TWI280233B - Branched, reactive-type surfactant compound, method for producing the same, and applications thereof - Google Patents

Abstract

The present invention is related to a compound of the formula, wherein L is H, CH3 or an ionic hydrophilic group; X is H or CH3; a, c, d, f and n are independently integers, f is selected from 1 to 6 and n is selected from 1 to 3; Y is an aliphatic or aromatic group with 1 to 30 carbon atoms; S and T are independently, and Z is a group having 1 to 3 C=C double bonds.

Description

1280233 IX. DESCRIPTION OF THE INVENTION: TECHNICAL FIELD OF THE INVENTION The present invention relates to a surfactant, and more particularly to a surfactant having a branched reaction type. [Prior Art] Surfactants can be classified into long-chain alkyl groups, hydrophilic groups, and hydrophilic groups (hydr〇phiUc gr〇u) according to their structure. The three types of wounds can be classified according to different resolutions and charges. The surfactant is soluble in water and can be separated into anionic, cationic, zwitterionic or non-dissociated into ions after being dissolved in water. It is divided into anionic surfactant, cationic surfactant, zwitterionic surfactant and nonionic. Four kinds of surfactants, etc. When the concentration of the surfactant in the aqueous solution changes, the physicochemical properties of the aqueous solution such as cleaning power, density, surface tension, infiltration M, and amount conductivity are added to the surfactant at a certain concentration. Sudden change. The concentration of surfactants in the tens or hundreds of surfactants becomes a theory of miCelle. This concentration is called microcell formation concentration or critical microcell concentration change in the surfactant. The hydrophilic and lipophilic structure can change the characteristics of forming micelles, emulsifying, dispersing, etc. The inside of the microcells in the aqueous solution is mostly composed of alkyl molecules, so The oil or organic liquid in water is soluble in the microcapsules of the surfactant. This phenomenon is called melting (5) ubilizatiGn). The surfactant composed of the hydrophilic group composed of the same hydrophilic group, the oleophilic group The smaller the CMC is, the smaller the CMC is. 1280233 The surfactant molecule of Bali has a hydrophilic molecular chain and a hydrophobic molecular chain, which has the effect of reducing surface tension and forming microcells, which are widely used for emulsification, dispersion, cleaning, wetting, etc. Application, it is an indispensable component in the manufacture of inks, coatings, adhesives, photoresists, etc. ^ ^Special interface surfactants do not have polymerizable functional groups, when made into film or block products, Since the surfactant is not bonded to the polymer, it remains in the free state in the polymer, and the properties such as water resistance, adhesion, and oil resistance of the coating film, the e-film printing surface, and the coated film are changed. Poor, if the surfactant remaining in the free state diffuses to the interface of the film surface or the multilayer structure after long-term use, the long-term durability of the product is deteriorated. The surfactant which reduces the free state can be To improve this problem, the method of reducing the free-state surfactant is to make the surfactant have a polymerizable functional group, and participate in the polymerization reaction and polymer bonding during formation without remaining in a free state, which is called reactive interfacial activity. Agent (also known as polymerizable surfactant). The reactive surfactants in the prior art are mostly direct-bonded structures, and contain only one reactive OC functional group, which has high foaming and poor reactivity. Gemini-type surfactants (such as the surfynol series with 2 branched hydrophilic chains, manufactured by Air Pr〇duct) have lower foaming properties. Reactive surfactants are available in a variety of configurations. It is proposed, but most of them have only a single carbon-carbon double bond (C=C)' and then change different hydrophilic or hydrophobic groups to make different surfactants. In the part of the different hydrophilic groups, a neutral surfactant having an alkoxy group is included, for example, Japanese Patent Laid-Open No. 2003-268021, and Japanese Patent Laid-Open Publication No. Hei 2 No. Hei 2-1280233 97212 are the same; The patent 丨 020064 uses an ionic hydrophilic group. Further, JP-A-2002-88104, JP8041 1 13, JP8041 1 12 uses both an alkoxy group and an ionic group as a hydrophilic group. As for the hydrophobic portion, a sulfo succinate having a hydrocarbon group is used in Japanese Patent Publication No. Sho 49-46291; Japanese Laid-Open Patent Publication No. SHO 62-1 00502, Japanese Laid-Open Patent Publication No. SHO 63-23725, and Japanese Patent Laid-Open No. 4-50202 An alkoxy ester in which a hydrocarbon having a fluorenylpropyl group or a propyl fluorenyl group is substituted with a phenol is used, and a hydrocarbyl group or a hydrazine is used in the Japanese Patent Laid-Open Publication No. SHO 62-104802. An alkoxy ester of a glycerol derivative; a phenol derivative crosslinked with formaldehyde is used in Japanese Laid-Open Patent Publication No. 62-1 1534; Japanese Patent Laid-Open Publication No. SHO 63-31 90354 In the case of No. 4-50204, etc., an alkyl group derived from an α-olefin oxide or the like is used as a hydrophobic group. A conventional technique for non-reactive surfactants has found that a double-branched Gemini-type surfactant (such as the Surfynol series produced by Air Product) has low foaming properties and can be reduced. Various coating defects caused by bubbles, such as volcanic holes, pin holes, etc. Recently, there has been a structure in which a branched multi-reactive group (C=C) has been developed in the reactive surfactant. For example, in US2002061828, a structure of 2 to 3 C=C is used at the hydrophobic end, but only one burnt oxygen is long. chain. The US6841655 and TW538053 patents have a hydrophobic side chain containing OC attached to the aerobic repeating unit on the alkoxy main chain, and the hydrophilic and hydrophobic structures of the structure alternate. In the above, the existing surfactant mainly utilizes a single burnt oxygen main 1280233', which has high foaming property and poor reactivity, and needs to be further improved. The chain is attached with a 〇C-containing side chain design. The use of free radicals after use, etc. [Explanation] The surfactant can be classified into a non-reactive type and a reactive type (polymerizable type interactive agent). The surfactant of the present invention is a polymerizable surfactant, which can polymerize a surfactant and other components at the time of film formation, thereby eliminating the problem of adhesion due to a free-residual surfactant and a decrease in water resistance. The main technical feature of the present invention is that a polybranched hydrophobic chain having a c=c functional group is attached to the end of each alkoxy chain (not to the branch of the alkoxylated chain repeating unit), and the OC is located in the hydrophobic chain. The end portion enables the plurality of multi-branched terminal OC functional groups to enhance reactivity while retaining the stereodispersion stability effect of a plurality of alkoxylated chains, especially for emulsion polymerization, which may have both an emulsifier, a reactive monomer and a crosslinking agent. Features. The invention features a comb-hke structure with 3~8 multi-branched alkoxy chains, in order to have low foaming property, multiple alkoxy chains and good stereodispersion during emulsification and dispersion. The effect of the invention is related to a compound having the following chemical formula (1) p - 0~(-CH2-CHx--γ.ί L -CH2-〇-(~CH2-CHx- 〇)^S—YfT-2CH 广〇^CH广CHx——Y_^.T__.2 ^ •z

