CA1150914A - Amine-epichlorohydrin polymers for pitch control - Google Patents
Amine-epichlorohydrin polymers for pitch controlInfo
- Publication number
- CA1150914A CA1150914A CA000365778A CA365778A CA1150914A CA 1150914 A CA1150914 A CA 1150914A CA 000365778 A CA000365778 A CA 000365778A CA 365778 A CA365778 A CA 365778A CA 1150914 A CA1150914 A CA 1150914A
- Authority
- CA
- Canada
- Prior art keywords
- polyquaternary
- polymer
- pulps
- diepoxides
- epihalohydrins
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
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
- D21C9/08—Removal of fats, resins, pitch or waxes; Chemical or physical purification, i.e. refining, of crude cellulose by removing non-cellulosic contaminants, optionally combined with bleaching
- D21C9/086—Removal of fats, resins, pitch or waxes; Chemical or physical purification, i.e. refining, of crude cellulose by removing non-cellulosic contaminants, optionally combined with bleaching with organic compounds or compositions comprising organic compounds
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- Paper (AREA)
Abstract
ABSTRACT OF THE DISCLOSURE
A method of reducing the amount of colloidal pitch particles in aqueous pulps which comprises treating said pulps with a water-dispersible poly-quaternary polymer of essentially linear structure consisting essentially of the difunctional reaction product of a lower dialkylamine and a difunctional epoxy compound selected from the group consisting of epihalohydrins, diepoxides, percursors of epihalohydrins and diepoxides which under alkaline conditions are readily converted into the corresponding epoxy compounds, and mixtures thereof, said polyquaternary polymer containing repeating units of wherein R and R2 are individually selected from the group consisting of alkyl of 1 to 3 carbon atoms, and E is a residue obtained from said epoxy compound;
tic total amounts of reactants being substantially equimolar, the combination of which is such as to provide a polyquaternary compound which as a 37% aqueous solution, by weight, based on the cationic portion of said polyquaternary com-pound has a viscosity at 25°C. of at least 100 centistokes; and X represents an ion forming the anionic portion of said polyquaternary.
A method of reducing the amount of colloidal pitch particles in aqueous pulps which comprises treating said pulps with a water-dispersible poly-quaternary polymer of essentially linear structure consisting essentially of the difunctional reaction product of a lower dialkylamine and a difunctional epoxy compound selected from the group consisting of epihalohydrins, diepoxides, percursors of epihalohydrins and diepoxides which under alkaline conditions are readily converted into the corresponding epoxy compounds, and mixtures thereof, said polyquaternary polymer containing repeating units of wherein R and R2 are individually selected from the group consisting of alkyl of 1 to 3 carbon atoms, and E is a residue obtained from said epoxy compound;
tic total amounts of reactants being substantially equimolar, the combination of which is such as to provide a polyquaternary compound which as a 37% aqueous solution, by weight, based on the cationic portion of said polyquaternary com-pound has a viscosity at 25°C. of at least 100 centistokes; and X represents an ion forming the anionic portion of said polyquaternary.
Description
~lS1~314 The problem of pitch control in papermaking has previously been recognized. The pitch in the fibers of wood pulps is associated with naturally occurring lignin dispersing agents. Cooking and mechanical agitation which occur during the pulping by the sulfite process liberates pitch and these natural dispersing agents. But, as a result of the mechanical work on the fibers, the natural dispersing agents liberated along with the pitch are inadequate to keep the pitch from depositing on the equipment employed in beating, hydrating, re:fining, bleaching, and even on the wire used for forming the sheet. Because of the tendency o-f the pitch to agglomerate within the pulp suspension or cleposit on the surfaces of the wire or other equipment and then to break free in the form of part:iclos of considerable si~e, the pitch frequontly causes the formation of spots or holes in the sheet formed or may adhere to the wire or press rolls or drier rolls ancl cause toaring of the sheet. This results in occasional tearing of the sheet dur;ng -formation or in the production o-f sheets with numerous imperEectiolls. Among other consequences involvecl are thc e~pc?nse of cloanillg the I~ chinory Erequently cither with solvcnts or stcam, an(l thc loss O ~ prOdUCtiOII dUr:illg c 1 c;lll i llg ;IllCI dll r i llg r Cn l ;l (` i ng Ol)Cr;l t i OIl !; CIlUSc?Cl by hre:lkdown o-E the shoet.
