EP1131483A1 - Inhibition of pulp and paper yellowing using hydroxylamines and other coadditives - Google Patents
Inhibition of pulp and paper yellowing using hydroxylamines and other coadditivesInfo
- Publication number
- EP1131483A1 EP1131483A1 EP99953767A EP99953767A EP1131483A1 EP 1131483 A1 EP1131483 A1 EP 1131483A1 EP 99953767 A EP99953767 A EP 99953767A EP 99953767 A EP99953767 A EP 99953767A EP 1131483 A1 EP1131483 A1 EP 1131483A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- pulp
- paper
- hydroxylamine
- tert
- acid
- 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.)
- Granted
Links
- 238000004383 yellowing Methods 0.000 title claims abstract description 48
- 150000002443 hydroxylamines Chemical class 0.000 title claims abstract description 13
- 230000005764 inhibitory process Effects 0.000 title description 12
- 239000006096 absorbing agent Substances 0.000 claims abstract description 41
- 239000003112 inhibitor Substances 0.000 claims abstract description 28
- GXELTROTKVKZBQ-UHFFFAOYSA-N n,n-dibenzylhydroxylamine Chemical compound C=1C=CC=CC=1CN(O)CC1=CC=CC=C1 GXELTROTKVKZBQ-UHFFFAOYSA-N 0.000 claims abstract description 24
- 229920005610 lignin Polymers 0.000 claims abstract description 19
- 150000003839 salts Chemical class 0.000 claims abstract description 19
- 230000000087 stabilizing effect Effects 0.000 claims abstract description 17
- 239000002738 chelating agent Substances 0.000 claims abstract description 15
- 229910052751 metal Inorganic materials 0.000 claims abstract description 15
- 239000002184 metal Substances 0.000 claims abstract description 15
- FVCOIAYSJZGECG-UHFFFAOYSA-N diethylhydroxylamine Chemical compound CCN(O)CC FVCOIAYSJZGECG-UHFFFAOYSA-N 0.000 claims abstract description 10
- 229920001174 Diethylhydroxylamine Polymers 0.000 claims abstract description 7
- 239000002253 acid Substances 0.000 claims abstract description 6
- 150000001408 amides Chemical group 0.000 claims abstract description 6
- 150000002148 esters Chemical group 0.000 claims abstract description 6
- 239000006081 fluorescent whitening agent Substances 0.000 claims abstract description 6
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims abstract description 6
- 239000012965 benzophenone Substances 0.000 claims abstract description 5
- -1 3,5-di-tert-butyl-4- hydroxyphenyl Chemical group 0.000 claims description 52
- 150000001875 compounds Chemical class 0.000 claims description 44
- 239000000123 paper Substances 0.000 claims description 41
- 239000000203 mixture Substances 0.000 claims description 39
- 239000002655 kraft paper Substances 0.000 claims description 20
- 239000003381 stabilizer Substances 0.000 claims description 16
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 15
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 15
- 229910052698 phosphorus Inorganic materials 0.000 claims description 15
- 239000011574 phosphorus Substances 0.000 claims description 15
- 229910052717 sulfur Inorganic materials 0.000 claims description 15
- 239000011593 sulfur Substances 0.000 claims description 15
- 229920001223 polyethylene glycol Polymers 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- QPCDCPDFJACHGM-UHFFFAOYSA-N N,N-bis{2-[bis(carboxymethyl)amino]ethyl}glycine Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(=O)O)CCN(CC(O)=O)CC(O)=O QPCDCPDFJACHGM-UHFFFAOYSA-N 0.000 claims description 7
- 229960003330 pentetic acid Drugs 0.000 claims description 7
- PSYGHMBJXWRQFD-UHFFFAOYSA-N 2-(2-sulfanylacetyl)oxyethyl 2-sulfanylacetate Chemical compound SCC(=O)OCCOC(=O)CS PSYGHMBJXWRQFD-UHFFFAOYSA-N 0.000 claims description 6
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 claims description 6
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 claims description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 6
- 150000001412 amines Chemical class 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- 229920001451 polypropylene glycol Polymers 0.000 claims description 6
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 5
- 239000002202 Polyethylene glycol Substances 0.000 claims description 5
- IBCYFTYCUDZFQB-UHFFFAOYSA-N n,n-bis(benzylsulfanylmethyl)hydroxylamine Chemical compound C=1C=CC=CC=1CSCN(O)CSCC1=CC=CC=C1 IBCYFTYCUDZFQB-UHFFFAOYSA-N 0.000 claims description 5
- 230000003647 oxidation Effects 0.000 claims description 5
- 238000007254 oxidation reaction Methods 0.000 claims description 5
- KYNFOMQIXZUKRK-UHFFFAOYSA-N 2,2'-dithiodiethanol Chemical compound OCCSSCCO KYNFOMQIXZUKRK-UHFFFAOYSA-N 0.000 claims description 4
- CNDCQWGRLNGNNO-UHFFFAOYSA-N 2-(2-sulfanylethoxy)ethanethiol Chemical compound SCCOCCS CNDCQWGRLNGNNO-UHFFFAOYSA-N 0.000 claims description 4
- GOKVSLADUAKALT-UHFFFAOYSA-N 3-[2-carboxyethyl(hydroxy)amino]propanoic acid Chemical compound OC(=O)CCN(O)CCC(O)=O GOKVSLADUAKALT-UHFFFAOYSA-N 0.000 claims description 4
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 150000004662 dithiols Chemical class 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 4
- PJUIMOJAAPLTRJ-UHFFFAOYSA-N monothioglycerol Chemical compound OCC(O)CS PJUIMOJAAPLTRJ-UHFFFAOYSA-N 0.000 claims description 4
- 229920001748 polybutylene Polymers 0.000 claims description 4
- 230000008569 process Effects 0.000 claims description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 4
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical class C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 claims description 3
- JYOCWMVETLTCNF-UHFFFAOYSA-N 1-[hydroxy(2-hydroxypropyl)amino]propan-2-ol Chemical group CC(O)CN(O)CC(C)O JYOCWMVETLTCNF-UHFFFAOYSA-N 0.000 claims description 3
- GBPNAALUHSMCQE-UHFFFAOYSA-N 3-[hydroxy(3-hydroxypropyl)amino]propan-1-ol Chemical group OCCCN(O)CCCO GBPNAALUHSMCQE-UHFFFAOYSA-N 0.000 claims description 3
- ACZGCWSMSTYWDQ-UHFFFAOYSA-N 3h-1-benzofuran-2-one Chemical class C1=CC=C2OC(=O)CC2=C1 ACZGCWSMSTYWDQ-UHFFFAOYSA-N 0.000 claims description 3
- 229910019142 PO4 Inorganic materials 0.000 claims description 3
- 239000007983 Tris buffer Substances 0.000 claims description 3
- 235000010323 ascorbic acid Nutrition 0.000 claims description 3
- 239000011668 ascorbic acid Substances 0.000 claims description 3
- 230000002708 enhancing effect Effects 0.000 claims description 3
- ITUWQZXQRZLLCR-UHFFFAOYSA-N n,n-dioctadecylhydroxylamine Chemical group CCCCCCCCCCCCCCCCCCN(O)CCCCCCCCCCCCCCCCCC ITUWQZXQRZLLCR-UHFFFAOYSA-N 0.000 claims description 3
- MGFYIUFZLHCRTH-UHFFFAOYSA-N nitrilotriacetic acid Chemical compound OC(=O)CN(CC(O)=O)CC(O)=O MGFYIUFZLHCRTH-UHFFFAOYSA-N 0.000 claims description 3
