Describes the onset, peak, and duration of action of the commonly used insulins.
\r\n\tThis book is intended to provide a series of peer reviewed chapters that the guest editor believe will aid in increasing the quality of the research focus across the growing field of grain and seeds compound functionality research. Overall, the objective of this project is to serve as a reference book and as an excellent resource for students, researchers, and scientists interested and working in different functional aspects of grain and seed compounds, and particularly for the scientific community to encourage it to continue publishing their research findings on grain and seed and to provide basis for new research, and the area of sustainable crop production.
\r\n\t
The main aim of treatment of gestational diabetes is to prevent fetal, maternal, and neonatal complications. A randomized controlled trial which involved 1000 women with GDM showed that treatment of GDM is associated with the reduction of all neonatal complications, namely, birth injuries, shoulder dystocia, and perinatal morbidity and mortality. Treatment also reduced the rate of development of preeclampsia from 18 to 12% and the rate of large for gestational age (LGA) from 22 to 13% [1]. Even in women with mild GDM, treatment reduced the rate of LGA, the mass of neonatal fat, shoulder dystocia, cesarean section, and hypertensive disorders associating pregnancy [2, 3].
\nImproving the pregnancy outcome in women with GDM can be achieved through maintenance of fasting blood sugar levels <95 mg/dl (5.3 mmol/L), 1-h postprandial blood sugar <140 mg/dl (7.8 mmol/L), and 2-h postprandial blood sugar <120 mg/dl as recommended by both the American College of Obstetricians and Gynecologists (ACOG) and American Diabetes Association [4].
\nThe treatment of GDM starts with dietary modifications along with particular nutritional approaches [5, 6, 7] combined with exercise [8, 9]. If this combination failed to maintain the needed glucose levels, pharmacological treatment starts, regardless of the lines used for treatment, proper monitoring of maternal health, fetal condition, and blood sugar levels.
\nDietary counseling should be individualized according to women weight and height [10] through a registered dietitian [11].
\nJSOG committee on nutrient and metabolism problems described a caloric intake of 25–30 kcal/kg (+150 Kcal for the first half and + 350 kcal for the second half of pregnancy) [12].
\nThe Ministry of Health and Welfare recommended a caloric intake of 25–30 kcal/kg (+ 50,250 and 450 kcal for the first, second, and third trimester, respectively) [13].
\nThe ideal diet components are not yet determined. However excessive weight gain with postprandial hyperglycemia is commonly associated with diet that included 50–60% of carbohydrate. ACOG recommended the limitation of carbohydrate to 33–40% of the required calories and the remaining 60% to be gained from proteins (20%) and fats (40%) [4].
\nThe complex form of carbohydrates is preferable over simple ones as they are absorbed slower without producing significant hyperglycemia. Complex carbohydrates also decrease insulin resistance [6].
\nIf the routine three meals daily failed to achieve the target blood sugar, each meal should be divided in 2:1 or 1:1 ratio to eat 4–6 meals per day [14].
\nThe ADA recommended “MyPlate” as a healthy guide for each meal which consists of 25% protein, 25% starch, and 50% non-starchy foods as vegetables especially steamed ones. Creating MyPlate is a simple and effective method allowing proper control of the blood glucose levels and losing weight (
Some foods to be avoided include highly processed foods as white bread, fast foods, alcohol, baked products as muffins and cakes, sugary drinks, candy, and high starch foods as white rice and white potatoes.
\nAlthough there are many randomized studies done to evaluate the effects of physical exercise and lifestyle modifications in adults with diabetes, only few ones evaluated these effects in pregnant women with GDM. These studies proved that exercise improves the blood glucose [8, 15, 16, 17, 18]. These beneficial effects may occur as a result of the increase of lean muscle mass with subsequent increase in insulin sensitivity. So a moderate exercise program is highly recommended for women with GDM [11]. A moderate intensity aerobic exercise for at least 150 minutes weekly [19] or simple exercise as walking after each meal for 10–15 minutes [20] is recommended.
\nThe Finnish GDM prevention trial (RADIEL)—a multicenter randomized controlled study—evaluated the efficacy of combined dietary and physical activity modifications in prevention of GDM and obesity-related perinatal complications [21]. Counseling was achieved through three visits to the study nurse at 13, 23, and 35 weeks of pregnancy. Dietary modification was done according to Nordic Nutrition Recommendations encouraging the intake of vegetables, fruits and berries, high-fiber whole-grain products, low-fat dairy products, vegetable fats high in unsaturated fatty acids, and fish and low-fat meat products with lower intake of sugar- and saturated fatty acid-rich foods. [22]. Physical moderate exercise for 150 minutes at least per week is recommended [23]. They found that these modifications had no effects on either the incidence of GDM or perinatal complications [24].
\nPharmacologic treatment is indicated when dietary management and exercise failed to achieve the target glucose levels.
\nBasically, insulin is the standard treatment for GDM [11]. Insulin has the advantage of non-crossing of the placenta. It is given according to the timing of the occurrence of hyperglycemia. If hyperglycemia is present throughout the day both in the fasting and postprandial state, a divided dose of combination of either long or intermediate acting insulin with the short acting one is recommended. The typical total starting dose is 0.7–1 unit/ kg of body weight. If hyperglycemia is detected only at a specific times, focusing the insulin dose at that specific time of hyperglycemia is done, e.g., high fasting blood sugar is treated using a nighttime intermediate-acting insulin, while elevated post-breakfast blood sugar is treated by short-acting insulin before breakfast. The maintenance dose is then adjusted according to the monitored blood glucose [4].
\nThe insulin analogs as insulin aspart and lispro are preferred over the regular insulin as a short-acting type. They do not cross the placenta, and their main advantage is their faster onset of action allowing the women to receive their injection at the time of the meal not 10–15 minutes before it as needed in the regular type. This advantage provides better control of the glucose level, and less attacks of hypoglycemia resulted from timing error [25, 26]. Intermediate- and long-acting insulin include the basic isophane insulin (NPH) and recent insulin glargine and detemir (Table 1) [27, 28, 29].
\nType | \nOnset (min) | \nPeak (h) | \nDuration (h) | \n
---|---|---|---|
Insulin lispro | \n1–15 | \n1–2 | \n4–5 | \n
Insulin aspart | \n1–15 | \n1–2 | \n4–5 | \n
Regular insulin | \n30–60 | \n2–4 | \n6–8 | \n
Isophane insulin suspension (NPH) | \n60–180 | \n5–7 | \n13–18 | \n
Insulin glargine | \n60–120 | \nNo peak | \n24 | \n
Insulin detemir | \n60–180 | \nMinimal at 8–10 | \n18–26 | \n
Describes the onset, peak, and duration of action of the commonly used insulins.