Wherein L is H, CH3 or an ionic hydrophilic group; 1280233 X is 11, called; 3, 〇, (1, € and 11 are positive integers, wherein £ is selected from 1 to 6, and 11 is selected from 1 to 3; Y is a Ci-3 0 aliphatic or aromatic molecular chain; P Η S and T are 0 -c-〇~ _C--N- -o- 0 Η

OH · 〇 - C--N- _ 〇 - CH2-CH - or - ch2 -; and Z is a long chain molecule containing 1 to 3 > C = C < Preferably, wherein z is the following long chain molecule: 0 CH=C一^-C--R2 R3 1=0 〜1 m=0~12 R2? R3=H5 CH, or -0-CH ten CHfO A C-jpCzrz^CH 0 R3 R2 •Ο—CH2—ch2

-CH

丨2 and one C-^pC

:CH 0 R3 R2 , wherein R 2 and R 3 are each independently H or CH 1 rabbit n^ is selected from an integer from 0 to 12, and the remaining substituents are defined as & Preferably, the above compound is used as a surfactant. The invention further relates to an emulsifier comprising the compound disclosed above. The invention further relates to a photopolymerizable monomer comprising the compound disclosed above. 10!28〇233 A resin modifier of the present invention comprising the compound disclosed above. This volume is also related to a method of making the above disclosed compounds, which comprises