:rn the art:.ic1c cl~titlc~ l'ar~:iclc (,onccntl.ltiol~ n In~l~ort;lnt I'aralneter in l'itcll l~oblcllls," I-y 1,.11. /~1 Ic~ll, wllicll apl~c.lrs in ~:he Iralls;lctio!l.s oE the Iechllical_~e~tioll ol` ~:llc (all;l-li;lll I'ull) and l'al)cl ~sso~i;ltioll ~or .]UIIC, 1977, :it is clolllollstl<l-tcd -LIl;lt thos~ woo(l pllll)s wllich C;lllSC l-itcll problellns contilir a hi~h concclltr.ltioll oE sllspclldcd col loid.ll l~i-tcll p;lrticle.s~ 'I'hc pitcll cleposit potcllti.ll of a pllll~ is shown to hc pl~oportioll.ll to thc concentration o-E collo-idal pitCII drol~lets.
I`his article shows tha-t it is possible to measure the pitch by micro-scopic obscrv.ltion the concentration of colloidally suspended pitch droplets in *~
~S~9~4 a blood eounting chamber known as a hemacytometer. This particular method is described by the author in this article as follows:
"A. Particle ~oncen~ration Determinations Each pulp sample is filtered through a rapid, coarse, filter paper ~Reeve Angel No. 202) to remove the fibres, and the concentration of colloidally sus-pended pitch droplets in the filtrate is counted in a hemacytometer with a microscope. . ."
It is known that certain water-soluble polymers are capable of acting as pitch dispersants whereby the pitch can be maintained in a colloidal state of subdivision without agglomeration of the particles occurring. It is further known that certain polytners and, in particular, low molecular weight water-soluble cationic polymers, will cause the pitch particles to become attached to the fibers. This removes the colloidal pitch particles Erom the whitew,lter and tends to prevent deposit formation from occurring.
The ~present invent;oll ;s pred~ic;lted ut)on the discovery of certia;ll cat;onie pulylllers whicll give superior collo;dill pitcl~ll;lrticle recluctioll ;n aqueous pulps.
~ IUS thi.s illv(i~llt:ioll pl'OVi(lCs .1 IllCthO(I oE l`CdUCillg the alllount Or col-]okl;ll pitcll l)atticles in a(lllC011S p~ )'; which COIIII)risCs I t'C;ltillg Sai.(l pllll)S with a watel~-d-ispersil)le polyqlt;l~erllary polylller ol essenti:llly line~lt structure Ct)ll-sisting ossellti;llly of tl~e d.ilullct.i.oll.ll rcact:ion prodllct of a lowcr dialky1<1.lll:i.tlc and a diEullctioll;ll epoxy coml)olllld sclcctcd from the grolll) consisting of ep-ihalo-hydrills, d;opoxides, percursors of epih;llollydrins and diepoxides which under alkaline conditions are readily converted into the corresponding epoxy conlpounds, and m;xtures thereof, said polyquaternary polymer containing repeating units of ~L~5~914 N - E ~
L 12 ¦.X
wherein R and R2 are individually selected from the group consisting of alkyl of 1 to 3 carbon atoms, and E is a residue obtained from said epoxy compound;
the total amounts of reactants being substantially equimolar, the combination of which is such as to provide a polyquaternary compound l~hich as a 37% aqueous solution, by weight, based on the cationic portion of said polyquaternary compound has a viscosity at 25C. o:f at least 100 centistokes; and X re-prescnts an ion :forming thc anion;c portion of said polyquaterllary.