Modified from Gabbe and Graves [30].
Historically oral hypoglycemics should be avoided as early agents cross the placenta, resulting in fetal hyperinsulinemia with subsequent macrosomia and congenital malformations (most commonly in the ear) and severe neonatal hypoglycemia. Now their use in GDM is increasing despite them not approved by the US Food and Drug Administration [31] and the recommendation of ADA that insulin is the first-line therapy for GDM [11] as these products have advantages as ease of tablet intake, ease of storage, and safe needle disposal.
\nOral antidiabetic medications include biguanides, sulfonylurea, acarbose, Guar gum, and thiazolidinedione.
\nMetformin is a biguanide that decreases intestinal glucose absorption and hepatic gluconeogenesis and increases peripheral glucose uptake. Historically, it was given to women used in pregestational diabetic women and women with polycystic ovary syndrome who suffer from infertility. In the latter group, it was continued until completion of the first trimester, despite the limited evidence of its ability to improve pregnancy outcome [32].
\nAlthough metformin can cross the placenta, its long-term metabolic effects on the growing fetus are not known [33]. One study showed the absence of any developmental effects till the age of 2 years of life [34].
\nIn a randomized controlled trial, 751 pregnant women having GDM were assigned to treatment with insulin or metformin ± insulin. The perinatal outcome was similar among the two groups [35].
\nAnother smaller trial showed that women assigned to metformin had lower blood glucose, lower maternal weight gain during pregnancy, and lower incidence of neonatal hypoglycemia [36].
\nIn a network meta-analysis that included unpublished trials, there was a difference between insulin and metformin treatments regarding neonatal birth weight, hypoglycemia, or mode of delivery [37].
\nTherefore, women with GDM are carefully counseled about the use of metformin. They should know that it is not superior to insulin, there are no definitive data about its long-term effects of the growing fetus, and 26–46% of women on metformin will need to add insulin to replace it or to potentiate its effects for better glucose control [35, 36].
\nMetformin starting dose is usually 500 mg once daily at nighttime for 1 week, and then the dose is increased according to the response. The maximum daily dose is 2500–3000 mg daily in two–three divided doses.
\nContraindications to metformin include impaired kidney function, and serum creatinine should be evaluated before the start of treatment.
\nSide effects of metformin occur in 2.5–45.7% of cases [38], and the commonest is GIT upset in the form of abdominal pain and diarrhea. Its use may be associated with higher rate of lactic acidosis, preeclampsia, and neonatal jaundice. So the drug is instructed to be administered with meals and to increase the needed dose gradually.
\nA systematic review stated that metformin use during pregnancy is safe and effective regarding the short-term pregnancy outcomes. There are no solid guidelines about the duration of metformin use during pregnancy, so it is based on clinical experience on a case-by-case basis [39].
\nSulfonylurea used in GDM includes glyburide, tolbutamide, glibenclamide, and gliclazide. Chlorpropamide crosses, while glibenclamide does not cross the placenta.
\nGlyburide augments insulin secretion by pancreas (through binding adenosine triphosphate potassium channel receptors of the beta cells) and extrapancreatic tissues. It also increases insulin sensitivity of peripheral tissues. It should not be used as a first-line treatment as most studies showed inferior results when compared to insulin or metformin [31].
\nThe dose of glyburide is 2.5–20 mg per day in divided doses. The maximum dose is 30 mg daily [40]. Even with these high doses, 4–16% of patients will need the addition of insulin for adequate glycemic control [41, 42, 43, 44].
\nContraindications include allergy to sulfa, and side effects include mild infrequent GIT side effects as nausea, vomiting, and diarrhea.
\nAlthough some individual trials showed no difference regarding blood glucose control between glyburide and insulin [41, 42, 43, 44, 45, 46], meta-analyses reported higher incidence of macrosomia, maternal, and neonatal hypoglycemia [35, 36, 47]. Other trials found that women used glyburide and had higher incidence of hypertension, hyperbilirubinemia, and still birth than those on insulin therapy [31, 42, 48, 49, 50, 51, 52].
\nOther sulfonylurea include Thiazolidinedione as Pioglitazone & Rosiglitazone which decrease insulin resistance by reducing RESISTIN hormone released from adipose tissue. Their use during pregnancy cannot be recommended as no enough reports to support their use.
\nA Cochrane meta-analysis evaluated 7381 women with GDM and reported similar pregnancy outcomes when insulin therapy is compared with oral antidiabetic agents (metformin, glyburide, both, and acarbose) [53]. However these oral antidiabetic agents have different safety and efficacy, so pooling all of them together against insulin weakens that meta-analysis.
\nTo sum up, the current available data show the absence of short-term hazards, but the long-term effects are still unknown. So, the women should be counseled about the unknown proven safety of the oral antidiabetic agents and the high rate of need for adding insulin before describing it.
\nACOG considers insulin as the first-line treatment for GDM and describes oral agents (mainly metformin and rarely glyburide) as an alternative in women who decline insulin use (for financial issues or non-availability of safe administration) after proper consultation.
\nAs there are many evidences that link oxidative stress and development of complications of diabetes with pregnancy, the use of antioxidants was suggested to improve pregnancy outcome [54]. Oxygen free radicals released during aerobic metabolism cause cellular damage [55, 56]. Many authors reported the participation of reactive oxygen species in diabetes associated with pregnancy [57, 58].
\nAn interesting randomized controlled trial was conducted that involved 200 women with GDM who were assigned to receive antioxidant (1 gram L-ascorbic acid daily) or placebo. Maged and colleagues found that antioxidants significantly decreased the required insulin dose to control blood sugar and oxidative markers (glutathione, malondialdehyde, superoxide dismutase). In placental tissue homogenate, maternal blood and neonatal blood were significantly different between the two groups. In the antioxidant group, the neonatal blood sugar was more stable within 2 h of delivery, and the neonatal ICU admission was lower than other women. They concluded that the use of antioxidant administration during pregnancy in women with GDM reverses the oxidative stresses resulting in the improvement of neonatal outcome [59].
\nMonitoring of glucose control is through blood testing urine analysis for glucose and ketone bodies and glycosylated hemoglobin.
