GB2122660A - Improvements in or relating to organic compounds - Google Patents
Improvements in or relating to organic compounds Download PDFInfo
- Publication number
- GB2122660A GB2122660A GB08315573A GB8315573A GB2122660A GB 2122660 A GB2122660 A GB 2122660A GB 08315573 A GB08315573 A GB 08315573A GB 8315573 A GB8315573 A GB 8315573A GB 2122660 A GB2122660 A GB 2122660A
- Authority
- GB
- United Kingdom
- Prior art keywords
- formula
- compound
- hydrogen
- paper
- size
- 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
- 150000002894 organic compounds Chemical class 0.000 title description 2
- 230000003287 optical effect Effects 0.000 claims abstract description 17
- 125000002091 cationic group Chemical group 0.000 claims abstract description 10
- WASQWSOJHCZDFK-UHFFFAOYSA-N diketene Chemical compound C=C1CC(=O)O1 WASQWSOJHCZDFK-UHFFFAOYSA-N 0.000 claims abstract description 5
- 150000001875 compounds Chemical class 0.000 claims description 23
- 238000000034 method Methods 0.000 claims description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 239000001257 hydrogen Substances 0.000 claims description 16
- 229920002472 Starch Polymers 0.000 claims description 11
- 239000008107 starch Substances 0.000 claims description 11
- 235000019698 starch Nutrition 0.000 claims description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- -1 alkyl ketene dimer Chemical compound 0.000 claims description 7
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 4
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 claims description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical class [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 2
- 229910001413 alkali metal ion Inorganic materials 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 150000001768 cations Chemical group 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- 239000011230 binding agent Substances 0.000 abstract description 3
- 230000000171 quenching effect Effects 0.000 abstract description 2
- 238000010791 quenching Methods 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 7
- NGDLSKPZMOTRTR-OAPYJULQSA-N (4z)-4-heptadecylidene-3-hexadecyloxetan-2-one Chemical compound CCCCCCCCCCCCCCCC\C=C1/OC(=O)C1CCCCCCCCCCCCCCCC NGDLSKPZMOTRTR-OAPYJULQSA-N 0.000 description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- 230000002378 acidificating effect Effects 0.000 description 3
- 150000002431 hydrogen Chemical group 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 159000000000 sodium salts Chemical group 0.000 description 3
- 239000000945 filler Substances 0.000 description 2
- 239000013055 pulp slurry Substances 0.000 description 2
- 238000004513 sizing Methods 0.000 description 2
- TXVWTOBHDDIASC-UHFFFAOYSA-N 1,2-diphenylethene-1,2-diamine Chemical compound C=1C=CC=CC=1C(N)=C(N)C1=CC=CC=C1 TXVWTOBHDDIASC-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 229920001131 Pulp (paper) Polymers 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- CCGKOQOJPYTBIH-UHFFFAOYSA-N ethenone Chemical compound C=C=O CCGKOQOJPYTBIH-UHFFFAOYSA-N 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 150000002561 ketenes Chemical class 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- D21H21/30—Luminescent or fluorescent substances, e.g. for optical bleaching
-
- 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
- D21H17/17—Ketenes, e.g. ketene dimers
Landscapes
- Paper (AREA)
Abstract
Optical brighteners of formula I <IMAGE> where R, R1, R2, R3 and M are defined in the text, may be used to brighten paper sized with cationic promoted ketene dimer based sizes, without unacceptable quenching of their fluorescence. The brighteners of formula I are preferably applied together with a binder at the size press.
Description
SPECIFICATION
Improvements in or relating to organic compounds
This invention relates to the use of optical brighteners in a paper sizing system based on cationic promoted ketene dimers.
It is known to use optical brighteners in the manufacture of paper, and to apply such brighteners either by adding them to the pulp slurry or by sizing the paper sheet in a size press with a size containing the brightener. Alternatively the size may be added to the pulp as a dispersion of a thermosettable resin, and the brightener subsequently added in a size press together with a binder such as starch.