• V dissolves glycerol-grafted polyoxyethane in dimethyl decylamine [DMF], in the presence of tin chloride, at about 7 Torr in 1 〇〇t: for the first heating reaction, and The reaction product is first heated with glycidyl methacrylate and dimethylformamide for a second heating reaction at about 60 to about 7 Torr. [Embodiment] The term "surfactant" as used in the present invention means a lipophilic group containing a long-chain alkyl group (e.g., a fatty acid) in a molecule and a hydrophilicity sufficient to disperse or dissolve an oily part in water. Base of chemicals. The term "ionic hydrophilic group" as used herein shall mean a hydrophilic group having a dissociable ion, such as a solubilized sodium salt (-COONa). • The term "reactive" as used in the present invention means that the compound has a reactive OC functional group. - The present invention relates to a surfactant and a method of producing the same. The surfactant has the structure of the formula (1) and has a hydrophilic chain of 3 to 8 branched comb-like structures, which can reduce foaming property. Further, a branched structure of a hydrophobic chain is attached to the end of the hydrophilic chain, and a plurality of branched reactive c=c functional groups are introduced to improve the reactivity. Formula 1)

11 1280233 CH^O-^CH^CHx-O-^s—Υ-(-τ—Z)n —CH2—〇-f CH2—CHx—〇}^s—Y—pr—z CH FactoryΟ—( ·〇Η2-CHx-O^-s—Y—__z The surfactant of the present invention has a hydrophilic chain and a hydrophobic chain at both ends of the molecular structure, and the structure is closer to the block copolymer (bl〇ck c〇p〇) Lymer)

In order to have a better anchoring group effect and a more stretchable stabilizing group, the emulsification and dispersion stability is better than that of the hydrophobic main chain to which the hydrophobic side chain is attached. The surfactant of the present invention can be synthesized by a simple reaction reaction through the reaction design (in the embodiment, a two-step reaction synthesis), without cumbersome synthesis steps, which helps to reduce costs and increase the synthesis yield, thereby increasing the output of the industry. Feasibility, with great industrial use value. There are many synthetic methods, such as addition polymerization, condensation polymerization, ionic polymerization, and radical polymerization. Among them, the radical polymerization method includes bulk polymerization, solution polymerization, and emulsifying polymerization (emulsi〇np〇). LymeHzati〇n), suspension polymerization (suspension p〇lymerizati〇n) and dispersion polymerization. The emulsion polymerization method has the following properties and advantages. (1) It is easy to control its initiation, growth, chain transfer and termination. reaction. (2) It is suitable for continuous operation, high polymerization rate, and easy to obtain high t-combination products. (3) Under high conversion rate, the reaction system can still maintain low viscosity, which is beneficial to industrial production processes such as mixing, heat transfer and transportation. Most of the products can be