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 claims description 3
- 239000003760 tallow Substances 0.000 claims description 3
- CDBORKXXLPAUKJ-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanethiol Chemical compound COCCOCCS CDBORKXXLPAUKJ-UHFFFAOYSA-N 0.000 claims description 2
- URDCARMUOSMFFI-UHFFFAOYSA-N 2-[2-[bis(carboxymethyl)amino]ethyl-(2-hydroxyethyl)amino]acetic acid Chemical compound OCCN(CC(O)=O)CCN(CC(O)=O)CC(O)=O URDCARMUOSMFFI-UHFFFAOYSA-N 0.000 claims description 2
- IJVRPNIWWODHHA-UHFFFAOYSA-N 2-cyanoprop-2-enoic acid Chemical class OC(=O)C(=C)C#N IJVRPNIWWODHHA-UHFFFAOYSA-N 0.000 claims description 2
- ISWYKPNDQAPSER-UHFFFAOYSA-N 3,4a,5a,7-tetratert-butyl-11-fluoro-5-methyl-9a,12a-dihydro-5h-benzo[d][1,3,2]benzodioxaphosphocine Chemical compound O1P(F)OC2C=CC(C(C)(C)C)=CC2(C(C)(C)C)C(C)C2(C(C)(C)C)C=C(C(C)(C)C)C=CC21 ISWYKPNDQAPSER-UHFFFAOYSA-N 0.000 claims description 2
- HQQTZCPKNZVLFF-UHFFFAOYSA-N 4h-1,2-benzoxazin-3-one Chemical class C1=CC=C2ONC(=O)CC2=C1 HQQTZCPKNZVLFF-UHFFFAOYSA-N 0.000 claims description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical group CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical group OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical group OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 2
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical group [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 claims description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical group [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical group [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical group [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 2
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical group [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 claims description 2
- RGHNJXZEOKUKBD-SQOUGZDYSA-M D-gluconate Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O RGHNJXZEOKUKBD-SQOUGZDYSA-M 0.000 claims description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical group [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 claims description 2
- AEMRFAOFKBGASW-UHFFFAOYSA-M Glycolate Chemical compound OCC([O-])=O AEMRFAOFKBGASW-UHFFFAOYSA-M 0.000 claims description 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-L L-tartrate(2-) Chemical group [O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O FEWJPZIEWOKRBE-JCYAYHJZSA-L 0.000 claims description 2
- 229910002651 NO3 Inorganic materials 0.000 claims description 2
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical group [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims description 2
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical group OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 2
- JKIJEFPNVSHHEI-UHFFFAOYSA-N Phenol, 2,4-bis(1,1-dimethylethyl)-, phosphite (3:1) Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC=C1OP(OC=1C(=CC(=CC=1)C(C)(C)C)C(C)(C)C)OC1=CC=C(C(C)(C)C)C=C1C(C)(C)C JKIJEFPNVSHHEI-UHFFFAOYSA-N 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical group [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical group OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 claims description 2
- YGOTUFHSCQXRRN-UHFFFAOYSA-N [PH2](OCO)=O.[Na] Chemical compound [PH2](OCO)=O.[Na] YGOTUFHSCQXRRN-UHFFFAOYSA-N 0.000 claims description 2
- IRYSNLPWOIOTED-UHFFFAOYSA-N acetic acid ethane-1,2-diamine Chemical compound CC(O)=O.CC(O)=O.CC(O)=O.CC(O)=O.NCCN.NCCN IRYSNLPWOIOTED-UHFFFAOYSA-N 0.000 claims description 2
- 150000008052 alkyl sulfonates Chemical class 0.000 claims description 2
- 150000001449 anionic compounds Chemical group 0.000 claims description 2
- 150000001450 anions Chemical class 0.000 claims description 2
- 125000005228 aryl sulfonate group Chemical group 0.000 claims description 2
- 229940072107 ascorbate Drugs 0.000 claims description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical group OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 2
- 150000001558 benzoic acid derivatives Chemical class 0.000 claims description 2
- 150000008366 benzophenones Chemical class 0.000 claims description 2
- 150000001565 benzotriazoles Chemical class 0.000 claims description 2
- 150000007942 carboxylates Chemical class 0.000 claims description 2
- 150000001768 cations Chemical class 0.000 claims description 2
- ZJIPHXXDPROMEF-UHFFFAOYSA-N dihydroxyphosphanyl dihydrogen phosphite Chemical compound OP(O)OP(O)O ZJIPHXXDPROMEF-UHFFFAOYSA-N 0.000 claims description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical compound [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 claims description 2
- 229940050410 gluconate Drugs 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical group OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 claims description 2
- LVHBHZANLOWSRM-UHFFFAOYSA-N itaconic acid Chemical compound OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 claims description 2
- 229940049920 malate Drugs 0.000 claims description 2
- BJEPYKJPYRNKOW-UHFFFAOYSA-L malate(2-) Chemical compound [O-]C(=O)C(O)CC([O-])=O BJEPYKJPYRNKOW-UHFFFAOYSA-L 0.000 claims description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 2
- IWYDHOAUDWTVEP-UHFFFAOYSA-M mandelate Chemical compound [O-]C(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-M 0.000 claims description 2
- VMESOKCXSYNAKD-UHFFFAOYSA-N n,n-dimethylhydroxylamine Chemical group CN(C)O VMESOKCXSYNAKD-UHFFFAOYSA-N 0.000 claims description 2
- 150000002891 organic anions Chemical group 0.000 claims description 2
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 239000010452 phosphate Substances 0.000 claims description 2
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical group [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 claims description 2
- 229920000058 polyacrylate Polymers 0.000 claims description 2
- 229920000193 polymethacrylate Polymers 0.000 claims description 2
- 229940095064 tartrate Drugs 0.000 claims description 2
- 230000000930 thermomechanical effect Effects 0.000 claims description 2
- YODZTKMDCQEPHD-UHFFFAOYSA-N thiodiglycol Chemical compound OCCSCCO YODZTKMDCQEPHD-UHFFFAOYSA-N 0.000 claims description 2
- UIERETOOQGIECD-ONEGZZNKSA-N tiglic acid Chemical compound C\C=C(/C)C(O)=O UIERETOOQGIECD-ONEGZZNKSA-N 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
- XTLFYLHNQDOOOK-UHFFFAOYSA-N tris(2,4-ditert-butyl-6-ethylphenyl) phosphite Chemical compound CCC1=CC(C(C)(C)C)=CC(C(C)(C)C)=C1OP(OC=1C(=CC(=CC=1CC)C(C)(C)C)C(C)(C)C)OC1=C(CC)C=C(C(C)(C)C)C=C1C(C)(C)C XTLFYLHNQDOOOK-UHFFFAOYSA-N 0.000 claims 1