\nThe optimal frequency of blood glucose testing in women with GDM is not known. However, four evaluations daily seem to be satisfactory (fasting and after each meal) [4].
\nFasting blood sugar is predictive of neonatal fat mass and subsequent development of childhood obesity and diabetes [60], and 1-h postprandial level was predictive of better blood sugar control and subsequent development of LGA and cesarean delivery [61], so both should be measured. The postprandial measurement can be after 1 or 2 h as the peak glucose level occurs almost 90 min after meals [62]. Measurement neither at 1 h nor at 2 h is superior to the other [63, 64, 65].
\nAfter stabilization of the blood sugar, individualization of the frequency of glucose measurement according to the gestational age, adherence of the patient to treatment and the needs of further adjustment is recommended. However the minimum is two measurements per day [4].
\nWomen under self-monitoring of blood glucose daily had significantly lower incidence of fetal macrosomia and less weight gain than those under intermittent measurement of fasting glucose during semi-weekly antenatal visits [66].
\nde Veciana and colleagues randomly assigned 66 women with GDM for preprandial or 1-h postprandial measurement of blood sugar. They found that postprandial group had better blood glucose control with less macrosomia, cesarean delivery for cephalopelvic disproportion, and neonatal hypoglycemia [61].
\nA review included 10 trials of 538 women (468 and 70 women with type 1 and type 2 diabetes). Different glucose monitoring methods were compared without clear advantage of one method over the others. Two trials (43 women) comparing self-monitoring versus standard care proved no difference for cesarean section or glycemic control. One study (100 women) compared self-monitoring versus hospitalization and found no clear difference for hypertensive disorders, cesarean section, or preterm birth. Another study (61 women) which compared preprandial versus postprandial glucose monitoring proved no clear difference regarding cesarean section, macrosomia, or glycemic control. Three studies (84 women) which compared automated telemedicine monitoring versus conventional system found no clear difference for cesarean section and mortality or morbidity. CGM was compared to intermittent monitoring in two studies (225 women), and there was no difference for preeclampsia and cesarean section and large for gestational age. One trial (25 women) compared constant CGM versus intermittent CGM and found no clear difference between groups for cesarean section, glycemic control, or preterm birth [67].
\nHemoglobin (Hb) A forms about 90% of hemoglobin in adults, and its glycosylation occurs due to irreversible nonenzymatic binding of glucose to N-terminal of β chain. Hb A1 is divided into Hb A1 a1, Hb A1 a2, Hb A1 b, and Hb A1 C (the most important). The mean plasma glucose over the erythrocyte life span is correlated with the degree of glycosylation. Its advantages include that it is a single, non-fluctuating blood test that reflects the glucose levels over the last 4–8 weeks. So, HbA1c is an attractive test that can be added to routine investigations done in the first antenatal evaluation as it serves as a diagnostic tool for women with undiagnosed diabetes or at risk of its development [68]. If measured during the first trimester, it gives an idea about blood glucose control in the periconceptional period and during organogenesis. Its main disadvantage is its affection by red blood cell turnover [6] which results in the absence of clear recommendations for its use to diagnose GDM [69, 70, 71]. HbA1C increases also in cases of non-hemolytic anemias and chronic renal failure [72]. Women with A1c of 10–12% have up to a 25% risk of major malformations.
\nLike women with pregestational diabetes, women with GDM should follow antenatal fetal assessment especially those with poor glycemic control and women under medical treatment with insulin or oral antidiabetic agents [73]. It should start at 32 weeks of gestational age and earlier in women with GDM associated with other factors that may adversely affect fetal outcome as hypertensive disorders [74].
\nThere is no consensus about antepartum fetal monitoring in properly controlled women without medical treatment, and if done it usually starts to alter at 32 weeks. The specific test used and its frequency are dependent on the regional practice, but amniotic fluid measurement is probably included as polyhydramnios is commonly associated with fetal hyperglycemia [4].
\nAt Parkland Hospital, women with GDM are routinely asked to count daily fetal kick especially during the third trimester, and women on insulin treatment are offered for hospital admission and CTG monitoring three times weekly [74].
\nTiming and management of delivery of women with GDM are dependent on glycemic control, fetal condition, and associated complications. Women with proper glycemic control without associated medical problems are followed up till term [75, 76].
\nA comparison was done between women with GDM who were subjected to labor induction at 38 weeks and those who were followed up till 41 weeks of gestation, which revealed similar CS rate and all other outcomes except the higher occurrence of neonatal hyperbilirubinemia in one study [77], lower incidence of LGA in another study [78], and lower incidence of shoulder dystocia in a third one [79] in the induction group. A more recent study found a lower rate of CS in the induction group [80]. So women with GDM using medications with proper control of blood sugar delivered better during the 39 weeks of gestation [4].
\nIn women with poor control of their blood sugar, timing of delivery is determined by balancing the risk of prematurity and the ongoing risk of intrauterine fetal death. In general earlier delivery in women with good glycemic control is recommended [75, 76], but the clear guides for glycemic control and timing of delivery are absent [81]. In general delivery between the start of 37 weeks and the completion of 38 weeks appears appropriate, while delivery at 34 weeks till the completed 36 weeks should be attempted only in women with abnormal fetal well-being assessment and those with failed hospital control of blood sugar [4].
\nUltrasound assessment of fetal size should be done in all women with GDM. However only 22% of fetuses diagnosed as LGA by ultrasound had macrosomia after birth [82]. To prevent one case of permanent brachial plexus injury, 588 and 962 CS should be performed for ultrasonographic estimated fetal weight of 4500 and 4000 gm, respectively [83, 84]. So women with GDM and macrosomic fetus should be counseled about the elective CS risks and benefits [85].
\nWomen with GDM should be evaluated postpartum as 15–70% will develop diabetes later in life [86, 87, 88, 89, 90]. These women were estimated to have sevenfold increased risk of developing type 2 DM when compared to controls [91]. So, screening after 4–12 weeks of delivery is recommended to identify those with diabetes, impaired fasting glucose levels, or impaired glucose tolerance [11] (Figure 1).
\nManagement of postpartum screening results. Abbreviations: FPG, fasting plasma glucose, OGTT, oral glucose tolerance test; IGT, impaired glucose tolerance.
ACOG practice bulletin No. 190: Gestational diabetes mellitus [4].
