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KR-20260065945-A - Organosilicon compounds and their uses

KR20260065945AKR 20260065945 AKR20260065945 AKR 20260065945AKR-20260065945-A

Abstract

The present invention relates to an organosilicon compound containing a unit of the following formula, a method for manufacturing the same, a curable composition comprising said organosilicon compound, a method for manufacturing said composition, and a molded article manufactured from said composition: R a X b SiY (4-ab)/2 In the above formula, R may be identical or different and represent a monovalent hydrocarbon radical, X may be identical or different and represent a hydroxyl group or a monovalent hydrolytic radical, Y may be identical or different and represent -O- or -O- CH₂- [ C₆H₃ (OH) -CH₂ ] n- C₆H₄ - O- or -O-[ C₆H₃ ( CH₂OH )] m - CH₂ - C₆H₄ -O-, where n is an integer from 0 to 10 and m is an integer from 1 to 10 , a is 0, 1, 2 or 3 and b is 0, 1, 2 or 3, provided that the sum of a + b is ≤ 3, and there are 1 to 100 units of formula (I) per molecule of the organosilicon compound and per molecule of the organosilicon compound At least one radical Y of -O- CH₂- [ C₆H₃ (OH) -CH₂ ] n -C₆H₄ - O- or -O-[C₆H₃ ( CH₂OH ) ] m- CH₂ - C₆H₄ - O- is present.

Inventors

  • 프라세 마르코

Assignees

  • 와커 헤미 아게

Dates

Publication Date
20260511
Application Date
20240507

Claims (13)

  1. Organosilicon compounds containing units of general chemical formula (I): R a X b SiY (4-ab)/2 (I), In the above formula, R can be the same or different, and represents a monovalent hydrocarbon radical, X may be identical or different and represent a hydroxyl group or a monovalent hydrolytic radical, and Y can be identical or different from each other, -O- or -O-CH 2 -[C 6 H 3 (OH)-CH 2 ] n -C 6 H 4 -O- or -O-[C 6 H 3 (CH 2 OH)] m represents -CH 2 -C 6 H 4 -O-, and Here, n is an integer from 0 to 10, and m is an integer from 1 to 10, and a is 0, 1, 2, or 3, and b is 0, 1, 2, or 3, and However, the sum of a + b is < 3, and There are 1 to 100 units of formula (I) per molecule of the organosilicon compound, and At least one radical Y of -O-CH₂-[C₆H₃(OH)-CH₂]n-C₆H₄ -O- or -O-[C₆H₃(CH₂OH ) ] m - CH₂ - C₆H₄ - O- exists per molecule of the organosilicon compound .
  2. In paragraph 1, At least 20% of radical Y is, -O-CH 2 -[C 6 H 3 (OH)-CH 2 ] n -C 6 H 4 -O- or An organosilicon compound representing -O-[C 6 H 3 (CH 2 OH)] m -CH 2 -C 6 H 4 -O-.
  3. In paragraph 1 or 2, An organosilicon compound in which radical R each independently represents a monovalent hydrocarbon radical having 1 to 10 carbon atoms.
  4. In any one of paragraphs 1 through 3, An organosilicon compound in which X each independently represents a hydroxyl group or an organyloxy radical -O R 1 , where R 1 represents an optionally substituted monovalent hydrocarbon radical in which an oxygen atom may be interposed.
  5. In any one of paragraphs 1 through 4, Y independently represents -O- or -O- CH₂- [ C₆H₃ (OH) -CH₂ ] n- C₆H₄ - O-, and n is an organosilicon compound in which n is an integer from 1 to 10.
  6. In any one of paragraphs 1 through 5, An organosilicon compound in which Y independently represents -O-, -OCH2C6H4O- , -OCH2C6H3 ( OH ) CH2C6H4O- or -OCH2 ( C6H3 ( OH) CH2 ) 2C6H4O .
  7. In any one of paragraphs 1 through 6, An organosilicon compound containing 2 to 50 units of formula (I) per molecule of the organosilicon compound.
  8. In any one of paragraphs 1 through 7, Organosilicon compounds that are organosilicon compounds of the following formula (II): [X g R 3-g SiY 1/2 -] p [X i R 2-i SiY 2/2 -] q [X j R 1-j SiY 3/2 -] r [SiY 4/2 -] s (II), In the above formula, R , X, and Y are each as defined above, and g is 0, 1, 2, or 3, and i is 0, 1, or 2, and j is 0 or 1, and p is an integer of 0 or 1 to 10, and q is an integer of 0 or 1 to 90, and r is an integer of 0 or 1 to 10, and s is an integer of 0 or 1 to 10, and However, the sum of ( p + q + r + s ) is a number from 2 to 100, the unit may have any distribution, and at least one radical Y of -O-CH 2 -[C 6 H 3 (OH)-CH 2 ] n -C 6 H 4 -O- or -O-[C 6 H 3 (CH 2 OH)] m -CH 2 -C 6 H 4 -O- is present per molecule of the organosilicon compound .
  9. A method for manufacturing an organosilicon compound according to any one of claims 1 to 8, A method of preparation in which a silane having three and/or four hydrolyzable groups is esterified with an alcohol or a diol.
  10. (A) A curable composition comprising at least one organosilicon compound according to any one of claims 1 to 8.
  11. In Paragraph 10, A thermosetting curable composition.
  12. A method for manufacturing a curable composition according to claim 10 or 11, A manufacturing method comprising the step of mixing all components in any desired order.
  13. A molded article produced by curing a curable composition according to claim 10 or 11.