~ pre:ferred speci.es o-f polymers of tllc type dcscribed above are thosc prepared by us:ing as thc rcactants epichlorollydrill and d:imetllylamine.
Polyquaterllary polymcrs of the typc described .~hove alld thcir metllod of preparation are dcscribed in lJnited Statcs 3,738,9~l5.
rl`he dosage Or acti.vc polymcri.c comllollcllt llSCd t(l trc;lt thc ;Iqllcous ~u:ll)s may -range :from as li.ttlc ;m~ ().l ul~ to ;IS mllcll ;IS I killogr;llll l)cr ton o~F
ulp bascd on dry fibc:r wc:i.gllt.
rO :il:lustr;ltc thc clfi(:lcy ol`l~ly illvcntioll, thc lollowillg is l~rc-SCI~tc~(l I)y w:ly ol CX;IIIII)`l C.
Tllc tcst mctlloll uscd corrcsl)(!lldc(l gcllcr;llly to th;lt dcsclibcd l~y
:rn the art:.ic1c cl~titlc~ l'ar~:iclc (,onccntl.ltiol~ n In~l~ort;lnt I'aralneter in l'itcll l~oblcllls," I-y 1,.11. /~1 Ic~ll, wllicll apl~c.lrs in ~:he Iralls;lctio!l.s oE the Iechllical_~e~tioll ol` ~:llc (all;l-li;lll I'ull) and l'al)cl ~sso~i;ltioll ~or .]UIIC, 1977, :it is clolllollstl<l-tcd -LIl;lt thos~ woo(l pllll)s wllich C;lllSC l-itcll problellns contilir a hi~h concclltr.ltioll oE sllspclldcd col loid.ll l~i-tcll p;lrticle.s~ 'I'hc pitcll cleposit potcllti.ll of a pllll~ is shown to hc pl~oportioll.ll to thc concentration o-E collo-idal pitCII drol~lets.
I`his article shows tha-t it is possible to measure the pitch by micro-scopic obscrv.ltion the concentration of colloidally suspended pitch droplets in *~
~S~9~4 a blood eounting chamber known as a hemacytometer. This particular method is described by the author in this article as follows:
"A. Particle ~oncen~ration Determinations Each pulp sample is filtered through a rapid, coarse, filter paper ~Reeve Angel No. 202) to remove the fibres, and the concentration of colloidally sus-pended pitch droplets in the filtrate is counted in a hemacytometer with a microscope. . ."
It is known that certain water-soluble polymers are capable of acting as pitch dispersants whereby the pitch can be maintained in a colloidal state of subdivision without agglomeration of the particles occurring. It is further known that certain polytners and, in particular, low molecular weight water-soluble cationic polymers, will cause the pitch particles to become attached to the fibers. This removes the colloidal pitch particles Erom the whitew,lter and tends to prevent deposit formation from occurring.
The ~present invent;oll ;s pred~ic;lted ut)on the discovery of certia;ll cat;onie pulylllers whicll give superior collo;dill pitcl~ll;lrticle recluctioll ;n aqueous pulps.
~ IUS thi.s illv(i~llt:ioll pl'OVi(lCs .1 IllCthO(I oE l`CdUCillg the alllount Or col-]okl;ll pitcll l)atticles in a(lllC011S p~ )'; which COIIII)risCs I t'C;ltillg Sai.(l pllll)S with a watel~-d-ispersil)le polyqlt;l~erllary polylller ol essenti:llly line~lt structure Ct)ll-sisting ossellti;llly of tl~e d.ilullct.i.oll.ll rcact:ion prodllct of a lowcr dialky1<1.lll:i.tlc and a diEullctioll;ll epoxy coml)olllld sclcctcd from the grolll) consisting of ep-ihalo-hydrills, d;opoxides, percursors of epih;llollydrins and diepoxides which under alkaline conditions are readily converted into the corresponding epoxy conlpounds, and m;xtures thereof, said polyquaternary polymer containing repeating units of ~L~5~914 N - E ~
L 12 ¦.X
wherein R and R2 are individually selected from the group consisting of alkyl of 1 to 3 carbon atoms, and E is a residue obtained from said epoxy compound;
the total amounts of reactants being substantially equimolar, the combination of which is such as to provide a polyquaternary compound l~hich as a 37% aqueous solution, by weight, based on the cationic portion of said polyquaternary compound has a viscosity at 25C. o:f at least 100 centistokes; and X re-prescnts an ion :forming thc anion;c portion of said polyquaterllary.
