Anthony H. Conner

University of Wisconsin, Madison, Madison, MS, United States

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Publications (20)14.22 Total impact

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    ABSTRACT: A bioadhesive composition for bonding together adjacent surfaces of wood comprises a microbially-produced fermentation residue containing adherent microbial cells and glycocalyx. This residue finds particular application as a replacement for a significant amount of phenol-formaldehyde (PF) or other conventional adhesive component commonly used in the production of plywood and other wood products.
    01/2006;
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    P J Weimer, A H Conner, L F Lorenz
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    ABSTRACT: Residues from the fermentation of cellulose by the anaerobic bacteria Ruminococcus albus (strain 7) or Ruminococcus flavefaciens (strains FD-1 or B34b) containing residual cellulose, bacterial cells and their associated adhesins, were examined for their ability to serve as components of adhesives for plywood fabrication. The residues contained differing amounts of protein (0.4-4.2% of dry weight), but the ratios of monosaccharides recovered following two-stage treatment of the residue with detergent (pH 7) and TFA were similar for all three strains (0.71 glucose:0.18 xylose:0.08 mannose:0.02 galactose), suggesting similarities in exopolysaccharide composition. Three-ply aspen panels prepared with fermentation residues (FR) displayed better shear strength and wood failure under dry conditions than following a vacuum/pressure/soak/dry treatment, but adhesive properties were inferior to those prepared with conventional phenol-formaldehyde (PF) adhesives. However, panels prepared by incorporating the R. albus 7 FR into PF formulation, at 73% by weight of the total adhesive, exhibited shear strength and wood failure similar to that obtained with PF adhesive alone. Use of residues from fermentations by these bacteria as components of adhesives may add value to biomass fermentations aimed primarily at producing ethanol and other chemical products.
    Applied Microbiology and Biotechnology 12/2003; 63(1):29-34. · 3.69 Impact Factor
  • Barry F. Wood, Anthony H. Conner, Charles G. Hill Jr
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    ABSTRACT: The effect of precipitation on the molecular weight distributions of cellulose tricarbanilate (CTC) samples prepared from α-pulp, hydrolyzed α-pulp, and Avicel was determined using size exclusion chromatography (SEC). Precipitation of the CTC samples in methanol resulted in the loss of a low molecular weight fraction accounting for 26% of the weight of the hydrolyzed α-pulp, 20% of the Avicel, and 5% of the α-pulp. Precipitation in a methanol/water mixture resulted in less fractionation; in this case, however, the reaction byproducts were also precipitated. These results indicate that the molecular weight distribution of precipitated CTC may not accurately reflect the molecular weight distribution of the original cellulose. SEC analysis of the nonvolatile products from the carbanilation reaction offers a simple method for determining the complete molecular weight distribution of this cellulose derivative.
    Journal of Applied Polymer Science 03/2003; 32(2):3703 - 3712. · 1.40 Impact Factor
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    Anthony H. Conner, Linda F. Lorenz, Kolby C. Hirth
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    ABSTRACT: 2-Hydroxymethylphenol (2-HMP) and 4-hydroxymethylphenol (4-HMP) were used as model compounds to study the reactions that occur during cure of phenol–formaldehyde (PF) resin to which cure accelerators (ethyl formate, propylene carbonate, -butyrolactone, and triacetin) have been added. The addition of cure accelerators significantly increased the rate of condensation reactions. The cure accelerators were consumed during the reaction, indicating that they do not act as true catalysts. Major dimeric and trimeric reaction products were isolated and their structures determined. The results are consistent with a mechanism in which the hydroxymethyl group of 2-HMP (or 4-HMP) is first transesterified by the cure accelerator. The ester group is then displaced by reaction with the negatively charged ortho or para position of a second molecule (SN2 mechanism) or is converted to a reactive quinone methide intermediate, which subsequently reacts with the negatively charged ortho or para position of a second molecule (quinone methide mechanism). When accelerators were added to the reaction mixture, the self-condensation of 2-HMP was faster than that of 4-HMP. As is well documented in the literature, the exact opposite is true without added accelerators. This result would seem to indicate that the phenolic oxygen helps activate the esterified ortho-hydroxymethyl group. The number and nature of crosslinks in a PF resin cured with added cure accelerator might be different than those in a PF resin cured without an added cure accelerator. © 2002 Wiley Periodicals, Inc. J Appl Polym Sci 86: 3256–3263, 2002
    Journal of Applied Polymer Science 12/2002; 86(13):3256 - 3263. · 1.40 Impact Factor
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    Tohru Mitsunaga, Anthony H. Conner, Charles G. Hill Jr