- 229920001131 Pulp (paper) Polymers 0.000 abstract description 12
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 abstract description 3
- 239000012964 benzotriazole Substances 0.000 abstract description 3
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 abstract description 2
- 150000003863 ammonium salts Chemical class 0.000 abstract 1
- 230000032683 aging Effects 0.000 description 10
- 229940126062 Compound A Drugs 0.000 description 8
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 8
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 7
- ZMWRRFHBXARRRT-UHFFFAOYSA-N 2-(benzotriazol-2-yl)-4,6-bis(2-methylbutan-2-yl)phenol Chemical compound CCC(C)(C)C1=CC(C(C)(C)CC)=CC(N2N=C3C=CC=CC3=N2)=C1O ZMWRRFHBXARRRT-UHFFFAOYSA-N 0.000 description 6
- 239000000654 additive Substances 0.000 description 6
- 150000003254 radicals Chemical class 0.000 description 6
- BWEQSGJKNHMSPA-UHFFFAOYSA-N N.ON Chemical compound N.ON BWEQSGJKNHMSPA-UHFFFAOYSA-N 0.000 description 5
- YGUMVDWOQQJBGA-VAWYXSNFSA-N 5-[(4-anilino-6-morpholin-4-yl-1,3,5-triazin-2-yl)amino]-2-[(e)-2-[4-[(4-anilino-6-morpholin-4-yl-1,3,5-triazin-2-yl)amino]-2-sulfophenyl]ethenyl]benzenesulfonic acid Chemical compound C=1C=C(\C=C\C=2C(=CC(NC=3N=C(N=C(NC=4C=CC=CC=4)N=3)N3CCOCC3)=CC=2)S(O)(=O)=O)C(S(=O)(=O)O)=CC=1NC(N=C(N=1)N2CCOCC2)=NC=1NC1=CC=CC=C1 YGUMVDWOQQJBGA-VAWYXSNFSA-N 0.000 description 4
- 238000004061 bleaching Methods 0.000 description 4
- 238000002845 discoloration Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 3
- 230000000996 additive effect Effects 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- JNGZXGGOCLZBFB-IVCQMTBJSA-N compound E Chemical compound N([C@@H](C)C(=O)N[C@@H]1C(N(C)C2=CC=CC=C2C(C=2C=CC=CC=2)=N1)=O)C(=O)CC1=CC(F)=CC(F)=C1 JNGZXGGOCLZBFB-IVCQMTBJSA-N 0.000 description 3
- BKWJMVVESJNVDA-UHFFFAOYSA-N diethyl(hydroxy)azanium;2-hydroxypropane-1,2,3-tricarboxylate Chemical group CC[NH+](O)CC.CC[NH+](O)CC.CC[NH+](O)CC.[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O BKWJMVVESJNVDA-UHFFFAOYSA-N 0.000 description 3
- 238000007689 inspection Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 3
- 239000002516 radical scavenger Substances 0.000 description 3
- 159000000000 sodium salts Chemical class 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- RUFMFWSJTRYOPL-UHFFFAOYSA-N 3-(benzotriazol-2-yl)-5-butan-2-yl-4-hydroxybenzenesulfonic acid Chemical compound CCC(C)C1=CC(S(O)(=O)=O)=CC(N2N=C3C=CC=CC3=N2)=C1O RUFMFWSJTRYOPL-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 238000013459 approach Methods 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 229940090960 diethylenetriamine pentamethylene phosphonic acid Drugs 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- DUYCTCQXNHFCSJ-UHFFFAOYSA-N dtpmp Chemical compound OP(=O)(O)CN(CP(O)(O)=O)CCN(CP(O)(=O)O)CCN(CP(O)(O)=O)CP(O)(O)=O DUYCTCQXNHFCSJ-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- GDOPTJXRTPNYNR-UHFFFAOYSA-N methyl-cyclopentane Natural products CC1CCCC1 GDOPTJXRTPNYNR-UHFFFAOYSA-N 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 235000021317 phosphate Nutrition 0.000 description 2
- 239000013055 pulp slurry Substances 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 239000002023 wood Substances 0.000 description 2
- ARVUDIQYNJVQIW-UHFFFAOYSA-N (4-dodecoxy-2-hydroxyphenyl)-phenylmethanone Chemical compound OC1=CC(OCCCCCCCCCCCC)=CC=C1C(=O)C1=CC=CC=C1 ARVUDIQYNJVQIW-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- CSGAUKGQUCHWDP-UHFFFAOYSA-N 1-hydroxy-2,2,6,6-tetramethylpiperidin-4-ol Chemical compound CC1(C)CC(O)CC(C)(C)N1O CSGAUKGQUCHWDP-UHFFFAOYSA-N 0.000 description 1
- VUZNLSBZRVZGIK-UHFFFAOYSA-N 2,2,6,6-Tetramethyl-1-piperidinol Chemical compound CC1(C)CCCC(C)(C)N1O VUZNLSBZRVZGIK-UHFFFAOYSA-N 0.000 description 1
- RKMGAJGJIURJSJ-UHFFFAOYSA-N 2,2,6,6-Tetramethylpiperidine Substances CC1(C)CCCC(C)(C)N1 RKMGAJGJIURJSJ-UHFFFAOYSA-N 0.000 description 1
- ZXDDPOHVAMWLBH-UHFFFAOYSA-N 2,4-Dihydroxybenzophenone Chemical compound OC1=CC(O)=CC=C1C(=O)C1=CC=CC=C1 ZXDDPOHVAMWLBH-UHFFFAOYSA-N 0.000 description 1
- BYRPKBTYIOUNHY-UHFFFAOYSA-N 2-(3-tert-butyl-2-hydroxy-5-methylphenyl)benzotriazole-5-sulfonic acid Chemical compound CC(C)(C)C1=CC(C)=CC(N2N=C3C=C(C=CC3=N2)S(O)(=O)=O)=C1O BYRPKBTYIOUNHY-UHFFFAOYSA-N 0.000 description 1
- LHPPDQUVECZQSW-UHFFFAOYSA-N 2-(benzotriazol-2-yl)-4,6-ditert-butylphenol Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC(N2N=C3C=CC=CC3=N2)=C1O LHPPDQUVECZQSW-UHFFFAOYSA-N 0.000 description 1
- IYAZLDLPUNDVAG-UHFFFAOYSA-N 2-(benzotriazol-2-yl)-4-(2,4,4-trimethylpentan-2-yl)phenol Chemical compound CC(C)(C)CC(C)(C)C1=CC=C(O)C(N2N=C3C=CC=CC3=N2)=C1 IYAZLDLPUNDVAG-UHFFFAOYSA-N 0.000 description 1
- UZUNCLSDTUBVCN-UHFFFAOYSA-N 2-(benzotriazol-2-yl)-6-(2-phenylpropan-2-yl)-4-(2,4,4-trimethylpentan-2-yl)phenol Chemical compound C=1C(C(C)(C)CC(C)(C)C)=CC(N2N=C3C=CC=CC3=N2)=C(O)C=1C(C)(C)C1=CC=CC=C1 UZUNCLSDTUBVCN-UHFFFAOYSA-N 0.000 description 1
- ZSSVCEUEVMALRD-UHFFFAOYSA-N 2-[4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin-2-yl]-5-(octyloxy)phenol Chemical compound OC1=CC(OCCCCCCCC)=CC=C1C1=NC(C=2C(=CC(C)=CC=2)C)=NC(C=2C(=CC(C)=CC=2)C)=N1 ZSSVCEUEVMALRD-UHFFFAOYSA-N 0.000 description 1
- VVBVFVRWEMORTQ-UHFFFAOYSA-N 2-[4-(4,6-diphenyl-1,3,5-triazin-2-yl)-3-hydroxyphenoxy]ethyl 2-ethylhexanoate Chemical compound OC1=CC(OCCOC(=O)C(CC)CCCC)=CC=C1C1=NC(C=2C=CC=CC=2)=NC(C=2C=CC=CC=2)=N1 VVBVFVRWEMORTQ-UHFFFAOYSA-N 0.000 description 1
- OYGYNUPKLMDVHM-UHFFFAOYSA-N 3-[3-(benzotriazol-2-yl)-5-tert-butyl-4-hydroxyphenyl]propanoic acid Chemical compound CC(C)(C)C1=CC(CCC(O)=O)=CC(N2N=C3C=CC=CC3=N2)=C1O OYGYNUPKLMDVHM-UHFFFAOYSA-N 0.000 description 1
- CYHYIIFODCKQNP-UHFFFAOYSA-N 5,7-ditert-butyl-3-(3,4-dimethylphenyl)-3h-1-benzofuran-2-one Chemical compound C1=C(C)C(C)=CC=C1C1C(C=C(C=C2C(C)(C)C)C(C)(C)C)=C2OC1=O CYHYIIFODCKQNP-UHFFFAOYSA-N 0.000 description 1
- UWSMKYBKUPAEJQ-UHFFFAOYSA-N 5-Chloro-2-(3,5-di-tert-butyl-2-hydroxyphenyl)-2H-benzotriazole Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC(N2N=C3C=C(Cl)C=CC3=N2)=C1O UWSMKYBKUPAEJQ-UHFFFAOYSA-N 0.000 description 1
- HVDJXXVDNDLBQY-UHFFFAOYSA-N 5-butyl-5-ethyl-2-(2,4,6-tritert-butylphenoxy)-1,3,2-dioxaphosphinane Chemical compound O1CC(CCCC)(CC)COP1OC1=C(C(C)(C)C)C=C(C(C)(C)C)C=C1C(C)(C)C HVDJXXVDNDLBQY-UHFFFAOYSA-N 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical compound NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