\nThe Fifth International Workshop-Conference on Gestational Diabetes recommended that women with GDM undergo evaluation with a 75-g oral glucose tolerance test at 6–12 weeks postpartum [92]. These recommendations are shown in Table 2.
\nTime | \nTest | \nPurpose | \n
---|---|---|
Post-delivery 1–3 days | \nFasting or random plasma glucose | \nDetect persistent, overt diabetes | \n
Early postpartum (6–12 week) | \n75 g, 2-h OGTT | \nPostpartum classification of glucose metabolism | \n
1-year postpartum | \n75 g, 2-h OGTT | \nAssess glucose metabolism | \n
Annually | \nFasting plasma glucose | \nAssess glucose metabolism | \n
Triannually | \n75 g, 2-h OGTT | \nAssess glucose metabolism | \n
Prepregnancy | \n75 g, 2-h OGTT | \nClassify glucose metabolism | \n
Fifth international workshop-conference: Metabolic assessments recommended after pregnancy with gestational diabetes.
Metzger et al. [92].
Women with GDM are at an increased risk for cardiovascular complications associated with dyslipidemia, hypertension, and abdominal obesity—the metabolic syndrome [74].
\nKessous and colleagues found that women with GDM were 2.6 times more likely to be hospitalized for cardiovascular morbidity [93].
\nShah and coworkers also reported excessive cardiovascular disease by 10 years in women with GDM [94].
\nThe risk of recurrence of GDM is estimated to be 40% in primiparous women [95]. Women with higher body mass index are more likely to have impaired glucose tolerance in subsequent pregnancies. Therefore, lifestyle modifications, including weight control and exercise between pregnancies, may prevent the recurrence of GDM [96]. Overweight and obese women in their first pregnancy will lower the risk of GDM, if they lose 2 or more units of their body mass index [97]. The risk of GDM in second pregnancy was 4.2% in women without GDM in their first pregnancy against 41.3 percent in those with a history of gestational diabetes in their first pregnancy [98].
\nWomen with recent GDM can use low-dose hormonal contraceptives safely as the rate of developing of diabetes is similar in oral contraceptive users and nonusers of any hormonal contraception [99]. Care should be taken in women at risk of cardiovascular diseases as obese, hypertensive, and dyslipidemic women with direction of the contraceptive choice toward a method without potential cardiovascular consequences as intrauterine device.
\nStudies were reviewed and evaluated for quality according to the method outlined by the US Preventive Services Task Force:
\nI Evidence obtained from at least one properly designed randomized controlled trial.
\nII-1 Evidence obtained from well-designed controlled trials without randomization.
\nII-2 Evidence obtained from well-designed cohort or case–control analytic studies, preferably from more than one center or research group.
\nII-3 Evidence obtained from multiple time series with or without the intervention. Dramatic results in uncontrolled experiments also could be regarded as this type of evidence.
\nIII Opinions of respected authorities, based on clinical experience, descriptive studies, or reports of expert committees.
\nToday, the term “functional polymers” is used to compare the specific properties such as chemical, physicochemical or biochemical functions of polymeric materials and to classify polymers in this field. For the preparation of different purpose polymers, new monomers are obtained by binding the functional group to the structure of certain monomers. Copolymers of commercial monomers and monomers with functional groups are prepared and their properties are investigated. In addition, chemical polymers are chemically modified and functional groups are bonded to produce chemical-reactive polymers in both the industry and polymer-based chemistry. The application of chemical modification to the polymers is used to prepare polymers which cannot be prepared by direct polymerization of the monomer.
There are two ways to synthesize a polymer with the planned pendant reactive group: (1) functionalization of a non-functional polymer by chemical modification; (2) binding of a reactive side group to the monomer and polymerization of this reactive group monomer by chain addition polymerization methods [1]. Both methods have been successfully applied to obtain vinyl polymers. The synthesis and studies on (meth)acrylate polymers have attracted the attention of various groups in recently [2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13]. Acrylate homopolymers along with their copolymers are used in various fields such as thin films, adsorption, fibers, filament coatings, lithography, lacquers, adhesives, printing inks, and binders [14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34].
There are some disadvantages in linking functional groups on polymers:
The distribution of bound functional groups on polymer molecules may not be regular.
The density of the bound reactive groups is generally low, and therefore, in such polymers, there may be no results in terms of reaction between the functional group and the polymer structure.
Polymer functionalization reactions should be carried out in temperate conditions and the efficiency of the reactions should be quantitative. Because it will be a part of the polymer chain in the undesirable groups that may occur by side reactions. Therefore, precautions should be taken in such a way that no side reactions occur as long as possible.
The activity of the groups to be bound on the polymer molecules may be different due to the surrounding of the macromolecule compared to similar small molecules. Therefore, more characteristic reaction conditions may be required for a satisfactory transformation.
Side reactions during the polymer functionalization reaction will produce impurities in the obtained polymer due to unreacted groups and other functional groups, which will reveal the problem of purification.
Due to undesirable side reactions, the chemical and physical properties of the polymer, such as dissolution, cross-linking, halogen and gas release, can be varied.
Since the functional groups allow for cross-linking during polymerization and the polymer will not dissolve, there may not be sufficient analytical methods to investigate the properties of the polymer.
In particular, where the polymer chain is susceptible to chemical reactions, reactions should be carried out without degradation.
The oxirane compound is obtained from the epichlorohydrin with an arylalcohol. The synthesis reaction scheme is given in Figure 1.
Reaction scheme of aryloxy-2,3-epoxy propane.
A typical procedure for the reaction of arylalcohol with epichlorohydrin is as follows: arylalcohol (0.5 mol) and epichlorohydrin (1.5 mol) and sodium hydroxide (0.55 mol) are mixed with magnetic stirrer at 50°C for 10 h, and then the reaction mixture is stirred at room temperature for 15 h. The organic layer is washed several times with diethylether and dried over magnesium sulfate. After removing diethylether, the excess of epichlorohydrin is distilled at 50°C and 60 mmHg. The remaining reaction mixture is distilled at 110°C and 12 mmHg (oxirane product yield: 87%). The structure of the compound aryloxy-2,3-epoxy propane is identified by the FT-IR techniques. FT-IR (cm−1): 3100–2800 (C▬H); 1590 (C〓C); 1250 (epoxy C▬O); 950–770 (epoxy C▬H).