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    ABSTRACT: Phenol–formaldehyde resins are important adhesives used by the forest products industry. The phenolic compounds in these resins are derived primarily from petrochemical sources. Alternate sources of phenolic compounds include tannins, lignins, biomass pyrolysis products, and coal gasification products. Because of variations in their chemical structures, the reactivities of these phenolic compounds with formaldehyde vary in quite subtle ways. Previously, it was demonstrated that the reactivity of a number of phenols with formaldehyde in nonaqueous conditions could be correlated with charges calculated for reactive sites on the aromatic ring (Conner, A. H. J Appl Polym Sci 2000, 78, 355–363). We studied the reactivity of a larger number of phenolic compounds with formaldehyde in an aqueous solution using sodium hydroxide as the catalyst. Reaction rates were determined from measurements of the concentrations of the phenolic compounds and formaldehyde as functions of time. The reaction rate constants varied over a wide range (approximately 10−2 to 104 L mol−1 h−1). An estimate of the reactivity per reactive site on the phenolic ring was determined by dividing the rate by the number of reactive sites. Atomic charges for each phenolic compound were calculated by ab initio methods at the RHF/6-31+ G level of theory using the CHelpG method. The charge per reactive site was estimated by summing the charges at all the reactive sites on the phenolic ring and dividing by the number of reactive sites. A strong correlation was observed between the reactivity per reactive site and the average charge per reactive site. © 2002 Wiley Periodicals, Inc. J Appl Polym Sci 86: 135–140, 2002
    Journal of Applied Polymer Science 10/2002; 86(1):135 - 140. · 1.40 Impact Factor
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    Journal of Organic Chemistry - J ORG CHEM. 04/2002; 60(6).
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    David R. Holm, Charles G. Hill, Anthony H. Conner
    Industrial & Engineering Chemistry Research - IND ENG CHEM RES. 04/2002; 34(10).
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    Tohru Mitsunaga, Anthony H. Conner, Charles G. Hill
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    ABSTRACT: The rates (k) of hydroxymethylation of phenol, resorcinol, phloroglucinol, and several methylphenols in diluted 10% dimethylformamide aqueous alkaline solution were calculated based on the consumption of phenols and formaldehyde. Thek values of phloroglucinol and resorcinol relative to that of phenol were about 62000 and 1200 times, respectively. The phenols that have methyl or hydroxyl groups at the C-3 or C-5 position (or both) have larger rate constants than phenols with substituents at other positions. Several kinds of atomic charge of the carbons on the aromatic ring of phenols were calculated using the semiempirical orab initio method. The correlations between the averagek (Ave.k) and average electrostatic charges (Ave.q) at the carbons were fairly good. Highest occupied molecular orbitals (HOMO) were observed. The best correlation between Ave.k and Ave.q was obtained when diphenols and triphenols were assumed to exist in solution as their respective di-anion.
    Journal of Wood Science 03/2002; 48(2):153-158. · 0.77 Impact Factor
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    Tohru Mitsunaga, Anthony H. Conner, Charles G. Jr. Hill
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    ABSTRACT: Phenolic resins are important adhesives used by the forest products industry. The phenolic compounds in these resins are derived primarily from petrochemical sources. Alternate sources of phenolic compounds in- clude tannins, lignins, biomass pyrolysis products, and coal gasification products. Because of variations in their chemical structures, the reactivities of these phenolic compounds with formaldehyde vary in quite subtle ways. A method is needed for predicting the reactivity of phenolic compounds with formaldehyde in order to al- low researchers to efficiently choose those compounds that might make the best candidates for new adhesive systems prior to conducting extensive laboratory trials. Computational chemistry has been used to study the relationship between the reactivity of a number of phe- nolic compounds with formaldehyde in an aqueous, al- kaline system, and charges calculated for reactive sites on the aromatic ring of the phenolic compound. Atomic-charges for each phenolic compound were cal- culated by ab initio methods at the RHF/6-31 +G level of theory using the ChelpG method. Reaction rate con- stants were determined from measurements of the con- centrations of the phenolic compounds and formalde- hyde as functions of time. The reaction rate constants varied over a wide range (approx. 10 -2 to 10 4 L mol -1 hr. -1 ). An estimate of the reactivity per reactive site on the phenolic ring was determined by dividing the rate constant by the number of reactive sites. The charge per reactive site was estimated by summing the charges at all the reactive sites on the phenolic ring and dividing by the number of reactive sites. A strong correlation was observed between the reactivity per reactive site and the average charge per reactive site.
