Chlorohydrin and cationic compounds having high affinity for pulp or paper

• US 6,989,449 B1
• Filed: 09/11/2000
• Issued: 01/24/2006
• Est. Priority Date: 09/15/1999
• Status: Expired due to Fees

• Current Assignee: Ciba Specialty Chemicals Corp (BASF SE)
• Original Assignee: Ciba Specialty Chemicals Corp (BASF SE)
• Inventors: Cunkle, Glen T., Thompson, Thomas F., Devore, David
• Primary Examiner(s): FORTUNA, JOSE A
• Application Number:
  US09/658,924
• Time in Patent Office: 1,961 Days
• Field of Search: 162/72, 162/82, 162/160, 162/76, 162/158, 162/162, 162/164.6, 162/164.7, 162165-167, 514/235.01, 514/316, 514/319, 514/321, 514/329, 546/1, 546/11, 546/184, 546185-188, 546/216, 546/219, 546/242, 546/220, 524/87, 524/99, 252/399
• US Class Current: 546/242
• CPC Class Codes: C04B 35/632 Organic additives
• CPC Class Codes: C07D 211/94 Oxygen atom, e.g. piperidine N-oxide
• CPC Class Codes: C07D 401/04 directly linked by a ring-member-to-ring-member bond
• CPC Class Codes: C07D 401/12 linked by a chain containing hetero atoms as chain links
• CPC Class Codes: C07D 401/14 containing three or more hetero rings
• CPC Class Codes: C07D 471/10 Spiro-condensed systems
• CPC Class Codes: C08K 5/3435 Piperidines
• CPC Class Codes: C08L 97/00 Compositions of lignin-containing materials of polysaccharides C08L1/00 - C08L5/00
• CPC Class Codes: D21H 21/143 Agents preventing ageing of paper, e.g. radiation absorbing substances

Abstract

Selected chlorohydrin and cationic compounds containing nitroxide or hydroxylamine moieties are effective in stabilizing pulp or paper, especially pulp or paper containing lignin, against yellowing and discoloration due to the adverse effects of light. These compounds are added at various points in the paper-making process, especially at the wet ends, making the need for water soluble or water dispersible materials having high affinity for pulp or paper essential. This performance is often further enhanced by the presence of one or more coadditives selected from the group consisting of the UV absorbers, the polymeric inhibitors, the nitrones, the fluorescent whitening agents and metal chelating agents. Combinations of hydroxylamines or their salts, benzotriazole or benzophenone UV absorbers and a metal chelating agent are particularly effective.

Claims

1. A compound of formula VIII or VIIIA

where

n is 1 or 2 and m ranges from 2 to 6;

E is oxyl, hydroxyl, hydrogen, alkyl, alkyl substituted by hydroxyl, by oxo or by carboxy, alkyl interrupted by oxygen, by —

COO—

or by —

OCO—

, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, bicycloalkyl, alkoxy, alkoxy substituted by hydroxyl, by oxo or by carboxy, alkoxy interrupted by oxygen, by —

COO—

or by —

OCO—

, cycloalkoxy, alkenyloxy, cycloalkenyloxy, aralkyl, aralkoxy, acyl, RCOO—

, ROCOO—

, RNCOO—

or chloro where R is an aliphatic or aromatic moiety,

when n is 1,

R₁ is hydrogen, alkyl of 1 to 18 carbon atoms, alkenyl of 2 to 18 carbon atoms, propargyl, glycidyl, alkyl of 2 to 50 carbon atoms interrupted by one to twenty oxygen atoms, alkyl of 2 to 50 carbon atoms substituted by one to ten hydroxyl groups or both interrupted by said oxygen atoms and substituted by said hydroxyl groups, or

R₁ is alkyl of 1 to 4 carbon atoms substituted by a carboxy group or by —

COOZ where Z is hydrogen, alkyl of 1 to 4 carbon atoms or phenyl, or where Z is said alkyl substituted by —

(COO⁻

)_nMⁿ⁺ where n is 1–

3 and M is a metal ion from the 1st, 2nd or 3rd group of the periodic table or is Zn, Cu, Ni or Co, or M is a group Nⁿ⁺ (R₂)₄ where R₂ is hydrogen, alkyl of 1 to 8 carbon atoms or benzyl, or

when n is 2,

R₁ is alkylene of 1 to 12 carbon atoms, alkenylene of 4 to 12 carbon atoms, xylylene or alkylene of 1 to 50 carbon atoms interrupted by one to twenty oxygen atoms, substituted by one to ten hydroxyl groups or both interrupted by said oxygen atoms and substituted by said hydroxyl groups,

X is an inorganic or organic anion, where the index j equals the number of ammonium ions in the formula divided by the valency of X; and

the total charge of cations is equal to the total charge of anions.

2. A compound according to claim 1 wherein the anion X is phosphate, phosphonate, carbonate, bicarbonate, nitrate, chloride, bromide, iodide 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 diethylenetriaminepentaacetic acid, a diethylenediaminetetraacetic acid or of diethylenetriaminepentaacetic acid, an alkylsulfonate or an arylsulfonate.

3. A compound according to claim 1 wherein E is selected from oxyl, hydroxyl, C₁–

C₁₈alkoxy;

C₃–

C₁₈alkoxy substituted by hydroxyl, oxo or carboxy or interrupted by oxygen or carboxy;

C₅–

C₁₂cycloalkoxy;

C₃–

C₁₂alkenyloxy;

cyclohexenyloxy;

aralkyl or aralkoxy of 7 to 15 carbon atoms;

C₁–

C₁₂ acyl;

R(C═

O)O—

, RO(C═

O)O—

, RN(C═

O)O—

, where R is C₁–

C₁₈alkyl, phenyl, C₇–

C₁₅phenylalkyl, cyclohexyl, C₂–

C₃alkenyl.

4. A compound according to claim 1 of formula VIII.

5. A compound according to claim 4, wherein

m is 2 or 3;

E is oxyl, hydroxyl, or C₁–

C₈alkyl;

R₁, when n is 1, is H or C₁–

C₈alkyl, or, when n is 2, is alkylene of 2–

12 carbon atoms; and

X is chloride, bromide or citrate.