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CN-122010820-A - Hindered amine light stabilizer, preparation method and application thereof

CN122010820ACN 122010820 ACN122010820 ACN 122010820ACN-122010820-A

Abstract

The invention relates to a hindered amine light stabilizer, a preparation method and application thereof. The hindered amine light stabilizer mainly comprises one or more compounds shown in a formula I and/or compounds shown in a formula II. The ultraviolet-curing adhesive is added into a photovoltaic adhesive film, so that the light transmittance retention rate of the photovoltaic adhesive film aged in ultraviolet and high-temperature high-humidity environments can be remarkably improved, the yellowing phenomenon can be effectively inhibited, and the ultraviolet-curing adhesive is suitable for various matrix material systems such as EVA, POE, PVB. The photovoltaic adhesive film can be used for packaging a photovoltaic module and has excellent weather resistance and optical stability.

Inventors

  • TIAN JUN
  • LI GUANGHUI
  • WANG YANGYANG
  • HUANG ZHIQIANG
  • LI PENGCHENG
  • LUO HAI

Assignees

  • 利安隆（中卫）新材料有限公司
  • 利安隆凯亚(河北)新材料有限公司
  • 天津利安隆新材料股份有限公司

Dates

Publication Date
20260512
Application Date
20260410

Claims (18)

