胶原降解物制备表面活性剂能的研究
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摘要
将胶原蛋白水解物与不同碳链长度的酰氯进行反应,制备了一系列不同碳链长度的CxLS表面活性剂;根据反应后产物中的游离氨基转化率确定最佳反应条件。通过FT-IR对CxLS的结构进行表征,同时测定了CxLS溶液的表面张力、起泡性和泡沫稳定性等参数。结果表明:合成CxLS的最佳反应pH值为9,乙酸乙酯与月桂酰氯的体积比为2∶1,反应温度为60℃,转化率最高为77.9%。随着酰氯的碳链长度增加,CxLS中游离氨基含量下降,泡沫稳定性增加。酰氯碳链长度为12的月桂酰基CxLS具有最低的表面张力和良好的泡沫稳定性。
The collagen hydrolysate was prepared by waste leather shavings via alkali hydrolysis.According to Schotten-Baumann reaction, varied collagen hydrolysate-based amino acid surfactants were prepared with collagen hydrolysate and different kinds of acyl chloride with different carbon chain length. The optimal reaction conditions were determined by the free amino content in surfactant solution. The structures of amino acid surfactants were evaluated by Fourier transform infrared spectroscopy analyses (FT-IR). Their physicochemical properties, such as surface tension, foaming and foam stability were investigated. It can be obtained that the reaction pH value was 9, the volume ratio of ethyl acetate to lauroyl chloride was 2 ∶1, the reaction temperature was 60 ℃ and the highest conversion rate was 77.9%. As carbon chain length of acyl chloride increasing, the free amino content in surfactants declined, and their foam stability increased. Lauroyl surfactant with C12 has the lowest surface tension and highest foaming stability.
The collagen hydrolysate was prepared by waste leather shavings via alkali hydrolysis.According to Schotten-Baumann reaction, varied collagen hydrolysate-based amino acid surfactants were prepared with collagen hydrolysate and different kinds of acyl chloride with different carbon chain length. The optimal reaction conditions were determined by the free amino content in surfactant solution. The structures of amino acid surfactants were evaluated by Fourier transform infrared spectroscopy analyses (FT-IR). Their physicochemical properties, such as surface tension, foaming and foam stability were investigated. It can be obtained that the reaction pH value was 9, the volume ratio of ethyl acetate to lauroyl chloride was 2 ∶1, the reaction temperature was 60 ℃ and the highest conversion rate was 77.9%. As carbon chain length of acyl chloride increasing, the free amino content in surfactants declined, and their foam stability increased. Lauroyl surfactant with C12 has the lowest surface tension and highest foaming stability.
引文
[1]Hu J,Xiao Z B,Zhou R J,et al.Ecological utilization of leather tannery waste with circular economy model[J].Journal of Cleaner Production,2011,19(2-3):221-228.
[2]栾俊,刁屾,陈沛海,等.革屑资源化利用研究进展[J].皮革科学与工程,2016,26(05):28-34.
[3]汪晓鹏.制革固废物的综合利用和展望[J].西部皮革,2017,39(17):38-42.
[4]Bogue R H.Conditions affecting the hydrolysis of collagen to gelatin[J].Industrial and Engineering Chemistry,2002,15(11):1154-1159.
[5]Bet M R,Goissis G,Lacerda C A.Characterization of polyanionic collagen prepared by selective hydrolysis of asparagine and glutamine carboxyamide side chains[J].Biomacromolecules,2001,2(4):1074.
[6]王瑞瑞,王鸿儒.活性胶原蛋白提取与表征方法研究进展[J].应用化工,2017,(11):1-8.
[7]Li C H,Liu W T,Duan L,et al.Surface activity of pepsin-solubilized collagen acylated by lauroyl chloride along with succinic anhydride[J].Journal of Applied Polymer Science,2014,131(14):8.
[8]沈益超,张晓玲,金勇.非离子型含氟表面活性剂的合成及应用研究进展[J].皮革科学与工程,2018,28(3):24-31.
[9]吕斌,高建静,王泓棣.表面活性剂在制革行业中的应用概述[J].日用化学品科学,2015,(11):48-52.
[10]Foley P,Pour A K,Beach E S,et al.Derivation and synthesis of renewable surfactants[J].Chemical Society Reviews,2012,41(4):1499-1518.