Traditional paper sizes are generally acidic, which has certain disadvantages. For example, it is not possible to use chalk as a filler if acidic sizes are used, although chalk is cheaper than china clay and can be used at higher loading: More recently, ketene dimer sizes have become commercially available, for example those sold under the trade mark Aquapel by Hercules, Inc. and described in US
Patent 3 968 31 7. These have the advantage that they can be applied at neutral pH (pH 6-8) and allow the use of chalk as a filler.In order to obtain rapid curing of the ketene dimer size, however, it is generally necessary to use a highly cationic promoter, for example reaction products of dicyanodiamide and formaldehyde, and when this type of compound is present it is found that the fluorescence of any optical brighteners which are present may be quenched and their effect reduced. This quenching effect is found even when the size and optical brightener are applied in separate operations.
It has now been found that certain known optical brighteners give a fluorescence on paper which is not quenched, or quenched only to an acceptable degree, by strongly cationic alkyl ketene dimerbased sizes.
Accordingly, the present invention provides a process for the production of optically brightened paper sized with an alkyl ketene dimer based size containing a cationic promoter comprising the step of applying to the pulp or to the paper sheet, before, simultaneously with, or after the step of applying a ketene dimer-based size, an optical brightener of formula I
in which each R, each R1, each R2and each R3 independently is hydrogen, R4O)H -R4CONH2 or- R4CN; preferably hydrogen,AR40)nH or-R4CONH2; more preferably hydrogen or -CR,O),H, where
R4 is C26 alkylene and n is 1 or 2
provided that the eight R, R1, R2 and R3 groups may not all be hydrogen and
M is hydrogen or a cation, preferably hydrogen, an alkali metal ion, particularly sodium, or a substituted ammonium ion, for example
By the term "cationic promoter" is included any compound which in an aqueous system at pH 6-8 contains at least one amine salt or quaternary ammonium group per molecule. Preferably the promoter is polymeric and contains a plurality of such groups per molecule. Particularly preferred promoters are condensation polymers of dicyanodiamide and formaldehyde.
In the compounds of formula I, when both groups Rand both groups R2 are-CH2CH2OH, then the four groups R, and R3 are preferably not all hydrogen.
Preferably the molecule is symmetrical, so that RRN- is identical to -NR2R2 and R1R1N- is identical to -NR3R3. R4 is preferably R4 where R4 is
or-CH2-CH2, more preferably-CH2-CH2-, and n is preferably 1. Preferably each of the groups -NRR,-NR1R1,-NR2R2and-NR3R3 contains at least one group+R40)nH A preferred group of compounds are those of formula I'
in which each of R', R", R; and R'1' are independently H or -CH2CH2OH, with the proviso that all four groups may not be hydrogen, and
M is as defined above.
It is preferred that when R' and R" are both -CH2CH2OH, then Rt and R'1' are not both hydrogen.
Particularly preferred are the compounds of formula la and Ib, especially Ib:
Compounds of formula I are known, for example from British patent 624 052, or may be prepared from known starting materials by analogy with methods disclosed therein. The compound of formula la is that of Example 1 of British Patent 624 052.
The compounds of formula I are applied by known methods for example The compounds of formula I may be added to the pulp slurry (stock) in quantities of between 0.1 and 10 g/kg dry weight of pulp. The alkyl ketene dimer size system may be also added to the stock and the paper made in the normal way, the size being cured during the drying step. Alternatively the size may be applied to the brightened paper sheet in a subsequent operation, using a size press.
Preferably, however, the compounds of formula I are applied to ready-formed paper sheet on a size press. For this operation an aqueous solution of from 0.2 g/l to 4 g/l may be used, applied at a pickup of from 150 g to 500 g/kg dry weight of paper. The paper may already contain the size system, in which case the compound of formula I may be applied together with a binder such as starch, suitably from 60 g to 120 g starch per litre of solution.
Alternatively the compound of formula I and the size system may be applied simultaneously on a size press. The preferred method of application, however, is application of the compound of formula I together with starch at the size press to paper pre-treated with the alkyl ketene dimer size, as described above.
The compound of formula I may be used in conjunction with one or more other optical brighteners; for example an optical brightener other than one of formula I may be added to the stock and the compound of formula I added together with starch at the size press.