  1. 1. A hindered amine light stabilizer, characterized in that the hindered amine light stabilizer mainly comprises one or more compounds shown in a formula I and/or a formula II, Wherein, the R 1 and R 2 are the same or different and are each independently selected from H, C 1-10 alkyl and C 1-10 alkoxy, wherein said alkyl and alkoxy are optionally substituted with one or more halogen atoms; r 3 is selected from H, C 1-10 alkyl, C 3-10 cycloalkyl and 3-10 membered heterocycloalkyl, and n is an integer from 1 to 7.
  2. 2. The hindered amine light stabilizer of claim 1 wherein R 1 and R 2 are the same and are selected from the group consisting of H, C 1-4 alkyl and C 1-8 alkoxy, R 3 is selected from the group consisting of H and C 1-4 alkyl, and n is 2, 3, or 4.
  3. 3. The hindered amine light stabilizer of claim 1, wherein R 1 and R 2 are the same and are selected from the group consisting of H, methyl and-OC 8 H 17 ;R 3 are selected from the group consisting of H and methyl, and n is 2,3 or 4.
  4. 4. A hindered amine light stabilizer according to any one of claims 1 to 3, consisting essentially of two or more compounds of formula I and/or compounds of formula II.
  5. 5. The hindered amine light stabilizer of claim 4 consisting essentially of two or three compounds selected from the group consisting of formula I-a2, formula I-a3, formula I-a4, formula I-b2, formula I-b3, formula I-b4, formula II-b2, formula II-b3, and formula II-b 4: 。
  6. 6. The hindered amine light stabilizer of claim 5, wherein the hindered amine light stabilizer consists essentially of compounds of formulas I-a2 and I-a3, or consists essentially of compounds of formulas I-a2, I-a3 and I-a4, or consists essentially of compounds of formulas I-b2, I-b3 and I-b 4.
  7. 7. The hindered amine light stabilizer of claim 6, wherein the hindered amine light stabilizer consists essentially of compounds of formulas I-a2 and I-a3, and wherein the ratio of compounds of formulas I-a3 is less than 45%, or The hindered amine light stabilizer mainly comprises compounds shown in a formula I-a2, a formula I-a3 and a formula I-a4, wherein the proportion of the compounds shown in the formula I-a2, the formula I-a3 and the formula I-a4 is 0% -35%, 5% -70% and 5% -95% respectively.
  8. 8. The hindered amine light stabilizer of claim 6, consisting essentially of compounds of formulas I-b2, I-b3 and I-b4, and further comprising compounds of formulas II-b2, II-b3 and formula-b 4.
  9. 9. Use of the hindered amine light stabilizer of any one of claims 1-8 in a photovoltaic film.
  10. 10. A photovoltaic film comprising a resin matrix material and the hindered amine light stabilizer of any one of claims 1-8.
  11. 11. The photovoltaic film of claim 10, wherein the photovoltaic film comprises 0.1% -1% of the hindered amine light stabilizer by total weight of the photovoltaic film; the resin matrix material is selected from one or more of ethylene-vinyl acetate copolymer, polyolefin elastomer, polyvinyl butyral, thermoplastic polyolefin, copolymer of ethylene and acrylic acid monomer, wherein the acrylic acid monomer comprises at least one of acrylic acid, acrylic acid ester, methacrylic acid and methacrylic acid ester.
  12. 12. The photovoltaic film according to claim 11, characterized in that it further comprises antioxidants and/or uv absorbers; The antioxidant is at least one selected from hindered phenol antioxidants, thioester antioxidants and phosphite antioxidants; the ultraviolet absorber is at least one selected from benzotriazole ultraviolet absorbers, triazine ultraviolet absorbers and benzophenone ultraviolet absorbers.
  13. 13. An anti-aging composition comprising, in parts by weight, (i) 0.1 to 0.5 part of the hindered amine light stabilizer of any one of claims 1 to 8 and (ii) 0.01 to 2 parts of an antioxidant and/or 0.1 to 0.5 part of an ultraviolet absorber; The antioxidant is at least one selected from hindered phenol antioxidants, thioester antioxidants and phosphite antioxidants; the ultraviolet absorber is at least one selected from benzotriazole ultraviolet absorbers, triazine ultraviolet absorbers and benzophenone ultraviolet absorbers.
  14. 14. The composition according to claim 13, wherein the hindered phenol antioxidant is at least one selected from the group consisting of (iso) octyl 3- (3, 5-di-t-butyl-4-hydroxyphenyl) propionate, C7-C9 alcohol mixed ester 3- (3, 5-di-t-butyl-4-hydroxyphenyl) propionate, C12-C14 alcohol mixed ester 3, 5-di-t-butyl-4-hydroxyphenyl propionate, C13-C15 alcohol mixed ester 3, 5-di-t-butyl-4-hydroxyphenyl propionate, C14-C16 alcohol mixed ester 3, 5-di-t-butyl-4-hydroxyphenyl) propionate, stearyl 3- (3, 5-di-t-butyl-4-hydroxyphenyl) propionate, triethylene glycol bis [3- (3-t-butyl-5-methyl-4-hydroxyphenyl) propionate ] and pentaerythritol tetrakis [3- (3, 5-di-t-butyl-4-hydroxyphenyl) propionate ]; the phosphite antioxidant is tris (2, 4-di-tert-butylphenyl) phosphite; the thio ester antioxidant is selected from at least one of 4, 6-di (octylthiomethyl) o-cresol and 2, 4-di (dodecylthiomethyl) -6-methylphenol; The ultraviolet absorber is at least one selected from the group consisting of 2-hydroxy-4-n-octoxybenzophenone, 2- (2 ' -hydroxy-3 ' -tert-butyl-5 ' -methylphenyl) -5-chlorobenzotriazole, 2- (2 ' -hydroxy-3 ',5' -di-tert-pentylphenyl) benzotriazol, 2- (2-hydroxy-5-tert-octyl) phenylbenzotriazol, 2- (2 ' -hydroxy-3 ',5' -dicumylphenyl) benzotriazol and 2- [4, 6-bis (2, 4-xylyl) -1,3, 5-triazin-2-yl ] -5-octoxyphenol.
  15. 15. A composition comprising a photovoltaic film resin matrix material and the anti-aging composition of claim 13 or 14, wherein the photovoltaic film resin matrix material is selected from one or more of ethylene-vinyl acetate copolymer, polyolefin elastomer, polyvinyl butyral, thermoplastic polyolefin, copolymer of ethylene and acrylic acid monomer, wherein the acrylic acid monomer comprises at least one of acrylic acid, acrylic acid ester, methacrylic acid, and methacrylic acid ester.
  16. 16. A photovoltaic module comprising the hindered amine light stabilizer of any one of claims 1-8, or the photovoltaic film of any one of claims 10-12, or the anti-aging composition of claim 13 or 14, or the composition of claim 15.
  17. 17. A process for producing a hindered amine light stabilizer, which comprises reacting a compound represented by the formula a1 and/or a compound represented by the formula a2 with one or more compounds represented by the formula b under conditions sufficient for the reaction to obtain a hindered amine light stabilizer, Wherein R 1 is selected from H, C 1-10 alkyl and C 1-10 alkoxy, wherein said alkyl and alkoxy are optionally substituted with one or more halogen atoms; r 3 is selected from H, C 1-10 alkyl, C 3-10 cycloalkyl and 3-10 membered heterocycloalkyl, and n is an integer from 1 to 7.
  18. 18. The method of claim 17, wherein the one or more compounds of formula b are a mixed acid or mixed ester of succinic acid or an ester thereof and glutaric acid or an ester thereof, or a mixed acid or mixed ester of succinic acid or an ester thereof, glutaric acid or an ester thereof, adipic acid or an ester thereof.

