Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Patent
1997-06-19
1999-08-17
Geist, Gary
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
1621681, 162169, C07D30736
Patent
active
059395621
DESCRIPTION:
BRIEF SUMMARY
The present invention relates to new alkene-substituted cyclic carboxylic acid anhydrides. Of these, in particular alkene-substituted succinic acid anhydrides, i.e. so-called ASA sizing agents, are used, for example; in the hydrophobic sizing of paper. The invention also relates to a process for preparing these anhydrides. Furthermore, the invention relates to a method of hydrophobic paper sizing within the neutral or the alkaline pH range by using ASA sizing agents prepared by the process according to the invention.
Paper or cardboard material is usually treated in connection with manufacture or finishing with so-called sizing agents in order to produce a hydrophobic paper material. The purpose of this procedure is to reduce the penetration and adsorption of water and other liquids, such as ink, into the paper. Only sized paper is suitable for printing and writing purposes.
Usually the hydrophobic sizing of paper or cardboard material is carried out by using substituted cyclic carboxylic acid anhydrides, the most commonly used among them being substituted succinic acid anhydrides. The substituents may be alkyl, alkene, aralkyl or aralkene groups, as disclosed in, for example; U.S. Pat. No. 3 102 064. Alkene substituents are the most commonly used.
Alkene-substituted succinic acid anhydrides are prepared by a simple method by allowing an alkene compound to react with maleic anhydride at a temperature of 150-250.degree. C.
U.S. Pat. No. 3 821 069 discloses for the sizing of paper an alkene-substituted succinic acid anhydride the alkene substituent of which comprises an internal olefin preferably having 14-22 carbon atoms. The double bond of the olefin is at least in position 6 in the carbon chain.
GP patent publication 2 015 612 discloses for the neutral sizing of paper the use of an aqueous emulsion of a butene oligomer substituted succinic acid anhydride. The oligomer comprises 16-40 carbon atoms, and it is obtained through the oligomerization of 1-butene, 2-butene or isobutylene, the last-mentioned being the most preferable. The aqueous emulsion is prepared by using preferably cationic starch. For improving sizing efficacy, the method according to the publication uses a cationic retention agent, for example, a commercially available water-soluble cross-bridged polyamidoamine.
U.S. Pat. No. 4 576 680 discloses for use for the sizing of paper the reaction product of maleic anhydride and a branched internal 14-36 carbon atom olefin oligomer. The oligomer is formed from one or several olefins containing 6-18 carbon atoms. The double bond in the chain is at least in position 3. For the preparation of the sizing agent emulsion there are additionally needed a dispersing agent, such as cationic starch, and an emulsifier, such as certain fatty acids, ethers, phenols, esters, and their acetylated products.
JP patent publication 61 172 866 discloses for the sizing of paper an alkene-substituted succinic acid anhydride in which the alkene substituent is a 12-22 carbon atom straight-chain 1-olefin obtained by oligomerizing ethylene, by dehydrochlorinating chlorinated paraffin, or by decomposing wax or the like.
In the process according to EP patent publication 522564, the alkene substituent used in the substituted succinic acid anhydride intended for paper sizing consists of straight-chain internal olefins containing 16-20 carbon atoms.
In JP patent publication 57 154 496, the alkene substituent in the succinic acid anhydride is also made up of linear, internal olefins. However, if internal olefins are used for the preparation of ASA sizing agents, sizing agents are obtained which have a high reactivity with respect to paper fiber, but on the other hand they also have a high hydrolysis rate in water, and thus it is difficult to obtain an emulsion sufficiently stable for paper making. The poor stability of the emulsion thus results in that the useful life of the emulsion is short and that it is difficult to obtain on the paper surface a uniform-quality ASA neutral sizing agent.
It should be noted additionally that, ac
REFERENCES:
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patent: 4736044 (1988-04-01), Hanson
CA:66:77993, abs of "Extraction and chromatographic equilibria of oils" Reveda, Ropa Uhlie, 8(11)pp. 323-327 1996.
CA:114:210289, abs of "Synthetic petroleum products bsed on n-butylene oligomers". Zeinalov, Azerb. Neft. Khoz., (2) pp. 51-52, 1990.
CA:105:228822, abs of JP6116049 Jul. 1986.
WPIDS accession no 74-71819V Jul. 1974.
Halme Erkki
Kapanen Mika
Koskimies Salme
Rantanen Jaana
Savolainen Raija
Geist Gary
Neste Oy
Vollano Jean F
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