An optical brightener other than one of formula I will generally be quenched to an appreciable extent by the size system, and it will be necessary to use more of such a brightener than would be the case if an acidic size were used. Nevertheless it may be desirable to use a combination of brighteners rather than a single brightener of formula
The resulting paper has good brightness properties determined by reflectance measurements using a Carl Zeiss Elrepho Reflectometer with a Xenon lamp and a Tristimulus FMZ/L filter.
The following Examples illustrate the invention.
Example 1
200 Grams of an aqueous slurry of bleached paper pulp (equivalent to 4 grams of dried paper) is stirred at room temperature in a 1 litre glass beaker fitted with a stainless steel paddle. A solution of 8 milligrams of brightener of formula la in sodium salt form in 20 milliiitres of water is added and the mixture stirred for 1 minute. 80 milligrams of 'Aquapel 2 Liquid' are added, the mixture stirred for 2 minutes and then filtered using a rectangular wire mesh. The formed paper sheet is pressed dry
between filter paper and a woollen felt and finally dried between filter paper on a heated drum at 80- 900 C.
The dried paper has a distinct brightness, which is not evident in a similar paper without the brightener.
Example 2
50 Milligrams of the brightener of formula Ib in sodium salt form is dissolved in 100 ml of 8%
W/V starch solution and heated to 45-550C. This solution is then poured between two moving rollers through which a sheet of paper is pre-treated with 2% (calculated on weight of dry paper) Aquapel 2
Liquid is passed, the paper thus being coated with the brightener/starch solution. The damp paper is then dried between filter paper on a heated drum at 8O-900C.
The dried paper has a distinct brightness which is not evident in a similar paper made without addition of brightener.
Example 3
A paper having a low to moderate degree of brightness is prepared on a Fourdrinier machine operating at a production rate of 1 5 tons/hour from a stock containing 2% (based on dry weight of pulp) of Aquapel 2 Liquid. To the thick stock is added 36 1/hour a 30% wt. solution of a diaminostilbene type optical brightener the fluorescence of which is quenched to the extent of approx. 30%
Aquapel 2, and at the size press is added 400 1/hr of a brightener/starch composition containing 1% wt. of the compound of formula Ib (in sodium salt form). Good results are obtained.
Example 4
Example 3 is repeated, using 138 1/hr of the same optical brightener solution in the stock and 950 1/hr of the same brightener/starch composition at the size press. A paper of higher brightness is obtained.
Claims (14)
1. A process for the production of optically brightened paper sized with an alkyl ketene dimer based size containing a cationic promoter comprising the step of applying to the pulp or to the paper sheet, before, simultaneously with, or after the step of applying a ketene dimer-based size, an optical brightener of formula I
in which each R, each R1, each R2 and each R3 independently is hydrogen, R4O)H -R4CONH2or - R4CN; where R4 is C26 alkylene and n is 1 or 2
provided that the eight R, R1, R2 and R3 groups may not all be hydrogen, and
M is hydrogen or a cation.
2. A process as claimed in Claim 1 in which the cationic promoter is a polymeric reaction product of dicyanodiamide and formaldehyde.
3. A process as claimed in Claim 1 or Claim 2 in which, in the compound of formula I, each R, R,, each R2 and each R3 independently is hydrogen,+R40)nH or-R4CONH2.
4. A process as claimed in Claim 3 in which, in the compound of formula i, each Reach R1, each
R2 and each R3 independently is hydrogen or -CR,O),H.
5. A process as claimed in any one of the preceding claims in which, in the compound of formula
or -CH2-CH2- and n=1.
6. A process as claimed in Claim 5 in which the optical brightener is of formula I'
in which each R', R", R; and R', are independently H or -CH2CH2OH, with the proviso that all four groups may not be hydrogen, and M is as defined in Claim 1.
7. A process as claimed in Claim 6 in which the optical brightener is of formula la
in which M is as defined in Claim 1.
8. A process as claimed in Claim 6 in which the optical brightener is of formula Ib
in which M is as defined in Claim 1.
9. A process as claimed in any one of the preceding claims in which, in the compound of formula
I, M is hydrogen, an alkali metal ion or a substituted ammonium ion.