Oxirane compound is distilled off again at 110°C and 12 mmHg by vacuum distillation. In a reaction flask, 0.26 mol of oxirane, 0.54 mole of methacrylic acid, 0.30 mol of pyridine, and 100 ppm of hydroquinone are mixed in 200 ml of toluene solvent at 85°C for 24 h with a magnetic stirrer. After the reaction is complete, 30% sodium hydroxide solution is added until the mixture is taken up in ethereal separation funnel and basic. The basic aqueous phase obtained at the end of the extraction is extracted three times with diethylether in another separating funnel. The collected ethereal phases are taken to the separating funnel and extracted until neutral with water. The etheric phases are taken into a collection container and a sufficient amount of anhydrous magnesium sulfate is thrown into it and left to dry for 24 h. At the end of the filtration process, the mixture separated from magnesium sulfate is distilled off the toluene at 45°C and 50 mmHg. To the remaining mixture, 50 ppm of hydroquinone was added and vacuum distillation is carried out with monomer at 150°C and 1 mmHg (monomer yield: 65%). The synthesis reaction scheme is given in Figure 2.
Reaction scheme of aryloxy-2-hydroxypropyl methacrylate monomer.
The structure of the monomer is confirmed by the FT-IR and 1H- and 13C-NMR spectroscopic techniques. FT-IR (cm−1): 3600–3200 (▬OH); 3100–2800 (C▬H); 1720 (>C〓O); 1630 (CH2〓C); 1580 (aromatic, C〓C); 1250 (C▬O). 1H-NMR (CDCl3, TMS): 8.0–6.8 (aromatics ▬H); 6.2–5.44 (CH2〓C); 4.25 (O▬H); 1.8 (CH3). 13C-NMR (CDCl3, TMS): 157.2–113.8 (aromatics ▬
Appropriate amounts of aryloxy-2-hydroxypropyl methacrylate monomer and chloroform and 2,2′-azobisisobutyronitrile (AIBN) as an initiator (2% of the monomer mass) are disposed in a polymerization tube and liquidated with nitrogen for 10 min. The sealed and waxed polymerization reaction tube is placed at 60 ± 1°C for 24 h in oil bath. The reaction product is poured dropwise into an abundant of diethylether. The obtained polymer is purified by re-precipitation with diethylether from a chloroform solution and the latest operation dried under vacuum oven (conversion 90%). The synthesis reaction scheme is given in Figure 3.
Reaction scheme of poly aryloxy-2-hydroxypropyl methacrylate.
The formation of the homopolymer of aryloxy-2-hydroxypropyl methacrylate is confirmed by the FT-IR and 1H-NMR spectroscopic techniques. The main description for the polymerization of the monomer is that the characteristic double bond (vinyl structure double bond) peak signal of the monomer in the FT-IR spectrum is fully depleted and does not peak in this region in the FT-IR spectrum of the polymer. This is because the addition polymerization proceeds through the opening of the pi bond in the vinyl group. This has been effectively observed in the synthesis and characterizations herein. Two signals altered in the FT-IR spectrum of the monomer: the stretching vibration band of the vinyl group C〓C at 1630 cm−1 and the absorption signal at 920 cm−1 assigned to the C▬H bending of geminal〓CH2.
The information is clearly seen in 1H-NMR spectroscopy on polymer formation. The formation of polymer is clearly evident from the disappearing of the two singlets at 6.3 and 5.4 ppm of the vinyl protons and the wide peaks at 2.4–1.3 ppm due to the conversion to the aliphatic ▬CH2 group.
Arylacetyl chloride is prepared by reacting arylalcohol with chloroacetyl chloride using the K2CO3. A typical procedure for the acylation reaction of arylalcohol with chloroacetyl chloride is as follows: arylalcohol (1 mol) and K2CO3 are dissolved in 20 ml of anhydrous benzene at 0°C, and then 1.1 mol of chloroacetyl-chloride is added dropwise to this solution. The reaction mixture is stirred at room temperature for 15 h. The organic layer is washed several times with diethylether and dried over MgSO4. After removing diethylether, α-chloro-arylacetamide is crystallized from methanol (yield: 80%). The structure of the compound arylacetylhalide is identified by the FT-IR techniques. FT-IR (cm−1): 3100–2800 (C▬H); 1730 (>C〓O); 1580 (aromatic, C〓C). The synthesis reaction scheme is given in Figure 4.
Reaction scheme of arylacetylhalide.
Aryloxycarbonyl methyl methacrylate is synthesized as follows: a mixture of arylacetyl chloride (1 mol), sodium methacrylate (1.1 mol) in 100 ml acetonitrile and triethylbenzylammonium chloride (TEBAC) (0.1 mol) as a phase transfer catalyst better and sodium iodide (NaI) (0.1 mol) as catalyst are receipt in a three-neck round bottom flask equipped with a thermometer, magnetic stirrer, and heated to 85°C in a reflux condenser in the presence of 100 ppm hydroquinone. The reaction is continued for an additional 30 h. The reaction mixture is cooled to 20°C and moved to a separating funnel, washed sequentially with diethylether, 5% NaOH, and distilled water. The organic layer are spooled and dried over anhydrous magnesium sulfate (MgSO4) for 24 h. Magnesium sulfate is filtered and the diethylether is removed from the organic layers with a rotary evaporator. The resulting monomer is purified by recrystallization from ethanol (yield: 85%). The synthesis reaction scheme is given in Figure 5.
Reaction scheme of aryloxycarbonyl methyl methacrylate monomer.
The structure of the monomer is confirmed by the FT-IR and 1H- and 13C-NMR spectroscopic techniques. FT-IR (cm−1): 3100–2800 (C▬H); 1730 (>C〓O); 1630 (CH2〓C); 1580 (aromatic, C〓C); 1250 (C▬O). 1H-NMR (CDCl3, TMS): 7.9–6.6 (aromatics ▬H); 6.2–5.41 (CH2〓C); 1.8 (CH3). 13C-NMR (CDCl3, TMS): 157.1–113.4 (aromatics ▬
Homopolymer of aryloxycarbonyl methyl methacrylate is synthesized using 2,2′-azobisisobutyronitrile (AIBN) as an initiator (2% of the monomer mass) in 1,4-dioxane solution. The reaction mixture is de-aerated by passing nitrogen gas for 10 min, then the tube is tightly sealed and kept in a thermostatic oil bath at 60 ± 1°C for 24 h. The homopolymer is precipitated in excess methanol, purified by dissolution in 1,4-dioxane and reprecipitation in methanol. The homopolymer is dried in vacuum to constant weight (conversion 90%). The synthesis reaction path is given in Figure 6.