12 1280233

Paint and other uses. Do further processing. [Change of solubility of the solvent or polymerization temperature of the sputum-passing agent] can be applied to paints, retouching agents, floor light-reducing agents or oils by changing the reaction method and reaction composition. (5) Lithification polymerization using water as a solvent, low cost And production safety, can reduce environmental pollution. Into the research of emulsion polymerization, and these advantages have attracted a large number of manpower applications in a wide range of industrial processes. When the surfactant of the present invention is used as an emulsifier for emulsion polymerization, it can be used arbitrarily in the range of the usual use amount of the emulsifier for conventional ritual polymerization, but it is preferably about the raw material monomer. % by mass, more preferably 〇·丄〇丄〇丄〇%. Further, the emulsifier for emulsion polymerization of the present invention may be used in combination with other reactive or non-reactive emulsifiers. The monomer to be emulsion-polymerized is not particularly limited and may be selected from the group consisting of C1-C18 alkyl methacrylate, ci-C18 alkyl acrylate, 2-ethylhexyl (meth) acrylate, and (meth) acrylate. Fat, lauryl (meth) acrylate, allyl (meth) acrylate, stearyl phthalate, propionic acid, itaconic acid, methacrylic acid, butadiene, vinyl acetate, Koch Acid vinyl ester, styrene, vinyl aromatic monomer, hydroxyethyl (meth) acrylate, hydroxypropyl (meth) acrylate, propylene, divinyl benzene, divinyl toluene, ethylene glycol Methyl) acrylate, divinyl fluorene benzene, divinyl ethyl benzene, divinyl ketone, divinyl sulfide, diallyl maleate, 13 1280233 fumarate Propyl ester, diallyl succinate, diallyl carbonate, diallyl propionate, diallyl oxalate, diallyl adipate, di-propyl propyl sebacate, sebacic acid Vinyl ester, diallyl tartrate, distillate, dicarbamelate, aconitate Allyl vinegar, triallyl citrate, triallyl phosphate, N,N-methylene dimethyl decylamine, N,N-methylenedimercapto acrylamide, trivinylbenzene, And diol, glycerin, isovalerol, polyvinyl ether of resorcinol, monosulfide and disulfide derivatives of diol, and combinations thereof. The surfactant of the present invention has photo-reactive reactivity, and can also be used as a monomer for photopolymerization, either alone or in photopolymerization with other photopolymerizable monomers, as a resin modifier. The hydrophilicity can be adjusted by selecting the degree of polymerization of the alkoxy group and the type of the functional group to be formed, depending on the purpose of the modification and the compatibility between the monomers. Therefore, the photopolymerization single system of the present invention can adjust its compatibility with other monomers and adjust the modification characteristics of the polymer. The use i of the photopolymerization monomer of the present invention can be variously changed by the properties required for the purpose of the modification of the monomer. The documents cited herein are incorporated herein by reference. The following examples are intended to illustrate the invention. These examples are not intended to limit the scope of the invention in any way, and the effect - filial piety is used to refer to the materials and methods of the invention. Example 1·· G26BG-surfactant (1 scale GE026 ([glycerol grafted polyoxyethane, 26 alkoxyethyl groups 14 1280233 complex units]) (2. 045 9g) and dissolved in DMF [two In the methylformamide L (9 g), BTCA (1,2,4-Benzenetricarboxylic anhydride) (0.954 g) and the catalyst SnCl2 (0.2 g) were prepared. The round bottom flask was fixed in an oil bath. In the middle, the temperature of the oil bath is set to 90 ° C. First add GE026 dissolved in DMF and then add BTCA and SnCl2, and stir with magnet for 8 hours. The reaction is completed. Glycidyl methacrylate GMA (1.4112g) and DMF (4.5g), and set the reaction temperature to 70 ° C. Fix the above product to the round bottom flask in the oil bath, set the temperature of the oil bath to 70 ° C. Then GMA and DMF was added to the reaction and stirred with a magnet. After 8 hours, the reaction was completed to obtain the product. The chemical structure was as follows: x+y+z= 26

——^EO^〇——COR -f-EO-^-O——COR ——{Ε〇)γΟ——COR

Example 2: G26SG-surfactant (2) Scale GE026 [glycerol grafted polyoxyethylene, a total of 26 alkoxyethyl repeat units] (2.4137g) and dissolved in DMF (9g), and prepared grass Anhydride (Succinic Anhydride (SA), 0· 5863g) and catalyst

SnCl2 (0.2 g). The round bottom flask was fixed in an oil bath, and the temperature of the oil bath was set to 90 °C. First, add GE026 dissolved in DMF and then add S. A and SnCl2, 15 1280233 and stir with a magnet for 8 hours. Re-glycol methacrylate (GMA) (0.8328 g) and DMF (2.5 g) were set at a reaction temperature of 7 Torr. . . The above product was first placed in a round bottom flask and fixed in an oil bath. The temperature of the oil bath steel was set to 赃. Will

G Μ A and D M F were added to the reverse shore shot with τι 4 spot _ι I. The reaction was stirred by a magnet and the reaction was completed after 8 hours. The chemical structure is shown below. x+y+z=26

fEO 拎〇—8—CH2—CH2-C—-〇R 〇¥0一c—CH2—CH2-§—〇R iEOk°—c—CH2—CH2—§~〇R 〇R= -CH2-CH —CH2-〇c-