Description

Organosilicon compounds and their uses The present invention relates to organosilicon compounds and their manufacture and use. Techniques for preparing organosilicon compounds from organosilanes and difunctional or polyfunctional alcohols have long been known. For example, US 2906768 describes the reaction of an organohalosilane with a difunctional aliphatic alcohol. US 4072655 describes the use of liquid glycol-functional silanes and siloxanes in a paste that has storage stability in the absence of atmospheric humidity and hardens to form a solid object in the presence of atmospheric humidity. US 2006107876 includes a method of directly reacting 1 mole of alkyltrihalosilane or alkyltrialkoxysilane with at least 2.0 moles of glycol to produce a glycol-functional siloxane that is liquid at room temperature, and using the siloxane for hydrophobization of gypsum. In contrast, US 2006107876 claims to produce a polyhydroxy-functional siloxane that is solid at room temperature by reacting an alkyltrihalosilane, an alkyltrialkoxysilane, a mixture or hydrolysate thereof with a polyhydroxy compound, and to use the polyhydroxy-functional siloxane for hydrophobization under conditions using 0.3 to 1.3 hydroxyl groups per hydrolyzable group. The present invention provides an organosilicon compound containing a unit of the following formula (I). RaXbSiY(4-ab)/2 (I), In the above formula, R can be identical or different and represents a monovalent hydrocarbon radical, and X may be identical or different and represents a hydroxyl group or a monovalent hydrolytic radical, and Y may be identical or different and represents -O- or -O- CH₂- [ C₆H₃ (OH) -CH₂ ] n -C₆H₄ -O- or -O-[ C₆H₃ ( CH₂OH )] m -CH₂ -C₆H₄ - O- , and Here, n is an integer from 0 to 10, and m is an integer from 1 to 10, and a is 0, 1, 2, or 3, preferably 1, and b is 0, 1, 2, or 3, preferably 0 or 1, and However, the sum of a + b is < 3, and There are 1 to 100 units of formula (I) per molecule of the organosilicon compound, and At least one radical Y of -O- CH₂- [ C₆H₃ (OH) -CH₂ ] n- C₆H₄-O- or -O-[C₆H₃(CH₂OH)]m-CH₂-C₆H₄-O-, particularly -O-CH₂-[C₆H₃ ( OH ) -CH₂ ] n - C₆H₄ - O- exists per molecule of the organosilicon compound . In the context of the present invention, Yof the form -O-CH₂-[C₆H₃(OH)-CH₂]n-C₆H₄-O- or -O-[C₆H₃(CH₂OH)]m-CH₂-C₆H₄-O-canbeunderstood as a difunctional hydrolyzable radical, particularly a unit comprising a methoxy group and a phenoxy group. Thus, Y can be understood as a condensation product of hydroxybenzyl alcohol, particularly 2-hydroxybenzyl alcohol. In a preferred embodiment, Y each independently represents -O- or -O- CH2- [ C6H3 (OH) -CH2 ] n - C6H4 - O- , in particular -O- CH2- [ C6H3 (OH) -CH2 ] n - C6H4 - O-, where n is as defined above. In the organosilicon compound according to the present invention, preferably at least 20%, particularly preferably 30% to 80% of the radical Y represents -O- CH₂- [ C₆H₃ (OH) -CH₂ ] n - C₆H₄ -O- or -O-[ C₆H₃ ( CH₂OH )] m - CH₂ - C₆H₄ - O-, particularly -O- CH₂- [ C₆H₃ (OH) -CH₂ ] n- C₆H₄ - O- . In a preferred embodiment, the organosilicon compound comprises at least one unit of formula (I) in which a=1 and b=0 or a=1 and b=1, particularly a=1 and b=0 per molecule. Preferably, radical R is selected from monovalent hydrocarbon radicals having 1 to 10 carbon atoms, particularly preferably from alkyl radicals, vinyl radicals and phenyl radicals, particularly methyl, vinyl, phenyl, or octyl radicals. Examples of radical R include alkyl radicals such as methyl, ethyl, n-propyl, isopropyl, 1-n-butyl, 2-n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl, and tert-pentyl; hexyl radicals such as n-hexyl; heptyl radicals such as n-heptyl; octyl radicals such as n-octyl and isooctyl radicals such as 2,2,4-trimethylpentyl; nonyl radicals such as n-nonyl; decyl radicals such as n-decyl; dodecyl radicals such as n-dodecyl; octadecyl radicals such as n-octadecyl; cycloalkyl radicals such as cyclopentyl, cyclohexyl, cycloheptyl, and methylcyclohexyl; and alkenyl radicals such as vinyl, 1-propene, and 2-propene. Examples include aryl radicals such as phenyl, naphthyl, anthryl, and phenanthryl; alkalil radicals such as o-, m-, p-tolyl radicals, xylyl radicals, and ethylphenyl radicals; and aralkyl radicals such as benzyl, α-, and β-phenylethyl. Examples of radical X include hydroxyl groups and organyloxy radicals -O R 1 , where R 1 represents a monovalent hydrocarbon radical that may have an oxygen atom interposed therein and is optionally substituted, in particular alkyl radicals (e.g., methyl radical or ethyl radical), alkoxyalkyl radicals (e.g., alkoxyethyl radical) and hydroxyl-containing radicals (e.g., 2-hydroxybenzyl, 4-hydroxybenzyl, 2-hydroxymethylphenyl or 4-hydroxymethylphenyl). In certain embodiments, radical X each independently represents an organyloxy radical -O R 1 , where R 1 represents an optionally substituted monovalent alkyl radical in which an oxygen atom may be interposed. Prefe