    01/2001;
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    ABSTRACT: The effects of temperature, acid concentration, and reactant concentration on the rate of formation of difurfuryldiamines from the reactions of furfurylamine with formaldehyde and acetaldehyde were experimentally investigated. On the basis of the data from these experiments, a semimechanistic reaction model network was proposed and a mathematical model which describes the observed kinetic behavior was derived. Rate constants for the model reactions were found to depend exponentially both on the reciprocal of the absolute temperature and on the acid concentration. The mathematical model predicts concentration versus time profiles for reactants, intermediate, and product for the reaction of furfurylamine and acetaldehyde under the following conditions:  20 °C < temperature < 50 °C, 3 M < nominal acid concentration < 6 M, 1.17 M < [furfurylamine] < 1.2 M, and 0.303 M < [acetaldehyde] < 1.17 M. For the reaction of furfurylamine with formaldehyde the model is applicable for 30 °C < temperature < 50 °C, 3 M < nominal acid concentration < 6 M, [furfurylamine] = 1.17 M, and [formaldehyde] = 0.58 M.
    Industrial & Engineering Chemistry Research - IND ENG CHEM RES. 03/1997; 36(3).
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    ABSTRACT: A protocol which employs a methyl silicone gum capillary column for gas chromatographic analysis of the products of the acid- catalyzed reaction of furfurylamine with aldehydes is presented, and its efficacy is demonstrated.
    Journal of Chromatography A. 08/1993; 644(2):383–387.
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    ABSTRACT: The syntheses of difurfuryl diisocyanates [e.g., ethylidenebis (2,5-furandiylmethylene) diisocyanate (EDFI)] have been reported in the literature. Difurfuryl diisocyanates are structurally similar to diphenylmethane diisocyanate (MDI), which has proven to be an excellent adhesive for bonding wood composites. The MDI regin is synthesized from petroleum-derived chemicals; the EDFI resin is synthesized from biomass-derived chemicals. In this study, the mechanical properties of aspen flakeboards bonded with MDI and EDFI are compared. In general, results show that the strength properties of flakeboards bonded with MDI are only marginally better than those bonded with EDFI. Because EDFI is more viscous than is MDI less than optimum atomization of the EDFI resin during spraying of the flakes is believed to be largely responsible for the differences in strength property values. The dry internal bond strength values of flakeboards bonded with MDI (1.33 MPa; 193 lb/in.2) at 3% resin content are significantly greater than the 0.41 MPa (60 lb/in.2) required by the American National Standards Institute (ANSI/A208.1) for type-2 medium-density particleboard. © 1993 John Wiley & Sons, Inc.†
    Journal of Applied Polymer Science 07/1993; 49(2):337 - 344. · 1.40 Impact Factor
  • Chyong-Huey Lin, Anthony H. Conner, Charles G. Hill
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    ABSTRACT: Thirteen prehydrolyzed samples of cellulose, including native, mercerized, and regenerated materials were hydrolyzed in 1% and 1.5% sulfuric acid at 160, 170, and 180°C. Pseudo first-order rate constants and weight average degrees of polymerization were determined for each sample. For all cellulose samples, data from several experiments were used to determine the dependence of the rate of hydrolysis on sulfuric acid concentration. The results obtained in this study indicate that Sharples' end-attack model is consistent with kinetic data for the hydrolysis of cellulose II samples, but is not applicable to the hydrolysis of cellulose I samples. X-ray diffraction analyses indicated that, for native and mercerized cellulose samples, structural changes during dilute acid hydrolysis are not significant. However, data for rayon indicated that such changes may need to be taken into account in analysis of the reaction kinetics.
    Journal of Applied Polymer Science 01/1992; 45(10):1811-1822. · 1.40 Impact Factor
  • Chyong-Huey Lin, Anthony H. Conner, Charles G. Hill
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    ABSTRACT: Nine prehydrolyzed cellulose samples, including native, mercerized, and regenerated celluloses were hydrolyzed in 2% sulfuric acid at 150, 160, and 170°C. The first-order rate constants and the weight average degrees of polymerization (by size exclusion chromatography) were determined for each sample. The results indicate that Sharples' end-attack model [Trans. Faraday Soc., 53, 1003 (1957)] is consistent with kinetic data for cellulose II samples, but is not appropriate for characterizing the reactions of cellulose I samples.
    Journal of Applied Polymer Science 01/1991; 42(2):417-426. · 1.40 Impact Factor
  • Barry F. Wood, Anthony H. Conner, Charles G. Hill
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    ABSTRACT: The end-attack model proposed by Sharples [Trans. Faraday Soc., 53, 1003 (1957)] for the dilute acid hydrolysis of crystalline cellulose was tested using the results from the size-exclusion chromatographic analysis of samples of crystalline cellulose I and cellulose II hydrolyzed in 6.1N HCl at 107°C. The differential number distribution of the molecular weight of hydrolyzed cellulose was found to be approximately exponential, a result which is consistent with the end-attack model. Differences in the rates of hydrolysis of cellulosic materials appear to arise from differences in both the degree of polymerization and the microstructure of hydrolyzed cellulose. Evidence is also presented which suggests that the recrystallization upon hydrolysis results in part from the lateral accretion of chains which are cleaved during the hydrolysis of amorphous regions in the cellulose microfibrils.