OH C=CH2 ch3 Example 3: G7SG~activator (3) Scale GE07 [glycerol grafted polyoxyethane, a total of 7 alkoxyethyl repeat units] (1.738 g) and dissolved in DMF (9 g) In addition, succinic anhydride (Succinic Anhydride, 1.2862 g) and catalyst SnCl2 (0.2 g) were additionally prepared. The round bottom flask was fixed in an oil bath, and the temperature of the oil bath was set to 9 (rc. The first addition of GE026 dissolved in DMF was added to s. A and SnCl2, and the reaction was completed after stirring with a magnet for 8 hours. The reaction temperature of oxypropyl ester (1.82272g) and DMF (5.5g) was 70 C. The above product was placed in a round bottom flask and fixed in an oil bath. The temperature of the oil bath steel was set to 7 (TC. DMF was added to the reaction and stirred with magnet 16 1280233. After 8 hours, the reaction was completed, and the chemical structure was as follows: -(ΕΟ^χΟ--(E〇)y 0-

〇 -C 〇 C

iEC%〇—C

〇 CH2—CH2-C ——OR 〇 CH2—CH2—C ——OR 〇 CH2—CH2-C ——OR x+y+z=7 〇 c=ch2 ch3

CH2—CH—CH2—O ——C

I

OH Example 4: Foaming test The surfactant (1)-(3) was diluted with water to form a 1% solution with a commercial comparative product (MS-60, RMA-906), and 5 mL of the diluted emulsion was placed in a 20 mL glass. The inside of the bottle was shaken vigorously for about 10 seconds, and the foaming height immediately after the shaking and after 5 minutes was measured. The polymer emulsion after polymerization was diluted to 2 times with water, and 5 mL of the diluted emulsion was placed in a 20 mL glass bottle, and vigorously shaken for about 10 seconds, and the foaming height immediately after the shaking and after 5 minutes was measured. The results are shown in the following table. The surfactant of the present invention has the characteristics of low foaming and rapid defoaming. Table 1: Foaming test interface surfactant (1) Surfactant (2) Surfactant (3) MS-60 RMA-906 After shaking, the bubble height is 1mm 3mm 3mm 9mm 20mm 20 seconds bubble height 8 seconds 0mm (defoaming 16 seconds 0mm (anti-foaming) 10 seconds 0mm (anti-foaming) 9mm 20mm 1 minute - - 9mm 20mm 5 minutes - - - 9mm 20mm 2 hours cans - 5mm 6mm The chemical structure of the commercial comparison product is shown below. MS—60 17 1280233 1 Γ一·〇-{—CH2CH2〇-)^C.Q = CH2

o+ch2ch2o)^so3NH4

RMA-906

H H2C=C——co —(ch2ch2o)