Reaction scheme of poly aryloxycarbonyl methyl methacrylate.
The formation of the homopolymer of aryloxycarbonyl methyl methacrylate is confirmed by the 1H-NMR and FT-IR spectroscopic techniques. The information is clearly seen in 1H-NMR spectroscopy on polymer formation. The formation of polymer is clearly evident from the disappearing of the two singlets at 6.3 and 5.4 ppm of the vinyl protons and the wide peaks at 2.4–1.3 ppm due to the conversion to the aliphatic-CH2 group. The main description of the polymer is exactly the extinction of some characteristic peaks of the double bond in the FT-IR spectrum, and this has been effectively observed in the synthesis and characterizations herein. Two signals altered in the FT-IR spectrum of the monomer: the stretching vibration band of the vinyl group C〓C at 1630 cm−1 and the absorption signal at 920 cm−1 assigned to the C▬H bending of geminal〓CH2.
α-chloro-N-arylacetamide is prepared by reacting arylamine with chloroacetylchloride using the K2CO3. A typical procedure is as follows: arylamine (1 mol) and K2CO3 were dissolved in 20 ml of anhydrous benzene at 0°C, and then 1.1 mol of chloroacetylchloride are added dropwise to this solution. The reaction mixture is stirred at room temperature for 15 h. The organic phase is washed several times with diethylether and dried over MgSO4. After removing diethylether, α-chloro-N-arylacetamide is crystallized from methanol (yield: 80%). The synthesis reaction scheme is given in Figure 7.
Reaction scheme of α-chloro-N-arylacetamide.
The structure of the compound α-chloro-N-arylacetamide is identified by the FT-IR techniques. FT-IR (cm−1): 3340 (NH); 3100–2800 (C▬H); 1680 (>C〓O); 1580 (aromatic, C〓C).
Arylamido methyl methacrylate is synthesized as follows: 1.1 mol sodium methacrylate, 1 mol α-chloroacetamide, 0.1 mol NaI and 0.1 mol TEBAC and as catalyst are stirred in 100 ml acetonitrile at 80°C in a reflux condenser for 30 h in the presence of 100 ppm hydroquinone. After the solution is cooled to 20°C and neutralized with a 5% NaOH solution. The organic phase is washed a few times with water, and the water phase is washed with diethylether a several times. The diethyl ether phase and the acetonitrile phase are spooled and dried over anhydrous magnesium sulfate for 24 h. Diethyl ether and acetonitrile are removed with a rotary evaporator. The organic phases are collected and the residue is distilled at 130°C at 5 mmHg to give a colorless liquid (yield: 80%). The synthesis reaction scheme is given in Figure 8.
Reaction scheme of arylamido methyl methacrylate monomer.
The structure of the monomer is confirmed by the FT-IR and 1H- and 13C-NMR spectroscopic techniques. FT-IR (cm−1): 3325 (NH); 3100–2800 (C▬H); 1680 (>C〓O); 1630 (CH2〓C); 1580 (aromatic, C〓C); 1230 (C▬O▬C). 1H-NMR (CDCl3, TMS): 9.1 (N▬H); 8.0–6.7 (aromatics ▬H); 6.3–5.43 (CH2〓C); 1.8 (CH3). 13C-NMR (CDCl3, TMS): 157.1–113.4 (aromatics ▬
Arylamido methyl methacrylate monomer is freed from inhibitor by washing with a dilute KOH solution followed by distilled water and then drying over MgSO4. Appropriate amounts of arylamido methyl methacrylate monomer, 2,2′-azobisisobutyronitrile (AIBN) (2% of the monomer mass) and 1,4-dioxane are placed in a polymerization reaction tube and purged with nitrogen for 15 min. The closed mouth polymerization reaction tube is kept at 60 ± 1°C for 30 h in oil bath. The reaction product is poured dropwise into an abundant of n-hexane. The obtained polymer is purified by re-precipitation with n-hexane from a 1,4-dioxane solution and the latest operation dried under vacuum oven (conversion 90%). The synthesis reaction scheme is given in Figure 9.
Reaction scheme of poly arylamido methyl methacrylate.
The structure of poly arylamido methyl methacrylate is confirmed by the FT-IR and 1H-NMR spectroscopic techniques. The main description for the polymerization of the monomer is that the characteristic double bond (vinyl structure double bond) peak signal of the monomer in the FT-IR spectrum is fully depleted and does not peak in this region in the FT-IR spectrum of the polymer. This is because the addition polymerization proceeds through the opening of the pi bond in the vinyl group. This has been effectively observed in the synthesis and characterizations herein. Two signals altered in the FT-IR spectrum of the monomer: the stretching vibration band of the vinyl group C〓C at 1630 cm−1 and the absorption signal at 920 cm−1 assigned to the C▬H bending of geminal〓CH2.
The information is clearly seen in 1H-NMR spectroscopy on polymer formation. The formation of polymer is clearly evident from the disappearing of the two singlets at 6.3 and 5.4 ppm of the vinyl protons and the wide peaks at 2.8–1.4 ppm due to the conversion to the aliphatic ▬CH2 group.
(Aryl-1,3-dioxalan-4-yl)methanol is prepared by reacting arylaldehyde with glycerin using the p-toluenesulfonic acid as catalyst. A typical procedure is as follows: Arylaldehyde (0.1 mol), glycerin (0.1 mol), p-toluenesulfonic acid (p-TOS) (0.5 g, as catalyst) and toluene (30 mL) are placed in a 100 mL three-necked reaction balloon fitted with a thermometer, condenser and a stirrer. The reaction mixture is refluxed at 115°C for 2 h with strong mixing. The reaction mixture is extracted a few times with diethyl ether and then 5% KOH solution, diethyl ether and toluene, respectively. The diethyl ether and toluene solvents are evaporated with rotary evaporator. The raw product is washed with water (40 mL × 3) and dried over anhydrous magnesium sulfate at overnight. The synthesis reaction scheme is given in Figure 10.
Reaction scheme of (aryl-1,3-dioxolane-4-yl) methanol.