- OCUCCJIRFHNWBP-IYEMJOQQSA-L Copper gluconate Chemical class [Cu+2].OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O.OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O OCUCCJIRFHNWBP-IYEMJOQQSA-L 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 229940123457 Free radical scavenger Drugs 0.000 description 1
- 241000208202 Linaceae Species 0.000 description 1
- 235000004431 Linum usitatissimum Nutrition 0.000 description 1
- 102000004316 Oxidoreductases Human genes 0.000 description 1
- 108090000854 Oxidoreductases Proteins 0.000 description 1
- XAKBSHICSHRJCL-UHFFFAOYSA-N [CH2]C(=O)C1=CC=CC=C1 Chemical group [CH2]C(=O)C1=CC=CC=C1 XAKBSHICSHRJCL-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000021736 acetylation Effects 0.000 description 1
- 238000006640 acetylation reaction Methods 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- YLFIGGHWWPSIEG-UHFFFAOYSA-N aminoxyl Chemical compound [O]N YLFIGGHWWPSIEG-UHFFFAOYSA-N 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000005013 aryl ether group Chemical group 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- ZEFSGHVBJCEKAZ-UHFFFAOYSA-N bis(2,4-ditert-butyl-6-methylphenyl) ethyl phosphite Chemical compound CC=1C=C(C(C)(C)C)C=C(C(C)(C)C)C=1OP(OCC)OC1=C(C)C=C(C(C)(C)C)C=C1C(C)(C)C ZEFSGHVBJCEKAZ-UHFFFAOYSA-N 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000007385 chemical modification Methods 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 239000008199 coating composition Substances 0.000 description 1
- 230000000593 degrading effect Effects 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- QDCHWIWENYCPIL-UHFFFAOYSA-L disodium;4-hydroxy-5-(2-hydroxy-4-methoxy-5-sulfonatobenzoyl)-2-methoxybenzenesulfonate Chemical compound [Na+].[Na+].C1=C(S([O-])(=O)=O)C(OC)=CC(O)=C1C(=O)C1=CC(S([O-])(=O)=O)=C(OC)C=C1O QDCHWIWENYCPIL-UHFFFAOYSA-L 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000004907 flux Effects 0.000 description 1
- PEDCQBHIVMGVHV-UHFFFAOYSA-N glycerol Substances OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 150000004715 keto acids Chemical class 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- IYSYLWYGCWTJSG-XFXZXTDPSA-N n-tert-butyl-1-phenylmethanimine oxide Chemical compound CC(C)(C)[N+](\[O-])=C\C1=CC=CC=C1 IYSYLWYGCWTJSG-XFXZXTDPSA-N 0.000 description 1
- QUAMTGJKVDWJEQ-UHFFFAOYSA-N octabenzone Chemical compound OC1=CC(OCCCCCCCC)=CC=C1C(=O)C1=CC=CC=C1 QUAMTGJKVDWJEQ-UHFFFAOYSA-N 0.000 description 1
- XQAABEDPVQWFPN-UHFFFAOYSA-N octyl 3-[3-(benzotriazol-2-yl)-5-tert-butyl-4-hydroxyphenyl]propanoate Chemical compound CC(C)(C)C1=CC(CCC(=O)OCCCCCCCC)=CC(N2N=C3C=CC=CC3=N2)=C1O XQAABEDPVQWFPN-UHFFFAOYSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
- 238000006303 photolysis reaction Methods 0.000 description 1
- 230000015843 photosynthesis, light reaction Effects 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000004537 pulping Methods 0.000 description 1
- 230000001835 salubrious effect Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 238000004513 sizing Methods 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- CXVGEDCSTKKODG-UHFFFAOYSA-N sulisobenzone Chemical compound C1=C(S(O)(=O)=O)C(OC)=CC(O)=C1C(=O)C1=CC=CC=C1 CXVGEDCSTKKODG-UHFFFAOYSA-N 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 239000010875 treated wood Substances 0.000 description 1
- WGKLOLBTFWFKOD-UHFFFAOYSA-N tris(2-nonylphenyl) phosphite Chemical compound CCCCCCCCCC1=CC=CC=C1OP(OC=1C(=CC=CC=1)CCCCCCCCC)OC1=CC=CC=C1CCCCCCCCC WGKLOLBTFWFKOD-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 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
- D21C9/00—After-treatment of cellulose pulp, e.g. of wood pulp, or cotton linters ; Treatment of dilute or dewatered pulp or process improvement taking place after obtaining the raw cellulosic material and not provided for elsewhere
- D21C9/001—Modification of pulp properties
- D21C9/002—Modification of pulp properties by chemical means; preparation of dewatered pulp, e.g. in sheet or bulk form, containing special additives
- D21C9/005—Modification of pulp properties by chemical means; preparation of dewatered pulp, e.g. in sheet or bulk form, containing special additives organic compounds
-
- D—TEXTILES; PAPER
- D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
- D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
- D21H21/00—Non-fibrous material added to the pulp, characterised by its function, form or properties; Paper-impregnating or coating material, characterised by its function, form or properties
- D21H21/14—Non-fibrous material added to the pulp, characterised by its function, form or properties; Paper-impregnating or coating material, characterised by its function, form or properties characterised by function or properties in or on the paper
- D21H21/143—Agents preventing ageing of paper, e.g. radiation absorbing substances
-
- D—TEXTILES; PAPER
- D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
- D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
- D21H17/00—Non-fibrous material added to the pulp, characterised by its constitution; Paper-impregnating material characterised by its constitution
- D21H17/03—Non-macromolecular organic compounds
- D21H17/05—Non-macromolecular organic compounds containing elements other than carbon and hydrogen only
- D21H17/07—Nitrogen-containing compounds
Definitions
- the instant invention pertains to a method for preventing the loss of brightness and for enhancing resistance to yellowing in pulp or paper, particularly pulp or paper which still contains lignin, by the addition of N,N-dialkylhydroxylamines, an ester, amide or thio substituted N,N-dialkylhydroxylamine or N,N-dibenzylhydroxylamine, or their salts and other coadditives.
- High-yield and ultra-high yield wood pulps undergo rapid light-induced discoloration, particularly when they are exposed to near ultraviolet light (wave lengths 300-400 nm) in indoor fluorescent light and daylight. This characteristic restricts their use to short-life, low- value paper products.
- High-yield and ultra-high yield wood pulps can be bleached to a high level of whiteness. If this whiteness could be stabilized against discoloration, these bleached high-yield pulps could displace significant amounts of more expensive fully-bleached, low- yield chemical pulps.
- Phenoxy radicals are the key intermediates in the reaction mechanism.
- Several light-induced reactions have been proposed to account for their formation such as cleavage of the aryl ether bond of phenacyl aryl ether groups, or breakdown of ketyl radicals formed from saturated aryl-glycerol ⁇ -aryl ether structures in lignin.
