acids such as Olinor® 4010, Olinor® 4020 and/or 01inor®DG40 (all products of Henkel Corporation)
- enzymes such as ethoxylated C 6 -C 22 alcohols, ethoxylated alkylphenols
- polymers such as polyacrylamides
- water-dilutable and/or solvent-containing printing inks and/or solvent-free inks especially water- dilutable printing inks, for example rotary newsprint inks, book printing inks, offset printing inks, illustration intaglio printing inks, flexographic printing inks, laser printing inks and/or packaging intaglio printing inks, may be removed from printed wastepaper, for example newspapers, magazines, computer paper, journals, brochures, forms, telephone directories and/or catalogues.
- the deinked wastepaper obtained is distinguished by very high degrees of whiteness.
- Printed wastepaper is refined in a pulper at 20°C to 80°C at a pulp concentration of, for example, 1 to 30% by weight in an aqueous solution typically containing 0 to 2.0% by weight 100% hydrogen peroxide, 0 to 2.5% by weight NaOH, 0 to 4.0% by weight soda waterglass (silicate) having a solids content of about 35% by weight (37 to 40°Be) , 0.01 to 5% by weight of the deinking chemicals according to the invention, and 0 to 1% by weight of the optional constituents mentioned above (all percentages by weight based on air-dry wastepaper) .
- an aqueous solution typically containing 0 to 2.0% by weight 100% hydrogen peroxide, 0 to 2.5% by weight NaOH, 0 to 4.0% by weight soda waterglass (silicate) having a solids content of about 35% by weight (37 to 40°Be) , 0.01 to 5% by weight of the deinking chemicals according to the invention, and 0 to 1% by weight of the optional constituents
- the paper stock suspensions are stirred into water or water is added to them so that 0.6 to 1.6% by weight stock suspensions are obtained.
- the detached printing ink particles are then removed from the stock suspensions in known manner by washing out or by flotation (Ullmanns Enzyklopadie der ischen Chemie, 4th Edition, Vol. 17, pages 570 to 571 (1979)). Flotation is preferably carried out in known manner, for example in a Denver flotation cell.
- Example I About 150 grams of PEG 600 (Polyethylene glycol molecular weight 600) monolaurate, about 150 grams of PEG 1000 (polyethylene glycol, molecular weight 1000) monostearate, about 100 grams of hydrogenated castor oil and about 0.1 gram of para-toluenesulfonic acid were added to a reaction flask, and the mixture was heated to about 200°C under a N 2 purge. After about 5 hours, the reaction was stopped and the product was found to have a cloud point of about 27°C.
- PEG 600 Polyethylene glycol molecular weight 600
- PEG 1000 polyethylene glycol, molecular weight 1000
- Example II About 300 grams of PEG 600 (polyethylene glycol, M.W. 600) monolaurate, about 100 grams of castor oil and about 0.3 gram of para-toluenesulfonic acid were added to a reaction flask, and the mixture was heated to about 200°C under a N 2 purge. When the product was found to have a cloud point of about 24°C (after about 9.5 hours), the reaction was stopped.
- PEG 600 polyethylene glycol, M.W. 600
- Example III About 300 grams of PEG 600 (polyethylene glycol, M.W. 600) monolaurate, about 100 grams of hydrogenated castor oil and about 0.3 gram of para-toluenesulfonic acid were added to a reaction flask, and the mixture was heated to about 200°C under a N 2 purge. When the product was found to have a cloud point of about 24.5°C (after about 12 hours) , the reaction was stopped.
- PEG 600 polyethylene glycol, M.W. 600
- Example IV About 150 grams of PEG 600 (polyethylene glycol, M.W. 600) monolaurate, about 150 grams of PEG 1000 (polyethylene glycol, M.W. 1000) monostearate, about 100 grams of hydrogenated castor oil and about 0.3 gram of para- toluenesulfonic acid were added to a reaction flask, and the mixture was heated to about 200°C under a N 2 purge. When the product was found to have a cloud point of about 27°C (after about 8 hours) , the reaction was stopped.
- PEG 600 polyethylene glycol, M.W. 600
- PEG 1000 polyethylene glycol, M.W. 1000
- Example VII About 75 grams of safflower oil, about 3.75 grams of anthraquinone and about 225 grams of oleyl alcohol contain ⁇ ing 23 moles of ethylene oxide were added to a reaction flask, and the mixture was heated to about 200°C for about 1 hour under a N 2 purge to drive out any moisture. A condenser was attached to the reaction flask and the temperature was raised to about 300°C. The mixture was thus heated for about 7.5 hours. While heating, the cloud point of the solution was monitored, and at a cloud point of about 24 ⁇ C the reaction was stopped.
- Example VIII The product of Example VII was evaluated for brightness gain, filler loss, fiber loss and total loss, and the values obtained were compared with those obtained using the deinking composition of German Patent 39 23 393 and Japan Patent 291952/88.
- a sample of the stock suspension was taken to form a pre-float pad.
- the stock suspension was then floated for 8 minutes at 45°C in a Denver flotation cell at 1500 revolutions per minute and another sample of the stock suspension was taken to form a final pad.
- the stock suspension samples were separated from the water on a Coors porcelain funnel and shaped into a sheet between two filter papers on a vacuum drying press and dried for 5 minutes.