The structure of (aryl-1,3-dioxolane-4-yl) methanol is identified by the FT-IR and 1H- and 13C-NMR spectroscopic techniques. FT-IR (cm−1): 3500–3110 (O▬H); 3100–2800 (C▬H); 1570 (aromatic, C〓C); 1180 (C▬O▬C). 1H-NMR (CDCl3, TMS): 7.48–7.0 (aromatics ▬H); 6.3–5.52 (CH2〓C); 4.0–3.7 (▬O▬CH); 4.17–4.11 (O▬CH2); 3.16 (▬OH), 3.0 (CH2). 13C-NMR (CDCl3, TMS): 151.1–116.4 (aromatics ▬
(Aryl-1,3-dioxalan-4-yl)methanol (0.1 mol), triethyl amine (NR3) (20 mL, as catalyst) and diethyl ether (40 mL) are filled in a 250 mL four-necked reaction balloon fitted with a thermometer, a condenser, a stirrer and an addition funnel including 15 mL acryloyl chloride. The acryloyl chloride is added drop wise to the solution with a dropping funnel. The temperature of the reaction mixture is hold by a cryostat at −5°C for 18 h. The reaction mixture is extracted a few times with 5% KOH solution and after dried over anhydrous magnesium sulfate for 24 h. The solvents are removed by the vacuum evaporator. The synthesis reaction scheme is given in Figure 11.
Reaction scheme of (aryl-1,3-dioxolane-4-yl) methyl acrylate monomer.
The structure of (aryl-1,3-dioxolane-4-yl) methyl acrylate is confirmed by the FT-IR and 1H- and 13C-NMR spectroscopic techniques. FT-IR (cm−1): 3100–2800 (C▬H); 1727 (>C〓O); 1630 (CH2〓C); 1570 (aromatic, C〓C); 1190 (C▬O▬C). 1H-NMR (CDCl3, TMS): 7.6–7.0 (aromatics ▬H); 6.3–5.52 (CH2〓C); 5.8 (Ar▬CH); 4.2–3.8 (▬O▬CH); 4.2–4.1 (O▬CH2); 3.0 (CH2). 13C-NMR (CDCl3, TMS): 166.2 (>
Free radical polymerization reaction of (aryl-1,3-dioxolane-4-yl) methyl acrylate monomer is conducted in a polymerization reaction tube using 2,2′-azobisisobutyronitrile (AIBN) (1% of the monomer mass) as initiator in 10 mL of 1,4-dioxane, at 65°C with 90% conversion in 6 h. The formed polymer is precipitated in ethyl alcohol. The obtained polymer is dried under vacuum at 45°C for 24 h for constant weight. The synthesis reaction scheme is given in Figure 12.
Reaction scheme of poly(aryl-1,3-dioxolane-4-yl) methyl acrylate.
The structure of poly(aryl-1,3-dioxolane-4-yl) methyl acrylate is confirmed by the FT-IR and 1H-NMR spectroscopic techniques. The information is clearly seen in 1H-NMR spectroscopy on polymer formation. The formation of polymer is clearly evident from the disappearing of the two singlets at 6.3 and 5.42 ppm of the vinyl protons and the wide peaks at 2.9–1.5 ppm due to the conversion to the aliphatic ▬CH2 group. The main description of the polymer is exactly the extinction of some characteristic peaks of the double bond in the FT-IR spectrum, and this has been effectively observed in the synthesis and characterizations herein. Two signals altered in the FT-IR spectrum of the monomer: the stretching vibration band of the vinyl group C〓C at 1630 cm−1 and the absorption signal at 920 cm−1 assigned to the C▬H bending of geminal〓CH2.
Synthesis of acetyl benzofuran is as follows: Potassium carbonate (K2CO3) (0.1 mol) and 2-hydroxybenzaldehyde (1 mol) are dissolved in 30 ml of absolute acetone. The reaction mixture is taken in a three-neck round bottom reaction balloon equipped with a magnetic stirrer, a thermometer, and cooled to 0°C. After then chloroacetone (1.1 mol) are added dropwise to this solution at 5°C, and stirred at 20°C for 16 h. The organic phase is washed a few times with distilled water and separation layer is filtered through filter paper and dried over anhydrous MgSO4 overnight. Acetyl benzofuran compound is crystallized from ethyl alcohol. Yield: 85%. The synthesis reaction scheme is given in Figure 13.
Reaction scheme of acetyl benzofuran.
The structure of acetyl benzofuran is identified by the FT-IR techniques. FT-IR (cm−1): 3100–2800 (C▬H); 1690 (>C〓O); 1570 (aromatic, C〓C).
Acetyl benzofuran (1 mol) is dissolved in 200 mL acetic acid, and after then bromo is added dropwise to this solution at 25°C for 2 h. After bromination reaction, the mixture is divided into ice-water. The separation layer is filtered through filter paper and dried over anhydrous magnesium sulfate (MgSO4) overnight. Bromo-acetyl benzofuran compound is crystallized from ethyl alcohol. Yield: 85%. The synthesis reaction scheme is given in Figure 14.
Reaction scheme of bromo acetyl benzofuran.
The structure of bromo acetyl benzofuran is identified by the FT-IR techniques. FT-IR (cm−1): 3100–2800 (C▬H); 1690 (>C〓O); 1570 (aromatic, C〓C); 780 (CH▬Br).
Sodium methacrylate (1.1 mol), bromo-acetyl benzofuran (1 mol), sodium iodide (0.1 mol) and triethylbenzylammoniumchloride (TEBAC) (0.1 mol) as catalyst are mixed in 100 mL acetonitrile at 70°C in a reflux condenser for 20 h in the beside of 100 ppm hydroquinone as an inhibitor. After then the solution is cooled to 20°C and neutralized with a 5% NaOH solution. The organic phase is washed with diethyl ether a few times. The diethyl ether and acetonitrile layers are spooled and dried over anhydrous magnesium sulfate (MgSO4) overnight. Diethyl ether and acetonitrile are evaporated with a rotary evaporator. The organic layers are collected and the residue is crystallized from ethyl alcohol. Yield: 80%. The synthesis reaction scheme is given in Figure 15.
Reaction scheme of acetyl benzofuryl methyl methacrylate monomer.