~ pre:ferred speci.es o-f polymers of tllc type dcscribed above are thosc prepared by us:ing as thc rcactants epichlorollydrill and d:imetllylamine.
Polyquaterllary polymcrs of the typc described .~hove alld thcir metllod of preparation are dcscribed in lJnited Statcs 3,738,9~l5.
rl`he dosage Or acti.vc polymcri.c comllollcllt llSCd t(l trc;lt thc ;Iqllcous ~u:ll)s may -range :from as li.ttlc ;m~ ().l ul~ to ;IS mllcll ;IS I killogr;llll l)cr ton o~F
ulp bascd on dry fibc:r wc:i.gllt.
rO :il:lustr;ltc thc clfi(:lcy ol`l~ly illvcntioll, thc lollowillg is l~rc-SCI~tc~(l I)y w:ly ol CX;IIIII)`l C.
Tllc tcst mctlloll uscd corrcsl)(!lldc(l gcllcr;llly to th;lt dcsclibcd l~y
2() L,.ll. Allcll ;n h;.s ;Irt:iclc, "I'i.tclll';lrticlc (onccllt:rltioll: an Iml~ortallt P:lr;lllleter in l)itch rroblellls~ wll:icll al~l)c~lrs in thc l`ransactions of thc Icchlli.-cal Sect;.on of the Calladiall Pulp ;IIld l'apcr Association for J~me, 1977.
IJsillg th:is test metllod, polymers of the invcntion were screened on a variety of pulps. The results are reported in terms of pitch particles per milliliter. In other cases it is reported in percent of pitch particles fixed ~5~)914 onto fibers by the polymers. This result is determined by the following equation:
rNumber of pitch Number of pitch ¦particles/mL - particles/mL - ~% pitcl~ particles untreated sample treated sample X l00= fixed onto fibres ~Number of pitch particles/l by polymer ~mL - untreated sample ~¦
The following procedures leading to the predictability of percent efflciency for the various polymers tested in regards to pitcl- control were used to generate all of the results in the following tablcs:
l. 1ake representat:ivc white watcr samples throughout the system as far back as the grinder showers in thc ground-wood mill but at a point in thc system prior to pitch deposits appec1ring and presenting a problem.
2. I'lace a known aliquot of thcse white water salllples ;n a Britt l)ynamic Jar or BDJ. Set the spce(1 varial)lc of the stirrcr for tllC Britt .Jar in a rangc of 500-l000 rpm for 2 minutc.s ;Ind dr1w off a sm.lll (lu;llltity oE the wh;tc w~ter prior to the polylller additioll. Ihi~s would l)c collsidcrc(l;l I)llnk or a control count al)sellt tre;ltlllcl-t cllcllli~;lls.
IJsillg th:is test metllod, polymers of the invcntion were screened on a variety of pulps. The results are reported in terms of pitch particles per milliliter. In other cases it is reported in percent of pitch particles fixed ~5~)914 onto fibers by the polymers. This result is determined by the following equation:
rNumber of pitch Number of pitch ¦particles/mL - particles/mL - ~% pitcl~ particles untreated sample treated sample X l00= fixed onto fibres ~Number of pitch particles/l by polymer ~mL - untreated sample ~¦
The following procedures leading to the predictability of percent efflciency for the various polymers tested in regards to pitcl- control were used to generate all of the results in the following tablcs:
l. 1ake representat:ivc white watcr samples throughout the system as far back as the grinder showers in thc ground-wood mill but at a point in thc system prior to pitch deposits appec1ring and presenting a problem.