[11]汪保川,李宇鹏,戴国琛,等.蛋白基表面活性剂的合成、性能与应用进展[J].化工进展,2017,(07):2607-2614.
[12]Marchant R,Banat I.Biosurfactants:a sustainable replacement for chemical surfactants[J].Biotechnology Letters,2012,34(9):1597-1605.
[13]Muthukumar T,Sreekumar G,Sastry T P,et al.Collagen as a potential biomaterial in biomedical applications[J].Reviews on Advanced Materials Science,2018,53(1):29-39.
[14]Chi Y L,Zhang Q X,Liao X P,et al.Physicochemical properties and surface activities of collagen hydrolysate-based surfactants with varied oleoyl group grafting degree[J].Industrial and Engineering Chemistry Research,2014,53(20):8501-8508.
[15]迟原龙,崔敏,廖学品,等.胶原多肽基表面活性剂合成工艺的优化[J].中国皮革,2011,40(23):8-11.
[16]迟原龙,崔敏,杨倩,等.胶原多肽基表面活性剂的表面特性和生物降解性研究[J].中国皮革,2012,41(11):37-41+46.
[17]迟原龙,付睿婕,韩威妺,等.五种胶原多肽基表面活性剂合成路线的理论和实验研究[J].中国科技论文,2016,11(18):2115-2118.
[18]Li C H,Tian H L,Duan L,et al.Characterization of acylated pepsin-solubilized collagen with better surface activity[J].International Journal of Biological Macromolecules,2013,57(6):92-98.
[19]Li C H,Tian Z H,Liu W T,et al.Structural properties of pepsin-solubilized collagen acylated by lauroyl chloride along with succinic anhydride[J].Materials Science and Engineering C:Materials for Biological Applications,2015,55(14):327-334.
[20]王学川,王琳,许伟.基于胶原蛋白的发泡剂的制备及表征[J].皮革科学与工程,2017,(01):13-19.
[21]林虬,黄薇,宋永康,等.棉籽蛋白水解物水解度3种测定方法的比较[J].福建农业学报,2011,26(06):1076-1080.
[22]罗艳华.不同肽链长度蛋白基表面活性剂的制备及性能研究[D].陕西科技大学,2017.
[23]Lucas R,Comelles F,Alcantara D,et al.Surface-Active Properties of Lipophilic Antioxidants Tyrosol and Hydroxytyrosol Fatty Acid Esters:A Potential Explanation for the Nonlinear Hypothesis of the Antioxidant Activity in Oil-in-Water Emulsions[J].Journal of Agricultural and Food Chemistry,2010,58(13):8021-8026.
[24]秦树法,王芳,汤克勇,等.利用水解胶原蛋白制备多肽酰胺表面活性剂[J].中国皮革,2013,(09):13-15.
[25]栾俊.利用废革屑制备不同碳链长度N-酰基多肽表面活性剂及其性能研究[D].烟台大学,2016.
[26]Camacho N P,West P,Torzilli P A,et al.FTIR microscopic imaging of collagen and proteoglycan in bovine cartilage[J].Biopolymers,2015,62(1):1-8.
[27]Payne K J,Veis A.Fourier transform IR spectroscopy of collagen and gelatin solutions:deconvolution of the amide I band for conformational studies[J].Biopolymers,1988,27(11):1749.
[28]Quagliotto P,Montoneri E,Tambone F,et al.Chemicals from wastes:compost-derived humic acid-like matter as surfactant[J].Environmental Science and Technology,2006,40(5):1686-1692.
[29]王林林.N-中碳链脂肪酰基氨基酸盐的合成及表面活性研究[D].南昌大学,2013.
[2]栾俊,刁屾,陈沛海,等.革屑资源化利用研究进展[J].皮革科学与工程,2016,26(05):28-34.
[3]汪晓鹏.制革固废物的综合利用和展望[J].西部皮革,2017,39(17):38-42.
[4]Bogue R H.Conditions affecting the hydrolysis of collagen to gelatin[J].Industrial and Engineering Chemistry,2002,15(11):1154-1159.
[5]Bet M R,Goissis G,Lacerda C A.Characterization of polyanionic collagen prepared by selective hydrolysis of asparagine and glutamine carboxyamide side chains[J].Biomacromolecules,2001,2(4):1074.
[6]王瑞瑞,王鸿儒.活性胶原蛋白提取与表征方法研究进展[J].应用化工,2017,(11):1-8.