- the phenoxy radicals are oxidized by other oxygen-centered radicals (alkoxy and perhydroxy) to form yellow chromophores.
- UV absorbers and hydrogen donor agents such as thiols, ascorbic acid, etc. help prevent the photoinduced discoloration of hydrogen peroxide bleached wood pulp, but that chain breakers such as hindered phenols and hindered amines (having >N-H or >N-CH 2 - moieties) had no or even a detrimental effect on preventing photoinduced discoloration.
- thermomechanical (TMP) and chemithermomechical (CTMP) pulps summarizes the state of the art in the thermal and light-induced yellowing of lignin-containing pulps such as thermomechanical (TMP) and chemithermomechical (CTMP) pulps, showing the seriousness of these undesirable effects discusses generally the then current prior art methods used to attack this problem.
- TMP thermomechanical
- CMP chemithermomechical
- WO 99/05108 describes a potential solution where the use of selected hindered amine nitroxides, hindered amine hydroxylamines or their salts in combination with selected UV absorbers and metal chelating agents is seen to prevent loss of brightness and to enhance resistance to yellowing in pulp or paper still containing lignin.
- Canadian Patent Application No. 2,164,394 and WO 97/36041 teach a multi- component system for modifying, degrading or bleaching lignin-containing materials.
- This system includes an oxidation catalyst as an essential component.
- the catalysts are selected enzymes such as oxidoreductases of classes 1 J J to 1.97.
- the system also includes a number of mediators which inter alia include lower N,N-dialkylhydroxylamines and N,N- dibenzylhydroxylamine.
- the instant invention describes another approach to this important problem where the use of N.N-dialkylhydroxylamine, an ester, amide or thio substituted N,N-dialkylhydroxyl- amine or N,N-dibenzylhydroxylamine or their salts in combination with selected coadditives also prevents the loss of brightness and enhances resistance to yellowing in pulp or paper, especially pulp or paper still containing lignin.
- the ester, amide or thio substituted N,N- dialkylhydroxylamines are described in United States Patent Nos. 4,612,393; 4,720,517 and 5,019,285.
- N,N-dialkylhydroxylamines, derivatives thereof or N,N-dibenzylhydroxyl- amine to pulp or paper either alone or in combinations with UV absorbers, metal chelating agents, fluorescent whitening agents and/or stabilizing polymers effectively achieves a distinctly improved light and thermal stability.
- Addition to a kraft pulp or paper, which may still contain traces of lignin leads to a distinct improvement of the light and thermal stability.
- N,N-dialkylhydroxylamines, derivatives thereof or N,N-dibenzylhydroxyl- amine to high-yield pulp or paper which still contain lignin either alone or in combinations with UV absorbers, metal chelating agents, fluorescent whitening agents and/or stabilizing polymers effectively achieves light and thermal stability which is similar to that found in papers made from kraft pulps.
- Hydroxylamines are known to be efficient free radical traps and may limit the production of o-quinones; UV absorbers limit photochemistry in the underlying substrate to which they are applied, and ultimately reduce the production of free radicals. UV absorbers and hydroxylamines are each effective at stemming some of the free radical chemistry leading to paper yellowing when used singly. However, when they are used together, hydroxylamines and UV absorbers can act synergistically to effectively stop photochemical yellowing of lignin containing papers.
- the hydroxylamines show enhanced inhibiting activity when combined with a metal chelating agent such diethylenetriaminepentaacetic acid or citric acid, or polymeric inhibitors such as polyethylene glycol. More particularly, the instant invention pertains to a composition having enhanced resistance to yellowing which comprises
- R T and R 2 are independently alkyl of 1 to 18 carbon atoms, alkyl of 1 to 18 carbon atoms substituted by a hydroxyl group; or benzyl;
- T, and T 2 are independently alkyl of 1 to 4 carbon atoms, phenyl, 3,5-di-tert-butyl-4- hydroxyphenyl, benzyl or -CH 2 COOH;
- ET and E 2 are independently -OE 3 , -NHE 3 or -NE 3 E 4 where E 3 and E 4 are independently hydrogen, alkyl of 1 to 4 carbon atoms or said alkyl substituted by one hydroxyl group; or
- X is an inorganic or organic anion, and the total charge of cations h is equal to the total charge of anions j.
- X is phosphate, phosphonate, carbonate, bicarbonate, nitrate, chloride, bromide, bisulfite, sulfite, bisulfate, sulfate, borate, formate, acetate, benzoate, citrate, oxalate, tartrate.
- acrylate polyacrylate, fumarate, maleate, itaconate, glycolate, gluconate, malate, mandelate, tiglate, ascorbate, polymethacrylate, a carboxylate of nitrilotriacetic acid, hydroxyethylethylenediaminetriacetic acid, ethylenediaminetetraacetic acid or of diethylene- triaminepentaacetic acid, a diethylenediaminetetraacetic acid or of diethylenetriaminepenta- acetic acid, an alkylsulfonate or an arylsulfonate.
- the hydroxylamine is N,N-dimethylhydroxylamine, N,N-diethylhydroxyl- amine, N,N-bis(2-hydroxypropyl)hydroxylamine, N,N-bis(3-hydroxypropyl)hydroxylamine, N,N-dioctadecylhydroxylamine, the N,N-dialkylhydroxylamine product made by the direct oxidation of N,N-di(hydrogenated tallow)amine, N,N-dibenzylhydroxylamine, N,N-bis(2- carboxyethyl)hydroxylamine or N,N-bis(benzylthiomethyl)hydroxylamine.
- the hydroxylamine is N,N-diethylhydroxylamine, N,N-bis(2-hydroxy- propyl)hydroxylamine, N,N-bis(3-hydroxypropyl)hydroxylamine or N,N-dibenzylhydroxyl- amine; most especially N,N-diethylhydroxylamine or its citric acid salt.
- salts of these hydroxylamines are also beneficial in producing the increase in brightness and the resistance to yellowing in pulp or paper, especially when still containing lignin.
- the effective stabilizing amounts of the hydroxylamine is 0.001 to 5% by weight based on the pulp or paper.
- the effective stabilizing amount is 0.005 to 4% by weight; preferably 0.01 to 4% by weight.
- the effective stabilizing amount of the coadditives is also 0.001 to 5% by weight based on the pulp or paper; preferably 0.005 to 3% by weight; most preferably 0.01 to 2% by weight.
- the instant compounds may additionally include an effective stabilizing amount of at least one stabilizer selected from the group consisting of the UV absorbers, the polymeric inhibitors, the sulfur containing inhibitors, the phosphorus containing compounds, the nitrones, the benzofuran-2-ones, fluorescent whitening agents, hindered amine hydroxylamines and salts thereof, hindered amine nitroxides and salts thereof, hindered amines and salts thereof and metal chelating agents.
- at least one stabilizer selected from the group consisting of the UV absorbers, the polymeric inhibitors, the sulfur containing inhibitors, the phosphorus containing compounds, the nitrones, the benzofuran-2-ones, fluorescent whitening agents, hindered amine hydroxylamines and salts thereof, hindered amine nitroxides and salts thereof, hindered amines and salts thereof and metal chelating agents.
- compositions which also include a UV absorber are especially preferred.
- the UV absorber is selected from group consisting of the benzotriazoles, the s-triazines, the benzophenones, the ⁇ -cyanoacrylates, the oxanilides, the benzoxazinones, the benzoates and the ⁇ -alkyl cinnamates.
- the UV absorber is a benzotriazole, an s-triazine or a benzophenone, most especially a benzotriazole UV absorber or benzophenone UV absorber.