The structure of acetyl benzofuryl methyl methacrylate is confirmed by the FT-IR and 1H- and 13C-NMR spectroscopic techniques. FT-IR (cm−1): 3100–2800 (C▬H); 1735 (>C〓O); 1685 (▬C〓O); 1630 (CH2〓C); 1580 (aromatic, C〓C); 1190 (C▬O▬C). 1H-NMR (CDCl3, TMS): 7.7–7.2 (aromatics ▬H); 6.3–5.48 (CH2〓C); 4.2–4.0 (O▬CH2); 1.5 (CH3). 13C-NMR (CDCl3, TMS): 178.2 (▬
The preparation of homopolymer of Acetyl benzofuryl methyl methacrylate monomer is synthesized by free radical polymerization in 1,4-dioxane solvent using 2,2′-azobisisobutyronitrile (AIBN) as a free radical initiator. The homopolymer is purified by repeated reprecipitation from 1,4-dioxane and then filtered and dried until a constant weight is attained. The synthesis reaction path is given in Figure 16.
Reaction scheme of poly acetyl benzofuryl methyl methacrylate.
The structure of poly acetyl benzofuryl methyl methacrylate is confirmed by the FT-IR and 1H-NMR spectroscopic techniques. The information is clearly seen in 1H-NMR spectroscopy on polymer formation. The formation of polymer is clearly evident from the disappearing of the two singlets at 6.3 and 5.42 ppm of the vinyl protons and the wide peaks at 2.9–1.5 ppm due to the conversion to the aliphatic ▬CH2 group. The main description of the polymer is exactly the extinction of some characteristic peaks of the double bond in the FT-IR spectrum, and this real is effectively identified herein. Two signals altered in the FT-IR spectrum of the monomer: the stretching vibration band of the vinyl group C〓C at 1630 cm−1 and the absorption signal at 920 cm−1 assigned to the C▬H bending of geminal〓CH2.
Substituted benzaldehyde (1 mol) and substituted acetophenone (1 mol) are dissolved in 50 mL of ethyl alcohol and cooled at 18°C. An aqueous NaOH solution (1 mol in 40 mL of distilled water) is then added dropwise with constant mixing and as keeping the temperature constant at 18°C. After stirring the reaction mixture for 12 h at 20°C, it is neutralized with dilute HCl to isolate the compound. The obtained solid matter is filtered through filter paper, washed with ice cold water, dried and recrystallized from ethyl alcohol. Yield: 75%. The synthesis reaction scheme is given in Figure 17.
Reaction scheme of hydroxyl chalcone.
The structure of hydroxyl chalcone is identified by the FT-IR techniques. FT-IR (cm−1): 3500–3200 (O▬H); 3100–2800 (C▬H); 1690 (>C〓O); 1605 (▬CH〓CH▬); 1570 (aromatic, C〓C).
In a 250 mL three-necked flask, triethylamine (3 mol) and hydroxyphenyl-methoxystyryl ketone (1 mol) are dissolved in 100 mL of methyl ethyl ketone (MEK) and cooled between 0 and −5°C. Methacryloyl chloride (1.1 mol) in 50 mL of methyl ethyl ketone is then added drop by drop with mixing. After then, the reaction mixture is mixed for 3 h at 20°C and the precipitated quaternary ammonium salt is filtered off. Later, 100 ppm of hydroquinone is added to this solution and the MEK is removed by the vacuum evaporator. The raw product is dissolved in diethyl ether, washed one after another with a 5% aqueous potassium hydroxide solution and distilled water, dried over anhydrous magnesium sulfate (MgSO4) and the diethyl ether is removed by the evaporator. The obtained material is recrystallized from methyl alcohol to get the shining yellow flakes of sübstitue methacryloyloxyphenyl-methoxystyryl ketone. Yield: 80%. The synthesis reaction scheme is given in Figure 18.
Reaction scheme of methacryloyloxyphenyl-methoxystyryl ketone.
The structure of methacryloyloxyphenyl-methoxystyryl ketone is confirmed by the FT-IR and 1H- and 13C-NMR spectroscopic techniques. FT-IR (cm−1): 3100–2800 (C▬H); 1740 (>C〓O); 1650 (▬C〓O); 1630 (CH2〓C); 1605 (▬CH〓CH▬); 1570 (aromatic, C〓C); 1190 (C▬O▬C). 1H-NMR (CDCl3, TMS): 8.1–6.9 (aromatics ▬H); 6.3–5.78 (CH2〓C, and ▬CH〓CH▬); 3.84 (OCH3); 1.8 (CH3). 13C-NMR (CDCl3, TMS): 178.0 (▬
Substituted methacryloyloxyphenyl-methoxystyryl ketone is polymerized as a 3 molar solution in MEK using 2,2′-azobisisobutyronitrile (AIBN) as initiator at 70°C. The predetermined quantities of sübstitue methacryloyloxyphenyl-methoxystyryl ketone, the initiator (1 wt.% of monomer) and solvent are placed in a polymerization tube and the mixture is flushed with a slow stream of nitrogen for 20 min. Then, the tube is closed and placed in the thermostated oil bath at 70°C. After the specified time (12 h), the contents are added to excess methyl alcohol to precipitate the polymer. The crude polymer is purified by redissolving in 1,4-dioxane and reprecipitated by methyl alcohol, filtered, washed with methyl alcohol and dried under vacuum at 45°C for constant weight. Yield: 60%. The reaction scheme is shown below (Figure 19).
Reaction scheme of poly methacryloyloxyphenyl-methoxystyryl ketone.
The structure of poly methacryloyloxyphenyl-methoxystyryl ketone is confirmed by the FT-IR and 1H-NMR spectroscopic techniques. The information is clearly seen in 1H-NMR spectroscopy on polymer formation. The formation of polymer is clearly evident from the disappearing of the two singlets at 6.3 and 5.78 ppm of the vinyl protons and the wide peaks at 2.7–1.3 ppm due to the conversion to the aliphatic ▬CH2 group. The main description of the polymer is exactly the extinction of some characteristic peaks of the double bond in the FT-IR spectrum, and this real is effectively identified herein. Two signals altered in the FT-IR spectrum of the monomer: the stretching vibration band of the vinyl group C〓C at 1630 cm−1 and the absorption signal at 920 cm−1 assigned to the C▬H bending of geminal〓CH2.
In this paper, reaction pathway for the synthesis of new methacrylates having pendant amide, dioxolane, benzofuran and chalcone groups are described. Molecular structure information such as reaction scheme, Fourier transform infrared (FT-IR) and nuclear magnetic resonance spectroscopy of all the compounds is given. All of the methacrylates are used as photodegradable packaging materials and photoresists for microlithography. The increasing utility of photosensitive polymers in many applications such as microelectronics, printing and UV-curable lacquers, and inks is provided us with an incentive to obtain novel polymers.
The authors declare no conflict of interest.
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