    Journal of Applied Polymer Science 01/1989; 37(5):1373-1394. · 1.40 Impact Factor
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    Anthony H. Conner, Bryan H. River, Linda F. Lorenz
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    ABSTRACT: For adhesive self-sufficiency, the wood industry needs new adhesive systems in which all or part of the petroleum-derived phenolic component is replaced by a renewable material without sacrificing high durability or ease of bonding. We tested the bonding of wood veneers, using phenolic resins in which part of the phenol-formaldehyde was replaced with carbohydrates. Our experiments show that the addition of non-reducing carbohydrates and various polyols to phenol-formaldehyde resol-resins does not adversely affect the dry- or wet-shear strength of 2-ply Douglas-fir panels bonded with the modified resins. Reducing carbohydrates, however, cannot be used as the modifier. In general, addition of about 0.6–1.0 mole of modifier per mole of phenol is optimal in the formulation of carbohydrate-or polyol-modified resin. Preliminary results show that part but not all of the modifier is chemically bound into the resin, apparently through an ether linkage. The water prehydrolysate of southern red oak wood, when reduced with sodium borohydride to convert the reducing sugars to alditols, can be used to modify phenol-formaldehyde resins. This use of wood prehydrolysates can be economically beneficial to processes producing alcohol and chemicals from wood as well as to the wood industry and consumers of bonded wood products.
    Journal of Wood Chemistry and Technology - J WOOD CHEM TECHNOL. 01/1986; 6(4):591-613.
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    ABSTRACT: Despite continuing interest in various processes for producing ethanol or other chemicals from agricultural and wood residues, little attention has been given to improving the kinetic modeling of dilute acid saccharification of cellulosics, a key step in many of these processes. A new model for cellulose saccharification is proposed. It incorporates the effect of the neutralizing capacity of the substrate, the presence of readily hydrolyzable cellulose, and the reversion reactions of glucose. Although general in nature, the model was developed specifically for application to the dilute sulfuric acid saccharification of prehydrolyzed wood lignocellulose. A computer program to simulate the new model under various reaction conditions was prepared. This program reasonably predicts yields of fermentable (monomeric) sugar, reducing sugar, reversion material, remaining cellulose, as well as glucose lost by dehydration, all as a function of acid concentration, temperature, and reaction time.
    Journal of Wood Chemistry and Technology - J WOOD CHEM TECHNOL. 01/1985; 5(4):461-489.
  • Anthony H. Conner, Bryan H. River, Linda F. Lorenz
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    ABSTRACT: Various solvent systems capable of dissolving cellulose have been reported in the literature. Cuene (cupriethylene diamine hydroxide) and FeTNa (ferric sodium tartrate) are well known examples. Preliminary experiments were conducted with Cuene and FeTNa to determine if the cellulose dissolving ability of these systems could be used to bond yellow birch veneers. The results indicate that relatively high dry shear strengths, and low wet shear strengths are obtained.
    Journal of Wood Chemistry and Technology - J WOOD CHEM TECHNOL. 01/1984; 4(4):533-540.
  • Anthony H. Conner, Linda F. Lorenz
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    ABSTRACT: Most processes for utilizing wood as a source of chemicals and liquid fuels include a prehydrolysis step to remove the hemicellulose prior to the main hydrolysis of the cellulose to glucose. Two promising prehydrolysis methods, the Iotech steam explosion process and the Stake process, are based on water prehydrolysis (autohydrolysis). The kinetics of water and of dilute (5%) acetic acid prehydrolysis of southern red oak wood over the temperature range of 170 to 240 C were investigated. Kinetic parameters were determined that permitted modeling not only of xylan removal from the wood but also of the occurrence of xylan oligosaccharides, free xylose, furfural, and further degradation products in the prehydrolyzate. At lower temperatures (approximately 170 to 200 C), xylan removal could be modeled as the sum of two parallel reactions (one for an easily hydrolyzed portion and one for a more resistant portion of xylan) using the equation derived in Part I. At the highest temperature studied (236.9 C), the removal of xylan from the wood was best modeled as a single reaction with a small fraction of the xylan being essentially nonreactive. The occurrence of xylan oligosaccharides, xylose, furfural, and further degradation products in the prehydrolyzate was modeled as consecutive, irreversible pseudo first-order reactions. A timelag associated with the depolymerization of the xylan oligosaccharides to xylose was accounted for in the model by allowing the apparent rate constant for the formation of xylose to increase exponentially with time to a maximum value.
  • Linda F. Lorenz, Anthony H. Conner