- Typical and useful UV absorbers are, for example,
- compositions which additionally contain a polymeric inhibitor; preferably poly(ethylene glycol), polypropylene glycol), poly(butylene glycol) or poly(vinyl pyrrolidone).
- a polymeric inhibitor preferably poly(ethylene glycol), polypropylene glycol), poly(butylene glycol) or poly(vinyl pyrrolidone).
- compositions are those wherein the additional stabilizer is a sulfur containing inhibitor; preferably polyethylene glycol dithiolacetate, polypropylene glycol dithiolacetate, polybutylene glycol dithioacetate, 1 -thioglycerol, 2-mercaptoethyl ether, 2,2'thiodiethanol, 2,2'-dithiodiethanol, 2,2'oxydiethanethiol, ethylene glycol bisthioglycolate, 3-mercapto-1 ,2-propanediol, 2-(2-methoxyethoxy)-ethanethiol, glycol dimercaptoacetate, 3,3'-dithiopropionic acid, polyethylene glycol dithiol, polypropylene glycol dithiol, polybutylene glycol dithiol or ethylene glycol bis(mercaptoacetate).
- the additional stabilizer is a sulfur containing inhibitor
- compositions are those wherein the additional stabilizer is a phosphorus containing compound; preferably tris(2,4-di-tert-butylphenyl) phosphite, 2,2',2"- nitrilo[triethyl-tris(3,3',5,5'-tetra-tert-butyl-1 J'-biphenyl-2,2'-diyl) phosphite], bis(2,4-di-tert- butyl-6-methylphenyl) ethyl phosphite, sodium hydroxymethyl phosphinate, tetrakis(2,4-di- butylphenyl) 4,4'-biphenylenediphosphonite, tris(nonylphenyl) phosphite, bis(2,4-di-tert-butyl- phenyl) pentaerythrityl diphosphite, 2,2'-ethyliden
- compositions are those wherein the additional stabilizer is a benzo- furan-2-one; preferably 5,7-di-tert-butyl-3-(3,4-dimethylphenyl)-2H-benzofuran-2-one.
- compositions wherein the additional stabilizer is a metal chelating agent; preferably citric acid, keto acids, gluconates, heptagluconates, phosphates, phosphonates and aminocarboxylic acid chelates, such as ethylenediaminetetraacetic acid (EDTA), diethylenetriaminepentaacetic acid (DTPA), hydroxyethylethlenediaminetriacetic acid (HEDTA), nitrilotriacetic acid (NTA) and diethylenetriaminepentamethylenephosphonic acid (DTPMPA).
- EDTA ethylenediaminetetraacetic acid
- DTPA diethylenetriaminepentaacetic acid
- HEDTA hydroxyethylethlenediaminetriacetic acid
- NTA nitrilotriacetic acid
- DTPMPA diethylenetriaminepentamethylenephosphonic acid
- compositions contain a mixture of additional stabilizers such as a mixture of a UV absorber and polymeric inhibitor; or a mixture of a UV absorber and a sulfur containing compound; or a mixture of a UV absorber and a phosphorus containing compound; or a mixture of a UV absorber and a metal chelating agent; or a mixture of a polymeric inhibitor and a sulfur containing compound; or a mixture of a polymeric inhibitor and a phosphorus containing compound; or a mixture of a sulfur containing compound and a phosphorus containing compound; or a mixture of a UV absorber, a polymeric inhibitor and a sulfur containing compound; or a mixture of a UV absorber, a polymeric inhibitor and a phosphorus containing compound; or a mixture of a UV absorber, a polymeric inhibitor, a sulfur containing compound; or a mixture of a UV absorber, a polymeric inhibitor and a phosphorus containing compound; or a mixture of a UV absorber,
- compositions are those wherein the additional stabilizer is a mixture of a hindered amine hydroxylamine or hindered amine hydroxylamine salt with at least one other stabilizer selected from the group consisting of the UV absorbers, the polymeric inhibitors, the sulfur containing inhibitors, the phosphorus containing compounds, fluorescent whitening agents (optical brighteners), metal chelating agents and hindered amine nitroxides and salts thereof.
- the additional stabilizer is a mixture of a hindered amine hydroxylamine or hindered amine hydroxylamine salt with at least one other stabilizer selected from the group consisting of the UV absorbers, the polymeric inhibitors, the sulfur containing inhibitors, the phosphorus containing compounds, fluorescent whitening agents (optical brighteners), metal chelating agents and hindered amine nitroxides and salts thereof.
- compositions wherein the additional stabilizer is a mixture of a UV absorber, a polymeric inhibitor and a sulfur containing compound; or a UV absorber, a polymeric inhibitor and a phosphorus containing compound; or a UV absorber, a polymeric inhibitor and a metal chelating agent; or a UV absorber, a polymeric inhibitor, a sulfur containing compound and a phosphorus containing compound; or a UV absorber and a hindered amine nitroxide; or a UV absorber and a hindered amine hydroxylamine; or a UV absorber and a hindered amine hydroxylamine salt.
- (Sterically) hindered amine nitroxides, hydroxylamines or hydroxylamine salts are mainly the compounds disclosed in WO 99/05108 (see formulae A to EE and A* to EE * therein, especially compounds (a) to (mm)).
- compositions wherein the additional stabilizer is a mixture of a hindered amine hydroxylamine with at least one optical brightener such as 2,2'-[(1 ,1 '- diphenyl)-4,4'-diyl-1 ,2-ethenediyl]bis-benzenesuifonic, disodium salt ⁇ or bis[4,4'-(2- stilbenesulfonic acid)], disodium salt ⁇ which is TINOPAL SK (Ciba Specialty Chemicals).
- optical brightener such as 2,2'-[(1 ,1 '- diphenyl)-4,4'-diyl-1 ,2-ethenediyl]bis-benzenesuifonic, disodium salt ⁇ or bis[4,4'-(2- stilbenesulfonic acid)], disodium salt ⁇ which is TINOPAL SK (Ciba Specialty Chemicals).
- compositions are those wherein the compound of formula I, II, III, IA, IIA or IIIA is of low molecular weight or contains hydrophilic moieties or is both of low molecular weight and contains hydrophilic moieties.
- the instant invention also pertains to a process for preventing the loss of brightness and for enhancing resistance to yellowing of a pulp or paper, particularly a chemimechanical or thermomechanical pulp or paper which still contain lignin, or a chemical pulp or paper or kraft pulp or paper which still contains traces of lignin, which comprises
- the instant inhibitor additive system can be added to pulp or paper at a number of places during the manufacturing or processing operations. These include
- the precise location where the stabilizer additives should be added will depend on the specific equipment involved, the exact process conditions being used and the like. In some cases, the additives may be added at one or more locations for most effectiveness.
- stabilizer or other coadditives are not themselves “water-soluble", they may be dispersed or emulsified by standard methods prior to application. Alternatively, the stabilizer and/or coadditives may be formulated into a paper sizing or paper coating formulation.
- All additives are applied by syringe-injecting the appropriate weight % of additive combination in either an aqueous solution when the additive is water soluble, or a solution in 1 :1 ethanol/dioxane, onto bleached thermomechanical pulp (BTMP) or chemical (kraft) pulp brightness squares (4 cm x 4cm). The clamped sheets are allowed to air dry for one day.
- BTMP bleached thermomechanical pulp
- chemical (kraft) pulp brightness squares (4 cm x 4cm).
- the brightness of the handsheets is recorded before and after treatment by light exposure under controled intensity conditions.
- Accelerated testing is carried out by subjecting the treated sheets to accelerated light induced yellowing in a fan-cooled light box containing eight fluorescent lamps with a spectral maximum output at 5700 A with a total output approximately 43 times greater than normal office fluorescent lamps.
- the lamps are about ten inches away from the handsheets being illuminated.