2. I'lace a known aliquot of thcse white water salllples ;n a Britt l)ynamic Jar or BDJ. Set the spce(1 varial)lc of the stirrcr for tllC Britt .Jar in a rangc of 500-l000 rpm for 2 minutc.s ;Ind dr1w off a sm.lll (lu;llltity oE the wh;tc w~ter prior to the polylller additioll. Ihi~s would l)c collsidcrc(l;l I)llnk or a control count al)sellt tre;ltlllcl-t cllcllli~;lls.
3. Add ;l knowll doslgc ol poly1llcr lo ~llc ;lli(lllot ol whitc w;ltcr still cont;lilled in the l31)), sct tllc sl)ccd v;lri;ll)lc ol lllc stirlcr ;It t.l-c .s;lmc sl)cc~d use(l ft)r the control w;tllllo trc;l~lllcllt, ;IIId ;l~ tC it for 5 mill~ltcs ;It this spccd .
4. 1hc l`iltrltc .sholll(l imlllc(liltcly bc w;thdr;lwll. If thc pitcll plr-ticle concelltr;ltioll COllllt i~s c.Ytrcnlcly higll, ;l dilut-ioll E.lctor can bc int-roduced.
IE this dil~ltion step is nOt neccss;1ry, thcll ;I known aliq1lot of this filtrcltc is l)laccd 011 the hel~ cytollleter. The helll.lcytollleter is placed under the micro-scope and colloidal pitC]l particlcs are counted. Thus a count can be completed in a knol~l volume of liquid over a small square in the American optical hema--- 'I --~L~5~4 cytometer. The measurement of this volume in the hemacytometer is 2-5.10 7cm and the particle concentration would be expressed as the number times 106cm3.
IE this dil~ltion step is nOt neccss;1ry, thcll ;I known aliq1lot of this filtrcltc is l)laccd 011 the hel~ cytollleter. The helll.lcytollleter is placed under the micro-scope and colloidal pitC]l particlcs are counted. Thus a count can be completed in a knol~l volume of liquid over a small square in the American optical hema--- 'I --~L~5~4 cytometer. The measurement of this volume in the hemacytometer is 2-5.10 7cm and the particle concentration would be expressed as the number times 106cm3.
5. The initial count of the white water prior to the addition of the polymer is considered the blank. The second count is obtained using the known dosage of polymer addition. This second count would be subtracted from the blank and thus, a percentage efficiency of the polymer can be calculated using the previously mentioned formula.
The results of these tests are set forth in Tables I - VII.
TABLE I - GROUNDWOOD
Polymer Pitch Particules /mL
. .
Control 107,500 Competitive product A 52,250 Polymer of Invention 48,750 TABLE II - GROUNDWOOD
Polymer Pitch Particules /mL __ Control 58,750 Polymer of Lnvention 36,250 Competitive prodtlct A 72,500 Competitlve produc~ B l46,250 Competitive prodnct ~ Ls belLeve(l to be .In acrylallll(k~-dlllle~llyl-amLno ethyl methacrylate dimethyls~llE<Ite qu.llterll.lry copolymer in about 74:26 by we:L~ht;
competitive product B is a nitric acLd solution o~ poLy(2-bydroxy propyl amino ethyl acrylate).
A terpolymer of epichlorohydrin, dimethylamine, and ammonia in a mole ratio of 1:0-85:0.15 prepared according to US 3,738,945 having an approximate molecular weight of 50,000, used as a 47% by weight aqueous solution. This polymer is commercially available. -5-r~
115~914 TABLE III - GROUNDWOOD
Polymer Pitch particles /mL
. . _ Control 106,250 Polymer of Invention 52,500 Competitive Product A 71,250 Note: Following the addition of polymer, each sample was agitated for 2-5 minutes at 500-800 RPM prior to filtering.