OR 〇

MPG-130MA ch3 h2c=c一co—(ch2ch2o)^—ch3 o

Example 5: Emulsification polymerization test The surfactants (1) to (3) of the present invention and comparative product 1 (non-reactive surfactant, sodium dodecyl sulfate) and comparative product 2 (reactive surfactant) were used. Sinopol MPG-1; 30MA) Emulsified polymerization of an emulsifier. Observed as an emulsifier for emulsion polymerization, emulsion polymerization was carried out using a mixture of acrylic acid, propylene, butyl styrene and styrene as a monomer. The particle size and foaming property of the obtained polymer emulsion were measured. Interface of the Invention 18 1280233 • The active agent has a good emulsifying effect. 5.1 Particle size measurement The particle size of the above polymer emulsion after polymerization was measured at 25 ° C using a light scattering particle size analyzer (〇tsuka, photal LAP-3000/3100). 5.2 Emulsification polymerization test (!) First fix the round bottom flask in the oil bath and install the mechanical stirring device (set the oil bath temperature to 70 ° C, stirring rate 200 r.p.m). Prepare the prepared deionized water (30 g), 0. 09 g of surfactant (2), potassium persulfate (potassium persulfate, 〇·〇 45 g) in sequence, and stir for 3 minutes.疋 ✓ After the solution, add butyl acrylate (3 75 g), acrylic acid (0. 09 g), glycidyl methacrylate (0.09 g) and start timing. . Samples were taken several times at regular intervals, and the particle size was measured. The sample was dripped with 3% chlorine as an inhibitor. After 4 hours of reaction, the average particle size was 492 8 nm.丨5.3 Emulsification polymerization test of surfactant (1) (2) First fix the round bottom flask in the oil bath and install the mechanical stirring device (set the oil bath temperature 7 (TC, stirring rate 200 rpm). Prepare deionized water (30g), 0.09g surfactant (1), potassium persulfate (〇.045g) in order, let it mix for 3 minutes, then add acrylic after dissolution. Butyl ester (buty| acryiate, IK gram acrylic acid (acryHc acid, 〇. 〇 9 g), methacrylic acid propylene acrylate (0.09 g) and start timing. Sampled several times at regular intervals And determine the particle size, sample 19! 28 〇 233 drops into the 3% of the chlorine as an inhibitor. After 4 hours of reaction, the average particle size is 272. 6 nm. 5.4 emulsification of surfactant (1) Polymerization test (3) First fix the round bottom flask in the oil bath and install the mechanical mixing device (set the oil bath temperature to 70 ° C, stirring rate 200 rpm) and prepare the deionized water (30 g). ), 〇·〇 9 grams of surfactant (potassium persulfate, potassium persuifate, · 045 g), placed in sequence, stirred for 3 minutes, determined to dissolve, then add butyl acryiate (^75 g), 'styrene (styrene, 1.875 g), acrylic acid (acrylic acid, 〇〇9 g Glycidyl methacrylate (0.09 g) was started and timed. Samples were taken several times at regular intervals, and the particle size was measured. The sample was dropped into a concentration of 3 % hydrogen as an inhibitor. The average particle size is 253.7 nm. 5 · 5 Surfactant (1) emulsion polymerization test (4) First fix the round bottom flask in the oil bath steel and install the mechanical stirring device. (Set the oil bath pin temperature 7 0 °C, 攒: mixing rate 2 0 0 r · p · m), and prepared deionized water (20 g), 0. 06 g of surfactant (1), persulfate (potassium persulfate, 0.03)克) Put in order, stir for 30 minutes, then confirm the dissolution and then add butyl acrylate (I.5g), ethyl acrylate (1.5g), acrylic acid (acryiic acid, 〇·〇 3 g), mercaptopropionate propylene _ (glycidyl meth Acrylate, 0.06 g) and start timing. Samples were taken several times at regular intervals and the particle size was determined. Sample 12 2080233 was instilled with 3% hydrogen as an inhibitor. After 8 hours of reaction, the average particle size was 2 5. 2 nm. 5.6 Emulsion polymerization test of surfactant (3) (5) First fix the round bottom flask in the oil bath steel and install the mechanical stirring device (set the oil bath temperature 70 ° C, stirring rate 200 r.p.m). Prepare deionized water (30 g), 0.09 g of surfactant (3), and potassium persulfate (0.045 g) in sequence, stir for 3 minutes, and then add acrylic acid after dissolution. Butyl acrylate (1.875 g), styrene (styrene, 1.875 g), acrylic acid (acryiic acid, 〇·〇9 g), methyl propyl methacrylate (glycidyl methacrylate, 0·〇9 g) ) and open the timing. Samples were taken several times at regular intervals, and the particle size was measured. The sample was dropped with 3% hydrogen as an inhibitor. After 4 hours of reaction, the average particle size is 245. 9 nm ° 5 · 7 non-reactive surfactant emulsion polymerization test First fix the round bottom flask in the oil bath and install the mechanical spoiler (set the oil bath steel temperature 70 'stirring rate 200 r· ρ· m). Prepare the prepared deionized water (20 g), 〇·〇 6 g of sodium dodecyl sulfate, potassium persulfate (0.03 g) in sequence, stir for 3 minutes, then confirm the dissolution and then add C. Butyl acrylate (3.12 g) was started and timed. Samples were taken several times at regular intervals, and the particle size was measured. The sample was dropped with 3 % hydrogen as an inhibitor. After the reaction for 8 hours, the average particle diameter was 4 〇. 3 nm. 21 128023.3 5 · 8 Reaction-type surfactant emulsion polymerization test First fix the round bottom flask in the oil bath steel and install the mechanical spoiler (set the oil bath temperature 70, stirring rate 200 r.p.m). And prepared deionized water (20 g), 0.06 g of reactive surfactant sin〇p〇i MPG-130MA (Sino-Japan Chemical co), potassium persulfate (potassium persulfate, 0.03 g) Put in order, stir for 3 minutes, then confirm the dissolution, then add butyl acrylate (312 grams) and start timing. After 8 hours of reaction, the emulsion could not be polymerized. Example 6: Photopolymerization first interface activity The agent (1) and the photoinitiator (1-hydorxy-2-methyl-l-propane-di-neane) are 于1 in the sample bottle, and the magnet is used as a knife for stirring. The square film applicator is coated on the glass. 4〇μηη thickness of the film, the coated glass is placed in a vacuum oven, vacuum at room temperature for a minute and then heated to 40 ° C for 20 minutes, and then heated to 5 ° ° C for 20 minutes, _ solvent Completely volatilize. Place the film with the solvent removed in the uv reaction chamber (UVP CL-1000 ultravi〇let Cr〇ssHnker) and illuminate for 5 minutes. - Remove the film with a spatula using DSC (TA Instrument DSC2920) The rate of 5 C per knife clock is increased by 3〇丄5〇, measured as 85. Surfactant (1) has photopolymerization reactivity. According to the different modifications and changes made by Ben Maoming, for those skilled in the art:,,; Scope and spirit of the invention.Although the invention is described in terms of specific preferred specific facts, it must be understood that the invention should not be