- Ambient testing is carried out by placing the treated handsheets on a desk under normal cool-white fluorescent office lights at a nominal distance of six feet. ln both cases, ISO brightness is tracked as a function of photolysis time and converted to post color number (PC number) in the usual manner.
- PC number post color number
- Post color (PC) number is defined as follows:
- k and s are the absorption and scattering coefficients, respectively, and R in , is the value of ISO brightness.
- untreated BTMP handsheets When, using the ambient test conditions, untreated BTMP handsheets are compared to Kraft handsheets after 60 days, the BTMP handsheets have a PC number which is about 10 while the Kraft paper has a PC number which is about 0.39. The Kraft handsheets are clearly less yellow than untreated BTMP handsheets after exposure to ambient light.
- the incident light flux for the accelerated yellowing experiments is 43 times greater than normal office fluorescent lamps as measured by the A. W. Speery SLM- 110 digital light power meter.
- the brightness of the handsheets is tracked and compared to that of untreated sheets exposed in the same manner.
- the treated sheets exhibit significant resistance to yellowing as is seen below. Materials Used in the Examples
- Compound A is N,N-diethylhydroxylamine.
- Compound B is N,N-dibenzylhydroxyiamine.
- Compound C is N,N-dioctadecylhydroxylamine.
- Compound D is the N,N-dialkylhydroxylamine product made by the direct oxidation of N,N- di(hydrogenated tallow)amine.
- Compound E is tris(N,N-diethylhydroxylammonium) citrate.
- PEO is poly(ethylene glycol) of molecular weight 300.
- TINUVIN ⁇ 328 (Ciba) is 2-(2-hydroxy-3,5-di-tert-amylphenyl)-2H-benzotriazole.
- TINOPAL ® SK (Ciba) is 2,2'-[(1 ,r-diphenyl)-4,4'-diyl-1 ,2-ethenediylJ)is-benzenesulfonic, disodium salt ⁇ or bis[4,4'-(2-stilbenesulfonic acid)], disodium salt ⁇ .
- CIBAFAST ® W (Ciba) is 3-(2H-benzotriazol-2-yl)-4-hydroxy-5-sec-butylbenzenesulfonic acid, sodium salt.
- Compound F is N,N-bis(2-carboxyethyl)hydroxylamine.
- Compound G is N,N-bis(benzylthiomethyl)hydroxylamine.
- a BTMP sheet is treated with 1.0% by weight of N,N-diethylhydroxylamine (Compound A) and exposed to accelerated aging as described above.
- the treated sheet in exhibits a substantial inhibition of yellowing compared to the untreated control sheet as seen by inspection of the PC numbers given in the table below. Lower PC numbers indicate less color.
- a BTMP sheet is treated with 0.3% by weight of Compound B and 2.0% by weight of poly(ethylene glycol), molecular weight 300 (PEO). Again, the treated sheet exhibits an excellent resistance to yellowing as compared to the untreated control sheet.
- PEO poly(ethylene glycol), molecular weight 300
- a BTMP sheet is treated with 0.3% by weight of Compound C and 1.0% by weight of 2-(2-hydroxy-3,5-di-tert-amylphenyl)-2H-benzotriazole (TINUVIN ® 328, Ciba).
- the treated sheet shows surprisingly excellent resistance to yellowing especially in contrast to the untreated control sheet.
- a BTMP sheet is treated with 0.6% by weight of Compound D, 2.0% by weight of poly(ethylene glycol), molecular weight 300 (PEO), and 1.0% by weight of 2-(2-hydroxy-3,5- di-tert-amylphenyl)-2H-benzotriazole (TINUVIN ® 328, Ciba).
- the treated sheet shows extraordinary resistance to yellowing especially in contrast to the untreated control sheet.
- a BTMP sheet is treated with 0.3% by weight of Compound A and 1.0% by weight of TINOPAL ® SK. Again, the treated sheet exhibits an excellent resistance to yellowing as compared to the untreated control sheet.
- a BTMP sheet is treated with 0.3% by weight of Compound B and 1.0% by weight of CIBAFAST ® W.
- the treated sheet shows surprisingly excellent resistance to yellowing especially in contrast to the untreated control sheet.
- a BTMP sheet is treated with 0.33% and with 0.66% by weight of N,N-diethylhydroxyl- amine (Compound A) and 0.5% by weight of CIBAFAST ® W and then exposed to accelerated aging as described above.
- the treated sheet exhibits a substantial inhibition of yellowing compared to the untreated control sheet as seen by inspection of the PC numbers given in the table below. Lower PC numbers indicate less color.
- a BTMP sheet is treated with 0.33% and with 0.66% by weight of tris(N,N-diethyl- hydroxylammonium) citrate (Compound E) and 0.5% by weight of CIBAFAST ® W and then exposed to accelerated aging as described above.
- the treated sheet exhibits a substantial inhibition of yellowing compared to the untreated control sheet as seen by inspection of the PC numbers given in the table below. Lower PC numbers indicate less color.
- a BTMP sheet is treated with 1.0% by weight of N,N-bis(2-carboxyethyi)hydroxylamine (Compound F) and 1.0% by weight of CIBAFAST ® W and then exposed to accelerated aging as described above.
- the treated sheet exhibits a substantial inhibition of yellowing compared to the untreated control sheet.
- a BTMP sheet is treated with 1.0% by weight of N,N-bis(benzylthiomethyl)hydroxyl- amine (Compound G) and 1.0% by weight of CIBAFAST ® W and then exposed to accelerated aging as described above.
- the treated sheet exhibits a substantial inhibition of yellowing compared to the untreated control sheet.
- a kraft sheet is treated with 1.0% by weight of N,N-diethylhydroxylamine (Compound A) and exposed to accelerated aging as described above.
- the treated sheet in exhibits a substantial inhibition of yellowing compared to the untreated control sheet.
- a kraft sheet is treated with 0.3% by weight of Compound B and 2.0% by weight of poly(ethylene glycol), molecular weight 300 (PEO). Again, the treated sheet exhibits an excellent resistance to yellowing as compared to the untreated control sheet.
- PEO poly(ethylene glycol), molecular weight 300
- a kraft sheet is treated with 0.3% by weight of Compound C and 1.0% by weight of 2- (2-hydroxy-3,5-di-tert-amylphenyl)-2H-benzotriazole (TINUVIN® 328, Ciba).
- the treated sheet shows surprisingly excellent resistance to yellowing especially in contrast to the untreated control sheet.
- a kraft sheet is treated with 0.6% by weight of Compound D, 2.0% by weight of poly(ethylene glycol), molecular weight 300 (PEO), and 1.0% by weight of 2-(2-hydroxy-3,5- di-tert-amylphenyl)-2H-benzotriazole (TINUVIN® 328, Ciba).
- the treated sheet shows extraordinary resistance to yellowing especially in contrast to the untreated control sheet.
- a kraft sheet is treated with 0.3% by weight of Compound A and 1.0% by weight of TINOPAL ® SK. Again, the treated sheet exhibits an excellent resistance to yellowing as compared to the untreated control sheet.
- a kraft sheet is treated with 0.3% by weight of Compound B and 1.0% by weight of CIBAFAST ® W.
- the treated sheet shows surprisingly excellent resistance to yellowing especially in contrast to the untreated control sheet.
- a kraft sheet is treated with 0.33% and with 0.66% by weight of N,N-diethylhydroxyl- amine (Compound A) and 0.5% by weight of CIBAFAST ® W and then exposed to accelerated aging as described above.
- the treated sheet exhibits a substantial inhibition of yellowing compared to the untreated control sheet.
- a kraft sheet is treated with 0.33% and with 0.66% by weight of tris(N,N-diethyl- hydroxylammonium) citrate (Compound E) and 0.5% by weight of CIBAFAST® W and then exposed to accelerated aging as described above.