TABLE [V - SULPHITE PULP
Polymer Pitch particlcs /mL
_ _ Contro] 63,750 Polymer of Invention 30,000 Competitive ~roduct A 35,000 Note: Results obtained on samples after agitation for 2-5 minutes a-t 500-800 RPM prior to f-iltering.
'I'ABI,I V - SUI,PIII'I`I` PlJLI' _ _ .
r~O 1 yll,cr 1~ i tcl~ lrticl~
(.ontrol 231,875 I'olylll~r ol` l~lvellti~o 10(),()n() Co~ )otit~ive ~ o~lJ~t ~ 82,5()() Note: Followillg the ad(litioll ol` polylller al)ove salll[)les were agit.lted for 2-5 minutes at 500-8()() Rl'M pl:ior to filtering.
~5~9~4 TABLE V I - GROUM)WOOD PULP
Polymer % of pitch particles fixed onto fibres by polymer.
Polymer of invention 45o TABLE VII - SULPHITE PULP
Polymer % of pitch particles fixed onto fibres by polymer.
Polymer of invention 55~o competitive product A 53O
From the abovc it is obvious that an advance in the paper treating art has been achieved.
The results of these tests are set forth in Tables I - VII.
TABLE I - GROUNDWOOD
Polymer Pitch Particules /mL
. .
Control 107,500 Competitive product A 52,250 Polymer of Invention 48,750 TABLE II - GROUNDWOOD
Polymer Pitch Particules /mL __ Control 58,750 Polymer of Lnvention 36,250 Competitive prodtlct A 72,500 Competitlve produc~ B l46,250 Competitive prodnct ~ Ls belLeve(l to be .In acrylallll(k~-dlllle~llyl-amLno ethyl methacrylate dimethyls~llE<Ite qu.llterll.lry copolymer in about 74:26 by we:L~ht;
competitive product B is a nitric acLd solution o~ poLy(2-bydroxy propyl amino ethyl acrylate).
A terpolymer of epichlorohydrin, dimethylamine, and ammonia in a mole ratio of 1:0-85:0.15 prepared according to US 3,738,945 having an approximate molecular weight of 50,000, used as a 47% by weight aqueous solution. This polymer is commercially available. -5-r~
115~914 TABLE III - GROUNDWOOD
Polymer Pitch particles /mL
. . _ Control 106,250 Polymer of Invention 52,500 Competitive Product A 71,250 Note: Following the addition of polymer, each sample was agitated for 2-5 minutes at 500-800 RPM prior to filtering.
TABLE [V - SULPHITE PULP
Polymer Pitch particlcs /mL
_ _ Contro] 63,750 Polymer of Invention 30,000 Competitive ~roduct A 35,000 Note: Results obtained on samples after agitation for 2-5 minutes a-t 500-800 RPM prior to f-iltering.
'I'ABI,I V - SUI,PIII'I`I` PlJLI' _ _ .
r~O 1 yll,cr 1~ i tcl~ lrticl~
(.ontrol 231,875 I'olylll~r ol` l~lvellti~o 10(),()n() Co~ )otit~ive ~ o~lJ~t ~ 82,5()() Note: Followillg the ad(litioll ol` polylller al)ove salll[)les were agit.lted for 2-5 minutes at 500-8()() Rl'M pl:ior to filtering.
~5~9~4 TABLE V I - GROUM)WOOD PULP
Polymer % of pitch particles fixed onto fibres by polymer.
Polymer of invention 45o TABLE VII - SULPHITE PULP
Polymer % of pitch particles fixed onto fibres by polymer.
Polymer of invention 55~o competitive product A 53O
From the abovc it is obvious that an advance in the paper treating art has been achieved.