- the evaluation results are plotted in Figure 3 for brightness gain, and in Figure 4 for percent filler, fiber and total loss. It can be seen therefrom that the deinking chemical of this invention performed as well as or better than the composition of German Patent 39 23 393 and that of Japan Patent 291952/88.
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- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Mechanical Engineering (AREA)
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
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- Paper (AREA)
Abstract
Description
Claims
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP19940930648 EP0724661A1 (en) | 1993-10-19 | 1994-10-11 | Deinking chemicals |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US08/139,236 | 1993-10-19 | ||
US08/139,236 US5505817A (en) | 1993-10-19 | 1993-10-19 | Deinking wastepaper using reaction products of castor oil with an alkoxylated material |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1995011334A1 true WO1995011334A1 (en) | 1995-04-27 |
Family
ID=22485701
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/US1994/011386 WO1995011334A1 (en) | 1993-10-19 | 1994-10-11 | Deinking chemicals |
Country Status (4)
Country | Link |
---|---|
US (1) | US5505817A (en) |
EP (1) | EP0724661A1 (en) |
CA (1) | CA2172836A1 (en) |
WO (1) | WO1995011334A1 (en) |
Families Citing this family (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5582681A (en) | 1994-06-29 | 1996-12-10 | Kimberly-Clark Corporation | Production of soft paper products from old newspaper |
US6001218A (en) | 1994-06-29 | 1999-12-14 | Kimberly-Clark Worldwide, Inc. | Production of soft paper products from old newspaper |
GB9422878D0 (en) * | 1994-11-12 | 1995-01-04 | Stephenson Group | Recycling of fibre products |
US5658427A (en) * | 1995-08-01 | 1997-08-19 | Geo Specialty Chemicals, Inc. | Ethoxylated soya glycerides with glycols as deinking collector modifiers |
US5837097A (en) * | 1995-12-20 | 1998-11-17 | Lion Corporation | Deinking agent for regenerating waste paper and method for deinking waste paper |
US6296736B1 (en) | 1997-10-30 | 2001-10-02 | Kimberly-Clark Worldwide, Inc. | Process for modifying pulp from recycled newspapers |
US6387210B1 (en) | 1998-09-30 | 2002-05-14 | Kimberly-Clark Worldwide, Inc. | Method of making sanitary paper product from coarse fibers |
US6666950B2 (en) | 2001-11-28 | 2003-12-23 | Basf Ag | Process for deinking paper using a triglyceride |
US7169257B2 (en) * | 2003-11-12 | 2007-01-30 | Kemira Chemicals, Inc. | Method of deinking waste paper using a reduced alkali system |
US20130029111A1 (en) * | 2011-07-29 | 2013-01-31 | Bhattacharyya Manoj K | Post-treatment composition for a digitally printed image |
US9539822B2 (en) | 2012-01-13 | 2017-01-10 | Hewlett-Packard Development Company, L.P. | Digital printers |
JP6613191B2 (en) * | 2016-03-28 | 2019-11-27 | 日本製紙株式会社 | Method for deinking UV printed matter |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0369667A2 (en) * | 1988-11-18 | 1990-05-23 | Kao Corporation | Deinking agent |
CA2093813A1 (en) * | 1990-10-09 | 1992-04-10 | Peter Daute | Use of compounds containing polyether chains prepared from epoxidized carboxylic acid derivatives for the removal of printing inks from wastepaper and/or paper circuit waters |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
BE789533A (en) * | 1971-09-29 | 1973-03-29 | Hoechst Ag | BLEACHING WITH CHLORITES |
JPS5352705A (en) * | 1976-10-21 | 1978-05-13 | Miyoshi Yushi Kk | Reagents to decolorize printed ink on used paper for reuse |
DE3101444A1 (en) * | 1981-01-19 | 1982-08-05 | Siemens Ag | Laser transmission device |
JPS63291952A (en) * | 1987-05-26 | 1988-11-29 | Daiseru Hiyurusu Kk | Polyamide resin composition |
DE3839479A1 (en) * | 1988-11-23 | 1990-06-07 | Henkel Kgaa | THINKING OF WASTE PAPER |
DE3923393A1 (en) * | 1989-07-14 | 1991-01-17 | Henkel Kgaa | METHOD FOR RECYCLING PAPER |
-
1993
- 1993-10-19 US US08/139,236 patent/US5505817A/en not_active Expired - Fee Related
-
1994
- 1994-10-11 CA CA 2172836 patent/CA2172836A1/en not_active Abandoned
- 1994-10-11 WO PCT/US1994/011386 patent/WO1995011334A1/en not_active Application Discontinuation
- 1994-10-11 EP EP19940930648 patent/EP0724661A1/en not_active Withdrawn
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0369667A2 (en) * | 1988-11-18 | 1990-05-23 | Kao Corporation | Deinking agent |
CA2093813A1 (en) * | 1990-10-09 | 1992-04-10 | Peter Daute | Use of compounds containing polyether chains prepared from epoxidized carboxylic acid derivatives for the removal of printing inks from wastepaper and/or paper circuit waters |
Also Published As
Publication number | Publication date |
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CA2172836A1 (en) | 1995-04-27 |
US5505817A (en) | 1996-04-09 |
EP0724661A1 (en) | 1996-08-07 |
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