22 1280233 ^ Unduly restricted to these specific specific facts. In fact, the various modifications that are obvious to those skilled in the art are also covered by the following claims. [Simple diagram description] None [Main component symbol description] None

twenty three

Claims (1)

1280233 Patent Application Range: 1 · A compound having the following chemical formula CH2 - 0 - (-CH2-CHx- - Y - (-T - Ζ) η LC-CH2 〇 ~ (~CH2 ~ OHx - 〇) - cjf S——Y- -Z n CH2—0—^~CH2-CHx--Y—(-TZ)n where L is H, CH3 or an ionic hydrophilic group; X is Η, CH3; &, 〇, (1, [and 11 is a positive integer, where £ is selected from 1 to 6, and 11 is selected from 1 to 3; Y is a Ch3Q aliphatic or aromatic molecular chain; S and T are 〇-c-〇 - 〇ΗII I -c——Ν- ·〇_ Ο Η OH -0-C-N--〇CH2 - 0H or -CH2—; and Z is 1 to 3 >0 = 0< Chain molecules. 2 · The compound of claim 1 of the scope of the patent, wherein Z is 〇 丫 丫 eleven. Leaf, 13⁄4 R3 1 = 〇 ~ 1 m = 0 to 12 R2, R3 = H, CH3 - 0 - CH Ten is called ~〇一 or C^jC=CH 〇R3 R2 〇H2 c Hd c 2 c ο CMy ο cz——R3 CHIR2 3 24 1280233 where 1 and R3 are each independently CH or CH3, i is 〇 or 1, m For the integer from 0 _ to 12, the /, substituent definition is as shown in item 1 of the scope of application. 3 · If the scope of patent application a compound of 1 or 2 which is used as a surfactant. 4 · An emulsifier comprising a compound as claimed in claim 1 or 2. 5. A photopolymerization monomer comprising a patent for a towel A compound of the first or second aspect of the invention. 6 - a resin modifier comprising a compound according to the scope of claim 2 or 2 of the patent application. 7 - a method for producing a compound as claimed in the scope of the patent application, Including dissolving glycerol-grafted polyoxyethane in the T-T-A-A' in the presence of vaporized tin at a temperature of about 70 to about t, and performing a first-time teaching reaction, and The first carbamide, the sub-heated reaction product is reacted with glycidyl methacrylate and a temperature of about 601 about 7 Torr for a second heating reaction.曱 25