Claims (2)
PROPERTY OR PRIVILEGE IS CLAIMED ARE DEFINED AS FOLLOWS:
1. A method of reducing the amount of colloidal pitch particles in aqueous pulps which comprises treating said pulps with an effective amount of a water-dispersible polyquaternary polymer of essentially linear structure consisting essentially of the difunctional reaction product of a lower dialkylamine and a difunctional epoxy compound selected from the group consisting of epihalohydrins, diepoxides, percursors of epihalohydrins and diepoxides which under alkaline conditions are readily converted into the corresponding epoxy compounds, and mixtures thereof, said polyquaternary polymer containing repeating units of wherein R and R2 are each individually selected from the group consisting of alkyl of 1 to 3 carbon atoms, and E is a residue obtained from said epoxy compound;
the total amounts of lower dialkylamine and difunctional epoxy compound reactants being substantially equimolar, the combination of which is such as to provide a polyquaternary compound which as a 37% aqueous solution, by weight, based on the cationic portion of said polyquaternary compound has a viscosity at 25°C. of at least :100 centistokes; and X represents an ion forming the anionic portion of said polyquaternary.
the total amounts of lower dialkylamine and difunctional epoxy compound reactants being substantially equimolar, the combination of which is such as to provide a polyquaternary compound which as a 37% aqueous solution, by weight, based on the cationic portion of said polyquaternary compound has a viscosity at 25°C. of at least :100 centistokes; and X represents an ion forming the anionic portion of said polyquaternary.
2. The method of Claim 1 where the lower dialkylamine is dimethylamino and the epihalohydrin is epichlorohydrin.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA000365778A CA1150914A (en) | 1980-11-28 | 1980-11-28 | Amine-epichlorohydrin polymers for pitch control |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA000365778A CA1150914A (en) | 1980-11-28 | 1980-11-28 | Amine-epichlorohydrin polymers for pitch control |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1150914A true CA1150914A (en) | 1983-08-02 |
Family
ID=4118586
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000365778A Expired CA1150914A (en) | 1980-11-28 | 1980-11-28 | Amine-epichlorohydrin polymers for pitch control |
Country Status (1)
| Country | Link |
|---|---|
| CA (1) | CA1150914A (en) |
Cited By (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0232015A1 (en) * | 1986-01-09 | 1987-08-12 | W.R. Grace AB | Pitch control aid |
| EP0493066A1 (en) * | 1990-12-24 | 1992-07-01 | W.R. Grace & Co.-Conn. | Pitch control |
| US5178770A (en) * | 1991-07-12 | 1993-01-12 | Nalco Canada Inc. | Method of treating bctmp/ctmp wastewater |
| US5223097A (en) * | 1986-01-09 | 1993-06-29 | W. R. Grace Ab | Method for controlling pitch on a paper-making machine |
| US5230774A (en) * | 1991-09-03 | 1993-07-27 | Nalco Chemical Company | Synergistic pitch control process utilizing ammonium zirconium and cationic polymers |
| EP0599440A1 (en) * | 1992-11-25 | 1994-06-01 | W.R. Grace & Co.-Conn. | Pitch reduction on paper machine surfaces |
| US5393380A (en) * | 1992-11-02 | 1995-02-28 | Nalco Chemical Company | Polydiallyl dimethyl ammonium chloride/3-acrylamido-3-methylbutanoic acid copolymers and their use for pitch control in paper mill systems |
| US5626720A (en) * | 1986-01-09 | 1997-05-06 | W.R. Grace & Co.-Conn. | Method for controlling pitch on a papermaking machine |
| US5723021A (en) * | 1995-04-12 | 1998-03-03 | Betzdearborn Inc. | Method for inhibiting deposition in pulp and papermaking systems using a composition comprising of polyvinyl alcohol, gelatin and cationic polymer |