- the treated sheet exhibits a substantial inhibition of yellowing compared to the untreated control sheet.
- a kraft sheet is treated with 1.0% by weight of N,N-bis(2-carboxyethyl)hydroxylamine (Compound F) and 1.0% by weight of CIBAFAST® W and then exposed to accelerated aging as described above.
- the treated sheet exhibits a substantial inhibition of yellowing compared to the untreated control sheet.
- a kraft sheet is treated with 1.0% by weight of N,N-bis(benzylthiomethyl)hydroxylamine (Compound G) and 1.0% by weight of CIBAFAST® W and then exposed to accelerated aging as described above.
- the treated sheet exhibits a substantial inhibition of yellowing compared to the untreated control sheet.
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- Paper (AREA)
- Chemical And Physical Treatments For Wood And The Like (AREA)
- Anti-Oxidant Or Stabilizer Compositions (AREA)
Abstract
Description
Claims
Applications Claiming Priority (7)
Application Number | Priority Date | Filing Date | Title |
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US17701698A | 1998-10-22 | 1998-10-22 | |
US177016 | 1998-10-22 | ||
US11668899P | 1999-01-20 | 1999-01-20 | |
US234253 | 1999-01-20 | ||
US116688P | 1999-01-20 | ||
US09/234,253 US20020088574A1 (en) | 1998-10-22 | 1999-01-20 | Inhibition of pulp and paper yellowing using hydroxylamines and other coadditives |
PCT/EP1999/007594 WO2000024963A1 (en) | 1998-10-22 | 1999-10-11 | Inhibition of pulp and paper yellowing using hydroxylamines and other coadditives |
Publications (2)
Publication Number | Publication Date |
---|---|
EP1131483A1 true EP1131483A1 (en) | 2001-09-12 |
EP1131483B1 EP1131483B1 (en) | 2003-11-05 |
Family
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Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP99953767A Expired - Lifetime EP1131483B1 (en) | 1998-10-22 | 1999-10-11 | Inhibition of pulp and paper yellowing using hydroxylamines and other coadditives |
Country Status (10)
Country | Link |
---|---|
EP (1) | EP1131483B1 (en) |
JP (1) | JP2002528657A (en) |
CN (1) | CN1324419A (en) |
AT (1) | ATE253662T1 (en) |
AU (1) | AU754737B2 (en) |
BR (1) | BR9914721A (en) |
CA (1) | CA2346211A1 (en) |
DE (1) | DE69912633T2 (en) |
RU (1) | RU2222654C2 (en) |
WO (1) | WO2000024963A1 (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US9745700B2 (en) | 2008-06-20 | 2017-08-29 | International Paper Company | Composition and recording sheet with improved optical properties |
Families Citing this family (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
AU2001271720A1 (en) | 2000-07-05 | 2002-01-14 | Rosetta Inpharmatics, Inc. | Methods and compositions for determining gene function |
AU2003266346A1 (en) | 2002-09-11 | 2004-04-30 | Ciba, Specialty Chemicals Holding Inc. | Stabillization of organic materials |
WO2004056931A1 (en) * | 2002-12-20 | 2004-07-08 | Ciba Specialty Chemicals Holding Inc. | Ink-jet ink and recording material |
KR101279899B1 (en) * | 2003-10-30 | 2013-06-28 | 시바 홀딩 인코포레이티드 | Stabilized body care products, household products, textiles and fabrics |
WO2005042828A2 (en) * | 2003-11-03 | 2005-05-12 | Ciba Specialty Chemicals Holding Inc. | Stabilized body care products, household products, textiles and fabrics |
FI20031904A (en) * | 2003-12-23 | 2005-06-24 | Kemira Oyj | Process for modifying a lignocellulosic product |
CA2601507C (en) * | 2005-04-08 | 2013-09-03 | Nalco Company | Improved compositions and processes for paper production |
US8092649B2 (en) * | 2005-12-14 | 2012-01-10 | Nalco Company | Method of decreasing the rate of photoyellowing with thiocyanic acid |
CN101182693B (en) * | 2007-12-12 | 2010-06-02 | 中冶纸业银河有限公司 | Method capable of stabilizing paper stuff whiteness |
DE112012007224T5 (en) * | 2012-12-13 | 2015-10-22 | Abb Technology Ag | System and method for operation monitoring and / or diagnosis of a production line of an industrial plant |
FI127900B (en) * | 2014-05-27 | 2019-05-15 | Upm Kymmene Corp | A method for reducing phosphorus load in effluent from a pulp production process |
CN105155338A (en) * | 2015-09-10 | 2015-12-16 | 上海晶华胶粘新材料股份有限公司 | Anti-ultraviolet (UV) water-based paper impregnant and preparation method thereof |
CN105839431A (en) * | 2016-06-13 | 2016-08-10 | 东莞市博科纺织科技有限公司 | Anti-phenolic yellowing agent and preparation method thereof |
CN109440458A (en) * | 2018-10-08 | 2019-03-08 | 淮海工学院 | A kind of multi-functional softening agent and preparation method thereof |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3832277A (en) * | 1972-02-24 | 1974-08-27 | Fmc Corp | Hydroxylamine treated hemicellulose-containing regenerated cellulose product |
JPS5926464A (en) * | 1982-07-22 | 1984-02-10 | ユニチカ株式会社 | Packing material for polyamide fiber, etc. |
US4612393A (en) * | 1985-04-29 | 1986-09-16 | Ciba-Geigy Corporation | Bis(substituted thioalkyl)hydroxylamines and stabilized polyolefin compositions |
EP0717143A1 (en) * | 1994-12-16 | 1996-06-19 | Lignozym GmbH | Multicomponents system for modifying decomposing or bleaching of lignin or materials containing it or similar components and the way to use it |
-
1999
- 1999-10-11 JP JP2000578513A patent/JP2002528657A/en active Pending
- 1999-10-11 EP EP99953767A patent/EP1131483B1/en not_active Expired - Lifetime
- 1999-10-11 AT AT99953767T patent/ATE253662T1/en not_active IP Right Cessation
- 1999-10-11 CN CN99812516.4A patent/CN1324419A/en active Pending
- 1999-10-11 WO PCT/EP1999/007594 patent/WO2000024963A1/en not_active Application Discontinuation
- 1999-10-11 CA CA002346211A patent/CA2346211A1/en not_active Abandoned
- 1999-10-11 AU AU10346/00A patent/AU754737B2/en not_active Ceased
- 1999-10-11 RU RU2001113262/12A patent/RU2222654C2/en not_active IP Right Cessation
- 1999-10-11 DE DE69912633T patent/DE69912633T2/en not_active Expired - Fee Related
- 1999-10-11 BR BR9914721-1A patent/BR9914721A/en not_active IP Right Cessation
Non-Patent Citations (1)
Title |
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See references of WO0024963A1 * |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US9745700B2 (en) | 2008-06-20 | 2017-08-29 | International Paper Company | Composition and recording sheet with improved optical properties |
Also Published As
Publication number | Publication date |
---|---|
JP2002528657A (en) | 2002-09-03 |
EP1131483B1 (en) | 2003-11-05 |
DE69912633T2 (en) | 2004-09-23 |
DE69912633D1 (en) | 2003-12-11 |
BR9914721A (en) | 2001-07-10 |
CN1324419A (en) | 2001-11-28 |
ATE253662T1 (en) | 2003-11-15 |
AU754737B2 (en) | 2002-11-21 |
CA2346211A1 (en) | 2000-05-04 |
WO2000024963A1 (en) | 2000-05-04 |
RU2222654C2 (en) | 2004-01-27 |
AU1034600A (en) | 2000-05-15 |
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