[7]Li C H,Liu W T,Duan L,et al.Surface activity of pepsin-solubilized collagen acylated by lauroyl chloride along with succinic anhydride[J].Journal of Applied Polymer Science,2014,131(14):8.
[8]沈益超,张晓玲,金勇.非离子型含氟表面活性剂的合成及应用研究进展[J].皮革科学与工程,2018,28(3):24-31.
[9]吕斌,高建静,王泓棣.表面活性剂在制革行业中的应用概述[J].日用化学品科学,2015,(11):48-52.
[10]Foley P,Pour A K,Beach E S,et al.Derivation and synthesis of renewable surfactants[J].Chemical Society Reviews,2012,41(4):1499-1518.
[11]汪保川,李宇鹏,戴国琛,等.蛋白基表面活性剂的合成、性能与应用进展[J].化工进展,2017,(07):2607-2614.
[12]Marchant R,Banat I.Biosurfactants:a sustainable replacement for chemical surfactants[J].Biotechnology Letters,2012,34(9):1597-1605.
[13]Muthukumar T,Sreekumar G,Sastry T P,et al.Collagen as a potential biomaterial in biomedical applications[J].Reviews on Advanced Materials Science,2018,53(1):29-39.
[14]Chi Y L,Zhang Q X,Liao X P,et al.Physicochemical properties and surface activities of collagen hydrolysate-based surfactants with varied oleoyl group grafting degree[J].Industrial and Engineering Chemistry Research,2014,53(20):8501-8508.
[15]迟原龙,崔敏,廖学品,等.胶原多肽基表面活性剂合成工艺的优化[J].中国皮革,2011,40(23):8-11.
[16]迟原龙,崔敏,杨倩,等.胶原多肽基表面活性剂的表面特性和生物降解性研究[J].中国皮革,2012,41(11):37-41+46.
[17]迟原龙,付睿婕,韩威妺,等.五种胶原多肽基表面活性剂合成路线的理论和实验研究[J].中国科技论文,2016,11(18):2115-2118.
[18]Li C H,Tian H L,Duan L,et al.Characterization of acylated pepsin-solubilized collagen with better surface activity[J].International Journal of Biological Macromolecules,2013,57(6):92-98.
[19]Li C H,Tian Z H,Liu W T,et al.Structural properties of pepsin-solubilized collagen acylated by lauroyl chloride along with succinic anhydride[J].Materials Science and Engineering C:Materials for Biological Applications,2015,55(14):327-334.
[20]王学川,王琳,许伟.基于胶原蛋白的发泡剂的制备及表征[J].皮革科学与工程,2017,(01):13-19.
[21]林虬,黄薇,宋永康,等.棉籽蛋白水解物水解度3种测定方法的比较[J].福建农业学报,2011,26(06):1076-1080.
[22]罗艳华.不同肽链长度蛋白基表面活性剂的制备及性能研究[D].陕西科技大学,2017.
[23]Lucas R,Comelles F,Alcantara D,et al.Surface-Active Properties of Lipophilic Antioxidants Tyrosol and Hydroxytyrosol Fatty Acid Esters:A Potential Explanation for the Nonlinear Hypothesis of the Antioxidant Activity in Oil-in-Water Emulsions[J].Journal of Agricultural and Food Chemistry,2010,58(13):8021-8026.
[24]秦树法,王芳,汤克勇,等.利用水解胶原蛋白制备多肽酰胺表面活性剂[J].中国皮革,2013,(09):13-15.
[25]栾俊.利用废革屑制备不同碳链长度N-酰基多肽表面活性剂及其性能研究[D].烟台大学,2016.
[26]Camacho N P,West P,Torzilli P A,et al.FTIR microscopic imaging of collagen and proteoglycan in bovine cartilage[J].Biopolymers,2015,62(1):1-8.
[27]Payne K J,Veis A.Fourier transform IR spectroscopy of collagen and gelatin solutions:deconvolution of the amide I band for conformational studies[J].Biopolymers,1988,27(11):1749.
[28]Quagliotto P,Montoneri E,Tambone F,et al.Chemicals from wastes:compost-derived humic acid-like matter as surfactant[J].Environmental Science and Technology,2006,40(5):1686-1692.
[29]王林林.N-中碳链脂肪酰基氨基酸盐的合成及表面活性研究[D].南昌大学,2013.