10. A process as claimed in any one of the preceding claims in which the compound of formula I is applied to ready-formed paper sheet on a size press.
1 A process as claimed in any one of the preceding claims in which the compound of formula I is applied together with starch at the size press to paper pre-treated with the alkyl ketene dimer based size containing a cationic promoter.
12. A process as claimed in Claim 11 in which there is applied at the size press, at a pick up of 1 50 g to 500 g/kg dry weight of paper, an aqueous composition containing 0.2 4.0 g of compound of formula I and 60-120 g starch per litre.
1 3. A process according to Claim 1 as described in any one of the Examples.
14. Paper sized with a cationic promoted alkyl ketene dimer based size and brightened with an optical brightener of formula I, stated in Claim 1.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8216697 | 1982-06-09 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| GB8315573D0 GB8315573D0 (en) | 1983-07-13 |
| GB2122660A true GB2122660A (en) | 1984-01-18 |
| GB2122660B GB2122660B (en) | 1985-12-18 |
Family
ID=10530905
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB08315573A Expired GB2122660B (en) | 1982-06-09 | 1983-06-07 | Improvements in or relating to organic compounds |
Country Status (6)
| Country | Link |
|---|---|
| JP (1) | JPS5915598A (en) |
| BR (1) | BR8303043A (en) |
| DE (1) | DE3319569A1 (en) |
| FR (1) | FR2528461A1 (en) |
| GB (1) | GB2122660B (en) |
| IT (1) | IT1173720B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4964951A (en) * | 1987-05-29 | 1990-10-23 | Security Tag Systems, Inc. | Process for making secure paper product |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2608096B2 (en) * | 1988-04-18 | 1997-05-07 | 三菱製紙株式会社 | Photographic support |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1147964A (en) * | 1966-05-03 | 1969-04-10 | Sandoz Ltd | Optically brightening textiles of synthetic polyamides |
| GB1337583A (en) * | 1970-03-24 | 1973-11-14 | Ciba Geigy Uk Ltd | Treatment of optical brightening agents |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3025242A (en) * | 1961-03-20 | 1962-03-13 | Du Pont | Whitening agent composition and process for its manufacture |
| DE1283083B (en) * | 1961-12-08 | 1968-11-14 | Bayer Ag | Process for making lightened paper |
| GB1373788A (en) * | 1971-10-20 | 1974-11-13 | Hercules Powder Co Ltd | Sizing method and composition for use therein |
| DE2715864A1 (en) * | 1976-04-14 | 1977-10-27 | Ciba Geigy Ag | PROCEDURE FOR OPTICAL LIGHTENING PAPER |
-
1983
- 1983-05-30 DE DE19833319569 patent/DE3319569A1/en not_active Withdrawn
- 1983-06-03 FR FR8309381A patent/FR2528461A1/en active Granted
- 1983-06-07 GB GB08315573A patent/GB2122660B/en not_active Expired
- 1983-06-08 BR BR8303043A patent/BR8303043A/en unknown
- 1983-06-08 JP JP58101054A patent/JPS5915598A/en active Pending
- 1983-06-09 IT IT48464/83A patent/IT1173720B/en active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1147964A (en) * | 1966-05-03 | 1969-04-10 | Sandoz Ltd | Optically brightening textiles of synthetic polyamides |
| GB1337583A (en) * | 1970-03-24 | 1973-11-14 | Ciba Geigy Uk Ltd | Treatment of optical brightening agents |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4964951A (en) * | 1987-05-29 | 1990-10-23 | Security Tag Systems, Inc. | Process for making secure paper product |
Also Published As
| Publication number | Publication date |
|---|---|
| GB2122660B (en) | 1985-12-18 |
| BR8303043A (en) | 1984-01-31 |
| IT8348464A0 (en) | 1983-06-09 |
| JPS5915598A (en) | 1984-01-26 |
| FR2528461B1 (en) | 1985-05-03 |
| DE3319569A1 (en) | 1983-12-15 |
| FR2528461A1 (en) | 1983-12-16 |
| GB8315573D0 (en) | 1983-07-13 |
| IT1173720B (en) | 1987-06-24 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PCNP | Patent ceased through non-payment of renewal fee |