| US5762757A (en) * | 1996-12-05 | 1998-06-09 | Betzdearborn Inc. | Methods for inhibiting organic contaminant deposition in pulp and papermaking systems |
| US5798023A (en) * | 1996-05-14 | 1998-08-25 | Nalco Chemical Company | Combination of talc-bentonite for deposition control in papermaking processes |
| US5866618A (en) * | 1995-04-12 | 1999-02-02 | Betzdearborn Inc. | Compositions and Methods for inhibiting the deposition of organic contaminants in pulp and papermaking systems |
| US5989392A (en) * | 1997-09-10 | 1999-11-23 | Nalco Chemical Company | Method of using polyammonium quaternary for controlling anionic trash and pitch deposition in pulp containing broke |
| US8506757B2 (en) | 2008-11-18 | 2013-08-13 | Hercules Incorporated | Hydrophobically modified poly(aminoamides) |
| JP2019143264A (en) * | 2018-02-21 | 2019-08-29 | アクアス株式会社 | Pitch suppressant for paper/pulp manufacturing process and pitch suppression method for paper/pulp manufacturing process |
-
1980
- 1980-11-28 CA CA000365778A patent/CA1150914A/en not_active Expired
Cited By (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0232015A1 (en) * | 1986-01-09 | 1987-08-12 | W.R. Grace AB | Pitch control aid |
| US5223097A (en) * | 1986-01-09 | 1993-06-29 | W. R. Grace Ab | Method for controlling pitch on a paper-making machine |
| US5626720A (en) * | 1986-01-09 | 1997-05-06 | W.R. Grace & Co.-Conn. | Method for controlling pitch on a papermaking machine |
| EP0493066A1 (en) * | 1990-12-24 | 1992-07-01 | W.R. Grace & Co.-Conn. | Pitch control |
| US5178770A (en) * | 1991-07-12 | 1993-01-12 | Nalco Canada Inc. | Method of treating bctmp/ctmp wastewater |
| US5230774A (en) * | 1991-09-03 | 1993-07-27 | Nalco Chemical Company | Synergistic pitch control process utilizing ammonium zirconium and cationic polymers |
| US5393380A (en) * | 1992-11-02 | 1995-02-28 | Nalco Chemical Company | Polydiallyl dimethyl ammonium chloride/3-acrylamido-3-methylbutanoic acid copolymers and their use for pitch control in paper mill systems |
| EP0599440A1 (en) * | 1992-11-25 | 1994-06-01 | W.R. Grace & Co.-Conn. | Pitch reduction on paper machine surfaces |
| US5723021A (en) * | 1995-04-12 | 1998-03-03 | Betzdearborn Inc. | Method for inhibiting deposition in pulp and papermaking systems using a composition comprising of polyvinyl alcohol, gelatin and cationic polymer |
| US5866618A (en) * | 1995-04-12 | 1999-02-02 | Betzdearborn Inc. | Compositions and Methods for inhibiting the deposition of organic contaminants in pulp and papermaking systems |
| US5952394A (en) * | 1995-04-12 | 1999-09-14 | Betzdearborn Inc. | Compositions and methods for inhibiting the deposition of organic contaminants in pulp and papermaking systems |
| US5798023A (en) * | 1996-05-14 | 1998-08-25 | Nalco Chemical Company | Combination of talc-bentonite for deposition control in papermaking processes |
| US5762757A (en) * | 1996-12-05 | 1998-06-09 | Betzdearborn Inc. | Methods for inhibiting organic contaminant deposition in pulp and papermaking systems |
| US6143800A (en) * | 1996-12-05 | 2000-11-07 | Hercules Incorporated | Compositions and method for inhibiting organic contaminant deposition in pulp and papermaking systems |
| US5989392A (en) * | 1997-09-10 | 1999-11-23 | Nalco Chemical Company | Method of using polyammonium quaternary for controlling anionic trash and pitch deposition in pulp containing broke |
| US8506757B2 (en) | 2008-11-18 | 2013-08-13 | Hercules Incorporated | Hydrophobically modified poly(aminoamides) |
| JP2019143264A (en) * | 2018-02-21 | 2019-08-29 | アクアス株式会社 | Pitch suppressant for paper/pulp manufacturing process and pitch suppression method for paper/pulp manufacturing process |
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