Description

Hindered amine light stabilizer, preparation method and application thereof Technical Field The invention belongs to the technical field of light stabilizers, relates to a hindered amine light stabilizer, a preparation method and application thereof, and in particular relates to a hindered amine light stabilizer mainly composed of one or more compounds shown in a formula I and/or compounds shown in a formula II, a preparation method and application thereof. Background Polymer materials have penetrated into aspects of modern life by virtue of their excellent properties of light weight, strong plasticity, corrosion resistance, good electrical insulation, relatively low cost and the like. From daily plastic packaging, synthetic fiber clothes, automobile tires and electronic product shells to medical appliances, aerospace parts, building waterproof materials, new energy battery diaphragms and photovoltaic battery films in the high-tech field, the application range of the polymer is extremely wide and indispensable. However, these materials are inevitably exposed to various environmental factors (e.g., heat, oxygen, ozone, ultraviolet radiation, etc.) during long-term use, resulting in aging of the polymer, manifested as cracking, discoloration, loss of gloss, reduced strength, unstable dimensions, etc. of the material. The irreversible deterioration of the performance not only shortens the service life of the polymer product, affects the reliability and the safety of the polymer product, but also can generate more wastes due to frequent replacement, thereby causing burden to the environment. Hindered Amine Light Stabilizers (HALS) stand out as an efficient, innovative light stabilizing system. Specific commercial hindered amine light stabilizer products are: bis (2, 6-tetramethyl-1-piperidinyl) sebacate (light stabilizer 770), bis (1, 2,6, mixtures of pentamethyl-4-piperidinyl) sebacate and mono (1, 2,6, -pentamethyl-4-piperidinyl) sebacate (light stabilizer 292), and the like, the bis (2, 6-tetramethyl-1-piperidinyl) sebacate is a hindered amine light stabilizer which is most widely applied, and particularly in the photovoltaic adhesive film industry, the photovoltaic adhesive film mainly comprises an EVA adhesive film, a POE adhesive film, an EPE adhesive film and a PVB adhesive film. However, currently, the hindered amine light stabilizer mainly adopted by light Fu Jiaomo (including EVA (ethylene vinyl acetate) adhesive film, POE (polyolefin elastomer) adhesive film, EPE (ethylene propylene rubber) adhesive film and PVB (polyvinyl acetate) adhesive film) is bis (2, 6-tetramethyl-1-piperidinyl) sebacate, and the adhesive film using the light stabilizer has the common problems of increased yellow value, reduced light transmittance, reduced adhesive force and the like under the aging condition, so that the whole material is difficult to effectively protect in long-time outdoor use. Meanwhile, the traditional hindered amine light stabilizer mostly adopts single sebacic acid as a raw material, the functional group occupation ratio is low, the light stability performance is improved in a limited space, the raw material cost is high, and the cost reduction and the synergy of the photovoltaic adhesive film industry are not facilitated. Disclosure of Invention In order to solve the problems, the invention provides a hindered amine light stabilizer and application thereof, which can improve the light transmittance reduction of a photovoltaic adhesive film after ultraviolet aging and high-temperature high-humidity aging, and can reduce the yellowing index after ultraviolet aging and high-temperature high-humidity heat aging. Further, the invention provides a method for preparing the light stabilizer, which shortens the curing time of the hindered amine light stabilizer product by regulating and controlling the proportion of the mixed acid components, solves the problems of spray granulation and discharge in the production process, and realizes industrial production. In a first aspect the present invention provides a hindered amine light stabilizer consisting essentially of one or more compounds of formula I and/or formula II, Wherein, the R 1 and R 2 are the same or different and are each independently selected from H, C 1-10 alkyl and C 1-10 alkoxy, wherein said alkyl and alkoxy are optionally substituted with one or more halogen atoms; r 3 is selected from H, C 1-10 alkyl, C 3-10 cycloalkyl and 3-10 membered heterocycloalkyl, and n is an integer from 1 to 7. In some embodiments, the hindered amine light stabilizers of the present invention consist of two or more compounds of formula I. The second aspect of the invention provides a photovoltaic film comprising the hindered amine light stabilizer of the first aspect of the invention. In a third aspect the present invention provides an anti-ageing composition comprising (i) a hindered amine light stabilizer according to the first aspect of the present invention and (ii)